KR910000610A - 옥심의 촉매적 제조방법 - Google Patents
옥심의 촉매적 제조방법 Download PDFInfo
- Publication number
- KR910000610A KR910000610A KR1019890008737A KR890008737A KR910000610A KR 910000610 A KR910000610 A KR 910000610A KR 1019890008737 A KR1019890008737 A KR 1019890008737A KR 890008737 A KR890008737 A KR 890008737A KR 910000610 A KR910000610 A KR 910000610A
- Authority
- KR
- South Korea
- Prior art keywords
- titanium
- composition
- oxime
- compound
- catalyst
- Prior art date
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- 150000002923 oximes Chemical class 0.000 title claims 10
- 230000003197 catalytic effect Effects 0.000 title claims 6
- 238000002360 preparation method Methods 0.000 title claims 5
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000002329 infrared spectrum Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 17
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 13
- 239000000203 mixture Substances 0.000 claims 13
- 239000010936 titanium Substances 0.000 claims 13
- 229910052719 titanium Inorganic materials 0.000 claims 13
- 239000003054 catalyst Substances 0.000 claims 8
- 239000008247 solid mixture Substances 0.000 claims 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 4
- 229910010413 TiO 2 Inorganic materials 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 150000001728 carbonyl compounds Chemical class 0.000 claims 3
- 239000010949 copper Substances 0.000 claims 3
- 229910052802 copper Inorganic materials 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 229910052710 silicon Inorganic materials 0.000 claims 3
- 239000010703 silicon Substances 0.000 claims 3
- 150000003609 titanium compounds Chemical class 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 claims 2
- -1 Titanium halides Chemical class 0.000 claims 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 229920001296 polysiloxane Polymers 0.000 claims 2
- 239000011148 porous material Substances 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- 238000002310 reflectometry Methods 0.000 claims 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims 1
- 239000012965 benzophenone Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000000975 co-precipitation Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- NMGYKLMMQCTUGI-UHFFFAOYSA-J diazanium;titanium(4+);hexafluoride Chemical compound [NH4+].[NH4+].[F-].[F-].[F-].[F-].[F-].[F-].[Ti+4] NMGYKLMMQCTUGI-UHFFFAOYSA-J 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 229940032007 methylethyl ketone Drugs 0.000 claims 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 238000009987 spinning Methods 0.000 claims 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 claims 1
- 239000012808 vapor phase Substances 0.000 claims 1
- 239000003039 volatile agent Substances 0.000 claims 1
- 238000010586 diagram Methods 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/063—Titanium; Oxides or hydroxides thereof
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 실시예로부터 수득된 각 화합물의 X-선회절도를 도시한 도면이고,
제2도 및 3도는 실시예로부터 수득된 각 화합물의 적외선 스펙트럼을 도시한 도면이다.
Claims (19)
- 대응하는 카르보닐 화합물과 암모니아 및 과산화수소를 액상으로 반응시켜 옥심을 촉매적으로 제조함에 있어서, 촉매가 서로 화학적으로 결합된 적어도 실리콘, 티탄 및 산소로 이루어지며 전체 조성물에 있어서 TiO2로 환산하여 티탄양이 1 내지 95중량%의 범위내이고(구리의 Kα방사로 얻어진)XR회절도가 10 내지 40℃의 (2)범위 내에서 비결정성 고형물의 표시인 부드러운-편향성(할로)을 나타내는 고형 조성물임을 특징으로하는, 옥심의 촉매적 제조방법.
- 대응 카르보닐 화합물과 암모니아 및 과산화수소를 액상으로 반응시켜 옥심을 촉매적으로 제조함에 있어서, 촉매가 서로 화학적으로 결합된 실리콘, 티탄 및 산소로 이루어지며 전체조성물에 있어서 TiO2로 환산하여 티탄양이 1 내지 95중량%의 범위내이고(구리의 Kα방사로 얻어진)XR회절도가 10 내지 40℃의 (2)범위 내에서 비결정성 고형물의 표시인 반사도가 비결정성 고형물의 표시인 부드러운-편향성(할로)으로 대체된 고형 조성물임을 특징으로하는, 옥심의 촉매적 제조방법.
