JPWO2020239720A5 - - Google Patents

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JPWO2020239720A5
JPWO2020239720A5 JP2021568559A JP2021568559A JPWO2020239720A5 JP WO2020239720 A5 JPWO2020239720 A5 JP WO2020239720A5 JP 2021568559 A JP2021568559 A JP 2021568559A JP 2021568559 A JP2021568559 A JP 2021568559A JP WO2020239720 A5 JPWO2020239720 A5 JP WO2020239720A5
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carbon
group
formula
additive
alkynol
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Priority claimed from PCT/EP2020/064496 external-priority patent/WO2020239720A1/en
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ホスフィノ基又はホスフィンオキシド基のいずれかを担持する有機リン化合物である添加物の存在下で、担体に担持されたパラジウムである水素化触媒を使用して、アルキノールを、水素により水素化して選択的にアルケノールにする方法であって、前記添加物がホスフィノ基を担持する場合、前記添加物は２つ以上のホスフィノ基を担持することを特徴とする、方法。 The alkynol is selectively hydrogenated with hydrogen using a hydrogenation catalyst that is palladium on a support in the presence of an additive that is an organophosphorus compound that supports either a phosphino group or a phosphine oxide group. to alkenols, characterized in that, when said additive carries phosphino groups, said additive carries two or more phosphino groups. 前記アルキノールが、前記アルキノールの炭素－炭素三重結合に対してアルファ位にある炭素に結合しているヒドロキシル基を有するアルキノールであることを特徴とする、請求項１に記載の方法。 2. The method of claim 1, wherein said alkynol is an alkynol having a hydroxyl group attached to the carbon alpha to the carbon-carbon triple bond of said alkynol. 前記アルキノールの炭素－炭素三重結合が、末端の炭素－炭素三重結合であることを特徴とする、請求項１又は２に記載の方法。 3. Process according to claim 1 or 2, characterized in that the carbon-carbon triple bond of the alkynol is a terminal carbon-carbon triple bond. 前記アルキノールが、式（Ｉ）
Figure 2020239720000001
 のアルキノール、及び式（ＩＩ）
Figure 2020239720000002
 のアルケノールであり、
式中、
Ｒ１は、Ｈ又はメチル基又はエチル基を表し、並びに
Ｒ２は、少なくとも１つの化学官能基を任意選択により含む、飽和又は不飽和の、直鎖若しくは分岐鎖又は環式の、１～４６個のＣ原子を有するヒドロカルビル基を表すか、
又は
Ｒ１及びＲ２は、一緒に５～７員環を形成しているアルキレン基を表すか、
のいずれかであり、
但し、Ｒ１は、式（Ｉ）及び（ＩＩ）において同じ意味を有し、Ｒ２は、式（Ｉ）及び（ＩＩ）において同じ意味を有する
ことを特徴とする、請求項１～３のいずれか一項に記載の方法。 The alkynol is represented by formula (I)
Figure 2020239720000001
 and an alkynol of formula (II)
Figure 2020239720000002
 is an alkenol of
During the ceremony,
R 1 represents H or a methyl or ethyl group and R 2 is saturated or unsaturated, linear or branched or cyclic, 1-46, optionally comprising at least one chemical functional group represents a hydrocarbyl group having 1 C atom, or
or R 1 and R 2 together represent an alkylene group forming a 5- to 7-membered ring, or
is either
provided that R 1 has the same meaning in formulas (I) and (II) and R 2 has the same meaning in formulas (I) and (II). A method according to any one of paragraphs. Ｒ１がメチル基であることを特徴とする、請求項１～４のいずれか一項に記載の方法。 Process according to any one of claims 1 to 4, characterized in that R 1 is a methyl group. Ｒ２がメチル基であることを特徴とする、請求項１～５のいずれか一項に記載の方法。 Process according to any one of claims 1 to 5, characterized in that R 2 is a methyl group. Ｒ２が、式（Ｒ２－Ｉ）、（Ｒ２－ＩＩ）、（Ｒ２－ＩＩＩ）、（Ｒ２－ＩＶ）、（Ｒ２－Ｖ）、（Ｒ２－ＶＩ）及び（Ｒ２－ＶＩＩ）
Figure 2020239720000003
 からなる群から選択され、
式中、点線は、式（Ｒ２－Ｉ）、（Ｒ２－ＩＩ）、（Ｒ２－ＩＩＩ）、（Ｒ２－ＩＶ）、（Ｒ２－Ｖ）、（Ｒ２－ＶＩ）又は（Ｒ２－ＶＩＩ）の置換基が、式（Ｉ）又は式（ＩＩ）の化合物の残部に結合している結合を表し、
点線
Figure 2020239720000004
 を有する結合はいずれも、互いから独立して、炭素－炭素単結合又は炭素－炭素二重結合のいずれかを表し、
波線はいずれも、炭素－炭素二重結合に連結している場合Ｚ配置又はＥ配置のいずれかである炭素－炭素結合を、互いから独立して表し、
ｎは、１、２、３、４、５又は６を表す
ことを特徴とする、請求項１～５のいずれか一項に記載の方法。 R 2 is represented by formulas (R2-I), (R2-II), (R2-III), (R2-IV), (R2-V), (R2-VI) and (R2-VII)
Figure 2020239720000003
 is selected from the group consisting of
In the formula, the dotted line represents the the substituent represents a bond attached to the remainder of the compound of formula (I) or formula (II);
dotted line
Figure 2020239720000004
 represent, independently of each other, either carbon-carbon single bonds or carbon-carbon double bonds;
any wavy lines independently from each other represent carbon-carbon bonds that are either in the Z configuration or the E configuration when attached to a carbon-carbon double bond;
