KR890009827A - 알릴형 아민의 제조방법 - Google Patents

알릴형 아민의 제조방법 Download PDF

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KR890009827A
KR890009827A KR1019880016446A KR880016446A KR890009827A KR 890009827 A KR890009827 A KR 890009827A KR 1019880016446 A KR1019880016446 A KR 1019880016446A KR 880016446 A KR880016446 A KR 880016446A KR 890009827 A KR890009827 A KR 890009827A
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allyl
compound
amine
producing
hydrocarbon group
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KR1019880016446A
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이시무라 유시마사
오에 다까미
스야마 유세끼
나가또 노부유끼
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무라다 가쓰
소와 덴꼬 가부시끼 가이샤
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Priority claimed from JP62312339A external-priority patent/JPH0759535B2/ja
Priority claimed from JP62323833A external-priority patent/JPH0757743B2/ja
Application filed by 무라다 가쓰, 소와 덴꼬 가부시끼 가이샤 filed Critical 무라다 가쓰
Publication of KR890009827A publication Critical patent/KR890009827A/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
    • C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
    • C07C33/03—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond in beta-position, e.g. allyl alcohol, methallyl alcohol
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • 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
    • B01J31/1845—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 phosphorus
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • 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
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • 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
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • B01J31/2414—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
    • B01J2231/4283—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using N nucleophiles, e.g. Buchwald-Hartwig amination
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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Abstract

내용 없음

Description

알릴형 아민의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (13)

  1. 팔라듐 화합물 및 여러자리 배위자 인 화합물의 존재하에서 다음의 일반식으로 나타내는 알릴형 알코올과 암모니아, 1차아민 및 2차아민 중에서 선택한 적어도 한가지를 반응시키는 것으로 이루어지는 알릴형 아민의 제조방법.
    상기식중 R1, R2및 R3는 독립적으로 수소원자, 탄소원자를 1-8개 갖는 지환족 탄화수소기 또는 지방족 탄화수소기, 또는 방향족 탄화수소기를 나타냄.
  2. 제 1 항에 있어서, 알릴형 알코올이 알릴 알코올인 것이 특징인 알릴형 아민의 제조방법.
  3. 제 1 항에 있어서, 1차아민이 모노알릴아민 것이 특징인 알릴형 아민의 제조방법.
  4. 제 1 항에 있어서, 2차아민이 디알릴아민과 디메틸아민 중에서 선택되는 것이 특징인 알릴형 아민의 제조방법.
  5. 제 1 항에 있어서, 반응을 알칼리 존재하에서 수행하고 알칼리는 팔라듐 화합물의 팔라듐 금속에 대한 몰비가 1-200의 양으로 첨가하는 것이 특징인 알릴형 아민의 제조방법.
  6. 제 5 항에 있어서, 알칼리가 수산화 테트라메틸암모늄과 수산화 3차 부틸암모늄 중에서 선택되는 것이 특징인 알릴형 아민의 제조방법.
  7. 제 1 항에 있어서, 여러자기 배위자 인 화합물을 팔라듐 화합물의 팔라듐 금속에 대한 몰비가 1-20이 되는 양으로 첨가하는 것이 특징인 알릴형 아민의 제조방법.
  8. 제 1 항에 있어서, 암모니아나 아민을 알릴형 알코올에 대한 몰비가 1-5가 되는 양를 첨가하고 반을을 60oC-150oC에서 수행하는 것이 특징인 알릴형 아민의 제조방법.
  9. 제 1 항에 있어서, 반응을 용매 존재하에서 수행하고 이 용매는 프로필렌 글리콜 및 1,4-부탄디올 중에서 선택하는 것이 특징인 알릴형 아민의 제조방법.
  10. 제 1 항에 있어서, 여러자리 배위자 인 화합물이 다음 일반식으로 나타내는 두자리 배위자 인 화합물인 것이 특징인 알릴형 아민의 제조방법.
    상기식중 R4, R5및 R7및 R8은 탄소원자를 1-20개 갖는 지방족 탄화수소 방향족 탄화수소 또는 지환족 탄화수소이고, R6은 탄소원자를 3 또는 4개 갖는 2가 탄화수소기를 나타냄.
    제10항에 있어서, 두자리 배위자 인 화합물이 1,4-비스-(디페닐-포스피노)-부탄 및 1,3-비스-(디페닐-포스피노)-프로판중에서 선택되는 것이 특징인 알릴형 아민의 제조방법.
  11. 다음의 일반식으로 나타내는 알릴형 알코올을 암모니아, 1차아민 및 2차아민중에서 선택한 적어도 한 가지와 반응시킴으로써 알릴형 아민을 제조하는데 이용되고, 팔라듐 화합물 및 여러자리 배위자 인 화합물로 이루어짐을 특징으로 하는 촉매 :
    상기식중, R1, R2및 R3은 독립적으로 수소원자, 탄소원자를 1-8개를 갖는 지환족 탄화수소 또는 지방족 탄화수소기, 또는 방향족 탄화수소기를 나타냄.
  12. 제12항에 있어서, 여러자리 배위자 인 화합물이 다음의 일반식으로 나타내는 두자리 배위자 인 화합물인 것이 특징인 촉매 :
    상기식중, R4, R5, R7및 R8은 탄소원자를 1-20개 갖는 지방족 탄화수소기, 방향족 탄화수소기 또는 지환족 탄화수소기이고, R6은 탄소원자를 3개 또는 4개 갖는 2가 탄화수소기를 나타냄.
  13. 제13항에 있어서, 두자리 배위자 인 화합물이 1,4-비스-(디페닐-포스피스)-부탄 및 1,3-(디페닐-포스피스)-프로판 중에서 선태되는 것이 특징인 촉매.
    ※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880016446A 1987-12-11 1988-12-10 알릴형 아민의 제조방법 KR890009827A (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP62312339A JPH0759535B2 (ja) 1987-12-11 1987-12-11 アリル型アミンの製造法
JP62-312339 1987-12-11
JP62323833A JPH0757743B2 (ja) 1987-12-23 1987-12-23 アリル型アミンの製造法
JP62-323833 1987-12-23

