DE3221175C2 - Verfahren zur Herstellung von Methylisobutyrat - Google Patents
Verfahren zur Herstellung von MethylisobutyratInfo
- Publication number
- DE3221175C2 DE3221175C2 DE3221175A DE3221175A DE3221175C2 DE 3221175 C2 DE3221175 C2 DE 3221175C2 DE 3221175 A DE3221175 A DE 3221175A DE 3221175 A DE3221175 A DE 3221175A DE 3221175 C2 DE3221175 C2 DE 3221175C2
- Authority
- DE
- Germany
- Prior art keywords
- fluoride
- esterification
- isobutyryl
- methanol
- anhydrous
- 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
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 title claims abstract description 53
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 96
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 59
- FSQOYWQCIXSBNP-UHFFFAOYSA-N 2-methylpropanoyl fluoride Chemical compound CC(C)C(F)=O FSQOYWQCIXSBNP-UHFFFAOYSA-N 0.000 claims abstract description 51
- 238000005886 esterification reaction Methods 0.000 claims abstract description 36
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 32
- 230000032050 esterification Effects 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims description 25
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 16
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 150000001450 anions Chemical class 0.000 abstract 2
- -1 methyl isobutyrate Chemical class 0.000 abstract 2
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000005810 carbonylation reaction Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GSJWYIDMIRQHMV-UHFFFAOYSA-N butanoyl fluoride Chemical compound CCCC(F)=O GSJWYIDMIRQHMV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical compound [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000005828 hydrofluoroalkanes Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
-
- 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
- C07C53/38—Acyl halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural 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 |
|---|---|---|---|
| US28212281A | 1981-07-10 | 1981-07-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3221175A1 DE3221175A1 (de) | 1983-01-27 |
| DE3221175C2 true DE3221175C2 (de) | 1985-08-29 |
Family
ID=23080195
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3221175A Expired DE3221175C2 (de) | 1981-07-10 | 1982-06-04 | Verfahren zur Herstellung von Methylisobutyrat |
| DE3249675A Expired DE3249675C2 (de) | 1981-07-10 | 1982-06-04 | Verfahren zur Herstellung von Methylmethacrylat |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3249675A Expired DE3249675C2 (de) | 1981-07-10 | 1982-06-04 | Verfahren zur Herstellung von Methylmethacrylat |
Country Status (12)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6135980U (ja) * | 1984-07-31 | 1986-03-05 | 東陶機器株式会社 | 便器洗浄用排水弁 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE972291C (de) * | 1954-05-16 | 1959-07-02 | Studiengesellschaft Kohle Mbh | Verfahren zur Herstellung von Monocarbonsaeuren aus Olefinen, Kohlenoxyd und Wasser |
| DE973077C (de) * | 1954-07-30 | 1959-11-26 | Studiengesellschaft Kohle Mbh | Verfahren zur Herstellung von Carbonsaeuren aus Olefinen und Kohlenoxyd |
| DE1064941B (de) * | 1957-04-24 | 1959-09-10 | Studiengesellschaft Kohle Mbh | Verfahren zur Herstellung von Gemischen aus gesaettigten aliphatischen oder cycloaliphatischen Monocarbonsaeurealkylestern |
| US3167585A (en) * | 1960-08-25 | 1965-01-26 | Gulf Research Development Co | Process for carboxylation of iso-olefins |
| GB942367A (en) * | 1961-04-29 | 1963-11-20 | Basf Ag | Continuous production of carboxylic acids from olefines, carbon monoxide and water |
| NL6816940A (enrdf_load_stackoverflow) * | 1967-11-28 | 1969-05-30 | ||
| BE755997A (fr) * | 1969-09-11 | 1971-03-10 | Bp Chem Int Ltd | Production d'acides dicarboxyliques |
| IT995328B (it) * | 1973-08-13 | 1975-11-10 | Montedison Spa | Procedimento per la preparazione di acidi alfa beta insaturi per ossidazione catalitica in fase gassosa di corrispondenti acidi saturi |
| US4224232A (en) * | 1978-12-21 | 1980-09-23 | Gulf Research & Development Company | Production of carboxylic acids from olefins and mixtures of olefins |
| DE3067475D1 (en) * | 1979-12-20 | 1984-05-17 | Roehm Gmbh | Process for the production of isobutyric acid or its lower alkyl esters |
-
1982
- 1982-06-04 FR FR8209810A patent/FR2509293B1/fr not_active Expired
- 1982-06-04 CH CH3478/82A patent/CH656872A5/de not_active IP Right Cessation
- 1982-06-04 BE BE0/208268A patent/BE893416A/fr not_active IP Right Cessation
- 1982-06-04 DE DE3221175A patent/DE3221175C2/de not_active Expired
- 1982-06-04 GB GB08216303A patent/GB2101592B/en not_active Expired
