JP2005519968A - 新規なホスオキソファイト配位子及びカルボニル化方法におけるそれらの使用 - Google Patents
新規なホスオキソファイト配位子及びカルボニル化方法におけるそれらの使用 Download PDFInfo
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- JP2005519968A JP2005519968A JP2003576449A JP2003576449A JP2005519968A JP 2005519968 A JP2005519968 A JP 2005519968A JP 2003576449 A JP2003576449 A JP 2003576449A JP 2003576449 A JP2003576449 A JP 2003576449A JP 2005519968 A JP2005519968 A JP 2005519968A
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- phosoxophyte
- carbonylation
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- transition metal
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- 238000000034 method Methods 0.000 title claims abstract description 129
- 230000008569 process Effects 0.000 title claims abstract description 97
- 239000003446 ligand Substances 0.000 title claims abstract description 96
- 238000005810 carbonylation reaction Methods 0.000 title claims abstract description 78
- 230000006315 carbonylation Effects 0.000 title claims abstract description 74
- 239000000203 mixture Substances 0.000 claims abstract description 94
- 239000003054 catalyst Substances 0.000 claims abstract description 59
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 57
- 150000003624 transition metals Chemical class 0.000 claims abstract description 56
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 55
- 239000012018 catalyst precursor Substances 0.000 claims abstract description 12
- -1 chloro, bromo, iodo, methyl Chemical group 0.000 claims description 78
- 239000001257 hydrogen Substances 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 44
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical group [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 42
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 40
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 33
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- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- WOAZEKPXTXCPFZ-UHFFFAOYSA-N dimethyl(phenyl)azanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1 WOAZEKPXTXCPFZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
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- CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
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- 239000012634 fragment Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 238000004949 mass spectrometry Methods 0.000 description 1
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- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005499 phosphonyl group Chemical group 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
