WO2006094746A1 - Catalyseur d'acetoxylation d'hydrocarbures c2-c9 - Google Patents

Catalyseur d'acetoxylation d'hydrocarbures c2-c9 Download PDF

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Publication number
WO2006094746A1
WO2006094746A1 PCT/EP2006/002041 EP2006002041W WO2006094746A1 WO 2006094746 A1 WO2006094746 A1 WO 2006094746A1 EP 2006002041 W EP2006002041 W EP 2006002041W WO 2006094746 A1 WO2006094746 A1 WO 2006094746A1
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catalyst
metal
magnesium
acetoxylation
containing oxide
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PCT/EP2006/002041
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German (de)
English (en)
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Stephan Andreas Schunk
Christian Baltes
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Hte Aktiengesellschaft
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Publication of WO2006094746A1 publication Critical patent/WO2006094746A1/fr

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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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • 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
    • B01J23/58—Platinum group metals with alkali- or alkaline earth 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
    • B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/644—Arsenic, antimony or bismuth
    • B01J23/6445—Antimony
    • 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
    • B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/644—Arsenic, antimony or bismuth
    • B01J23/6447—Bismuth
    • 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
    • B01J23/66—Silver or gold
    • B01J23/68—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/681—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with arsenic, antimony or bismuth
    • 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
    • B01J23/8933—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 also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/8973—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 also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony or bismuth
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
    • C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
    • C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
    • 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
    • B01J21/14—Silica and magnesia