- 제1 또는 2항에 있어서, XR회절도에서 에추석 및/또는 금홍석 및/또는 브룩카이트를 나타내는 반사도가 나타남을 특징으로 하는 방법.
- 제1 내지 3항중 어느 한 항에 있어서, 조성물이 제2도에 도시한 형태의 적외선 스펙트럼에 의해 특징지워지는 방법.
- 제4항에 있어서, 적외선 스펙트럼이 750cm-1에서 밴드를 또한 포함하는 방법
- 제1 내지 5항중 어느 한 항에 있어서, 조성물중의 티탄 함유량이(TiO2)로 환산하여) 1 내지 50중량%, 바람직하게는 4.5 내지 50중량%인 방법.
- 제1 내지 6항중 어느 한 항에 있어서, 조성물의 표면적이 10 내지 800(바람직하게는 200 내지 800) m2/g, 기공부피가 0.1 내지 2.5cm3/g 그리고 평균 기공 직경이 0.70nm 보다 큰, 바람직하게는 1 내지 40nm인 방법.
- 제1 내지 7항중 어느 한 항에 있어서, 고형 조성물이-알킬-티타네이트, 특히 테트라이소프로필리타네이트 및 디-이소프로필-비스(트리에탄올아민)-티타네이트 ; -티탄할라이드, 특히 티탄메트라클로라이드(TiCl4) 및 티탄트리클로라이드(TiCl3) ; -착티타네이트, 특히 암모늄 헥사플루오로티타네이트(NH4)2TiF6; 이들의 배합물 및 등가물로부터 선택된 화합물을 티탄원으로 사용하여 수득되는 방법.
- 제1 내지 8항중 어느 한 항에 있어서, 고형 조성물이 TiCl4: (NH4)TiF6; 테트라이소프로필-티타네이트 ; 디-이소프로필-비스(트리에탄올아민) 티타네이트로부터 선택된 화합물을 티탄원으로 사용하여 수득되는 방법.
- 제1 내지 9항중 어느 한 항에 있어서, 옥심이 일반식 R1CHO(여기서, R1은 탄소수 1 내지 20의 알킬, 시클로알킬, 아릴 또는 헤테로환기로 부터 선택됨)의 알데히드를 촉매적 암모산화시킴으로써 수득되는 방법.
- 제1 내지 9항중 어느 한 항에 있어서, 옥심이 일반식 R2-CO-R3(여기서, R2및 R3는 동일하거나 상이하며 제10항에 있어서의 R1과 동일한 의미를 가지며 그들의 말단에 연결되어 카르보환 또는 헤테로환을 형성할 수 있다)의 케톤을 암모산화시킴으로써 수득되는 방법.
- 제1 내지 9항중 어느 한 항에 있어서, 옥심이 아세톤, 시클로헥사는, 메틸-에틸-케톤, 아세트페논, 벤조페논, t-부틸-시클로헥사는, 시클로-도데카논, 거울상 알데히드 및 벤즈알데히드로부터 선택된 화합물을 암모산화시킴으로써 수득되는 방법.
- 제1 내지 12항중 어느 한 항에 있어서, 촉매조성물이 실리콘 알코올레이트 및 티탄 알코올레이트의 알코올 용액을 가수분해함으로써 수득되는 방법
- 제1 내지 13항중 어느 한 항에 있어서, 촉매조성물이 수용성 실리콘 화합물 및 수용성 티탄 화합물의 수용액을 염기, 특히 암모늄 히드록사이드(NH4OH)으로 공침전시킴으로써 수득되는 방법.
