CA1167064A - Process for making acetic anhydride and acetic acid - Google Patents
Process for making acetic anhydride and acetic acidInfo
- Publication number
- CA1167064A CA1167064A CA000413469A CA413469A CA1167064A CA 1167064 A CA1167064 A CA 1167064A CA 000413469 A CA000413469 A CA 000413469A CA 413469 A CA413469 A CA 413469A CA 1167064 A CA1167064 A CA 1167064A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- methyl
- bars
- reaction
- 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
Classifications
-
- 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
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
The disclosure relates to a process for making acetic anhydrid- and acetic-acid by reacting methyl acotate and/or dimethylether with carbon monoxide or mixtures of carbon monoxide and hydrogen at temperatures of 150 to 300°C, un-der reaction pressures of more than 80 bars and in the pre-sence of a catalyst system comprised of noble metals be-longing to group VIII of the Periodic System of the ele-ments, or their compounds, and optionally tertiary or qua-ternary organonitrogen or organophosphorus compounds. More particularly, the reaction is effected with the additional use of an organochlorine compound, chlorine or hydrogen chloride as a promoter.
The disclosure relates to a process for making acetic anhydrid- and acetic-acid by reacting methyl acotate and/or dimethylether with carbon monoxide or mixtures of carbon monoxide and hydrogen at temperatures of 150 to 300°C, un-der reaction pressures of more than 80 bars and in the pre-sence of a catalyst system comprised of noble metals be-longing to group VIII of the Periodic System of the ele-ments, or their compounds, and optionally tertiary or qua-ternary organonitrogen or organophosphorus compounds. More particularly, the reaction is effected with the additional use of an organochlorine compound, chlorine or hydrogen chloride as a promoter.
Description
~67~64 The present invention relates to a process for making acetic anhydride and acetic acid by reacting methyl aceta-te and/or dimethylether with carbon monoxide, optionally in the presence of hydrogen. This is a carbonylation reac-3 tion which permits C2-compounds to be produced from coal ~ia synthesis gas as an intermediary product, and has been disclosed in numerous patent applications. In carrying out the reaction, use has to be made of a catalyst system which often contains a noble metal belonging to group VIII of the Periodic System of the elements, and one or more promoters.
The promoters are most frequently selected from complex-forming amines or phosphines, organic iodide or bromide, and common metals, such as chromium, iron, cobalt or nickel.
It is remarkable that the reaction comprising several partial steps not fully disclosed heretofore could be cata-lyzed only with the use of promoters selected from iodine or bromine compounds, especially methyl iodide. In other words, in a carbonylation process of the kind described in German Specification DE-A-26 10 036, it is invariably ne-cessary for the iodine or bromine compound to be carefully recovered for reasons of economy and quality standard of the final product. To this end, German Specification DE-A-29 40 751 provides for the carbonylation products to be freed from iodine by treatment with cesium acetate, potas-sium acetate or sodium acetate at 100 up to 175C, the treatment resulting in the formation of practically non-volatile alkali metal iodides.
In view of this, considerably less expensive chlorine 1~L676~6~
compounds have reasonably been held in the art to be unsui-table for use as promoters and alkali metal salts have been assumed to destroy the catalytic efficiency of iodine- or bromine-contai.ning promoters inasmuch as the former under-go conversion to alkali metal iodides or bromides, at leastwithin the 100 to 175C temperature range recited abo~e.
The present invention now unexpectedly provides a pro-cess for making acetic anhydride and acetic acid by react-ing methyl acetate and/or dimethylether with carbon monoxi-de or mixturesof carbon monoxide and hydrogen at temperatu-res of 150 to 300C, under reaction pressures of more than 80 bars and in the presence of a catalyst system comprised of noble metals belonging to group VIII of the Periodic System of the elements or their compounds, and optionally tertiary or quaternary organonitrogen or organophosphorus compounds, which comprises effecting the reaction with the addltional use of an organochlorine compound, chlorine or hydrogen chloride as a promoter.
