# US 2021/0276935 A1 · Ethynylation of polyunsaturated aldehydes and ketones

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- Number: US 2021/0276935 A1
- Document ID: US20210276935A1
- Status: Published application
- Kind: A1
- Application number: 17/331,328
- Filed: 2021-05-26
- Published: 2021-09-09
- Earliest claimed: 2014-10-16
- Assignees: Dsm IP Assets B.V.
- Applicants: Dsm IP Assets B.V.
- Inventors: Werner BONRATH; Jan SCHUETZ; Thomas NETSCHER; Bettina WUESTENBERG
- Web page: https://patentgrep.com/patent/US20210276935A1

## CPC

- C07C 29/42: with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
- C07C 29/38: by reaction with aldehydes or ketones
- C07C 403/08: by hydroxy groups
- C07C 2601/16: the ring being unsaturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to a catalytic process for the ethynylation of specific polyunsaturated aldehydes and ketones.

## Claims

### Claim 1

A catalytic ethynylation process which comprises conducting a catalytic ethinylation reaction of a compound of formula (I):
wherein
R1 signifies —H or —CH3,
R2 signifies —H, and
R3 signifies a moiety selected from the group consisting of:
with ethyne in NH3 as a solvent and in the presence of a catalyst of formula ROH, wherein R signifies K or Cs at a catalytic ethinylation reaction temperature between −40° C. to 10° C.

### Claim 2 (depends on 1)

The catalytic ethynylation process according to claim 1, wherein the compound of formula (I) is a compound of formula (Ia):

### Claim 3 (depends on 1)

The catalytic ethynylation process according to claim 1, wherein the compound of formula (I) is a compound of formula (Ib):

### Claim 4 (depends on 1)

The catalytic ethynylation process according to claim 1, wherein the compound of formula (I) is a compound of formula (Ic):

### Claim 5 (depends on 1)

The catalytic ethynylation process according to claim 1, wherein the catalyst is added to the reaction mixture as an aqueous solution.

### Claim 6 (depends on 1)

The catalytic ethynylation process according to claim 1, wherein R is K.

### Claim 7 (depends on 1)

The catalytic ethynylation process according to claim 1, wherein the catalytic ethynylation reaction is carried out under pressure which is in a range from 2 bar to 15 bar.

### Claim 8 (depends on 1)

The catalytic ethynylation process according to claim 1, wherein the catalytic ethynylation reaction temperature is between −30° to 5° C.

### Claim 9 (depends on 1)

The catalytic ethinylation process according to claim 1, wherein the catalytic ethynylation reaction is carried out under pressure which is in a range of 5 bar to 12 bar.

### Claim 10 (depends on 1)

The catalytic ethinylation process according to claim 1, wherein the catalytic ethynylation reaction is carried out under pressure which is in a range of 6 bar to 10 bar.