MC Chem Wiki - User contributions [en]

Synthesis and Characterization of Lignin Monomers

2020-05-14T23:00:55Z

Rsitko750: /* Experimental Procedures */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

Ethanol

Acetyl Chloride

===Safety===

==Experimental Procedures==

Preparation of 2 mM Ferulic Acid Standards
* 100 mL solution is made with pH 5 buffer using deionized water
* 0.0385 g of Ferulic Acid added to pH 5 buffer

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.
[[File:IMG_2031.JPG|300px|right]]
Preparation_________

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons). Producing the ferulic acid standard is used in HPLC analysis. Running samples of standards and product from experimental procedures through the HPLC instrument looking at the intensity over a retention time of 30 minutes.

[[File:HPLC Data.jpg|400px]] [[File:Screenshot (2).png|400px]]

=Discusion=

=Conclusion=

Through more compassion between procedures would allow for a more green approach in a laboratory setting. With the possibility of a microwave reactor would allow for lignin synthesis to be rapidly produced.

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T23:00:13Z

Rsitko750: /* Experimental Procedures */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

Ethanol

Acetyl Chloride

===Safety===

==Experimental Procedures==

Preparation of 2 mM Ferulic Acid Standards
* 100 mL solution is made with pH 5 buffer using deionized water
* 0.0385 g of Ferulic Acid added to pH 5 buffer

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

Preparation_________
[[File:IMG_2031.JPG|400px|right]]
*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons). Producing the ferulic acid standard is used in HPLC analysis. Running samples of standards and product from experimental procedures through the HPLC instrument looking at the intensity over a retention time of 30 minutes.

[[File:HPLC Data.jpg|400px]] [[File:Screenshot (2).png|400px]]

=Discusion=

=Conclusion=

Through more compassion between procedures would allow for a more green approach in a laboratory setting. With the possibility of a microwave reactor would allow for lignin synthesis to be rapidly produced.

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

File:IMG 2031.JPG

2020-05-14T22:59:46Z

Rsitko750: File uploaded with MsUpload

File uploaded with MsUpload

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:53:38Z

Rsitko750: /* Results */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

Ethanol

Acetyl Chloride

===Safety===

==Experimental Procedures==

Preparation of 2 mM Ferulic Acid Standards
* 100 mL solution is made with pH 5 buffer using deionized water
* 0.0385 g of Ferulic Acid added to pH 5 buffer

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons). Producing the ferulic acid standard is used in HPLC analysis. Running samples of standards and product from experimental procedures through the HPLC instrument looking at the intensity over a retention time of 30 minutes.

[[File:HPLC Data.jpg|400px]] [[File:Screenshot (2).png|400px]]

=Discusion=

=Conclusion=

Through more compassion between procedures would allow for a more green approach in a laboratory setting. With the possibility of a microwave reactor would allow for lignin synthesis to be rapidly produced.

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:52:54Z

Rsitko750:

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

Ethanol

Acetyl Chloride

===Safety===

==Experimental Procedures==

Preparation of 2 mM Ferulic Acid Standards
* 100 mL solution is made with pH 5 buffer using deionized water
* 0.0385 g of Ferulic Acid added to pH 5 buffer

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|400px|right]]

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons). Producing the ferulic acid standard is used in HPLC analysis. Running samples of standards and product from experimental procedures through the HPLC instrument looking at the intensity over a retention time f 30 minutes.

[[File:Screenshot (2).png|400px|right]]

=Discusion=

=Conclusion=

Through more compassion between procedures would allow for a more green approach in a laboratory setting. With the possibility of a microwave reactor would allow for lignin synthesis to be rapidly produced.

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:34:01Z

Rsitko750: /* Results */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

Ethanol

Acetyl Chloride

===Safety===

==Experimental Procedures==

Preparation of 2 mM Ferulic Acid Standards
* 100 mL solution is made with pH 5 buffer using deionized water
* 0.0385 g of Ferulic Acid added to pH 5 buffer

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|400px|right]]

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons). Producing the ferulic acid standard is used in HPLC analysis. Running samples of standards and product through

[[File:Screenshot (2).png|400px|right]]

=Discusion=

=Conclusion=

Through more compassion between procedures would allow for a more green approach in a laboratory setting. With the possibility of a microwave reactor would allow for lignin synthesis to be rapidly produced.

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:32:33Z

Rsitko750: /* Experimental Procedures */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

Ethanol

Acetyl Chloride

===Safety===

==Experimental Procedures==

Preparation of 2 mM Ferulic Acid Standards
* 100 mL solution is made with pH 5 buffer using deionized water
* 0.0385 g of Ferulic Acid added to pH 5 buffer

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|400px|right]]

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons).