Preferred features of the present invention provide: 0 a) for methyl chloride to be used as organochlorine com-pound;
b) for org~nonitrogen or organophosphorus compounds qua-ternized with methyl chloride or hydrogen chloride to be used;
c) for alkali metal acetate or alkali metal compounds yielding alkali metal acetate under the reaction con-ditions to be used as additional promoters;
d) for methyl acetate or dimethylether/noble metal(-com-pound)/nitrogen compound or phosphorus compoundjchlo-~676~64 rine(-compound)/alkali metal compound to be used in a molar ratio o~ 1 : (0.0001 - 0.01) : (0.01 - 1) :
(0.01 - 1) : (0 - 0.1).
Some minor proportion of readily utilizable ethylidene diacetate is obtained as a by-product in the process of this invention.
The noble metals belonging to group VIII of the Perio-dic System used in the present process preferably comprise rhodium but also palladium, iridium or ruthenium. The me-tals are more preferably employed in the form of chloridesor acetates, e.g. RhCl3 . 3H20, IrCl3, Pd(CH3C00)2 The useful tertiary organonitrogen or organophosphorus compour,ds comprise amines, phosphines or aminophosphines, preferably alkylamines, N-alkylaniline, pyridine, pyrroli-done, alkyl or arylphosphines, especially N-methylimidazol, 3-picoline, 2,4-lutidine, 3,4-lutidine, quinoline~ tribu-tylphosphine, trioctylphosphine, trilaurylphosphine or tri-phenylphosphine. It is also possible however to use organo-nitrogen or organophosphorus compounds quaternized with me-thyl chloride or hydrogen chloride, e g. N-methylpyridinium chloride, N,N-dimethylimida~olium chloride, N-methyl-~-pico-linium chloride, N-methyl-2,4-lutidinium chloride, N-methyl-3,4-lutidinium chloride, N-methyl-quinolinium chloride; tri-butyl-methyl-phosphonium chloride, trioctyl-methyl-phospho-nium chloride, trilauryl-methyl-phosphonium chloride, tri phenyl-methyl-phosphonium chloride.
The comrosition of the feed gas(es) preferably varies between 100 volume % C0 and 20 volume % C0 + 80 volume %
H2. It is preferable however for C0 and H2 to be used in 1~67~6~
a ratio by volume of 90 : 10 to 50 : 50.
The reaction should conveniently be effected at tem-peratures of 180 to 250C under a pressure of 100 to 250 bars, up to 300 bars or more if desired or convenient.
The liquid phase which is to undergo reaction gene-rally consists of methyl acetate and/or dimethylether, an organochlorine compound, a noble metal of group VIII o~
the Periodic System of the elements yielding carbonyl com-pounds, and of an amine, phosphine and/or aminophosphine capable of inhibiting the deposition of undesirable noble metal-containing precipitate. In the process of this inven-tion, it is immaterial whether the reaction mixture has the catalyst system dissolved in it or whether the latter is present as a second liquid phase under the reaction condi-tions.
While the reaction is generally accelerated by the addition of some minor proportions of alkali metal salts, especially potassium, rubidium and cesium salts, it is not obligatory for these salts to be added in the event o~ the process being effected under commercial conditions.
Example 1 (Comparative Example) 250 g methyl acetate and 1.~ g RhCl3 . 3H20 were placed in a corrosionproof stainless steel autoclave (1 liter capa-city) pro~ided with an agitator. Next, 77 bars carbon mon-oxide and 34 bars hydrogen were introduced into the auto-clave, which was heated to a temperature of Z40C and in which a reaction pressure of 192 bars was found to estab-lish. After a so~ourn time of 5.3 h, the whole was cooled, the pressure released and the material in the autoclave 1~67~64 investigated gas-chromatographically. Aside ~rom 1.2 g ace-tic acid, no formation of new product could be found to have occurred.
Example 2 250 g methyl acetate, 100 g methyl chloride and 1.6 g RhCl3 0 3 H20 were placed in the agitator-provided autoclave of Example 1. Next, 80 bars C0 and 30 bars H2 were introduced and the autoclave was heated to 215C over a period of 18 hours. The reaction pressure increased up to 183 bars. me reaction mixture was worked up and analyzed gas-chromatogra-phically. 51.6 g acetic acid, 14.1 g acetic anhydride and 0.2 g ethylidene diacetate were found to have been formed.
Example 3 250 g methyl acetate, 100 g CH3Cl, 1.6 g RhCl3 . 3H20 and 8.2 g N-methylimidazol were placed in the autoclave.
After the introduction of 80 bars C0 and 30 bars H2, the autoclave was heated to 220C and a reaction pressure of 210 bars established therein. The so~ourn time was 7 hours.
A~ter work up, gas-chromatographic analysis indicated the formation of 73.6 g acetic acid and 44 g acetic anhydride.
Example 4 250 g methyl acetate, 100 g CH3Cl, 50 g methyl imidazol and 1.6 g RhCl3 . 3H20 were placed in the autocla~e~ After introduction of 80 bars C0 and 30 bars H2, 66 g acetic acid, 33 g acetic anhydride and 0.5 g ethylidene diacetate were obtained after 5 hours at a reaction temperature of 210C.
Example 5 76 bars C0 and 34 bars H2 were introduced into a mix-ture consisting of 250 g methyl acetate, 100 g CH3Cl, 13.3 g ~67~.4 N,N-dimethylimidazolium chloride and 1.6 g RhCl3 . 3H20.
After a reaction period o~ 4 h and 15 minutes at 220c, 38.1 g acetic acidt 55.6 g acetic anhydride and 1.5 g ethy-lidene diacetate were found to have been formed.
Example 6 m e reaction mixture consisted of 250 g methyl acetate, 26 g methyl chloride, 13.3 g N,N-dimethylimidazolium chlori-de and 1. 6 g RhCl3 . 3H20. The C0-pressure was 76 bars and the H2-pressure 34 bars. After a reaction period of 9 hours and 30 minute~ at 240C, 76.1 g acetic acid and 22.6 g ace-tic anhydride were found to have been formed.
Example 7 83 bars C0 and 38 bars H2 were introduced into a mix-ture of 250 g methyl acetate, 100 g methyl chloride, 50 g N-methyl-imidazol, 5 g potassium acetate, and 1.6 g RhCl~ .
3H20. Next, the autoclav~ was heated over a period of 7 hours to 205C . The reaction pressure reached 195 bars.
108 g acetic acid, 46 g acetic anhydride and 1 g ethylidene diacetate were obtained.
Example 8 83 bars C0 and 38 bars H2 were introduced into a mix-ture of 250 g methyl acetate, 100 g methyl chloride, 50 g N-methylimidazol, 10 g cesium acetate and 1.6 g RhCl3 .
3H20. 29 g acetic acid, 41 g acetic anhydride and 0. 2 g ethylidene diacetate were obtained after a reaction period of 3 hours at 200C under a reaction pressure which reached 155 bars.
Example 9 104 bars C0 and 10 bars H2 were introduced into a mix-ture of 250 g methyl acetate, 100 g methyl chloride, 50 g N-methyl-imidazol, 5 g pQtassium acetate and 1.35 g Pd (CH3C00)2. 82 g acetic acid and 7 g acetic anhydride were obtained after a reaction period of 8 hours at 240C under a reaction pressure which reached 191 bars.
Example 10 250 g methyl acetate, 100 g methyl chloride, 5 g pot-assium acetate and 1.4 g ruthenium-III-chloride were placed in the autoclave. After scavenging with C0-gas, 80 bars C0 and 20 bars H2 were introduced. 30 g acetic acid and 10 g acetic anhydride were obtained within 5 hours at a tempe-rature of 210C under a maximum reaction pressure of 180 bars. 3.8 g vinyl acetate was also obtained.
Example 11 100 g methyl chloride, 100 g dimethylether, 50 g N-methylimidazol and 1.6 g RhCl3 . 3H20 were placed in an autoclave. Next, 80 bars C0 and 20 bars H2 were introduced.
