By:[http://esr.monmsci.net/wiki/index.php/Alexandria_N_Tibbs Alexandria N. Tibbs]

==Introduction==
Lignin is the second most abundant organic polymer. It is found in plants, majorly in trees. Its function is to serve in the assistance of water flow throughout the plant. It forms a barrier for the evaporation, trapping the water inside.

The structure of lignin is composed of the seemingly random combination of three monomers: ''p''-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol. The monomers only differ by the number of methoxy groups present on the phenol. The phenol group contributes the the overall stability of the molecules' formed radicals. These radicals determine the bonding spot between monomers when creating lignin. These monomers can also join together to form dimers that are known as Lignan; which has biological activity.
{|
|[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|400px|thumb|left|Lignin Precursors]]
|}
These lignin monomers are derived from their acid precursors through the reduction of an aldehyde to the corresponding alcohol. While the acid precursors,[https://www.sigmaaldrich.com/catalog/search?term=p-coumaric+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ''p''-courmaric acid] (''p''-coumaryl alcohol), [https://www.sigmaaldrich.com/catalog/search?term=ferulic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ferulic acid] [https://www.sigmaaldrich.com/catalog/product/aldrich/223735?lang=en&region=US (coniferyl alcohol)], and [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product sinapic acid] [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product (sinapyl alcohol)] may not be as abundant in nature, when it comes to the lab setting, these chemicals are easier to come by than their alcohol forms. The synthesis of theses alcohols can save a research space a great deal of money when experiments require the alcohol forms of these monomers; such as others in the Sturgeon research group.

==Materials==
[https://www.sigmaaldrich.com/catalog/search?term=192724&interface=Product%20No.&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Diisobutylaluminum hydride solution] (25 wt.% in toluene)

'''Product Number''': 192724-100G

'''Quantity''': 2

'''Price''': $52.20

[https://www.sigmaaldrich.com/catalog/search?term=Toluene&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Toluene ] (Anhydrous, 99.8%)

'''Product Number''': 244511-1L

'''Quantity''': 1

'''Price''': $60.50

[https://www.sigmaaldrich.com/catalog/search?term=acetyl+chloride&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product Acetyl Chloride Solution]

'''Product Number''': 708496-100mL

'''Quantity''': 1

'''Price''': $45.50

'''Other General Lab Materials'''
*Ethanol
*Sodium Bicarbonate
*Brine
*Magnesium Sulfate

'''Lab Hardware'''
*Various sized Round Bottom Flasks
*Heating Mantle
*Reflux Condenser
*Water Pump
*Separation Funnel
*Rotovap Vacuum Distiller
*Bubbler
*Dririte Air/Gas Dryer

==Experimental==

The esterfication of ferlic acid was the first step in the reduction of ferulic acid to coniferyl alcohol. First attempt was made using a 0.24M solution of ferulic acid in ethanol (250 mL ethanol, 12.1g ferulic acid). Along with 3 drops of concentrated HCl this was allowed to reflux for two days. The resulting solution was evaporated at low pressure, leaving a solid. This solid was then resolubilized in ethyl acetate (250 mL) and rinsed with sodium bicarbonate (2x100 mL) and brine (50 mL). The solution was dried using magnesium sulfate and evaporated at low pressure, resulting in an oil like solution. The final product was testing in the HPlc (Figure 1).

A second attempt at the esterfication of ferukic acid was carried out using the same method as above, but on a 1/5 scale. An HPLC was done of the intermediate that is present after 1 day of refluxing (Figure 1).

==Results==
[[File:Figure 1.jpg|275px|thumb|center|Figure 1: HPLC Results after esterfication of Ferulic Acid]]

Figure 1 displays the results of HPLC testing that was run on 3 separate samples. The first is the ferulic acid standard. The second is a sample of the final product from the first attempt at the esterfication of ferulic acid. The third is a more dilute sample of the same sample from the second chromatogram. All samples were run using the acquisition method: pCou_100417_SAZT.

