Production method for carbonate compound and methacrylate or ester thereof

Patent metadata

Field	Value
Publication number	US-9617379-B2
Application number	US-201615233981-A
Country	US
Kind code	B2
Filing date	Aug 11, 2016
Priority date	Feb 17, 2014
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

The present invention relates to a method for producing a carbonate compound and methacrylic acid or an ester thereof, containing a step (a1) of obtaining hexachloroacetone and hydrogen chloride from acetone and chlorine molecule, a step (a2) of obtaining a dialkyl carbonate and chloroform from hexachloroacetone and an alkyl alcohol, a step (b1) of obtaining 1,1,1-trichloro-2-methyl-2-propanol from chloroform and acetone, a step (b2+b3 or b4) of obtaining methacrylic acid or an ester thereof and hydrogen chloride from 1,1,1-trichloro-2-methyl-2-propanol and water or an alcohol, and a step (c1 or c2) of obtaining chlorine molecule by reacting hydrogen chloride with oxygen molecule.

First claim

The invention claimed is:

1. A method for producing a carbonate compound and methacrylic acid or an ester thereof, comprising:
(a1) a step of reacting acetone with chlorine molecule to obtain hexachloroacetone and hydrogen chloride,
(a2) a step of reacting the hexachloroacetone obtained in the step (a1) with an alkyl alcohol having a carbon number of from 1 to 10 to obtain a dialkyl carbonate and chloroform,
(b1) a step of reacting chloroform with acetone to obtain 1,1,1-trichloro-2-methyl-2-propanol,
(b2) a step of reacting the 1,1,1-trichloro-2-methyl-2-propanol obtained in the step (b1) with water or an alcohol that has a carbon number of from 1 to 10 in which a part or all of hydrogen atoms bonded to carbon atoms may be replaced by halogen atom(s) and/or deuterium atom(s), to obtain 2-chloro-2-methylpropanoic acid or an ester thereof and hydrogen chloride,
(b3) a step of obtaining methacrylic acid or an ester thereof and hydrogen chloride from the 2-chloro-2-methylpropanoic acid or the ester thereof obtained in the step (b2), and
(c1) a step of reacting the hydrogen chloride obtained in the step (a1), the step (b2), and the step (b3) with oxygen molecule to obtain chlorine molecule,
wherein the step (b2) contains reacting the 1,1,1-trichloro-2-methyl-2-propanol obtained in the step (b1) in the presence of a Lewis acid catalyst at a temperature lower than the boiling point of the 1,1,1-trichloro-2-methyl-2-propanol,
after the chloroform is obtained in the step (a2), the chloroform obtained in the step (a2) is used as at least a part of the chloroform in the step (b1), and
after the chlorine molecule is obtained in the step (c1), the chlorine molecule obtained in the step (c1) is used as at least a part of the chlorine molecule in the step (a1).

2. The method for producing a carbonate compound and methacrylic acid or an ester thereof according to claim 1 ,
wherein the step (b2) comprises reacting the 1,1,1-trichloro-2-methyl-2-propanol obtained in the step (b1) in the presence of the Lewis acid catalyst at the temperature lower than the boiling point of the 1,1,1-trichloro-2-methyl-2-propanol and further reacting the resulting one with the water or the alcohol that has a carbon number of from 1 to 10 in which a part or all of hydrogen atoms bonded to carbon atoms may be replaced by halogen atom(s) and/or deuterium atom(s), to obtain the 2-chloro-2-methylpropanoic acid or the ester thereof and the hydrogen chloride.

3. The method for producing a carbonate compound and methacrylic acid or an ester thereof according to claim 1 ,
wherein the step (b2) comprises reacting the 1,1,1-trichloro-2-methyl-2-propanol obtained in the step (b1) with the water or the alcohol that has a carbon number of from 1 to 10 in which a part or all of hydrogen atoms bonded to carbon atoms may be replaced by halogen atom(s) and/or deuterium atom(s), in the presence of the Lewis acid catalyst at the temperature lower than the boiling point of the 1,1,1-trichloro-2-methyl-2-propanol to obtain the 2-chloro-2-methylpropanoic acid or the ester thereof and the hydrogen chloride.

