JPH10507165A - 1,3−アルカンジオールと3−ヒドロキシアルデヒドの調製方法 - Google Patents
1,3−アルカンジオールと3−ヒドロキシアルデヒドの調製方法Info
- Publication number
- JPH10507165A JPH10507165A JP8511401A JP51140196A JPH10507165A JP H10507165 A JPH10507165 A JP H10507165A JP 8511401 A JP8511401 A JP 8511401A JP 51140196 A JP51140196 A JP 51140196A JP H10507165 A JPH10507165 A JP H10507165A
- Authority
- JP
- Japan
- Prior art keywords
- cobalt
- acetate
- reaction
- catalyst
- weight
- 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.)
- Granted
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Classifications
-
- 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
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.コバルトに基づく触媒と第V族元素の親油性第4級塩である促進剤の存在 下にて、オキシランを一酸化炭素及び水素でヒドロホルミル化することにより、 1,3−アルカンジオールと3−ヒドロキシアルデヒドを調製する方法。 2.オキシランが、2〜30個までの炭素原子を有するヒドロカルビル−エポ キシドである請求の範囲1記載の方法。 3.オキシランがエチレンオキシドである請求の範囲1記載の方法。 4.不活性かつ実質的に水非混和性の溶剤の存在下にて行う請求の範囲1〜3 のいずれか一項に記載の方法。 5.溶剤が、式(1) R1−O−R2 (1) (式中、R1は水素、線状、分枝状、環状または芳香族C1-20ヒドロカルビルあ るいはモノ−またはポリ−アルキレンオキシドであり、R2は線状、分枝状、環 状または芳香族C1-20ヒドロカルビル、アルコキシあるいはモノ−またはポリ− アルキレンオキシドであるか、あるいはR1とR2とOとで環状エーテルを形成す る)に相当するアルコールまたはエーテルである請求の範囲4記載の方法。 6.溶剤が、式(2) (式中、R1は水素またはC1-8ヒドロカルビルであり、R3、R4及びR5はC1-8 ヒドロカルビル、アルコキシあるいはモノ−またはポリ−アルキレンオキシドか らそれぞれ選ばれる)に相当するアルコールまたはエーテルである請求の範囲4 記載の方法。 7.コバルトに基づく触媒が、未変性(即ち、非ホスフィン配位)コバルトカ ルボニル化合物である請求の範囲1〜6のいずれか一項に記載の方法。 8.コバルトに基づく触媒の量が、反応混合物の重量に対して0.01〜1. 0重量%である請求の範囲1〜7のいずれか一項に記載の方法。 9.第V族カチオンの親油性第4級塩が、式(3) (式中、各R基は未置換及び不活性置換C1-25線状、分枝状、環状または芳香族 ヒドロカルビル、アルコキシ、あるいはモノ−またはポリ−アルキレンオキシド からそれぞれ選ばれ、Mは第V族原子であって好ましくは窒素、燐または砒素原 子であり、AはpKaが2よりも高い共役酸を有する塩基性アニオンである)で 表される請求の範囲1〜8のいずれか一項に記載の方法。 10.親油性第4級塩を、酢酸ベンジルトリ(n−ブチル)アンモニウム、ベ ンジルトリメチルアンモニウムメトキシド、水酸化ベンジルトリメチルアンモニ ウム及びエトキシル化第4級アンモニウム塩、酢酸テトラ(n−ブチル)ホスホ ニウム、酢酸テトラオクチルホスホニウム、水酸化テトラフェニルホスホニウム 及び酢酸ベンジルトリメチルホスホニウム、並びに酢酸テトラフェニルアルソニ ウム、酢酸テトラ(n−ブチル)アルソニウム、及び酢酸テトラオクチルアルソ ニウムから選択する請求の範囲9記載の方法。 11.第V族元素の親油性第4級塩が、コバルト1モル当たり0.01〜0. 6モルの量で含まれる請求の範囲1〜10のいずれか一項に記載の方法。 12.溶剤に1.0〜2.5重量%の水が含まれている請求の範囲4〜11の いずれか一項に記載の方法。 13.オキシランを、モル比1:2〜8:1の水素と一酸化炭素でヒドロホル ミル化する請求の範囲1〜12のいずれか一項に記載の方法。 14.反応混合物中における3−ヒドロキシアルデヒドのレベルを15重量% 未満に維持する請求の範囲1〜13のいずれか一項に記載の方法。 15.ヒドロホルミル化反応を100℃未満の温度かつ3.5〜34.6MPa の圧力にて行う請求の範囲1〜14のいずれか一項に記載の方法。 16.ヒドロホルミル化物を水性液体での抽出により分離する請求の範囲1〜 15のいずれか一項に記載の方法。 17.水:混合物の重量比が1:1〜1:20となるように水をヒドロホルミ ル化反応生成物混合物へ添加する請求の範囲16記載の方法。 18.コバルトに基づく触媒をリサイクルする請求の範囲16記載の方法。 19.3−ヒドロキシアルデヒドを水素化して1,3−アルカンジオールを生 成させる請求の範囲1〜18のいずれか一項に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US316,661 | 1994-09-30 | ||
US08/316,673 US5463145A (en) | 1994-09-30 | 1994-09-30 | Process for preparing 1,3-propanediol |
US08/316,661 US5545765A (en) | 1994-09-30 | 1994-09-30 | Cobalt-catalyzed process for preparing 1,3-propanediol using a lipophilic quaternary arsonium salt promoter |