[[Image:FA to ETFA final.png|thumb|center|Figure 2: Reaction of Ferulic acid to Ethyl Ferulate]]

Figure 2 displays the chemical reaction of ferulic acid into ethyl ferulate. This displays the chemical process that occurs during the first steps of this reaction. There is a substitution of functional groups from the carboxylic acid to an ethyl ester protecting group.

[[File:Second reflux to final.jpg|275px|thumb|center|Figure 3: HPLC Results after Second Attempt at Esterfication of Ferulic Acid]]

Figure 3 displays the results of HPLC testing that was run on 3 separate samples. The first graph represents the sample of the reflux intermediate from the second attempt at the esterfication process.The second is the ferulic acid standard. The third is the sample of the reflux intermediate from the second attempt at esterfication of ferulic acid after one and a half days of reflux. The fourth graph is the results from a sample of the final product, indicating the esterfication of ferulic acid to ethyl ferulate. The fifth graph is the product, coniferyl alcohol, after the DIABL-H steps of the reaction. All samples were run using the acquisition method: pCou_100417_SAZT.

[[File:Ethyl ferulate to coniferyl alcohol.png|thumb|center|Figure 4: Reaction of Ethyl Ferulate to Coniferyl Alcohol]]

Figure 4 displays the chemical reaction Ethyl Ferulate to Coniferyl Alcohol. This displays the chemical process that occurs during the second steps of this reaction. The ethyl ester protecting group is reduced to the alcohol functional group.

[[File:2nd Dibal-H run.png|thumb|center|Figure 5: HPLC Results for Esterification of Ferulic Acid]]

Figure 5 displays the chromatograms that were produced from running the solution in the HPLC. The initial chromatogram is the Ferulic acid solution before reflux. The Next three are the ethyl ferulate solution after 24 hours of reflux, after 48 hours of reflux, and after the solution had been rotovapped and gone through the extraction process.

[[File:2nd Dibal-H run part2.png|thumb|center|Figure 6: HPLC Results from DIBAL-H reaction of Ethyl Ferulate]]

Figure 6 displays the chromatograms for the material after the DIBAL-H portion of the reaction. The first is the solution after the initial reduction process. The second is the solution after it had been rotovapped and extracted. The final chromatogram is the coniferyl alcohol standard.

[[File:P-cou.png Figure 7: HPLC results of P-coumaric acid standard and after esterficication]]

==Discussion==

Definite progress was made in the ability to synthesize the alcohol form of the lignin monomers; there is still a great deal of work to be done. A clear improvement in purity of the samples was seen from the initial trials to the later trials. There is still room for improvement when it comes to the purity levels of the substances.

==References==

[[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:P-cou.png

2019-05-01T20:52:59Z

Atibbs:

Synthesis of Lignin Monomers

2019-05-01T20:21:38Z

Atibbs: /* Results */

By:[http://esr.monmsci.net/wiki/index.php/Alexandria_N_Tibbs Alexandria N. Tibbs]

==Motivation==

==Introduction==
Lignin is the second most abundant organic polymer. It is found in plants, majorly in trees. Its function is to serve in the assistance of water flow throughout the plant. It forms a barrier for the evaporation, trapping the water inside.

The structure of lignin is composed of the seemingly random combination of three monomers: ''p''-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol.

{|
|[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|400px|thumb|left|Lignin Precursors]]
|}

'''FIX THE LINKS IN THIS PARAGRAPH'''

These lignin monomers are derived from their acid precursors through the reduction of an aldehyde to the corresponding alcohol. While the acid precursors,[https://www.sigmaaldrich.com/catalog/search?term=p-coumaric+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ''p''-courmaric acid] (''p''-coumaryl alcohol), [https://www.sigmaaldrich.com/catalog/search?term=ferulic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ferulic acid] [https://www.sigmaaldrich.com/catalog/searchterm=Coniferyl+alcohol&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 (coniferyl alcohol)], and [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product sinapic acid] [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product (sinapyl alcohol)] may not be as abundant in nature, when it comes to the lab setting, these chemicals are easier to come by then their alcohol forms. The synthesis of theses alcohols can save a research space a great deal of money, if experiments require the alcohol forms of these monomers.

