GB1468940A - Preparation carboxylic acid anhydrides - Google Patents
Preparation carboxylic acid anhydridesInfo
- Publication number
- GB1468940A GB1468940A GB3851174A GB3851174A GB1468940A GB 1468940 A GB1468940 A GB 1468940A GB 3851174 A GB3851174 A GB 3851174A GB 3851174 A GB3851174 A GB 3851174A GB 1468940 A GB1468940 A GB 1468940A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- halide
- iii
- hydrocarbyl
- sept
- 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
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 9
- -1 hydrocarbyl halide Chemical class 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 150000001266 acyl halides Chemical class 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 238000005810 carbonylation reaction Methods 0.000 abstract 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 abstract 2
- 229910052740 iodine Inorganic materials 0.000 abstract 2
- 239000011630 iodine Substances 0.000 abstract 2
- 229910000510 noble metal Inorganic materials 0.000 abstract 2
- FVUHGTQDOMGZOT-NTSWFWBYSA-N (1s,3r)-3-methoxycarbonylcyclopentane-1-carboxylic acid Chemical compound COC(=O)[C@@H]1CC[C@H](C(O)=O)C1 FVUHGTQDOMGZOT-NTSWFWBYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 241001292396 Cirrhitidae Species 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 abstract 1
- 150000001255 actinides Chemical group 0.000 abstract 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical class C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 230000006315 carbonylation Effects 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 229910001502 inorganic halide Inorganic materials 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052747 lanthanoid Inorganic materials 0.000 abstract 1
- 150000002602 lanthanoids Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 abstract 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1468940 Carboxylic acid anhydrides HALCON INTERNATIONAL Inc 3 Sept 1974 [4 Sept 1973 8 May 1974] 38511/74 Heading C2C An anhydride of a monocarboxylic acid is prepared by reacting a carboxylic ester RCOOR (Reaction I) or an ether ROR (Reaction II) with an acyl halide RCOX under substantially anhydrous conditions; X is an iodine or bromine atom, the Rs may be the same or different, and each R is a monovalent hydrocarbyl radical which may be substituted, any substituent being inert under the reaction conditions. The acyl halide may be produced by carbonylation of a hydrocarbyl halide (Reaction III) at superatmospheric pressure, using preferably a Group VIII noble metal as catalyst and preferably also a promoter comprising an element of Groups IA, IIA, IIIA, IVB or VIB, a non-noble metal of Group VIII or a metal of the lanthanide or actinide groups. Reaction III may be carried out in a separate reaction zone from reactions I or II, and the hydrocarbyl halide RX formed in I or II recycled to III. Alternatively the anhydride forming and carbonylation reactions may be combined in a single reaction zone; the hydrocarbyl halide, of which no net consumption takes place, may be formed in situ by adding an organic or inorganic halide or elemental bromine or iodine. Reaction II proceeds in two stages, the first step, ROR + RCOX = RCOOR + RX, being followed by I as second step; ester so formed as intermediate may be recovered as by-product. The formation of acetic, propionic, caprylic and benzoic anhydrides from, respectively, methyl acetate, ethyl propionate, heptyl caprylate and phenyl benzoate is exemplified.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39422073A | 1973-09-04 | 1973-09-04 | |
| US46797774A | 1974-05-08 | 1974-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1468940A true GB1468940A (en) | 1977-03-30 |
Family
ID=27014635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3851174A Expired GB1468940A (en) | 1973-09-04 | 1974-09-03 | Preparation carboxylic acid anhydrides |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5550932B2 (en) |
| BG (1) | BG25203A3 (en) |
| BR (1) | BR7407075D0 (en) |
| CA (1) | CA1033761A (en) |
| CH (2) | CH609321A5 (en) |
| DD (1) | DD113521A5 (en) |
| DE (3) | DE2462444B2 (en) |
| DK (1) | DK466674A (en) |
| EG (1) | EG11306A (en) |
| ES (3) | ES429764A1 (en) |
| FR (1) | FR2242362B1 (en) |
| GB (1) | GB1468940A (en) |
| HU (1) | HU171902B (en) |
| IL (1) | IL45453A (en) |
| IT (1) | IT1019121B (en) |
| LU (1) | LU70831A1 (en) |
| NL (1) | NL169580C (en) |
| NO (1) | NO147183C (en) |
| PL (1) | PL105270B1 (en) |
