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WO2012009052A1 - Procédé de production d'oxyde oléfinique - Google Patents

Procédé de production d'oxyde oléfinique Download PDF

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Publication number
WO2012009052A1
WO2012009052A1 PCT/US2011/038173 US2011038173W WO2012009052A1 WO 2012009052 A1 WO2012009052 A1 WO 2012009052A1 US 2011038173 W US2011038173 W US 2011038173W WO 2012009052 A1 WO2012009052 A1 WO 2012009052A1
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WO
WIPO (PCT)
Prior art keywords
oxide
catalyst
alkaline
alkaline earth
earth metal
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.)
Ceased
Application number
PCT/US2011/038173
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English (en)
Inventor
Yoshihiko Ohishi
Anusorn Seubsai
Selim Senkan
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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 Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP2012532154A priority Critical patent/JP2013505987A/ja
Publication of WO2012009052A1 publication Critical patent/WO2012009052A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • B01J23/83—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 rare earths or actinides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • 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
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation

Definitions

  • the present invention relates to a process for producing an olefin oxide.
  • Olefin oxides such as propylene oxide
  • the present invention provides:
  • a process for producing an olefin oxide which comprises reacting an olefin with oxygen in the presence of a catalyst comprising (a) copper oxide, (b) lanthanoid oxide and (c) alkaline metal component or alkaline earth metal component.
  • lanthanoid oxide (b) alkaline metal component or alkaline earth metal component and (d) halogen component are supported on a porous support.
  • alkaline metal component or alkaline earth metal component is 0.01 to 80% by weight of the amount of the catalyst.
  • (a) copper oxide is CuO.
  • lanthanoid oxide is cerium oxide.
  • a catalyst for production of an olefin oxide which comprises (a) copper oxide, (b) lanthanoid oxide and (c) alkaline metal component or alkaline earth metal component.
  • alkaline metal component or alkaline earth metal component is an alkaline metal-containing compound or an alkaline earth metal-containing compound.
  • a catalyst for producing an olefin oxide comprising (a) copper oxide, (b) lanthanoid oxide and
  • the process of the present invention comprises reacting an olefin with oxygen in the presence of a catalyst comprising (a) copper oxide, (b) lanthanoid oxide and (c) alkaline metal component or alkaline earth metal component.
  • the components (a) , (b) and (c) may be supported on a porous support or a non-porous support.
  • the non-porous support include a non-porous support comprising SiC ⁇ such as CAB-O-SIL (registered trademark) .
  • the components (a) , (b) and (c) are preferably supported on a porous support. This catalyst is valuable for production of olefin oxides, which is one aspect of the present invention.
  • the porous support has pores capable of supporting the components (a) , (b) and (c) .
  • the porous support comprises preferably AI2O3, S1O2, T1O2 or ZrC>2, more preferably SiC>2.
  • Examples of the porous support comprising Si0 2 include mesoporous silica.
  • Such a porous support may also comprise zeolites .
  • olefin oxides can be prepared with good yield and good selectivity.
  • the catalyst may comprise one or more kinds of (a) copper oxide.
  • the (a) copper oxide is usually composed of copper and oxygen. Examples of the copper oxide include CU 2 O and CuO.
  • the copper oxide is preferably CuO.
  • the catalyst may comprise one or more kinds of (b) lanthanoid oxide.
  • the component (b) is usually composed of lanthanoid and oxygen.
  • the component (b) oxide include lanthanum oxide, cerium oxide, praseodymium oxide, neodymium oxide, promethium oxide, samarium oxide, europium oxide, gadolinium oxide, terbium oxide, dysprosium oxide, holmium oxide, erbium oxide, thulium oxide, ytterbium oxide and lutetium oxide, preferably lanthanum oxide, cerium oxide, samarium oxide and gadolinium oxide, more preferably LaO, La 2 0 3 , Ce203, Ce0 2 , Sm 2 0 3 and Gd 2 0 3 , still more preferably Ce0 2 .