==Materials==
[https://www.sigmaaldrich.com/catalog/search?term=192724&interface=Product%20No.&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Diisobutylaluminum hydride solution] (25 wt.% in toluene)

'''Product Number''': 192724-100G

'''Quantity''': 2

'''Price''': $52.20

[https://www.sigmaaldrich.com/catalog/search?term=Toluene&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Toluene ] (Anhydrous, 99.8%)

'''Product Number''': 244511-1L

'''Quantity''': 1

'''Price''': $60.50

==Experimental==

The esterfication of ferlic acid was the first step in the reduction of ferulic acid to coniferyl alcohol. First attempt was made using a 0.24M solution of ferulic acid in ethanol (250 mL ethanol, 12.1g ferulic acid). Along with 3 drops of concentrated HCl this was allowed to reflux for two days. The resulting solution was evaporated at low pressure, leaving a solid. This solid was then resolubilized in ethyl acetate (250 mL) and rinsed with sodium bicarbonate (2x100 mL) and brine (50 mL). The solution was dried using magnesium sulfate and evaporated at low pressure, resulting in an oil like solution. The final product was testing in the HPlc (Figure 1).

A second attempt at the esterfication of ferukic acid was carried out using the same method as above, but on a 1/5 scale. An HPLC was done of the intermediate that is present after 1 day of refluxing (Figure 1).

==Results==
[[Image:Fa etfa reflux.jpg|275px|thumb|Figure 1: HPLC Results after esterfication of Ferulic Acid]]
[[Image:FA to ETFA final.png|thumb|center|Figure 2: Reaction of ferulic acid to ethyl ferulate]]
[[Image:ETFA2 06 22 22.jpg|275px|thumb|right|Figure 3: HPLC Results after second attempt at esterfication of Ferulic Acid]]

Figure 1 displays the results of HPLC testing that was run on 4 separate samples. The first is the ferulic acid standard. The second is a sample of the final product from the first attempt at the esterfication of ferulic acid. The third is a more dilute sample of the samp sample from the second graph. The final graph represents the sample of the reflux intermediate from the second attempt at the esterfication process. All samples were run using the acquisition method: pCou_100417_SAZT.

Figure 3 displays the results oif HPLC testing that was run on 3 separate samples. The first is the ferulic acid standard. The second is the sample of the reflux intermediate from the second attempt at esterfication of ferulic acid after one and a half days of reflux. The third graph is the results from a sample of the final product, indicating the esterfication of ferulic acid to ethyl ferulate. All samples were run using the acquisition method: pCou_100417_SAZT.

==Discussion==

==References==

[[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:Fa etfa reflux.jpg

2018-07-06T19:27:47Z

Atibbs: Atibbs uploaded a new version of File:Fa etfa reflux.jpg

Synthesis of Lignin Monomers

2018-06-22T16:47:03Z

Atibbs: /* Results */

By:[http://esr.monmsci.net/wiki/index.php/Alexandria_N_Tibbs Alexandria N. Tibbs]

==Motivation==

==Introduction==
Lignin is the second most abundant organic polymer. It is found in plants, majorly in trees. Its function is to serve in the assistance of water flow throughout the plant. It forms a barrier for the evaporation, trapping the water inside.

The structure of lignin is composed of the seemingly random combination of three monomers: ''p''-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol.

