# US 6,297,407 B1 · Method for producing alkyne diols

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- Number: US 6,297,407 B1
- Document ID: US6297407B1
- Status: Granted
- Kind: B1
- Application number: 09/744,437
- Filed: 2001-01-24
- Granted: 2001-10-02
- Earliest claimed: 1998-08-17
- Assignees: BASF SE
- Inventors: Alois Kindler; Melanie Brunner; Christian Tragut; Jochem Henkelmann
- Web page: https://patentgrep.com/patent/US6297407B1

## CPC

- C07C 29/42: with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The invention relates to a method for producing alkyne diols by reacting ketones with acetylenic hydrocarbons in an organic solvent in the presence of a base which contains potassium alcoholates of primary and/or secondary alcohols. The alkyne diols are produced while forming adducts which precipitate out of the reaction mixture and which are comprised of alkyne monoalcohols and/or alkyne diols and a base. The stoichiometries of the reaction partners are selected such that gelatinous adducts are formed which comprise a spherical surface, whereby the reaction mixture remains agitable during the entire reaction.

## Claims

### Claim 1

In a process for preparing alkynediols by reacting ketones with acetylenic hydrocarbons selected from the group consisting of acetylene and alkynemonool in an organic solvent in the presence of a base comprising potassium alkoxides of primary and/or secondary alcohols to form adducts of alkynemonools and/or alkynediols and said base which precipitate from the reaction mixture, the improvement which comprises, using as acetylenic hydrocarbon acetylene in the ratio of ketone to acetylene from 1.9 to 2.1:1 and the ratio of potassium alkoxide to ketone is within the range from 0.9 to 2.1:1 and using as acetylenic hydrocarbon alkynemonool in the ratio of alkynemonool to ketone from 1:0.8 to 1.2 and the ratio of potassium alkoxide to ketone is within the range from 1.5 to 2.2:1, so as to produce gel like adducts having a spherical surface, whereby the reaction mixture remains stirrable during the entire reaction.

### Claim 2 (depends on 1)

A process as claimed in claim 1, wherein, using as acetylenic hydrocarbon acetylene, it is used in a stoichiometric amount with regard to the ketone and ratio of potassium alkoxide to ketone is within the range from 1:1 to 1.5:1.

### Claim 3 (depends on 2)

A process as claimed in claim 2, wherein the ratio of potassium alkoxide to ketone is within the range from 1.1:1 to 1.3:1.

### Claim 4 (depends on 1)

A process as claimed in claim 1, wherein, using as acetylenic hydrocarbon alkynemonool the ratio of alkynemonool to ketone is within the range from 1:1 and the ratio of potassium alkoxide to ketone is within the range from 1.9:1 to 2.1:1.

### Claim 5 (depends on 1)

a process as claimed in claim 1, wherein ketones selected from acetone, methyl isobutyl ketone and cyclohexanone are used.

### Claim 6 (depends on 5)

A process as claimed in claim 5, wherein acetone is used as ketone.

### Claim 7 (depends on 1)

A process as claimed in claim 1, wherein hydrocarbons are used as solvents.

### Claim 8 (depends on 1)

A process as claimed in claim 1, wherein the potassium alkoxides used are potassium butoxides.