TW580489B - Copper-catalyzed vapor phase hydrocyanation of diolefinic compounds - Google Patents
Copper-catalyzed vapor phase hydrocyanation of diolefinic compounds Download PDFInfo
- Publication number
- TW580489B TW580489B TW091109774A TW91109774A TW580489B TW 580489 B TW580489 B TW 580489B TW 091109774 A TW091109774 A TW 091109774A TW 91109774 A TW91109774 A TW 91109774A TW 580489 B TW580489 B TW 580489B
- Authority
- TW
- Taiwan
- Prior art keywords
- item
- patent application
- copper
- scope
- catalyst composition
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 17
- 238000005669 hydrocyanation reaction Methods 0.000 title claims abstract description 17
- 239000012808 vapor phase Substances 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract description 55
- 239000003054 catalyst Substances 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 38
- 125000002015 acyclic group Chemical group 0.000 claims abstract description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- -1 diene compound Chemical class 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000010949 copper Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 229910052802 copper Inorganic materials 0.000 claims description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 8
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical group FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 2
- 238000011437 continuous method Methods 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 abstract description 4
- 150000001879 copper Chemical class 0.000 abstract description 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000007789 gas Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000012056 up-stream process Methods 0.000 description 9
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 8
- 239000001307 helium Substances 0.000 description 7
- 229910052734 helium Inorganic materials 0.000 description 7
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- YNYHGRUPNQLZHB-UHFFFAOYSA-M copper(1+);trifluoromethanesulfonate Chemical compound [Cu+].[O-]S(=O)(=O)C(F)(F)F YNYHGRUPNQLZHB-UHFFFAOYSA-M 0.000 description 5
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 4
- 229920000557 Nafion® Polymers 0.000 description 4
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910021536 Zeolite Inorganic materials 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000001450 anions Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WHTMVEKFWMRAJC-UHFFFAOYSA-N [Cu].[Cr].[Fe] Chemical compound [Cu].[Cr].[Fe] WHTMVEKFWMRAJC-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- LLTVNDUCLWASHR-UHFFFAOYSA-M copper(1+);4-methylbenzenesulfonate Chemical compound [Cu+].CC1=CC=C(S([O-])(=O)=O)C=C1 LLTVNDUCLWASHR-UHFFFAOYSA-M 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000013040 bath agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- NKKMVIVFRUYPLQ-UHFFFAOYSA-N but-2-enenitrile Chemical compound CC=CC#N NKKMVIVFRUYPLQ-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- AOLYLEFSPFALGJ-UHFFFAOYSA-N copper formazan Chemical compound [Cu].NN=CN=N AOLYLEFSPFALGJ-UHFFFAOYSA-N 0.000 description 1
- HDLKRBKBZRWMHV-UHFFFAOYSA-N copper hafnium Chemical compound [Cu].[Hf] HDLKRBKBZRWMHV-UHFFFAOYSA-N 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229960003529 diazepam Drugs 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000005242 forging Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical group [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910000734 martensite Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000002296 pyrolytic carbon Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29029401P | 2001-05-11 | 2001-05-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW580489B true TW580489B (en) | 2004-03-21 |