53 g methyl acetate and 36 g acetic acid were recovered from the reaction product obtained after a reaction period of 9 hours at 200C.
.
The promoters are most frequently selected from complex-forming amines or phosphines, organic iodide or bromide, and common metals, such as chromium, iron, cobalt or nickel.
It is remarkable that the reaction comprising several partial steps not fully disclosed heretofore could be cata-lyzed only with the use of promoters selected from iodine or bromine compounds, especially methyl iodide. In other words, in a carbonylation process of the kind described in German Specification DE-A-26 10 036, it is invariably ne-cessary for the iodine or bromine compound to be carefully recovered for reasons of economy and quality standard of the final product. To this end, German Specification DE-A-29 40 751 provides for the carbonylation products to be freed from iodine by treatment with cesium acetate, potas-sium acetate or sodium acetate at 100 up to 175C, the treatment resulting in the formation of practically non-volatile alkali metal iodides.
In view of this, considerably less expensive chlorine 1~L676~6~
compounds have reasonably been held in the art to be unsui-table for use as promoters and alkali metal salts have been assumed to destroy the catalytic efficiency of iodine- or bromine-contai.ning promoters inasmuch as the former under-go conversion to alkali metal iodides or bromides, at leastwithin the 100 to 175C temperature range recited abo~e.
The present invention now unexpectedly provides a pro-cess for making acetic anhydride and acetic acid by react-ing methyl acetate and/or dimethylether with carbon monoxi-de or mixturesof carbon monoxide and hydrogen at temperatu-res of 150 to 300C, under reaction pressures of more than 80 bars and in the presence of a catalyst system comprised of noble metals belonging to group VIII of the Periodic System of the elements or their compounds, and optionally tertiary or quaternary organonitrogen or organophosphorus compounds, which comprises effecting the reaction with the addltional use of an organochlorine compound, chlorine or hydrogen chloride as a promoter.
Preferred features of the present invention provide: 0 a) for methyl chloride to be used as organochlorine com-pound;
b) for org~nonitrogen or organophosphorus compounds qua-ternized with methyl chloride or hydrogen chloride to be used;
c) for alkali metal acetate or alkali metal compounds yielding alkali metal acetate under the reaction con-ditions to be used as additional promoters;
d) for methyl acetate or dimethylether/noble metal(-com-pound)/nitrogen compound or phosphorus compoundjchlo-~676~64 rine(-compound)/alkali metal compound to be used in a molar ratio o~ 1 : (0.0001 - 0.01) : (0.01 - 1) :
(0.01 - 1) : (0 - 0.1).
Some minor proportion of readily utilizable ethylidene diacetate is obtained as a by-product in the process of this invention.
The noble metals belonging to group VIII of the Perio-dic System used in the present process preferably comprise rhodium but also palladium, iridium or ruthenium. The me-tals are more preferably employed in the form of chloridesor acetates, e.g. RhCl3 . 3H20, IrCl3, Pd(CH3C00)2 The useful tertiary organonitrogen or organophosphorus compour,ds comprise amines, phosphines or aminophosphines, preferably alkylamines, N-alkylaniline, pyridine, pyrroli-done, alkyl or arylphosphines, especially N-methylimidazol, 3-picoline, 2,4-lutidine, 3,4-lutidine, quinoline~ tribu-tylphosphine, trioctylphosphine, trilaurylphosphine or tri-phenylphosphine. It is also possible however to use organo-nitrogen or organophosphorus compounds quaternized with me-thyl chloride or hydrogen chloride, e g. N-methylpyridinium chloride, N,N-dimethylimida~olium chloride, N-methyl-~-pico-linium chloride, N-methyl-2,4-lutidinium chloride, N-methyl-3,4-lutidinium chloride, N-methyl-quinolinium chloride; tri-butyl-methyl-phosphonium chloride, trioctyl-methyl-phospho-nium chloride, trilauryl-methyl-phosphonium chloride, tri phenyl-methyl-phosphonium chloride.
The comrosition of the feed gas(es) preferably varies between 100 volume % C0 and 20 volume % C0 + 80 volume %
H2. It is preferable however for C0 and H2 to be used in 1~67~6~
a ratio by volume of 90 : 10 to 50 : 50.
The reaction should conveniently be effected at tem-peratures of 180 to 250C under a pressure of 100 to 250 bars, up to 300 bars or more if desired or convenient.
The liquid phase which is to undergo reaction gene-rally consists of methyl acetate and/or dimethylether, an organochlorine compound, a noble metal of group VIII o~
the Periodic System of the elements yielding carbonyl com-pounds, and of an amine, phosphine and/or aminophosphine capable of inhibiting the deposition of undesirable noble metal-containing precipitate. In the process of this inven-tion, it is immaterial whether the reaction mixture has the catalyst system dissolved in it or whether the latter is present as a second liquid phase under the reaction condi-tions.
While the reaction is generally accelerated by the addition of some minor proportions of alkali metal salts, especially potassium, rubidium and cesium salts, it is not obligatory for these salts to be added in the event o~ the process being effected under commercial conditions.
Example 1 (Comparative Example) 250 g methyl acetate and 1.~ g RhCl3 . 3H20 were placed in a corrosionproof stainless steel autoclave (1 liter capa-city) pro~ided with an agitator. Next, 77 bars carbon mon-oxide and 34 bars hydrogen were introduced into the auto-clave, which was heated to a temperature of Z40C and in which a reaction pressure of 192 bars was found to estab-lish. After a so~ourn time of 5.3 h, the whole was cooled, the pressure released and the material in the autoclave 1~67~64 investigated gas-chromatographically. Aside ~rom 1.2 g ace-tic acid, no formation of new product could be found to have occurred.
Example 2 250 g methyl acetate, 100 g methyl chloride and 1.6 g RhCl3 0 3 H20 were placed in the agitator-provided autoclave of Example 1. Next, 80 bars C0 and 30 bars H2 were introduced and the autoclave was heated to 215C over a period of 18 hours. The reaction pressure increased up to 183 bars. me reaction mixture was worked up and analyzed gas-chromatogra-phically. 51.6 g acetic acid, 14.1 g acetic anhydride and 0.2 g ethylidene diacetate were found to have been formed.
Example 3 250 g methyl acetate, 100 g CH3Cl, 1.6 g RhCl3 . 3H20 and 8.2 g N-methylimidazol were placed in the autoclave.
After the introduction of 80 bars C0 and 30 bars H2, the autoclave was heated to 220C and a reaction pressure of 210 bars established therein. The so~ourn time was 7 hours.
A~ter work up, gas-chromatographic analysis indicated the formation of 73.6 g acetic acid and 44 g acetic anhydride.
Example 4 250 g methyl acetate, 100 g CH3Cl, 50 g methyl imidazol and 1.6 g RhCl3 . 3H20 were placed in the autocla~e~ After introduction of 80 bars C0 and 30 bars H2, 66 g acetic acid, 33 g acetic anhydride and 0.5 g ethylidene diacetate were obtained after 5 hours at a reaction temperature of 210C.
Example 5 76 bars C0 and 34 bars H2 were introduced into a mix-ture consisting of 250 g methyl acetate, 100 g CH3Cl, 13.3 g ~67~.4 N,N-dimethylimidazolium chloride and 1.6 g RhCl3 . 3H20.
After a reaction period o~ 4 h and 15 minutes at 220c, 38.1 g acetic acidt 55.6 g acetic anhydride and 1.5 g ethy-lidene diacetate were found to have been formed.
Example 6 m e reaction mixture consisted of 250 g methyl acetate, 26 g methyl chloride, 13.3 g N,N-dimethylimidazolium chlori-de and 1. 6 g RhCl3 . 3H20. The C0-pressure was 76 bars and the H2-pressure 34 bars. After a reaction period of 9 hours and 30 minute~ at 240C, 76.1 g acetic acid and 22.6 g ace-tic anhydride were found to have been formed.
