CA2866003A1 - Preparation of alpha, beta-unsaturated carboxylic acids and esters thereof - Google Patents

Preparation of alpha, beta-unsaturated carboxylic acids and esters thereof Download PDF

Info

Publication number
CA2866003A1
CA2866003A1 CA2866003A CA2866003A CA2866003A1 CA 2866003 A1 CA2866003 A1 CA 2866003A1 CA 2866003 A CA2866003 A CA 2866003A CA 2866003 A CA2866003 A CA 2866003A CA 2866003 A1 CA2866003 A1 CA 2866003A1
Authority
CA
Canada
Prior art keywords
catalyst
acid
dehydroxylation
type zeolite
reaction
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.)
Abandoned
Application number
CA2866003A
Other languages
English (en)
French (fr)
Inventor
A. Cenan Ozmeral
Joseph P. GLAS
Rajesh Dasari
Setrak Tanielyan
Ramesh Deoram BHAGAT
Mohan Reddy Kasireddy
Ramnik Singh
Vijay GNANADESIKAN
Robert L. Augustine
Santosh MORE
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.)
Myriant Corp
Original Assignee
Myriant Corp
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 Myriant Corp filed Critical Myriant Corp
Publication of CA2866003A1 publication Critical patent/CA2866003A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
    • 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
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds 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
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/60—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the type L, as exemplified by patent document US3216789
    • 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
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/60—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the type L, as exemplified by patent document US3216789
    • B01J29/605—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the type L, as exemplified by patent document US3216789 containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/60—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the type L, as exemplified by patent document US3216789
    • B01J29/64—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the type L, as exemplified by patent document US3216789 containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • 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
    • B01J35/45—Nanoparticles
    • 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
    • B01J37/06—Washing
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • 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
    • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
    • B01J2229/10—After treatment, characterised by the effect to be obtained
    • B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
    • B01J2229/186—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself not in framework positions
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2866003A 2012-03-07 2013-03-06 Preparation of alpha, beta-unsaturated carboxylic acids and esters thereof Abandoned CA2866003A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201261608053P 2012-03-07 2012-03-07
US61/608,053 2012-03-07
US201313819035A 2013-02-26 2013-02-26
US13/819,035 2013-02-26
PCT/US2013/029368 WO2013134385A1 (en) 2012-03-07 2013-03-06 Preparation of alpha, beta-unsaturated carboxylic acids and esters thereof

Publications (1)

Publication Number Publication Date
CA2866003A1 true CA2866003A1 (en) 2013-09-12

Family

ID=49117293

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2866003A Abandoned CA2866003A1 (en) 2012-03-07 2013-03-06 Preparation of alpha, beta-unsaturated carboxylic acids and esters thereof

Country Status (7)

