Polymers from muconic acid isomers and its derivatives

Patent metadata

Field	Value
Publication number	US-11059919-B2
Application number	US-201515522123-A
Country	US
Kind code	B2
Filing date	Oct 23, 2015
Priority date	Oct 28, 2014
Publication date	Jul 13, 2021
Grant date	Jul 13, 2021

Abstract

This invention relates to polymerization of muconic acid and its derivatives. Muconic acid useful for the invention can be in any of its isomeric forms including cis, cis-muconic acid (ccMA), cis, trans-muconic acid (ctMA), and trans, trans-muconic acid (ttMA). Muconic acid used in the invention can be derived either from renewable carbon resources through biological fermentation or from non-renewable petrochemical resources through biological fermentation or chemical conversion.

First claim

What is claimed:

1. A method for making a polymer from muconic acid, the method comprising:
(a) obtaining muconic acid from a microorganism;
(b) optionally converting the muconic acid to a muconic acid derivative of the following formula (I)
RO 2 C—CH═CH—CH═CH—CO 2 R  (I)

wherein R is selected from the group consisting of an alkyl group, an aryl group, an alkyl aromatic group, and an aromatic alkyl group; and
(c) reacting the muconic acid or the muconic acid derivative via an electrochemical reaction, to obtain hex-3-enedioic acid or an alkyl, aryl, alkyl aromatic or aromatic alkyl ester of hex-3-enedioic acid,
(d) condensing the hex-3-enedioic acid or the alkyl, aryl, alkyl aromatic or aromatic alkyl ester of hex-3-enedioic acid with an aldehyde or ketone, and
(e) reacting a product of (d), to obtain the polymer.

2. The method of claim 1 , wherein R is CH 3 .

3. The method of claim 1 , wherein R is C 2 H 5 .

4. The method of claim 1 , wherein the microorganism is a bacterium.

Assignees

• Ptt Global Chemical Public Co Ltd

Inventors

• Milan Jay L
• Mang Michael
• Ozmeral Cenan

Classifications

• C08G63/08 Primary

  Lactones or lactides · CPC title

• C08F136/14

  containing elements other than carbon and hydrogen · CPC title

• C08F236/14

  containing elements other than carbon and hydrogen · CPC title

• C07C51/36

  by hydrogenation of carbon-to-carbon unsaturated bonds · CPC title

• C07C51/353

  by isomerisation; by change of size of the carbon skeleton · CPC title