Family
ID=23115347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091109774A TW580489B (en) | 2001-05-11 | 2002-05-10 | Copper-catalyzed vapor phase hydrocyanation of diolefinic compounds |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6753440B2 (enExample) |
| EP (1) | EP1395547B1 (enExample) |
| JP (1) | JP4187534B2 (enExample) |
| BR (1) | BRPI0209588A2 (enExample) |
| CA (1) | CA2447051A1 (enExample) |
| CZ (1) | CZ20033001A3 (enExample) |
| DE (1) | DE60203286T2 (enExample) |
| MX (1) | MXPA03010214A (enExample) |
| MY (1) | MY124852A (enExample) |
| PL (1) | PL374445A1 (enExample) |
| RU (1) | RU2003135852A (enExample) |
| SG (1) | SG160228A1 (enExample) |
| SK (1) | SK13662003A3 (enExample) |
| TW (1) | TW580489B (enExample) |
| UA (1) | UA75918C2 (enExample) |
| WO (1) | WO2002092551A2 (enExample) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7897801B2 (en) | 2003-05-12 | 2011-03-01 | Invista North America S.A R.L. | Process for the preparation of dinitriles |
| US7919646B2 (en) | 2006-07-14 | 2011-04-05 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
| US7973174B2 (en) | 2005-10-18 | 2011-07-05 | Invista North America S.A.R.L. | Process of making 3-aminopentanenitrile |
| US7977502B2 (en) | 2008-01-15 | 2011-07-12 | Invista North America S.A R.L. | Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile |
| US8088943B2 (en) | 2008-01-15 | 2012-01-03 | Invista North America S.A R.L. | Hydrocyanation of pentenenitriles |
| US8101790B2 (en) | 2007-06-13 | 2012-01-24 | Invista North America S.A.R.L. | Process for improving adiponitrile quality |
| US8178711B2 (en) | 2006-03-17 | 2012-05-15 | Invista North America S.A R.L. | Method for the purification of triorganophosphites by treatment with a basic additive |
| US8247621B2 (en) | 2008-10-14 | 2012-08-21 | Invista North America S.A.R.L. | Process for making 2-secondary-alkyl-4,5-di-(normal-alkyl)phenols |
| US8338636B2 (en) | 2009-08-07 | 2012-12-25 | Invista North America S.A R.L. | Hydrogenation and esterification to form diesters |
| US8373001B2 (en) | 2003-02-10 | 2013-02-12 | Invista North America S.A R.L. | Method of producing dinitrile compounds |
| CN112892560A (zh) * | 2021-01-27 | 2021-06-04 | 南开大学 | 用于乙炔氢氯化反应的含氟弱配位阴离子改性铜基催化剂及其制备方法与应用 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6888032B2 (en) * | 2002-08-02 | 2005-05-03 | Massachusetts Institute Of Technology | Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds |
| FR2849027B1 (fr) * | 2002-12-23 | 2005-01-21 | Rhodia Polyamide Intermediates | Procede de synthese de composes comprenant des fonctions nitriles a partir de composes a insaturations ethyleniques |
| FR2854892B1 (fr) * | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| US7709674B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L | Hydrocyanation process with reduced yield losses |
| US7880028B2 (en) * | 2006-07-14 | 2011-02-01 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US8906334B2 (en) | 2007-05-14 | 2014-12-09 | Invista North America S.A R.L. | High efficiency reactor and process |
| EP2257516A4 (en) * | 2008-03-19 | 2012-12-12 | Invista Tech Sarl | METHODS FOR PREPARING CYCLODODECATRIENE AND METHODS FOR PREPARING LAUROLACTONE |
| DK2425916T3 (en) | 2010-09-01 | 2015-02-16 | Directa Plus Spa | MULTI-REACTOR FEED DEVICE FOR GENERATION OF METAL nanoparticles of |