  • the catalyst may comprise one or more kinds of (c) alkaline metal component or alkaline earth metal component.
  • the component (c) may be an alkaline metal-containing compound, an alkaline earth metal-containing compound, an alkaline metal ion or an alkaline earth metal ion.
  • Examples of the alkaline metal-containing compound include compounds containing an alkaline metal such as Na, K, Rb and Cs .
  • Examples of the alkaline earth metal-containing compound include compounds containing an alkaline earth metal such as Ca, Mg, Sr and Ba .
  • Examples of the alkaline metal ion include Na + , K + , Rb + and Cs + .
  • Examples of the alkaline earth metal ion include Ca 2+ , Mg 2+ , Sr 2+ and Ba 2+ .
  • the alkaline metal component may be an alkaline metal oxide .
  • the alkaline metal oxide include Na 2 0, Na 2 0 2 , K 2 0, K0 2 , K 2 0 2 , Rb 2 0, Rb 2 0 2 , Cs 2 0, Cs 2 0 2 , Cs0 2 , Cs0 3 , Cs 2 0 3 , Csu0 3 , CS O and CS 7 O.
  • the alkaline earth metal component may be alkaline metal earth oxide. Examples of the alkaline earth metal oxide include CaO, Ca0 2 , MgO, Mg0 2 , SrO, Sr0 2 , BaO and Ba0 2 .
  • the alkaline metal-containing compound is preferably an alkaline metal salt.
  • the alkaline earth metal-containing compound is preferably an alkaline earth metal salt.
  • the alkaline metal salt comprises the alkaline metal ion as mentioned above with an anion.
  • the alkaline earth metal salt comprises the alkaline earth metal ion as mentioned above with an anion. Examples of anions in such salts include F ⁇ , Cl ⁇ , Br “ , I “ , OH “ , N0 3 “ , S0 4 2” , CO3 2” , HCO3 " and S0 3 2" .
  • Such salts are preferably an alkaline metal salt with a halogen, such as an alkaline metal halide, or an alkaline earth metal-containing salt with a halogen, such as an alkaline earth metal halide, more preferably an alkaline metal salt with a halogen, still more preferably an alkaline metal chloride.
  • the component (c) is preferably an alkaline
  • metal-containing compound or an alkaline earth
  • metal-containing compound more preferably a
  • the catalyst comprises NaCl as the (c) component, it can show excellent olefin oxide selectivity.
  • the copper/lanthanoid metal molar ratio in the catalyst is preferably 1/99 to 99/1. When the metal molar ratio falls within such a range, the olefin oxide yield and selectivity can be further improved.
  • the lower limit of the molar ratio is more preferably 2 / 98 , still more preferably 3/ 97 , further preferably 10/90, particularly preferably 20/80.
  • the upper limit of the molar ratio is more preferably 98/2, still more preferably 97/3, further preferably 90/10, particularly preferably 80/20.
  • the copper/ (c) component molar ratio in the catalyst is preferably 1/99 to 99/1. When the molar ratio falls within such a range, the olefin oxide yield and selectivity can be further improved.
  • the lower limit of the molar ratio is more preferably 2/98, still more preferably 3/97.
  • the upper limit of the molar ratio is more preferably 98/2, still more preferably 97/3.
  • the " (c) component" of the molar ratio represents the alkaline metal or alkaline earth metal existing in the (c) component and the alkaline metal or alkaline earth metal ion existing in the (c) component .
  • the total content of the components (a) , (b) and (c) is preferably 0.01 to 80% by weight of the amount of the catalyst.
  • the lower limit of the total content is more preferably 0.05% by weight, still more preferably 0.1% by weight of the amount of the catalyst.
  • the upper limit of the total content is more preferably 50% by weight, still more preferably 30% by weight of the amount of the catalyst.
  • the catalyst may comprise (d) halogen component besides the components (a) , (b) and (c) .
  • the component (d) is generally a halogen-containing compound. Examples of the halogen include chlorine, fluorine, iodine and bromine.
  • halogen-containing compound examples include copper halides such as CuCl and CUCI 2 ; lanthanoid halides such as lanthanum halides, cerium halides, praseodymium halides, neodymium halides, promethium halides, samarium halides, europium halides, gadolinium halides, terbium halides, dysprosium halides, holmium halides, erbium halides, thulium halides, ytterbium halides and lutetium halides, preferably lanthanum halides, cerium halides, samarium halides and gadolinium halides, more preferably LaCl 3 , CeCl 3 , SmCl 3 , GdCl 3 ; copper oxyhalides such as CUOCI 2 , CUCIO 4 , CIO 2 CU (CIO 4 )
