DE60203286T2 - Kupferkatalysierte dampfphasenhydrocyanierung von diolefinverbindungen - Google Patents
Kupferkatalysierte dampfphasenhydrocyanierung von diolefinverbindungen Download PDFInfo
- Publication number
- DE60203286T2 DE60203286T2 DE60203286T DE60203286T DE60203286T2 DE 60203286 T2 DE60203286 T2 DE 60203286T2 DE 60203286 T DE60203286 T DE 60203286T DE 60203286 T DE60203286 T DE 60203286T DE 60203286 T2 DE60203286 T2 DE 60203286T2
- Authority
- DE
- Germany
- Prior art keywords
- copper
- catalyst composition
- reaction
- hcn
- butadiene
- 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 - Lifetime
Links
- 238000005669 hydrocyanation reaction Methods 0.000 title claims description 19
- -1 DIOLEFIN COMPOUNDS Chemical class 0.000 title claims description 11
- 239000010949 copper Substances 0.000 title description 12
- 229910052802 copper Inorganic materials 0.000 title description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title description 8
- 238000004326 stimulated echo acquisition mode for imaging Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 55
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 45
- 239000003054 catalyst Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000000377 silicon dioxide Substances 0.000 claims description 15
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 9
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
- 239000002131 composite material Substances 0.000 claims description 4
- 150000001993 dienes Chemical class 0.000 claims description 4
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 239000007789 gas Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000012071 phase Substances 0.000 description 13
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 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
- 239000002184 metal Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- INRYEEIIXAOXBN-UHFFFAOYSA-N acetonitrile;copper(1+) Chemical compound [Cu+].CC#N INRYEEIIXAOXBN-UHFFFAOYSA-N 0.000 description 5
- YNYHGRUPNQLZHB-UHFFFAOYSA-M copper(1+);trifluoromethanesulfonate Chemical compound [Cu+].[O-]S(=O)(=O)C(F)(F)F YNYHGRUPNQLZHB-UHFFFAOYSA-M 0.000 description 5
- 229920000557 Nafion® Polymers 0.000 description 4
- 229910021536 Zeolite Inorganic materials 0.000 description 4
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 4
- 239000010457 zeolite Substances 0.000 description 4
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 2
- APPOKADJQUIAHP-UHMKDZKBSA-N (4e)-hexa-2,4-diene Chemical compound CC=C\C=C\C APPOKADJQUIAHP-UHMKDZKBSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical class C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 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
- 239000004677 Nylon Substances 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- RHQKKJPJCHGKQO-UHFFFAOYSA-N [Cu+2].[O-][Cr]([O-])=O Chemical class [Cu+2].[O-][Cr]([O-])=O RHQKKJPJCHGKQO-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- NKKMVIVFRUYPLQ-UHFFFAOYSA-N but-2-enenitrile Chemical compound CC=CC#N NKKMVIVFRUYPLQ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 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 1
- VMKYLARTXWTBPI-UHFFFAOYSA-N copper;dinitrate;hydrate Chemical compound O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O VMKYLARTXWTBPI-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000013011 mating Effects 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
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 1
- 229920005548 perfluoropolymer Polymers 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29029401P | 2001-05-11 | 2001-05-11 | |
| US290294P | 2001-05-11 | ||
| PCT/US2002/014607 WO2002092551A2 (en) | 2001-05-11 | 2002-05-10 | Copper-catalyzed vapor phase hydrocyanation of diolefinic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60203286D1 DE60203286D1 (de) | 2005-04-21 |
| DE60203286T2 true DE60203286T2 (de) | 2006-03-30 |
Family
ID=23115347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60203286T Expired - Lifetime DE60203286T2 (de) | 2001-05-11 | 2002-05-10 | Kupferkatalysierte dampfphasenhydrocyanierung von diolefinverbindungen |
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) |
Families Citing this family (20)
| 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 |
| FR2850966B1 (fr) * | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| FR2854892B1 (fr) * | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| WO2007046799A1 (en) * | 2005-10-18 | 2007-04-26 | Invista Technologies S.A R.L. | Process of making 3-aminopentanenitrile |
| CA2644961A1 (en) * | 2006-03-17 | 2007-09-27 | Invista Technologies 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 |
| 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 |
| 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 |
| EP2229353B1 (en) * | 2008-01-15 | 2018-01-03 | INVISTA Textiles (U.K.) Limited | Hydrocyanation of pentenenitriles |
| EP2257516A4 (en) * | 2008-03-19 | 2012-12-12 | Invista Tech Sarl | METHODS FOR PREPARING CYCLODODECATRIENE AND METHODS FOR PREPARING LAUROLACTONE |
| EP2334624B1 (en) * | 2008-10-14 | 2014-10-01 | Invista Technologies S.à.r.l. | Process for making 2-secondary-alkyl-4,5-di-(normal-alkyl)phenols |
| KR20120047251A (ko) * | 2009-08-07 | 2012-05-11 | 인비스타 테크놀러지스 에스.에이.알.엘. | 디에스테르를 형성하기 위한 수소화 및 에스테르화 |
| 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 |
| CN112892560B (zh) * | 2021-01-27 | 2022-10-25 | 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 |
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
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 |
| 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 |
| TW580489B (en) | 2004-03-21 |
| 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 |
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