KR920007694A - 방향족 디아민의 알킬화 방법 - Google Patents

방향족 디아민의 알킬화 방법 Download PDF

Info

Publication number
KR920007694A
KR920007694A KR1019910018686A KR910018686A KR920007694A KR 920007694 A KR920007694 A KR 920007694A KR 1019910018686 A KR1019910018686 A KR 1019910018686A KR 910018686 A KR910018686 A KR 910018686A KR 920007694 A KR920007694 A KR 920007694A
Authority
KR
South Korea
Prior art keywords
chloride ion
triethylaluminum
ion source
catalyst
diamine
Prior art date
Application number
KR1019910018686A
Other languages
English (en)
Other versions
KR100199120B1 (ko
Inventor
죠오지 이르만 크린
웨인 미첼 올란
제이알. 릴레이 우드로우 윌슨
Original Assignee
필립 맥키니 피펜저
에틸 코오포레이션
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 필립 맥키니 피펜저, 에틸 코오포레이션 filed Critical 필립 맥키니 피펜저
Publication of KR920007694A publication Critical patent/KR920007694A/ko
Application granted granted Critical
Publication of KR100199120B1 publication Critical patent/KR100199120B1/ko

Links

Classifications

    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
    • 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
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type

Landscapes

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

Abstract

내용 없음

Description

방향족 디아민의 알킬화 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 트리에틸알루미늄을 방향족 디아민 및 클로라이드 이온원과 반응시키는데 있어서 클로라이드 이온원에 대한 트리에틸아룰미늄의 몰비 1.0:0.9 ~ 0.9:0.01 로 반응시킴으로써 형성된 촉매.
  2. 제1항에 있어서, 클로라이드 이온원에 대한 트리에틸알루미늄의 몰비가 1.0:0.5인 촉매.
  3. 방향족 디아민과 올레핀과의 혼합물을, 클로라이드 이온원에 대한 트리에틸알루미늄의 몰비 0.9:0.01 ~ 1.0:0.5, 바람직하게는 1.0:0.5로 트리에틸알루미늄 및 클로라이드 이온원을 함유하는 촉매로 처리함을 특징으로 하는, 방향족 디아민의 알킬화 및 중말단 형성의 저해 방법.
  4. 제3항에 있어서, 400psi 이상의 압력하에 수행되는 방법.
  5. 제4항에 있어서, 700 ~ 약 5000psi의 압력하에 250~350℃ 온도에서 수행되는 방법.
  6. 제5항에 있어서, 900 ~ 1100psi의 압력하에 280~320℃ 온도에서 수행되는 방법.
  7. 제3항 내지 제6항중 어느 한 항에 있어서, 방향족 디아민이 하기식의 C1~C8직쇄 또는 측쇄 알틸 치환 디아민이고, 올레핀이 프로필렌, 이소부틸렌 또는 에틸렌인 방법.
    [상기식중, X 및 X′는 동일하거나 상이하며, 탄소수 1~6의 직쇄 또는 측쇄 알킬기이고, n는 0 또는 1의 정수이며, 방향족 고리는 각각 아미노기에 대한 오르토 위치에 2개 치환 가능한 수소원자를 함유한다]
  8. 제7항에 있어서, 알킬기가 메틸 또는 에틸인 방법.
  9. 제3항 내지 제8항중 어느 한 항에 있어서, 반응이 용매 부재하에 수행되는 방법.
  10. 촉매내에서 클로라이드 이온원에 대한 트리에틸알루미늄의 비를 1.0:0.5로하여 클로라이드 이온원 존재하에 크리에틸알루미늄을 톨루엔 디아민과 반응시킴으로써 형성된 촉매로, 280 ~ 320℃에서 900~1100psi 압력하에 톨루엔디아민과 에틸렌과의 혼합물을 처리함을 특징으로 하는, 틀루엔 디아민의 알킬화 및 중말단 형성의 저해 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
KR1019910018686A 1990-10-23 1991-10-23 방향족 디아민의 알킬화 방법 KR100199120B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US601,516 1990-10-23
US07/601,516 US5103059A (en) 1990-10-23 1990-10-23 Process for alkylation of aromatic diamines

Publications (2)

Publication Number Publication Date
KR920007694A true KR920007694A (ko) 1992-05-27
KR100199120B1 KR100199120B1 (ko) 1999-06-15

Family

ID=24407782

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019910018686A KR100199120B1 (ko) 1990-10-23 1991-10-23 방향족 디아민의 알킬화 방법

Country Status (5)

