US20110152546A1 - Process for producing olefin oxide - Google Patents

Process for producing olefin oxide Download PDF

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Publication number
US20110152546A1
US20110152546A1 US12/826,445 US82644510A US2011152546A1 US 20110152546 A1 US20110152546 A1 US 20110152546A1 US 82644510 A US82644510 A US 82644510A US 2011152546 A1 US2011152546 A1 US 2011152546A1
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Prior art keywords
oxide
catalyst
copper
olefin
ruthenium
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US12/826,445
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English (en)
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Selim SENKAN
Anusorn Seubsai
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Priority to US12/826,445 priority Critical patent/US20110152546A1/en
Assigned to SUMITOMO CHEMICAL COMPANY, LIMITED reassignment SUMITOMO CHEMICAL COMPANY, LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SENKAN, SELIM, SEUBSAI, ANUSORN
Priority to KR1020127015627A priority patent/KR101763966B1/ko
Priority to EP10838192.2A priority patent/EP2513073B1/en
Priority to BR112012014674A priority patent/BR112012014674B1/pt
Priority to US13/516,226 priority patent/US8822372B2/en
Priority to JP2012532151A priority patent/JP2013505984A/ja
Priority to CN201080057846.9A priority patent/CN102933566B/zh
Priority to PCT/US2010/060185 priority patent/WO2011075458A1/en
Publication of US20110152546A1 publication Critical patent/US20110152546A1/en
Abandoned legal-status Critical Current

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    • 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
    • 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
    • B01J21/066—Zirconium or hafnium; 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • 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
    • 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
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