Country Link
EP (1) EP2822923A4 (cs)
JP (1) JP2015510885A (cs)
KR (1) KR20140131589A (cs)
CN (1) CN104159883A (cs)
CA (1) CA2866003A1 (cs)
IN (1) IN2014DN07484A (cs)
WO (1) WO2013134385A1 (cs)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9452967B2 (en) * 2012-04-11 2016-09-27 The Procter & Gamble Company Process for production of acrylic acid or its derivatives
CN105705647B (zh) 2013-09-03 2020-03-27 Ptt全球化学公众有限公司 从1，3-丙二醇制造丙烯酸、丙烯腈和1，4-丁二醇的方法
US9938224B2 (en) 2013-10-17 2018-04-10 Cargill, Incorporated Methods for producing alkyl hydroxyalkanoates
WO2015179302A1 (en) * 2014-05-19 2015-11-26 Iowa Corn Promotion Board Process for the continuous production of ethylene glycol from carbohydrates
WO2016061356A1 (en) * 2014-10-17 2016-04-21 Cargill, Incorporated Methods for producing an ester of an alpha, beta-unsaturated carboxylic acid
AU2015355368B2 (en) * 2014-12-02 2019-04-18 Archer Daniels Midland Company Process for making acrylic acid from dextrose
CN107848939B (zh) * 2015-06-10 2021-06-01 Ptt全球化学公众有限公司 以乙醛作为主要副产物的生产丙烯酸的方法
JP6694641B2 (ja) * 2015-06-30 2020-05-20 国立研究開発法人産業技術総合研究所 アクリル酸等のα、β−不飽和カルボン酸、その誘導体の製造法
CN106582784B (zh) * 2015-10-14 2019-11-08 中国石油化工股份有限公司 丙烯酸酯催化剂
WO2017108890A1 (en) * 2015-12-21 2017-06-29 Purac Biochem Bv Process for manufacturing acrylic acid
CN106905155B (zh) * 2017-03-29 2020-04-10 万华化学集团股份有限公司 一种裂解丙烯酸丁酯重组分生成丙烯酸丁酯的方法
US10308568B2 (en) 2017-05-01 2019-06-04 Chevron Phillips Chemical Company Lp Selective poisoning of aromatization catalysts to increase catalyst activity and selectivity
US11273434B2 (en) * 2017-10-06 2022-03-15 The Procter & Gamble Company Regeneration method of solid catalyst
CN111344276B (zh) * 2017-11-17 2023-02-28 普拉克生化公司 用于从乳酸甲酯生产丙烯酸甲酯的方法
CN111253251B (zh) * 2018-11-30 2023-04-11 中国石油化工股份有限公司 一种制备乳酸酯的方法
CN111253239B (zh) * 2018-11-30 2023-04-07 中国石油化工股份有限公司 一种催化丙酮醛制备乳酸的方法
CN111253252B (zh) * 2018-11-30 2023-04-11 中国石油化工股份有限公司 一种催化糖制备乳酸酯的方法
CN111253248B (zh) * 2018-11-30 2023-04-11 中国石油化工股份有限公司 一种催化丙酮醛制备乳酸酯的方法
CN111250157B (zh) * 2018-11-30 2023-04-07 中国石油化工股份有限公司 一种催化糖制备乳酸的方法
CN111253259B (zh) * 2018-11-30 2023-04-07 中国石油化工股份有限公司 一种催化二羟基丙酮和/或甘油醛制备乳酸酯的方法
CN111253226B (zh) * 2018-11-30 2023-03-10 中国石油化工股份有限公司 一种催化二羟基丙酮和/或甘油醛制备乳酸的方法
CN111253238B (zh) * 2018-11-30 2023-03-10 中国石油化工股份有限公司 一种制备乳酸的方法
CN111253237B (zh) * 2018-11-30 2023-04-07 中国石油化工股份有限公司 一种催化糖制备丙酮醛的方法
CN110201716B (zh) * 2019-05-21 2022-04-19 南京工业大学 一种醇胺基团改性的有序介孔C/SiO2负载杂多酸催化剂及其制备方法和应用
CN111905802B (zh) * 2020-06-15 2022-01-18 厦门大学 一种使用钼-碱金属/碱土金属修饰的路易斯酸催化剂制乳酸酯的方法
CN115608406B (zh) * 2021-07-13 2023-12-08 中国石油化工股份有限公司 用于合成甲基丙烯酸甲酯的催化剂及其制备方法和应用
CN119793523A (zh) * 2023-10-10 2025-04-11 中国石油化工股份有限公司 酯化催化剂及其制备方法以及在甲基丙烯酸甲酯合成反应中的应用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4617405A (en) * 1984-09-25 1986-10-14 A. E. Staley Manufacturing Company Preparation of alpha, beta-unsaturated carbonyl compounds
US4729978A (en) * 1987-05-04 1988-03-08 Texaco Inc. Catalyst for dehydration of lactic acid to acrylic acid
FR2882053B1 (fr) * 2005-02-15 2007-03-23 Arkema Sa Procede de deshydratation du glycerol en acrolene
FR2884818B1 (fr) * 2005-04-25 2007-07-13 Arkema Sa Procede de preparation d'acide acrylique a partir de glycerol
FR2884817B1 (fr) * 2005-04-25 2007-06-22 Arkema Sa Procede de preparation d'acide acrylique a partir de glycerol
CN101352688A (zh) * 2007-07-23 2009-01-28 湖南大学 乳酸脱水制丙烯酸催化剂及反应工艺
CN102655931A (zh) * 2009-09-18 2012-09-05 日本化药株式会社 用于通过甘油脱水反应制备丙烯醛和/或丙烯酸的催化剂和方法
BR112013004935A2 (pt) * 2010-09-07 2016-08-02 Myriant Corp "desitratação catalítica de ácido láctico e ésteres de ácido láctico".

Also Published As

Publication number Publication date
WO2013134385A1 (en) 2013-09-12
CN104159883A (zh) 2014-11-19
IN2014DN07484A (cs) 2015-04-24
EP2822923A1 (en) 2015-01-14
KR20140131589A (ko) 2014-11-13
JP2015510885A (ja) 2015-04-13
EP2822923A4 (en) 2015-11-04

Similar Documents

Publication Publication Date Title
CA2866003A1 (en) Preparation of alpha, beta-unsaturated carboxylic acids and esters thereof
KR102620747B1 (ko) 주요 부산물인 아세트알데히드로 아크릴산의 신규한 제조 방법
WO2012033845A2 (en) Catalytic dehydration of lactic acid and lactic acid esters
RU2475469C1 (ru) Способ получения олефинов
KR101430798B1 (ko) 산 촉매의 존재 하에서의 알코올의 사용전 정제
CA2964762A1 (en) Methods for conversion of ethanol to functionalized lower hydrocarbons and downstream hydrocarbons
JP7033127B2 (ja) ジエンの製造方法
US9914699B2 (en) Process of dehydration reactions
US20150038735A1 (en) Preparation of alpha, beta-unsaturated carboxylic acids and esters thereof
Hu et al. Selective dehydration of bio‐ethanol to ethylene catalyzed by lanthanum‐phosphorous‐modified HZSM‐5: Influence of the fusel
EP3710421B1 (en) Process for the production of methyl acrylate from methyl lactate
KR20160055167A (ko) 아크릴산으로부터 프로피온산의 분리
Glas et al. Ozmeral et al.(43) Pub. Date: Feb. 5, 2015
CN101559383A (zh) 一种乙醇脱水反应中zsm-5催化剂的再生方法
Onda Production of lactic acid from sugars by homogeneous and heterogeneous catalysts
Faisal Zeolite adsorbents and catalysts for the recovery and production of biochemicals

Legal Events

Date Code Title Description
FZDE Discontinued

Effective date: 20180306