Method for producing unsaturated acid ester or unsaturated acid

Patent metadata

Field	Value
Publication number	US-2016122279-A1
Application number	US-201614991393-A
Country	US
Kind code	A1
Filing date	Jan 8, 2016
Priority date	Jul 12, 2013
Publication date	May 5, 2016
Grant date	—

Abstract

The present invention relates to a method for producing an unsaturated-acid ester or an unsaturated acid, containing a step of reacting a compound (1) represented by the following formula (1) with a compound represented by the following formula (2) (excluding the compound (1)) in the presence of a Lewis acid catalyst at a temperature of the boiling point of the compound (1) or higher and 350° C. or lower, thereby obtaining products including a compound represented by the following formula (3):

(in formula (1) and formula (3), R 1 , R 2 and R 4 each independently may be hydrogen atom or an alkyl group, R 3 and R 5 each independently are hydrogen atom or a deuterium atom, and X is a halogen atom; in formula (2) and formula (3), R 6 may be hydrogen atom, an alkyl group or an aryl group, and R 7 is hydrogen atom or a deuterium atom).

First claim

1 . A method for producing an unsaturated-acid ester or an unsaturated acid, comprising a step of reacting a compound (1) represented by the following formula (1) with a compound (2) represented by the following formula (2) (excluding the compound (1)) in the presence of a Lewis acid catalyst at a temperature of the boiling point of the compound (1) or higher and 350° C. or lower, thereby obtaining products including a compound (3) represented by the following formula (3):

(in formula (1), R 1 , R 2 and R 4 each independently are a hydrogen atom, a deuterium atom, or an alkyl group which has a carbon number of from 1 to 3 and may have been substituted with a halogen atom and/or a deuterium atom, R 3 and R 5 each independently are a hydrogen atom or a deuterium atom, and X is a chlorine atom, a fluorine atom, a bromine atom, or an iodine atom);
R 6 —OR 7   (2)

(in formula (2), R 6 is a hydrogen atom, a deuterium atom, an alkyl group which has a carbon number of from 1 to 11 and may have been substituted with a halogen atom and/or a deuterium atom, or an aryl group which has a carbon number of from 1 to 11 and may have been substituted with a halogen atom and/or a deuterium atom, and R 7 is a hydrogen atom or a deuterium atom); and

(in formula (3), R 1 , R 2 and R 4 are the same as defined above with regard to formula (1), and R 6 is the same as defined above with regard to formula (2)).

2 . The method for production according to claim 1 , wherein the Lewis acid catalyst is any of compounds represented by the following formula (4) (excluding water) or a mixture of these.
M n Y m   (4)
(in formula (4), M is a cation of hydrogen or a metal or metalloid selected from the group consisting of elements of Group 2 and Groups from 4 to 14 of the periodic table, Y is an anion selected from the group consisting of oxide ions, halide ions, a sulfate ion, a nitrate ion, a carbonate ion, a hydrogen carbonate ion, a sulfide ion, a hydroxide ion, alkoxide ions, a phosphate ion, an acetate ion, and a perchlorate ion, and n and m are numbers satisfying (valence of the cation M)×n=(valence of the anion Y)×m).

3 . The method for production according to claim 2 , wherein the M is a cation of a metal or metalloid selected from the group consisting of zinc, zirconium, silicon, chromium, iron, aluminum, lead, magnesium, indium, cobalt, manganese, and nickel.

4 . The method for production according to claim 2 , wherein the Y is an oxide ion.

5 . The method for production according to claim 1 , wherein the Lewis acid catalyst is a solid acid.

6 . The method for production according to claim 5 , wherein the solid acid is at least one member selected from the group consisting of activated clay, acid clay, zeolites, heteropolyacids, and ion-exchange resins.

7 . The method for production according to claim 1 , wherein the reaction is conducted in a gas phase.

Assignees

• Asahi Glass Co Ltd

Inventors

• Fujita Tomoyuki
• Murata Koichi
• Shirota Naoko
• Suzuki Yusuke
• Jomuta Daisuke

Classifications

• C07C67/10 Primary

  by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond (preparation from carboxylic acid halides C07C67/14) · CPC title

• C07C67/00 Primary

  Preparation of carboxylic acid esters · CPC title

• C07C51/093

  by hydrolysis of —CX3 groups, X being halogen · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title