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KR890009827A true KR890009827A (ko) 1989-08-04

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US (1) US4942261A (ko)
EP (1) EP0320269B1 (ko)
KR (1) KR890009827A (ko)
DE (1) DE3883724T2 (ko)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5208380A (en) * 1989-12-22 1993-05-04 Koei Chemical Co., Ltd. Process for preparing monoallylamine
DE69008829T2 (de) * 1989-12-22 1994-11-24 Koei Chemical Co Verfahren zur Herstellung von Monoallylamin.
US5229343A (en) * 1990-04-27 1993-07-20 Shell Oil Company Polymerization process
US5171832A (en) * 1990-04-27 1992-12-15 Shell Oil Company Polymerization of carbon monoxide/olefin with p bidentate ligand having (1) alkoxy phenyl p group and (2) monosubstituted divalent bridging group
JP5808437B2 (ja) 2011-03-08 2015-11-10 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 均一系触媒作用を利用したアルコール・アミノ化によってジ−、トリ−およびポリアミンを製造する方法
AU2012224718A1 (en) * 2011-03-08 2013-09-19 Basf Se Method for producing primary amines obtained by homogeneously catalyzed alcohol amination
US8785693B2 (en) 2011-03-08 2014-07-22 Basf Se Process for the preparation of primary amines by homogeneously catalyzed alcohol amination
US8912361B2 (en) 2011-03-08 2014-12-16 Basf Se Process for preparing di-, tri- and polyamines by homogeneously catalyzed alcohol amination
CN103086894B (zh) * 2013-02-25 2014-10-01 武汉迪可表面技术有限公司 一种电镀添加剂3-甲基-3-氨基丁炔的合成方法
WO2015054828A1 (en) * 2013-10-15 2015-04-23 Rhodia Operations Process for forming primary, secondary or tertiary amine via direct amination reaction
KR20170083085A (ko) * 2014-11-10 2017-07-17 로디아 오퍼레이션스 직접 아민화 반응에 의한 아민을 형성하는 방법

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* Cited by examiner, † Cited by third party
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US4120901A (en) * 1977-08-31 1978-10-17 Monsanto Company Production of primary and secondary amines by reaction of ammonia with conjugated diene in the presence of Pd/phosphine catalyst and primary or secondary aliphatic alcohol solvent medium
US4417074A (en) * 1981-10-22 1983-11-22 Air Products And Chemicals, Inc. Allylamines from allyl alcohol
JPS632958A (ja) * 1986-06-20 1988-01-07 Showa Denko Kk アリル型アミンの製造法
US4693875A (en) * 1986-08-27 1987-09-15 Battelle Memorial Institute Process for recovery of hydrogen and abstraction of sulfur

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DE3883724D1 (de) 1993-10-07
US4942261A (en) 1990-07-17
EP0320269A3 (en) 1990-09-26
DE3883724T2 (de) 1994-04-28
EP0320269B1 (en) 1993-09-01
EP0320269A2 (en) 1989-06-14

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