Aromatic acylation with cyclic anhydride for plasticizer production

Patent metadata

Field	Value
Publication number	US-9580571-B2
Application number	US-201314100694-A
Country	US
Kind code	B2
Filing date	Dec 9, 2013
Priority date	Dec 24, 2009
Publication date	Feb 28, 2017
Grant date	Feb 28, 2017

Abstract

Provided is a process for making non-phthalate plasticizers, by acylating an aromatic compound with a succinic anhydride to form a keto-acid, and then esterifying the keto-acid with C 4 -C 13 OXO-alcohols to form a plasticizer compound. The aromatic rings of the aromatic compound may also be optionally hydrogenated.

First claim

What is claimed is:

1. A process for making non-phthalate plasticizers, comprising acylating an aromatic compound with a succinic anhydride to form a keto-acid, and esterifying the keto-acid with C 4 -C 13 OXO-alcohols to form a plasticizer compound;
wherein the aromatic compound is of the formula:

wherein R 1 is selected from the group consisting of H, C 1 -C 9 linear or branched alkyl, cycloalkyl, or C 1 -C 4 ether, and wherein there may be 1 or 2 R 1 groups present on the aromatic or saturated ring which may be the same or different, and the plasticizer compound is of the formula:

wherein R 1 is as set forth above, R 2 is the alkyl residue of the OXO-alcohols, and R 3 is H or C 1 -C 8 linear or branched alkyl group; and
further comprising hydrogenating the keto-group(s) of the plasticizer compound to form alcohol groups, and esterifying the alcohol groups with C 4 to C 13 linear or OXO-acids.

2. The process according to claim 1 , wherein the acylation is catalyzed by a heterogeneous catalyst, a mixed metal oxide or a Lewis acid.

3. The process according to claim 1 , wherein the acylation is conducted using a stoichiometric amount of AlCl 3 .

4. A process for making non-phthalate plasticizers, comprising acylating an aromatic compound with a succinic anhydride to form a keto-acid, and esterifying the keto-acid with C 4 -C 13 OXO-alcohols to form a plasticizer compound;
wherein the aromatic compound is of the formula:

R 1 is selected from the group consisting of H, C 1 -C 9 linear or branched alkyl, cycloalkyl or C 1 -C 4 ether and wherein there may be 1 or 2 R 1 groups present on the aromatic or saturated ring which may be the same or different, and the plasticizer compound is of the formula:

wherein R 1 is as set forth above, R 2 is the alkyl residue of the OXO-alcohols, and R 3 is H or C 1 -C 8 linear or branched alkyl group; and
further comprising hydrogenating one or more of the aromatic rings.

5. The process of claim 4 , further comprising hydrogenating the keto-group(s) of the plasticizer compound to form alcohol groups, and esterifying the alcohol groups with C 4 to C 13 linear or OXO-acids to form plasticizer compounds of the formula:

wherein R 4 is the alkyl residue of said linear or OXO-acids.

Assignees

• Exxonmobil Res & Eng Co

Inventors

• Dakka Jihad Mohammed
• Mozeleski Edmund John
• Baugh Lisa Saunders
• Schall Colle Karla
• Godwin Allen David
• Smirnova Diana S
• Weber Jorg Friedrich Wilhelm
• Zushma Stephen

Classifications

• C07C69/738

  Esters of keto-carboxylic acids {or aldehydo-carboxylic acids} · CPC title

• C07C69/732

  of unsaturated hydroxy carboxylic acids · CPC title

• C07C59/84

  containing six membered aromatic rings · CPC title

• C07C67/31

  by introduction of functional groups containing oxygen only in singly bound form · CPC title

• C08K5/12 Primary

  of cyclic polycarboxylic acids · CPC title