GB1368505A - Preparation of 1,4-diacyloxy-2-butene - Google Patents
Preparation of 1,4-diacyloxy-2-buteneInfo
- 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
- 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
Links
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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.
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)
| 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)
| 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 |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |