CA2549456A1 - Process of preparing glycolaldehyde - Google Patents

Process of preparing glycolaldehyde Download PDF

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Publication number
CA2549456A1
CA2549456A1 CA002549456A CA2549456A CA2549456A1 CA 2549456 A1 CA2549456 A1 CA 2549456A1 CA 002549456 A CA002549456 A CA 002549456A CA 2549456 A CA2549456 A CA 2549456A CA 2549456 A1 CA2549456 A1 CA 2549456A1
Authority
CA
Canada
Prior art keywords
formaldehyde
group
glycolaldehyde
carbon atoms
phospha
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
CA002549456A
Other languages
English (en)
French (fr)
Inventor
Karina Quetzaly Almeida Lenero
Eit Drent
Roelof Van Ginkel
Robert Ian Pugh
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2549456A1 publication Critical patent/CA2549456A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
    • B01J31/248—Bridged ring systems, e.g. 9-phosphabicyclononane
    • B01J31/2485—Tricyclic systems, e.g. phosphaadamantanes and hetero analogues
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/648—Fischer-Tropsch-type reactions
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/20—Carbonyls
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Health & Medical Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
CA002549456A 2003-12-16 2004-12-15 Process of preparing glycolaldehyde Abandoned CA2549456A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP03257883 2003-12-16
EP03257883.3 2003-12-16
PCT/EP2004/053492 WO2005058788A1 (en) 2003-12-16 2004-12-15 Process of preparing glycolaldehyde

Publications (1)

Publication Number Publication Date
CA2549456A1 true CA2549456A1 (en) 2005-06-30

Family

ID=34684623

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002549456A Abandoned CA2549456A1 (en) 2003-12-16 2004-12-15 Process of preparing glycolaldehyde

Country Status (11)

