CA2968906C - Process for preparing esters of lactic acid, and 2-hydroxy-3-butenoic acid or alfa-hydroxy methionine analogues from sugars - Google Patents

Process for preparing esters of lactic acid, and 2-hydroxy-3-butenoic acid or alfa-hydroxy methionine analogues from sugars Download PDF

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Publication number
CA2968906C
CA2968906C CA2968906A CA2968906A CA2968906C CA 2968906 C CA2968906 C CA 2968906C CA 2968906 A CA2968906 A CA 2968906A CA 2968906 A CA2968906 A CA 2968906A CA 2968906 C CA2968906 C CA 2968906C
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Canada
Prior art keywords
process according
lewis acid
hydroxy
acid catalyst
solid lewis
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CA2968906A
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English (en)
French (fr)
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CA2968906A1 (en
Inventor
Irantzu SADABA ZUBIRI
Esben Taarning
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Topsoe AS
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Haldor Topsoe AS
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/18—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of thiols to unsaturated 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of germanium, 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/26—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/44—Preparation of carboxylic acid esters by oxidation-reduction of aldehydes, e.g. Tishchenko reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/62—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
    • C07C69/68—Lactic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00027—Process aspects
    • B01J2219/00033—Continuous processes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
CA2968906A 2014-11-28 2015-11-12 Process for preparing esters of lactic acid, and 2-hydroxy-3-butenoic acid or alfa-hydroxy methionine analogues from sugars Active CA2968906C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP14195485.9 2014-11-28
EP14195485 2014-11-28
DKPA201500288 2015-05-13
DKPA201500288 2015-05-13
PCT/EP2015/076399 WO2016083137A1 (en) 2014-11-28 2015-11-12 Process for preparing esters of lactic acid, and 2-hydroxy-3-butenoic acid or alfa-hydroxy methionine analogues from sugars

Publications (2)

Publication Number Publication Date
CA2968906A1 CA2968906A1 (en) 2016-06-02
CA2968906C true CA2968906C (en) 2023-09-12

Family

ID=59019550

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2968906A Active CA2968906C (en) 2014-11-28 2015-11-12 Process for preparing esters of lactic acid, and 2-hydroxy-3-butenoic acid or alfa-hydroxy methionine analogues from sugars

Country Status (19)

Country Link
US (3) US10100007B2 (https=)
EP (2) EP3461806B1 (https=)
JP (2) JP6788588B2 (https=)
KR (1) KR102475064B1 (https=)
CN (2) CN107001253B (https=)
AU (1) AU2015352840B2 (https=)
BR (1) BR112017011304B1 (https=)
CA (1) CA2968906C (https=)
CU (1) CU24499B1 (https=)
DK (2) DK3461806T3 (https=)
ES (2) ES2813341T3 (https=)
HU (2) HUE046852T2 (https=)
MX (2) MX2017006538A (https=)
MY (1) MY194486A (https=)
PL (2) PL3224234T3 (https=)
RU (2) RU2710014C2 (https=)
SG (2) SG10201810447YA (https=)
WO (1) WO2016083137A1 (https=)
ZA (1) ZA201703204B (https=)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3461806B1 (en) 2014-11-28 2020-08-05 Haldor Topsøe A/S Process for preparing alfa-hydroxy methionine analogues from sugars
EP3288920B1 (en) * 2015-04-30 2019-09-25 Haldor Topsøe A/S A process for the preparation of methionine alpha-hydroxy analogues from sugars and derivatives thereof
WO2017191282A1 (en) 2016-05-04 2017-11-09 Haldor Topsøe A/S New adipate-type compounds and a process of preparing it
CN106349060B (zh) * 2016-08-26 2020-06-12 上海交通大学 一种路易斯酸催化转化碳水化合物制备乳酸烷基酯的方法
CN109289909B (zh) * 2018-10-16 2021-03-19 郑州大学 一种催化复杂糖转化制备乳酸酯的催化剂
CN121318803A (zh) * 2019-09-06 2026-01-13 建明实业股份有限公司 通过酯化α-羟基酸制备α-羟基酯的工艺
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
CN113831238B (zh) * 2020-06-24 2024-05-03 中国石油化工股份有限公司 一种催化转化碳水化合物制备乳酸甲酯的方法
CN116272945B (zh) * 2023-01-16 2024-12-31 山东理工大学 酸碱碳基催化剂的制备方法及应用

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4792620A (en) * 1983-10-14 1988-12-20 Bp Chemicals Limited Carbonylation catalysts
US4933161A (en) 1987-02-04 1990-06-12 Exxon Research And Engineering Company Tin substitution into zeolite frameworks
US5973200A (en) 1997-01-23 1999-10-26 Novus International, Inc. Process for the preparation of 2-hydroxy-4-(methylthio) butanoic acid or methionine by mercaptan addition
DE10140202A1 (de) 2001-08-16 2003-03-06 Bayer Ag Vanadium-Imido-Phosphoraniminato für die Olefinpolymerisation
DE102005003990A1 (de) * 2005-01-28 2006-08-03 Degussa Ag Herstellung von 3-(Alkylthio)propanal
EP2184270B1 (en) * 2008-11-11 2013-02-13 Haldor Topsoe A/S Zeolite-catalyzed preparation of alpha-hydroxy carboxylic acid compounds and esters thereof
FR2938535B1 (fr) 2008-11-20 2012-08-17 Arkema France Procede de fabrication de methylmercaptopropionaldehyde et de methionine a partir de matieres renouvelables
HUE036023T2 (hu) * 2009-04-03 2018-06-28 Mitsubishi Gas Chemical Co Eljárás alfa-hidroxikarbonsav-észter elõállítására
TWI630197B (zh) 2013-02-27 2018-07-21 丹麥商哈爾德杜薩公司 從包含低分子量羰基化合物之組成物移除甲醛的方法
NO3036040T3 (https=) 2013-08-20 2018-04-07
EP3461806B1 (en) 2014-11-28 2020-08-05 Haldor Topsøe A/S Process for preparing alfa-hydroxy methionine analogues from sugars

Also Published As

Publication number Publication date
RU2019131408A (ru) 2019-10-29
EP3461806B1 (en) 2020-08-05
PL3224234T3 (pl) 2020-03-31
CN109942466A (zh) 2019-06-28
PL3461806T3 (pl) 2021-02-08
HUE046852T2 (hu) 2020-03-30
JP2020125313A (ja) 2020-08-20
MX2020011677A (es) 2020-12-10
SG11201704329UA (en) 2017-06-29
CN107001253A (zh) 2017-08-01
EP3224234B1 (en) 2019-08-14
US20190016674A1 (en) 2019-01-17
CN109942466B (zh) 2021-08-27
JP2017537096A (ja) 2017-12-14
SG10201810447YA (en) 2018-12-28
JP6788588B2 (ja) 2020-11-25
CA2968906A1 (en) 2016-06-02
RU2710014C2 (ru) 2019-12-24
KR102475064B1 (ko) 2022-12-07
US10343986B2 (en) 2019-07-09
RU2017122603A (ru) 2018-12-29
CU20170072A7 (es) 2017-10-05
WO2016083137A1 (en) 2016-06-02
WO2016083137A9 (en) 2016-08-25
KR20170091107A (ko) 2017-08-08
CU24499B1 (es) 2021-02-04
US10100007B2 (en) 2018-10-16
EP3224234A1 (en) 2017-10-04
US10280136B2 (en) 2019-05-07
AU2015352840B2 (en) 2020-01-02
BR112017011304B1 (pt) 2020-04-14
MX2017006538A (es) 2017-08-09
BR112017011304A2 (pt) 2018-07-10
NZ732280A (en) 2021-09-24
DK3224234T3 (da) 2019-10-28
ES2813341T3 (es) 2021-03-23
ZA201703204B (en) 2019-10-30
ES2748690T3 (es) 2020-03-17
DK3461806T3 (da) 2020-09-28
US20190062271A1 (en) 2019-02-28
AU2015352840A1 (en) 2017-06-15
HUE051552T2 (hu) 2021-03-29
US20170334844A1 (en) 2017-11-23
RU2017122603A3 (https=) 2019-05-31
MY194486A (en) 2022-11-30
EP3461806A1 (en) 2019-04-03
CN107001253B (zh) 2019-03-12
JP6826225B2 (ja) 2021-02-03

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