[[File:Screenshot (2).png|400px|right]]

=Discusion=

=Conclusion=

Through more compassion between procedures would allow for a more green approach in a laboratory setting. With the possibility of a microwave reactor would allow for lignin synthesis to be rapidly produced.

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:32:07Z

Rsitko750: /* Experimental Procedures */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

Ethanol

Acetyl Chloride

===Safety===

==Experimental Procedures==

Preparation of 2 mM Ferulic Acid Standards

100 mL solution is made with pH 5 buffer using deionized water

0.0385 g of Ferulic Acid added to pH 5 buffer

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|400px|right]]

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons).

[[File:Screenshot (2).png|400px|right]]

=Discusion=

=Conclusion=

Through more compassion between procedures would allow for a more green approach in a laboratory setting. With the possibility of a microwave reactor would allow for lignin synthesis to be rapidly produced.

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:29:03Z

Rsitko750: /* Materials */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

Ethanol

Acetyl Chloride

===Safety===

==Experimental Procedures==

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|400px|right]]

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons).

[[File:Screenshot (2).png|400px|right]]

=Discusion=

=Conclusion=

Through more compassion between procedures would allow for a more green approach in a laboratory setting. With the possibility of a microwave reactor would allow for lignin synthesis to be rapidly produced.

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:27:58Z

Rsitko750: /* Materials */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

===Safety===

==Experimental Procedures==

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|400px|right]]

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons).

[[File:Screenshot (2).png|400px|right]]

=Discusion=

=Conclusion=

Through more compassion between procedures would allow for a more green approach in a laboratory setting. With the possibility of a microwave reactor would allow for lignin synthesis to be rapidly produced.

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:27:22Z

Rsitko750: /* Conclusion */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

==Experimental Procedures==

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|400px|right]]

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons).

[[File:Screenshot (2).png|400px|right]]

=Discusion=

=Conclusion=

Through more compassion between procedures would allow for a more green approach in a laboratory setting. With the possibility of a microwave reactor would allow for lignin synthesis to be rapidly produced.

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:24:48Z

Rsitko750: /* Results */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

==Experimental Procedures==

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|400px|right]]

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons).

[[File:Screenshot (2).png|400px|right]]

=Discusion=

=Conclusion=

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:23:46Z

Rsitko750: /* Results */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

==Experimental Procedures==

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|600px|right]]

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons).

-

-

-

-

[[File:Screenshot (2).png|400px]]

=Discusion=

=Conclusion=

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

File:Screenshot (2).png

2020-05-14T22:23:38Z

Rsitko750: File uploaded with MsUpload

File uploaded with MsUpload

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:23:16Z

Rsitko750: /* Results */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

==Experimental Procedures==

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|600px|right]]

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons).

-

-

-

-

=Discusion=

=Conclusion=

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:22:58Z

Rsitko750: /* Results */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

==Experimental Procedures==

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|600px|right]]

While minimal research was able to be accomplished, discussion on methods were able to be looked at to finding a more green chemistry approach. The initial method allowed for a two day reflux accumulating in a significant amount of water being used (roughly 700+ gallons).

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-

=Discusion=

=Conclusion=

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:20:15Z

Rsitko750: /* References */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

==Experimental Procedures==

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|600px|right]]

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-

=Discusion=

=Conclusion=

== References ==

1. [[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

2. [[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

3. [[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

4. [[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

5. [https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
*PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

6. [https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
*PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-14T22:18:59Z

Rsitko750: /* Synthesis */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

==Experimental Procedures==

Preparation through 8--5 Coupled Diferulate Procedure ()
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C.
* '''Dimerization:''' Product of ethyl ferulate dissolved in pH 4.0 acetate buffer. Solution is cooled and added to peroxidase(10 mg in 2 mL of phosphate buffer). Product filtered out to obtain crude product.
* '''Purification:''' Use of flash chromatography with EtOAc as eluant. Product recrystallized allowing for NMR data and melting point.

*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|600px|right]]

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-

=Discusion=

=Conclusion=

== References ==

*[[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

*[[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

*[[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

*[[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

*[https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
**PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

*[https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
**PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-09T16:08:41Z

Rsitko750: /* References */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

==Synthesis==
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C. (Ralph)
*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|600px|right]]

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-

=Discusion=

=Conclusion=

== References ==

*[[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

*[[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

*[[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

*[[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

*[https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
**PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

*[https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
**PDF Version: [[:File:Structure-Activity Relationships.pdf]]

Synthesis and Characterization of Lignin Monomers

2020-05-09T16:06:43Z

Rsitko750: /* References */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

==Synthesis==
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C. (Ralph)
*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|600px|right]]

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-

=Discusion=

=Conclusion=

== References ==

*[https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]
**PDF Version: [[:File:Simple Preparation of 8-5 Coupled Diferu.pdf]]

*[https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]
**PDF Version: [[:File:Structure-Activity Relationships.pdf]]