- 제1 내지 14항중 어느 한 항에 있어서, 촉매조성물이 비결정성 실리카를 수용성 티탄 화합물의 수용액으로 함침시킴으로써 수득되는 방법.
- 제1 내지 15항중 어느 한 항에 있어서, 촉매조성물이 티탄휘발성 화합물을 증기상으로 되게하여 비결정성 실리카에 의해 흡수되도록 함으로써 수득되는 방법.
- 제1 내지 16항중 어느 한 항에 있어서, 촉매조성물이 비결정성 실리카를 비-수성매질에 가용성인 티탄 화합물의 비-수용액으로 함침시킴으로써 제조되는 방법.
- 제1 내지 17항중 어느 한항에 있어서, 사용전에 촉매조성물을 50 내지 800℃의 온도에서 하소시키는 방법.
- 화학적으로 서로 결합된 적어도 실리콘, 티탄 및 산소로 이루어지며, 전체 조성물중에 TiO2로 환산하여 티탄양이 1 내지 95중량%이며, 10 내지 40℃(2)범위 내에서 XR회절도(구리의 Kα방사에 의해 얻어짐)가 비결정성 고형물의 표시인 부드러운-편향성(할로)를 나타냄을 특징으로 하는, 대응 카르보닐 화합물을 암모산화하여 옥심을 제조하는데 적합한 촉매적 고형 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21076/88A IT1217899B (it) | 1988-06-23 | 1988-06-23 | Processo catalitico per la produzione di ossime |
| IT21076A/88 | 1988-06-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR910000610A true KR910000610A (ko) | 1991-01-29 |
| KR100202475B1 KR100202475B1 (en) | 1999-06-15 |
Family
ID=11176382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890008737A KR100202475B1 (en) | 1988-06-23 | 1989-06-23 | Catalytic process for the manufacture of oximes |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4968842A (ko) |
| EP (1) | EP0347926B1 (ko) |
| JP (1) | JPH0825979B2 (ko) |
| KR (1) | KR100202475B1 (ko) |
| AT (1) | ATE113580T1 (ko) |
| AU (1) | AU617824B2 (ko) |
| CA (1) | CA1336709C (ko) |
| DE (1) | DE68919134T2 (ko) |
| ES (1) | ES2063788T3 (ko) |
| IT (1) | IT1217899B (ko) |
| NO (1) | NO171061C (ko) |
| PT (1) | PT90949B (ko) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1230769B (it) * | 1989-02-21 | 1991-10-29 | Montedipe Spa | Processo catalitico per la produzione di ossime. |
| IT1244680B (it) * | 1991-01-23 | 1994-08-08 | Montedipe Srl | Processo a piu' stadi per l'ammossimazione in fase liquida dei composti carbonilici |
| US5316690A (en) * | 1991-04-18 | 1994-05-31 | Allied Signal Inc. | Hydrochlorofluorocarbons having OH rate constants which do not contribute substantially to ozone depletion and global warming |
| IT1252047B (it) * | 1991-07-10 | 1995-05-29 | Enichem Anic | Processo catalitico diretto per la produzione di idrossilammina |
| IT1255745B (it) * | 1992-04-01 | 1995-11-15 | Enichem Anic Srl | Processo in due stadi per la produzione in fase liquida di ossime |
| GB9210265D0 (en) * | 1992-05-13 | 1992-07-01 | Unilever Plc | Catalysts and catalyst supports |
| HU214200B (hu) * | 1992-12-03 | 1998-01-28 | Leuna-Katalysatoren Gmbh. | Oxidációs katalizátorok, valamint azok előállítására és alkalmazására szolgáló eljárások |
| FR2704159B1 (fr) * | 1993-04-22 | 1995-06-09 | Atochem Elf Sa | Catalyseur solide à base de silice particulaire, comportant du titane, Procédé d'obtention, et utilisation dans l'époxydation d'oléfines. |
| BE1007396A3 (fr) * | 1993-08-12 | 1995-06-06 | Solvay | Procede de preparation d'un support catalytique, catalyseur supporte pour la polymerisation d'olefines et procede pour la polymerisation d'olefines en presence de ce catalyseur. |
