Method for producing diol

Patent metadata

Field	Value
Publication number	US-10717693-B2
Application number	US-201615777494-A
Country	US
Kind code	B2
Filing date	Nov 22, 2016
Priority date	Nov 24, 2015
Publication date	Jul 21, 2020
Grant date	Jul 21, 2020

Abstract

The present invention provides a method for producing a diol having a specific structure in high yields while keeping high selectivity. Provided is a method for producing a diol having a specific structure by oxidizing an olefin having a specific structure in the presence of a ruthenium compound.

First claim

The invention claimed is:

1. A method for producing a diol in high yields, comprising
oxidizing an olefin represented by Formula (1):

wherein R 1 is a group having an electronegativity of 3.3 to 5.0; and R 2 to R 4 are each independently a hydrogen atom, a cyano group, or an optionally substituted alkyl group, in the presence of a ruthenium compound to produce a diol represented by Formula (2):

wherein R 1 to R 4 are as defined above.

2. The production method according to claim 1 ,
wherein one of R 2 to R 4 is a hydrogen atom.

3. The production method according to claim 1 ,
wherein two of R 2 to R 4 are hydrogen atoms.

4. The production method according to claim 1 ,
wherein R 2 to R 4 are all hydrogen atoms.

5. The production method according to claim 1 , further comprising collecting the ruthenium compound after the oxidization of the olefin.

6. A method for producing a diol in high yields, comprising
oxidizing an olefin represented by Formula (3):

wherein R 5 is a cyano group or a fluorine-containing alkyl group; and R 6 to R 8 are each independently a hydrogen atom, a cyano group, or an optionally substituted alkyl group, in the presence of a ruthenium compound to produce a diol represented by Formula (4):

wherein R 5 to R 8 are as defined above.

7. The production method according to claim 6 ,
wherein one of R 6 to R 8 is a hydrogen atom.

8. The production method according to claim 6 ,
wherein two of R 6 to R 8 are hydrogen atoms.

9. The production method according to claim 6 ,
wherein R 6 to R 8 are all hydrogen atoms.

10. The production method according to claim 6 , further comprising collecting the ruthenium compound after the oxidization of the olefin.

11. A composition comprising:
a diol represented by Formula (4):

wherein R 5 is a cyano group or a fluorine-containing alkyl group; and R 6 to R 8 are each independently a hydrogen atom, a cyano group, or an optionally substituted alkyl group, and
an acid compound represented by Formula (5):
R 5 —COOH

wherein R 5 is as defined above,
the composition containing the acid compound in an amount of 1,000 to 10,000 ppm.

Assignees

• Daikin Ind Ltd

Inventors

• Hamada Tomohito
• Okada Michiaki
• Yamamoto Akinori
• Kishikawa Yosuke

Classifications

• C07C255/12

  containing cyano groups and hydroxy groups bound to the carbon skeleton · CPC title

• C07C253/30

  by reactions not involving the formation of cyano groups · CPC title

• C07C31/42

  Polyhydroxylic acyclic alcohols · CPC title

• C07C29/48 Primary

  by oxidation reactions with formation of hydroxy groups · CPC title

• C07B61/00

  Other general methods · CPC title