  • the present invention relates to a process for producing an olefin oxide.
  • Olefin oxides as for example propylene oxide, are amongst the most important chemicals widely used for the preparation of various textiles and plastics.
  • Several studies have intensively attempted to search for a process to obtain an olefin oxide with a high production rate hoping for an economically feasible plant design.
  • 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 and a ruthenium oxide on a porous support.
  • porous support comprises Al 2 O 3 , SiO 2 , TiO 2 or ZrO 2 .
  • a catalyst for producing an olefin oxide which comprises a copper oxide and a ruthenium oxide on a porous support.
  • FIG. 1 is a graph showing the result of Example 2, analysis (1).
  • FIG. 2 is a graph showing the result of Example 2, analysis (2).
  • FIG. 3 is a graph showing the result of Example 3, analysis (1).
  • FIG. 4 is a graph showing the result of Example 3, analysis (2).
  • FIG. 5 is a graph showing the result of Example 4, analysis (1).
  • FIG. 6 is a graph showing the result of Example 4, analysis (2).
  • FIG. 7 is a graph showing the powder X-ray diffraction patterns of Example 5.
  • the process of the present invention comprises reacting an olefin with oxygen in the presence of a catalyst comprising a copper oxide and a ruthenium oxide.
  • the copper oxide and the ruthenium oxide are supported on a porous support.
  • This catalyst is valuable for producing an olefin oxide, which is one aspect of the present invention.
  • the porous support has pores capable of supporting the copper oxide and the ruthenium oxide.
  • the porous support comprises preferably Al 2 O 3 , SiO 2 , TiO 2 or ZrO 2 , more preferably TiO 2 or SiO 2 , still more preferably SiO 2 .
  • Examples of the porous support comprising SiO 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 the copper oxide.
  • the 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 the ruthenium oxide.
  • the ruthenium oxide is usually composed of ruthenium and oxygen.
  • the ruthenium oxide examples include RuO 4 , and RuO 2 .
  • the ruthenium oxide is preferably RuO 2 .
  • the catalyst preferably comprises CuO and RuO 2 , because such metal oxides can contribute to improved olefin oxide selectivity.
  • the total content of the copper oxide and the ruthenium oxide is preferably 0.01 to 80% by weight of the amount of the catalyst. When the total content falls within such range, the olefin oxide yield and selectivity can be further improved.
  • 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, and still more preferably 30% by weight of the amount of the catalyst.
  • the copper/ruthenium metal weight ratio in the catalyst is 1/99 to 99/1.
  • the metal weight ratio falls within such a range, the olefin oxide selectivity can be further improved.
  • the lower limit of the metal weight ratio is more preferably 2/98, still more preferably 3/97.
  • the upper limit of the metal weight ratio is more preferably 98/2, still more preferably 97/3.
  • Production of the catalyst is not restricted to a specific process.
  • the catalyst is obtained by impregnating a porous support with a solution containing copper and ruthenium ions 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 solution containing copper and ruthenium ions can be prepared by dissolving a copper metal salt and a ruthenium metal salt in a solvent.
  • the copper metal salt include copper acetate, copper ammonium chloride, copper bromide, copper carbonate, copper ethoxide, copper hydroxide, copper iodide, copper isobutyrate, copper isopropoxide, copper oxalate, copper oxychroride, copper nitrates, and copper chlorides.
  • any of copper metal salts and ruthenium metal salts contains a halogen ion
  • the halogen ion may be presented in the obtained catalyst.
  • Such halogen ion presented in the catalyst may form salts or compounds with copper or ruthenium.
  • the solution may contain acidic or basic compounds in order to control its pH.
  • Examples of the solvent for the solution include water, alcohols such as methanol or ethanol, and ethers.
  • the total amount of the porous support is not limited to a specific range, preferably 20 to 99.99% by weight, more preferably 50 to 99.95% by weight, and more preferably 70 to 99.9% by weight of the amount of the catalyst.
  • the composition as prepared is preferably dried at a temperature of approximately 40 to approximately 200° C. before calcining it. Drying may be performed under an atmosphere of air or also under an inert gas atmosphere (for example Ar, N 2 , He) at standard pressure or reduced pressure.
  • the 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.
  • Calcining the composition is not limited, but it is preferably performed under a gas atmosphere containing oxygen.
  • a gas atmosphere containing oxygen examples include air and oxygen.
  • 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 gas, the composition or the like, however, a too high temperature may cause agglomeration of the ruthenium oxide and the copper oxide.
  • the calcination temperature is typically 200 to 800° C., preferably 400 to 600° C.
  • the catalyst can be used as powder, but it is usual to shape desired structures such as spheres, pellets, cylinders, rings or hollow cylinders, stars.
