Process for preparing diaryl oxalate

Patent metadata

Field	Value
Publication number	US-9174918-B2
Application number	US-201113522979-A
Country	US
Kind code	B2
Filing date	Jan 20, 2011
Priority date	Jan 20, 2010
Publication date	Nov 3, 2015
Grant date	Nov 3, 2015

Abstract

Disclosed is a process for preparing a diaryl oxalate which comprises the step of transesterifying a dialkyl oxalate or/and an alkylaryl oxalate with an aryl alcohol in the presence of a tetra(aryloxy)titanium as a catalyst, wherein the tetra(aryloxy)titanium is fed into a reaction system of the transesterification as an aryl alcohol solution of the tetra(aryloxy)titanium which is prepared by reacting a tetraalkoxy titanium and an excess amount of the aryl alcohol and removing a by-producing alkyl alcohol.

First claim

The invention claimed is:

1. A process for preparing a diaryl oxalate which comprises steps of:
reacting a tetraalkoxy titanium and an excess amount of an aryl alcohol and removing a by-producing alkyl alcohol to obtain an aryl alcohol solution of a tetra(aryloxy)titanium;
thereafter feeding the obtained aryl alcohol solution of a tetra(aryloxy)titanium in a reaction system of transesterification as a catalyst of the transesterification;
transesterifying, in the reaction system, an alkylaryl oxalate with an aryl alcohol in the presence of the catalyst to prepare the diaryl oxalate; and
making a concentration of a titanium compound of a reaction mixture containing the diaryl oxalate 10 ppm by weight or less, and then, purifying by distillation, in order to obtain a diaryl oxalate with 500 ppm or less benzofuran-2,3-diones as a coloring component,
wherein a material of an apparatus contacting with a reaction solution of the transesterification is an austenitic stainless steel containing 10% by weight or more of nickel and 1 to 4% by weight of molybdenum, or containing 16.00 to 18.00% by weight of chromium; and
wherein the material of an apparatus is an austenitic stainless steel substantially not containing a nitrogen atom.

2. The process for preparing diaryl oxalate according to claim 1 , wherein the tetra(aryloxy)titanium is tetraphenoxy titanium.

3. The process for preparing diaryl oxalate according to claim 1 , wherein the tetraalkoxy titanium is tetraisopropoxy titanium.

4. The process for preparing diaryl oxalate according to claim 1 , wherein the reaction of the tetraalkoxy titanium and an excess amount of the aryl alcohol is carried out so that a molar ratio (aryl alcohol/titanium atom) of the aryl alcohol and a titanium atom in the tetraalkoxy titanium becomes 10 to 80.

5. The process for preparing diaryl oxalate according to claim 1 , wherein the reaction of the tetraalkoxy titanium and an excess amount of the aryl alcohol is carried out while maintaining a reaction temperature at 160 to 300° C.

6. The process for preparing diaryl oxalate according to claim 1 , wherein the reaction of the tetraalkoxy titanium and an excess amount of the aryl alcohol is carried out in a reaction-distillation column.

7. The process for preparing diaryl oxalate according to claim 6 , wherein a reflux ratio of the tetraalkoxy titanium and an excess amount of the aryl alcohol in the reaction-distillation column is 3 to 40.

8. The process for preparing diaryl oxalate according to claim 6 , wherein the tetraalkoxy titanium and an excess amount of the aryl alcohol are continuously fed to the reaction-distillation column so that a molar ratio (aryl alcohol/titanium atom) of the aryl alcohol and a titanium atom in the tetraalkoxy titanium per a unit time becomes 40 to 80.

9. The process for preparing diaryl oxalate according to claim 1 , wherein the tetraalkoxy titanium and an excess amount of the aryl alcohol are fed to a reaction-distillation column to carry out a reaction, a fraction containing a by-producing alkyl alcohol is taken out by distillation, and a fraction containing the tetra(aryloxy)titanium and the aryl alcohol is taken out from a bottom portion, to obtain an aryl alcohol solution of the tetra(aryloxy)titanium from which the by-producing alkyl alcohol had been removed, and fed the same to a transesterification step.

10. The process for preparing diaryl oxalate according to claim 9 , wherein the tetra(aryloxy)titanium and the aryl alcohol are continuously taken out from a bottom portion of the reaction-distillation column, and the aryl alcohol solution of the tetra(aryloxy)titanium from which the by-producing alkyl alcohol had been removed is continuously fed to the transesterification step.

11. The process for preparing diaryl oxalate according to Claim 1 , wherein a material of an apparatus is a SUS316 series austenitic stainless steel regulated by JIS G 4304.

12. The process for preparing diaryl oxalate according to claim 11 , wherein the austenitic stainless steel is SUS316 or SUS316L regulated by JIS G 4304.

13. The process for preparing diaryl oxalate according to claim 1 , wherein an apparatus is a purification column of the diaryl oxalate, a reaction apparatus of transesterification or a reaction-distillation column.

14. A process for preparing diaryl carbonate which comprises decarbonylating the diaryl oxalate prepared by the process according to claim 1 in the presence of a phosphorus compound.

15. A process for preparing polycarbonate which comprises reacting diaryl carbonate prepared by the process according to claim 14 with bisphenol A in the presence of a basic alkali metal salt.

Assignees

• Tanaka Shuji
• Ii Hirofumi
• Ube Industries

Inventors

• Tanaka Shuji
• Ii Hirofumi

Classifications

• C07C68/00

  Preparation of esters of carbonic or haloformic acids · CPC title

• C07C67/03 Primary

  by reacting an ester group with a hydroxy group · CPC title

• C07C69/96

  Esters of carbonic or haloformic acids · CPC title

• C08G64/307

  and phenols · CPC title

• C07C69/36

  Oxalic acid esters · CPC title