  • neodymium oxyhalide promethium oxyhalide, samarium oxyhalide, europium oxyhalide, gadolinium oxyhalide, terbium oxyhalide, dysprosium oxyhalide, holmium oxyhalide, erbium oxyhalide, thulium oxyhalide, ytterbium oxyhalide and lutetium oxyhalide, preferably lanthanum oxyhalide, cerium oxyhalide, samarium oxyhalide and gadolinium oxyhalide, more preferably LaOCl, La(C10 4 ) 3 , CeOCl, Ce(C10 4 ) 3 , SmOCl, Sm(C10 4 ) 3 , GdOCl, Gd(C10 4 ) 3 .
  • the component (d) may be supported on any of the components (a) , (b) and (c) or the porous support.
  • the catalyst may further comprise (e) composite oxides including those composed of copper, lanthanoid and oxygen such as CuLa2C>4, Cu 7 La80ig, LaCuC>3, CuLaC>2, CuCeC>2, CuCeC>3, CuSmCb, CuSrri 2 0 and CuGd 2 0 , those composed of sodium, lanthanoid and oxygen, such as aLa0 2 , aCe0 2 , aSm0 2 and aGd0 2 , and those composed of copper, sodium and oxygen, such as aCu0 2 , a 2 Cu0 2 , NaCuO and Na 6 Cu 2 0 6 .
  • composite oxides including those composed of copper, lanthanoid and oxygen such as CuLa2C>4, Cu 7 La80ig, LaCuC>3, CuLaC>2, CuCeC>2, CuCeC>3, CuSmCb, CuSrri 2 0 and CuGd 2 0 , those composed of sodium, lant
  • the catalyst comprises the component (d) or (e)
  • the component may be supported on the porous support as mentioned above .
  • Production of the catalyst is not restricted to a specific process, examples of which include the conventional methods.
  • the catalyst can be obtained by impregnating a porous support with a solution containing a copper ion, a lanthanoid ion and an alkaline metal or alkaline earth metal ion to prepare a composition, followed by calcining the composition.
  • the support can be in form of powder, or shaped to a desired structure as necessary.
  • the catalyst comprises the component (c) which is an alkaline metal salt with a halogen or alkaline earth metal salt with a halogen, and the component (d) supported on the porous support, the catalyst can be obtained in the same procedure as mentioned above except that the solution contains a copper ion, a lanthanoid ion, an alkaline metal or alkaline earth metal-containing ion and a halogen ion.
  • the solution containing a copper ion, a lanthanoid ion and an alkaline metal or alkaline earth metal ion can be prepared by dissolving a copper metal salt or a copper oxide, a lanthanoid metal salt or a lanthanoid oxide, and an alkaline metal or alkaline earth metal salt or an alkaline metal or alkaline earth metal oxide in a solvent.
  • the solution is preferably prepared by dissolving a copper metal salt, a lanthanoid metal salt and an alkaline metal or alkaline earth metal salt in a solvent.
  • Examples of the copper metal salt include copper acetate, copper ethoxide, copper isobutyrate, copper isopropoxide, copper hydroxide, copper nitrate, copper sulfate, copper chloride, copper diammonium chloride, copper bromide and copper iodide.
  • Examples of the lanthanoid metal salt include lanthanoid sulfate, lanthanoid nitrate, and lanthanoid halide such as lanthanoid bromide, lanthanoid chloride and lanthanoid iodide .
  • the alkaline metal or alkaline earth metal salt for the solution may be the same as or different from the salt of the (c) component in the catalyst.
  • the alkaline metal or alkaline earth metal salt include alkaline metal nitrates, alkaline earth metal nitrates , alkaline metal halides , alkaline earth metal halides, alkaline metal acetates, alkaline earth metal acetates, alkaline metal butyrates, alkaline earth metal butyrates, alkaline metal benzoates, alkaline earth metal benzoates, alkaline metal alkoxides, alkaline earth metal alkoxides, alkaline metal carbonates, alkaline earth metal carbonates, alkaline metal citrates, alkaline earth metal citrates, alkaline metal formates, alkaline earth metal formates, alkaline metal hydrogen carbonates, alkaline earth metal hydrogen carbonates, alkaline earth metal hydrogen carbonates, alkaline metal hydroxides, alkaline earth metal hydrox
  • At least one of the metal salts for the solvent contains preferably a halogen ion, more preferably a chloride ion.
  • a halogen ion may form the (c) components such as alkaline metal halides or alkaline earth metal halides, or the (d) components such as copper halides and oxyhalides and lanthanoid halides and oxyhalides.
  • the solution may contain acidic or basic compounds in order to control its pH.
  • Examples of the solvent for the solution include water and alcohols such as methanol or ethanol.
  • the total amount of the porous support is preferably 20 to 99.99% by weight, more preferably 50 to 99.95% by weight, still preferably 70 to 99.9% by weight of the catalyst as obtained .
  • the composition as prepared by the impregnation is usually dried, and the drying method thereof is not limited.
  • the composition as prepared by the impregnation is preferably dried at a temperature of approximately 40°C to approximately 200°C before calcining the composition. Drying is preferably performed under an atmosphere of air or also under an inert gas atmosphere (for example, Ar, 2, He) at standard pressure or reduced pressure .
  • a drying time is preferably in the range from 0.5 to 24 hours. After drying, the composition can be shaped to a desired structure as necessary.
  • the method of calcining the composition is not limited, and calcining the composition is preferably performed under a gas atmosphere containing oxygen.
  • a gas atmosphere containing oxygen examples include air, oxygen, nitrous oxide and other oxidizing gases.
  • the gas may be used after being mixed at an appropriate ratio with a diluting gas such as nitrogen, helium, argon, and water vapor.
  • An optimal temperature for calcination varies depending on the kind of the gas and the composition, however, a too high temperature may cause agglomeration of lanthanoid oxide and copper oxide. Accordingly, the calcination temperature is typically 200 to 800°C, preferably at 400 to 600°C.
  • the catalyst can be used as powder, but it is usual to shape it into desired structures such as spheres, pellets, cylinders, rings, hollow cylinders, or stars.
  • the catalyst can be shaped by a known procedure such as extrusion, ram extrusion, tableting.
  • the calcination is normally performed after shaping into the desired structures, but it can also be performed before shaping them.
  • the olefin may have a linear or branched structure and contains usually 2 to 10, preferably 2 to 8 carbon atoms.
  • the olefin include preferably ethylene, propylene, butene, pentene, hexene, heptene, octene, and butadiene, more preferably ethylene, propylene, and butene, still more preferably propylene.
  • the reaction is generally performed in the gas phase.
  • the olefin and oxygen may be fed respectively in the form of a gas.
  • Olefin and oxygen gases can be fed in the form of their mixed gas.
  • Olefin and oxygen gases may be fed with diluent gases.
  • diluent gases include nitrogen, rare gases such as argon and helium, carbon dioxide, water vapor, methane, ethane and propane.
  • Preferable diluent gases are nitrogen, carbon dioxide and the both thereof.
  • oxygen source pure oxygen may be used, or a mixed gas containing pure oxygen and a gas inactive to the reaction, such as the air, may be used.
  • gas inactive to the reaction include nitrogen, rare gases such as argon and helium, carbon dioxide, water vapor, methane, ethane and propane.
  • gases inactive to the reaction are nitrogen, carbon dioxide and the both thereof.
  • the amount of oxygen used varies depending on the reaction type, the catalyst, the reaction temperature or the like.
  • the amount of oxygen is typically 0.01 to 100 mol, and preferably 0.03 to 30 mol, more preferably 0.05 to 10 mol and especially preferably 0.25 to 10 mol, with respect to 1 mol of the olefin.
  • the reaction is performed at a temperature generally of 100 to 350°C, preferably of 120 to 330°C, more preferably of 170 to 310°C.
  • the present reaction is carried out under reaction pressure in the range of reduced pressure to increased pressure .
  • Reduced pressure means a pressure lower than atmospheric pressure.
  • Increased pressure means a pressure higher than atmospheric pressure.
  • the reaction pressure is typically in the range of 0.01 to 3 MPa, and preferably in the range of 0.02 to 2 MPa, in the absolute pressure.
