UA75918C2 - A process for the gas phase hydrocyanation of diolefinic compounds - Google Patents
A process for the gas phase hydrocyanation of diolefinic compounds Download PDFInfo
- Publication number
- UA75918C2 UA75918C2 UA20031110119A UA20031110119A UA75918C2 UA 75918 C2 UA75918 C2 UA 75918C2 UA 20031110119 A UA20031110119 A UA 20031110119A UA 20031110119 A UA20031110119 A UA 20031110119A UA 75918 C2 UA75918 C2 UA 75918C2
- Authority
- UA
- Ukraine
- Prior art keywords
- composition
- differs
- carrier
- catalyst
- diolefin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 39
- 238000005669 hydrocyanation reaction Methods 0.000 title claims description 21
- 150000001875 compounds Chemical class 0.000 title abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- 125000002015 acyclic group Chemical group 0.000 claims abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 40
- -1 diolefin compounds Chemical class 0.000 claims description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 30
- 239000003245 coal Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 17
- 235000012239 silicon dioxide Nutrition 0.000 claims description 16
- 239000000377 silicon dioxide Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 13
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 8
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-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
- 229920000642 polymer Polymers 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 2
- 150000004699 copper complex Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000013354 porous framework Substances 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 150000001879 copper Chemical class 0.000 abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
- 239000012808 vapor phase Substances 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000012071 phase Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 238000004817 gas chromatography Methods 0.000 description 11
- 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 9
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 239000007789 gas 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
- 238000002474 experimental method Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- 229910021536 Zeolite Inorganic materials 0.000 description 3
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 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 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
- 239000011261 inert gas Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- YNYHGRUPNQLZHB-UHFFFAOYSA-M copper(1+);trifluoromethanesulfonate Chemical compound [Cu+].[O-]S(=O)(=O)C(F)(F)F YNYHGRUPNQLZHB-UHFFFAOYSA-M 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 2
- 229910021426 porous silicon Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-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
- 101100406843 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) prr-3 gene Proteins 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 241000320996 Poeta Species 0.000 description 1
- 101150080283 RIM8 gene Proteins 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 239000000969 carrier Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 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
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 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
- 230000009849 deactivation Effects 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 239000008187 granular material Substances 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000011068 loading method Methods 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
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 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
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29029401P | 2001-05-11 | 2001-05-11 | |
| PCT/US2002/014607 WO2002092551A2 (en) | 2001-05-11 | 2002-05-10 | Copper-catalyzed vapor phase hydrocyanation of diolefinic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA75918C2 true UA75918C2 (en) | 2006-06-15 |
Family
ID=23115347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20031110119A UA75918C2 (en) | 2001-05-11 | 2002-10-05 | A process for the gas 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) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20050032107A (ko) | 2002-08-02 | 2005-04-06 | 메사추세츠 인스티튜트 오브 테크놀로지 | 구리를 촉매로 한 탄소-헤테로원자 결합 및 탄소-탄소결합 형성방법 |
| 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 |
| FR2854892B1 (fr) * | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| EP2322503B1 (en) * | 2005-10-18 | 2014-12-31 | Invista Technologies S.à.r.l. | Process of making 3-aminopentanenitrile |
| CZ2008547A3 (cs) * | 2006-03-17 | 2009-06-10 | Invista Technologies S. A. R. L. | Zpusob purifikace triorganofosfitu ošetrením bazickým aditivem |
| US7919646B2 (en) * | 2006-07-14 | 2011-04-05 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
| US7880028B2 (en) * | 2006-07-14 | 2011-02-01 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US7709674B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L | Hydrocyanation process with reduced yield losses |
| US8906334B2 (en) | 2007-05-14 | 2014-12-09 | Invista North America S.A R.L. | High efficiency reactor and process |
| EP2164587B1 (en) * | 2007-06-13 | 2018-04-04 | INVISTA Textiles (U.K.) Limited | Process for improving adiponitrile quality |
| EP2229354B1 (en) * | 2008-01-15 | 2013-03-20 | Invista Technologies S.à.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 |
| JP2011515411A (ja) * | 2008-03-19 | 2011-05-19 | インビスタ テクノロジーズ エス エイ アール エル | シクロドデカトリエンの製造方法およびラウロラクトンの製造方法 |
| WO2010045131A1 (en) * | 2008-10-14 | 2010-04-22 | Invista Technologies 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 |
| EP2425915B1 (en) * | 2010-09-01 | 2015-12-02 | Directa Plus S.p.A. | Multi mode production complex for nano-particles of metal |
| DK2425916T3 (en) | 2010-09-01 | 2015-02-16 | Directa Plus Spa | MULTI-REACTOR FEED DEVICE FOR GENERATION OF METAL nanoparticles of |
| 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 PL PL02374445A patent/PL374445A1/xx unknown
- 2002-05-10 BR BRPI0209588A patent/BRPI0209588A2/pt not_active IP Right Cessation
- 2002-05-10 SK SK1366-2003A patent/SK13662003A3/sk unknown
- 2002-05-10 WO PCT/US2002/014607 patent/WO2002092551A2/en not_active Ceased
- 2002-05-10 RU RU2003135852/04A patent/RU2003135852A/ru not_active Application Discontinuation
- 2002-05-10 EP EP02769693A patent/EP1395547B1/en not_active Expired - Lifetime
- 2002-05-10 TW TW091109774A patent/TW580489B/zh not_active IP Right Cessation
- 2002-05-10 DE DE60203286T patent/DE60203286T2/de not_active Expired - Lifetime
- 2002-05-10 MX MXPA03010214A patent/MXPA03010214A/es active IP Right Grant
- 2002-05-10 CZ CZ20033001A patent/CZ20033001A3/cs unknown
- 2002-05-10 MY MYPI20021701A patent/MY124852A/en unknown
- 2002-05-10 SG SG200800339-4A patent/SG160228A1/en unknown
- 2002-05-10 CA CA002447051A patent/CA2447051A1/en not_active Abandoned
- 2002-10-05 UA UA20031110119A patent/UA75918C2/uk unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SG160228A1 (en) | 2010-04-29 |
| WO2002092551A8 (en) | 2003-12-18 |
| DE60203286D1 (de) | 2005-04-21 |
| MY124852A (en) | 2006-07-31 |
| RU2003135852A (ru) | 2005-05-27 |
| EP1395547A2 (en) | 2004-03-10 |
| PL374445A1 (en) | 2005-10-17 |
| EP1395547B1 (en) | 2005-03-16 |
| SK13662003A3 (en) | 2004-11-03 |
| US20030045740A1 (en) | 2003-03-06 |
| TW580489B (en) | 2004-03-21 |
| JP4187534B2 (ja) | 2008-11-26 |
| CA2447051A1 (en) | 2002-11-21 |
| DE60203286T2 (de) | 2006-03-30 |
| BRPI0209588A2 (pt) | 2016-11-01 |
| JP2004534032A (ja) | 2004-11-11 |
| WO2002092551A2 (en) | 2002-11-21 |
| CZ20033001A3 (cs) | 2005-05-18 |
| MXPA03010214A (es) | 2004-03-10 |
| US6753440B2 (en) | 2004-06-22 |
| WO2002092551A3 (en) | 2003-02-13 |
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