GB1432540A

GB1432540A – Process for the preparation of cyclopropane derivatives
– Google Patents

GB1432540A – Process for the preparation of cyclopropane derivatives
– Google Patents
Process for the preparation of cyclopropane derivatives

Info

Publication number
GB1432540A

GB1432540A
GB2291172A
GB2291172A
GB1432540A
GB 1432540 A
GB1432540 A
GB 1432540A
GB 2291172 A
GB2291172 A
GB 2291172A
GB 2291172 A
GB2291172 A
GB 2291172A
GB 1432540 A
GB1432540 A
GB 1432540A
Authority
GB
United Kingdom
Prior art keywords
compound
represent
cyclo
general formula
preparation
Prior art date
1972-05-16
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired

Application number
GB2291172A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Internationale Research Maatschappij BV

Original Assignee
Shell Internationale Research Maatschappij BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
1972-05-16
Filing date
1972-05-16
Publication date
1976-04-22

1972-05-16
Application filed by Shell Internationale Research Maatschappij BV
filed
Critical
Shell Internationale Research Maatschappij BV

1972-05-16
Priority to GB2291172A
priority
Critical
patent/GB1432540A/en

1973-05-10
Priority to IT23933/73A
priority
patent/IT987250B/en

1973-05-14
Priority to IL42255A
priority
patent/IL42255A/en

1973-05-14
Priority to DE2324390A
priority
patent/DE2324390C2/en

1973-05-14
Priority to US359931A
priority
patent/US3917667A/en

1973-05-14
Priority to JP48052669A
priority
patent/JPS593449B2/en

1973-05-14
Priority to NLAANVRAGE7306662,A
priority
patent/NL179045C/en

1973-05-14
Priority to FR7317324A
priority
patent/FR2184793B1/fr

1973-05-14
Priority to CH682573A
priority
patent/CH589016A5/xx

1975-06-17
Priority to US05/587,783
priority
patent/US4008287A/en

1975-06-17
Priority to US05/587,574
priority
patent/US4012430A/en

1976-04-22
Publication of GB1432540A
publication
Critical
patent/GB1432540A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms

C07C31/34—Halogenated alcohols

C07C31/44—Halogenated alcohols containing saturated rings

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C17/00—Preparation of halogenated hydrocarbons

C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C231/00—Preparation of carboxylic acid amides

C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring

C07C29/44—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon double or triple bond

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups

C07C41/01—Preparation of ethers

C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds

C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C67/00—Preparation of carboxylic acid esters

C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond

C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C67/00—Preparation of carboxylic acid esters

C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group

C07C67/297—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C67/00—Preparation of carboxylic acid esters

C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group

C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton

C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C2601/00—Systems containing only non-condensed rings

C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C2601/00—Systems containing only non-condensed rings

C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C2603/00—Systems containing at least three condensed rings

C07C2603/56—Ring systems containing bridged rings

C07C2603/58—Ring systems containing bridged rings containing three rings

C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings

C07C2603/74—Adamantanes

Abstract

1432540 Process for the preparation of cyclopropane derivatives SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ BV 14 May 1973 [16 May 1972] 22911/72 Heading C2C The invention comprises a process for the preparation of gem-dihalocyclopropane derivatives by contacting an aqueous phase containing an alkali metal hydroxide and an organic phase containing both a haloform and an ethylenically unsaturated compound, which reacts with dihalomethylenes generated in situ to form gem-dihalocyclopropanes, said process being effected in the presence of (a) a quaternary onium compound of general Formula I in which X represents P, As or Sb, or if the unsaturated compound is an N-substituted carboxamide or a tertiary alkyl ester of an ethylenically unsaturated carboxylic acid X may also represent N, Y represents OH- or another anion and R1, R2, R3 or R4 each eparately represent hydrocarbyl groups with the proviso that (a) R1, R2, R3 or R4 are not simultaneously aromatic groups and (b) when three of R1, R2, R3 and R4 are aromatic groups Y is I- and/or (b) a quaternary anium compound of general Formula II in which R5, R6 and R7 each represent a (cyclo)alkyl group and Y- is OH- or another anion, and/or (c) a tri(cyclo)alkylonium compound of general Formula III in which R8, R9 and R10 each separately represent a (cyclo)alkyl group, Z represents an S, Se or Te atom, and Y- is OH- or another anion as a catalyst for the in situ generation of a dihalomethylene. The invention also comprises the compound N – 1 – adamantyl – 2,2 – dichloro – 3,3 – dimethylcyclopropanecarboxamide. Reference has been directed by the Comptroller to Specification 1,227,144

GB2291172A
1972-05-16
1972-05-16
Process for the preparation of cyclopropane derivatives

Expired

GB1432540A
(en)

Priority Applications (11)

Application Number
Priority Date
Filing Date
Title

GB2291172A

GB1432540A
(en)

1972-05-16
1972-05-16
Process for the preparation of cyclopropane derivatives

IT23933/73A

IT987250B
(en)

1972-05-16
1973-05-10

PROCESS FOR THE PREPARATION OF CYCLOPROPANE DERIVATIVES

IL42255A

IL42255A
(en)

1972-05-16
1973-05-14
Process for the preparation of gem-dihalo cyclopropane carboxylic acid derivatives and n-1-adamantyl-2,2-dichloro-3,3-dimethylcyclopropane carboxamide

DE2324390A

DE2324390C2
(en)

1972-05-16
1973-05-14

Process for the preparation of derivatives of 2,2-dichloro- or 2,2-dibromocyclopropane

US359931A

US3917667A
(en)

1972-05-16
1973-05-14
Process for preparing gem-dihalocyclopropanecarboxylic acid derivatives

JP48052669A

JPS593449B2
(en)

1972-05-16
1973-05-14

Cyclopropane production

NLAANVRAGE7306662,A

NL179045C
(en)

1972-05-16
1973-05-14

PROCESS FOR THE PREPARATION OF CYCLOPROPAN DERIVATIVES.