  • the reaction of the present invention may be carried out as a batch reaction or a continuous reaction, preferably as a continuous reaction for industrial application.
  • the reaction of the present invention may be carried out by mixing an olefin and oxygen and then contacting the mixture with the catalyst under reduced pressure to increased pressure.
  • the reactor type is not limited. Examples of the reactor types are fluid bed reactor, fixed bed reactor, moving bed reactor, and the like, preferably fixed bed reactor. In the case of using fixed bed reactor, single tube reactor or multi tube reactor can be employed. More than one reactors can be used. If the number of reactors is large, small reactors as for example microreactors , can be used, which can have multiple channels. Adiabatic type or heat exchange type may be also used.
  • the olefin oxide may have a linear or branched structure and contains usually 2 to 10, preferably 2 to 8 carbon atoms.
  • the olefin oxides include preferably ethylene oxide, propylene oxide, butene oxide, pentene oxide, hexene oxide, heptene oxide, octene oxide, and 3, 4-epoxy-l-butene, more preferably ethylene oxide, propylene oxide, and butene oxide, still more preferably propylene oxide.
  • the olefin oxide as obtained can be collected by a method known in the art such as separation by distillation. Examples
  • a reaction gas was mixed with ethane (10 Nml/min) as an external standard, and then directly introduced in the TCD-GC equipped with a column of Gaskuropack 54 (2 m) . All products in the reaction gas were collected for 1 hour with double methanol traps connected in series and cooled with a dry-ice/methanol bath. The two methanol solutions were mixed together and added to anisole as an external standard, and then analyzed with two FID-GCs quipped with different columns, PoraBOND U (25 m) and PoraBOND Q (25 m) .
  • the detected products were propylene oxide (PO) , acetone (AT), CO x (C0 2 and CO), propanal (PaL) , acrolein (AC)
  • a catalyst was prepared by a co-impregnation method.
  • a predetermined weight (1.9 g) of amorphous silica powder (S1O 2 , Japan Aerosil , 380 m 2 /g) was added to an aqueous solution mixture containing 0.28 g of LaCl 3 (Wako) , 0.30 g of Cu (N0 3 ) 2 (Wako) and 0.10 g of NaCl (Wako), followed by stirring the mixture for 24 hours in the air to impregnate the support with the metal salts.
  • the resulting material was then heated at 100°C until dried, and calcined at 500°C for 12 hours in air to give a catalyst.
  • the catalyst was evaluated by using a fixed-bed reactor. Filling a 1/2-inch OD reaction tube made of stainless steel with 1 mL of the thus obtained catalyst, the reaction tube was supplied with 450 NmL/h of propylene, 900 NmL/h of air, and 990 NmL/h of nitrogen gas to carry out the reaction at the reaction temperature of 200, 250 and 270°C under increased pressure (equivalent to 0.3 MPa in the absolute pressure) .
  • the preparation and the reaction were conducted in the same manner as Example 1, except that the preparation was conducted using 0.58 g of CeC]_3 (Wako) , 0.41 g of Cu (NO 3 ) 2 (Wako) , 0.20 g of a 0 3 (Wako) and 2.7 g of an amorphous silica powder (S1O2, Japan Aerosil, 380 m 2 /g) as raw materials.
  • the preparation and the reaction were conducted in the same manner as Example 1, except that the preparation was conducted using 0.40 g of SmCl 3 (Wako) , 0.45 g of Cu (N0 3 ) 2 (Wako) , 0.15 g of NaCl (Wako) and 2.9 g of an amorphous silica powder
  • the preparation and the reaction were conducted in the same manner as Example 1, except that the preparation was conducted using 0.40 g of GdCl 3 (Wako) , 0.45 g of Cu (N0 3 ) 2 (Wako) , 0.15 g of NaCl (Wako) and 2.9 g of an amorphous silica powder (SiC>2, Japan Aerosil, 380 m 2 /g) as raw materials.
  • Example 1 The catalyst obtained in Example 1 (5.0 mg) was placed in a well of a reactor as mentioned in Angew. Chem. Int. Ed.
  • the detected products were propylene oxide (PO) , acetone (AT) , acetaldehyde (AD) , CO x (C0 2 and CO) , and propanal + acrolein (PaL+AC) .
  • Example 2 The catalyst obtained in Example 2 was tested in the same manner as Example 5.
  • Example 3 The catalyst obtained in Example 3 was tested in the same manner as Example 5.
  • Example 4 The catalyst obtained in Example 4 was tested in the same manner as Example 5.

