RU2002128740A - Одностадийный способ получения 1,3-диола - Google Patents

Одностадийный способ получения 1,3-диола

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Publication number
RU2002128740A
RU2002128740A RU2002128740/04A RU2002128740A RU2002128740A RU 2002128740 A RU2002128740 A RU 2002128740A RU 2002128740/04 A RU2002128740/04 A RU 2002128740/04A RU 2002128740 A RU2002128740 A RU 2002128740A RU 2002128740 A RU2002128740 A RU 2002128740A
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complex
hydroformylation
bis
ruthenium
ethane
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RU2002128740/04A
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RU2257262C2 (ru
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Кевин Дейл АЛЛЕН (US)
Кевин Дейл АЛЛЕН
Джон Фредерик НИФТОН (US)
Джон Фредерик НИФТОН
Джозеф Браун ПАУЭЛЛ (US)
Джозеф Браун Пауэлл
Линн Хенри СЛОУ (US)
Линн Хенри СЛОУ
Толмадж Гейл ДЖЕЙМС (US)
Толмадж Гейл ДЖЕЙМС
Пол Ричард ВЕЙДЕР (US)
Пол Ричард Вейдер
Тимоти Скотт УИЛЛЬЯМС (US)
Тимоти Скотт УИЛЛЬЯМС
Original Assignee
Шелл Интернэшнл Рисерч Маатсхаппий Б.В. (NL)
Шелл Интернэшнл Рисерч Маатсхаппий Б.В.
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    • 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
    • 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
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • 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
    • 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
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • B01J31/2414—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
    • 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
    • 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
    • C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/48—Ring-opening 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
    • B01J2531/821—Ruthenium
    • 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
    • B01J2531/84—Metals of the iron group
    • B01J2531/845—Cobalt
    • 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
    • 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
    • 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
    • Y02P20/584—Recycling of catalysts

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Saccharide Compounds (AREA)

Claims (10)

1. Способ получения катализатора гидроформилирования, который включает a) получение комплекса (А) контактированием соединения рутения (0) с дитретичным фосфиновым лигандом, и b) получение комплекса (В) в результате окислительно-восстановительной реакции комплекса (А) с карбонильным соединением кобальта (0).
2. Способ по п.1, где дитретичный фосфиновый лиганд имеет общую формулу
Figure 00000001
где каждая группа R и R’ независимо или вместе представляет углеводородный фрагмент, содержащий вплоть до 30 атомов углерода;
Q представляет органическую мостиковую группу длиной от 2 до 4 атомов.
3. Способ по п.2, где группы R и R’ каждая независимо представляет алкильную, циклоалкильную, бициклоалкильную или арильную группу.
4. Способ по п.2 или 3, где группа Q включает атомы углерода.
5. Способ по п.4, где Q представляет алкиленовую группу длиной в 2, 3 или 4 атома углерода.
6. Способ по любому из пп.1-5, где дитретичный фосфиновый лиганд выбирают из одного или более из 1,2-бис-(дициклогексилфосфино)этана,
1,2-бис(дифенилфосфино)этана, 1,2-бис(диэтилфосфино)этана,
1-(диэтилфосфино)-3-(дибутилфосфино)пропана,
1,2-бис(дифенилфосфино)бензола,
1,2-бис-(диметилфосфино)этана,
1,2-бис(2,4,4-триметилпентилфосфино)этана,
1,2-бис(диизобутилфосфино)этана,
1,2-Р,Р’-бис(9-фосфабицикло[3.3.1] и/или [4.2.1]нонил)этана,
их 1,2-Р,Р’-пропанового или их 1,3-Р,Р’-пропанового аналогов.
7. Катализатор гидроформилирования, полученный способом, который включает a) получение комплекса (А) в результате контактирования рутения (0) с дитретичным фосфиновым лигандом, и b) получение комплекса (В) в результате окислительно-восстановительной реакции комплекса (А) с карбонильным соединением кобальта (0).
8. Одностадийный способ гидроформилирования для получения 1,3-диола, включающий реакцию взаимодействия оксирана с синтетическим газом в условиях гидроформилирования в инертном растворителе в присутствии катализатора гидроформилирования, полученного способом, который включает a) получение комплекса (А) в результате контактирования рутения (0) с дитретичным фосфиновым лигандом, и b) получение комплекса (В) в результате окислительно-восстановительной реакции комплекса (А) с карбонильньм соединением кобальта (0).
9. Одностадийный способ гидроформилирования для получения 1,3-диола, включающий реакцию оксирана с синтетическим газом в условиях гидроформилирования инертном растворителе в присутствии катализатора гидроформилирования, который представляет собой бидентатный комплекс рутений (+1)-фосфин: кобальт (-1), где лигированным металлом является рутений, в условиях, которые предпочтительно после завершения реакции оксиран/синтетический газ вызывают фазовое разделение реакционной смеси на верхнюю фазу растворителя с высоким содержанием катализатора и нижнюю фазу растворителя с высоким содержанием 1,3-диола, рециклизацию верхней фазы с высоким содержанием катализатора непосредственно в реакцию гидроформилирования для дальнейшей реакции с непрореагировавшими ранее исходными материалами, и выделение 1,3-диола из нижней фазы с высоким содержанием 1,3-диола.
10. Катализатор гидроформилирования, который представляет собой бидентатный комплекс рутений(+1)-фосфин : кобальт(-1), где лигированным металлом является рутений.
RU2002128740/04A 2000-03-27 2001-03-27 Одностадийный способ получения 1,3-диола RU2257262C2 (ru)