| EP2425915B1 (en) * | 2010-09-01 | 2015-12-02 | Directa Plus S.p.A. | Multi mode production complex for nano-particles of metal |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2077260A (en) | 1935-05-22 | 1937-04-13 | Thomas D Stablow | Jar sealer |
| GB1084599A (en) | 1964-10-15 | 1967-09-27 | Asahi Chemical Ind | Process for the preparation of unsaturated aliphatic nitriles |
| US3578695A (en) | 1967-07-26 | 1971-05-11 | Standard Oil Co Ohio | Olefinic nitriles by the catalytic oxidation of olefins using hydrogen cyanide |
| US3869500A (en) | 1968-03-23 | 1975-03-04 | Asahi Chemical Ind | Process for the production of unsaturated aliphatic nitriles |
| US3547972A (en) | 1968-04-01 | 1970-12-15 | Du Pont | Addition of hydrogen cyanide to butadiene |
| US3584029A (en) | 1968-04-09 | 1971-06-08 | Asahi Chemical Ind | Process for the production of lower saturated aliphatic nitriles |
| US3766237A (en) | 1972-01-25 | 1973-10-16 | Du Pont | Hydrocyanation of olefins |
| US3865863A (en) | 1972-06-22 | 1975-02-11 | Hoffmann La Roche | 2-(Benzoyl)-3-dimethylaminoacrylonitriles |
| GB1565443A (en) | 1977-03-28 | 1980-04-23 | Ici Ltd | Manufacture of organic nitriles |
| GB1594694A (en) | 1977-04-04 | 1981-08-05 | Ici Ltd | Manufacture of organic nitriles by hydrocyanation of olefins |
| US5916837A (en) | 1994-01-12 | 1999-06-29 | E.I. Du Pont De Nemours And Company | Porous microcomposite of metal cation exchanged perfluorinated ion-exchanged polymer and network of metal oxide, silica or metal oxide and silica |
| US5449807A (en) * | 1994-11-18 | 1995-09-12 | E. I. Du Pont De Nemours And Company | Catalyzed vapor phase hydrocyanation of diolefinic compounds |
-
2002
- 2002-05-08 US US10/140,736 patent/US6753440B2/en not_active Expired - Fee Related
- 2002-05-10 JP JP2002589437A patent/JP4187534B2/ja not_active Expired - Fee Related
- 2002-05-10 WO PCT/US2002/014607 patent/WO2002092551A2/en not_active Ceased
- 2002-05-10 SK SK1366-2003A patent/SK13662003A3/sk unknown
- 2002-05-10 CZ CZ20033001A patent/CZ20033001A3/cs unknown
- 2002-05-10 DE DE60203286T patent/DE60203286T2/de not_active Expired - Lifetime
- 2002-05-10 BR BRPI0209588A patent/BRPI0209588A2/pt not_active IP Right Cessation
- 2002-05-10 RU RU2003135852/04A patent/RU2003135852A/ru not_active Application Discontinuation
- 2002-05-10 MX MXPA03010214A patent/MXPA03010214A/es active IP Right Grant
- 2002-05-10 PL PL02374445A patent/PL374445A1/xx unknown
- 2002-05-10 MY MYPI20021701A patent/MY124852A/en unknown
- 2002-05-10 TW TW091109774A patent/TW580489B/zh not_active IP Right Cessation
- 2002-05-10 EP EP02769693A patent/EP1395547B1/en not_active Expired - Lifetime
- 2002-05-10 CA CA002447051A patent/CA2447051A1/en not_active Abandoned
- 2002-05-10 SG SG200800339-4A patent/SG160228A1/en unknown
- 2002-10-05 UA UA20031110119A patent/UA75918C2/uk unknown
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8373001B2 (en) | 2003-02-10 | 2013-02-12 | Invista North America S.A R.L. | Method of producing dinitrile compounds |
| US7897801B2 (en) | 2003-05-12 | 2011-03-01 | Invista North America S.A R.L. | Process for the preparation of dinitriles |
| US7973174B2 (en) | 2005-10-18 | 2011-07-05 | Invista North America S.A.R.L. | Process of making 3-aminopentanenitrile |
| US8178711B2 (en) | 2006-03-17 | 2012-05-15 | Invista North America S.A R.L. | Method for the purification of triorganophosphites by treatment with a basic additive |
| US7919646B2 (en) | 2006-07-14 | 2011-04-05 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
