# US 8,785,673 B2 · Method for producing 2-chloroallyl thiocyanate and 2-chloroallyl isothiocyanate

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- Number: US 8,785,673 B2
- Document ID: US8785673B2
- Status: Granted
- Kind: B2
- Application number: 14/113,739
- Filed: 2012-04-24
- Published: 2014-04-17
- Granted: 2014-07-22
- Earliest claimed: 2011-04-26
- Assignees: Bayer Intellectual Property GmbH
- Applicants: Thomas Himmler; Matthias Decker; Ralf Dunkel; Peter Gerdes; Martin Littmann; Norbert Lui; Albert Schnatterer
- Inventors: Thomas Himmler; Matthias Decker; Ralf Dunkel; Peter Gerdes; Martin Littmann; Norbert Lui; Albert Schnatterer
- Web page: https://patentgrep.com/patent/US8785673B2

## CPC

- C07C 331/22: of an unsaturated carbon skeleton
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process is described for producing 2-chloroallyl isothiocyanate from 2,3-dichloro-1-propene by reacting the 2,3-dichloro-1-propene with a thiocyanate in the presence of a phase transfer catalyst, without diluent or in the presence of up to 15 percent by weight based on 2,3-dichloropropene and simultaneously in the presence of an excess of from 10 to 200 mol percent of 2,3-dichloro-1-propene based on the thiocyanate. A process starting from 1,2,3-trichloropropane is also described.

## Claims

### Claim 1

A process for producing 2-chloroallyl isothiocyanate of formula (II),
comprising reacting 2,3-dichloro-1-propene of formula (III),
with a thiocyanate of formula (IV),
M(SCN)n (IV),
in which
M is a metal cation or an ammonium group
and
n is from 1 to 4, as appropriate for a charge number of the cation,
in the presence of a phase transfer catalyst of formula (V),
in which moieties
R1, R2, R3 and R4 are mutually independently hydrogen, C1-C24-alkyl, benzyl or C6-C10-aryl, the latter optionally substituted by halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, C1-C6-dialkylamino, hydroxy or phenyl
and
X is an anion,
without diluent or in the presence of up to 15 percent by weight, based on 2,3-dichloropropene of formula (III) and simultaneously in the presence of an excess of from 10 to 200 mol percent of 2,3-dichloro-1-propene of formula (III) based on a thiocyanate of formula (IV).

### Claim 2 (depends on 1)

The process according to claim 1, wherein the amount used of a diluent is up to 10 percent by weight, based on the 2,3-dichloropropene of formula (III).

### Claim 3 (depends on 1)

The process according to claim 1, where the amount used of a diluent is up to 5 percent by weight, based on the 2,3-dichloropropene of formula (III).

### Claim 4 (depends on 1)

The process according to any of claim 1, where said reacting proceeds at a temperature range from 50 to 100° C.

### Claim 5

A process for producing 2-chloroallyl isothiocyanate of formula (II),
comprising reacting 1,2,3-trichloropropane of formula (VI)
with a base and then reacting resultant 2,3-dichloro-1-propene of formula (III)
with a thiocyanate of formula (IV),
M(SCN)n (IV),
in which
M is a metal cation or an ammonium group
and
n is from 1 to 4, as appropriate for a charge number of the cation,
in the presence of a phase transfer catalyst of formula (V),
in which moieties
R1, R2, R3 and R4 are mutually independently hydrogen, C1-C24-alkyl, benzyl or C6-C10-aryl, the latter optionally substituted by halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, C1-C6-dialkylamino, hydroxy or phenyl
and
X is an anion,
without diluent or in the presence of up to 15 percent by weight, based on 2,3-dichloropropene of formula (III) and simultaneously in the presence of an excess of from 10 to 200 mol percent of 2,3-dichloro-1-propene of formula (III) based on a thiocyanate of formula (IV).

### Claim 6 (depends on 1)

The process according to claim 1, wherein
M is Na+ or NH4+,
n is 1,
R1, R2, R3 and R4 are mutually independently hydrogen, C1-C24-alkyl, benzyl or phenyl
and
X is an anion from the group of chloride, bromide, hydrogensulphate or hydroxide.