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  • Engineering & Computer Science (AREA)
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Abstract

L'invention concerne un procédé de production d'un oxyde oléfinique qui consiste à faire réagir une oléfine avec de l'oxygène en présence d'un catalyseur comprenant: (a) de l'oxyde de cuivre, (b) de l'oxyde de lanthanide et (c) un composant de métal alcalin ou un composant de métal alcalino-terreux.
PCT/US2011/038173 2010-07-10 2011-05-26 Procédé de production d'oxyde oléfinique Ceased WO2012009052A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2012532154A JP2013505987A (ja) 2010-07-10 2011-05-26 酸化オレフィンの製造方法

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US36322710P 2010-07-10 2010-07-10
US61/363,227 2010-07-10

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102909023A (zh) * 2012-09-14 2013-02-06 广州市卫斯理日化实业有限公司 汽车尾气催化剂及其制备方法
WO2018234045A1 (fr) * 2017-06-23 2018-12-27 Haldor Topsøe A/S Procédé d'oxydation d'un alcène inférieur à basses températures dans des mélanges gazeux contenant de l'ammoniac
US10941093B2 (en) 2017-06-23 2021-03-09 Haldor Topsøe A/S Process for oxidation of a lower alkane at low temperatures in ammonia-containing gas mixtures

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US4388225A (en) * 1981-01-23 1983-06-14 Phillips Petroleum Company Olefin oxidation with supported CuO catalyst
EP0480537A1 (fr) * 1990-10-12 1992-04-15 Union Carbide Chemicals And Plastics Company, Inc. Catalyseurs stables d'alkylène oxyde
US5112795A (en) * 1990-10-12 1992-05-12 Union Carbide Chemicals & Plastics Technology Corporation Supported silver catalyst, and processes for making and using same
US5958824A (en) * 1997-09-02 1999-09-28 Scientific Design Co., Inc. Ethylene oxide catalyst
US6498259B1 (en) * 2001-10-19 2002-12-24 Arco Chemical Technology L.P. Direct epoxidation process using a mixed catalyst system
US6765101B1 (en) * 2001-05-01 2004-07-20 Union Carbide Chemicals & Plastics Technology Corporation Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4388225A (en) * 1981-01-23 1983-06-14 Phillips Petroleum Company Olefin oxidation with supported CuO catalyst
EP0480537A1 (fr) * 1990-10-12 1992-04-15 Union Carbide Chemicals And Plastics Company, Inc. Catalyseurs stables d'alkylène oxyde
US5112795A (en) * 1990-10-12 1992-05-12 Union Carbide Chemicals & Plastics Technology Corporation Supported silver catalyst, and processes for making and using same
US5958824A (en) * 1997-09-02 1999-09-28 Scientific Design Co., Inc. Ethylene oxide catalyst
US6765101B1 (en) * 2001-05-01 2004-07-20 Union Carbide Chemicals & Plastics Technology Corporation Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes
US6498259B1 (en) * 2001-10-19 2002-12-24 Arco Chemical Technology L.P. Direct epoxidation process using a mixed catalyst system

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102909023A (zh) * 2012-09-14 2013-02-06 广州市卫斯理日化实业有限公司 汽车尾气催化剂及其制备方法
WO2018234045A1 (fr) * 2017-06-23 2018-12-27 Haldor Topsøe A/S Procédé d'oxydation d'un alcène inférieur à basses températures dans des mélanges gazeux contenant de l'ammoniac
CN110770215A (zh) * 2017-06-23 2020-02-07 托普索公司 在低温下在含氨的气体混合物中氧化低级烯烃的方法
US10941093B2 (en) 2017-06-23 2021-03-09 Haldor Topsøe A/S Process for oxidation of a lower alkane at low temperatures in ammonia-containing gas mixtures
US10954205B2 (en) 2017-06-23 2021-03-23 Haldor Topsøe A/S Process for oxidation of a lower alkene at low temperatures in ammonia-containing gas mixtures

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