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- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
-
- 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
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- 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
- C07C45/50—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 by oxo-reactions
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
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- 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
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
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- 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
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
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- 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
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- C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
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- 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
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
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- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
で表されるジクロロ−ビスホスファイト組成物を、式V:
で表されるヒドロキシ酸と接触させることを含んでなる、式IIaのホスオキソファイト組成物を製造するための新規な合成方法であって、組成物IVと組成物Vとの接触は、式IIaのホスオキソファイト組成物を製造するのに充分な反応条件下で実施する。本発明の前記合成方法は、前述の新規ホスオキソファイト組成物IIaを有利に且つ効率よく製造する。式IIbの組成物も同様に製造できる。
で表される。
ホスオキソファイトA
ホスオキソファイトM
式V:
を有する2,2’−ホスホロモノクロリダイトの新規な合成方法を提供する。組成物VIのホスホロモノクロリダイトは、式IIaの新規ホスオキソファイト組成物の合成に使用される式IVのジクロロ−ビスホスファイト組成物の製造において、出発原料として有用である。式VIのホスホロモノクロリダイト、特に大きくて、嵩高い置換基を有するそれらの種の合成は、当業界において見つけることができる。しかし、通常は、先行技術の方法は、小さくて、あまり嵩高くない置換基、例えば水素、ハロゲン及び低級アルキル直鎖部分、例えばメチル及びエチルを有する種の合成には不適当である。従って、本質的に全ての種(species)に適用できるが、水素、ハロゲン及びC1-10第一アルキル基のような比較的小さく、あまり嵩高くない置換基を有する種に特に適用できる、式VIのホスホロモノクロリダイト組成物のための新規な合成が本発明において提供される。好ましい方法は、N,N−ジメチルアニリンの存在下、式VIのホスホロモノクロリダイト組成物を製造するのに十分な反応条件下において対応する2,2’−ビフェノールVII:
を化学量論量又は過剰量の三塩化リン(PCl3)と接触させることを含んでなる。典型的には、概ね化学量論量のビフェノールVII、PCl3及び塩基(1:1:2)を用いるが、化学量論より多い量のPCl3及び塩基も使用できる。反応自体を妨げることなく試薬を可溶化する任意の溶媒、例えばエーテル、アルカン及び芳香族炭化水素を使用できる。好ましくは、溶媒はテトラヒドロフラン、ジエチルエーテル、トルエン及びそれらの混合物から選ばれる。溶媒中の試薬の濃度はいずれの場合にも、約0.01重量%超、好ましくは約0.1重量%超〜約20重量%未満、好ましくは約10重量%未満である。この方法は典型的には約−78℃より高い、好ましくは約−40℃より高い温度で実施する。この方法は典型的には約60℃未満、好ましくは約40℃未満の温度で実施する。一般に、この方法は周囲圧力で実施するが、これより高圧又は低圧も、所望ならば使用できる。窒素、アルゴン又はヘリウムのような不活性雰囲気のブランケット下における反応が好ましい。
ホスホロモノクロリダイトの製造
下記式の3,3’−ジ−t−ブチル−5,5’−ジ−t−ピバロイルオキシ−2,2’−ビフェニルホスホロモノクロリダイト(PIV−PCl)を以下のようにして製造した。
式Mのホスオキソファイト組成物の製造
下記式を有するジクロロ−ビスホスファイト組成物(PIV−TMS−PCl2)を以下のようにして調製した。
有機ホスオキソファイト配位子及びヒドロホルミル化方法
前に最も好ましい例において示したホスオキソファイト配位子N、O、Q、R、FF及びGGを、実施例2のホスオキソファイト組成物Mに関して示した製造と同様にして合成した。以下の具体的反応体を用いた。
ホスオキソファイト組成物DD及びZを、実施例2の合成と同様にして製造した。使用した具体的試薬は以下の通りであった。
前述のホスオキソファイト組成物AAを、実施例2に記載したのと同様な方法で合成した。具体的には、3,3’−トリメチルシリル−5,5’−ジ−t−ブチル−2,2’−ビフェノールを三塩化リンと反応させて、対応するTMS−PClホスホロモノクロリダイトを生成し、それを3,3’−ジ−t−ブチル−5,5’−ジ(2,4,6−トリメチルフェニル)−2,2’−ビフェノール及び三塩化リンと反応させて対応するジクロロ−ビホスファイトを生成し、それを3,5−ジブロモサリチル酸と反応させてホスオキソファイト組成物AAを生成した。精製収率:83%。31P{1H}NMRスペクトルにおいて2つのジアステレオマーが87:13に近い比で観察された。31P{1H}NMR(121.66MHz,CDCl3,δ):ジアステレオマー1(87%):119.88及び145.15ppm(d,JP-P=4.5Hz);ジアステレオマー2(13%):115.00及び143.49ppm(d,JP-P=8.5Hz)。
Claims (40)
- 各A及びZが、独立に、水素、ハロ、アルキル、アリール、アルカリール、アルアルキル、脂環基、アルコキシ、アリールオキシ、ヒドロカルビルカルボニル、ヒドロカルビルカルボキシ及びトリ(ヒドロカルビル)シリル基からなる群から選ばれ、前記ヒドロカルビル又はトリ(ヒドロカルビル)シリル基は炭素数が1〜約20であり;各B及びYは、独立に、オルト位に置換基を有しアリール基、tert−アルキル基及びトリ(ヒドロカルビル)シリル基から選ばれ、Yは炭素数が3〜約30である請求項1に記載の組成物。
- 各Aが、独立に、水素、クロロ、ブロモ、ヨード、メチル、エチル、tert−ブチル、イソアミル、tert−アミル、tert−オクチル、メトキシ、アセチル[CH3C(O)−]、プロピオニル[CH3CH2C(O)−]及びトリメチルアセトキシ[(CH3)3C−C(O)O−]基から選ばれ;各Zは、独立に、tert−ブチル、tert−アミル、tert−オクチル、トリ(メチル)シリル、トリ(エチル)シリル、キシリル、ジメチルフェニル、ジエチルフェニル、トリメチルフェニル及びトリメチルアセトキシ基から選ばれる請求項1に記載の組成物。
- 各Bが、独立に、tert−ブチル、トリメチルシリル、フェニル、3,5−ジメチルフェニル及び3,4,5−トリメチルフェニル基から選ばれ、各Yが、独立に、tert−ブチル及びトリメチルシリル基から選ばれる請求項1に記載の組成物。
- 両方のBがトリ(ヒドロカルビル)シリル基であるか、又は両方のYがトリ(ヒドロカルビル)シリル基である請求項1に記載の組成物。
- Xがメチレン(−CH2−)、エチレン(−CH2CH2−)、1,3−プロピレン(−CH2CH2CH2−)、1,2−フェニレン(−C6H4−)、1,2−ナフチレン(−C10H6−)、2,3−ナフチレン(−C10H6)、3,5−ジクロロ−1,2−フェニレン、3,5−ジブロモ−1,2−フェニレン、3−ヨード−5−メチル−1,2−フェニレン、3,5−ジイソプロピル−1,2−フェニレン、3,5,6−トリクロロ−1,2−フェニレン、3−フェニル−1,2−フェニレン、1,1−ジエチル−1,1−メチレン、1,1−シクロへキシリデン、1,1−シクロへプチリデン及び3−イソプロピル−6−メチル−1,2−フェニレンからなる群から選ばれたアルキル又はアリールジラジカルである請求項1に記載の組成物。
- 各R1が水素、C1-6アルキル及びフェニル基からなる群から選ばれる請求項1に記載の組成物。
- ジクロロ−ビスホスファイト化合物対ヒドロキシ酸のモル比が約0.7/1より大きく且つ約1.3/1未満である請求項11に記載の方法。
- 前記塩基がトリアルキルアミン及びN−複素環化合物から選ばれる請求項11に記載の方法。
- ジクロロ−ビスホスファイトに対する塩基のモル比が約2.2/1より大きいが約2.7/1未満である請求項11に記載の方法。
- 前記温度が約−35℃より大きく且つ約60℃未満である請求項11に記載の方法。
- 請求項1の式から選ばれたホスオキソファイト配位子の少なくとも1つの分子に結合し、場合によっては、一酸化炭素、水素又は一酸化炭素と水素の両方に結合した第VIII族遷移金属を更に含んでなる遷移金属錯体触媒又は錯体触媒前駆体。
- 前記第VIII族遷移金属がルテニウム、ロジウム、コバルト及びイリジウムから選ばれる請求項16に記載の組成物。
- 前記第VIII族遷移金属がロジウムである請求項16に記載の組成物。
- 前記ホスオキソファイト配位子が請求項10に記載の組成物から選ばれる請求項16に記載の組成物。
- 有機溶媒、遊離ホスオキソファイト配位子及びホスオキソファイト配位子の少なくとも1つの分子に結合した第VIII族遷移金属を含む遷移金属錯体触媒又は錯体触媒前駆体組成物を含んでなる溶液であって、前記遊離及び結合ホスオキソファイト配位子が請求項1の式から選ばれる溶液。
- 前記第VIII族遷移金属がルテニウム、ロジウム、コバルト及びイリジウムからなる群から選ばれる請求項20に記載の溶液。
- 前記第VIII族遷移金属がロジウムである請求項20に記載の溶液。
- 前記遊離及び結合ホスオキソファイト配位子が独立に請求項10に示されたホスオキソファイト配位子からなる群から選ばれる請求項20に記載の溶液。