Country Link
US (2) US7449607B2 (enExample)
EP (1) EP1697291A1 (enExample)
JP (1) JP4474419B2 (enExample)
KR (1) KR20060117345A (enExample)
CN (1) CN100434412C (enExample)
AU (1) AU2004298446B2 (enExample)
BR (1) BRPI0417643A (enExample)
CA (1) CA2549456A1 (enExample)
MX (1) MXPA06006705A (enExample)
RU (1) RU2371429C2 (enExample)
WO (1) WO2005058788A1 (enExample)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7858787B2 (en) 2006-09-22 2010-12-28 Shell Oil Company Process for producing olefins
US7420093B2 (en) 2006-09-29 2008-09-02 Eastman Chemical Company Process for the preparation of glycolaldehyde
US7301054B1 (en) 2006-09-29 2007-11-27 Eastman Chemical Company Process for the preparation of glycolaldehyde
US7674937B2 (en) 2008-05-28 2010-03-09 Eastman Chemical Company Hydroformylation catalysts
FR2943061B1 (fr) * 2009-03-13 2011-02-25 Rhodia Operations Composes organophosphores, systemes catalytiques comprenant ces composes et procede d'hydrocyanation ou d'hydroformylation utilisant ces systemes catalytiques
JP5791628B2 (ja) 2009-12-17 2015-10-07 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 高級エタノールアミンの製造方法
RU2573570C2 (ru) 2009-12-17 2016-01-20 Басф Се Превращение гликолевого альдегида со средством аминирования
CN101811933B (zh) * 2010-04-26 2013-05-08 常州大学 一种催化合成乙二醇的方法
TWI508937B (zh) * 2014-04-30 2015-11-21 Chien An Chen 使用甲醇為原料經由甲醛、乙醇醛的中間產物而合成乙二醇的製造方法
CN105085211B (zh) * 2014-05-16 2017-09-05 陈建安 一种甲醛、乙醇醛及乙二醇的制造方法
DK3145902T3 (en) * 2014-05-19 2018-10-01 Iowa Corn Promotion Board PROCEDURE FOR CONTINUOUS PREPARATION OF ETHYLENGYLYCOL FROM CARBOHYDRATES
MX392317B (es) * 2014-06-30 2025-03-21 Haldor Topsoe As Proceso para la preparación de etilenglicol a partir de azúcares.
AU2017205691B2 (en) 2016-01-07 2021-06-17 Haldor Topsøe A/S Process for the preparation of ethylene glycol from sugars
BR112018013543B1 (pt) 2016-01-07 2022-02-08 Haldor Topsøe A/S Processos para a preparação do composto hidroxi c1-c3 e sistema para executar continuamente os referidos processos
CN105618035B (zh) * 2016-02-02 2018-05-11 中国科学院福建物质结构研究所 合成气制备乙醇醛所用的负载型铑催化剂及其制备方法
BR112019010790A2 (pt) 2016-12-08 2019-10-01 Haldor Topsøe A/S produção de glicolaldeído por fragmentação termolítica
GB201904612D0 (en) 2019-04-02 2019-05-15 Univ Leuven Kath Reaction of glycoladehyde
WO2020095147A1 (en) * 2018-11-07 2020-05-14 Sabic Global Technologies B.V. Catalyst systems and methods for their use in selective hydroformylation of formaldehyde to glycolaldehyde
WO2020249428A1 (en) 2019-06-11 2020-12-17 Basf Se Products obtained by the conversion of glycolaldehyde derivatives and aminating agents and their conversion to ethyleneamines and ethanolamines
WO2020249426A1 (en) 2019-06-11 2020-12-17 Basf Se Conversion of glycolaldehyde with an aminating agent
BR112021022992A2 (pt) 2019-06-11 2022-01-04 Basf Se Processos para a fabricação de etilenoaminas e etanolaminas e derivado de triazinano
CN112337508A (zh) * 2020-11-03 2021-02-09 中国科学院福建物质结构研究所 一种乙醇醛合成用铑基催化剂及其制备方法
DE202021103519U1 (de) 2021-07-01 2021-07-16 Schill + Seilacher Gmbh Gerbmittel, Verwendung des Gerbmittels zum Gerben von Tierhäuten und Fellen und daraus erhaltenes Leder
ES2975566T3 (es) 2021-07-01 2024-07-09 Schill Seilacher Gmbh Agente curtiente, uso de un curtiente y procedimiento de curtido de pieles de animales y del cuero obtenido a partir de las mismas
CN114751813B (zh) * 2022-05-05 2023-12-15 天津大学 一种甲醛氢甲酰化制备乙醇醛的方法
CN115108887A (zh) * 2022-08-18 2022-09-27 山东能源集团有限公司 一种乙二醇的制备方法
CN115340440B (zh) * 2022-08-18 2024-09-06 山东能源集团有限公司 一种制备乙二醇的方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3050531A (en) 1960-07-06 1962-08-21 American Cyanamid Co Substituted 10-phosphatricyclo [3.3.1.1] decanes and methods of preparing same
US4414421A (en) * 1981-08-03 1983-11-08 Shell Oil Company Process for the preparation of glycol aldehyde
US4608444A (en) * 1984-04-05 1986-08-26 The Halcon Sd Group, Inc. Process and accompanying catalysts for the hydroformylation of formaldehyde to glycol-aldehyde
US4847423A (en) * 1988-03-03 1989-07-11 Hoechst Celanese Corporation Hydroformylation of aqueous formaldehyde using a rhodium-tricyclohexylphosphine catalyst system
SU1608182A1 (ru) * 1988-09-15 1990-11-23 Предприятие П/Я В-2287 Способ получени гликолевого альдегида
US5567856A (en) * 1995-05-30 1996-10-22 Hoechst Celanese Corporation Synthesis of and hydroformylation with fluoro-substituted bidentate phosphine ligands
US6156934A (en) * 1997-03-26 2000-12-05 Shell Oil Company Diphosphines
DE10023468A1 (de) 2000-05-12 2001-11-15 Basf Ag Verfahren zur Hydroformylierung ethylenisch ungesättigter Verbindungen und Ligand-Metall-Komplex als Katalysator hierfür

Also Published As

Publication number Publication date
US7511178B2 (en) 2009-03-31
EP1697291A1 (en) 2006-09-06
US20090012333A1 (en) 2009-01-08
BRPI0417643A (pt) 2007-03-27
AU2004298446B2 (en) 2008-07-31
JP4474419B2 (ja) 2010-06-02
RU2006125408A (ru) 2008-01-27
RU2371429C2 (ru) 2009-10-27
US7449607B2 (en) 2008-11-11
US20070249871A1 (en) 2007-10-25
CN100434412C (zh) 2008-11-19
JP2007516976A (ja) 2007-06-28
AU2004298446A1 (en) 2005-06-30
CN1894188A (zh) 2007-01-10
WO2005058788A1 (en) 2005-06-30
KR20060117345A (ko) 2006-11-16
MXPA06006705A (es) 2006-08-23

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Legal Events

Date Code Title Description
EEER Examination request
FZDE Discontinued

Effective date: 20130917