DE1768289C3 - Verfahren zur Herstellung von Vinylestern, gesättigter Monocarbonsäuren bzw. von Gemischen solcher Ester - Google Patents
Verfahren zur Herstellung von Vinylestern, gesättigter Monocarbonsäuren bzw. von Gemischen solcher EsterInfo
- Publication number
- DE1768289C3 DE1768289C3 DE1768289A DE1768289A DE1768289C3 DE 1768289 C3 DE1768289 C3 DE 1768289C3 DE 1768289 A DE1768289 A DE 1768289A DE 1768289 A DE1768289 A DE 1768289A DE 1768289 C3 DE1768289 C3 DE 1768289C3
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- carboxylic acid
- liquid
- vessel
- mixture
- 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
- 239000000203 mixture Substances 0.000 title claims description 34
- 229920001567 vinyl ester resin Polymers 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 14
- 150000002148 esters Chemical class 0.000 title claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 6
- 150000002763 monocarboxylic acids Chemical class 0.000 title claims description 5
- 229920006395 saturated elastomer Polymers 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 238000002156 mixing Methods 0.000 claims description 23
- 150000001735 carboxylic acids Chemical class 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 16
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 14
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 230000007420 reactivation Effects 0.000 claims description 11
- 239000012429 reaction media Substances 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003752 zinc compounds Chemical class 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 31
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 150000003751 zinc Chemical class 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- -1 saturated aliphatic monocarboxylic acids Chemical class 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000009471 action Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 2
- 229940007718 zinc hydroxide Drugs 0.000 description 2
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB19376/67A GB1125055A (en) | 1967-04-27 | 1967-04-27 | Improvements in or relating to the preparation of vinyl esters |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1768289A1 DE1768289A1 (de) | 1971-11-18 |
| DE1768289B2 DE1768289B2 (de) | 1977-10-27 |
| DE1768289C3 true DE1768289C3 (de) | 1978-06-29 |
Family
ID=10128326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1768289A Expired DE1768289C3 (de) | 1967-04-27 | 1968-04-25 | Verfahren zur Herstellung von Vinylestern, gesättigter Monocarbonsäuren bzw. von Gemischen solcher Ester |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3607915A (enExample) |
| BE (1) | BE714224A (enExample) |
| DE (1) | DE1768289C3 (enExample) |
| FR (1) | FR1561735A (enExample) |
| GB (1) | GB1125055A (enExample) |
| NL (1) | NL158478B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4091005A (en) * | 1976-10-04 | 1978-05-23 | The United States Of America As Represented By The Secretary Of Agriculture | Continuous process for preparation of isopropenyl stearate |
| DE4313922A1 (de) * | 1993-04-28 | 1994-11-03 | Basf Ag | Verfahren zur Herstellung von Carbonsäurevinylestern |
| US5430179A (en) * | 1994-07-28 | 1995-07-04 | Union Carbide Chemicals & Plastics Technology | Homogeneous process for the ruthenium catalyzed addition of carboxylic acids to alkynes |
| ZA979132B (en) | 1996-10-15 | 1998-07-17 | Shell Int Research | A process for the preparation of vinylesters |
| US6891052B1 (en) | 1997-10-31 | 2005-05-10 | Exxonmobil Chemical Patents Inc. | Process for forming vinyl ester from carboxylic acid with water treatment of the reaction mixture |
| DE19925385A1 (de) * | 1999-06-02 | 2000-12-07 | Oxeno Olefinchemie Gmbh | Verfahren zur katalytischen Durchführung von Mehrphasenreaktionen, insbesondere Vinylierungen von Carbonsäuren |
| JP5145237B2 (ja) * | 2005-11-23 | 2013-02-13 | ビーエーエスエフ ソシエタス・ヨーロピア | カルボン酸ビニルエステルの製造方法 |
| JP5453247B2 (ja) * | 2007-05-16 | 2014-03-26 | ビーエーエスエフ ソシエタス・ヨーロピア | カルボン酸ビニルエステルの製造法 |
| US8173830B2 (en) * | 2009-05-07 | 2012-05-08 | Celanese International Corporation | Vinyl ester production from acetylene and carboxylic acid utilizing homogeneous catalyst |
| US7982065B2 (en) * | 2009-05-07 | 2011-07-19 | Celanese International Corporation | Vinyl ester production from acetylene and carboxylic acid utilizing heterogeneous catalyst |
| CN102617344B (zh) * | 2012-03-09 | 2014-04-16 | 天津市沃克玛特科技有限公司 | 羧酸乙烯酯的制备方法 |
-
1967
- 1967-04-27 GB GB19376/67A patent/GB1125055A/en not_active Expired
-
1968
- 1968-04-08 US US719714A patent/US3607915A/en not_active Expired - Lifetime
- 1968-04-25 FR FR1561735D patent/FR1561735A/fr not_active Expired
- 1968-04-25 DE DE1768289A patent/DE1768289C3/de not_active Expired
- 1968-04-25 BE BE714224D patent/BE714224A/xx unknown
- 1968-04-25 NL NL6805844.A patent/NL158478B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL6805844A (enExample) | 1968-10-28 |
| US3607915A (en) | 1971-09-21 |
| GB1125055A (en) | 1968-08-28 |
| FR1561735A (enExample) | 1969-03-28 |
| BE714224A (enExample) | 1968-10-25 |
| DE1768289B2 (de) | 1977-10-27 |
| DE1768289A1 (de) | 1971-11-18 |
| NL158478B (nl) | 1978-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |