EP1286979A1 - Procede pour epoxyder des hydrocarbures - Google Patents

Procede pour epoxyder des hydrocarbures

Info

Publication number
EP1286979A1
EP1286979A1 EP01943326A EP01943326A EP1286979A1 EP 1286979 A1 EP1286979 A1 EP 1286979A1 EP 01943326 A EP01943326 A EP 01943326A EP 01943326 A EP01943326 A EP 01943326A EP 1286979 A1 EP1286979 A1 EP 1286979A1
Authority
EP
European Patent Office
Prior art keywords
volume
oxygen
solution
propene
metals
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.)
Withdrawn
Application number
EP01943326A
Other languages
German (de)
English (en)
Inventor
Ursula Jansen
Georg Wiessmeier
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.)
Covestro Deutschland AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of EP1286979A1 publication Critical patent/EP1286979A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
    • C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
    • C07D301/10—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase with catalysts containing silver or gold
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/825—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with gallium, indium or thallium
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • B01J23/8926—Copper and noble metals
    • 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
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • B01J37/0205—Impregnation in several steps
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
    • C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
    • 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

Definitions

  • the present invention relates to a process for the epoxidation of hydrocarbons with oxygen, characterized in that the process in the presence of a mixture comprising at least two metals from the group Cu, Ru, Rh, Pd, Os, Ir, Pt, Au, In, Tl, Mn, Ce is carried out on a support with a BET surface area of less than 200 m 2 / g and the use of a mixture comprising at least two metals from the group Cu, Ru, Rh, Pd, Os, Ir, Pt, Au , In, Tl, Mn, Ce on a support with a BET surface area of less than 200 m 2 / g for the epoxidation of hydrocarbons.
  • Epoxies are an important raw material for the polyurethane industry. There are a number of processes for their manufacture, some of which have been technically implemented. These are used today for the industrial production of ethylene oxide
  • EP-A1-0 930 308 describes e.g. the use of ion-exchanged titanium silicalites as a catalyst with these two oxidizing agents.
  • the oxidizing agent is oxygen, which is used in the presence of hydrogen.
  • the system is characterized by an exceptionally high selectivity (S> 95%) with regard to propene oxidation.
  • S> 95%) with regard to propene oxidation.
  • the low conversion and deactivation of the catalyst are disadvantageous. Not much is known in the literature about other active components besides silver and gold for the selective direct oxidation of propene and higher alkenes in the gas phase to the epoxides.
  • propene oxide can be produced with mixtures of different metals by direct oxidation of propene with oxygen or air. This is all the more unusual since, according to literature, the oxidation does not stop at the epoxide level, but the corresponding acids, ketones or
  • Aldehydes are formed.
  • the invention relates to a process for the epoxidation of hydrocarbons with oxygen, characterized in that the process in the presence of a mixture comprising at least two metals from the group Cu, Ru, Rh, Pd,
  • Os, Ir, Pt, Au, In, Tl, Mn, Ce is carried out on an inert support with a BET surface area of less than 200 m / g.
  • hydrocarbon is understood to mean unsaturated or saturated hydrocarbons such as olefins or alkanes, which also contain heteroatoms such as N, O, P,
  • S or halogens can contain.