US316,673 | 1994-09-30 | ||
PCT/EP1995/003868 WO1996010550A1 (en) | 1994-09-30 | 1995-09-28 | Process for preparing 1,3-alkanediols and 3-hydroxyaldehydes |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH10507165A true JPH10507165A (ja) | 1998-07-14 |
JP3779729B2 JP3779729B2 (ja) | 2006-05-31 |
Family
ID=26980535
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP51140196A Expired - Fee Related JP3779729B2 (ja) | 1994-09-30 | 1995-09-28 | 1,3−アルカンジオールと3−ヒドロキシアルデヒドの調製方法 |
Country Status (24)
Country | Link |
---|---|
EP (1) | EP0783475B1 (ja) |
JP (1) | JP3779729B2 (ja) |
KR (1) | KR100393706B1 (ja) |
CN (1) | CN1089083C (ja) |
AT (1) | ATE174319T1 (ja) |
AU (1) | AU689963B2 (ja) |
BR (1) | BR9509054A (ja) |
CA (1) | CA2201305C (ja) |
CZ (1) | CZ289381B6 (ja) |
DE (1) | DE69506573T2 (ja) |
DK (1) | DK0783475T3 (ja) |
ES (1) | ES2125665T3 (ja) |
FI (1) | FI971267A (ja) |
HU (1) | HUT77463A (ja) |
MX (1) | MX9702278A (ja) |
MY (1) | MY112931A (ja) |
NO (1) | NO307561B1 (ja) |
NZ (1) | NZ294240A (ja) |
PL (1) | PL181433B1 (ja) |
RU (1) | RU2149156C1 (ja) |
SK (1) | SK281399B6 (ja) |
TR (1) | TR199501190A2 (ja) |
TW (1) | TW442458B (ja) |
WO (1) | WO1996010550A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1074405C (zh) * | 1994-09-30 | 2001-11-07 | 国际壳牌研究有限公司 | 制备1,3-链烷二醇和3-羟基醛的方法 |
DE10065176A1 (de) * | 2000-12-23 | 2002-06-27 | Degussa | Katalysator und Verfahren zur Herstellung von niedrigviskosen und farbreduzierten isocyanuratgruppenhaltigen Polyisocyanaten |
US20090163742A1 (en) * | 2007-12-19 | 2009-06-25 | Stephen Blake Mullin | Heterogeneous promotion of oxirane hydroformylation |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3687981A (en) * | 1968-01-17 | 1972-08-29 | Du Pont | Process for making a dioxane |
US4973741A (en) * | 1989-06-29 | 1990-11-27 | Eastman Kodak Company | Difunctional products from ethylene oxide and synthesis gas |
DE69410442T2 (de) * | 1993-02-05 | 1998-10-15 | Shell Int Bv | Verfahren zur herstellung von 1,3-diolen und 3-hydroxyaldehyden |
US5256827A (en) * | 1993-02-05 | 1993-10-26 | Shell Oil Company | Process for making 3-hydroxypropanal and 1,3-propanediol |
DE69506580T2 (de) * | 1994-09-30 | 1999-06-17 | Shell Int Research | Verfahren zur herstellung von 1,3-alkandiolen und 3-hydroxyaldehyden |
CN1074405C (zh) * | 1994-09-30 | 2001-11-07 | 国际壳牌研究有限公司 | 制备1,3-链烷二醇和3-羟基醛的方法 |
-
1995
- 1995-09-28 NZ NZ294240A patent/NZ294240A/xx unknown
- 1995-09-28 ES ES95934652T patent/ES2125665T3/es not_active Expired - Lifetime
- 1995-09-28 MY MYPI95002897A patent/MY112931A/en unknown
- 1995-09-28 CN CN95195315A patent/CN1089083C/zh not_active Expired - Fee Related