| IT1270196B (it) * | 1994-06-09 | 1997-04-29 | Enichem Spa | Procedimento catalitico per la produzione di ossime |
| DE4421928A1 (de) * | 1994-06-23 | 1996-01-04 | Basf Ag | Verfahren zur Herstellung von aliphatischen und cycloaliphatischen Oximen |
| US5466869A (en) * | 1994-10-31 | 1995-11-14 | Hoechst Celanese Corporation | Process for perparing 4-hydroxyacetophenone oxime |
| US5795555A (en) * | 1994-11-24 | 1998-08-18 | Alive; Keshavaraja | Micro-meso porous amorphous titanium silicates and a process for preparing the same |
| US5759945A (en) * | 1997-03-26 | 1998-06-02 | Arco Chemical Technology, L.P. | Preparation of titanium-containing catalysts using titanosiloxane polymers |
| US6011162A (en) * | 1997-05-05 | 2000-01-04 | Arco Chemical Technology, L.P. | Epoxidation process using improved heterogeneous catalyst composition |
| DE10103581A1 (de) * | 2001-01-26 | 2002-08-01 | Degussa | Durch Ammoniumsalze oder substituierte Ammoniumsalze cokatalysiertes Verfahren zur Herstellung von Oximen |
| JP4772326B2 (ja) | 2002-05-31 | 2011-09-14 | 中國石油化工股▲分▼有限公司 | チタン含有触媒の再生方法 |
| AU2003246098A1 (en) | 2002-05-31 | 2003-12-19 | China Petroleum And Chemical Corporation | Oxamidination process of carbonyl compounds |
| DE10352816A1 (de) * | 2003-11-12 | 2005-06-09 | Sachtleben Chemie Gmbh | Verfahren zur Herstellung eines hochtemperaturstabilen, TiO2-haltigen Katalysators oder Katalysatorträgers |
| ES2257950B1 (es) * | 2004-12-01 | 2007-07-16 | Ube Corporation Europe, S.A. | Procedimiento para la preparacion de oximas catalizado por un material laminar deslaminado. |
| CN101314577B (zh) * | 2007-05-31 | 2012-07-25 | 中国石油化工股份有限公司 | 一种催化环己酮氨肟化的方法 |
| TW201114729A (en) * | 2009-06-18 | 2011-05-01 | Sumitomo Chemical Co | Process for producing oxime |
| US8278487B2 (en) | 2010-02-04 | 2012-10-02 | Dsm Ip Assets B.V. | Catalytic process for the ammoximation of carbonyl compounds |
| KR20120123117A (ko) | 2010-02-04 | 2012-11-07 | 디에스엠 아이피 어셋츠 비.브이. | 카보닐 화합물의 암목시메이션을 위한 촉매적 방법 |
| EP2354119A1 (en) | 2010-02-04 | 2011-08-10 | Universiteit van Amsterdam | Catalytic process for the ammoximation of carbonyl compounds |
| TWI480100B (zh) | 2011-04-27 | 2015-04-11 | China Petrochemical Dev Corp Taipei Taiwan | Titanium-silicon molecular sieve and its preparation method and method for producing cyclohexanone oxime using the molecular sieve |
| TWI508935B (zh) | 2011-08-11 | 2015-11-21 | China Petrochemical Dev Corp Taipei Taiwan | Titanium-silicon molecular sieve and its preparation method and method for producing cyclohexanone oxime using the molecular sieve |
| CN103896801B (zh) * | 2012-12-25 | 2016-03-16 | 中国石油化学工业开发股份有限公司 | 制造酮肟的方法 |
| JP2015059100A (ja) * | 2013-09-19 | 2015-03-30 | 住友化学株式会社 | オキシムの製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5119743A (ja) * | 1974-08-05 | 1976-02-17 | Toray Industries | Shikuroarukanonokishimuno seizoho |