Country Link
US (1) US5103059A (ko)
EP (1) EP0482499B1 (ko)
JP (1) JP3413604B2 (ko)
KR (1) KR100199120B1 (ko)
DE (1) DE69110832T2 (ko)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5510561A (en) * 1992-12-21 1996-04-23 Kerr-Mcgee Chemical Corporation Homogenous catalyst and processes for fluid phase alkylation
US7361788B2 (en) * 2006-01-24 2008-04-22 Chemtura Corporation Direct alkylation of N-alkyl-N′-phenyl-p-phenylenediamine
CN107999089B (zh) * 2017-11-28 2021-02-02 万华化学集团股份有限公司 用于生产二乙基甲苯二胺的催化剂及其制备方法、应用
CN108383732A (zh) * 2018-03-27 2018-08-10 双阳化工淮安有限公司 一种二乙基甲苯二胺的制备方法
CN115925556A (zh) * 2022-11-08 2023-04-07 万华化学集团股份有限公司 一种二乙基甲苯二胺的制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2814646A (en) * 1954-04-29 1957-11-26 Ethyl Corp Amine alkylation using aluminum anilide catalyst
US3275690A (en) * 1955-07-14 1966-09-27 Bayer Ag Process for the production of aromatic amines which are alkylated on the nucleus
US3923892A (en) * 1970-12-28 1975-12-02 Ethyl Corp Aromatic amine alkylation
GB1462254A (en) * 1973-06-04 1977-01-19 Ethyl Corp Alkylation of aromatic amines
US4128582A (en) * 1973-06-04 1978-12-05 Ethyl Corporation Chemical process
US4219503A (en) * 1979-08-06 1980-08-26 Ethyl Corporation Process for producing 2,6-dialkylanilines
US4967001A (en) * 1988-06-30 1990-10-30 Air Products And Chemicals, Inc. Alkylation of toluenediamine and para-phenylenediamine with isobutylene in the presence of acidic, crystalline molecular sieves
US5057625A (en) * 1990-02-20 1991-10-15 Ethyl Corporation Selective alkylation process

Also Published As

Publication number Publication date
KR100199120B1 (ko) 1999-06-15
JPH04288042A (ja) 1992-10-13
JP3413604B2 (ja) 2003-06-03
DE69110832D1 (de) 1995-08-03
EP0482499A2 (en) 1992-04-29
DE69110832T2 (de) 1995-11-16
EP0482499B1 (en) 1995-06-28
EP0482499A3 (en) 1993-05-12
US5103059A (en) 1992-04-07

Similar Documents

Publication Publication Date Title
KR900006370A (ko) 유기 염화 알루미늄 촉매작용된 개선된 폴리-n-부텐의 제조방법
KR880012652A (ko) 올레핀 중합용 하프늄 메탈로센 촉매계
KR870008819A (ko) 올레핀의 삼량체화 방법
KR940019666A (ko) α-올레핀 올리고머 및 α-올레핀 올리고머 조성물의 제조방법
KR960014133A (ko) 유기-알루미녹시 생성물 제조 방법
KR950701940A (ko) 1-올레핀 (공)중합용 지지촉매(supported catalyst for 1-olefin(s) (co)polymerization)
EP0812854A3 (en) Novel transition metal compound, olefin polymerization catalyst comprising said compound, process for olefin polymerization using said catalyst and propylene homo- and copolymer
KR900018159A (ko) 올레핀 중합체의 제조방법
PT91916A (pt) Processo de sintese de polimeros a base de boro e de azoto precursores de nitreto de boro
KR960706508A (ko) 촉매 조성물(catalyst compositon)
KR920018086A (ko) 방향족비닐 화합물 중합용 촉매 및 방향족비닐 화합물 중합체의 제조방법
KR920007694A (ko) 방향족 디아민의 알킬화 방법
KR900004771A (ko) 에틸렌 중합 반응 촉매
KR900007888A (ko) 폴리부텐의 개선된 제조방법
US3678113A (en) Nuclearly alkylated aniline recovery process
KR880001684A (ko) 수소화갈륨-드리알킬아민 부가물, 및 iii-v 화합물 필름의 사용방법
KR890013067A (ko) 선상 α-올레핀의 제조방법
KR950000747A (ko) 에틸렌/프로필렌 공중합체 고무
KR900012938A (ko) 알루미녹산의 제조방법
KR890015995A (ko) 프로판아민 유도체
US3784623A (en) Inhibition of olefin isomerization in displacement reactions
KR960037705A (ko) 치환된 아실화제
WO1999052631A1 (en) CATALYST SYSTEM FOR α-OLEFIN OLIGOMERIZATION
KR960004304A (ko) 올레핀의 접촉수화방법
ES2023969B3 (es) Procedimiento para la produccion de polietileno con una distribucion de peso molecular.

Legal Events

Date Code Title Description
N231 Notification of change of applicant
A201 Request for examination
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20090303

Year of fee payment: 11

LAPS Lapse due to unpaid annual fee