CA3085928A1 - Heterogeneous catalyst for the production of methyl methacrylate by oxidative esterification - Google Patents

Heterogeneous catalyst for the production of methyl methacrylate by oxidative esterification Download PDF

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Publication number
CA3085928A1
CA3085928A1 CA3085928A CA3085928A CA3085928A1 CA 3085928 A1 CA3085928 A1 CA 3085928A1 CA 3085928 A CA3085928 A CA 3085928A CA 3085928 A CA3085928 A CA 3085928A CA 3085928 A1 CA3085928 A1 CA 3085928A1
Authority
CA
Canada
Prior art keywords
catalyst
mol
noble metal
titanium
support
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.)
Pending
Application number
CA3085928A
Other languages
English (en)
French (fr)
Inventor
Christopher D. FRICK
Jeffrey Herron
Kirk W. Limbach
Wen Sheng LEE
Victor J. SUSSMAN
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.)
Dow Global Technologies LLC
Rohm and Haas Co
Original Assignee
Dow Global Technologies LLC
Rohm and Haas Co
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 Dow Global Technologies LLC, Rohm and Haas Co filed Critical Dow Global Technologies LLC
Publication of CA3085928A1 publication Critical patent/CA3085928A1/en
Pending 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
    • 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
    • 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
    • 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
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • 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
    • B01J23/44—Palladium
    • 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
    • B01J23/48—Silver or gold
    • B01J23/52—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
    • B01J23/54—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
    • 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
    • B01J35/396—Distribution of the active metal ingredient
    • B01J35/397—Egg shell like
    • 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
    • B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
    • 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
    • B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
    • B01J35/51—Spheres
    • B01J35/53—Spheres with a core-shell structure
    • 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
    • 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
    • B01J37/03—Precipitation; Co-precipitation
    • B01J37/031—Precipitation
    • B01J37/035—Precipitation on carriers
    • 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
    • B01J37/08—Heat treatment
    • B01J37/082—Decomposition and pyrolysis
    • B01J37/088—Decomposition of a metal salt
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • 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
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA3085928A 2018-01-10 2018-12-13 Heterogeneous catalyst for the production of methyl methacrylate by oxidative esterification Pending CA3085928A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201862615502P 2018-01-10 2018-01-10
US62/615,502 2018-01-10
PCT/US2018/065372 WO2019139719A1 (en) 2018-01-10 2018-12-13 Heterogeneous catalyst for the production of methyl methacrylate by oxidative esterification

Publications (1)

Publication Number Publication Date
CA3085928A1 true CA3085928A1 (en) 2019-07-18

Family

ID=65041907

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3085928A Pending CA3085928A1 (en) 2018-01-10 2018-12-13 Heterogeneous catalyst for the production of methyl methacrylate by oxidative esterification

Country Status (11)

Country Link
US (1) US11577225B2 (https=)
EP (1) EP3737496A1 (https=)
JP (2) JP2021510344A (https=)
KR (1) KR102739478B1 (https=)
CN (1) CN111511468B (https=)
BR (1) BR112020011829B1 (https=)
CA (1) CA3085928A1 (https=)
MX (1) MX2020006629A (https=)
SA (1) SA520412331B1 (https=)
SG (1) SG11202005796UA (https=)
WO (1) WO2019139719A1 (https=)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112165987B (zh) * 2018-06-28 2024-05-17 陶氏环球技术有限责任公司 非均相催化剂
JP2021528231A (ja) * 2018-06-28 2021-10-21 ダウ グローバル テクノロジーズ エルエルシー 不均一触媒
JP2023519126A (ja) * 2020-03-17 2023-05-10 ダウ グローバル テクノロジーズ エルエルシー 長寿命触媒による酸化的エステル化の方法及び触媒

