Synthesis of novel ionic liquids from lignin-derived compounds

Patent metadata

Field	Value
Publication number	US-9765044-B2
Application number	US-201414776454-A
Country	US
Kind code	B2
Filing date	Mar 14, 2014
Priority date	Mar 15, 2013
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

Methods and compositions are provided for synthesizing ionic liquids from lignin derived compounds comprising: contacting a starting material comprising lignin with a depolymerization agent to depolymerize the lignin and form a mixture of aldehyde containing compounds; contacting the mixture of aldehyde containing compounds with an amine under conditions suitable to convert the mixture of aldehyde containing compounds to a mixture of amine containing compounds; and contacting the mixture of amine containing compounds with an acid under conditions suitable to form an ammonium salt, thereby preparing the ionic liquid.

First claim

What is claimed is:

1. A method for preparing an ionic liquid comprising:
contacting a starting material comprising lignin with a depolymerization agent to depolymerize the lignin and form a mixture of aldehyde containing compounds;
contacting the mixture of aldehyde containing compounds with an amine under conditions suitable to convert the mixture of aldehyde containing compounds to a mixture of amine containing compounds; and
contacting the mixture of amine containing compounds with an acid under conditions suitable to form an ammonium salt, thereby preparing the ionic liquid, wherein:
the ionic liquid comprises at least one compound of the following formula:

wherein each of the R groups of the nitrogen is independently selected from the group consisting of H, CH 3 , and CH 2 CH 3 ;
at least two of the R groups of the nitrogen are independently selected from the group consisting of CH 3 , and CH 2 CH 3 ;
R′, R″, and R′″ are independently selected from the group consisting of H, OH, and OCH 3 ;
R 4 is selected from the group consisting of H, OH, and CH 2 OH; and
X comprises an acid anion.

2. The method of claim 1 , wherein the step of contacting the starting material with a depolymerization agent comprises contacting the starting material with one or more compositions selected from the group consisting of an ionic liquid; hydrogen gas; a hydrogen donating agent selected from the group consisting of tetralin, sodium formate and formic acid; a dilute acid; a concentrated acid; a base; a catalyst and an oxidizing agent selected from the group consisting of nitrobenzene, metal oxides, hydrogen peroxide, and oxygen gas; Fenton's reagent; metal organic frameworks of copper or iron; and ammonium hydroxide.

3. The method of claim 2 , wherein the depolymerization agent comprises a lignin-derived ionic liquid.

4. The method of claim 2 , wherein the depolymerization agent comprises an imidazolium ionic liquid.

5. The method of claim 1 , wherein the step of contacting the mixture of aldehyde containing compounds with an amine is performed under reducing conditions.

6. The method of claim 5 , wherein the reducing conditions comprise an amine, a Brønsted acid; and a hydride donating reducing agent.

7. The method of claim 6 , wherein the amine is selected from the group consisting of a cyclic amine, an acyclic amine, a monoamine, and a dialkylamine.

8. The method of claim 6 , wherein the Brønsted acid is selected from the group consisting of formic acid, acetic acid, proprionic acid, and an aromatic carboxylic acid.

9. The method of claim 6 , wherein the reducing agent is selected from the group consisting of sodium triacetoxyborohydride, sodium cyanoborohydride, sodium borohydride-trifluoroacetic acid, hydrogen gas and a catalyst, and polymethylhydrosiloxane (PMHS).

10. The method of claim 1 , wherein the step of contacting the mixture of amine containing compounds with an acid under conditions suitable to form an amine salt comprises a salt metathesis reaction, wherein the conditions of the salt metathesis reaction comprise acid in a polar solvent.

11. The method of claim 10 , wherein the acid is a mineral acid selected from the group consisting of sulfuric and phosphoric acid.

12. The method of claim 1 , wherein the contacting steps are performed in a single reaction vessel.

Assignees

• Univ California
• Sandia Corp

Inventors

• Socha Aaron
• Singh Seema
• Simmons Blake A
• Bergeron Maxime

Classifications

• C07D295/03

  with the ring nitrogen atoms directly attached to acyclic carbon atoms · CPC title

• C07C209/04

  by substitution of functional groups by amino groups · CPC title

• C07C215/50

  with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain · CPC title

• C12P19/02

  Monosaccharides (2-ketogulonic acid C12P7/60) · CPC title

• C07C213/08

  by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups · CPC title