  • the organic component to be oxidized can acyclic, monocyclic, bicyclic or polycyclic and can be monoolefinic, diolefinic or polyolefinic. In the case of organic components with two or more double bonds, the double bonds can be conjugated and non-conjugated.
  • Hydrocarbons are preferably oxidized, from which those oxidation products are formed whose partial pressure at the reaction temperature is low enough to remove the product continuously from the catalyst.
  • Unsaturated and saturated hydrocarbons having 2 to 20, preferably 3 to 10 carbon atoms are preferred 1,3-butadiene, pentene, pentane, 1-hexene, 1-hexane, hexadiene, cyclohexene, benzene.
  • the oxygen can be used in various forms, such as molecular oxygen, air and nitrogen oxide. Molecular oxygen is preferred.
  • Suitable mixtures are preferably binary or ternary mixtures of the metals Cu, Ru, Rh, Pd, Os, Ir, Pt, Au, In, Tl, Mn, Ce, the contents of the individual metals in each case in the range from 0-100 rel. % By weight and trivially add up to 100%.
  • the supports are compounds from the class of compounds of Al 2 O 3 , SiO 2 , CeO 2 , TiO 2 with BET surface areas ⁇ 200 m 2 / g, preferably ⁇ 100 m 2 / g, particularly preferably 10 m 2 / g and very particularly preferably ⁇ 1 m 2 / g.
  • the porosity is advantageously 20-60%, in particular 30-50%.
  • the particle size of the supports depends on the process conditions of the gas phase oxidation and is usually in the range from 1/10 to 1/20 of the reactor diameter.
  • the specific surface is determined in the usual way according to Brunauer, Emmet and Teller, J. Anorg. Chem. Soc. 1938, 60, 309, the porosity by the mercury porosimetry and the particle size of the metal particles on the carrier surface by means of electron microscopy.
  • the metal concentration on the carrier should generally be in the range from 0.001 to 50% by weight, preferably 0.001 to 20% by weight, very particularly preferably 0.01 to 5% by weight.
  • the generation of the metal particles on the carrier is not limited to one method.
  • To generate metal particles here are some example methods such as deposition precipitation as described in EP-B-0 709 360 on page 3, lines 38 ff., Impregnation in solution, incipient wetness, colloid method, Sputtering, called CVD, PVD.
  • Incipient wetness means the addition of a solution containing soluble metal compounds to the support material, the volume of the solution which is added to the support being less than or equal to the pore volume of the support.
  • the carrier thus remains macroscopically dry. All solvents in which the metal extenders are soluble, such as water, alcohols, (crown) ethers, esters, ketones, halogenated hydrocarbons, etc., can be used as solvents for incipient wetness.
  • the carrier is preferably impregnated with a solution containing the metal ions and then dried, calcined and reduced.
  • the solution can additionally contain components known to the person skilled in the art which increase the solubility of the or increase the metal salts in the solvent and / or change the redox potentials of the metals and / or change the pH.
  • Ammonia, amines, diamines, hydroxyamines and acids such as HC1, HNO 3 , H 2 SO 4 , H 3 PO 4 may be mentioned in particular.
  • Soaking can e.g. through Incipient Wetness, but is not limited to this.
  • the Incipient Wetness Process can include the following steps:
  • the oxygen content in the gas stream is advantageously in the range from 0 to 21% by volume, preferably from 5 to 15% by volume.
  • the temperature for the calcination, the metal mixture is adapted and is therefore generally in the range from 400 to 600 ° C., preferably 450-550 ° C., particularly preferably 500 ° C.
  • the hydrogen content can be between 0-100% by volume, but preferably 0-25, particularly preferably 5% by volume.
  • the reduction temperatures are adapted to the respective metal mixture and are between 100 and 600 ° C.
  • alkaline earth and / or alkali ions as hydroxides, carbonates, nitrates, chlorides of one or more alkaline earth and / or alkali metals.
  • the epoxidation process is usually carried out under the following conditions, preferably in the gas phase:
  • the molar amount of the hydrocarbon used in relation to the total molar number of hydrocarbon, oxygen and, if appropriate, diluent gas and the relative molar ratio of the components can be varied within a wide range and is generally based on the explosion limits of the hydrocarbon-oxygen mixture. As a rule, work is carried out above or below the explosion limit.
  • hydrocarbon content based on the molar sum of hydrocarbon and oxygen, is typically ⁇ 2 mol% or> 78 mol%. Hydrocarbon contents in the range of 0.5-2 mol% are preferred for procedures below
  • Explosion limit and 78-99 mole% when driving above the explosion limit selected are particularly preferred.
  • An excess of hydrocarbon, based on the oxygen used (on a molar basis), is preferably used.
  • the molar proportion of oxygen based on the total number of moles of hydrocarbon, oxygen and diluent gas, can be varied within a wide range.
  • the oxygen is preferably used in a molar deficit to the hydrocarbon.
  • a diluent gas such as nitrogen, helium, argon, methane, carbon dioxide, carbon monoxide or similar, predominantly inert gases, can optionally also be used for hydrocarbon and oxygen. Mixtures of the inert components described can also be used. The addition of inert components is favorable for transporting the heat released by this exothermic oxidation reaction and from a safety point of view. In this case, the composition of the educt gas mixtures described above is also possible into the explosion area, i.e. the relative ratio of hydrocarbon and oxygen can be between 0.5: 99.5 and 99.5: 0.5 mol%.
  • the contact time of the hydrocarbon and catalyst is usually in the range of 5-60 seconds.
  • the process is usually carried out at temperatures in the range of 120-300 ° C, preferably 180-250 ° C. Examples
  • One way of producing an active catalyst for PO production is, for example, to dissolve 77.6 mg of copper nitrate and 3.59 g of an approx. 14% ruthenium nitrosyl nitrate solution in 2 ml water, the solution to approx. 10 g Al 2 O 3 there and let it soak up. The solid thus obtained is dried overnight at 100 ° C. in a vacuum drying cabinet under a vacuum of approx. 15 mm Hg.
  • the precursor thus produced is reduced for 12 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.
  • One way to produce an active catalyst for PO production is to dissolve 77.6 mg of copper nitrate in 5-6 ml of water, add the solution to approx. 10 g of Al O 3 and let it soak up. The solid thus obtained is dried for 12 hours at 60 ° C. in a vacuum drying cabinet under a vacuum of approx.
  • the precursor thus produced is reduced for 12 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.
  • 10 g of the catalyst obtained in this way are investigated in a continuously operated fixed bed reactor with a residence time of about 20 seconds under a starting gas composition of 79% by volume propene and 21% by volume oxygen.
  • a starting gas composition of 79% by volume propene and 21% by volume oxygen.
  • One way of producing an active catalyst for PO production is, for example, to dissolve 77.6 mg of copper nitrate in 5-6 ml of water, add the solution to approx. 10 g of Al 2 O 3 and let it soak up. The solid obtained in this way is dried for 12 hours at 60 ° C. in a vacuum drying cabinet under a vacuum of approximately 15 mm Hg. Then 2.5 g of a ruthenium nitrosyl nitrate solution containing approximately 20% by weight of Ru are added in the same way and the mixture is dried then as described in Example 1. Finally, the precursor thus produced is reduced for 12 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.
  • Another way of producing an active catalyst for PO production is to add 7.4 g of a 10% rhodium nitrate solution to about 10 g of Al 2 O 3 and let it soak up. The solid thus obtained is dried for 4 hours at 100 ° C. in a vacuum drying cabinet under a vacuum of approx. 15 mm
  • Hg. 1.3 g of about 20% by weight are then coated in the same way.
  • Ru containing ruthenium butiitrosyl nitrate solution and then dries for 12 h as described in a vacuum drying cabinet.
  • the precursor thus produced is reduced for 4 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.
  • An alternative way of producing an active catalyst for PO production is, for example, to dissolve 343 mg of thalium nitrate in 5 g of water and to soak approx. 10 g of Al 2 O 3 with the resulting solution. The solution is allowed to be sucked up under constant agitation and the solid obtained in this way is dried for 4 h at 100 ° C. in a vacuum drying cabinet under a vacuum of approx. 15 mm Hg. The solution prepared from 776 mg of copper (II ) nitrate and 5 g water and then dries overnight at 100 ° C in a vacuum drying cabinet at approx. 15 mm Hg.
  • the precursor thus produced is reduced for 12 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.
  • the precursor thus produced is reduced for 12 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.
  • the precursor thus produced is reduced for 12 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.
  • 1 g of the catalyst obtained in this way is investigated in a continuously operated fixed bed reactor with a residence time of about 20 seconds under a feed gas composition of 79% by volume propene and 21% by volume oxygen.
  • a feed gas composition of 79% by volume propene and 21% by volume oxygen.
  • PO contents of 390 ppm are measured in the exhaust gas flow.
  • the precursor thus produced is reduced for 4 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.
  • the precursor thus produced is reduced for 8 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.
  • the precursor thus produced is reduced for 4 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.
  • the precursor thus produced is reduced for 8 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.
  • Solution 230 g Al 2 O 3 You let the solution soak up with constant movement and dries the solid obtained in this way for 4 hours at 100 ° C. in a vacuum drying cabinet under a vacuum of approx. 15 mm Hg. Then a solution prepared from 33.92 g of copper nitrate and 95 g of water is added in the same way and then dried overnight at 100 ° C in a vacuum drying cabinet at approx. 15 mm Hg.
  • the precursor thus produced is reduced for 8 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.
  • the precursor thus produced is reduced for 8 hours at 500 ° C. with 10% by volume H 2 in N 2 at 60 l / h.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé permettant d'époxyder des hydrocarbures avec de l'oxygène, qui se caractérise en ce que le procédé est mis en oeuvre en présence d'un mélange contenant au moins deux métaux du groupe comprenant Cu, Ru, Rh, Pd, Is, Ir, Pt, Au, In, Tl, Mn, Ce, sur un support de surface BET inférieure à 200 m2/g. L'invention concerne en outre l'utilisation d'un mélange contenant au moins deux métaux du groupe Cu, Ru, Rh, Pd, Os, Ir, Pt, Au, In, Tl, Mn, Ce, sur un support à surface BET inférieure à 200 m2/g pour époxyder des hydrocarbures.
EP01943326A 2000-05-18 2001-05-07 Procede pour epoxyder des hydrocarbures Withdrawn EP1286979A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10024096A DE10024096A1 (de) 2000-05-18 2000-05-18 Verfahren zur Epoxidierung von Kohlenwasserstoffen
DE10024096 2000-05-18
PCT/EP2001/005136 WO2001087867A1 (fr) 2000-05-18 2001-05-07 Procede pour epoxyder des hydrocarbures