Example 7 83 bars C0 and 38 bars H2 were introduced into a mix-ture of 250 g methyl acetate, 100 g methyl chloride, 50 g N-methyl-imidazol, 5 g potassium acetate, and 1.6 g RhCl~ .
3H20. Next, the autoclav~ was heated over a period of 7 hours to 205C . The reaction pressure reached 195 bars.
108 g acetic acid, 46 g acetic anhydride and 1 g ethylidene diacetate were obtained.
Example 8 83 bars C0 and 38 bars H2 were introduced into a mix-ture of 250 g methyl acetate, 100 g methyl chloride, 50 g N-methylimidazol, 10 g cesium acetate and 1.6 g RhCl3 .
3H20. 29 g acetic acid, 41 g acetic anhydride and 0. 2 g ethylidene diacetate were obtained after a reaction period of 3 hours at 200C under a reaction pressure which reached 155 bars.
Example 9 104 bars C0 and 10 bars H2 were introduced into a mix-ture of 250 g methyl acetate, 100 g methyl chloride, 50 g N-methyl-imidazol, 5 g pQtassium acetate and 1.35 g Pd (CH3C00)2. 82 g acetic acid and 7 g acetic anhydride were obtained after a reaction period of 8 hours at 240C under a reaction pressure which reached 191 bars.
Example 10 250 g methyl acetate, 100 g methyl chloride, 5 g pot-assium acetate and 1.4 g ruthenium-III-chloride were placed in the autoclave. After scavenging with C0-gas, 80 bars C0 and 20 bars H2 were introduced. 30 g acetic acid and 10 g acetic anhydride were obtained within 5 hours at a tempe-rature of 210C under a maximum reaction pressure of 180 bars. 3.8 g vinyl acetate was also obtained.
Example 11 100 g methyl chloride, 100 g dimethylether, 50 g N-methylimidazol and 1.6 g RhCl3 . 3H20 were placed in an autoclave. Next, 80 bars C0 and 20 bars H2 were introduced.
53 g methyl acetate and 36 g acetic acid were recovered from the reaction product obtained after a reaction period of 9 hours at 200C.
.
Claims (6)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
WE CLAIM
1. A process for making acetic anhydride and acetic acid by reacting methyl acetate and/or dimethylether with carbon monoxide or mixtures of carbon monoxide and hy-drogen at temperatures of 150 to 300°C, under reaction pressures of more than 80 bars and in the presence of noble metals belonging to group VIII of the Periodic System of the elements or their compounds as catalysts which comprises effecting the reaction in the further presence of an organochlorine compound, chlorine or hydrogen chloride as a promoter.
2. A process as claimed in claim 1, wherein tertiary or quaternary organonitrogen or organophosphorus compounds are used as an additional catalyst.
3. A process as claimed in claim 1, wherein methyl chlo-ride is used as organochlorine compound.
4. A process as claimed in claim 2, wherein organonitrogen or organophosphorus compounds quaternized with methyl chloride or hydrogen chloride are used.
5. A process as claimed in claim 1, wherein alkali metal acetate or alkali metal compounds yielding alkali me-tal acetate under the reaction conditions are used as an additional promoter.
6. A process as claimed in claim 1, 2 or 5, wherein methyl acetate or dimethylether/noble metal(-compound)/nitrogen compound or phosphorus compound/chlorine(-compound)/al-kali metal compound are used in a molar ratio of 1 :
(0.0001 - 0.01) : (0.01 - 1) : (0.01 - 1) : (0 - 0.1).
