GB1169525A - Method of Manufacturing Hydrodimer of Acrylonitrile - Google Patents
Method of Manufacturing Hydrodimer of AcrylonitrileInfo
- Publication number
- GB1169525A GB1169525A GB53869/66A GB5386966A GB1169525A GB 1169525 A GB1169525 A GB 1169525A GB 53869/66 A GB53869/66 A GB 53869/66A GB 5386966 A GB5386966 A GB 5386966A GB 1169525 A GB1169525 A GB 1169525A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphate
- quaternary ammonium
- adiponitrile
- lead
- dec
- 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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 abstract 4
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 abstract 2
- 239000001166 ammonium sulphate Substances 0.000 abstract 2
- 235000011130 ammonium sulphate Nutrition 0.000 abstract 2
- 239000012528 membrane Substances 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- -1 trimethylamine Chemical class 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical class C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910000978 Pb alloy Inorganic materials 0.000 abstract 1
- PPDNMTIPMRCZDI-UHFFFAOYSA-N S(=O)(=O)(O)O.CC1=C(N(C)C)C=CC=C1 Chemical compound S(=O)(=O)(O)O.CC1=C(N(C)C)C=CC=C1 PPDNMTIPMRCZDI-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910045601 alloy Inorganic materials 0.000 abstract 1
- 239000000956 alloy Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- AOIIZSJDYSLFOI-UHFFFAOYSA-L benzyl(trimethyl)azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.C[N+](C)(C)CC1=CC=CC=C1.C[N+](C)(C)CC1=CC=CC=C1 AOIIZSJDYSLFOI-UHFFFAOYSA-L 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000005341 cation exchange Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- RHSSOBQGZQVTHC-UHFFFAOYSA-L ethyl(trimethyl)azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CC[N+](C)(C)C.CC[N+](C)(C)C RHSSOBQGZQVTHC-UHFFFAOYSA-L 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000005342 ion exchange Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052753 mercury Inorganic materials 0.000 abstract 1
- 125000006178 methyl benzyl group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- RUFLMLWJRZAWLJ-UHFFFAOYSA-N nickel silicide Chemical compound [Ni]=[Si]=[Ni] RUFLMLWJRZAWLJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910021334 nickel silicide Inorganic materials 0.000 abstract 1
- 239000012074 organic phase Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/29—Coupling reactions
- C25B3/295—Coupling reactions hydrodimerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,169,525. Electrolytic production of adiponitrile. ASAHI KASEI KOGYO K. K. Dec.1, 1966 [Dec. 3, 1965; Dec.13, 1965], No.53869/66. Heading C7B. Adiponitrile is produced electrolytically in a divided cell separated by a cation exchange membrane, in which the catholyte is an aqueous solution containing acrylonitrile in a concentration of less than 10% by weight and a quaternary ammonium sulphate wherein the quaternary ammonium cation is an alkyl, aryl or aralkyl, heterocyclic or alkylalkanol quaternary ammonium cation, and the anolyte contains sulphuric acid. The adiponitrile produced may be extracted from the catholyte by addition of acrylonitrile thereto, the result separating into an organic phase containing the adiponitrile and an aqueous phase containing the quaternary ammonium sulphate, which may be returned to the cathode compartment. The quaternary ammonium compounds may include methyl, ethyl, butyl, propyl, phenyl, naphthyl, benzyl and methylbenzyl groups. Compounds which may be used include trimethylethylammonium sulphate, methylpyridiniun. sulphate, trimethylbenzylammonium sulphate and trimethylaniline sulphate. A solvent, e.g. acetonitrile, propionitrile, dioxane, dimethylformamide, dimethylsulphoxide or an amine, e.g. trimethylamine, may be present in the anolyte. The cathode may be formed of copper, lead, tin or mercury or an alloy thereof. The anode may be formed of platinum, nickel, nickel silicide, Duriron, lead or lead alloy, e.g. lead-antimony. The membrane may be formed of ion-exchange material having sulphonic acid groups or carboxyl groups, e.g. sulphonated styrene-divinylbenzene polymer.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7399665 | 1965-12-03 | ||
| JP7631565 | 1965-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1169525A true GB1169525A (en) | 1969-11-05 |
Family
ID=26415141
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB53869/66A Expired GB1169525A (en) | 1965-12-03 | 1966-12-01 | Method of Manufacturing Hydrodimer of Acrylonitrile |
| GB53870/66A Expired GB1170436A (en) | 1965-12-03 | 1966-12-01 | Process for Producing Adiponitrile |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB53870/66A Expired GB1170436A (en) | 1965-12-03 | 1966-12-01 | Process for Producing Adiponitrile |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3497429A (en) |
| BE (1) | BE690607A (en) |
| CH (1) | CH469678A (en) |
| DE (1) | DE1568054C3 (en) |
| ES (1) | ES334065A1 (en) |
| FR (2) | FR1503182A (en) |
| GB (2) | GB1169525A (en) |
| LU (1) | LU52478A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113774413A (en) * | 2021-09-30 | 2021-12-10 | 大连理工大学 | Method for preparing adiponitrile by safely and efficiently electrolyzing acrylonitrile in single-phase solution |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2047505A5 (en) * | 1969-05-08 | 1971-03-12 | Asahi Chemical Ind |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE24865E (en) * | 1960-09-06 | Ion exchange materials and method of | ||
| US3193480A (en) * | 1963-02-01 | 1965-07-06 | Monsanto Co | Adiponitrile process |
| BE631302A (en) * | 1962-04-20 | |||
| US3193481A (en) * | 1962-10-05 | 1965-07-06 | Monsanto Co | Electrolytic hydrodimerization alpha, beta-olefinic nitriles |
| US3267131A (en) * | 1964-04-27 | 1966-08-16 | Monsanto Co | Product separation and recovery in adiponitrile manufacture |
-
1966
- 1966-11-28 US US597207A patent/US3497429A/en not_active Expired - Lifetime
- 1966-12-01 LU LU52478A patent/LU52478A1/xx unknown
- 1966-12-01 GB GB53869/66A patent/GB1169525A/en not_active Expired
- 1966-12-01 GB GB53870/66A patent/GB1170436A/en not_active Expired
- 1966-12-01 DE DE1568054A patent/DE1568054C3/en not_active Expired
- 1966-12-02 FR FR86000A patent/FR1503182A/en not_active Expired
- 1966-12-02 ES ES0334065A patent/ES334065A1/en not_active Expired
- 1966-12-02 CH CH1727966A patent/CH469678A/en unknown
- 1966-12-02 BE BE690607D patent/BE690607A/xx not_active IP Right Cessation
- 1966-12-05 FR FR86138A patent/FR1503244A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113774413A (en) * | 2021-09-30 | 2021-12-10 | 大连理工大学 | Method for preparing adiponitrile by safely and efficiently electrolyzing acrylonitrile in single-phase solution |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1503182A (en) | 1967-11-24 |
| DE1568054B2 (en) | 1973-03-15 |
| ES334065A1 (en) | 1967-12-01 |
| FR1503244A (en) | 1967-11-24 |
| US3497429A (en) | 1970-02-24 |
| LU52478A1 (en) | 1967-02-01 |
| DE1568054C3 (en) | 1973-10-11 |
| DE1568053A1 (en) | 1972-03-30 |
| DE1568054A1 (en) | 1970-02-12 |
| CH469678A (en) | 1969-03-15 |
| BE690607A (en) | 1967-05-16 |
| GB1170436A (en) | 1969-11-12 |
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