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IL40830A - The preparation of 1,4 dicyanobutenes - Google Patents

The preparation of 1,4 dicyanobutenes

Info

Publication number
IL40830A
IL40830A IL40830A IL4083072A IL40830A IL 40830 A IL40830 A IL 40830A IL 40830 A IL40830 A IL 40830A IL 4083072 A IL4083072 A IL 4083072A IL 40830 A IL40830 A IL 40830A
Authority
IL
Israel
Prior art keywords
tricyanobutane
basic catalyst
amine
dicyanobutene
reaction
Prior art date
Application number
IL40830A
Other versions
IL40830A0 (en
Original Assignee
Halcon International Inc
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 Halcon International Inc filed Critical Halcon International Inc
Publication of IL40830A0 publication Critical patent/IL40830A0/en
Publication of IL40830A publication Critical patent/IL40830A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00Preparation of carboxylic acid nitriles
    • C07C253/30Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00Preparation of carboxylic acid nitriles
    • C07C253/08Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
    • C07C253/10Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

Claims (2)

  1. CLAIMS 1. A method of preparing, a 1, 4-dicyanobutene characterized by dehydrocyanating 1, 2 , 4-tricyanobutane .
  2. 2. A method of preparing a 1 , 4-dicyanobutene characterized by: . a) reacting 2-methylene glutaronitrile with' hydrogen cyanide to form 1 , 2 * 4-tricyanobutane; and b) dehydrocyanating said 1 , 2 , -tricyanobutane to form a 1, 4-dicyanobutene. ·' . 3.' A method according to either of claims 1 and 2 characterized in that the 1, 2 , 4-tricyanobutane is dehydrocyanated at a temperature in the range of 100 to 1000°C . in the presence of a basic catalyst. 4. · . A method according to any one of claims 1 , to 3 , 1 characterized in that 1 , 2 , 4-tricyanobutane is prepared by reacting 2-methyl-ene glutaronitrile with hydrogen cyanide in. the liquid phase at temperatures of 0 to 300°C . and in the presence of a basic catalyst. · . Ί 5. A method according to claim 4 characterized in that the reaction ■ ■ i ■ , ' is carried out at temperatures ranging from 40 to 150e C . j j ' 6. . A method according to either of claims 4 and 5 characterized in ; that the reaction is canied out at temperatures ranging from 50- to 125°C . I ■ ■ ■' _!_ . ■ ' 7. A method according to any one of claims4 o 6 wherein the basic catalyst for the reaction of 2-methylene glutaronitrile is a phosphine or an amine or a compound of the alkali metals; the a lkaline earth rnetals; a ! - 32 - 105 OA 40830/2 lanthanide series; indium; thallium or lead. ; 14. · A methpd according to any one of claims'3 to 12 characterized in that basic catalyst is a heterocyclic amine , an aryl amine , an alkyl amine , a cycloalkyl amine', an arsine, a stibine, or a quaternary ammonium or phosphonium hydroxide. 15.. A method according to claim 13 characterized in that the dehydrocya nation of 1, 2 , 4-tricyanobutane is c irried out in the liquid phase and in the presence of a lithium compound catalyst. I 16. A method according to claim 13.characterized in that the basic catalyst is a trialkyl or cycloalkyl phosphine. i 17. A process according to any one of Claims 2 to; 16 characterized in that the 2-methylene glutaronitrile is prepared by dimerization of acrylonitrile. For the Applicants · DR. KEI HOL COHN AND PARTNERS B j I Λ ■
IL40830A 1971-11-15 1972-11-14 The preparation of 1,4 dicyanobutenes IL40830A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US19898771A 1971-11-15 1971-11-15
US28527272A 1972-08-31 1972-08-31
US28527172A 1972-08-31 1972-08-31
US28678472A 1972-09-06 1972-09-06
US29811572A 1972-10-16 1972-10-16

Publications (2)

Publication Number Publication Date
IL40830A0 IL40830A0 (en) 1973-01-30
IL40830A true IL40830A (en) 1976-01-30

Family

ID=27539397

Family Applications (3)

Application Number Title Priority Date Filing Date
IL48000A IL48000A (en) 1971-11-15 1972-11-14 The preparation of 1,4-dicyanobutenes
IL40830A IL40830A (en) 1971-11-15 1972-11-14 The preparation of 1,4 dicyanobutenes
IL48000A IL48000A0 (en) 1971-11-15 1975-08-27 The preparation of 1,4-dicyanobutenes

Family Applications Before (1)

Application Number Title Priority Date Filing Date
IL48000A IL48000A (en) 1971-11-15 1972-11-14 The preparation of 1,4-dicyanobutenes

Family Applications After (1)

Application Number Title Priority Date Filing Date
IL48000A IL48000A0 (en) 1971-11-15 1975-08-27 The preparation of 1,4-dicyanobutenes

Country Status (18)

Country Link
JP (1) JPS4861423A (en)
AR (2) AR199886A1 (en)
AU (1) AU471821B2 (en)
BE (1) BE791339A (en)
CA (1) CA1001657A (en)
CH (2) CH553165A (en)
DD (2) DD109863A5 (en)
DE (3) DE2265299C3 (en)
DK (3) DK132320C (en)
EG (1) EG10867A (en)
FR (1) FR2161597A5 (en)
IE (1) IE37078B1 (en)
IL (3) IL48000A (en)
IT (1) IT986887B (en)
NL (2) NL162633C (en)
NO (1) NO137938C (en)
RO (2) RO72552A (en)
SE (1) SE405353B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080374A (en) * 1977-02-23 1978-03-21 E. I. Du Pont De Nemours And Company Product recovery

Also Published As

Publication number Publication date
DD109863A5 (en) 1974-11-20
IE37078B1 (en) 1977-04-27
RO72552A (en) 1982-02-26
DE2265299A1 (en) 1977-04-14
DE2256039B2 (en) 1980-01-24
CA1001657A (en) 1976-12-14
DD106367A5 (en) 1974-06-12
IT986887B (en) 1975-01-30
NL162633C (en) 1980-06-16
CH551951A (en) 1974-07-31
EG10867A (en) 1976-08-31
AR199886A1 (en) 1974-10-08
DE2265299B2 (en) 1980-04-24
JPS4861423A (en) 1973-08-28
NO137938B (en) 1978-02-13
NL7907083A (en) 1980-02-29
IL48000A (en) 1976-01-30
SE405353B (en) 1978-12-04
NO137938C (en) 1978-05-31
RO72799A (en) 1981-11-04
AR198539A1 (en) 1974-06-28
DK132320B (en) 1975-11-24
DE2265299C3 (en) 1981-01-08
DK589974A (en) 1975-06-02
IL48000A0 (en) 1975-11-25
NL162633B (en) 1980-01-15
DK132320C (en) 1976-05-03
IL40830A0 (en) 1973-01-30
DE2264932A1 (en) 1975-06-26
DE2256039A1 (en) 1973-05-17
CH553165A (en) 1974-08-30
DE2256039C3 (en) 1981-02-19
SE7505822L (en) 1975-05-22
AU471821B2 (en) 1976-05-06
DE2264932B2 (en) 1977-08-18
IE37078L (en) 1973-05-15
FR2161597A5 (en) 1973-07-06
DK590074A (en) 1975-06-02
DE2264932C3 (en) 1978-04-06
NL7215387A (en) 1973-05-17
BE791339A (en) 1973-05-14
AU4883372A (en) 1974-05-16

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