(0.0001 - 0.01) : (0.01 - 1) : (0.01 - 1) : (0 - 0.1).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813144772 DE3144772A1 (en) | 1981-11-11 | 1981-11-11 | METHOD FOR PRODUCING ACETIC ACID ANHYDRIDE AND ACETIC ACID |
| DEP3144772.4 | 1981-11-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1167064A true CA1167064A (en) | 1984-05-08 |
Family
ID=6146119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000413469A Expired CA1167064A (en) | 1981-11-11 | 1982-10-14 | Process for making acetic anhydride and acetic acid |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0079461B1 (en) |
| JP (1) | JPS5890527A (en) |
| AT (1) | ATE10618T1 (en) |
| AU (1) | AU9032982A (en) |
| BR (1) | BR8206519A (en) |
| CA (1) | CA1167064A (en) |
| DE (2) | DE3144772A1 (en) |
| ZA (1) | ZA828221B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4965234A (en) * | 1988-03-17 | 1990-10-23 | Hoechst Aktiengesellschaft | Supported catalyst for the preparation of monocarboxylic anhydrides |
| US5763654A (en) * | 1995-10-20 | 1998-06-09 | Bp Chemicals Limited | Process for the production of acetic acid by the carbonylation of dimethyl ether |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3429179A1 (en) * | 1984-08-08 | 1986-02-20 | Hoechst Ag, 6230 Frankfurt | METHOD FOR THE SIMULTANEOUS PRODUCTION OF CARBONIC ACIDS AND CARBONIC ACID ANHYDRIDES AND IF ANY. CARBONIC ACID ESTERS |
| GB8705699D0 (en) * | 1987-03-11 | 1987-04-15 | Shell Int Research | Carbonylation of olefinically unsaturated compounds |
| DE3811344A1 (en) * | 1988-04-02 | 1989-10-12 | Hoechst Ag | CARRIER CATALYST FOR THE PRODUCTION OF MONOCARBONIC ACID ANHYDRIDES |
| ES2055322T3 (en) * | 1989-04-06 | 1994-08-16 | Bp Chem Int Ltd | PROCESS TO PREPARE CARBOXILIC ACIDS. |
| US5442107A (en) * | 1989-04-06 | 1995-08-15 | Bp Chemicals Limited | Preparing carboxylic acids |
| GB9021454D0 (en) * | 1990-10-03 | 1990-11-14 | Bp Chem Int Ltd | Process |
| US9387469B2 (en) * | 2013-12-30 | 2016-07-12 | Eastman Chemical Company | Carbonylation catalyst and process using same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4102920A (en) * | 1977-01-13 | 1978-07-25 | Air Products & Chemicals, Inc. | Production of carboxylic acids and esters |
| US4102921A (en) * | 1977-04-26 | 1978-07-25 | Air Products & Chemicals, Inc. | Production of carboxylic acids and esters |
-
1981
- 1981-11-11 DE DE19813144772 patent/DE3144772A1/en not_active Withdrawn
-
1982
- 1982-10-08 DE DE8282109323T patent/DE3261477D1/en not_active Expired
- 1982-10-08 EP EP82109323A patent/EP0079461B1/en not_active Expired
- 1982-10-08 AT AT82109323T patent/ATE10618T1/en not_active IP Right Cessation
- 1982-10-14 CA CA000413469A patent/CA1167064A/en not_active Expired
- 1982-11-10 AU AU90329/82A patent/AU9032982A/en not_active Abandoned
- 1982-11-10 JP JP57196167A patent/JPS5890527A/en active Pending
- 1982-11-10 BR BR8206519A patent/BR8206519A/en unknown
- 1982-11-10 ZA ZA828221A patent/ZA828221B/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4965234A (en) * | 1988-03-17 | 1990-10-23 | Hoechst Aktiengesellschaft | Supported catalyst for the preparation of monocarboxylic anhydrides |
| US5763654A (en) * | 1995-10-20 | 1998-06-09 | Bp Chemicals Limited | Process for the production of acetic acid by the carbonylation of dimethyl ether |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5890527A (en) | 1983-05-30 |
| DE3261477D1 (en) | 1985-01-17 |
| EP0079461B1 (en) | 1984-12-05 |
| BR8206519A (en) | 1983-09-27 |
| ATE10618T1 (en) | 1984-12-15 |
| DE3144772A1 (en) | 1983-05-19 |
| ZA828221B (en) | 1983-10-26 |
| EP0079461A1 (en) | 1983-05-25 |
| AU9032982A (en) | 1983-05-19 |
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