{|
|[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|400px|thumb|left|Lignin Precursors]]
|}

'''FIX THE LINKS IN THIS PARAGRAPH'''

These lignin monomers are derived from their acid precursors through the reduction of an aldehyde to the corresponding alcohol. While the acid precursors,[https://www.sigmaaldrich.com/catalog/search?term=p-coumaric+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ''p''-courmaric acid] (''p''-coumaryl alcohol), [https://www.sigmaaldrich.com/catalog/search?term=ferulic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ferulic acid] [https://www.sigmaaldrich.com/catalog/searchterm=Coniferyl+alcohol&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 (coniferyl alcohol)], and [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product sinapic acid] [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product (sinapyl alcohol)] may not be as abundant in nature, when it comes to the lab setting, these chemicals are easier to come by then their alcohol forms. The synthesis of theses alcohols can save a research space a great deal of money, if experiments require the alcohol forms of these monomers.

==Materials==
[https://www.sigmaaldrich.com/catalog/search?term=192724&interface=Product%20No.&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Diisobutylaluminum hydride solution] (25 wt.% in toluene)

'''Product Number''': 192724-100G

'''Quantity''': 2

'''Price''': $52.20

[https://www.sigmaaldrich.com/catalog/search?term=Toluene&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Toluene ] (Anhydrous, 99.8%)

'''Product Number''': 244511-1L

'''Quantity''': 1

'''Price''': $60.50

==Experimental==

The esterfication of ferlic acid was the first step in the reduction of ferulic acid to coniferyl alcohol. First attempt was made using a 0.24M solution of ferulic acid in ethanol (250 mL ethanol, 12.1g ferulic acid). Along with 3 drops of concentrated HCl this was allowed to reflux for two days. The resulting solution was evaporated at low pressure, leaving a solid. This solid was then resolubilized in ethyl acetate (250 mL) and rinsed with sodium bicarbonate (2x100 mL) and brine (50 mL). The solution was dried using magnesium sulfate and evaporated at low pressure, resulting in an oil like solution. The final product was testing in the HPlc (Figure 1).

A second attempt at the esterfication of ferukic acid was carried out using the same method as above, but on a 1/5 scale. An HPLC was done of the intermediate that is present after 1 day of refluxing (Figure 1).

==Results==
[[Image:Fa etfa reflux.jpg|275px|thumb|left|Figure 1: HPLC Results after esterfication of Ferulic Acid]]
[[Image:FA to ETFA final.png|thumb|center|Figure 2: Reaction of ferulic acid to ethyl ferulate]]
[[Image:ETFA2 06 22 22.jpg|275px|thumb|right|Figure 3: HPLC Results after second attempt at esterfication of Ferulic Acid]]

Figure 1 displays the results of HPLC testing that was run on 4 separate samples. The first is the ferulic acid standard. The second is a sample of the final product from the first attempt at the esterfication of ferulic acid. The third is a more dilute sample of the samp sample from the second graph. The final graph represents the sample of the reflux intermediate from the second attempt at the esterfication process. All samples were run using the acquisition method: pCou_100417_SAZT.

Figure 3 displays the results oif HPLC testing that was run on 3 separate samples. The first is the ferulic acid standard. The second is the sample of the reflux intermediate from the second attempt at esterfication of ferulic acid after one and a half days of reflux. The third graph is the results from a sample of the final product, indicating the esterfication of ferulic acid to ethyl ferulate. All samples were run using the acquisition method: pCou_100417_SAZT.

==Discussion==

==References==

[[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 of Lignin Monomers

2018-06-22T16:45:34Z

Atibbs: /* Results */

By:[http://esr.monmsci.net/wiki/index.php/Alexandria_N_Tibbs Alexandria N. Tibbs]

==Motivation==

==Introduction==
Lignin is the second most abundant organic polymer. It is found in plants, majorly in trees. Its function is to serve in the assistance of water flow throughout the plant. It forms a barrier for the evaporation, trapping the water inside.

The structure of lignin is composed of the seemingly random combination of three monomers: ''p''-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol.

{|
|[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|400px|thumb|left|Lignin Precursors]]
|}

'''FIX THE LINKS IN THIS PARAGRAPH'''

These lignin monomers are derived from their acid precursors through the reduction of an aldehyde to the corresponding alcohol. While the acid precursors,[https://www.sigmaaldrich.com/catalog/search?term=p-coumaric+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ''p''-courmaric acid] (''p''-coumaryl alcohol), [https://www.sigmaaldrich.com/catalog/search?term=ferulic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ferulic acid] [https://www.sigmaaldrich.com/catalog/searchterm=Coniferyl+alcohol&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 (coniferyl alcohol)], and [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product sinapic acid] [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product (sinapyl alcohol)] may not be as abundant in nature, when it comes to the lab setting, these chemicals are easier to come by then their alcohol forms. The synthesis of theses alcohols can save a research space a great deal of money, if experiments require the alcohol forms of these monomers.

==Materials==
[https://www.sigmaaldrich.com/catalog/search?term=192724&interface=Product%20No.&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Diisobutylaluminum hydride solution] (25 wt.% in toluene)

'''Product Number''': 192724-100G

'''Quantity''': 2

'''Price''': $52.20

[https://www.sigmaaldrich.com/catalog/search?term=Toluene&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Toluene ] (Anhydrous, 99.8%)

'''Product Number''': 244511-1L

'''Quantity''': 1

'''Price''': $60.50

==Experimental==

The esterfication of ferlic acid was the first step in the reduction of ferulic acid to coniferyl alcohol. First attempt was made using a 0.24M solution of ferulic acid in ethanol (250 mL ethanol, 12.1g ferulic acid). Along with 3 drops of concentrated HCl this was allowed to reflux for two days. The resulting solution was evaporated at low pressure, leaving a solid. This solid was then resolubilized in ethyl acetate (250 mL) and rinsed with sodium bicarbonate (2x100 mL) and brine (50 mL). The solution was dried using magnesium sulfate and evaporated at low pressure, resulting in an oil like solution. The final product was testing in the HPlc (Figure 1).

A second attempt at the esterfication of ferukic acid was carried out using the same method as above, but on a 1/5 scale. An HPLC was done of the intermediate that is present after 1 day of refluxing (Figure 1).

==Results==
[[File:Fa etfa reflux.jpg|275px|thumb|left|Figure 1: HPLC Results after esterfication of Ferulic Acid]]
[[File:FA to ETFA final.png|thumb|center|Figure 2: Reaction of ferulic acid to ethyl ferulate]]
[[File:ETFA2 06 22 22.jpg|275px|thumb|right|Figure 3: HPLC Results after second attempt at esterfication of Ferulic Acid]]

Figure 1 displays the results of HPLC testing that was run on 4 separate samples. The first is the ferulic acid standard. The second is a sample of the final product from the first attempt at the esterfication of ferulic acid. The third is a more dilute sample of the samp sample from the second graph. The final graph represents the sample of the reflux intermediate from the second attempt at the esterfication process. All samples were run using the acquisition method: pCou_100417_SAZT.

Figure 3 displays the results oif HPLC testing that was run on 3 separate samples. The first is the ferulic acid standard. The second is the sample of the reflux intermediate from the second attempt at esterfication of ferulic acid after one and a half days of reflux. The third graph is the results from a sample of the final product, indicating the esterfication of ferulic acid to ethyl ferulate. All samples were run using the acquisition method: pCou_100417_SAZT.

==Discussion==

==References==

[[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 of Lignin Monomers

2018-06-22T16:44:37Z

Atibbs: /* Results */

By:[http://esr.monmsci.net/wiki/index.php/Alexandria_N_Tibbs Alexandria N. Tibbs]

==Motivation==

==Introduction==
Lignin is the second most abundant organic polymer. It is found in plants, majorly in trees. Its function is to serve in the assistance of water flow throughout the plant. It forms a barrier for the evaporation, trapping the water inside.