Definitions

  • the invention relates to a catalyst containing at least one metal from the platinum group, another metal or semimetal and an alkali or alkaline earth metal, wherein the metals and / or their oxidized forms are applied to a magnesium-containing support material.
  • a catalyst containing at least one metal from the platinum group, another metal or semimetal and an alkali or alkaline earth metal, wherein the metals and / or their oxidized forms are applied to a magnesium-containing support material.
  • Pd, K and Bi or Pd, K and Bi are used together with Pt.
  • Further objects of the invention are a process for the preparation of the catalyst and the use of the catalyst for the acetoxylation of C 2 -C 9 -hydrocarbons in the gas phase, preferably of olefins or alkylaromatics, but especially of butadiene.
  • Another object of the invention is the use of magnesium-containing oxides in the acetoxylation of C 2 -C 9 hydrocarbons.
  • the catalysts used here as a rule consist of the components K and Pd and one or more further elements which are applied to a suitable support material.
  • DE 154 22 57 discloses the preparation of vinyl acetate in the gas phase with the aid of palladium-containing solid catalysts which, in addition to the palladium, may optionally contain one further metal component from the group copper, silver, gold, ruthenium, rhodium, osmium, iridium or platinum.
  • the preparation of the catalysts via the deposition of the active component or the active components on an oxidic support, which is mixed with alkali metal salt solution in the further course of treatment.
  • GB 1 215 210 discloses a catalyst for the preparation of unsaturated esters, for example vinyl acetate, by a gas phase process.
  • unsaturated esters for example vinyl acetate
  • carboxylic acids are catalytically reacted in the presence of oxygen in high yields to the corresponding ester compounds.
  • the preparation of the catalyst is based on an entry of palladium and platinum components on a support of inert material and the subsequent treatment of the loaded support material with alkali metal-containing or alkaline earth metal-containing compounds as activators, for example potassium acetate and sodium acetate.
  • US Pat. No. 5,342,987 discloses catalysts based on the active components palladium, gold and potassium which are suitable for the preparation of alkenylalkanoates.
  • a particularly low sodium content of the catalysts used is given.
  • the carrier should have a capability to exchange ions so that excess sodium species can be removed as completely as possible from the catalyst.
  • the lowering of the sodium content is carried out by the treatment of the catalyst with salt solutions containing, for example, lithium, potassium, ammonium or magnesium ions.
  • Suitable carriers appear to be conventional aluminosilicates and preferably conventional silicates which have a high BET surface area.
  • the object was to provide further catalysts for acetoxylation reactions, with which high selectivities can be achieved with good yields of acetoxylation even at high conversions.
  • a catalyst comprising a metal from the platinum group, another metal or semimetal, an alkali or alkaline earth metal and / or their oxidized forms and a magnesium-containing oxide.
  • transition metal an element of the transition elements.
  • Semi-metals are boron, silicon, germanium, arsenic, antimony, tellurium, polonium, bismuth, selenium.
  • oxidized forms means that the elements can also be present in higher oxidation states than 0.
  • the metal from the platinum group Pd is selected from the platinum group Pd.
  • the further metal is Pt.
  • the semimetal is Bi.
  • Another embodiment contains as alkali metal K.
  • Pd, K and Bi are present.
  • Pd, K, Bi and Pt are present.
  • the said elements or their oxidized forms in the catalyst may also be present as a solid material, ie without a carrier material, they are used together with the magnesium-containing oxide.
  • the magnesium-containing oxide is used as a carrier oxide or is present in a carrier oxide.
  • the magnesium-containing oxide is preferably selected from the group of refractive oxides, for example consisting of SiO 2 , Al 2 O 3 , TiO 2 .
  • zeolites are well suited. Examples are zeolite Y, beta zeolite, ZSM-5, mordenite. Particularly noteworthy here are the ion-exchanged forms of zeolites, whereby magnesium-containing ion-exchanged forms are to be emphasized. It is also conceivable to use materials which have zeolite-like properties, for example mesoporous materials and phosphorus-containing aluminosilicates.
  • magnesium-containing oxides may be mentioned, in which the magnesium is present together with at least one elemental oxide selected from the group consisting of silicon, aluminum, titanium, zirconium, cerium and any desired mixture of these oxides.
  • magnesium-containing silicates particularly noteworthy here are magnesium-containing silicates, aluminosilicates and aluminates.
