EP0558474A4 - Process for the preparation of phenyl carbonates - Google Patents
Process for the preparation of phenyl carbonatesInfo
- Publication number
- EP0558474A4 EP0558474A4 EP19910900661 EP91900661A EP0558474A4 EP 0558474 A4 EP0558474 A4 EP 0558474A4 EP 19910900661 EP19910900661 EP 19910900661 EP 91900661 A EP91900661 A EP 91900661A EP 0558474 A4 EP0558474 A4 EP 0558474A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- phenyl
- acetic anhydride
- acetate
- carbonate
- methyl 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title abstract description 7
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 title description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 51
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 15
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 15
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims abstract description 13
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229940049953 phenylacetate Drugs 0.000 claims abstract description 11
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 10
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 9
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- 229960003424 phenylacetic acid Drugs 0.000 claims description 2
- 229940071182 stannate Drugs 0.000 claims description 2
- 125000005402 stannate group Chemical group 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 239000001301 oxygen Substances 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229960003742 phenol Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- -1 aromatic carbonates Chemical class 0.000 description 6
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
Definitions
- the present invention relates to a process for the preparation of phenyl carbonates. More particularly, the present invention allows for the preparation of phenyl carbonates utilizing as reactants a phenol; acetic anhydride; carbon monoxide; and oxygen.
- step B reacting dimethyl carbonate with at least a portion of the phenyl acetate from step A to produce a phenyl carbonate and methyl acetate and separating the methyl acetate;
- step D employing the acetic anhydride as at least a portion of the acetic anhydride reactant of step A.
- reaction of phenols with acetic anhydride to form a phenyl acetate and acetic acid, step A of the present invention is a well known acetylation reaction, Suitable process conditions are disclosed, for example, in U.S. Patent 4,374,263.
- phenol is included hydroxy benzene and C ⁇ _ ⁇ _ j alkyl or halo substituted phenols, however, the preferred reactant is hydroxybenzene.
- the reaction of a phenol and acetic anhydride may be depicted by the following illustration. 0 0 0
- Ar represents a arvl group or alkyl or halo substituted aryl group, particularly phenyl.
- the reaction is conducted at moderate temperatures from 25°C to 180°C, more preferably 75°C to 150°C.
- the products are easily separated by fractional distillation or other suitable technique. While numerous catalysts are known for the esterification process, preferred catalysts are acids, especially heterogeneous macroporous ion exchange resins in the acid form.
- the dimethyl carbonate reactant for step B may be prepared by the reaction between methanol, carbon monoxide and oxygen, according to any suitable procedure. Suitable are those processes disclosed in U.S. Patents 3,846,468, 3,980,690, 4,452,690, 4,533,504, and 4,360,477.
- the reaction is generally expedited by the use of a catalyst, particularly a copper or cobalt complex and the use of elevated temperatures and pressures.
- Preferred catalysts are cuprous chloride complexed with an organic base such as pyridine, dipyridyl, imidazole, alkyl or aryl phosphines, etc.
- Preferred temperatures are from 20 to 75°C, more preferably 25 to 50°C.
- Preferred pressures of 0 2 and CO are from atmospheric to 20 atmospheres pressure. Reaction of dimethyl carbonate and a phenyl acetate to give the desired phenyl carbonate and by ⁇ product alkyl acetate is a known chemical transformation. This step of the process may be illustrated schematically by the following diagram.
- this reaction has been previously disclosed, for example, in U.S. Patent 4,182,726, and U.S. Patent 4,533,504.
- this reaction is conducted in 0 the presence of a catalyst, particularly a Lewis acid, such as AlCl , or stannate or titanate catalysts.
- Temperatures of the reaction are from 100°C to 350°C,._ _ preferably from 150°C to 300°C.
- Pressures are generally from atmospheric to 25 atmospheres, more preferably 5 to 5 10 atmospheres.
- the phenyl carbonate product is a highly desired article of commerce for conversion into polycarbonate resins. Processes for such conversion are 0 also well known having been disclosed in U.S. Patents
- the synthesized product may be a mixture of both the mono- and ditransesterified products, that is both the diphenyl carbonate and phenyl methyl carbonate products 5 are formed.
- the phenyl carbonate product and methyl acetate are readily separated by use of standard distillation techniques and the by-product, methyl acetate, is recycled by means of a reaction with carbon monoxide to produce acetic anhydride that is used in step A.
- Suitable processes for such reaction between methyl acetate and carbon monoxide are known and previously disclosed in the art, for example, in U.S. Patents 4,374,070, 4,559,183, and 4,046,807 and in S. W.
- a preferred process utilizes a noble metal catalyst and temperatures from 50°C to 250°C, preferably 100°C to 200°C, and pressures from atmospheric to 500 atmospheres, preferably 10 to 250 atmospheres.
- the present process scheme allows for the overall conversion of a phenol to the corresponding phenyl carbonate utilizing as reactants acetic anhydride, carbon monoxide and oxygen.
- the recycle of methyl acetate intermediate allows for great economy and simplicity in the resulting process compared to the generation of a ketene intermediate.
- the present process utilizes much lower reaction temperatures and results in greatly improved efficiency of operation.
- intermediate by ⁇ product acetic acid may also be recycled if desired by reaction with additional methanol to form methyl acetate and then carbonylated as above explained to form acetic anhydride.
- the acetic acid which represents a significant increase in value over the starting material, methanol, may be sold.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the preparation of an aromatic carbonate from a phenol, acetic anhydride, carbon monoxide and oxygen comprising the steps of A) reacting acetic anhydride with phenol to form phenyl acetate; B) reacting the phenyl acetate with dimethyl carbonate to produce a phenyl carbonate and methyl acetate; and C) reacting the methyl acetate with carbone monoxide to produce acetic anhydride for use in step A.
Description
PROCESS FOR THE PREPARATION OF PHENYL CARBONATES
The present invention relates to a process for the preparation of phenyl carbonates. More particularly, the present invention allows for the preparation of phenyl carbonates utilizing as reactants a phenol; acetic anhydride; carbon monoxide; and oxygen.
In U.S. Patent 4,533*504 an integrated process for the preparation of aromatic carbonates was disclosed
10 wherein the methyl acetate by-product formed in the transesterification of a phenyl ester with a dialkyl carbonate was recycled by heating the alkyl ester to form a ketene and subsequently such ketene was j|c reconverted by reaction with a phenol to form additional quantities of the phenyl ester.
Preparation of a ketene intermediate has proven costly and inefficient due to the high temperatures Q involved. Recoveries on the order of only about 80 percent of theoretical or less are typical leading to the need to develop a more efficient means of generating phenyl carbonate precursors and disposing of alkyl ester 5 by-products.
According to the present invention, there is now provided a process for producing an aromatic carbonate comprising the steps of:
A. reacting acetic anhydride with a phenol to produce a phenyl acetate and acetic acid and separating the phenyl acetate;
B. reacting dimethyl carbonate with at least a portion of the phenyl acetate from step A to produce a phenyl carbonate and methyl acetate and separating the methyl acetate;
C. reacting the methyl acetate with carbon monoxide in the presence of a catalyst to prepare acetic anhydride; and
D. employing the acetic anhydride as at least a portion of the acetic anhydride reactant of step A.
The reaction of phenols with acetic anhydride to form a phenyl acetate and acetic acid, step A of the present invention, is a well known acetylation reaction, Suitable process conditions are disclosed, for example, in U.S. Patent 4,374,263. By the term "phenol" is included hydroxy benzene and Cι_ι_j alkyl or halo substituted phenols, however, the preferred reactant is hydroxybenzene. In schematic form, the reaction of a phenol and acetic anhydride may be depicted by the following illustration.
0 0 0
» ιι II
ArOH + (CH3O2O ArOCCH3 + HOCCH3
wherein Ar represents a
arvl group or alkyl or halo substituted aryl group, particularly phenyl.
The reaction is conducted at moderate temperatures from 25°C to 180°C, more preferably 75°C to 150°C. The products are easily separated by fractional distillation or other suitable technique. While numerous catalysts are known for the esterification process, preferred catalysts are acids, especially heterogeneous macroporous ion exchange resins in the acid form.
The dimethyl carbonate reactant for step B may be prepared by the reaction between methanol, carbon monoxide and oxygen, according to any suitable procedure. Suitable are those processes disclosed in U.S. Patents 3,846,468, 3,980,690, 4,452,690, 4,533,504, and 4,360,477. The reaction is generally expedited by the use of a catalyst, particularly a copper or cobalt complex and the use of elevated temperatures and pressures. Preferred catalysts are cuprous chloride complexed with an organic base such as pyridine, dipyridyl, imidazole, alkyl or aryl phosphines, etc.
Preferred temperatures are from 20 to 75°C, more preferably 25 to 50°C. Preferred pressures of 02 and CO are from atmospheric to 20 atmospheres pressure.
Reaction of dimethyl carbonate and a phenyl acetate to give the desired phenyl carbonate and by¬ product alkyl acetate is a known chemical transformation. This step of the process may be illustrated schematically by the following diagram.
2 Ar0CCH3 + (CH3)2Cθ3 > ArOC02Ar + 2 CH3OCCH3
wherein Ar is as previously defined.
I
The above reaction has been previously disclosed, for example, in U.S. Patent 4,182,726, and U.S. Patent 4,533,504. In a highly desirable embodiment of the present invention, this reaction is conducted in 0 the presence of a catalyst, particularly a Lewis acid, such as AlCl , or stannate or titanate catalysts. Temperatures of the reaction are from 100°C to 350°C,._ _ preferably from 150°C to 300°C. Pressures are generally from atmospheric to 25 atmospheres, more preferably 5 to 5 10 atmospheres.
The phenyl carbonate product is a highly desired article of commerce for conversion into polycarbonate resins. Processes for such conversion are 0 also well known having been disclosed in U.S. Patents
3,625,920, 3,888,826 and 4,330,664. Included in the synthesized product may be a mixture of both the mono- and ditransesterified products, that is both the diphenyl carbonate and phenyl methyl carbonate products 5 are formed.
The phenyl carbonate product and methyl acetate are readily separated by use of standard distillation techniques and the by-product, methyl acetate, is recycled by means of a reaction with carbon monoxide to produce acetic anhydride that is used in step A. Suitable processes for such reaction between methyl acetate and carbon monoxide are known and previously disclosed in the art, for example, in U.S. Patents 4,374,070, 4,559,183, and 4,046,807 and in S. W. Polichnowski, J. CHEM. ED., 6 , 206 (1986). A preferred process utilizes a noble metal catalyst and temperatures from 50°C to 250°C, preferably 100°C to 200°C, and pressures from atmospheric to 500 atmospheres, preferably 10 to 250 atmospheres.
It may be readily observed that the present process scheme allows for the overall conversion of a phenol to the corresponding phenyl carbonate utilizing as reactants acetic anhydride, carbon monoxide and oxygen. The recycle of methyl acetate intermediate allows for great economy and simplicity in the resulting process compared to the generation of a ketene intermediate. The present process utilizes much lower reaction temperatures and results in greatly improved efficiency of operation. Moreover, intermediate by¬ product acetic acid may also be recycled if desired by reaction with additional methanol to form methyl acetate and then carbonylated as above explained to form acetic anhydride. Alternatively, the acetic acid, which represents a significant increase in value over the starting material, methanol, may be sold.
Claims
Claims
1. A process for producing a phenyl carbonate comprising the steps of:
A. reacting acetic anhydride with a phenol to produce a phenyl acetate and acetic acid and separating the phenyl acetate;
B. reacting dimethyl carbonate with at least a portion of the phenyl acetate from step A to produce a phenyl carbonate and methyl acetate and separating the methyl acetate;
C. reacting the methyl acetate with carbon monoxide in the presence of a catalyst to prepare acetic anhydride; and
D. employing the acetic anhydride as a least a portion of the acetic anhydride reactant of step A.
2. A process according to Claim 1 wherein the dimethyl carbonate and phenyl acetate are reacted in step B by contacting in the presence of a stannate or titanate catalyst.
3. A process according to claim 1, wherein the methyl acetate and carbon monoxide are reacted in step C by contacting at a temperature of from 100°C to 200°C in the presence of a noble metal catalyst.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1990/006860 WO1992009555A1 (en) | 1990-11-21 | 1990-11-21 | Process for the preparation of phenyl carbonates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0558474A1 EP0558474A1 (en) | 1993-09-08 |
| EP0558474A4 true EP0558474A4 (en) | 1993-09-29 |
Family
ID=22221177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19910900661 Withdrawn EP0558474A4 (en) | 1990-11-21 | 1990-11-21 | Process for the preparation of phenyl carbonates |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0558474A4 (en) |
| JP (1) | JPH05507060A (en) |
| WO (1) | WO1992009555A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW310322B (en) * | 1994-05-25 | 1997-07-11 | Nippon Catalytic Chem Ind | |
| US5714627A (en) * | 1995-08-28 | 1998-02-03 | Mitsubishi Gas Chemical Company, Inc. | Method for preparing aromatic carbonate |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046807A (en) * | 1974-10-26 | 1977-09-06 | Hoechst Aktiengesellschaft | Process for preparing acetic anhydride |
| US4182726A (en) * | 1974-06-25 | 1980-01-08 | Snamprogetti, S.P.A. | Process for the preparation of aromatic carbonates |
| US4374263A (en) * | 1979-10-27 | 1983-02-15 | The British Petroleum Company Limited | Process for the production of esters in the presence of a heterogeneous esterification catalyst |
| US4452968A (en) * | 1981-11-30 | 1984-06-05 | General Electric Company | Synthesis of polycarbonate from dialkyl carbonate and bisphenol diester |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4191996A (en) * | 1977-07-22 | 1980-03-04 | Chesley Gilman D | Self-configurable computer and memory system |
| JPS5524452A (en) * | 1978-08-08 | 1980-02-21 | Nec Corp | Integrated circuit |
| US4333885A (en) * | 1981-04-02 | 1982-06-08 | Air Products And Chemicals, Inc. | Method for producing carboxylic acid anhydride |
| US4533504A (en) * | 1982-01-08 | 1985-08-06 | General Electric Company | Process for the preparation of diaryl carbonates |
| US4498134A (en) * | 1982-01-26 | 1985-02-05 | Hughes Aircraft Company | Segregator functional plane for use in a modular array processor |
| JPS5968965A (en) * | 1982-10-13 | 1984-04-19 | Mitsubishi Electric Corp | semiconductor memory |
| JPS5987852A (en) * | 1982-11-10 | 1984-05-21 | Toshiba Corp | Semiconductor memory device |
-
1990
- 1990-11-21 EP EP19910900661 patent/EP0558474A4/en not_active Withdrawn
- 1990-11-21 WO PCT/US1990/006860 patent/WO1992009555A1/en not_active Ceased
- 1990-11-21 JP JP91500881A patent/JPH05507060A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4182726A (en) * | 1974-06-25 | 1980-01-08 | Snamprogetti, S.P.A. | Process for the preparation of aromatic carbonates |
| US4046807A (en) * | 1974-10-26 | 1977-09-06 | Hoechst Aktiengesellschaft | Process for preparing acetic anhydride |
| US4374263A (en) * | 1979-10-27 | 1983-02-15 | The British Petroleum Company Limited | Process for the production of esters in the presence of a heterogeneous esterification catalyst |
| US4452968A (en) * | 1981-11-30 | 1984-06-05 | General Electric Company | Synthesis of polycarbonate from dialkyl carbonate and bisphenol diester |
Non-Patent Citations (1)
| Title |
|---|
| See also references of WO9209555A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1992009555A1 (en) | 1992-06-11 |
| EP0558474A1 (en) | 1993-09-08 |
| JPH05507060A (en) | 1993-10-14 |
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