| US8394981B2 (en) | 2006-07-14 | 2013-03-12 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
| US8101790B2 (en) | 2007-06-13 | 2012-01-24 | Invista North America S.A.R.L. | Process for improving adiponitrile quality |
| US7977502B2 (en) | 2008-01-15 | 2011-07-12 | Invista North America S.A R.L. | Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile |
| US8088943B2 (en) | 2008-01-15 | 2012-01-03 | Invista North America S.A R.L. | Hydrocyanation of pentenenitriles |
| US8247621B2 (en) | 2008-10-14 | 2012-08-21 | Invista North America S.A.R.L. | Process for making 2-secondary-alkyl-4,5-di-(normal-alkyl)phenols |
| US8338636B2 (en) | 2009-08-07 | 2012-12-25 | Invista North America S.A R.L. | Hydrogenation and esterification to form diesters |
| CN112892560A (zh) * | 2021-01-27 | 2021-06-04 | 南开大学 | 用于乙炔氢氯化反应的含氟弱配位阴离子改性铜基催化剂及其制备方法与应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2447051A1 (en) | 2002-11-21 |
| UA75918C2 (en) | 2006-06-15 |
| WO2002092551A2 (en) | 2002-11-21 |
| US20030045740A1 (en) | 2003-03-06 |
| MXPA03010214A (es) | 2004-03-10 |
| EP1395547A2 (en) | 2004-03-10 |
| BRPI0209588A2 (pt) | 2016-11-01 |
| US6753440B2 (en) | 2004-06-22 |
| MY124852A (en) | 2006-07-31 |
| JP2004534032A (ja) | 2004-11-11 |
| DE60203286T2 (de) | 2006-03-30 |
| CZ20033001A3 (cs) | 2005-05-18 |
| JP4187534B2 (ja) | 2008-11-26 |
| SG160228A1 (en) | 2010-04-29 |
| WO2002092551A8 (en) | 2003-12-18 |
| EP1395547B1 (en) | 2005-03-16 |
| SK13662003A3 (en) | 2004-11-03 |
| RU2003135852A (ru) | 2005-05-27 |
| PL374445A1 (en) | 2005-10-17 |
| DE60203286D1 (de) | 2005-04-21 |
| WO2002092551A3 (en) | 2003-02-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101484417B (zh) | 降低收率损失的氢氰化方法 | |
| JP3380543B2 (ja) | 改良されたヒドロシアン化方法 | |
| CN101484416B (zh) | 降低收率损失的氢氰化方法 | |
| JP4187534B2 (ja) | 銅触媒を用いたジオレフィン化合物の気相接触ヒドロシアン化法 | |
| TW519496B (en) | Catalyst comprising a complex of a metal of subgroup VIII based on a bidentate phosphonite ligand and preparation of nitriles. | |
| US7709673B2 (en) | Process for making 3-pentenenitrile by hydrocyanation of butadiene | |
| KR19990076626A (ko) | 디올레핀의 히드로시안화 및 비공액화 2-알킬-3-모노알켄니트릴의 이성질화의 개선된 방법 | |
| CN1283620C (zh) | 包含烯属不饱和度的有机化合物的氢氰化方法 | |
| BRPI0713247A2 (pt) | processo de hidrocianação e processo de produção de adiponitrila | |
| TW200303790A (en) | Phosphonite ligands and their use in hydrocyanation | |
| EP0755302A1 (en) | Bidentate phosphite and nickel catalyst compositions for hydrocyanation of monoolefins | |
| TWI245755B (en) | Hydrocyanation of olefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles | |
| TW527340B (en) | Separation of pentene nitrile isomers | |
| TW458959B (en) | Process for the vaper-phase hydrocyanation of diolefinic compounds and supported catalyst composition therefor | |
| TW200305555A (en) | Method of producing nitrile compounds from compounds with ethylenic unsaturation | |
| JP2013525280A (ja) | シス−２−ペンテンニトリルを３−ペンテンニトリルへと異性体化する方法 | |
| TW200413290A (en) | Cyclohexane derivatives and methods for their preparation | |
| CN104968433A (zh) | 改进的戊烯腈制备方法 | |
| EP1621531A1 (en) | Catayzed vapor-phase hydrocyanation of diolefinic compounds | |
| EP0891324B1 (en) | Catalyzed vapor-phase isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles | |
| CN110194739B (zh) | 一种氰烷基取代二氢异喹啉酮化合物及其制备方法 | |
| CA2186351C (en) | Bidentate phosphite and nickel catalyst compositions for hydrocyanation of monoolefins | |
| TH55294A (th) | ไฮโดรไซยาเนชันในเฟสไอที่ถูกเร่งปฏิกิริยาด้วยคอปเปอร์ของสารประกอบไดโอเลฟินิก |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |