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RU2004117527A - Способ теломеризации диена с сопряженными двойными связями, катализатор и бидентатный лиганд, используемые в указанном способе - Google Patents

Способ теломеризации диена с сопряженными двойными связями, катализатор и бидентатный лиганд, используемые в указанном способе Download PDF

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RU2004117527A
RU2004117527A RU2004117527/04A RU2004117527A RU2004117527A RU 2004117527 A RU2004117527 A RU 2004117527A RU 2004117527/04 A RU2004117527/04 A RU 2004117527/04A RU 2004117527 A RU2004117527 A RU 2004117527A RU 2004117527 A RU2004117527 A RU 2004117527A
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bis
bidentate ligand
group
propane
independently mean
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RU2004117527/04A
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RU2318790C2 (ru
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Эйт ДРЕНТ (NL)
Эйт Дрент
Михель Рольф ЭБЕРХАРД (US)
Михель Рольф ЭБЕРХАРД
ДЕР МАДЕ Рената Хелена ВАН (NL)
ДЕР МАДЕ Рената Хелена ВАН
Пол Джерард ПРИНГЛ (GB)
Пол Джерард Прингл
Original Assignee
Шелл Интернэшнл Рисерч Маатсхаппий Б.В. (NL)
Шелл Интернэшнл Рисерч Маатсхаппий Б.В.
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    • 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
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    • B01J31/1895—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing arsenic or antimony
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    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
    • C07C2/08—Catalytic processes
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    • C07C2/36—Catalytic processes with hydrides or organic compounds as phosphines, arsines, stilbines or bismuthines
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    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/38—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes
    • C07C2/40—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes of conjugated dienes
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
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    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
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    • C07D201/08—Preparation of lactams from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
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    • 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
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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    • 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
    • C07F9/6568—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 atoms as the only ring hetero atoms
    • C07F9/65683—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 atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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Claims (10)

1. Способ теломеризации диена с сопряженными двойными связями, где диен с сопряженными двойными связями взаимодействует с соединением, содержащим активный атом водорода и имеющим формулу R-H, в присутствии катализатора теломеризации на основе
(a) источника металла VIII группы,
(b) бидентатного лиганда, где бидентатный лиганд имеет общую формулу (I)
R1R2M1-R-M2R3R4, (I)
в которой M1 и M2 независимо означают P, As или Sb;
R1, R2, R3 и R4 независимо означают одновалентную алифатическую группу, или R1, R2 и M1 вместе и/или R3, R4 и M2 вместе независимо означают необязательно замещенную алифатическую циклическую группу, по меньшей мере, с 5 атомами в цикле, из которых один означает атом M1 или M2 соответственно;
R означает двухвалентную органическую мостиковую группу.
2. Способ по п.1, где диен с сопряженными двойными связями означает 1,3-бутадиен.
3. Способ по п.1 или 2, где содержащее активный водород соединение означает воду, алканол или гидрокси-ароматическое соединение.
4. Бидентатный лиганд формулы (II),
R1R2M1-V-M2R3R4, (II)
где M1 и M2 независимо означают P, As или Sb;
R1, R2 и M1 вместе и/или R3, R4 и M2 вместе независимо означают необязательно замещенную алифатическую циклическую группу, по меньшей мере, с 5 атомами в цикле, из которых один означает атом M1 или M2 соответственно;
V означает мостиковую группу, состоящую из триметиленовой группы, связанной с M1 или M2, средний атом углерода которой имеет две дополнительные связи с неводородным атомом.
5. Бидентатный лиганд по п.4, где бидентатный лиганд выбирают из группы, включающей
2,2-диметил-1,3-бис-(1,4-циклооктиленфосфино)пропан, 2-метил-2-гидроксиметил-1,3-бис-(1,4-циклооктиленфосфино)пропан или 2,2-дигидроксиметил-1,3-бис-(1,4-циклооктиленфосфино)пропан, 2,2-диметил-1,3-бис-(1,5-циклооктиленфосфино)пропан, 2-метил-2-гидроксиметил-1,3-бис-(1,5-циклооктиленфосфино)пропан или 2,2-дигидроксиметил-1,3-бис-(1,5-циклооктиленфосфино)пропан.
6. Бидентатный лиганд формулы (III),
Q1Q2M1-Q5-Ar1-Ar2-Q6-M2Q3Q4, (III)
где M1 и M2 независимо означают P, As или Sb;
Q1, Q2 и M1 вместе и Q3, Q4 и M2 вместе независимо означают необязательно замещенную алифатическую циклическую группу с 6-20 атомами в цикле, из которых один означает атом M1 или M2 соответственно;
каждый из Q5 и Q6 независимо означает необязательно замещенные алкиленовые группы;
Ar1 и Ar2 независимо означают необязательно замещенную ароматическую группу.
7. Бидентатный лиганд по п.6, где бидентатный лиганд означает 2,2'-бис-(1,4-циклооктиленфосфинометил)-1,1'-дифенил или 2,2'-бис-(1,5-циклооктиленфосфинометил)-1,1'-дифенил.
8. Каталитическая система, содержащая
I) источник металла VIII группы,
II) бидентатный лиганд по одному из пп.4-7.
9. Способ по п.1, выполняемый в присутствии катализатора по п.8.
10. Способ получения 1-октена, включающий
(a) теломеризацию 1,3-бутадиена по одному из пп.1-3 или 9 с образованием 1-замещенного-2,7-октадиена;
(b) гидрирование 1-замещенного-2,7-октадиена со стадии a), дающее 1-замещенный октан;
(c) расщепление 1-замещенного октана со стадии b) с образованием 1-октена.
RU2004117527/04A 2001-11-09 2002-11-05 Способ теломеризации диена с сопряженными двойными связями, катализатор и бидентатный лиганд, используемые в указанном способе RU2318790C2 (ru)

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US (3) US6794553B2 (ru)
EP (1) EP1444176A2 (ru)
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AR (1) AR037280A1 (ru)
AU (1) AU2002363379A1 (ru)
BR (1) BR0213955A (ru)
CA (1) CA2466239A1 (ru)
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US20030130544A1 (en) 2003-07-10
AR037280A1 (es) 2004-11-03
US7491859B2 (en) 2009-02-17
CN100430344C (zh) 2008-11-05
CZ2004586A3 (cs) 2004-08-18
RU2318790C2 (ru) 2008-03-10
WO2003040065A3 (en) 2004-01-22
CA2466239A1 (en) 2003-05-15
CN1592725A (zh) 2005-03-09
US6794553B2 (en) 2004-09-21
BR0213955A (pt) 2004-08-31
WO2003040065A2 (en) 2003-05-15
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US7057082B2 (en) 2006-06-06
US20040242949A1 (en) 2004-12-02
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EP1444176A2 (en) 2004-08-11

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