Method according to any one of the preceding claims, characterized in that n stands for 1, 2, 3, 4, 5 or 6 . 前記添加物が、式（ＩＩＩ）
Figure 2020239720000005
 ［式中、Ｒは、アルキル基又はシクロアルキル基又はアリール基のいずれかであり、点線は、式（ＩＩＩ）の置換基が前記添加物の残部に結合している結合を表す］
のホスフィノ基を２つ以上有することを特徴とする、請求項１～７のいずれか一項に記載の方法。 The additive has the formula (III)
Figure 2020239720000005
 [wherein R is either an alkyl or cycloalkyl or aryl group and the dashed line represents the bond that attaches the substituent of formula (III) to the remainder of said additive]
The method according to any one of claims 1 to 7, characterized in that it has two or more phosphino groups of 前記有機リン化合物が、１，２－ビス（ジフェニルホスフィノ）エタン、１，３－ビス（ジフェニルホスフィノ）プロパン、１，４－ビス（ジフェニルホスフィノ）ブタン、１，３－ビス（ジフェニルホスフィノ）－２－（ジフェニルホスフィノ）メチル－２－メチルプロパン、２，２’－ビス（ジフェニルホスフィノ）－１，１’－ビナフタレン及びビス（２－ジフェニルホスフィノエチル）フェニルホスフィンからなる群から選択されることを特徴とする、請求項１～７のいずれか一項に記載の方法。 The organic phosphorus compound is 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,3-bis(diphenylphosphino) fino)-2-(diphenylphosphino)methyl-2-methylpropane, 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene and bis(2-diphenylphosphinoethyl)phenylphosphine A method according to any one of claims 1 to 7, characterized in that it is selected from 前記水素化が、いずれの有機第四級アンモニウム化合物も使用せずに実行されることを特徴とする、請求項１～９のいずれか一項に記載の方法。 Process according to any one of claims 1 to 9, characterized in that the hydrogenation is carried out without using any organic quaternary ammonium compound. 前記水素化が、いずれの有機溶媒も使用せずに実行されることを特徴とする、請求項１～１０のいずれか一項に記載の方法。 Process according to any one of claims 1 to 10, characterized in that the hydrogenation is carried out without using any organic solvent. 前記担体が、炭素又は無機担体であることを特徴とする、請求項１～１１のいずれか一項に記載の方法。 A method according to any one of claims 1 to 11, characterized in that said support is a carbon or inorganic support . 前記水素化触媒が、コロイド懸濁液の形態であることを特徴とする、請求項１～１２のいずれか一項に記載の方法。 Process according to any one of claims 1 to 12, characterized in that the hydrogenation catalyst is in the form of a colloidal suspension. 前記添加物の、触媒に対する重量比は、０．０１：１～１００：１の範囲であることを特徴とする、請求項１～１３のいずれか一項に記載の方法。 Process according to any one of the preceding claims, characterized in that the weight ratio of said additive to catalyst ranges from 0.01:1 to 100:1. － 式（Ｉ）
Figure 2020239720000006
 ［式中、
Ｒ１は、Ｈ又はメチル基又はエチル基を表し、並びに
Ｒ２は、少なくとも１つの化学官能基を任意選択により含む、飽和又は不飽和の、直鎖若しくは分岐鎖又は環式の、１～４６個のＣ原子を有するヒドロカルビル基を表すか、
又は
Ｒ１及びＲ２は、一緒に５～７員環を形成しているアルキレン基を表すか
のいずれかである］
の化合物、
－ 担体に担持されたパラジウムである水素化触媒、及び
－ ホスフィノ基又はホスフィンオキシド基のいずれかを担持する有機リン化合物である少なくとも１つの添加物
を含む組成物において、
前記添加物がホスフィノ基を担持する場合、前記添加物は２つ以上のホスフィノ基を担持することを特徴とする、組成物。 - Formula (I)
Figure 2020239720000006
 [In the formula,
R 1 represents H or a methyl or ethyl group and R 2 is saturated or unsaturated, linear or branched or cyclic, 1-46, optionally comprising at least one chemical functional group represents a hydrocarbyl group having 1 C atom, or
or R 1 and R 2 together represent an alkylene group forming a 5- to 7-membered ring]
a compound of
- a hydrogenation catalyst which is palladium on a support; and - at least one additive which is an organophosphorus compound carrying either a phosphino group or a phosphine oxide group,
A composition, wherein when the additive carries phosphino groups, the additive carries two or more phosphino groups.
JP2021568559A 2019-05-27 2020-05-26 Selective hydrogenation of alkynols to alkenols in the presence of phosphorus compounds Pending JP2022533821A (en)

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EP19176760 2019-05-27
EP19176760.7 2019-05-27
PCT/EP2020/064496 WO2020239720A1 (en) 2019-05-27 2020-05-26 Selective hydrogenation of alkynols to alkenols in the presence of a phosphorus compound

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JP7452759B2 (en) 2021-07-19 2024-03-19 エルジー・ケム・リミテッド Catalyst for hydrogenation reaction and method for producing the same

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