- 1982-06-04 DE DE3249675A patent/DE3249675C2/de not_active Expired
- 1982-06-04 KR KR8202510A patent/KR850001915B1/ko not_active Expired
- 1982-06-04 IT IT21705/82A patent/IT1195929B/it active
- 1982-06-04 CH CH158/86A patent/CH657845A5/de not_active IP Right Cessation
- 1982-06-04 CA CA000404471A patent/CA1156256A/en not_active Expired
- 1982-06-04 AU AU84607/82A patent/AU535364B2/en not_active Ceased
- 1982-06-04 NL NLAANVRAGE8202271,A patent/NL187015C/xx not_active IP Right Cessation
- 1982-06-04 JP JP57096068A patent/JPS5810538A/ja active Granted
- 1982-06-07 AT AT0220382A patent/AT390056B/de not_active IP Right Cessation
Non-Patent Citations (2)
| Title |
|---|
| NICHTS-ERMITTELT |
| Wörterbuch der industriellen Technik, 4. Aufl., 1975, S. 775 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU8460782A (en) | 1983-03-24 |
| DE3221175A1 (de) | 1983-01-27 |
| GB2101592B (en) | 1985-10-30 |
| BE893416A (fr) | 1982-10-01 |
| CH657845A5 (de) | 1986-09-30 |
| FR2509293A1 (fr) | 1983-01-14 |
| NL8202271A (nl) | 1983-02-01 |
| AU535364B2 (en) | 1984-03-15 |
| GB2101592A (en) | 1983-01-19 |
| KR840000469A (ko) | 1984-02-22 |
| IT1195929B (it) | 1988-11-03 |
| AT390056B (de) | 1990-03-12 |
| NL187015C (nl) | 1991-05-01 |
| KR850001915B1 (ko) | 1985-12-31 |
| CH656872A5 (de) | 1986-07-31 |
| DE3249675A1 (enrdf_load_stackoverflow) | 1985-04-18 |
| JPS5810538A (ja) | 1983-01-21 |
| DE3249675C2 (de) | 1987-01-08 |
| JPS6227055B2 (enrdf_load_stackoverflow) | 1987-06-12 |
| FR2509293B1 (fr) | 1987-02-27 |
| ATA220382A (de) | 1989-08-15 |
| CA1156256A (en) | 1983-11-01 |
| IT8221705A0 (it) | 1982-06-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69724266T2 (de) | Entfernung von permanganat reduzierenden verbindungen und alkyljodiden aus dem carbonylierungsprozesstrom | |
| DE69313506T2 (de) | Verfahren zur Herstellung von Essigsäure aus Methanol und Kohlenmonoxyd unter Verwendung eines Rhodiumkatalysators auf einem Träger | |
| DE69506493T2 (de) | Herstellung von Difluoressigsäurefluoride und von Ester der Difluoressigsäure | |
| DE69320568T2 (de) | Verfahren zur Rückgewinnung von Gruppe VIII Edelmetallen | |
| DE69634457T2 (de) | Verfahren zum Wiedergewinnen von Butylacrylat, das im Wesentlichen frei von Acrylsäure ist | |
| DE60118329T2 (de) | Verfahren und Vorrichtung zur Herstellung von Stickstofftrifluorid | |
| EP0082316A1 (de) | Verfahren zur Herstellung von Methyl-Tert.-butylether (MTBE) und weitgehend von i-Buten und von Methanol befreiten Kohlenwasserstoff-Raffinaten und Vorrichtung hierfür | |
| DE69108567T2 (de) | Kontinuierliches verfahren zur herstellung von essigsäureanhydrid oder einer mischung von essigsäureanhydrid und essigsäure. | |
| DE3221175C2 (de) | Verfahren zur Herstellung von Methylisobutyrat | |
| DE69500241T2 (de) | Verfahren zur Rückgewinnung von Ethylenoxid | |
| DE69011290T2 (de) | Verfahren zur Trennung von Fluorwasserstoffsäure von aromatische Ketone enthaltenden Gemischen. | |
| DE69318642T2 (de) | Verfahren zur Herstellung von Carbonester Verfahren zur Herstellung von Carbonester | |
| DE2110031C3 (de) | Verfahren zur Abtrennung von Methacrolein | |
| DE3604968A1 (de) | Verfahren zur herstellung von dichlorethan | |
| DE69206276T2 (de) | Verfahren zur entfernung von aceton aus einem carbonylierungsprozess. | |
| DE10255648B4 (de) | Verfahren und Vorrichtung zur hydrolytischen Gewinnung einer Carbonsäure und Alkohol aus dem entsprechenden Carbonsäureester | |
| DE69204493T2 (de) | Verfahren zur Reinigung von Dimethylcarbonat. | |
| DE3221174C2 (de) | Verfahren zur Herstellung von Isobuttersäure | |
| EP0617003A1 (de) | Verfahren zur Herstellung von Methylformiat | |
| DE69219022T2 (de) | Kontinuierverfahren zur Carbonylierung von Acetylenen | |
| DE3221173C2 (de) | Verfahren zur Herstellung von Isobutyrylfluorid | |
| DE19853908A1 (de) | Verfahren zur Herstellung von ungesättigten Ketonen | |
| DE3022256C2 (de) | Verfahren zur stufenweisen Neutralisierung von sulfatierten Alkoholen bzw. deren Äthylenoxid-Reaktionsprodukten | |
| DE2554702A1 (de) | Verfahren zur entalkylierung von tert.-alkyl-substituierten phenolen | |
| DE3221172A1 (de) | Verfahren zur herstellung von carbonsaeuren und estern |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8172 | Supplementary division/partition in: |
Ref country code: DE Ref document number: 3249675 Format of ref document f/p: P |
|
| Q171 | Divided out to: |
Ref country code: DE Ref document number: 3249675 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| AH | Division in |
Ref country code: DE Ref document number: 3249675 Format of ref document f/p: P |
|
| 8339 | Ceased/non-payment of the annual fee |