GB1368505A – Preparation of 1,4-diacyloxy-2-butene
– Google Patents
GB1368505A – Preparation of 1,4-diacyloxy-2-butene
– Google Patents
Preparation of 1,4-diacyloxy-2-butene
Info
Publication number
GB1368505A
GB1368505A
GB9372A
GB9372A
GB1368505A
GB 1368505 A
GB1368505 A
GB 1368505A
GB 9372 A
GB9372 A
GB 9372A
GB 9372 A
GB9372 A
GB 9372A
GB 1368505 A
GB1368505 A
GB 1368505A
Authority
GB
United Kingdom
Prior art keywords
butene
diacetoxy
acetoxy
butadiene
acyloxy
Prior art date
1972-01-03
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
GB9372A
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.)
Kuraray Co Ltd
Original Assignee
Kuraray Co Ltd
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.)
1972-01-03
Filing date
1972-01-03
Publication date
1974-09-25
1972-01-03
Application filed by Kuraray Co Ltd
filed
Critical
Kuraray Co Ltd
1972-01-03
Priority to GB9372A
priority
Critical
patent/GB1368505A/en
1974-09-25
Publication of GB1368505A
publication
Critical
patent/GB1368505A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C67/00—Preparation of carboxylic acid esters
C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
Abstract
1368505 1,4 – Diacyloxy – 2 – butenes; 1,4- dihydroxy-2-butene KURARAY CO Ltd 3 Jan 1972 93/72 Heading C2C A method of preparing a 1,4-diacyloxy-2- butene comprises reacting a 1-acyloxy-2- butene or 1-acyloxy-1,3-butadiene with a monocarboxylic acid of the general formula RCOOH, where R is a hydrocarbon radical, and oxygen in the presence of a catalyst containing platinum. An alkali metal salt of a carboxylic acid can be used as a promotor, and may be introduced together with reactants in the gaseous phase or be added to the carboxylic acid in liquid phase reactions. An oxide and/or carboxylate of zinc, titanium, bismuth, cadmium or manganese can be used as reinforcing material for the carrier or as an additional promotor. The 1,4-diacyloxybutene can be hydrolysed to 2-butene-1,4-diol. The 1-acyloxy-1,3-butadiene can be one of the by-products obtained in reacting butadiene with oxygen and a carboxylic acid (to give 1,4- diacyloxy-2-butene main product) and can be isolated before reaction or reacted in the form of a by-product fraction, e.g. of b.pt. 100‹ to 130‹ C. 1-Acyloxy-2-butene and 1-acyloxy-1,3- butadienes by-products from the reaction of nbutenes with oxygen and a carboxylic acid can also be used. The products can be separated by distillation and the content of carboxylic acid, and 1- (and 3-) acyloxy-1-butene be recycled. The 1,4-diacyloxy products can be hydrolysed to the corresponding diols with an acid catalyst, and can be extracted with diisopropyl ether. In examples (1) a mixture of 1-acetoxy-2-butene, acetic acid, oxygen and nitrogen is passed over palladium metal and potassium acetate on alumina at 140‹ C. to give 1,4-diacetoxy-2- butene mixed with some 3,4-diacetoxy-1- butene and 1-acetoxy-1,3-butadiene; (2) 1,4- diacetoxy-2-butene containing 3,4-diacetoxy-1- butene is obtained similarly from 1-acetoxy-1,3- butadiene; (3) from a mixture of butene-1, cis- and trans-butene-2,1-acetoxy-1,3-butadiene a product comprising 1,4 – diacetoxy – 2 – butene, with which 3,4 – diacetoxy – 1 – butene, 3- acetoxy – 1 – butene, 1 – acetoxy – 2 – butene and 1-acetoxy-1,3-butadiene are also formed. The preparation of 2-butene-1,4-diol by the H 2 SO 4 acid catalysed hydrolysis of 1,4-diacetoxy-2-butene is also described, 1-butene-3,4- diol being formed in this reaction also.
GB9372A
1972-01-03
1972-01-03
Preparation of 1,4-diacyloxy-2-butene
Expired
GB1368505A
(en)
Priority Applications (1)
Application Number
Priority Date
Filing Date
Title
GB9372A
GB1368505A
(en)
1972-01-03
1972-01-03
Preparation of 1,4-diacyloxy-2-butene
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
GB9372A
GB1368505A
(en)
1972-01-03
1972-01-03
Preparation of 1,4-diacyloxy-2-butene
Publications (1)
Publication Number
Publication Date
GB1368505A
true
GB1368505A
(en)
1974-09-25
Family
ID=9698282
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB9372A
Expired
GB1368505A
(en)
1972-01-03
1972-01-03
Preparation of 1,4-diacyloxy-2-butene
Country Status (1)
Country
Link
GB
(1)
GB1368505A
(en)
Cited By (7)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US4162363A
(en)
1977-08-25
1979-07-24
Phillips Petroleum Company
Conversion of dienes or monoolefins to diesters
US4164615A
(en)
1977-08-25
1979-08-14
Phillips Petroleum Company
Conversion of conjugated dienes to diacyloxy olefins
US4216119A
(en)
1979-03-01
1980-08-05
Phillips Petroleum Company
Catalyst system comprising elemental sulfur or a sulfur halide for conversion of dienes or monoolefins to diesters
US4242228A
(en)
1979-01-31
1980-12-30
Phillips Petroleum Company
Catalysts for conversion of conjugated diolefins to diacyloxy olefins
US4618704A
(en)
*
1978-05-05
1986-10-21
Basf Aktiengesellschaft
Acyloxy-2-butenes and their preparation
WO1998019983A1
(en)
*
1996-11-08
1998-05-14
Union Carbide Chemicals & Plastics Technology Corporation
Functionalization of hydrocarbyl-containing compounds
CN104292076A
(en)
*
2014-10-11
2015-01-21
江苏常州酞青新材料科技有限公司
Production method of butenediol diacetate
1972
1972-01-03
GB
GB9372A
patent/GB1368505A/en
not_active
Expired
Cited By (7)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US4162363A
(en)
1977-08-25
1979-07-24
Phillips Petroleum Company
Conversion of dienes or monoolefins to diesters
US4164615A
(en)
1977-08-25
1979-08-14
Phillips Petroleum Company
Conversion of conjugated dienes to diacyloxy olefins
US4618704A
(en)
*
1978-05-05
1986-10-21
Basf Aktiengesellschaft
Acyloxy-2-butenes and their preparation
US4242228A
(en)
1979-01-31
1980-12-30
Phillips Petroleum Company
Catalysts for conversion of conjugated diolefins to diacyloxy olefins
US4216119A
(en)
1979-03-01
1980-08-05
Phillips Petroleum Company
Catalyst system comprising elemental sulfur or a sulfur halide for conversion of dienes or monoolefins to diesters
WO1998019983A1
(en)
*
1996-11-08
1998-05-14
Union Carbide Chemicals & Plastics Technology Corporation
Functionalization of hydrocarbyl-containing compounds
CN104292076A
(en)
*
2014-10-11
2015-01-21
江苏常州酞青新材料科技有限公司
Production method of butenediol diacetate
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Legal Events
Date
Code
Title
Description
1975-02-05
PS
Patent sealed
1977-08-03
PLNP
Patent lapsed through nonpayment of renewal fees