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW377306B (en) * 1996-12-16 1999-12-21 Asahi Chemical Ind Noble metal support
JP3238894B2 (ja) * 1998-02-09 2001-12-17 三菱レイヨン株式会社 メタクリル酸メチルの製造方法
JP2002361086A (ja) * 2001-06-04 2002-12-17 Nippon Shokubai Co Ltd カルボン酸エステル合成用触媒及びカルボン酸エステルの製造方法
US7326806B2 (en) * 2001-06-04 2008-02-05 Nippon Shokubai Co., Ltd. Catalyst for the preparation of carboxylic esters and method for producing carboxylic esters
JP4069242B2 (ja) * 2001-06-04 2008-04-02 株式会社日本触媒 金属粒子担持体及びカルボン酸エステルの製造方法
JP2004181357A (ja) * 2002-12-03 2004-07-02 Nippon Shokubai Co Ltd 金微粒子の剥離抑制方法
JP2004181359A (ja) * 2002-12-03 2004-07-02 Nippon Shokubai Co Ltd カルボン酸エステル製造用触媒及びカルボン酸エステル製造方法
US20040192983A1 (en) * 2003-02-18 2004-09-30 Chevron Phillips Chemical Co. Acetylene hydrogenation catalyst with segregated palladium skin
JP2005013800A (ja) * 2003-06-24 2005-01-20 Mitsubishi Chemicals Corp 固体触媒及びこれを用いた酸化的付加生成物の製造方法
US7955570B2 (en) * 2006-02-28 2011-06-07 3M Innovative Properties Company Low pressure drop, highly active catalyst systems using catalytically active gold
DE102007025444A1 (de) * 2007-05-31 2008-12-11 Süd-Chemie AG VAM-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung
JP4674921B2 (ja) * 2007-08-13 2011-04-20 旭化成ケミカルズ株式会社 カルボン酸エステル製造用触媒、その製造方法、並びにカルボン酸エステルの製造方法
US7531675B1 (en) * 2007-10-24 2009-05-12 Lyondell Chemical Technology, L.P. Direct epoxidation process using improved catalyst composition
EP2210664A4 (en) * 2007-10-26 2011-12-21 Asahi Kasei Chemicals Corp COMPOSITE-LOADED ARTICLE, METHOD FOR PRODUCING THE COMPOSITE-RELATED ARTICLE, AND METHOD FOR PRODUCING THE COMPOUND FROM THE COMPOSITE-RELATED ARTICLE AS A CHEMICAL SYNTHETIC CATALYST
CN201294443Y (zh) 2008-12-01 2009-08-19 东元总合科技（杭州）有限公司 永磁自启动同步电机转子
JP5588657B2 (ja) * 2009-11-10 2014-09-10 旭化成ケミカルズ株式会社 カルボン酸の製造方法
DE102012003236A1 (de) * 2012-02-20 2013-08-22 Clariant Produkte (Deutschland) Gmbh Vorvergoldung von Pd-Au-gecoateten Schalenkatalysatoren
EP2986589B1 (de) * 2013-04-19 2018-03-14 Evonik Röhm GmbH Verfahren zur herstellung von methylmethacrylat
TW201512168A (zh) * 2013-07-29 2015-04-01 Rohm & Haas 氧化酯化方法
EP2886528A1 (de) * 2013-12-20 2015-06-24 Evonik Industries AG Verfahren zur Herstellung von ungesättigten Estern ausgehend von Aldehyden durch Direkte Oxidative Veresterung
EP2886529A1 (en) * 2013-12-20 2015-06-24 Evonik Industries AG Process for producing methyl methacrylate
US10232353B2 (en) 2015-01-16 2019-03-19 Evonik Röhm Gmbh Gold-based catalyst for the oxidative esterification of aldehydes to obtain carboxylic esters
EP3170558A1 (de) * 2015-11-19 2017-05-24 Evonik Röhm GmbH Gold-basierten katalysator für die oxidative veresterung von aldehyden zu carbonsäureestern
CN107519892B (zh) * 2016-06-20 2019-11-22 中国科学院大连化学物理研究所 一种负载型氧化酯化催化剂及其制备方法和应用
KR102666711B1 (ko) * 2018-01-10 2024-05-17 다우 글로벌 테크놀로지스 엘엘씨 불균일 촉매를 사용하여 산화적 에스터화에 의해 메틸 메타크릴레이트를 제조하는 방법
CN112165987B (zh) * 2018-06-28 2024-05-17 陶氏环球技术有限责任公司 非均相催化剂

Also Published As

Publication number Publication date
EP3737496A1 (en) 2020-11-18
JP7804625B2 (ja) 2026-01-22
US11577225B2 (en) 2023-02-14
US20200330959A1 (en) 2020-10-22
JP2023175730A (ja) 2023-12-12
SG11202005796UA (en) 2020-07-29
BR112020011829A2 (pt) 2020-11-24
CN111511468A (zh) 2020-08-07
KR20200105854A (ko) 2020-09-09
SA520412331B1 (ar) 2024-02-19
JP2021510344A (ja) 2021-04-22
KR102739478B1 (ko) 2024-12-09
WO2019139719A1 (en) 2019-07-18
CN111511468B (zh) 2023-07-11
MX2020006629A (es) 2020-09-22
BR112020011829B1 (pt) 2023-05-09

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