FR7317324A

FR2184793B1
(en)

1972-05-16
1973-05-14

CH682573A

CH589016A5
(en)

1972-05-16
1973-05-14

US05/587,783

US4008287A
(en)

1972-05-16
1975-06-17
Process for the preparation of cyclopropane derivatives

US05/587,574

US4012430A
(en)

1972-05-16
1975-06-17
Process for the preparation of cyclopropane derivatives

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

GB2291172A

GB1432540A
(en)

1972-05-16
1972-05-16
Process for the preparation of cyclopropane derivatives

Publications (1)

Publication Number
Publication Date

GB1432540A
true

GB1432540A
(en)

1976-04-22

Family
ID=10187063
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB2291172A
Expired

GB1432540A
(en)

1972-05-16
1972-05-16
Process for the preparation of cyclopropane derivatives

Country Status (9)

Country
Link

US
(1)

US3917667A
(en)

JP
(1)

JPS593449B2
(en)

CH
(1)

CH589016A5
(en)

DE
(1)

DE2324390C2
(en)

FR
(1)

FR2184793B1
(en)

GB
(1)

GB1432540A
(en)

IL
(1)

IL42255A
(en)

IT
(1)

IT987250B
(en)

NL
(1)

NL179045C
(en)

Cited By (2)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

DE2820410A1
(en)

*

1977-05-12
1978-11-16
Shell Int Research

PROCESS FOR THE PRODUCTION OF DIHALOGEN CYCLOPROPANE DERIVATIVES

GB2437726A
(en)

*

2005-12-03
2007-11-07
Bioniqs Ltd
Hydroxylammonium and aloxylammonium compounds and their use as ionic liquids

Families Citing this family (7)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GB1433154A
(en)

1973-11-02
1976-04-22
Shell Int Research
Cyclopropanecarboxylates and their preparation

US4704156A
(en)

*

1986-05-07
1987-11-03
Eli Lilly And Company
Method for plant growth regulation

WO2009077590A1
(en)

*

2007-12-19
2009-06-25
Basf Se
Method for producing 2,2-dichlorocyclopropane carboxylic acid esters

WO2018037999A1
(en)

*

2016-08-25
2018-03-01
日本ゼオン株式会社
Method for converting butenes, and method for purifying monofluorobutane

CN107473250A
(en)

*

2017-08-03
2017-12-15
湖南诺兰蒂尔环保科技有限公司
It is a kind of to be used to purify additive of sodium aluminate solution and preparation method thereof

JP7308081B2
(en)

2019-06-04
2023-07-13
Thk株式会社

Conveyor system

RU2770053C1
(en)

*

2021-03-31
2022-04-14
Федеральное государственное бюджетное образовательное учреждение высшего образования “Уфимский государственный нефтяной технический университет”
Method of producing cis-2,3-hydroxymethyl-gem-dichlorocyclopropane

Family Cites Families (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GB1227144A
(en)

*

1967-04-05
1971-04-07

1972

1972-05-16
GB
GB2291172A
patent/GB1432540A/en
not_active
Expired

1973

1973-05-10
IT
IT23933/73A
patent/IT987250B/en
active

1973-05-14
IL
IL42255A
patent/IL42255A/en
unknown

1973-05-14
FR
FR7317324A
patent/FR2184793B1/fr
not_active
Expired

1973-05-14
CH
CH682573A
patent/CH589016A5/xx
not_active
IP Right Cessation

1973-05-14
US
US359931A
patent/US3917667A/en
not_active
Expired – Lifetime

1973-05-14
JP
JP48052669A
patent/JPS593449B2/en
not_active
Expired

1973-05-14
DE
DE2324390A
patent/DE2324390C2/en
not_active
Expired

1973-05-14
NL
NLAANVRAGE7306662,A
patent/NL179045C/en
not_active
IP Right Cessation

Cited By (3)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

DE2820410A1
(en)

*

1977-05-12
1978-11-16
Shell Int Research

PROCESS FOR THE PRODUCTION OF DIHALOGEN CYCLOPROPANE DERIVATIVES

FR2390411A1
(en)

*

1977-05-12
1978-12-08
Shell Int Research

PREPARATION OF DIHALOGENOCYCLOPROPANE DERIVATIVES

GB2437726A
(en)

*

2005-12-03
2007-11-07
Bioniqs Ltd
Hydroxylammonium and aloxylammonium compounds and their use as ionic liquids

Also Published As

Publication number
Publication date

NL179045C
(en)

1986-07-01

FR2184793B1
(en)

1976-04-23

IT987250B
(en)

1975-02-20

IL42255A0
(en)

1973-07-30

IL42255A
(en)

1978-10-31

DE2324390C2
(en)

1982-09-16

CH589016A5
(en)

1977-06-30

FR2184793A1
(en)

1973-12-28

NL7306662A
(en)

1973-11-20

JPS5062951A
(en)

1975-05-29

DE2324390A1
(en)

1973-11-29

JPS593449B2
(en)

1984-01-24

US3917667A
(en)

1975-11-04

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Legal Events

Date
Code
Title
Description

1976-09-02
PS
Patent sealed [section 19, patents act 1949]

1993-01-13
PCNP
Patent ceased through non-payment of renewal fee

Effective date:
19920514

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