DE69216596D1 - Verfahren zur herstellung von einem alkanon und/oder alkanol - Google Patents

Verfahren zur herstellung von einem alkanon und/oder alkanol

Info

Publication number
DE69216596D1
DE69216596D1 DE69216596T DE69216596T DE69216596D1 DE 69216596 D1 DE69216596 D1 DE 69216596D1 DE 69216596 T DE69216596 T DE 69216596T DE 69216596 T DE69216596 T DE 69216596T DE 69216596 D1 DE69216596 D1 DE 69216596D1
Authority
DE
Germany
Prior art keywords
alkanon
alkanol
producing
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 - Fee Related
Application number
DE69216596T
Other languages
English (en)
Other versions
DE69216596T2 (de
Inventor
Ludovicus Janssen
Peter Hoogendoorn
Ubaldus Kragten
Henricus Baur
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DSM IP Assets BV
Original Assignee
DSM NV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by DSM NV filed Critical DSM NV
Publication of DE69216596D1 publication Critical patent/DE69216596D1/de
Application granted granted Critical
Publication of DE69216596T2 publication Critical patent/DE69216596T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
    • 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
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
    • B01J31/1625—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts immobilised by covalent linkages, i.e. pendant complexes with optional linking groups
    • B01J31/1633—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts immobilised by covalent linkages, i.e. pendant complexes with optional linking groups covalent linkages via silicon containing groups
    • 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
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • 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
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/226—Sulfur, e.g. thiocarbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • 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
    • B01J21/08—Silica
    • 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
    • B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
    • B01J2531/22—Magnesium
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/46—Titanium
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
    • B01J2531/56—Vanadium
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
    • B01J2531/62—Chromium
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
    • B01J2531/64—Molybdenum
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
    • B01J2531/72—Manganese
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/845—Cobalt
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/613—10-100 m2/g
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/615—100-500 m2/g
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/617—500-1000 m2/g
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic 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)
DE69216596T 1991-03-25 1992-03-19 Verfahren zur herstellung von einem alkanon und/oder alkanol Expired - Fee Related DE69216596T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL9100521A NL9100521A (nl) 1991-03-25 1991-03-25 Werkwijze voor de bereiding van een alkanon en/of alkanol.
PCT/NL1992/000053 WO1992016487A1 (en) 1991-03-25 1992-03-19 Process for preparing an alkanone and/or alkanol

Publications (2)

Publication Number Publication Date
DE69216596D1 true DE69216596D1 (de) 1997-02-20
DE69216596T2 DE69216596T2 (de) 1997-07-31

Family

ID=19859052

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69216596T Expired - Fee Related DE69216596T2 (de) 1991-03-25 1992-03-19 Verfahren zur herstellung von einem alkanon und/oder alkanol

Country Status (20)

Country Link
US (1) US5298665A (de)
EP (1) EP0577709B1 (de)
JP (1) JP3386827B2 (de)
CN (1) CN1047587C (de)
AU (1) AU1567692A (de)
BR (1) BR9205790A (de)
CA (1) CA2106863C (de)
CZ (1) CZ288134B6 (de)
DE (1) DE69216596T2 (de)
ES (1) ES2097909T3 (de)
HU (1) HU213837B (de)
IL (1) IL101350A (de)
MX (1) MX9201301A (de)
NL (1) NL9100521A (de)
PL (1) PL167350B1 (de)
RU (1) RU2078753C1 (de)
SK (1) SK102993A3 (de)
TW (1) TW198711B (de)
WO (1) WO1992016487A1 (de)
ZA (1) ZA922150B (de)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE1007904A3 (nl) * 1993-12-23 1995-11-14 Dsm Nv Werkwijze voor de bereiding van een alkanol en/of een alkanon.
DE19540497A1 (de) * 1995-10-31 1997-05-07 Degussa Sulfonat- und mercaptogruppenhaltige anorganische Trägermaterialien, Verfahren zu ihrer Herstellung und Verwendung als Katalysatoren
GB2314517A (en) * 1996-06-28 1998-01-07 Contract Chemicals Limited Catalyst and its use in epoxidation
KR20000068407A (ko) 1996-09-03 2000-11-25 메리 이. 보울러 히드로퍼옥시드 분해 방법
SK105899A3 (en) * 1997-02-11 2000-07-11 Du Pont Hydroperoxide decomposition process
US6160183A (en) * 1998-02-10 2000-12-12 E. I. Du Pont De Nemours And Company Direct oxidation of cycloalkanes
JP2002539097A (ja) * 1999-03-10 2002-11-19 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ヒドロペルオキシド分解方法
FR2802526B1 (fr) 1999-12-17 2003-04-18 Rhodia Polyamide Intermediates Procede de preparation de melanges alcools/cetones
WO2002016296A1 (en) * 2000-08-18 2002-02-28 E.I. Du Pont De Nemours And Company Improved hydroperoxide decomposition catalyst
FR2823745A1 (fr) * 2001-04-20 2002-10-25 Rhodia Polyamide Intermediates Procede de decomposition catalytique des hydroperoxydes organiques
JP2007223992A (ja) 2006-02-27 2007-09-06 Sumitomo Chemical Co Ltd シクロアルカノール及び／又はシクロアルカノンの製造方法
US7442841B2 (en) * 2006-08-18 2008-10-28 Invista North America S.A R.L. Extraction process
US7417003B2 (en) * 2006-12-29 2008-08-26 Uop Llc Solid acid catalyst and process for decomposition of cumene hydroperoxide
JP5176928B2 (ja) 2008-09-17 2013-04-03 住友化学株式会社 シクロアルカノール及び／又はシクロアルカノンの製造方法
CN102397794B (zh) * 2010-09-17 2013-09-11 中国科学院大连化学物理研究所 一种络合催化剂体系及其在分解环烷基过氧化氢中的应用
MX2013003637A (es) * 2010-10-01 2013-05-22 Ube Industries Catalizador de oxidacion para compuestos de hidrocarburo, y metodo y aparato para producir oxido de compuestos de hidrocarburo usando el mismo.
EP2446965A1 (de) * 2010-11-02 2012-05-02 Evonik Degussa GmbH Verfahren zur Herstellung von unterstützten Katalysatoren und Verwendung des Katalysators zur Veresterung von freien Fettsäuren in pflanzlichem Öl
BR112018006520B1 (pt) * 2015-10-01 2021-05-04 Monsanto Technology Llc processo para hidrogenação catalítica de halonitroaromáticos
JPWO2017057141A1 (ja) * 2015-10-01 2018-07-19 株式会社ダイセル 酸化反応用触媒、及びそれを用いたフローリアクター
CN110498735A (zh) * 2019-08-27 2019-11-26 浙江工业大学 钴(ii)盐/锌(ii)盐协同催化分子氧选择性氧化环烷烃制备环烷醇和环烷酮的方法