  • the hydrotalcite should also be mentioned as a carrier material.
  • the magnesium-containing oxide is a silicate, which is preferably present in crystalline form.
  • a magnesium-containing silicate or layered silicate in a carrier material or as a carrier material particularly good results are achieved.
  • refractive oxides such as zirconium oxide or carbon-containing, metallic or organic polymers
  • support materials such as PEEK, stainless steel, activated carbon.
  • the weight ratio of active components, ie the metal from the platinum group, the further metal or semimetal, the alkali or alkaline earth metal and / or their oxidized forms to the total weight of the catalyst is preferably in the range from 0.1: 25, preferably 0.5 : 10.
  • the molar ratio of Pd and Pt to Bi and K are each in the range of 10: 0.05, preferably 2.5: 0.5.
  • the highest yields for 1-ABD can be obtained in the composition range Pd 30-70 mol%, Pt 5-40 mol%, Bi 10-50 mol% and K 5-15 mol%.
  • Another object of the invention is also a process for the preparation of the catalyst, wherein the metal from the platinum group, the further metal or semimetal, the alkali or alkaline earth metal and / or their oxidized forms are deposited on the magnesium-containing oxide.
  • the deposition can be carried out by impregnation or precipitation in analogy to the known from the catalyst preparation process.
  • the magnesium-containing oxide can be impregnated with the components or these can be deposited or precipitated on the magnesium-containing oxide.
  • the components can be applied together or by stepwise individual addition. It is possible to separate them from solution or from the gas phase.
  • the particularly preferred compositions Pd, K and Bi or Pd, K 5 Bi and Pt are used either in metallic form, but preferably in oxidized form.
  • chlorides for example, the chlorides, acetates, nitrates, organic compounds such as carbonyl compounds, amine complexes or alcoholates, oxides and hydroxides, nitrides can be used. These are also called precursor connections.
  • At least one of the precursors used dissolves in one or more solvents.
  • solvents water, alcohols, ethers, esters and other solvents can be used, which meet the requirements of solubility. Particularly preferred is water as a solvent.
  • solvent regulators for regulating the pH or complexing agent or reducing or oxidizing agent. Such additives may be added at be used in subsequent preparation steps such as impregnations in different concentrations.
  • a physical-chemical treatment step usually follows. Such steps may include, for example, annealing and / or calcination. Also, a treatment with reactive gases is possible. Suitable gases are, for example, H 2 , H 2 / CO.
  • drying processes which can be carried out thermally or by freeze-drying, the hydrothermal treatment, irradiation with light.
  • Another object of the invention is also a process for the acetoxylation of C 2 -C 9 hydrocarbons using the catalyst. Preferably, this takes place in the gas phase in the presence of air and acetic acid.
  • Suitable C 2 -C 9 hydrocarbons are olefins or alkylated aromatics, in particular alkylaromatics.
  • olefins examples include ethylene, propylene, butenes, butadiene, isoprene, 1-hexene, 1-octene, 1-dodecene, styrene.
  • alkylated aromatics examples include toluene, xylenes.
  • the acetoxylation is carried out at a temperature of preferably 100 to 300 0 C, in particular 150 to 250 ° C.
  • the suitable temperature ranges are selected so that the reactants, namely acetic acid and C 2 -C 9 hydrocarbon are present in gaseous form.
  • the acetoxylation takes place in an oxygen-containing atmosphere. Air may be used, but it is also possible to mix oxygen with an inert gas, such as nitrogen, in a desired ratio.
  • the reaction is carried out continuously, for example in a fluidized bed.
  • the catalyst can be used particularly advantageously in the acetoxylation of butadiene, in particular in a process for the diacetoxylation.
  • a feed stream comprising butadiene, acetic acid and oxygen generates 1-ABD over the catalyst according to the invention in high yield.
  • the feed gas stream containing 1-ABD and acetic acid is passed over a second catalyst and converted there to high yield to 1, 4-DAB.
  • the second step is not known with the catalysts from the first stage, but with acidic or amphoteric solids, such as zeolites, silica-aluminas, TiO 2 , ZrO 2 , acidic ion exchangers, ZnO, WO 3 , WO 3 on TiO 2 and others refractive oxides, mixed oxides or polymeric materials.
  • acidic or amphoteric solids such as zeolites, silica-aluminas, TiO 2 , ZrO 2 , acidic ion exchangers, ZnO, WO 3 , WO 3 on TiO 2 and others refractive oxides, mixed oxides or polymeric materials.
  • a further subject of the invention is thus a process for the acetoxylation of butadiene comprising the step (i)
  • This process is also characterized by further comprising the step (ii):
  • step (ii) reacting the product obtained in step (i) in the gas phase with acetic acid using a catalyst.
  • the step (ii) is also characterized in that the catalyst is selected from the group of acidic or amphoteric solids, acidic ion exchangers, ZnO 3 WO 3 , WO 3 on TiO 2 , refractive oxides, mixed oxides.
  • Another object of the invention is the use of the catalyst in the above-disclosed acetoxylation of C 2 -C 9 hydrocarbons.
  • magnesium-containing oxides can favorably influence the acetoxylation of C 2 -C 9 -hydrocarbons in the gas phase.
  • Another object of the invention is thus the use of a magnesium-containing oxide for the acetoxylation of C 2 -C 9 hydrocarbons in the gas phase.
  • the magnesium-containing oxide is selected from the group consisting of silica, alumina, aluminosilicate, titanium dioxide, zeolite or mixtures of these oxides.
  • the zeolites described above can be used.
  • the magnesium-containing oxide is a silicate which is in crystalline form.
  • the magnesium-containing oxide is steatite.
  • the magnesium-containing oxide can be used in a carrier material and / or as a carrier material in a catalyst.
  • Such carriers may be prepared by treating preferably SiO 2 -containing materials with magnesium-containing precursors such as salts or gaseous magnesium compounds such as magnesium alkyls.
  • magnesium-treated materials can be post-treated physically-chemically, for example by heat treatment, calcination or hydrothermal treatment. The preparation and after-treatment is known or can be done by known methods.
  • pretreat such compounds for example steatite, mechanically, chemically or physically before applying the active components.
  • those treatment methods are preferred in which the surface of the support material is roughened and hydrophilized.
  • Such a treatment can be carried out, for example, by etching with acids or alkalis.
  • Active metals ie metals or their compounds, or oxidized forms thereof, which promote the rate of acetoxylation in the acetoxylation of C 2 -C 9 -hydrocarbons as defined above in the gas phase with acetic acid, can be applied to this support material.
  • the active metals used are preferably a metal from the platinum group, a further metal or semimetal, an alkali metal or alkaline earth metal and / or their oxidized forms, as defined above.
  • Pd, K and Bi or Pd, K, Bi and Pt and / or their oxidized forms are preferably present as active metals.
  • the active composition of the composition Pd 70 Bi 2O Ki 0 on the carrier material steatite (2.1% total loading based on the elements) was prepared by impregnation of an aqueous solution of the following precursors:
  • the impregnated material was 1 hour at room temperature in air and then C (2 hours) and 400 0 C (4 hours) under N 2 calcined for 12 hours at 80 ° C and then dried at 200 0th
  • Example 2 The catalysts of Examples 2 to 21 and Comparative Examples 1 to 3 were prepared analogously to Example 1, wherein the starting materials listed below were used for the preparation of the respective impregnating solutions: antimony acetate Sb (CH 3 COO) 3 , platinum nitrate Pt (NO 3 ) 2 , gold acid HAuCl 4 , silver nitrate AgNO 3 , copper nitrate Cu (NO 3 ) 2 x3H 2 O , tin oxalate Sn (C 2 O 4 ) 2 .
  • antimony acetate Sb (CH 3 COO) 3 platinum nitrate Pt (NO 3 ) 2
  • gold acid HAuCl 4 gold acid HAuCl 4
  • silver nitrate AgNO 3 silver nitrate AgNO 3
  • copper nitrate Cu (NO 3 ) 2 x3H 2 O tin oxalate Sn (C 2 O 4 ) 2 .
  • the steatite with the chemical composition Mg 3 [OH] 2 ZSi 4 O 10 ] used for the investigations was obtained from Ceramtec, the alumina Al 2 O 3 from Sasol and the silicon dioxide SiO 2 from Brace.
  • the BET surface areas of steatite, alumina and silica were 1 m 2 / g, 84 m 2 / g and 31 m 2 / g.
  • Table 7.a shows the results obtained in the acetoxylation of 1,3-butadiene
  • Table 7.b shows the results obtained for ethylene.
  • Table 1 Composition of the catalysts in the preparation of which the amount and type of active components was varied.
  • steatite was used as the carrier oxide.
  • the catalysts in Comparative Example 2 were prepared using an alumina-containing and Comparative Example 3 using a silicon-containing carrier oxide.
  • Table 2 Overview of the different educt gas mixtures which were tested on conversion of butadiene on the catalysts from Examples 1 to 20 and Comparative Examples 1 to 3, as well as the product gas compositions obtained thereby.
  • Table 7 a Overview of the different reactant gas mixtures, which was tested in the reaction of butadiene on the catalyst from Example 21, and the product gas compositions obtained thereby. The investigations were carried out at catalyst temperatures of 180 ° C and 210 ° C.
  • Table 7.b Overview of the different educt gas mixtures that were tested in the conversion of ethylene on the catalyst from Examples 21, and the product gas compositions obtained thereby. The tests were carried out at a catalyst temperature of 210 ° C.

