GB827718A - Improvements in or relating to the manufacture of vinyl esters - Google Patents
Improvements in or relating to the manufacture of vinyl estersInfo
- Publication number
- GB827718A GB827718A GB320055A GB320055A GB827718A GB 827718 A GB827718 A GB 827718A GB 320055 A GB320055 A GB 320055A GB 320055 A GB320055 A GB 320055A GB 827718 A GB827718 A GB 827718A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ester
- acetate
- mercuric
- vinyl
- acid
- 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
- 229920001567 vinyl ester resin Polymers 0.000 title abstract 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- UKMSUNONTOPOIO-UHFFFAOYSA-N Behenic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 abstract 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 abstract 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 2
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 2
- AOHAPDDBNAPPIN-UHFFFAOYSA-N myristicinic acid Natural products COC1=CC(C(O)=O)=CC2=C1OCO2 AOHAPDDBNAPPIN-UHFFFAOYSA-N 0.000 abstract 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N n-Decanedioic acid Natural products OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 abstract 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000004359 castor oil Substances 0.000 abstract 1
- 235000019438 castor oil Nutrition 0.000 abstract 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000000944 linseed oil Substances 0.000 abstract 1
- 235000021388 linseed oil Nutrition 0.000 abstract 1
- 150000002730 mercury Chemical class 0.000 abstract 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Vinyl esters are prepared by a process comprising effecting an ester-interchange between a vinyl ester of a low molecular weight carboxylic acid having 1 to 4 carbon atoms and a carboxylic acid containing 3 to 26 carbon atoms of higher molecular weight by reacting the ester and acid together in the presence of a mercury salt of an aromatic sulphonic acid; preferably, there is used a mercuric salt which, if desired, may be formed in situ from mercuric acetate and the sulphonic acid. The catalyst may be added in stages and the original vinyl ester is preferably used in excess. Reaction may be effected at below room temperature up to the boiling point of the reaction mixture but preferably below 60 DEG C. Use of the lower temperatures avoids formation of ethylidene diester-type by-products. Their formation is also reduced by terminating the reaction at the optimum point, for example, by addition of sodium acetate. Polymerization inhibitors, e.g. copper acetate, may be present. The resulting esters may be homoor polymerized. Examples describe ester-interchange between vinyl acetate and capric, caprylic, benzoic, lauric, myristic, adipic, sebacic, behenic, stearic or pyro mellitic acid or distilled linseed oil or dehydrated castor oil fatty acids, the catalyst being mercuric toluene sulphonate or naphthalene-2-sulphonate which sometimes is formed in situ. U.S.A. Specification 2,299,862 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB320055A GB827718A (en) | 1955-02-03 | 1955-02-03 | Improvements in or relating to the manufacture of vinyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB320055A GB827718A (en) | 1955-02-03 | 1955-02-03 | Improvements in or relating to the manufacture of vinyl esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB827718A true GB827718A (en) | 1960-02-10 |
Family
ID=9753841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB320055A Expired GB827718A (en) | 1955-02-03 | 1955-02-03 | Improvements in or relating to the manufacture of vinyl esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB827718A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287294A (en) * | 1961-12-11 | 1966-11-22 | Soto Chemical Coatings Inc De | Alkylolated acrylamide interpolymers comprising vinyl stearate |
| US5155253A (en) * | 1988-06-30 | 1992-10-13 | Union Carbide Chemicals & Plastics Technology Corporation | Transvinylation process for the preparation of thermally labile vinyl compounds and for vinyl compounds prepared from thermally labile acids |
| US5210207A (en) * | 1991-01-31 | 1993-05-11 | Union Carbide Chemicals & Plastics Technology Corporation | Transvinylation process by reactive distillation |
| WO2007060176A1 (en) * | 2005-11-23 | 2007-05-31 | Basf Se | Process for preparing vinyl carboxylates |
| DE102014210835A1 (en) | 2014-06-06 | 2015-12-17 | Wacker Chemie Ag | Process for the separation of high-boiling carboxylic acid vinyl ester / carboxylic acid mixtures |
-
1955
- 1955-02-03 GB GB320055A patent/GB827718A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287294A (en) * | 1961-12-11 | 1966-11-22 | Soto Chemical Coatings Inc De | Alkylolated acrylamide interpolymers comprising vinyl stearate |
| US5155253A (en) * | 1988-06-30 | 1992-10-13 | Union Carbide Chemicals & Plastics Technology Corporation | Transvinylation process for the preparation of thermally labile vinyl compounds and for vinyl compounds prepared from thermally labile acids |
| US5210207A (en) * | 1991-01-31 | 1993-05-11 | Union Carbide Chemicals & Plastics Technology Corporation | Transvinylation process by reactive distillation |
| WO2007060176A1 (en) * | 2005-11-23 | 2007-05-31 | Basf Se | Process for preparing vinyl carboxylates |
| US8044233B2 (en) | 2005-11-23 | 2011-10-25 | Basf Aktiengesellschaft | Process for preparing vinyl carboxylates |
| DE102014210835A1 (en) | 2014-06-06 | 2015-12-17 | Wacker Chemie Ag | Process for the separation of high-boiling carboxylic acid vinyl ester / carboxylic acid mixtures |
| US9822059B2 (en) | 2014-06-06 | 2017-11-21 | Wacker Chemie Ag | Method for separating high-boiling carboxylic acid vinyl ester/carboxylic acid mixtures |
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