Synthesis of Lignin Monomers - Revision history

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2019-05-01T21:36:16Z

Discussion

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Experimental

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2019-05-01T21:27:13Z

Experimental

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Experimental

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2019-05-01T21:03:01Z

Experimental

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Results

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2019-05-01T20:57:10Z

Results

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Results

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Results

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Materials

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 ==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.
+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. It can be proposed that the quality of the final product will improve with the greater number of trials ran. Another way to approach an improvement in purity would be to run the solutions through the flash chromatography instrument after the extraction process of the esterified solution and prior to the DIBAL-H step of the method.
 ==References==

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 A third esterification process was ran using a 0.15M solution of ferulic acid ethanol (250mL ethanol, 8.2g ferulic acid) along with 25mL of acetyl chloride. All other parameters were the same as the initial esterification. (Figure 5)
-'''Step Two''': DIBAL-H Reduction (Figure 6)
+This process also applies to the other monomoers of lignin. This inital process was run on ''p''-coumaric acid to for ''p''-coumaric acid ethyl ester (Figure 7)
-The reduction process was done using the strong reducing agent diisobutylaluminum hydride (DIBAL-H). All processes in step two were done under nitrogen due to the strong reactive properties of DIBAL-H with oxygen and hydrogen. The product from step one (third attempt) was placed into a three-armed round bottom flask containing a stir bar and 100mL of toluene was added via syringe and placed in an ice bath. Approximately 52mL of DIBAL-H was added to the solution through an addition funnel over a 10 minute time span while stirring. The reaction stirred for 1 hour. After 1 hour the solution was quenched with 5mL of ethanol. The solution was then rotovapped at 40 degrees Celsius. After evaporation, 100mL of water was added to the solution. The solution was extracted using 2 rinses of 150 mL ethyl acetate and finally rotovapped until a solid product formed. (Figure 5)
+'''Step Two''': DIBAL-H Reduction (Figure 4)
 ==Results==

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 The process can most simply be broken up into two main steps
-'''Step One''': Esterification
+'''Step One''': Esterification (Figure 2)
 The esterification of ferulic acid and other monomers was the first step in the reduction of acid to alcohol by replacing the carboxylic acid group with an ethyl ester protecting group. A 0.24M solution of ferulic acid in ethanol (250 mL ethanol, 12.1g ferulic acid) along with 3 drops of concentrated HCl 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 tested in the HPlc (Figure 1).
-A second attempt at the esterification of ferulic acid was carried out using the same method as above, but on a 1/5 scale. (Figure 3) However, this time instead of using 3 drops of concentrted HCL, 5 mL of acetly chloride was added to the solution before reflux. All other reflux solutions used the protocol containing the acetly chloride.
+A second attempt at the esterification of ferulic acid was carried out using the same method as above, but on a 1/5 scale. (Figure 3) However, this time instead of using 3 drops of concentrated HCL, 5 mL of acetyl chloride was added to the solution before reflux. All other reflux solutions used the protocol containing the acetyl chloride.
 ==Results==

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 ==Experimental==
-The esterification of ferulic 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).
+The process can most simply be broken up into two main steps
-A second attempt at the esterification of ferulic 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).
+'''Step One''': Esterification
 ==Results==

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 ==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).
+The esterification of ferulic 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).
+A second attempt at the esterification of ferulic 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==

← Older revision		Revision as of 21:01, 1 May 2019
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	[[File:P-cou.png\|thumb\|center\|Figure 7: HPLC results of P-coumaric acid standard and after esterficication]]		[[File:P-cou.png\|thumb\|center\|Figure 7: HPLC results of P-coumaric acid standard and after esterficication]]
		+
		+	Figure 7 displays chromatograms of HPLC results for a ''p''-coumaric acid standand and then the ''p''-coumaric acid ethyl ester.

	==Discussion==		==Discussion==

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 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]]
+[[File:P-cou.png|thumb|center|Figure 7: HPLC results of P-coumaric acid standard and after esterficication]]
 ==Discussion==

← Older revision		Revision as of 20:21, 1 May 2019
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	[[File:2nd Dibal-H run.png\|thumb\|center\|Figure 5: HPLC Results for Esterification of Ferulic Acid]]		[[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.

	==Discussion==		==Discussion==

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 '''Other General Lab Materials'''