| DE2555901A1 (de) * | 1974-12-19 | 1976-06-24 | Mitsubishi Chem Ind | Verfahren zur herstellung von methacrylsaeureestern |
| US4163756A (en) * | 1978-04-11 | 1979-08-07 | Allied Chemical Corporation | Direct oximation of ketones |
| US4560797A (en) * | 1982-12-20 | 1985-12-24 | Allied Corporation | Oxidation of primary amines to oximes by elemental oxygen with catalyst regeneration |
| US4504681A (en) * | 1982-12-20 | 1985-03-12 | Allied Corporation | Catalytic oxidation of primary amines to oximes by elemental oxygen |
| IT1214622B (it) * | 1985-07-10 | 1990-01-18 | Montedipe Spa | Processo catalitico per laproduzione di cicloesanonossima. |
| US4794198A (en) * | 1986-11-14 | 1988-12-27 | Montedipe S.P.A. | Catalytic process for the manufacture of oximes |
| IT1222022B (it) * | 1987-07-14 | 1990-08-31 | Montedipe Spa | Metodo per la preparazione di un catalizzatore per l' ammossimazione di composti carbonilici |
| IT1222868B (it) * | 1987-10-12 | 1990-09-12 | Montedipe Spa | Metodo per la preparazione di titanio silicaliti |
-
1988
- 1988-06-23 IT IT21076/88A patent/IT1217899B/it active
-
1989
- 1989-06-21 CA CA000603490A patent/CA1336709C/en not_active Expired - Lifetime
- 1989-06-21 AU AU36731/89A patent/AU617824B2/en not_active Ceased
- 1989-06-22 DE DE68919134T patent/DE68919134T2/de not_active Expired - Lifetime
- 1989-06-22 JP JP1160574A patent/JPH0825979B2/ja not_active Expired - Lifetime
- 1989-06-22 PT PT90949A patent/PT90949B/pt not_active IP Right Cessation
- 1989-06-22 AT AT89111414T patent/ATE113580T1/de active
- 1989-06-22 ES ES89111414T patent/ES2063788T3/es not_active Expired - Lifetime
- 1989-06-22 EP EP89111414A patent/EP0347926B1/en not_active Expired - Lifetime
- 1989-06-22 NO NO892609A patent/NO171061C/no unknown
- 1989-06-23 KR KR1019890008737A patent/KR100202475B1/ko not_active IP Right Cessation
- 1989-09-15 US US07/407,733 patent/US4968842A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO171061B (no) | 1992-10-12 |
| KR100202475B1 (en) | 1999-06-15 |
| NO892609L (no) | 1989-12-27 |
| EP0347926B1 (en) | 1994-11-02 |
| ATE113580T1 (de) | 1994-11-15 |
| AU3673189A (en) | 1990-01-04 |
| EP0347926A3 (en) | 1991-07-03 |
| DE68919134D1 (de) | 1994-12-08 |
| PT90949A (pt) | 1989-12-29 |
| EP0347926A2 (en) | 1989-12-27 |
| IT8821076A0 (it) | 1988-06-23 |
| JPH0825979B2 (ja) | 1996-03-13 |
| NO892609D0 (no) | 1989-06-22 |
| PT90949B (pt) | 1994-11-30 |
| NO171061C (no) | 1993-01-20 |
| AU617824B2 (en) | 1991-12-05 |
| US4968842A (en) | 1990-11-06 |
| CA1336709C (en) | 1995-08-15 |
| ES2063788T3 (es) | 1995-01-16 |
| JPH0285240A (ja) | 1990-03-26 |
| IT1217899B (it) | 1990-03-30 |
| DE68919134T2 (de) | 1995-03-23 |
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