GB1070323A

GB1070323A – Process for the preparation of epsilon-caprolactones
– Google Patents

GB1070323A – Process for the preparation of epsilon-caprolactones
– Google Patents
Process for the preparation of epsilon-caprolactones

Info

Publication number
GB1070323A

GB1070323A
GB3002/67A
GB300267A
GB1070323A
GB 1070323 A
GB1070323 A
GB 1070323A
GB 3002/67 A
GB3002/67 A
GB 3002/67A
GB 300267 A
GB300267 A
GB 300267A
GB 1070323 A
GB1070323 A
GB 1070323A
Authority
GB
United Kingdom
Prior art keywords
hydrogen peroxide
caprolactones
formic acid
cyclohexanone
formula
Prior art date
1963-04-24
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
GB3002/67A
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.)

Ugine Kuhlmann SA

Original Assignee
Ugine Kuhlmann SA
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.)
1963-04-24
Filing date
1964-04-24
Publication date
1967-06-01

1964-04-24
Application filed by Ugine Kuhlmann SA
filed
Critical
Ugine Kuhlmann SA

1967-06-01
Publication of GB1070323A
publication
Critical
patent/GB1070323A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 – C07D313/00

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides

C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation

C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C67/00—Preparation of carboxylic acid esters

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C67/00—Preparation of carboxylic acid esters

C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds

Abstract

e -Caprolactones of the formula are made by contacting a cyclohexanone of the formula where R represents hydrogen or an alkyl or cycloalkyl group, with a pre-formed solution of hydrogen peroxide and formic acid in the absence of a catalyst at 0 DEG to 40 DEG C., in the proportion of at least 1 mol formic acid per mol hydrogen peroxide, the molar ration of hydrogen peroxide/cyclohexanone being between 0.1 and 2. A small proportion of crystalline cyclic peroxides may form in the reaction mixture. It is preferred to allow the mixture of hydrogen peroxide and formic acid to stand for sufficient time for 20-80% of the hydrogen peroxide to be converted to performic acid. The caprolactones are separated from the reaction mixture at temperatures below 40 DEG C., e.g. by using thin film distillation or solvent extraction. Examples are provided.

GB3002/67A
1963-04-24
1964-04-24
Process for the preparation of epsilon-caprolactones

Expired

GB1070323A
(en)

Applications Claiming Priority (3)

Application Number
Priority Date
Filing Date
Title

FR932506A

FR1368139A
(en)

1963-04-24
1963-04-24

Process for the preparation of derivatives of 6-hydroxy caproic acids

FR955886A

FR1385557A
(en)

1963-04-24
1963-12-03

Process for preparing epsilon-caprolactones

FR48652A

FR89911E
(en)

1963-04-24
1966-02-07

Process for preparing epsilon-caprolactones

Publications (1)

Publication Number
Publication Date

GB1070323A
true

GB1070323A
(en)

1967-06-01

Family
ID=27242879
Family Applications (3)

Application Number
Title
Priority Date
Filing Date

GB3002/67A
Expired

GB1070323A
(en)

1963-04-24
1964-04-24
Process for the preparation of epsilon-caprolactones

GB17147/64A
Expired

GB1070322A
(en)

1963-04-24
1964-04-24
Process for the preparation of 6-formyloxy caproic acids and derivatives thereof

GB4954/67A
Expired

GB1124872A
(en)

1963-04-24
1967-02-07
Process for the preparation of epsilon-caprolactones

Family Applications After (2)

Application Number
Title
Priority Date
Filing Date

GB17147/64A
Expired

GB1070322A
(en)

1963-04-24
1964-04-24
Process for the preparation of 6-formyloxy caproic acids and derivatives thereof

GB4954/67A
Expired

GB1124872A
(en)

1963-04-24
1967-02-07
Process for the preparation of epsilon-caprolactones

Country Status (8)

Country
Link

US
(1)

US3428656A
(en)

BE
(2)

BE646938A
(en)

CH
(2)

CH439251A
(en)

DE
(2)

DE1216283C2
(en)

FR
(3)

FR1368139A
(en)

GB
(3)

GB1070323A
(en)

LU
(2)

LU45884A1
(en)

NL
(2)

NL145237B
(en)

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US11820737B2
(en)

2020-01-31
2023-11-21
Ecolab Usa Inc.
Generation of peroxyhydroxycarboxylic acid and the use thereof

Families Citing this family (16)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GB1144127A
(en)

*

1965-08-28
1969-03-05
Distillers Co Yeast Ltd
Acyloxy-alkane carboxylic acids

GB1203752A
(en)

*

1966-09-30
1970-09-03
Laporte Chemical
Preparation of lactones

FR1604718A
(en)

*

1968-10-22
1972-01-24

CH505630A
(en)