*[[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

*[[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

*[[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

*[[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

File:Structure-Activity Relationships.pdf

2020-05-09T16:06:33Z

Rsitko750: File uploaded with MsUpload

File uploaded with MsUpload

Synthesis and Characterization of Lignin Monomers

2020-05-09T16:01:40Z

Rsitko750: /* References */

Synthesis and Characterization of Lignin Monomers

2020-05-09T16:00:43Z

Rsitko750: Undo revision 14394 by Rsitko750 (talk)

Synthesis and Characterization of Lignin Monomers

2020-05-09T16:00:02Z

Rsitko750: /* References */

Prior research on [http://esr.monmsci.net/wiki/index.php/Synthesis_of_Lignin_Monomers Synthesis of Lignin Monomers] done by: Alexandria N. Tibbs

=Abstract=
Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

==Lignin Monomers==
[https://en.wikipedia.org/wiki/Paracoumaryl_alcohol p-Coumaryl alcohol]

[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|500px|thumbnail|Lignin Precursors]]

[[File:P-Coumaryl_alcohol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Coniferyl_alcohol Coniferyl alcohol]

[[File:Coniferol.svg.png|250px]]

[https://en.wikipedia.org/wiki/Sinapyl_alcohol Sinapyl alcohol]

[[File:Sinapyl_alcohol.svg.png|250px]]

=Introduction=
Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

=Methods/Experimentation=

==Materials==
[https://www.sigmaaldrich.com/catalog/product/aldrich/128708?lang=en&region=US Ferulic acid]

[https://www.sigmaaldrich.com/catalog/product/sigma/c9008?lang=en&region=US p-Coumaric acid]

[https://www.sigmaaldrich.com/catalog/product/aldrich/d7927?lang=en&region=US Sinapic acid]

==Synthesis==
*'''Ethyl Ferulate:''' 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C. (Ralph)
*'''Esterification:''' 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

===Synthesis Mechanism===

=Results=

[[File:HPLC Data.jpg|600px|right]]

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-

-

=Discusion=

=Conclusion=

== References ==

*[https://pubs.acs.org/doi/abs/10.1021/jf980123r Simple Preparation of 8--5-coupled Diferulate]

*PDF Version: [http://:File:Simple%20Preparation%20of%208-5%20Coupled%20Diferu.pdf Simple Preparation of 8-5 Coupled Diferulate]

*[https://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01281 Structure-Activity Relationships]

*[[Media:Lignin biosynthesis and Structure.pdf|Lignin Biosynthesis and Structure]]

*[[Media:Lignin ref Burkit.pdf|Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals]]

*[[https://books.google.com/books?hl=en&lr=&id=E74LS-rm6t8C&oi=fnd&pg=PP1&dq=lignin+and+lignans+advances+in+chemistry+overview&ots=CAXGjH-1vt&sig=i4mXAsF5VhIWhelYS7AUhr5virg#v=onepage&q&f=false| Overview from ''Lignin and Lignans: Advances in Chemistry'']]

*[[Media:Alcohol synthesis procedure.pdf|Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol]]

Synthesis and Characterization of Lignin Monomers

2020-05-09T15:59:03Z

Rsitko750: /* Conclusion */

Synthesis and Characterization of Lignin Monomers

2020-05-09T15:58:08Z

Rsitko750: /* References */

File:Simple Preparation of 8-5 Coupled Diferu.pdf

2020-05-09T15:57:47Z

Rsitko750: File uploaded with MsUpload

File uploaded with MsUpload

Synthesis and Characterization of Lignin Monomers

2020-05-07T17:51:57Z

Rsitko750: /* Results */

Synthesis and Characterization of Lignin Monomers

2020-05-07T17:51:45Z

Rsitko750: /* Results */

Synthesis and Characterization of Lignin Monomers

2020-05-07T17:51:34Z

Rsitko750: /* Results */

Synthesis and Characterization of Lignin Monomers

2020-05-07T17:51:23Z

Rsitko750: /* Results */

Synthesis and Characterization of Lignin Monomers

2020-05-07T17:51:11Z

Rsitko750: /* Results */

Synthesis and Characterization of Lignin Monomers

2020-05-07T17:50:50Z

Rsitko750: /* Results */

Synthesis and Characterization of Lignin Monomers

2020-05-07T17:50:36Z

Rsitko750: /* Results */

Synthesis and Characterization of Lignin Monomers

2020-05-07T17:50:18Z

Rsitko750: /* Results */

Synthesis and Characterization of Lignin Monomers

2020-05-07T17:50:04Z

Rsitko750: /* Results */

Synthesis and Characterization of Lignin Monomers

2020-05-07T06:41:22Z

Rsitko750: /* Methods/Experimentation */

Synthesis and Characterization of Lignin Monomers

2020-05-07T06:28:39Z