Process for the manufacture of α,α-branched carboxylic acid vinyl esters

Patent metadata

Field	Value
Publication number	US-9260374-B2
Application number	US-201214007699-A
Country	US
Kind code	B2
Filing date	Apr 3, 2012
Priority date	Apr 7, 2011
Publication date	Feb 16, 2016
Grant date	Feb 16, 2016

Abstract

The invention relates to a process for the manufacture of α,α-branched carboxylic acids vinyl esters comprising the following steps:
isomerizing and converting an olefin feed with CO and water under Koch reaction conditions to make an acid with a ratio of Non Blocking isomers (NB) versus Blocking isomers (B) of NB/B above 1.5, wherein a blocking isomer has always a tertiary carbon atom in alpha position of the carboxylic acid and in the beta position of the carboxylic acid, whereas a non-blocking isomer has primary carbon atoms in the beta position of the carboxylic acid converting the resulting acid into a vinyl ester.

First claim

The invention claimed is:

1. A process for the manufacture of α,α-branched carboxylic acid vinyl esters comprising:
converting a propylene oligomer olefin feed with CO and water under Koch reaction conditions and wherein the propylene oligomer olefin feed has an isomer ratio of (BR1+BR2)/BR3=Ya above 20, with BR1=weight of propylene oligomer olefin with one branching alkyl group, BR2=weight of propylene oligomer olefin with two branching alkyl groups and BR3=weight of propylene oligomer olefin with three or more branching alkyl groups to make an acid with a ratio of Non Blocking isomers (NB) versus Blocking isomers (B) of NB/B above 1.5, where the α carbon atom is always quaternary, the carbon atom(s) in β position can either be secondary, tertiary, or quaternary, acids with a tertiary or a quaternary carbon atoms in the β position are defined as blocking isomers,
converting the resulting acids into vinyl esters.

2. The process of claim 1 wherein the propylene olefin feed is mainly a trimer of propylene or mainly a tetramer of propylene.

3. The process of claim 1 wherein the resulting acid is reacted with acetylene in presence of a zinc catalyst.

4. The process of claim 3 wherein the propylene oligomer is mainly a trimer of propylene with Ya composition and wherein the resulting acids are reacted with acetylene in presence of a zinc salt to produce vinyl esters of branched carboxylic acids with a copolymer Tg of 26.5° C. or lower.

5. A copolymer comprising of the vinyl esters produced according to claim 1 .

6. A process for the manufacture of α,α-branched carboxylic acids comprising:
converting a propylene oligomer olefin feed with CO and water under Koch reaction conditions and wherein the propylene oligomer olefin feed has an isomer ratio of (BR1+BR2)/BR3=Ya above 20, with BR1=weight of propylene oligomer olefin with one branching alkyl group, BR2=weight of propylene oligomer olefin with two branching alkyl groups and BR3=weight of propylene oligomer olefin with three or more branching alkyl groups to make an acid with a ratio of Non Blocking isomers (NB) versus Blocking isomers (B) of NB/B above 1.5, where the α carbon atom is always quaternary, the carbon atom(s) in β position can either be secondary, tertiary, or quaternary, acids with a tertiary or a quaternary carbon atoms in the β position are defined as blocking isomers.

7. The process of any one of claim 1 , wherein the resulting acid is reacted with acetylene in presence of a zinc catalyst with a throughput of the reaction of at least 5.3 ton/hour.

Assignees

• Heymans Denis
• Hexion Inc

Inventors

• Heymans Denis

Classifications

• C08K5/101 Primary

  of monocarboxylic acids · CPC title

• C07C69/24

  esterified with monohydroxylic compounds · CPC title

• C07C67/38 Primary

  by addition to an unsaturated carbon-to-carbon bond · CPC title

• C07C51/14 Primary

  on a carbon-to-carbon unsaturated bond in organic compounds · CPC title

• C07C69/56

  Crotonic acid esters; Vinyl acetic acid esters · CPC title