Production of diesters from dinitrile compounds

Patent metadata

Field	Value
Publication number	US-9464027-B2
Application number	US-73921308-A
Country	US
Kind code	B2
Filing date	Oct 21, 2008
Priority date	Oct 31, 2007
Publication date	Oct 11, 2016
Grant date	Oct 11, 2016

Abstract

Diesters are prepared by first hydrolyzing dinitrile compounds into imide compounds and then reacting such imide compounds with at least one alcohol.

First claim

What is claimed is:

1. A process for the preparation of at least one diester compound comprising the following stages:
a) preparing an imide compound of the following formula (I):

 wherein A is a linear or branched divalent hydrocarbon radical having from 2 to 12 carbon atoms,
by hydrolyzing, in the presence of water, at least one dinitrile compound of following formula (III):
NC-A-CN  (III)

and
b) reacting said imide compound with at least one alcohol of the following formula (II):
R—OH  (II)

 wherein R is a linear or branched aliphatic, cycloaliphatic, aromatic or arylalkyl hydrocarbon radical having from 1 to 20 carbon atoms and optionally containing heteroatoms,
to obtain a reaction product comprising at least one diester compound of the following formula (IV) and optionally by-products of different formula(e):
R—OOC-A-COO—R  (IV)

wherein:
stage a) is carried out in the vapor phase in the presence of a solid catalyst, and
stage b) is carried out in the presence of at least one catalyst other than that employed during stage a).

2. The process as defined by claim 1 , wherein stage b) is carried out in the presence of a basic catalyst, and said basic catalyst is selected from the group consisting of:
organic salts comprising a basic anion,
inorganic bases,
heterogeneous basic catalysts, and
alkali metals in the metallic form.

3. The process as defined by claim 1 , wherein stage b) is carried out in the presence of a basic catalyst which comprises:
an alkali metal alkoxide,
metallic sodium,
lanthanum oxide, or
magnesium oxide.

4. The process as defined by claim 1 , wherein stage a) is carried out in the presence of a solid acid catalyst, and stage b) is carried out in the presence of a basic catalyst.

5. The process as defined by claim 1 , wherein stage b) is carried out in the liquid or vapor phase.

6. The process as defined by claim 1 , wherein stage a) is carried out at a temperature of less than 500° C.

7. The process as defined by claim 1 , wherein, during stage a), the molar ratio of the water to the nitrile compound ranges from 2 to 20.

8. The process as defined by claim 1 , wherein, during stage b), the molar ratio of the alcohol to the imide compound ranges from 1 to 30.

9. The process as defined by claim 1 , wherein the at least one dinitrile compound is selected from the group consisting of methylglutaronitrile, ethylsuccinonitrile, adiponitrile and mixtures thereof.

10. The process as defined by claim 1 , wherein the at least one alcohol is selected from the group consisting of methanol, propanol, isopropanol, benzyl alcohol, ethanol, n-butanol, isobutanol, pentanols, cyclohexanol, hexanol, isooctanol, 2-ethylhexanol and mixtures thereof.

11. The process as defined by claim 1 , wherein stage a) is carried out in the presence of a solid acid catalyst, and the solid acid catalyst is selected from the group consisting of:
metal oxides, alumina, titanium oxides, silica/alumina mixtures,
zeolites in the acid form,
clays in the acid form,
acid phosphates, NaH 2 PO 4 , and silicon pyrophosphate.

12. The process as defined by claim 11 , wherein the solid acid catalyst comprises anatase titanium dioxide.

13. The process as defined by claim 1 , wherein stage b) is carried out in the liquid phase at a temperature of less than 400° C., and at a pressure of 1 to 100 bar.

14. The process as defined by claim 1 , further comprising a stage c), after stage b):
stage c): heating the reaction product from stage b) and distilling, and recovering the diester compound.

15. The process as defined by claim 14 , wherein the reaction product from stage b) comprises a by-product which is converted to an imide of formula (I) during stage c) and which is then employed in carrying out stage b).

16. The process as defined by claim 1 , wherein, during stage b), ammonia is formed and then removed during this stage.

17. The process as defined by claim 1 , wherein, in stage a) hydrolyzing, in the presence of water, at least one dinitrile compound precedes addition of the solid catalyst and wherein, in stage b), reacting said imide compound with at least one alcohol precedes addition of a catalyst other than the one used for stage a).

Assignees

• Jacquot Roland
• Leconte Philippe
• Rhodia Operations

Inventors

• Jacquot Roland
• Leconte Philippe

Classifications

• C07C67/20 Primary

  from amides or lactams · CPC title

• C07C69/44

  Adipic acid esters · CPC title

• C07C69/34

  Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom · CPC title