Process for the production of 2-alkyl-3-butyn-2-ols

Patent metadata

Field	Value
Publication number	US-9255050-B2
Application number	US-201414762041-A
Country	US
Kind code	B2
Filing date	Jan 23, 2014
Priority date	Jan 23, 2013
Publication date	Feb 9, 2016
Grant date	Feb 9, 2016

Abstract

The present invention relates to an improved process for the production of 2-alkyl-3-butin-2-ols; especially to a new purification step.

First claim

The invention claimed is:

1. A process for the production of a compound of formula (I)

with R is —CH 3 or —CH 2 CH 3 ,
wherein
i) in a first step, acetone or methylacetone is reacted with ethyne in liquid NH 3 and in the presence of a alkali metal hydroxide as a catalyst, and
ii) in a second step the alkali metal hydroxide catalyst is neutralized by acetic acid, and
iii) in a third step, NH 3 and unreacted starting material and low boiling by-product(s) are removed by distillation, and
iv) in a fourth step, the salts are removed from compound of formula (I) using water and at least one extraction solvent, and
v) in a fifth step, the organic phase comprising the extraction solvent (or mixture of extraction solvents) and compound of formula (I) is separated into its components,

characterized in that after the third step at least an alkali metal hydroxide is added to the solution (=step iiia) before the fourth step is carried out.

2. Process according to claim 1 , wherein R is —CH 3 .

3. Process according to claim 1 , wherein the extraction solvent is MTBE and/or ETBE.

4. Process according to claim 1 , wherein the alkali metal hydroxide catalyst in step i) is KOH or NaOH.

5. Process according to claim 1 , wherein in step iiia) the alkali metal hydroxide is NaOH and/or KOH.

6. Process according to claim 1 , wherein step iiia) is carried out at temperature of 10-45° C.

7. Process according to claim 1 , wherein the alkali metal hydroxide catalyst in step i) is present in catalytic amounts.

8. Process according to claim 1 , wherein alkali metal hydroxide in step iiia) can further be added during step iv).

9. Process according to claim 1 , wherein step iiia) is carried out at normal pressure (1 bar).

Assignees

• Dsm Ip Assets Bv
• Dsm Ip Assets Bv

Inventors

• Tschumi Johannes

Classifications

• C07C33/04

  Acyclic alcohols with carbon-to-carbon triple bonds · CPC title

• C07C29/42 Primary

  with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes · CPC title

• C07C33/042

  with only one triple bond · CPC title

• C07C29/88

  by treatment giving rise to a chemical modification of at least one compound (chemisorption C07C29/76) · CPC title

• C07C33/28

  Alcohols containing only six-membered aromatic rings as cyclic part with unsaturation outside the aromatic rings · CPC title