Publications (1)

Publication Number Publication Date
EP1286979A1 true EP1286979A1 (fr) 2003-03-05

Family

ID=7642344

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01943326A Withdrawn EP1286979A1 (fr) 2000-05-18 2001-05-07 Procede pour epoxyder des hydrocarbures

Country Status (14)

Country Link
US (1) US20030191328A1 (fr)
EP (1) EP1286979A1 (fr)
JP (1) JP2003533520A (fr)
KR (1) KR20030009490A (fr)
CN (1) CN1429217A (fr)
AU (1) AU2001265930A1 (fr)
BR (1) BR0110850A (fr)
CA (1) CA2409018A1 (fr)
CZ (1) CZ20023733A3 (fr)
DE (1) DE10024096A1 (fr)
HU (1) HUP0302061A2 (fr)
MX (1) MXPA02011308A (fr)
PL (1) PL358336A1 (fr)
WO (1) WO2001087867A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10139531A1 (de) * 2001-08-10 2003-02-20 Bayer Ag Verfahren zur Epoxidierung von Kohlenwasserstoffen
DE10251325A1 (de) * 2002-11-05 2004-05-13 Bayer Ag Katalysator und Verfahren zur Oxidation von Kohlenwasserstoffen zu Epoxiden
JP2005306803A (ja) * 2004-04-23 2005-11-04 Hamamatsu Kagaku Gijutsu Kenkyu Shinkokai 不飽和化合物の酸化方法
TW200730243A (en) * 2005-12-15 2007-08-16 Mitsui Mining & Smelting Co Oxygen scavenger and method for producing the same
US8685883B2 (en) 2008-04-30 2014-04-01 Dow Technology Investments Llc Porous body precursors, shaped porous bodies, processes for making them, and end-use products based upon the same
US20110059843A1 (en) * 2008-04-30 2011-03-10 Howard Kevin E Porous body precursors, shaped porous bodies, processes for making them, and end-use products based upon the same
EP2293872A1 (fr) * 2008-04-30 2011-03-16 Dow Technology Investments LLC Précurseurs de corps poreux, corps façonnés poreux, procédés de fabrication de ceux-ci et produits finis fondés sur ceux-ci
US20110152547A1 (en) * 2009-12-17 2011-06-23 Sumitomo Chemical Company, Limited Process for producing olefin oxide
US8889892B2 (en) 2010-07-09 2014-11-18 Sumitomo Chemical Company, Limited Process for producing olefin oxide
WO2012094118A1 (fr) 2011-01-05 2012-07-12 Sumitomo Chemical Company, Limited Procédé de production d'un oxyde d'oléfine
EP2668170B1 (fr) * 2011-01-24 2016-10-19 Sumitomo Chemical Company Limited Conversion directe d'une oléfine en oxyde d'oléfine par de l'oxygène moléculaire
WO2013100173A1 (fr) 2011-12-27 2013-07-04 Sumitomo Chemical Company, Limited Procédé de production d'un oxyde d'oléfine faisant appel à un catalyseur comprenant un oxyde de ruthénium et un composant de tellure
WO2014003209A1 (fr) 2012-06-29 2014-01-03 Sumitomo Chemical Company, Limited Procédé de fabrication d'un oxyde d'oléfine

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US3989674A (en) * 1969-03-26 1976-11-02 Exxon Research And Engineering Company Novel gold-copper catalysts for the partial oxidation of olefins
GB1373489A (en) * 1970-11-09 1974-11-13 Ici Ltd Oxidation of olefinic compounds
GB1423339A (en) * 1972-03-13 1976-02-04 Ici Ltd Oxidation of olefins
GB1409421A (en) * 1972-07-17 1975-10-08 Bryce Smith Derek Gold compounds
US5112795A (en) * 1990-10-12 1992-05-12 Union Carbide Chemicals & Plastics Technology Corporation Supported silver catalyst, and processes for making and using same
DE4425672A1 (de) * 1994-07-20 1996-01-25 Basf Ag Oxidationskatalysator, Verfahren zu seiner Herstellung und Oxidationsverfahren unter Verwendung des Oxidationskatalysators
DE19519004A1 (de) * 1995-05-24 1996-11-28 Hoechst Ag Neue selen- und rutheniumhaltige Metalloxidkatalysatoren sowie ein Verfahren zu ihrer Herstellung und ihre Verwendung
KR100255480B1 (ko) * 1996-03-21 2000-05-01 사또 다께오 탄화수소의 부분산화용촉매 및 탄화수소의 부분산화방법
DE69704869T2 (de) * 1996-07-01 2001-08-30 The Dow Chemical Co., Midland Verfahren zur direkten oxidation von olefinen zu olefinoxiden
DE19845975A1 (de) * 1998-08-27 2000-03-02 Wolfgang Hoelderich Verfahren zur Herstellung von Epoxiden aus Olefinen und Sauerstoff in Gegenwart von Wasserstoff

Non-Patent Citations (1)

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Title
See references of WO0187867A1 *

Also Published As

Publication number Publication date
PL358336A1 (en) 2004-08-09
WO2001087867A1 (fr) 2001-11-22
DE10024096A1 (de) 2001-11-22
CN1429217A (zh) 2003-07-09
JP2003533520A (ja) 2003-11-11
MXPA02011308A (es) 2003-06-06
BR0110850A (pt) 2003-02-11
AU2001265930A1 (en) 2001-11-26
HUP0302061A2 (hu) 2003-09-29
KR20030009490A (ko) 2003-01-29
US20030191328A1 (en) 2003-10-09
CA2409018A1 (fr) 2002-11-15
CZ20023733A3 (cs) 2003-02-12

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