Keto acid esters as PVC plasticizers

Patent metadata

Field	Value
Publication number	US-9561996-B2
Application number	US-201013378959-A
Country	US
Kind code	B2
Filing date	Jun 21, 2010
Priority date	Jul 21, 2009
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

Abstract

Resin plasticizers are produced by esterification of keto acids derived from acylation of aromatic compounds with cyclic anhydrides, and are particularly useful in making phthalate-free articles using PVC.

First claim

What is claimed is:

1. A process for producing keto acid esters, the process comprising:
(a) a first step of Friedel crafts reaction of benzoyl chloride with benzene in the presence of an acidic catalyst comprising AlCl 3 to form benzophenone, a second step reaction of benzophenone with CO/HCl in a Gattermann-Koch reaction to form benzophenone aldehyde, a third step of the oxidation of the aldehyde to the acid, a fourth step of the esterification with an ROH alcohol, as illustrated in the following scheme:

(b) a first step reaction of benzoate ester with CO/HCl in a Gatterman-Koch reaction, a second step formation of acid chloride in the presence of SOCl 2 , a third reaction Friedel Crafts acylation in the presence of benzene and AlCl 3 , as illustrated in the following schematic:

wherein said ROH alcohol comprises a C6 to C13 alcohol derived from the oligomerization of at least one C3-C6 olefin to form an oligomer, followed by hydroformylation and hydrogenation reactions of said oligomer to form said C6 to C13 alcohol.

2. The process of claim 1 , wherein said hydroformylation reaction is catalyzed by a metal selected from Rh, Co, and mixtures thereof.

3. The process of claim 1 , wherein said hydroformylation reaction is catalyzed by Co.

4. The process of claim 1 , wherein said hydroformylation reaction is catalyzed by Rh.

5. The process of claim 1 , wherein said oligomerization is catalyzed by solid phosphoric acid, a zeolite, or a combination thereof.

Assignees

• Colle Karla S
• Weber Jorg F
• Godwin Allen D
• Exxonmobil Chemical Patents Inc

Inventors

• Colle Karla S
• Weber Jorg F
• Godwin Allen D

Classifications

• Y10T428/139

  Open-ended, self-supporting conduit, cylinder, or tube-type article · CPC title

• C07C67/343

  by increase in the number of carbon atoms · CPC title

• C07C67/313

  by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups · CPC title

• Y10T442/2369

  Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric · CPC title

• C07C45/68

  by increase in the number of carbon atoms · CPC title