The structure of lignin is composed of the seemingly random combination of three monomers: ''p''-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol.

{|
|[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|400px|thumb|left|Lignin Precursors]]
|}

'''FIX THE LINKS IN THIS PARAGRAPH'''

These lignin monomers are derived from their acid precursors through the reduction of an aldehyde to the corresponding alcohol. While the acid precursors,[https://www.sigmaaldrich.com/catalog/search?term=p-coumaric+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ''p''-courmaric acid] (''p''-coumaryl alcohol), [https://www.sigmaaldrich.com/catalog/search?term=ferulic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ferulic acid] [https://www.sigmaaldrich.com/catalog/searchterm=Coniferyl+alcohol&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 (coniferyl alcohol)], and [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product sinapic acid] [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product (sinapyl alcohol)] may not be as abundant in nature, when it comes to the lab setting, these chemicals are easier to come by then their alcohol forms. The synthesis of theses alcohols can save a research space a great deal of money, if experiments require the alcohol forms of these monomers.

==Materials==
[https://www.sigmaaldrich.com/catalog/search?term=192724&interface=Product%20No.&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Diisobutylaluminum hydride solution] (25 wt.% in toluene)

'''Product Number''': 192724-100G

'''Quantity''': 2

'''Price''': $52.20

[https://www.sigmaaldrich.com/catalog/search?term=Toluene&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Toluene ] (Anhydrous, 99.8%)

'''Product Number''': 244511-1L

'''Quantity''': 1

'''Price''': $60.50

==Experimental==

The esterfication of ferlic acid was the first step in the reduction of ferulic acid to coniferyl alcohol. First attempt was made using a 0.24M solution of ferulic acid in ethanol (250 mL ethanol, 12.1g ferulic acid). Along with 3 drops of concentrated HCl this was allowed to reflux for two days. The resulting solution was evaporated at low pressure, leaving a solid. This solid was then resolubilized in ethyl acetate (250 mL) and rinsed with sodium bicarbonate (2x100 mL) and brine (50 mL). The solution was dried using magnesium sulfate and evaporated at low pressure, resulting in an oil like solution. The final product was testing in the HPlc (Figure 1).

A second attempt at the esterfication of ferukic acid was carried out using the same method as above, but on a 1/5 scale. An HPLC was done of the intermediate that is present after 1 day of refluxing (Figure 1).

==Results==

Figure 1 displays the results of HPLC testing that was run on 4 separate samples. The first is the ferulic acid standard. The second is a sample of the final product from the first attempt at the esterfication of ferulic acid. The third is a more dilute sample of the samp sample from the second graph. The final graph represents the sample of the reflux intermediate from the second attempt at the esterfication process. All samples were run using the acquisition method: pCou_100417_SAZT.

Figure 3 displays the results oif HPLC testing that was run on 3 separate samples. The first is the ferulic acid standard. The second is the sample of the reflux intermediate from the second attempt at esterfication of ferulic acid after one and a half days of reflux. The third graph is the results from a sample of the final product, indicating the esterfication of ferulic acid to ethyl ferulate. All samples were run using the acquisition method: pCou_100417_SAZT.
[[File:Fa etfa reflux.jpg|275px|thumb|left|Figure 1: HPLC Results after esterfication of Ferulic Acid]]
[[File:FA to ETFA final.png|thumb|center|Figure 2: Reaction of ferulic acid to ethyl ferulate]]
[[File:ETFA2 06 22 22.jpg|275px|thumb|right|Figure 3: HPLC Results after second attempt at esterfication of Ferulic Acid]]

==Discussion==

==References==

[[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]]

2018-06-22T16:22:19Z

Atibbs:

By:[http://esr.monmsci.net/wiki/index.php/Alexandria_N_Tibbs Alexandria N. Tibbs]

==Motivation==

==Introduction==
Lignin is the second most abundant organic polymer. It is found in plants, majorly in trees. Its function is to serve in the assistance of water flow throughout the plant. It forms a barrier for the evaporation, trapping the water inside.