- ホスオキソファイト配位子の少なくとも1つの分子に結合した第VIII族遷移金属を含む遷移金属錯体触媒の存在下に、場合によっては、更に遊離ホスオキソファイト配位子の存在下において、カルボニル化可能な有機化合物を一酸化炭素と接触させることを含んでなるカルボニル化方法であって、前記結合及び遊離ホスオキソファイト配位子が請求項1に示した式から独立して選ばれ、前記接触を対応するカルボニル化有機化合物を製造するのに十分なカルボニル化条件下で実施するカルボニル化方法。
- 前記カルボニル化が単純なカルボニル化、ヒドロホルミル化、ヒドロアシル化、ヒドロシアノ化、ヒドロアミド化、ヒドロエステル化及びヒドロカルボキシル化を含む請求項24に記載のカルボニル化方法。
- 前記第VIII族遷移金属がルテニウム、ロジウム、コバルト及びイリジウムから選ばれる請求項24に記載のカルボニル化方法。
- 前記遊離及び結合ホスオキソファイト配位子が、それぞれ独立に、請求項10に示されたホスオキソファイト配位子から選ばれる請求項24に記載のカルボニル化方法。
- 前記方法がオレフィン性不飽和脂肪族炭化水素を水素の存在下に一酸化炭素と接触させるヒドロホルミル化方法を含む請求項24に記載のカルボニル化方法。
- 前記オレフィン性不飽和脂肪族炭化水素が2〜60個の炭素原子及び1個又はそれ以上の不飽和基を含む請求項28に記載のヒドロホルミル化方法。
- 前記オレフィン性不飽和脂肪族炭化水素がα−オレフィン、内部オレフィン、アルキルアルケノエート、アルケニルアルカノエート、アルケニルアルキルエーテル及びアルケノールからなる群から選ばれる請求項28に記載のカルボニル化方法。
- 前記オレフィン性不飽和脂肪族炭化水素がエチレン、プロピレン、1−ブテン、1−ペンテン、1−ヘキセン、1−オクテン、1−デセン、1−ドデセン、1−オクタデセン、2−ブテン、2−メチルプロペン(イソブチレン)、イソアミレン、2−ペンテン、2−ヘキセン、3−ヘキセン、2−ヘプテン、シクロヘキセン、プロピレン二量体、プロピレン三量体、プロピレン四量体、2−エチルヘキセン、スチレン、3−フェニル−1−プロペン、ブタジエン、1,3−シクロヘキサジエン、1,4−シクロヘキサジエン、1,7−オクタジエン、3−シクロヘキシル−1−ブテン、アリルアルコール、ヘキサ−1−エン−4−オール、オクタ−1−エン−4−オール、酢酸ビニル、酢酸アリル、酢酸3−ブテニル、プロピオン酸ビニル、1−ビニル−3−シクロヘキセン、プロピオン酸アリル、酪酸アリル、メタクリル酸メチル、酢酸3−ブテニル、ビニルエーテル、ビニルメチルエーテル、アリルエチルエーテル、n−プロピル−7−オクテノエート、1−デセン酸メチル、3−ブテネニトリル、5−ヘキセンアミド、オレイン酸メチル、大豆油及びヒマシ油からなる群から選ばれる請求項28に記載のカルボニル化方法。
- 飽和炭化水素、芳香族炭化水素、エーテル、アルデヒド、ケトン、ニトリル及びアルデヒド縮合生成物からなる群から選ばれた溶媒の存在下に、前記カルボニル化方法を実施する請求項24に記載のカルボニル化方法。
- 請求項1に記載の式によって表されるホスオキソファイト配位子から選ばれた遊離ホスオキソファイト配位子の存在下に前記方法を実施する請求項24に記載のカルボニル化方法。
- 第VIII族遷移金属に対するホスオキソファイト配位子のモル比が約3/1より大きく且つ約100/1未満である請求項24に記載のカルボニル化方法。
- 前記カルボニル化プロセス温度が約30℃より高く且つ約200℃未満である請求項24に記載のカルボニル化方法。
- 前記カルボニル化方法の全圧が約1psia(7kPa)より高く且つ約10,000psia(68,948kPa)未満である請求項24に記載のカルボニル化方法。
- 一酸化炭素分圧が約1psia(7kPa)より高く且つ約1,000psia(6,895kPa)未満であり;ヒドロホルミル化方法において水素分圧が約5psia(35psia)より高く且つ約1,000psia(6,895kPa)未満である請求項24に記載のカルボニル化方法。
- 一酸化炭素に対する水素ガスのH2/COモル比が約1/10より大きく且つ約100/1未満である請求項37に記載のカルボニル化方法。
- 前記方法がヒドロホルミル化方法であり、前記プロセス温度が約30℃より高く且つ約150℃未満である請求項28に記載のカルボニル化方法。
- 遷移金属の濃度が約10ppmより高く且つ約1,000ppm未満である請求項24に記載のカルボニル化方法。
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EP1485392A2 (en) | 2004-12-15 |
CN1639177A (zh) | 2005-07-13 |
CN1639177B (zh) | 2010-05-05 |
DE60304034T2 (de) | 2006-10-12 |
AU2003230587A8 (en) | 2003-09-29 |
WO2003078444A3 (en) | 2003-12-18 |
EP1485392B1 (en) | 2006-03-15 |
AU2003230587A1 (en) | 2003-09-29 |
US7196230B2 (en) | 2007-03-27 |
ATE320438T1 (de) | 2006-04-15 |
US20060100453A1 (en) | 2006-05-11 |
JP4694787B2 (ja) | 2011-06-08 |
WO2003078444A2 (en) | 2003-09-25 |
DE60304034D1 (de) | 2006-05-11 |
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