- 1995-09-28 CZ CZ1997943A patent/CZ289381B6/cs not_active IP Right Cessation
- 1995-09-28 KR KR1019970702071A patent/KR100393706B1/ko not_active IP Right Cessation
- 1995-09-28 AT AT95934652T patent/ATE174319T1/de not_active IP Right Cessation
- 1995-09-28 DK DK95934652T patent/DK0783475T3/da active
- 1995-09-28 PL PL95319438A patent/PL181433B1/pl unknown
- 1995-09-28 JP JP51140196A patent/JP3779729B2/ja not_active Expired - Fee Related
- 1995-09-28 MX MX9702278A patent/MX9702278A/es unknown
- 1995-09-28 RU RU97106785A patent/RU2149156C1/ru not_active IP Right Cessation
- 1995-09-28 BR BR9509054A patent/BR9509054A/pt not_active IP Right Cessation
- 1995-09-28 AU AU36993/95A patent/AU689963B2/en not_active Ceased
- 1995-09-28 WO PCT/EP1995/003868 patent/WO1996010550A1/en active IP Right Grant
- 1995-09-28 CA CA002201305A patent/CA2201305C/en not_active Expired - Fee Related
- 1995-09-28 EP EP95934652A patent/EP0783475B1/en not_active Expired - Lifetime
- 1995-09-28 SK SK389-97A patent/SK281399B6/sk unknown
- 1995-09-28 HU HU9702306A patent/HUT77463A/hu unknown
- 1995-09-28 DE DE69506573T patent/DE69506573T2/de not_active Expired - Fee Related
- 1995-09-29 TR TR95/01190A patent/TR199501190A2/xx unknown
-
1996
- 1996-02-08 TW TW085101552A patent/TW442458B/zh not_active IP Right Cessation
-
1997
- 1997-03-25 NO NO971420A patent/NO307561B1/no unknown
- 1997-03-26 FI FI971267A patent/FI971267A/fi unknown
Also Published As
Publication number | Publication date |
---|---|
EP0783475B1 (en) | 1998-12-09 |
ATE174319T1 (de) | 1998-12-15 |
RU2149156C1 (ru) | 2000-05-20 |
NO971420D0 (no) | 1997-03-25 |
NO307561B1 (no) | 2000-04-25 |
NZ294240A (en) | 1998-12-23 |
FI971267A0 (fi) | 1997-03-26 |
MY112931A (en) | 2001-10-31 |
MX9702278A (es) | 1997-06-28 |
CN1161685A (zh) | 1997-10-08 |
TW442458B (en) | 2001-06-23 |
CZ94397A3 (cs) | 1998-02-18 |
CA2201305A1 (en) | 1996-04-11 |
DK0783475T3 (da) | 1999-08-16 |
NO971420L (no) | 1997-03-25 |
PL319438A1 (en) | 1997-08-04 |
BR9509054A (pt) | 1998-06-23 |
CZ289381B6 (cs) | 2002-01-16 |
WO1996010550A1 (en) | 1996-04-11 |
AU689963B2 (en) | 1998-04-09 |
PL181433B1 (pl) | 2001-07-31 |
SK281399B6 (sk) | 2001-03-12 |
DE69506573D1 (de) | 1999-01-21 |
HUT77463A (hu) | 1998-05-28 |
EP0783475A1 (en) | 1997-07-16 |
TR199501190A2 (tr) | 1996-06-21 |
DE69506573T2 (de) | 1999-06-17 |
ES2125665T3 (es) | 1999-03-01 |
AU3699395A (en) | 1996-04-26 |
CA2201305C (en) | 2007-09-11 |
KR100393706B1 (ko) | 2003-11-20 |
FI971267A (fi) | 1997-03-26 |
CN1089083C (zh) | 2002-08-14 |
JP3779729B2 (ja) | 2006-05-31 |
SK38997A3 (en) | 1997-11-05 |
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