Preparation of chemicals, monomers and polymers from plant oils

Patent metadata

Field	Value
Publication number	US-2016137591-A1
Application number	US-201514940300-A
Country	US
Kind code	A1
Filing date	Nov 13, 2015
Priority date	Nov 13, 2014
Publication date	May 19, 2016
Grant date	—

Abstract

Methods for forming a compound from a plant oil compound having a carboxylic acid group attached to an organic group are provided. The method can include performing an aminolysis reaction between the plant oil compound and a hydroxyl-containing amine compound to form a functionalized plant oil compound having an amide bond; and functionalizing the hydroxyl group to have a polyerizable vinyl group or a norbornene group to form a polyerizable plant oil compound having the amide bond and an ester bond.

First claim

What is claimed:

1 . A method for forming a compound from a plant oil compound having a carboxylic acid group attached to an organic group, the method comprising:
performing an aminolysis reaction between the plant oil compound and a hydroxyl-containing amine compound to form a functionalized plant oil compound having an amide bond; and functionalizing the hydroxyl group to have a polyerizable vinyl group or a norbornene group to form a polyerizable plant oil compound having the amide bond and an ester bond.

2 . The method of claim 1 , wherein the hydroxyl-containing amine compound is a primary or secondary amine.

3 . The method of claim 1 , wherein the plant oil compound is a triglyceride.

4 . The method of claim 1 , wherein the hydroxyl-containing amine compound comprises an alkanolamine compound.

5 . The method of claim 4 , wherein the alkanolamine compound comprises methanolamine, 2-aminoethanol, 3-aminopropanol, 4-amino-1-butanol, 5-amino-1-pentanol, or a mixture thereof.

6 . The method of claim 1 , wherein the hydroxyl-containing amine compound comprises N-methylethanolamine, 2-pyrrolidinemethanol, or a mixture thereof.

7 . The method of claim 1 , wherein the hydroxyl group is functionalized to have a polyerizable vinyl group by reacting the functionalized plant oil compound with a (meth)acryloyl halide.

8 . The method as in claim 7 , further comprising:
polymerizing the polyerizable vinyl group.

9 . The method of claim 1 , wherein the hydroxyl group is functionalized to have a norbornene group by reacting the functionalized plant oil compound with a

10 . The method as in claim 9 , further comprising:
polymerizing the norbornene group.

11 . A method for forming a polymer from a plant oil compound having a carboxylic acid group attached to an organic group, the method comprising:
performing an aminolysis reaction between the plant oil compound and a double hydroxyl-containing amine compound to form a functionalized plant oil compound having an amide bond; and polymerizing the functionalized plant oil compound.

12 . The method of claim 11 , wherein the amino group is a primary or secondary amine, and wherein the reaction compound having a carboxylic acid comprises a fatty acid.

13 . The method of claim 11 , wherein the plant oil compound is a triglyceride.

Assignees

• Univ South Carolina

Inventors

• Tang Chuanbing
• Yuan Liang

Classifications

• C08G18/3206

  aliphatic · CPC title

• C08F2438/02

  Stable Free Radical Polymerisation [SFRP]; Nitroxide Mediated Polymerisation [NMP] for, e.g. using 2,2,6,6-tetramethylpiperidine-1-oxyl [TEMPO] · CPC title

• C07D207/08

  with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms · CPC title

• C07C231/02

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title

• C07C231/12

  by reactions not involving the formation of carboxamide groups · CPC title