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US6750373B2 (en) * 2001-05-18 2004-06-15 Shell Oil Company One-step production of 1, 3-propanediol from ethylene oxide and syngas with a cobalt-iron catalyst
TW593239B (en) * 2001-06-04 2004-06-21 Kevin Dale Allen One-step production of 1,3-propanediol from ethylene oxide and syngas with a catalyst with a phospholanoalkane ligand
US6660892B2 (en) * 2002-02-13 2003-12-09 Shell Oil Company Synthesis of aliphatic 1,3-diols utilizing reduced ligand concentration and water extraction
US7056439B2 (en) * 2003-05-06 2006-06-06 Tate & Lyle Ingredidents Americas, Inc. Process for producing 1, 3-propanediol
US7615671B2 (en) 2007-11-30 2009-11-10 Eastman Chemical Company Hydrogenation process for the preparation of 1,2-diols
US8886112B2 (en) 2008-09-24 2014-11-11 Apple Inc. Media device with enhanced data retrieval feature
KR101127730B1 (ko) 2009-12-10 2012-03-22 호남석유화학 주식회사 계면활성제를 이용한 1,3-프로판디올 제조방법

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US4253987A (en) 1980-04-10 1981-03-03 Union Carbide Corporation Homologation process for the production of ethanol from methanol
US4451680A (en) * 1982-10-21 1984-05-29 Texaco Inc. Alcohols prepared from olefins and synthesis gas
US4895987A (en) 1986-06-06 1990-01-23 Sun Refining And Marketing Company Phosphonite-and phosphonite-promoted ruthenium - cobalt catalysts for the dealkoxyhydroxymethylation of acetals to form glycol ethers
US4873378A (en) 1986-08-20 1989-10-10 Hoechst Celanese Corporation Process for making 1,3-diols from epoxides
US5053562A (en) 1990-07-31 1991-10-01 Hoechst Celanese Corporation Process for making 1,3-diols from epoxides
US5200539A (en) * 1990-08-27 1993-04-06 Louisiana State University Board Of Supervisors, A Governing Body Of Louisiana State University Agricultural And Mechanical College Homogeneous bimetallic hydroformylation catalysts, and processes utilizing these catalysts for conducting hydroformylation reactions
US5304691A (en) * 1993-07-13 1994-04-19 Shell Oil Company Process for making 1,3-propanediol and 3-hydroxypropanal

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ATE266470T1 (de) 2004-05-15
EP1268060B1 (en) 2004-05-12
US6706656B2 (en) 2004-03-16
KR20020084259A (ko) 2002-11-04
DE60103263T2 (de) 2005-05-25
CN1635987A (zh) 2005-07-06
RU2257262C2 (ru) 2005-07-27
US6469222B2 (en) 2002-10-22
KR100768594B1 (ko) 2007-10-18
JP2003528717A (ja) 2003-09-30
WO2001072675A3 (en) 2002-01-03
EP1268060A2 (en) 2003-01-02
US20020161251A1 (en) 2002-10-31
CN1318362C (zh) 2007-05-30
US6518466B2 (en) 2003-02-11
US6468940B1 (en) 2002-10-22
US20020004617A1 (en) 2002-01-10
WO2001072675A2 (en) 2001-10-04
CA2404758A1 (en) 2001-10-04
BR0109659A (pt) 2004-06-22

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