The structure of lignin is composed of the seemingly random combination of three monomers: ''p''-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol.

{|
|[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|400px|thumb|left|Lignin Precursors]]
|}

'''FIX THE LINKS IN THIS PARAGRAPH'''

These lignin monomers are derived from their acid precursors through the reduction of an aldehyde to the corresponding alcohol. While the acid precursors,[https://www.sigmaaldrich.com/catalog/search?term=p-coumaric+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ''p''-courmaric acid] (''p''-coumaryl alcohol), [https://www.sigmaaldrich.com/catalog/search?term=ferulic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ferulic acid] [https://www.sigmaaldrich.com/catalog/searchterm=Coniferyl+alcohol&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 (coniferyl alcohol)], and [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product sinapic acid] [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product (sinapyl alcohol)] may not be as abundant in nature, when it comes to the lab setting, these chemicals are easier to come by then their alcohol forms. The synthesis of theses alcohols can save a research space a great deal of money, if experiments require the alcohol forms of these monomers.

==Materials==
[https://www.sigmaaldrich.com/catalog/search?term=192724&interface=Product%20No.&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Diisobutylaluminum hydride solution] (25 wt.% in toluene)

'''Product Number''': 192724-100G

'''Quantity''': 2

'''Price''': $52.20

[https://www.sigmaaldrich.com/catalog/search?term=Toluene&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Toluene ] (Anhydrous, 99.8%)

'''Product Number''': 244511-1L

'''Quantity''': 1

'''Price''': $60.50

==Experimental==

The esterfication of ferlic acid was the first step in the reduction of ferulic acid to coniferyl alcohol. First attempt was made using a 0.24M solution of ferulic acid in ethanol (250 mL ethanol, 12.1g ferulic acid). Along with 3 drops of concentrated HCl this was allowed to reflux for two days. The resulting solution was evaporated at low pressure, leaving a solid. This solid was then resolubilized in ethyl acetate (250 mL) and rinsed with sodium bicarbonate (2x100 mL) and brine (50 mL). The solution was dried using magnesium sulfate and evaporated at low pressure, resulting in an oil like solution. The final product was testing in the HPlc (Figure 1).

A second attempt at the esterfication of ferukic acid was carried out using the same method as above, but on a 1/5 scale. An HPLC was done of the intermediate that is present after 1 day of refluxing (Figure 1).

==Results==

Figure 1 displays the results of HPLC testing that was run on 4 separate samples. The first is the ferulic acid standard. The second is a sample of the final product from the first attempt at the esterfication of ferulic acid. The third is a more dilute sample of the samp sample from the second graph. The final graph represents the sample of the reflux intermediate from the second attempt at the esterfication process. All samples were run using the acquisition method: pCou_100417_SAZT.
[[File:Fa etfa reflux.jpg|275px|thumb|left|Figure 1: HPLC Results after esterfication of Ferulic Acid]]
[[File:ETFA2 06 22 22.jpg|275px|thumb|left|Figure 2: HPLC Results after second attempt at esterfication of Ferulic Acid]]
Figure 2 displays the results oif HPLC testing that was run on 3 separate samples. The first is the ferulic acid standard. The second is the sample of the reflux intermediate from the second attempt at esterfication of ferulic acid after one and a half days of reflux. The third graph is the results from a sample of the final product, indicating the esterfication of ferulic acid to ethyl ferulate.

==Discussion==

==References==

[[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 of Lignin Monomers

2018-06-22T16:21:38Z

Atibbs: /* Results */

By:[http://esr.monmsci.net/wiki/index.php/Alexandria_N_Tibbs Alexandria N. Tibbs]

==Motivation==

==Introduction==
Lignin is the second most abundant organic polymer. It is found in plants, majorly in trees. Its function is to serve in the assistance of water flow throughout the plant. It forms a barrier for the evaporation, trapping the water inside.