4. A method for producing a carbonate compound and methacrylic acid or an ester thereof, comprising:
(a1) a step of reacting acetone with chlorine molecule to obtain hexachloroacetone and hydrogen chloride,
(a2) a step of reacting the hexachloroacetone obtained in the step (a1) with an alkyl alcohol having a carbon number of from 1 to 10 to obtain a dialkyl carbonate and chloroform,
(b1) a step of reacting chloroform with acetone to obtain 1,1,1-trichloro-2-methyl-2-propanol,
(b4) a step of reacting the 1,1,1-trichloro-2-methyl-2-propanol obtained in the step (b1) with water or an alcohol that has a carbon number of from 1 to 10 in which a part or all of hydrogen atoms bonded to carbon atoms may be replaced by halogen atom(s) and/or deuterium atom(s), in the presence of a Lewis acid catalyst at a temperature equal to or higher than the boiling point of the 1,1,1-trichloro-2-methyl-2-propanol to obtain methacrylic acid or an ester thereof and hydrogen chloride, and
(c2) a step of reacting the hydrogen chloride obtained in the step (a1) and the step (b4) with oxygen molecule to obtain chlorine molecule,
wherein, after the chloroform is obtained in the step (a2), the chloroform obtained in the step (a2) is used as at least a part of the chloroform in the step (b1), and
after the chlorine molecule is obtained in the step (c2), the chlorine molecule obtained in the step (c2) is used as at least a part of the chlorine molecule in the step (a1).

5. The method for producing a carbonate compound and methacrylic acid or an ester thereof according to claim 1 , further comprising:
(a3) a step of reacting the dialkyl carbonate obtained in the step (a2) with phenol to obtain diphenyl carbonate and an alkyl alcohol having a carbon number of from 1 to 10, and
(a4) a step of reacting the diphenyl carbonate obtained in the step (a3) with bisphenol A to obtain an aromatic polycarbonate and phenol
wherein, after the alkyl alcohol having a carbon number of from 1 to 10 is obtained in the step (a3), the alkyl alcohol having a carbon number of from 1 to 10 obtained in the step (a3) is used as at least a part of the alkyl alcohol having a carbon number of from 1 to 10 in the step (a2), and
after the phenol is obtained in the step (a4), the phenol obtained in the step (a4) is used as at least a part of the phenol in the step (a3).

6. The method for producing a carbonate compound and methacrylic acid or an ester thereof according to claim 2 , further comprising:
(a3) a step of reacting the dialkyl carbonate obtained in the step (a2) with phenol to obtain diphenyl carbonate and an alkyl alcohol having a carbon number of from 1 to 10, and
(a4) a step of reacting the diphenyl carbonate obtained in the step (a3) with bisphenol A to obtain an aromatic polycarbonate and phenol
wherein, after the alkyl alcohol having a carbon number of from 1 to 10 is obtained in the step (a3), the alkyl alcohol having a carbon number of from 1 to 10 obtained in the step (a3) is used as at least a part of the alkyl alcohol having a carbon number of from 1 to 10 in the step (a2), and
after the phenol is obtained in the step (a4), the phenol obtained in the step (a4) is used as at least a part of the phenol in the step (a3).

7. The method for producing a carbonate compound and methacrylic acid or an ester thereof according to claim 3 , further comprising:
(a3) a step of reacting the dialkyl carbonate obtained in the step (a2) with phenol to obtain diphenyl carbonate and an alkyl alcohol having a carbon number of from 1 to 10, and
(a4) a step of reacting the diphenyl carbonate obtained in the step (a3) with bisphenol A to obtain an aromatic polycarbonate and phenol
wherein, after the alkyl alcohol having a carbon number of from 1 to 10 is obtained in the step (a3), the alkyl alcohol having a carbon number of from 1 to 10 obtained in the step (a3) is used as at least a part of the alkyl alcohol having a carbon number of from 1 to 10 in the step (a2), and
after the phenol is obtained in the step (a4), the phenol obtained in the step (a4) is used as at least a part of the phenol in the step (a3).

8. The method for producing a carbonate compound and methacrylic acid or an ester thereof according to claim 4 , further comprising:
(a3) a step of reacting the dialkyl carbonate obtained in the step (a2) with phenol to obtain diphenyl carbonate and an alkyl alcohol having a carbon number of from 1 to 10, and
(a4) a step of reacting the diphenyl carbonate obtained in the step (a3) with bisphenol A to obtain an aromatic polycarbonate and phenol
wherein, after the alkyl alcohol having a carbon number of from 1 to 10 is obtained in the step (

Assignees

• Asahi Glass Co Ltd

Inventors

• Okazoe Takashi
• Miyazaki Masayuki
• Oharu Kazuya
• Fujita Tomoyuki
• Wada Shinji
• Murata Koichi
• Shirota Naoko

Classifications

• C08G64/06

  not containing aliphatic unsaturation · CPC title

• C07C17/361

  by reactions involving a decrease in the number of carbon atoms · CPC title

• C08G64/307 Primary

  and phenols · CPC title

• C07C51/377

  by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups {(C07C51/36 - C07C51/373 take precedence)} · CPC title

• C07C67/14

  from carboxylic acid halides · CPC title