Synthesis of novel ionic liquids from lignin-derived compounds

Patent metadata

Field	Value
Publication number	US-10155735-B2
Application number	US-201715669718-A
Country	US
Kind code	B2
Filing date	Aug 4, 2017
Priority date	Mar 15, 2013
Publication date	Dec 18, 2018
Grant date	Dec 18, 2018

Abstract

Methods and compositions are provided for synthesizing ionic liquids from lignin. Methods and compositions are also provided for treating lignin with ionic liquids.

First claim

What is claimed is:

1. A compound selected from:

wherein two of the R groups of each nitrogen are CH 2 CH 3 ;
one of the R groups of each nitrogen is H;
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 is an acid anion selected from the group consisting of acetate, dihydrogen phosphate, and hydrogen sulfate.

2. A mixture comprising at least two of the compounds of claim 1 .

3. A mixture comprising at least three of the compounds of claim 1 .

4. A mixture comprising at least four of the compounds of claim 1 .

5. A mixture comprising at least five of the compounds of claim 1 .

6. A mixture comprising at least six of the compounds of claim 1 .

7. A mixture comprising at least seven of the compounds of claim 1 .

8. A mixture comprising at least eight of the compounds of claim 1 .

9. A mixture comprising at least nine of the compounds of claim 1 .

10. A mixture comprising about 10% w/v of at least one compound of claim 1 .

11. A lignin-derived ionic liquid prepared by
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 a mineral acid under conditions suitable to form an ammonium salt, thereby preparing the lignin-derived ionic liquid,
wherein the lignin-derived ionic liquid is selected from:

wherein two the R groups of each nitrogen are CH 2 CH 3 ;
one of the R groups of each nitrogen is H;
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 is an acid anion selected from the group consisting of acetate, dihydrogen phosphate, and hydrogen sulfate.

12. The ionic liquid of claim 11 , wherein the ionic liquid is a room temperature ionic liquid.

13. The ionic liquid of claim 11 , wherein the ionic liquid has a melting point at atmospheric pressure of less than about 100° C.

Assignees

• The Regents Of The Unviersity Of California
• Nat Tech & Eng Solutions Sandia Llc
• Univ California

Inventors

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

Classifications

• C07C209/04

  by substitution of functional groups by amino groups · CPC title

• C07C213/08

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

• C07D295/03

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

• C07C211/27

  having amino groups linked to the six-membered aromatic ring by saturated carbon chains · CPC title

• C07C211/28

  having amino groups linked to the six-membered aromatic ring by unsaturated carbon chains · CPC title