  • the catalyst can be shaped by a known procedure such as extrusion, ram extrusion, tableting.
  • the calcination is normally performed after shaping desired structures, but it can also be performed before shaping them.
  • olefins may have a linear or branched structure and contain usually 2 to 10, preferably 2 to 8 carbon atoms.
  • olefins include preferably ethylene, propylene, butene, pentene, hexene, heptene and octene, more preferably ethylene, propylene and butene, and still more preferably propylene.
  • the reaction is generally performed in the gas phase.
  • an olefin and oxygen may be fed respectively in the form of a gas.
  • An olefin and oxygen may also be fed in the form of their mixed gas.
  • Olefin and oxygen gases may be fed with diluent gases. Examples of the diluent gases include nitrogen or rare gases, such as argon and helium.
  • oxygen source pure oxygen may be used, or a mixed gas containing a gas inactive to the reaction, such as air, may be used.
  • 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, and more preferably 0.25 to 10 mol, with respect to 1 mol of an 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 reduced pressure to increased pressure.
  • Reduced pressure means a pressure lower than an atmospheric pressure.
  • Increased pressure means a pressure higher than atmospheric pressure.
  • the 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 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 the increased pressure.
  • the reactor type is not limited. Examples of 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 reactor 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 also be 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 oxide include preferably ethylene oxide, propylene oxide, butene oxide, pentene oxide, hexene oxide, heptene oxide and octene oxide, more preferably ethylene oxide, propylene oxide and butene oxide, and 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.
  • the detected products wore propylene oxide (PO), acetone (AT), acetaldehyde (AD), CO x (CO 2 and CO), and propanal+acrolein (PaL+AC).
  • PO propylene oxide
  • AT acetone
  • AD acetaldehyde
  • CO x CO 2 and CO
  • PaL+AC propanal+acrolein
  • PaL+AC are reported together since the two compounds appear at the same retention time, although the PaL is typically only found in trace amounts.
  • GC gas chromatography
  • X PR ⁇ [PO+AC+AT+2AD/3+CO 2 /3] out /[C 3 H 6 ] in ⁇ 100%;
  • Aqueous solutions of Ru [(NH 4 ) 2 RuCl 6 , Aldrich] and Cu [Cu(NO 3 ) 2 , Alfa Aesar, ACS, 98.0%-102.0%] were mixed at a metal weight ratio of 1:1, to prepare a metal salt solution.
  • the metal salt solution was introduced into a SiO 2 support powder (surface area 325 m 2 /g) and left to penetrate the support for 24 hours in the air.
  • the resulting material was collected from the solution, dried at 120° C. for 8 hours and calcined at 500° C. for 6 hours in the air to give a catalyst with a Cu/Ru metal weight ratio of 1/1 at the total metal loading of 5 wt %.
  • the catalyst (5.0 mg) was placed in a well of a reactor as mentioned in Angew. Chem. Int. Ed. 38 (1999) 2794, equipped with array microreactors, wells along each reactor channel and a passivated 200 micron ID capillary sampling probe within the reactor channel.
  • the mixture gas consisting of 14 vol % propylene (C 3 H 6 ), 26 vol % O 2 , and 60 vol % He was fed to the well at a gas hourly space velocity (GSHV) of 20,000 h ⁇ 1 with a mass flow controller (MKS, Andover, Mass.), at a reactor temperature of 250° C.
  • Gas sampling was accomplished by withdrawing reactor exit gases using the passivated 200 micron ID capillary sampling probe.
  • the result based on the analysis (1) is shown in FIG. 1 .
  • the result based on the analysis (2) is shown in FIG. 2 .
  • the results based on the analysis (1) are shown in FIG. 3 .
  • the results based on the analysis (2) are shown in FIG. 4 .
  • the mixture gas consisted of 2.5 vol. % propylene (C 3 H 6 ), 15 vol % O 2 , and 82.5 vol % He and the reaction temperature was 170, 190, 210, 230, 250, 270, 290 or 310° C.
  • the results based on the analysis (1) are shown in FIG. 5 .
  • the results based on the analysis (2) are shown in FIG. 6 .
  • a powder X-ray diffraction (XRD) pattern of the catalyst obtained in Example 1 was determined with PANalytical X'Pert PRO fitted with a Ni filter and a Seller slit collimator.
  • the Cu—K ⁇ radiation at 45 kV and 40 mA was used to identify the active catalyst phases.
  • the following metal compounds as supported on SiO 2 were prepared and examined in the same manner as above: CuO (Cu content, 3.6 wt % of the total of CuO and SiO 2 ) supported on SiO 2 which was prepared from Cu(NO 3 ) 2 ; and RuO 2 (Ru content, 7.2 wt % of the total of RuO 2 and SiO 2 ) supported on SiO 2 which was prepared from (NH 4 ) 2 RuCl 6 .
  • the XRD patterns are shown in FIG. 7 .
  • the XRD pattern of the catalyst shows that it comprises CuO and RuO 2 without forming any crystalline mixed metal oxides or alloys.
  • a catalyst is prepared in the same manner as Example 1, except that TiO 2 is used instead of SiO 2 .
  • Production of propylene oxide is carried out in the same manner as Example 1 except that the catalyst is used.