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

L'invention concerne un catalyseur contenant un métal issu du groupe platine, un autre métal ou semi-métal, un métal alcalin ou alcalino-terreux et/ou leurs formes oxydées ainsi qu'un oxyde contenant du magnésium, en présence, de préférence, de Pd, K et Bi ou Pd, K, Bi et Pt. Ce catalyseur est destiné à l'acétoxylation d'un hydrocarbure C2-C9 tel que des oléfines ou des aromates alkyles, notamment de butadiène, dans la phase gazeuse dans une atmosphère oxygénée et en présence d'acide acétique.
PCT/EP2006/002041 2005-03-07 2006-03-06 Catalyseur d'acetoxylation d'hydrocarbures c2-c9 WO2006094746A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005010379.0 2005-03-07
DE200510010379 DE102005010379A1 (de) 2005-03-07 2005-03-07 Katalysator zur Acetoxylierung von C2-C9- Kohlenwasserstoffen

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Publication Number Publication Date
WO2006094746A1 true WO2006094746A1 (fr) 2006-09-14

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Cited By (6)

* Cited by examiner, † Cited by third party
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US8273682B2 (en) 2009-12-16 2012-09-25 Lyondell Chemical Technology, L.P. Preparation of palladium-gold catalyst
US8329611B2 (en) 2009-12-16 2012-12-11 Lyondell Chemical Technology, L,P. Titania-containing extrudate
US8507720B2 (en) 2010-01-29 2013-08-13 Lyondell Chemical Technology, L.P. Titania-alumina supported palladium catalyst
WO2014146481A1 (fr) * 2013-03-18 2014-09-25 The Hong Kong University Of Science And Technology Développement d'adsorbant à haute efficacité à partir de déchets électroniques et de matières à base d'aluminosilicate pour l'élimination d'ions métalliques lourds toxiques d'une eau résiduaire
EP3501650A1 (fr) * 2017-12-21 2019-06-26 Johnson Matthey Japan Godo Kaisha Catalyseur d'oxydation pour un échappement de moteur diesel
WO2019138256A1 (fr) * 2018-01-15 2019-07-18 Johnson Matthey Public Limited Company Catalyseur d'oxydation pour un échappement de moteur diesel

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US20110306748A1 (en) * 2010-06-11 2011-12-15 Daniel Travis Shay Titania-alumina-tungsta extrudate and its use

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US4571431A (en) * 1984-08-20 1986-02-18 Phillips Petroleum Company Process for the production of allyl acetate

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US3950400A (en) * 1970-11-20 1976-04-13 Hoechst Aktiengesellschaft Process for the oxacylation of olefins in the gaseous phase
US3755423A (en) * 1971-04-17 1973-08-28 Mitsubishiki Chem Ind Ltd Process for preparing an unsaturated glycol diester
US4571431A (en) * 1984-08-20 1986-02-18 Phillips Petroleum Company Process for the production of allyl acetate

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8273682B2 (en) 2009-12-16 2012-09-25 Lyondell Chemical Technology, L.P. Preparation of palladium-gold catalyst
US8329611B2 (en) 2009-12-16 2012-12-11 Lyondell Chemical Technology, L,P. Titania-containing extrudate
US8507720B2 (en) 2010-01-29 2013-08-13 Lyondell Chemical Technology, L.P. Titania-alumina supported palladium catalyst
WO2014146481A1 (fr) * 2013-03-18 2014-09-25 The Hong Kong University Of Science And Technology Développement d'adsorbant à haute efficacité à partir de déchets électroniques et de matières à base d'aluminosilicate pour l'élimination d'ions métalliques lourds toxiques d'une eau résiduaire
US10639623B2 (en) 2013-03-18 2020-05-05 The Hong Kong University Of Science And Technology Development of a high-efficiency adsorbent from E-waste and aluminosilicate-based materials for the removal of toxic heavy metal ions from wastewater
EP3501650A1 (fr) * 2017-12-21 2019-06-26 Johnson Matthey Japan Godo Kaisha Catalyseur d'oxydation pour un échappement de moteur diesel
WO2019122902A1 (fr) * 2017-12-21 2019-06-27 Johnson Matthey Japan Godo Kaisha Catalyseur d'oxydation destiné à un échappement de moteur diesel
CN111565842A (zh) * 2017-12-21 2020-08-21 庄信万丰日本合同会社 用于柴油机废气的氧化催化剂
GB2571422B (en) * 2017-12-21 2021-11-10 Johnson Matthey Japan Godo Kaisha Oxidation catalyst for a diesel engine exhaust
US11207641B2 (en) 2017-12-21 2021-12-28 Johnson Matthey Japan Godo Kaisha Oxidation catalyst for a diesel engine exhaust
WO2019138256A1 (fr) * 2018-01-15 2019-07-18 Johnson Matthey Public Limited Company Catalyseur d'oxydation pour un échappement de moteur diesel
EP3513875A1 (fr) * 2018-01-15 2019-07-24 Johnson Matthey Public Limited Company Catalyseur d'oxydation pour échappement de moteur diesel

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