DE1768412C3 - Verfahren zur Gewinnung von Vinylacetat - Google Patents
Verfahren zur Gewinnung von VinylacetatInfo
- Publication number
- DE1768412C3 DE1768412C3 DE1768412A DE1768412A DE1768412C3 DE 1768412 C3 DE1768412 C3 DE 1768412C3 DE 1768412 A DE1768412 A DE 1768412A DE 1768412 A DE1768412 A DE 1768412A DE 1768412 C3 DE1768412 C3 DE 1768412C3
- Authority
- DE
- Germany
- Prior art keywords
- vinyl acetate
- acetic acid
- water
- product
- acetate
- 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
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 title claims description 72
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 131
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000000047 product Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000007789 gas Substances 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 10
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 238000010533 azeotropic distillation Methods 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000010626 work up procedure Methods 0.000 claims description 2
- 229940093499 ethyl acetate Drugs 0.000 claims 6
- 235000019439 ethyl acetate Nutrition 0.000 claims 6
- -1 500 to 2500 ppm Chemical compound 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 238000005260 corrosion Methods 0.000 claims 1
- 230000007797 corrosion Effects 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 235000015243 ice cream Nutrition 0.000 claims 1
- 230000035699 permeability Effects 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 239000012071 phase Substances 0.000 description 7
- 239000010409 thin film Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- IKUWMXANACQHMT-UHFFFAOYSA-N acetaldehyde;ethyl acetate Chemical compound CC=O.CCOC(C)=O IKUWMXANACQHMT-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- FJOPOOBDMDAVIW-UHFFFAOYSA-N ethenyl acetate;hydrate Chemical compound O.CC(=O)OC=C FJOPOOBDMDAVIW-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/36—Azeotropic distillation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1768412A DE1768412C3 (de) | 1968-05-10 | 1968-05-10 | Verfahren zur Gewinnung von Vinylacetat |
| RO59887A RO55233A (enrdf_load_stackoverflow) | 1968-05-10 | 1969-05-05 | |
| GB23224/69A GB1271104A (en) | 1968-05-10 | 1969-05-07 | Process for working-up crude liquid vinyl acetate |
| LU58600D LU58600A1 (enrdf_load_stackoverflow) | 1968-05-10 | 1969-05-08 | |
| BG012201A BG18854A3 (bg) | 1968-05-10 | 1969-05-08 | Метод за дообработване на суров течен винилацетат |
| CS3269*BA CS150977B2 (enrdf_load_stackoverflow) | 1968-05-10 | 1969-05-08 | |
| DK254969AA DK127184B (da) | 1968-05-10 | 1969-05-09 | Fremgangsmåde til oparbejdning af råt, flydende vinylacetat. |
| NL6907165A NL6907165A (enrdf_load_stackoverflow) | 1968-05-10 | 1969-05-09 | |
| NO1926/69A NO131073C (enrdf_load_stackoverflow) | 1968-05-10 | 1969-05-09 | |
| BE732822D BE732822A (enrdf_load_stackoverflow) | 1968-05-10 | 1969-05-09 | |
| PL1969133449A PL87130B1 (enrdf_load_stackoverflow) | 1968-05-10 | 1969-05-09 | |
| CH715169A CH539598A (de) | 1968-05-10 | 1969-05-09 | Verfahren zur Aufarbeitung von rohem, flüssigem Vinylacetat |
| FR6915119A FR2008280A1 (enrdf_load_stackoverflow) | 1968-05-10 | 1969-05-09 | |
| JP3528269A JPS5411287B1 (enrdf_load_stackoverflow) | 1968-05-10 | 1969-05-09 | |
| BR208673/69A BR6908673D0 (pt) | 1968-05-10 | 1969-05-09 | Processo para elaborar acetato vinilico liquido bruto |
| SE06637/69A SE366023B (enrdf_load_stackoverflow) | 1968-05-10 | 1969-05-09 | |
| ES366991A ES366991A1 (es) | 1968-05-10 | 1969-05-09 | Procedimiento para la elaboracion de acetato de vinilo li- quido. |
| AT446269A AT292651B (de) | 1968-05-10 | 1969-05-09 | Verfahren zur Aufarbeitung von rohem, flüssigem Vinylacetat |
| US235089A US3905875A (en) | 1968-05-10 | 1972-03-15 | Process for the purification of crude liquid vinyl acetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1768412A DE1768412C3 (de) | 1968-05-10 | 1968-05-10 | Verfahren zur Gewinnung von Vinylacetat |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1768412A1 DE1768412A1 (de) | 1971-09-30 |
| DE1768412B2 DE1768412B2 (de) | 1973-11-15 |
| DE1768412C3 true DE1768412C3 (de) | 1974-06-06 |
Family
ID=5699737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1768412A Expired DE1768412C3 (de) | 1968-05-10 | 1968-05-10 | Verfahren zur Gewinnung von Vinylacetat |
Country Status (18)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2945913A1 (de) * | 1979-11-14 | 1981-06-04 | Hoechst Ag, 6000 Frankfurt | Verfahren zur abtrennung von wasser aus gemischen mit vinylacetat und essigsaeure |
| GB9821970D0 (en) * | 1998-10-08 | 1998-12-02 | Bp Chem Int Ltd | Process for purifying a process system |
| DE102010001097A1 (de) | 2010-01-21 | 2011-07-28 | Wacker Chemie AG, 81737 | Verfahren zur Herstellung von Vinylacetat |
| US8884052B2 (en) | 2011-12-15 | 2014-11-11 | Celanese International Corporation | Production of diacetoxyethylene by direct acetoxylation |
| JP7237239B2 (ja) * | 2019-08-05 | 2023-03-10 | ライオンデルバーゼル・アセチルズ・エルエルシー | Ｖａｍ生成時における酢酸エチルの除去 |
-
1968
- 1968-05-10 DE DE1768412A patent/DE1768412C3/de not_active Expired
-
1969
- 1969-05-05 RO RO59887A patent/RO55233A/ro unknown
- 1969-05-07 GB GB23224/69A patent/GB1271104A/en not_active Expired
- 1969-05-08 CS CS3269*BA patent/CS150977B2/cs unknown
- 1969-05-08 LU LU58600D patent/LU58600A1/xx unknown
- 1969-05-08 BG BG012201A patent/BG18854A3/xx unknown
- 1969-05-09 AT AT446269A patent/AT292651B/de not_active IP Right Cessation
- 1969-05-09 CH CH715169A patent/CH539598A/de not_active IP Right Cessation
- 1969-05-09 ES ES366991A patent/ES366991A1/es not_active Expired
- 1969-05-09 PL PL1969133449A patent/PL87130B1/pl unknown
- 1969-05-09 JP JP3528269A patent/JPS5411287B1/ja active Pending
- 1969-05-09 NO NO1926/69A patent/NO131073C/no unknown
- 1969-05-09 SE SE06637/69A patent/SE366023B/xx unknown
- 1969-05-09 BE BE732822D patent/BE732822A/xx unknown
- 1969-05-09 DK DK254969AA patent/DK127184B/da unknown
- 1969-05-09 FR FR6915119A patent/FR2008280A1/fr not_active Withdrawn
- 1969-05-09 NL NL6907165A patent/NL6907165A/xx unknown
- 1969-05-09 BR BR208673/69A patent/BR6908673D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE366023B (enrdf_load_stackoverflow) | 1974-04-08 |
| DE1768412B2 (de) | 1973-11-15 |
| CH539598A (de) | 1973-07-31 |
| LU58600A1 (enrdf_load_stackoverflow) | 1969-08-22 |
| ES366991A1 (es) | 1971-06-16 |
| PL87130B1 (enrdf_load_stackoverflow) | 1976-06-30 |
| NL6907165A (enrdf_load_stackoverflow) | 1969-11-12 |
| DE1768412A1 (de) | 1971-09-30 |
| RO55233A (enrdf_load_stackoverflow) | 1973-07-20 |
| AT292651B (de) | 1971-09-10 |
| NO131073C (enrdf_load_stackoverflow) | 1975-04-02 |
| CS150977B2 (enrdf_load_stackoverflow) | 1973-09-17 |
| NO131073B (enrdf_load_stackoverflow) | 1974-12-23 |
| DK127184B (da) | 1973-10-01 |
| GB1271104A (en) | 1972-04-19 |
| BG18854A3 (bg) | 1975-03-20 |
| BR6908673D0 (pt) | 1973-01-25 |
| JPS5411287B1 (enrdf_load_stackoverflow) | 1979-05-14 |
| FR2008280A1 (enrdf_load_stackoverflow) | 1970-01-16 |
| BE732822A (enrdf_load_stackoverflow) | 1969-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |