JP2019527616A - 水/界面活性剤混合物中における化学反応のための触媒 - Google Patents
水/界面活性剤混合物中における化学反応のための触媒 Download PDFInfo
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- JP2019527616A JP2019527616A JP2019500472A JP2019500472A JP2019527616A JP 2019527616 A JP2019527616 A JP 2019527616A JP 2019500472 A JP2019500472 A JP 2019500472A JP 2019500472 A JP2019500472 A JP 2019500472A JP 2019527616 A JP2019527616 A JP 2019527616A
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 98
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Classifications
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- B01J31/18—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
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- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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Abstract
Description
(a)本発明の第1の態様に従う反応混合物を準備するステップと、
(b)化学反応を進行させるステップと、
を含む、方法を提供する。
(a)1種以上の反応体と、触媒と、界面活性剤/水混合物とを含む反応混合物であって、触媒は、1種以上の可溶化基を含むカップリング試薬であるか、または1種以上の可溶化基を含む配位子と錯体形成している金属イオンであり;可溶化基は、C5〜50アルキル基を含むか、または2〜20個の繰り返し単位を有するポリ(アルキレングリコール)基を含む、反応混合物を準備するステップと;
(b)化学反応を進行させるステップと;
を含む、方法を提供する。
本発明は、第1の態様において、1種以上の反応体と、触媒と、界面活性剤/水混合物とを含む反応混合物であって、触媒は、(a)1種以上の可溶化基を含むカップリング試薬;または(b)1種以上の可溶化基を含む配位子と錯体形成している金属イオンであって;可溶化基は、C5〜50アルキル基を含むか、または2〜20個の繰り返し単位を有するポリ(アルキレングリコール)基を含む、反応混合物を提供する。
(式中、
R1は、−N+(R3)3であり;
R2は、それぞれ独立に、C1〜5アルコキシ、C1〜5アルキル、ヒドロキシ、任意選択的に1個もしくは2個のC1〜5アルキルで置換されたアミノまたは−N+(R3)3であり(ここで、C1〜5アルキル基またはC1〜5アルコキシ基は、ヒドロキシ、アミノ、メトキシおよびエトキシから選択される1個もしくは2個の基で任意選択的に置換されており、ならびに/または、1個もしくは2個の炭素原子は任意選択的に酸素、硫黄もしくは窒素に置き換わっている);
R3は、それぞれ独立に、ヒドロキシ、アミノ、メトキシおよびエトキシから選択される1個もしくは2個の基で任意選択的に置換されており、ならびに/または1個もしくは2個の炭素原子は、任意選択的に酸素、硫黄もしくは窒素に置き換わっている、C1〜5アルキルであり、2個のR3基は、任意選択的に、それらが結合している窒素原子と一緒になってC4〜7複素環を形成していてもよく、1個または2個の炭素原子は、任意選択的に、酸素、硫黄または窒素に置き換わっており;
R2および/またはR3の少なくとも1個は可溶化基に置き換わっている)を有する。
(式中
R1、R2およびR3は、互いに独立に、水素であるか、またはヒドロキシ、アミノ、メトキシおよびエトキシから選択される1個もしくは2個の基で任意選択的に置換されており、ならびに/もしくは、1個もしくは2個の炭素原子は任意選択的に酸素、硫黄もしくは窒素に置き換わっている、C1〜5アルキルであり;
R0は、HまたはC1〜5アルキル(特にメチル)またはCH2−Ar(式中、Arは、1、2、3、4または5個のR4で任意選択的に置換されたフェニルまたはベンジルである)であり、ここで、C1〜5アルキル基は、ヒドロキシ、アミノ、メトキシおよびエトキシから選択される1個もしくは2個の基で任意選択的に置換されており、ならびに/または、1個もしくは2個の炭素原子は、任意選択的に、酸素、硫黄もしくは窒素に置き換わっており;
R4は、それぞれ互いに独立に、C1〜5アルコキシ、C1〜5アルキル、2、3もしくは4個の繰り返し単位を有するポリ(エチレングリコール)、2、3もしくは4個の繰り返し単位を有するポリ(プロピレングリコール)、ヒドロキシまたは1個もしくは2個のC1〜5アルキルで任意選択的に置換されたアミノであり、ここでC1〜5アルキル基またはC1〜5アルコキシ基は、ヒドロキシ、ハロゲン、アミノ、メトキシおよびエトキシから選択される1、2もしくは3個の基で任意選択的に置換されており、ならびに/または、1個もしくは2個の炭素原子は、任意選択的に、酸素、硫黄もしくは窒素に置き換わっており、ポリ(エチレングリコール)およびポリ(プロピレングリコール)は、末端酸素がメチル、エチルまたはプロピルで任意選択的に置換されており;
R0、R1、R2およびR4の少なくとも1種、好ましくはR1およびR2の少なくとも1種、特にR1およびR2は両方共、可溶化基に置き換わっている)で表されるビフェニル化合物である。
(式中、
Arは、それぞれ互いに独立に、1、2、3、4または5個のR1で任意選択的に置換されたフェニルであり;
R1は、それぞれ互いに独立に、C1〜5アルコキシ、C1〜5アルキル、2、3もしくは4個の繰り返し単位を有するポリ(エチレングリコール)、2、3もしくは4個の繰り返し単位を有するポリ(プロピレングリコール)、ヒドロキシまたは1個もしくは2個のC1〜5アルキルで任意選択的に置換されたアミノであり、ここでC1〜5アルキル基またはC1〜5アルコキシ基は、ヒドロキシ、アミノ、メトキシおよびエトキシから選択される1個もしくは2個の基で任意選択的に置換されており、ならびに/または、1個もしくは2個の炭素原子は、任意選択的に、酸素、硫黄もしくは窒素に置き換わっており、ポリ(エチレングリコール)およびポリ(プロピレングリコール)は、末端酸素がメチル、エチルまたはプロピルで任意選択的に置換されており;
R1基の少なくとも1個、好ましくは各Ar基の1個のR1は可溶化基に置き換わっている)で表される、N−複素環式カルベン化合物である。
(式中、
R1は、それぞれ互いに独立に、C1〜5アルコキシ、C1〜5アルキル、2、3もしくは4個の繰り返し単位を有するポリ(エチレングリコール)、2、3もしくは4個の繰り返し単位を有するポリ(プロピレングリコール)、ヒドロキシまたは1個もしくは2個のC1〜5アルキルで任意選択的に置換されたアミノであり、ここでC1〜5アルキル基またはC1〜5アルコキシ基は、ヒドロキシ、アミノ、メトキシおよびエトキシから選択される1個もしくは2個の基で任意選択的に置換されており、ならびに/または、1個または2個の炭素原子は、任意選択的に酸素、硫黄もしくは窒素に置き換わっており、ポリ(エチレングリコール)およびポリ(プロピレングリコール)は、末端酸素がメチル、エチルまたはプロピルで任意選択的に置換されており;
R1基の少なくとも1個、好ましくはR1基は両方共可溶化基に置き換わっている)で表される、ビピリジン化合物である。
(a)本明細書に記載する反応混合物を準備するステップと、
(b)化学反応を進行させるステップと、
を含む方法を提供する。
(a)1種以上の反応体と、触媒と、界面活性剤/水混合物とを含む反応混合物であって、触媒は、1種以上の可溶化基を含むカップリング試薬であるか、または1種以上の可溶化基を含む配位子と錯体形成している金属イオンであり;可溶化基は、C5〜50アルキル基を含むか、または2〜20個の繰り返し単位を有するポリ(アルキレングリコール)基を含む、反応混合物を準備するステップと;
(b)化学反応を進行させるステップと;
を含む、方法を提供する。
(a)1種以上の反応体と、触媒と、界面活性剤/水混合物とを含む反応混合物であって、触媒は、1種以上の可溶化基を含むカップリング試薬であるか、または1種以上の可溶化基を含む配位子と錯体形成している金属イオンであり;可溶化基は、C5〜50アルキル基を含むかまたは2〜20個の繰り返し単位を有するポリ(アルキレングリコール)基を含む、反応混合物を準備するステップと;
(b)化学反応を進行させるステップと;
を含む、方法を提供する。
(a)1種以上の可溶化基を含むカップリング試薬;または
(b)1種以上の可溶化基を含む配位子と錯体形成している金属イオン;
である触媒の使用であって、
可溶化基は、C5〜50アルキル基を含むかまたは2〜20個の繰り返し単位を有するポリ(アルキレングリコール)基を含む、使用を提供する。
TPGS−750−M(水中2%、10eqV)中にカルボン酸(1eq)、NaHCO3(1eq)およびアミン(1.1eq)を含む混合物に、トリアジン(1.1eq)を水混和性共溶媒(1eqV)に溶解した溶液を加えた。25℃で掻き混ぜながら反応が完結するまで反応を進行させた(通常2〜5時間)。完結後、生成物を、さらに水を添加することにより析出させるか、または酢酸イソプロピルで抽出し、シリカゲルのショートカラムで濾過することにより所望のアミド生成物を得た。
Claims (23)
- 1種以上の反応体と、触媒と、界面活性剤/水混合物とを含む反応混合物であって、前記触媒は、
(a)1種以上の可溶化基を含むカップリング試薬;または
(b)1種以上の可溶化基を含む配位子と錯体形成している金属イオン;であり、前記可溶化基は、C5〜50アルキル基を含むか、または2〜20個の繰り返し単位を有するポリ(アルキレングリコール)基を含む、反応混合物。 - 前記可溶化基はC5〜50アルキル基を含み、次に示す特徴:
(i)前記アルキル基は直鎖状である;
(ii)前記アルキル基は8〜15個の炭素原子、特に10〜14個の炭素原子、とりわけ12個の炭素原子を含む;
(iii)メトキシ、エトキシ、プロポキシ、ヒドロキシ、任意選択的にメチル、エチルおよび/またはプロピルのうちの1個または2個で置換されたアミノから、特にメトキシ、エトキシまたはヒドロキシから選択される1種以上の基で置換されている;
(iv)12−メトキシドデシルまたはドデシルである;
の1つ以上を有する、請求項1に記載の反応混合物。 - 前記可溶化基は2〜20個の繰り返し単位を有するポリ(アルキレングリコール)基を含み、次に示す特徴:
(i)前記ポリ(アルキレングリコール)基は、ポリ(エチレングリコール)基またはポリ(プロピレングリコール)基、特にポリ(エチレングリコール)基である;
(ii)前記ポリ(アルキレングリコール)基は、3〜8個の繰り返し単位、特に4〜6個の繰り返し単位を有する;
(iii)メチル、エチル、プロピル、メトキシ、エトキシ、プロポキシ、ヒドロキシ、任意選択的にメチル、エチルおよび/またはプロピルのうちの1個または2個で置換されたアミノから、特に、メチル、エチルまたはプロピルから選択される1種以上の基で置換されている;
(iv)末端酸素がメチルまたはエチルで任意選択的に置換されている、4〜6個の繰り返し単位を有するポリ(エチレングリコール)基である;
の1つ以上を有する、請求項1に記載の反応混合物。 - 前記可溶化基は、前記カップリング試薬または配位子の残部に、エーテル結合、アミン結合、エステル結合またはアミド結合を介して結合している、請求項1〜3のいずれか一項に記載の反応混合物。
- 前記カップリング試薬または配位子は、1個または2個の可溶化基を含む、請求項1〜4のいずれか一項に記載の反応混合物。
- 前記触媒は1,3,5−トリアジン誘導体であるカップリング試薬であり、任意選択的に、次に示す特徴:
(i)好ましくは、トリメチルアミノ基またはN−メチル−N−モルホリノ基である、4級アミン、特に、前記トリアジン環の2位に結合した4級アミンを含む;
(ii)前記トリアジン環の4位および/または6位は、メチル、エチル、プロピル、メトキシ、エトキシおよび/またはプロポキシで置換されている;
(iii)前記可溶化基は、前記4級アミンならびに/または前記トリアジン環の4位および/もしくは6位に結合している;
の1つ以上を有する、請求項1〜5のいずれか一項に記載の反応混合物。 - 前記触媒は、ビフェニル化合物、N−複素環式カルベン化合物およびビピリジン化合物からなる群から選択される配位子と錯体形成している金属イオンである、請求項1〜5のいずれか一項に記載の反応混合物。
- 前記触媒の前記金属イオンは、銅イオン、ルテニウムイオン、ロジウムイオン、パラジウムイオン、ニッケルイオン、亜鉛イオン、金イオン、マンガンイオン、鉄イオンおよびコバルトイオンからなる群から選択される、請求項1〜7のいずれか一項に記載の反応混合物。
- 前記界面活性剤は、親水性部分および疎水性部分を含む非イオン性界面活性剤であり、好ましくは、前記界面活性剤の前記親水性部分はポリエチレングリコール部分を含む、請求項1〜8のいずれか一項に記載の反応混合物。
- 前記界面活性剤は、(DL−α−)トコフェロールポリエチレングリコールコハク酸エステル(TPGS)(TPGS−750−M、TPGS−1000、TPGS−1500等);TritonX−100、ポリエチレングリコールアルキルエーテル(Brij等)、ポリエチレングリコールエステル(ヒドロキシステアリン酸ポリエチレングリコール(15)(SolutolHS15)等)、Tween(Tween 20、Tween 80等)、ドデシル硫酸ナトリウム(SDS)、臭化セチルトリメチルアンモニウム(CTAB)、相間移動界面活性剤(PTS)(例えば、デオキシコール酸ナトリウム)、ポリオキシエタニルユビキノールセバケート(PQS)および修飾PQS、ポリエチレングリコール(PEG)および様々な誘導体(C4−azo−PEG等)、オクタン酸および他の長鎖アルキル酸ならびにb−シトステロールメトキシエチレングリコールコハク酸エステル(Nok)からなる群から選択される、請求項1〜9のいずれか一項に記載の反応混合物。
- 前記界面活性剤/水混合物中の前記界面活性剤の濃度は0.5〜5%(w/w)である、請求項1〜10のいずれか一項に記載の反応混合物。
- 前記反応混合物は、1種の反応体または2種の反応体を含む、請求項1〜11のいずれか一項に記載の反応混合物。
- 有機溶媒をさらに含む、請求項1〜12のいずれか一項に記載の反応混合物。
- 前記反応混合物は均一な混合物である、請求項1〜13のいずれか一項に記載の反応混合物。
- 前記反応混合物はコロイド懸濁液である、請求項1〜14のいずれか一項に記載の反応混合物。
- 化学反応を実施する方法であって、
(a)請求項1〜15のいずれか一項に記載の反応混合物を準備するステップと、
(b)前記化学反応を進行させるステップと、
を含む方法。 - 前記化学反応の生成物を単離するステップをさらに含む、請求項16に記載の方法。
- 前記反応混合物は、前記化学反応全体を通して均一な混合物である、請求項16または17に記載の方法。
- 前記反応混合物は前記化学反応全体を通してコロイド懸濁液である、請求項16〜18のいずれか一項に記載の方法。
- 界面活性剤/水混合物中で実施される化学反応の収率を向上する方法であって、
(a)1種以上の反応体と、触媒と、界面活性剤/水混合物とを含む反応混合物を準備するステップであって、前記触媒は、1種以上の可溶化基を含むカップリング試薬であるか、または1種以上の可溶化基を含む配位子と錯体形成している金属イオンであり;前記可溶化基は、C5〜50アルキル基を含むか、または2〜20個の繰り返し単位を有するポリ(アルキレングリコール)基を含む、ステップと;
(b)前記化学反応を進行させるステップと;
を含む、方法。 - 界面活性剤/水混合物中で実施される化学反応において生成する副生成物の量を低減する方法であって、
(a)1種以上の反応体と、触媒と、界面活性剤/水混合物とを含む反応混合物を準備するステップであって、前記触媒は、1種以上の可溶化基を含むカップリング試薬であるか、または1種以上の可溶化基を含む配位子と錯体形成している金属イオンであり;前記可溶化基は、C5〜50アルキル基を含むか、または2〜20個の繰り返し単位を有するポリ(アルキレングリコール)基を含む、ステップと;
(b)前記化学反応を進行させるステップと;
を含む、方法。 - 前記反応混合物は請求項1〜15のいずれか一項に記載の反応混合物である、請求項20または21に記載の方法。
- 請求項16〜19のいずれか一項に記載の化学反応を実施する方法を含む、請求項20または21に記載の方法。
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