*

1969-11-10
1971-04-15
Gertsch Ernst

Safety ski binding

US3888878A
(en)

*

1970-12-24
1975-06-10
Uniroyal Inc
Method of making 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxamide 4,4-dioxides

FR2231651B1
(en)

*

1973-06-04
1976-04-23
Rhone Poulenc Ind

FR2329634A2
(en)

*

1973-06-04
1977-05-27
Rhone Poulenc Ind

NEW ACYLOXYALCANALS

AT332362B
(en)

*

1974-10-10
1976-09-27
Erz & Stahl Ges M B H

PROCESS FOR THE EXTRACTION OF MONOCARBON REESTERS AND DICARBON ACIDS OR THEIR ESTERS FROM THE WASTE SALINE SOLUTIONS FROM CYCLOHEXANONE PRODUCTION

US4171313A
(en)

*

1977-10-14
1979-10-16
Allied Chemical Corporation
Molybdenum and tungsten peroxo complexes useful as oxidation catalysts

US4160769A
(en)

*

1977-12-12
1979-07-10
Union Carbide Corporation
Oxidation of ketones to esters

US4183863A
(en)

*

1978-04-18
1980-01-15
Union Carbide Corporation
Conversion of cyclohexanol to ε-caprolactone

FR2519985A1
(en)

*

1982-01-15
1983-07-22
Ugine Kuhlmann

IMPROVED PROCESS FOR THE MANUFACTURE OF E-CAPROLACTONE

US4870192A
(en)

*

1985-08-12
1989-09-26
Mobil Oil Corporation
Production of lactones and omega-hydroxycarboxylic acids

EP1121980B1
(en)

*

2000-01-31
2007-04-11
SOLVAY (Société Anonyme)
Process of oxidation with a catalyst comprising a composition of antimony trifluoride and silica

GB2512836A
(en)

*

2013-04-08
2014-10-15
Givaudan Sa
Novel process

GB2548137A
(en)

*

2016-03-09
2017-09-13
Perstorp Ab
Production equipment (I) for production of a caprolactone

Family Cites Families (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3064008A
(en)

*

1962-11-13

I i i i i i

1963

1963-04-24
FR
FR932506A
patent/FR1368139A/en
not_active
Expired

1963-12-03
FR
FR955886A
patent/FR1385557A/en
not_active
Expired

1964

1964-04-16
LU
LU45884D
patent/LU45884A1/xx
unknown

1964-04-20
DE
DE1964S0090633
patent/DE1216283C2/en
not_active
Expired

1964-04-23
BE
BE646938D
patent/BE646938A/xx
unknown

1964-04-24
GB
GB3002/67A
patent/GB1070323A/en
not_active
Expired

1964-04-24
GB
GB17147/64A
patent/GB1070322A/en
not_active
Expired

1964-04-24
NL
NL646404543A
patent/NL145237B/en
unknown

1964-04-24
CH
CH536764A
patent/CH439251A/en
unknown

1966

1966-02-07
FR
FR48652A
patent/FR89911E/en
not_active
Expired

1967

1967-01-25
BE
BE693132D
patent/BE693132A/xx
unknown

1967-01-25
DE
DE1967U0013490
patent/DE1643146B2/en
active
Granted

1967-02-02
LU
LU52927D
patent/LU52927A1/xx
unknown

1967-02-02
NL
NL6701618A
patent/NL6701618A/xx
unknown

1967-02-06
US
US614014A
patent/US3428656A/en
not_active
Expired – Lifetime

1967-02-07
CH
CH175567A
patent/CH475235A/en
not_active
IP Right Cessation

1967-02-07
GB
GB4954/67A
patent/GB1124872A/en
not_active
Expired

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US11820737B2
(en)

2020-01-31
2023-11-21
Ecolab Usa Inc.
Generation of peroxyhydroxycarboxylic acid and the use thereof

Also Published As

Publication number
Publication date

GB1124872A
(en)

1968-08-21

FR1368139A
(en)

1964-07-31

NL6701618A
(en)

1967-08-08

CH439251A
(en)

1967-07-15

DE1643146A1
(en)

1971-07-15

FR89911E
(en)

1967-09-08

US3428656A
(en)

1969-02-18

FR1385557A
(en)

1965-01-15

CH475235A
(en)

1969-07-15

GB1070322A
(en)

1967-06-01

LU45884A1
(en)

1964-07-03

DE1643146B2
(en)

1976-09-23

DE1216283C2
(en)

1976-05-20

BE646938A
(en)

1964-08-17

DE1216283B
(en)

1966-05-12

LU52927A1
(en)

1967-04-03

NL145237B
(en)

1975-03-17

NL6404543A
(en)

1964-10-26

BE693132A
(en)

1967-07-03

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Process for the preparation of epsilon-caprolactones

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