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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US12/826,445 2009-12-17 2010-06-29 Process for producing olefin oxide Abandoned US20110152546A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US12/826,445 US20110152546A1 (en) 2009-12-17 2010-06-29 Process for producing olefin oxide
KR1020127015627A KR101763966B1 (ko) 2009-12-17 2010-12-14 산화올레핀의 제조 방법
EP10838192.2A EP2513073B1 (en) 2009-12-17 2010-12-14 Process for producing olefin oxide
BR112012014674A BR112012014674B1 (pt) 2009-12-17 2010-12-14 Process for the production of olefin oxide, catalyst, and its use
US13/516,226 US8822372B2 (en) 2009-12-17 2010-12-14 Process for producing olefin oxide
JP2012532151A JP2013505984A (ja) 2009-12-17 2010-12-14 酸化オレフィンの製造方法
CN201080057846.9A CN102933566B (zh) 2009-12-17 2010-12-14 制备烯烃氧化物的方法
PCT/US2010/060185 WO2011075458A1 (en) 2009-12-17 2010-12-14 Process for producing olefin oxide

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US28432409P 2009-12-17 2009-12-17
US12/826,445 US20110152546A1 (en) 2009-12-17 2010-06-29 Process for producing olefin oxide

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US12/826,458 Abandoned US20110152547A1 (en) 2009-12-17 2010-06-29 Process for producing olefin oxide
US13/516,222 Abandoned US20120283454A1 (en) 2009-12-17 2010-12-14 Process for producing olefin oxide
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US13/516,226 Expired - Fee Related US8822372B2 (en) 2009-12-17 2010-12-14 Process for producing olefin oxide

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JP (2) JP2013505985A (pt)
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CN (2) CN102933566B (pt)
BR (2) BR112012017167A2 (pt)
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Cited By (6)

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WO2013025315A1 (en) * 2011-08-17 2013-02-21 Sumitomo Chemical Company, Limited Process for producing olefin oxide
WO2013025316A1 (en) * 2011-08-17 2013-02-21 Sumitomo Chemical Company, Limited Process for producing olefin oxide
US8765981B2 (en) 2011-01-05 2014-07-01 Sumitomo Chemical Company, Limited Process for producing olefin oxide
EP3117898A1 (de) * 2015-07-15 2017-01-18 i2 Gesellschaft für Innovation mbH Herstellung eines mischkatalysators
WO2018234045A1 (en) * 2017-06-23 2018-12-27 Haldor Topsøe A/S PROCESS FOR OXIDATION OF LOWER-TEMPERATURE LOWER ALKENO IN GASEOUS MIXTURES CONTAINING AMMONIA
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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US20110152546A1 (en) * 2009-12-17 2011-06-23 Sumitomo Chemical Company, Limited Process for producing olefin oxide
BR112013017785B1 (pt) 2011-01-24 2018-10-09 Sumitomo Chemical Co processo para produzir um óxido de olefina por meio do oxigênio molecular
WO2013062791A1 (en) * 2011-10-24 2013-05-02 Sumitomo Chemical Company, Limited Process for producing olefin oxide
WO2014003209A1 (en) * 2012-06-29 2014-01-03 Sumitomo Chemical Company, Limited Process for producing olefin oxide
WO2016153969A1 (en) 2015-03-20 2016-09-29 Northwestern University Catalysts and related methods for photocatalytc production of h2o2 and thermocatalytic reactant oxidation
CN106732593B (zh) * 2016-12-30 2019-11-22 天津市长芦化工新材料有限公司 铜基固相催化剂及其制备方法和应用
US10800981B2 (en) 2019-02-13 2020-10-13 Saudi Arabian Oil Company Process for producing diesel fuel from olefinic refinery feedstreams
WO2021126947A1 (en) * 2019-12-16 2021-06-24 Calera Corporation Electrochemical, bromination, and oxybromination systems and methods to form propylene oxide or ethylene oxide

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US8765981B2 (en) 2011-01-05 2014-07-01 Sumitomo Chemical Company, Limited Process for producing olefin oxide
WO2013025315A1 (en) * 2011-08-17 2013-02-21 Sumitomo Chemical Company, Limited Process for producing olefin oxide
WO2013025316A1 (en) * 2011-08-17 2013-02-21 Sumitomo Chemical Company, Limited Process for producing olefin oxide
EP3117898A1 (de) * 2015-07-15 2017-01-18 i2 Gesellschaft für Innovation mbH Herstellung eines mischkatalysators
WO2018234045A1 (en) * 2017-06-23 2018-12-27 Haldor Topsøe A/S PROCESS FOR OXIDATION OF LOWER-TEMPERATURE LOWER ALKENO IN GASEOUS MIXTURES CONTAINING AMMONIA
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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EP2513073B1 (en) 2015-08-05
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US8822372B2 (en) 2014-09-02
BR112012017167A2 (pt) 2019-09-24

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