The structure of lignin is composed of the seemingly random combination of three monomers: ''p''-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol.

{|
|[[File:Lignin-precursors-p-coumaryl-alcohol-H.png|400px|thumb|left|Lignin Precursors]]
|}

'''FIX THE LINKS IN THIS PARAGRAPH'''

These lignin monomers are derived from their acid precursors through the reduction of an aldehyde to the corresponding alcohol. While the acid precursors,[https://www.sigmaaldrich.com/catalog/search?term=p-coumaric+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ''p''-courmaric acid] (''p''-coumaryl alcohol), [https://www.sigmaaldrich.com/catalog/search?term=ferulic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product ferulic acid] [https://www.sigmaaldrich.com/catalog/searchterm=Coniferyl+alcohol&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 (coniferyl alcohol)], and [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product sinapic acid] [https://www.sigmaaldrich.com/catalog/search?term=sinapic+acid&interface=All&N=0&mode=match%20partialmax&lang=en&region=US&focus=product (sinapyl alcohol)] may not be as abundant in nature, when it comes to the lab setting, these chemicals are easier to come by then their alcohol forms. The synthesis of theses alcohols can save a research space a great deal of money, if experiments require the alcohol forms of these monomers.

==Materials==
[https://www.sigmaaldrich.com/catalog/search?term=192724&interface=Product%20No.&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Diisobutylaluminum hydride solution] (25 wt.% in toluene)

'''Product Number''': 192724-100G

'''Quantity''': 2

'''Price''': $52.20

[https://www.sigmaaldrich.com/catalog/search?term=Toluene&interface=Product%20Name&N=0+&mode=mode%20matchpartialmax&lang=en&region=US&focus=productN=0%20220003048%20219853286%20219853269 Toluene ] (Anhydrous, 99.8%)

'''Product Number''': 244511-1L

'''Quantity''': 1

'''Price''': $60.50

==Experimental==

The esterfication of ferlic acid was the first step in the reduction of ferulic acid to coniferyl alcohol. First attempt was made using a 0.24M solution of ferulic acid in ethanol (250 mL ethanol, 12.1g ferulic acid). Along with 3 drops of concentrated HCl this was allowed to reflux for two days. The resulting solution was evaporated at low pressure, leaving a solid. This solid was then resolubilized in ethyl acetate (250 mL) and rinsed with sodium bicarbonate (2x100 mL) and brine (50 mL). The solution was dried using magnesium sulfate and evaporated at low pressure, resulting in an oil like solution. The final product was testing in the HPlc (Figure 1).

A second attempt at the esterfication of ferukic acid was carried out using the same method as above, but on a 1/5 scale. An HPLC was done of the intermediate that is present after 1 day of refluxing (Figure 1).

==Results==
[[File:Fa etfa reflux.jpg|275px|thumb|left|Figure 1: HPLC Results after esterfication of Ferulic Acid]]
[[File:ETFA2 06 22 22.jpg|275px|thumb|left|Figure 2: HPLC Results after second attempt at esterfication of Ferulic Acid]]

Figure 1 displays the results of HPLC testing that was run on 4 separate samples. The first is the ferulic acid standard. The second is a sample of the final product from the first attempt at the esterfication of ferulic acid. The third is a more dilute sample of the samp sample from the second graph. The final graph represents the sample of the reflux intermediate from the second attempt at the esterfication process. All samples were run using the acquisition method: pCou_100417_SAZT.

Figure 2 displays the results oif HPLC testing that was run on 3 separate samples. The first is the ferulic acid standard. The second is the sample of the reflux intermediate from the second attempt at esterfication of ferulic acid after one and a half days of reflux. The third graph is the results from a sample of the final product, indicating the esterfication of ferulic acid to ethyl ferulate.

==Discussion==

==References==

[[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]]