| RO (1) | RO65730A (en) |
| SE (1) | SE413891B (en) |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4340570A (en) | 1981-03-06 | 1982-07-20 | The Halcon Sd Group, Inc. | Recovery of rhodium from carbonylation residues |
| US4340569A (en) | 1981-03-06 | 1982-07-20 | The Halcon Sd Group, Inc. | Treatment of carbonylation residues |
| US4341741A (en) | 1981-03-06 | 1982-07-27 | The Halcon Sd Group, Inc. | Recovery of rhodium from carbonylation residues |
| EP0064986A4 (en) * | 1980-11-21 | 1983-03-29 | Eastman Kodak Co | Preparation of acetic anhydride. |
| DE3248654A1 (en) * | 1981-12-30 | 1983-07-07 | The Halcon SD Group, Inc., 10016 New York, N.Y. | METHOD FOR CLEANING CARBONYLATION PRODUCTS |
| US4476237A (en) * | 1981-05-28 | 1984-10-09 | The Halcon Sd Group, Inc. | Separation of tars from carbonylation reaction mixtures |
| US4476238A (en) * | 1981-05-28 | 1984-10-09 | The Halcon Sd Group, Inc. | Separation of tars from carbonylation reaction mixtures |
| DE3432170A1 (en) * | 1983-09-02 | 1985-03-21 | Daicel Chemical Industries, Ltd., Sakai, Osaka | METHOD FOR THE PRODUCTION OF CARBONIC ACIDS |
| EP0134601A3 (en) * | 1983-07-28 | 1985-06-05 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of carboxylic acids |
| EP0097978B1 (en) * | 1982-06-18 | 1985-12-18 | Shell Internationale Researchmaatschappij B.V. | A process for the co-production of carboxylic acids |
| US4563309A (en) * | 1984-08-16 | 1986-01-07 | Union Carbide Corporation | Production of carboxylic anhydrides from methyl carboxlyates using rhodium complex catalysts |
| US5026908A (en) * | 1984-05-03 | 1991-06-25 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US5144068A (en) * | 1984-05-03 | 1992-09-01 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US5364822A (en) * | 1992-08-28 | 1994-11-15 | Bp Chemicals Limited | Process for the recovery of group VIII noble metals |
| EP0728727A1 (en) | 1995-02-21 | 1996-08-28 | BP Chemicals Limited | Process for the carbonylation of an alcohol |
| US6458996B1 (en) | 1998-07-29 | 2002-10-01 | Bp Chemicals Limited | Process for the production of acetic acid |
| US10464871B2 (en) | 2013-12-24 | 2019-11-05 | Bp P.L.C. | Process for the production of ethanol by hydrogenation of methyl acetate |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4002678A (en) * | 1975-12-22 | 1977-01-11 | Halcon International, Inc. | Preparation of carboxylic acid anhydrides |
| FR2507597B1 (en) * | 1981-06-12 | 1985-12-13 | Rhone Poulenc Chim Base | PROCESS FOR CARBONYLATION OF METHYL ACETATE |
| JPS6016950A (en) * | 1983-07-08 | 1985-01-28 | Daicel Chem Ind Ltd | Production of acetyl compound |
| EP0203286B1 (en) * | 1985-03-27 | 1988-09-14 | Hoechst Aktiengesellschaft | Supported catalyst and procedure for the production of monocarboxylic acid anhydrides |
| DE10138778A1 (en) | 2001-08-07 | 2003-02-20 | Basf Ag | Joint production of formic acid with a carboxylic (e.g. acetic) acid or derivatives, involves transesterifying a formic ester with a carboxylic acid, followed by carbonylation of the ester obtained |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1939216A (en) * | 1931-01-21 | 1933-12-12 | Monsanto Chemicals | Chemical treatment of organic acid halides |
| GB682174A (en) * | 1949-05-05 | 1952-11-05 | Hermann Teegen | Improvements in or relating to internal combustion engines for propelling pedal bicycles |
| DE921987C (en) * | 1952-06-12 | 1955-01-07 | Basf Ag | Process for the production of oxygen-containing organic compounds |
| DE1767151U (en) | 1958-03-03 | 1958-05-22 | Konrad Hellmich | CAMPING COOKING TABLE. |
| SE364255B (en) * | 1967-04-05 | 1974-02-18 | Monsanto Co | |
| SE364254B (en) * | 1967-04-05 | 1974-02-18 | Monsanto Co | |
| DE1966695U (en) | 1967-05-13 | 1967-08-17 | Karl Schwehr | IMPACT DEVICE. |
| US3717670A (en) * | 1968-08-02 | 1973-02-20 | Monsanto Co | Production of carboxylic acids and esters |
| US3579552A (en) * | 1968-08-15 | 1971-05-18 | Monsanto Co | Production of carboxylic acids |
| US3579551A (en) * | 1968-08-15 | 1971-05-18 | Monsanto Co | Production of carboxylic acids |
| US3845121A (en) * | 1971-11-10 | 1974-10-29 | Monsanto Co | Process for separating carbonylation products from reaction mixture without catalyst decomposition |
| JPS5030820U (en) * | 1973-07-16 | 1975-04-05 | ||
| DE2450965C2 (en) * | 1974-10-26 | 1983-06-09 | Hoechst Ag, 6230 Frankfurt | Process for the production of acetic anhydride |
| DE3016900A1 (en) * | 1980-05-02 | 1981-11-05 | Hoechst Ag, 6000 Frankfurt | METHOD FOR PRODUCING ACETYL CHLORIDE |
| DE3248468A1 (en) * | 1982-12-29 | 1984-07-12 | Hoechst Ag, 6230 Frankfurt | METHOD FOR PRODUCING CARBONIC ACID HALOGENIDES |
-
1974
- 1974-08-07 SE SE7410099A patent/SE413891B/en not_active IP Right Cessation
- 1974-08-12 IL IL45453A patent/IL45453A/en unknown
- 1974-08-26 BR BR7075/74A patent/BR7407075D0/en unknown
- 1974-08-27 NL NLAANVRAGE7411385,A patent/NL169580C/en not_active IP Right Cessation
- 1974-08-27 RO RO7479863A patent/RO65730A/en unknown
- 1974-08-27 IT IT52756/74A patent/IT1019121B/en active
- 1974-08-27 EG EG368/74A patent/EG11306A/en active
- 1974-08-29 HU HU74HA00000973A patent/HU171902B/en unknown
- 1974-08-30 BG BG027597A patent/BG25203A3/en unknown
- 1974-08-30 DE DE2462444A patent/DE2462444B2/en not_active Withdrawn
- 1974-08-30 DE DE2441502A patent/DE2441502B2/en not_active Ceased
- 1974-08-30 PL PL1974198641A patent/PL105270B1/en unknown
- 1974-08-30 CH CH1185674A patent/CH609321A5/en not_active IP Right Cessation
- 1974-08-30 LU LU70831*A patent/LU70831A1/xx unknown
- 1974-08-30 DE DE2462910A patent/DE2462910C2/en not_active Expired
- 1974-08-30 DD DD180813A patent/DD113521A5/xx unknown
- 1974-09-03 CA CA208,347A patent/CA1033761A/en not_active Expired
- 1974-09-03 FR FR7429944A patent/FR2242362B1/fr not_active Expired
- 1974-09-03 GB GB3851174A patent/GB1468940A/en not_active Expired
- 1974-09-03 DK DK466674A patent/DK466674A/da not_active Application Discontinuation
- 1974-09-03 NO NO743165A patent/NO147183C/en unknown
- 1974-09-04 JP JP10182674A patent/JPS5550932B2/ja not_active Expired
- 1974-09-04 ES ES429764A patent/ES429764A1/en not_active Expired
-
1976
- 1976-01-26 ES ES444609A patent/ES444609A1/en not_active Expired
- 1976-01-26 ES ES444608A patent/ES444608A1/en not_active Expired
-
1978
- 1978-03-08 CH CH253778A patent/CH614688A5/en not_active IP Right Cessation
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0064986A4 (en) * | 1980-11-21 | 1983-03-29 | Eastman Kodak Co | Preparation of acetic anhydride. |
| US4340570A (en) | 1981-03-06 | 1982-07-20 | The Halcon Sd Group, Inc. | Recovery of rhodium from carbonylation residues |
| US4340569A (en) | 1981-03-06 | 1982-07-20 | The Halcon Sd Group, Inc. | Treatment of carbonylation residues |
| US4341741A (en) | 1981-03-06 | 1982-07-27 | The Halcon Sd Group, Inc. | Recovery of rhodium from carbonylation residues |
| US4476237A (en) * | 1981-05-28 | 1984-10-09 | The Halcon Sd Group, Inc. | Separation of tars from carbonylation reaction mixtures |
| US4476238A (en) * | 1981-05-28 | 1984-10-09 | The Halcon Sd Group, Inc. | Separation of tars from carbonylation reaction mixtures |
| DE3248654A1 (en) * | 1981-12-30 | 1983-07-07 | The Halcon SD Group, Inc., 10016 New York, N.Y. | METHOD FOR CLEANING CARBONYLATION PRODUCTS |
| EP0097978B1 (en) * | 1982-06-18 | 1985-12-18 | Shell Internationale Researchmaatschappij B.V. | A process for the co-production of carboxylic acids |
| EP0134601A3 (en) * | 1983-07-28 | 1985-06-05 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of carboxylic acids |
| DE3432170A1 (en) * | 1983-09-02 | 1985-03-21 | Daicel Chemical Industries, Ltd., Sakai, Osaka | METHOD FOR THE PRODUCTION OF CARBONIC ACIDS |
| DE3432170C3 (en) * | 1983-09-02 | 1999-05-20 | Hoechst Celanese Corp | Process for the preparation of acetic acid by liquid phase carbonylation |
| US5026908A (en) * | 1984-05-03 | 1991-06-25 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US5144068A (en) * | 1984-05-03 | 1992-09-01 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US4563309A (en) * | 1984-08-16 | 1986-01-07 | Union Carbide Corporation | Production of carboxylic anhydrides from methyl carboxlyates using rhodium complex catalysts |
| US5364822A (en) * | 1992-08-28 | 1994-11-15 | Bp Chemicals Limited | Process for the recovery of group VIII noble metals |
| EP0728727A1 (en) | 1995-02-21 | 1996-08-28 | BP Chemicals Limited | Process for the carbonylation of an alcohol |
| US5939585A (en) * | 1995-02-21 | 1999-08-17 | Bp Chemicals Limited | Process for the carbonylation of an alcohol |
| US6458996B1 (en) | 1998-07-29 | 2002-10-01 | Bp Chemicals Limited | Process for the production of acetic acid |
| US10464871B2 (en) | 2013-12-24 | 2019-11-05 | Bp P.L.C. | Process for the production of ethanol by hydrogenation of methyl acetate |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| 748A | Application for an order for a licence (sect. 48/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19940902 |