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2497349A (en) * 1947-08-01 1950-02-14 Union Oil Co Production of alicyclic alcohols
US2851496A (en) * 1954-07-27 1958-09-09 Du Pont Preparation of oxidation products of cyclohexane
FR1505363A (fr) * 1966-04-20 1967-12-15 Rhone Poulenc Sa Perfectionnement à la préparation des cycloalcanols et des mélanges cycloalcanols/cycloalcanones
GB1159006A (en) * 1966-07-11 1969-07-23 Ici Ltd Process for the Oxidation of Hydrocarbons.
FR1530986A (fr) * 1966-07-11 1968-06-28 Ici Ltd Procédé d'oxydation d'hydrocarbures
GB1212824A (en) * 1967-04-04 1970-11-18 Ici Ltd Production of alcohols and ketones
GB1449124A (en) * 1972-11-08 1976-09-15 Burmah Oil Trading Ltd Production of phenols
US4482752A (en) * 1974-02-19 1984-11-13 Mobil Oil Corporation Organic compound conversion
GB1502767A (en) * 1974-05-06 1978-03-01 Burmah Oil Trading Ltd Production of phenols
US4459427A (en) * 1981-10-31 1984-07-10 The British Petroleum Company P.L.C. Process for the conversion of an alkane to a mixture of an alcohol and a ketone
DE3222144A1 (de) * 1982-06-11 1983-12-15 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von cyclohexanol und cyclohexanon
US4490566A (en) * 1983-05-06 1984-12-25 Mobil Oil Corporation Production of phenol
EP0180269B1 (de) * 1984-11-02 1990-06-27 Shell Internationale Researchmaatschappij B.V. Katalysatorherstellung
NL8802592A (nl) * 1988-10-21 1990-05-16 Stamicarbon Werkwijze voor de bereiding van een k/a-mengsel.
US4898987A (en) * 1989-03-17 1990-02-06 Texaco Chemical Company Method for production of phenol/acetone from cumene hydroperoxide

Also Published As

Publication number Publication date
PL167350B1 (pl) 1995-08-31
CA2106863C (en) 2003-03-11
NL9100521A (nl) 1992-10-16
SK102993A3 (en) 1994-03-09
EP0577709B1 (de) 1997-01-08
WO1992016487A1 (en) 1992-10-01
US5298665A (en) 1994-03-29
ZA922150B (en) 1992-12-30
MX9201301A (es) 1992-10-01
EP0577709A1 (de) 1994-01-12
HUT64733A (en) 1994-02-28
CN1066839A (zh) 1992-12-09
CZ9302004A3 (en) 1994-04-13
TW198711B (de) 1993-01-21
HU213837B (en) 1997-10-28
AU1567692A (en) 1992-10-21
RU2078753C1 (ru) 1997-05-10
JP3386827B2 (ja) 2003-03-17
CZ288134B6 (en) 2001-05-16
CA2106863A1 (en) 1992-09-26
HU9302711D0 (en) 1993-12-28
JPH05112486A (ja) 1993-05-07
CN1047587C (zh) 1999-12-22
BR9205790A (pt) 1994-06-28
IL101350A (en) 1996-03-31
ES2097909T3 (es) 1997-04-16
IL101350A0 (en) 1992-11-15
DE69216596T2 (de) 1997-07-31

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