DE1278430B - - Google Patents
Info
- Publication number
- DE1278430B DE1278430B DE19671278430 DE1278430A DE1278430B DE 1278430 B DE1278430 B DE 1278430B DE 19671278430 DE19671278430 DE 19671278430 DE 1278430 A DE1278430 A DE 1278430A DE 1278430 B DE1278430 B DE 1278430B
- Authority
- DE
- Germany
- Prior art keywords
- column
- carboxylic acid
- acetic acid
- vinyl ester
- 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.)
- Granted
Links
- 239000007789 gas Substances 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 30
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 23
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 20
- 239000005977 Ethylene Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 229920001567 vinyl ester resin Polymers 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 229910001868 water Inorganic materials 0.000 claims description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 131
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 20
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 238000004821 distillation Methods 0.000 description 8
- 239000001569 carbon dioxide Substances 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000006886 vinylation reaction Methods 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000012495 reaction gas Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- IZTAJSDUQOESIR-UHFFFAOYSA-H [C+4].C(C)(=O)[O-].[Zn+2].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-] Chemical compound [C+4].C(C)(=O)[O-].[Zn+2].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-] IZTAJSDUQOESIR-UHFFFAOYSA-H 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FJOPOOBDMDAVIW-UHFFFAOYSA-N ethenyl acetate;hydrate Chemical compound O.CC(=O)OC=C FJOPOOBDMDAVIW-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical compound [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- -1 hydrocarbon radical Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/08—Acetic acid
-
- 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
-
- 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
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 (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671278430 DE1278430C2 (de) | 1967-02-25 | 1967-02-25 | Verfahren zur abtrennung der mischung eines vinylesters im molaren ueberschuss mit der entsprechenden carbonsaeure |
| NL6801778A NL6801778A (enEXAMPLES) | 1967-02-25 | 1968-02-08 | |
| CH259868A CH490312A (de) | 1967-02-25 | 1968-02-22 | Verfahren zur Gewinnung eines angereicherten Vinylesters aus heissen Gasgemischen |
| BE711270D BE711270A (enEXAMPLES) | 1967-02-25 | 1968-02-26 | |
| FR1555178D FR1555178A (enEXAMPLES) | 1967-02-25 | 1968-02-26 | |
| GB916168A GB1193537A (en) | 1967-02-25 | 1968-02-26 | Process for Separating a Vinyl Ester from Hot Reaction Gases Containing the Carboxylic Acid on which the Ester is Based. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671278430 DE1278430C2 (de) | 1967-02-25 | 1967-02-25 | Verfahren zur abtrennung der mischung eines vinylesters im molaren ueberschuss mit der entsprechenden carbonsaeure |
| DEF0051640 | 1967-02-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1278430C2 DE1278430C2 (de) | 1974-05-30 |
| DE1278430B true DE1278430B (enEXAMPLES) | 1974-05-30 |
Family
ID=25751581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671278430 Expired DE1278430C2 (de) | 1967-02-25 | 1967-02-25 | Verfahren zur abtrennung der mischung eines vinylesters im molaren ueberschuss mit der entsprechenden carbonsaeure |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE711270A (enEXAMPLES) |
| CH (1) | CH490312A (enEXAMPLES) |
| DE (1) | DE1278430C2 (enEXAMPLES) |
| FR (1) | FR1555178A (enEXAMPLES) |
| GB (1) | GB1193537A (enEXAMPLES) |
| NL (1) | NL6801778A (enEXAMPLES) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005036930A1 (de) * | 2005-08-05 | 2007-02-08 | Celanese Chemicals Europe Gmbh | Verfahren zur Isolierung von Vinylacetat |
| DE102016205487A1 (de) | 2016-04-04 | 2017-10-05 | Wacker Chemie Ag | Verfahren zur Herstellung von Vinylacetat |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2610624C2 (de) * | 1976-03-13 | 1985-02-14 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Gewinnung von Vinylacetat aus den Gasgemischen, die bei dessen Herstellung anfallen |
-
1967
- 1967-02-25 DE DE19671278430 patent/DE1278430C2/de not_active Expired
-
1968
- 1968-02-08 NL NL6801778A patent/NL6801778A/xx unknown
- 1968-02-22 CH CH259868A patent/CH490312A/de not_active IP Right Cessation
- 1968-02-26 BE BE711270D patent/BE711270A/xx unknown
- 1968-02-26 GB GB916168A patent/GB1193537A/en not_active Expired
- 1968-02-26 FR FR1555178D patent/FR1555178A/fr not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005036930A1 (de) * | 2005-08-05 | 2007-02-08 | Celanese Chemicals Europe Gmbh | Verfahren zur Isolierung von Vinylacetat |
| US7301048B2 (en) | 2005-08-05 | 2007-11-27 | Celanese Chemicals Europe Gmbh | Process for isolating vinyl acetate |
| DE102005036930B4 (de) * | 2005-08-05 | 2014-01-23 | Celanese Chemicals Europe Gmbh | Verfahren zur Isolierung von Vinylacetat |
| DE102016205487A1 (de) | 2016-04-04 | 2017-10-05 | Wacker Chemie Ag | Verfahren zur Herstellung von Vinylacetat |
| WO2017174463A1 (de) | 2016-04-04 | 2017-10-12 | Wacker Chemie Ag | Verfahren zur herstellung von vinylacetat |
| US10442750B2 (en) | 2016-04-04 | 2019-10-15 | Wacker Chemie Ag | Method for producing vinyl acetate |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1278430C2 (de) | 1974-05-30 |
| GB1193537A (en) | 1970-06-03 |
| CH490312A (de) | 1970-05-15 |
| BE711270A (enEXAMPLES) | 1968-08-26 |
| NL6801778A (enEXAMPLES) | 1968-08-26 |
| FR1555178A (enEXAMPLES) | 1969-01-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |