BE859769A - Procede de dimerisation - Google Patents
Procede de dimerisationInfo
- Publication number
- BE859769A BE859769A BE181782A BE181782A BE859769A BE 859769 A BE859769 A BE 859769A BE 181782 A BE181782 A BE 181782A BE 181782 A BE181782 A BE 181782A BE 859769 A BE859769 A BE 859769A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- acrylonitrile
- solvent
- compound
- radicals
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000006471 dimerization reaction Methods 0.000 title claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims 1
- PZTUCRXSJUYAEW-UHFFFAOYSA-N 4-diethoxyphosphanyl-n,n-dimethylaniline Chemical compound CCOP(OCC)C1=CC=C(N(C)C)C=C1 PZTUCRXSJUYAEW-UHFFFAOYSA-N 0.000 claims 1
- -1 hydrocarbyl radical Chemical class 0.000 description 20
- 239000002904 solvent Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 12
- 229910052698 phosphorus Inorganic materials 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 5
- 239000006184 cosolvent Substances 0.000 description 4
- 150000003018 phosphorus compounds Chemical class 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000005538 phosphinite group Chemical group 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- ZLQOJUZBHNXWJF-UHFFFAOYSA-N (4-methoxyphenoxy)phosphane Chemical compound COC1=CC=C(OP)C=C1 ZLQOJUZBHNXWJF-UHFFFAOYSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- FKRCVWBISKAAPX-UHFFFAOYSA-N di(propan-2-yloxy)phosphane Chemical compound CC(C)OPOC(C)C FKRCVWBISKAAPX-UHFFFAOYSA-N 0.000 description 1
- NKSSUPDYDFPQTA-UHFFFAOYSA-N diethoxy-(4-propan-2-yloxyphenyl)phosphane Chemical compound CCOP(OCC)C1=CC=C(OC(C)C)C=C1 NKSSUPDYDFPQTA-UHFFFAOYSA-N 0.000 description 1
- 239000007862 dimeric product Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols 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
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0257—Phosphorus acids or phosphorus acid esters
- B01J31/0261—Phosphorus acids or phosphorus acid esters comprising phosphonous acid (-ester) groups (RP(OR')2) or the isomeric phosphinic acid (-ester) groups (R2(R'O)P=O), i.e. R= C, R'= C, H
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0257—Phosphorus acids or phosphorus acid esters
- B01J31/0262—Phosphorus acids or phosphorus acid esters comprising phosphinous acid (-ester) groups (R2P(OR')) or the isomeric phosphine oxide groups (R3P=O), i.e. R= C, R'= C, H
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/14—Other (co) polymerisation, e.g. of lactides or epoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB45324/76A GB1551166A (en) | 1976-03-22 | 1976-10-21 | Pyrazolo (1,5-a)quinoxaline-3-carboxylic acid and derivatives thereof |
| GB5288876 | 1976-10-21 | ||
| GB1502977 | 1977-04-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE859769A true BE859769A (fr) | 1978-04-14 |
Family
ID=27516149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE181782A BE859769A (fr) | 1976-10-21 | 1977-10-14 | Procede de dimerisation |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US4138428A (en, 2012) |
| JP (1) | JPS5353616A (en, 2012) |
| BE (1) | BE859769A (en, 2012) |
| DE (1) | DE2747139A1 (en, 2012) |
| FR (1) | FR2368470B1 (en, 2012) |
| NL (1) | NL7711527A (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH633296A5 (de) * | 1977-08-19 | 1982-11-30 | Sandoz Ag | Verfahren zur herstellung von 4-(n,n-dialkylamino-)phenylphosphoniten. |
| DE2965244D1 (en) * | 1978-07-26 | 1983-05-26 | Ici Plc | Phosphinites and phosphonites, their preparation and use as acrylonitrile dimerisation catalysts |
| US4263224A (en) * | 1978-07-26 | 1981-04-21 | Imperial Chemical Industries Limited | Acrylonitrile dimerization process |
| DE2964157D1 (en) * | 1978-10-26 | 1983-01-05 | Ici Plc | A process for the dimerisation of acrylonitrile |
| US4661615A (en) * | 1982-11-03 | 1987-04-28 | Allied Corporation | Selective conversion of acrylonitrile into 1,4-dicyano-1-butene catalyzed by plymer-bound alkyl diarylphosphinites |
| US4574060A (en) * | 1982-11-03 | 1986-03-04 | Allied Corporation | Selective conversion of acrylonitrile into 1,4-dicyano-1-butene catalyzed by polymer-bound alkyl diarylphosphinites |
| JPS59215797A (ja) * | 1983-03-24 | 1984-12-05 | ユ−オ−ピ−・インコ−ポレ−テツド | 増強核沸騰面テ−プ及び電子部品の冷却 |
| DE3565830D1 (en) * | 1984-12-24 | 1988-12-01 | Monsanto Co | Dimerization process improvements |
| US4639539A (en) * | 1984-12-24 | 1987-01-27 | Monsanto Company | Dimerization process improvements |
| US4841087A (en) * | 1987-04-17 | 1989-06-20 | Monsanto Company | Acrylonitrile dimerization process |
| GB8817030D0 (en) * | 1988-07-18 | 1988-08-24 | Ici Plc | Dimerisation process |
| US4952541A (en) * | 1989-09-01 | 1990-08-28 | Monsanto Company | Acrylonitrile dimerization process and method of treating residual catalyst |
| GB9124303D0 (en) * | 1991-11-15 | 1992-01-08 | Ici Plc | Dimerisation of acrylonitrile |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055861A (en) * | 1958-02-19 | 1962-09-25 | Union Carbide Corp | Stabilized acrylonitrile vinyl or vinylidene copolymer solutions |
| DE1268614B (de) * | 1963-03-07 | 1968-05-22 | Basf Ag | Verfahren zur Herstellung von 1, 3-Dicyan-3-buten und dessen Isomeren aus Acrylsaeurenitril |
| US3574702A (en) * | 1965-03-02 | 1971-04-13 | Nat Distillers Chem Corp | Process for dimerizing acrylonitrile compounds |
| US3590069A (en) | 1966-02-01 | 1971-06-29 | Rohm & Haas | Method for the preparation of 2-methyleneglutaronitrile |
| GB1154275A (en) | 1966-04-19 | 1969-06-04 | Du Pont | Process for the Dimerization of Acrylonitrile |
| FR1519376A (fr) * | 1966-04-19 | 1968-03-29 | Du Pont | Procédé de dimérisation de l'acrylonitrile |
| DE1293155B (de) | 1966-05-14 | 1969-04-24 | Basf Ag | Verfahren zur Herstellung von 1, 3-Dicyan-3-buten durch Dimerisieren von Acrylsaeurenitril |
| US3631218A (en) | 1970-04-30 | 1971-12-28 | Shell Oil Co | Double bond isomerization of olefins |
| AU499165B2 (en) * | 1975-10-31 | 1979-04-05 | Ici Limited | Dimerisation process |
| US4532475A (en) * | 1983-03-09 | 1985-07-30 | Victor Company Of Japan, Limited | Impulse noise reduction by linear interpolation having a deemphasis characteristic |
-
1977
- 1977-10-13 US US05/841,924 patent/US4138428A/en not_active Expired - Lifetime
- 1977-10-14 BE BE181782A patent/BE859769A/fr not_active IP Right Cessation
- 1977-10-20 NL NL7711527A patent/NL7711527A/xx not_active Application Discontinuation
- 1977-10-20 FR FR7731589A patent/FR2368470B1/fr not_active Expired
- 1977-10-20 DE DE19772747139 patent/DE2747139A1/de active Granted
- 1977-10-20 JP JP12633977A patent/JPS5353616A/ja active Granted
-
1978
- 1978-10-17 US US05/952,138 patent/US4190616A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2368470B1 (fr) | 1983-09-09 |
| JPS6117819B2 (en, 2012) | 1986-05-09 |
| NL7711527A (nl) | 1978-04-25 |
| US4190616A (en) | 1980-02-26 |
| JPS5353616A (en) | 1978-05-16 |
| DE2747139A1 (de) | 1978-05-11 |
| US4138428A (en) | 1979-02-06 |
| FR2368470A1 (fr) | 1978-05-19 |
| DE2747139C2 (en, 2012) | 1990-04-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BE859769A (fr) | Procede de dimerisation | |
| Bolm et al. | Catalytic enantioselective conjugate addition of dialkylzinc compounds to chalcones | |
| EP1521738B1 (fr) | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique | |
| EP0000315A1 (fr) | Procédé de préparation de citronellal optiquement actif | |
| EP1567478B1 (fr) | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique | |
| FR2472598A1 (fr) | Composition adhesive a base de 2-cyanoacrylate d'alcoxyalcoyle ou de tetrahydrofurfuryle | |
| FR2488254A1 (fr) | Isomerisation du 2-methyl-3-butenenitrile en pentenenitriles lineaires | |
| US5221765A (en) | Racemization process for an optically active carboxylic acid or ester thereof | |
| LU80488A1 (fr) | Procede de preaparation de catalyseurs d'hydroformylation et d'hydrogenation a partir de complexes binucleaires du rhodium | |
| FR2845379A1 (fr) | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique | |
| FR2926816A1 (fr) | Procede de fabrication de composes comprenant des fonctions nitriles | |
| CA1266680A (fr) | Procede pour la fabrication de composes aldehydiques ou cetoniques et aldehydes et cetones obtenus par ce procede | |
| WO2004007508A2 (fr) | Fabrication de nitriles a partir de composes a insaturation ethylenique | |
| EP0445050B1 (fr) | Procédé de fabrication du bisphénol-A | |
| EP0323290B1 (fr) | Procédé de production d'aldéhydes aromatiques | |
| CH643226A5 (fr) | Procede de fabrication de composes carbonyles par oxydation de composes olefiniques. | |
| EP0270468A2 (fr) | Procédé de préparation d'un mélange renfermant un cyclohexanol et de la cyclohexanone à partir du cyclohexane | |
| FR2515640A1 (fr) | Procede de fabrication d'isocyanates aromatiques par carbonylation des derives nitres en presence de catalyseurs supportes prepares a partir de complexes heteropolymetalliques | |
| EP0266283A1 (fr) | Procédé de préparation d'un mélange renfermant du cyclohéxanol et de la cyclohéxanone à partir du cyclohéxane | |
| JPS61158953A (ja) | アクリルニトリルの二重化法 | |
| WO2010037786A1 (fr) | Procede de reduction de la concentration en ruthenium residuel dans des solutions, notamment dans des solutions contenant des produits issus de metathese d'olefines | |
| EP0117186B1 (fr) | Procédé de préparation de dérivés du cyclopropane | |
| EP0349380A1 (fr) | Nouveaux esters renfermant un groupement dithioacetal, leur préparation et leur application à la stabilisation des matières organiques | |
| WO2023046678A1 (fr) | Nouveaux dérivés borés, leur procédé de préparation et leur utilisation | |
| FR2479811A1 (fr) | Production selective de diacetate de phenylene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: IMPERIAL CHEMICAL INDUSTRIES LTD Effective date: 19941031 |