GB888162A - Preparation of ª--ª-, ª--ª+-unsaturated carboxylic derivatives - Google Patents

Preparation of ª--ª-, ª--ª+-unsaturated carboxylic derivatives

Info

Publication number
GB888162A
GB888162A GB3221458A GB3221458A GB888162A GB 888162 A GB888162 A GB 888162A GB 3221458 A GB3221458 A GB 3221458A GB 3221458 A GB3221458 A GB 3221458A GB 888162 A GB888162 A GB 888162A
Authority
GB
United Kingdom
Prior art keywords
methyl
dimethyl
acid
heptadienoic
heptadienoate
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB3221458A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Montedison SpA
Original Assignee
Montedison SpA
Montecatini Societa Generale per lIndustria Mineraria e Chimica SpA
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 Montedison SpA, Montecatini Societa Generale per lIndustria Mineraria e Chimica SpA filed Critical Montedison SpA
Publication of GB888162A publication Critical patent/GB888162A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
    • C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

The invention comprises a -b ,d -e -unsaturated carboxylic derivatives of formula <FORM:0888162/IV (b)/1> where n is 1 or 2, n1 is 0 or 1, R is H or a C1-20 unsubstituted or substituted aliphatic group and R1 is H or C1-20 aliphatic, hydroxyaliphatic, arylaliphatic or cycloaliphatic group; except that 2,5-heptadienoic and 2,5-octadienoic acids in which the double bond conjugated with the carboxyl group is in the trans-configuration are excluded. They are prepared by reacting an allyl derivative R-[(CH2)n1-CH=CH-CH2Cl]n and acetylene with a solution of nickel carbonyl in R1OH. Temperatures of 0 DEG C.-75 DEG C., generally 25 DEG C.-60 DEG C. may be used. Carbon monoxide may be introduced to renew nickel carbonyl reacted so that it is not necessary to supply stoichiometric amounts of nickel carbonyl. Buffers (e.g. MgCO3, CaCO3, NaH2PO4) or solvents (e.g. acetone, glycol ethers, diethylketone) may be used. Continuous operation with recycling of gases is possible. Preferably excess acetylene is used. The products have the double bond conjugated with the carboxyl group predominantly in the cis-configuration and can be converted to the trans-isomer by heating to about 250 DEG C. The products are stated to be useful as plasticisers. Specific compounds claimed are: 2,5-hexadienoic acid and its methyl, ethyl, isopropyl, benzyl and ethylene glycol esters; 2,5-heptadienoic acid with the double bond conjugated with the carboxyl group in the cisconfiguration; methyl 2,5-heptadienoate; methyl 7 - acetoxy - 2,5 - heptadienoate, 7 - cyano - 2,5 heptadienoic acid and its methyl, isopropyl and cyclohexyl esters; dimethyl 2,5-octadiendioate; and dimethyl tetradeca-2,5,9,12-tetraendioate. Caproic acid, methyl caproate, heptanoic acid, methyl heptanoate, dimethyl suberate and dimethyl tetradecandioate are prepared by catalytic hydrogenation of hexadienoic acid, methyl hexadienoate, heptadienoic acid, methyl heptadienoate, dimethyl octadiendioate and dimethyl tetradecatetraendioate respectively.
GB3221458A 1957-10-10 1958-10-09 Preparation of ª--ª-, ª--ª+-unsaturated carboxylic derivatives Expired GB888162A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IT1448657 1957-10-10
IT16458 1958-01-08
IT641758 1958-04-24

Publications (1)

Publication Number Publication Date
GB888162A true GB888162A (en) 1962-01-24

Family

ID=27272476

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3221458A Expired GB888162A (en) 1957-10-10 1958-10-09 Preparation of ª--ª-, ª--ª+-unsaturated carboxylic derivatives

Country Status (3)

Country Link
CH (2) CH366554A (en)
DE (1) DE1133720B (en)
GB (1) GB888162A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6015821A (en) * 1995-05-01 2000-01-18 Horrobin; David Frederick Nicotinic acid esters and pharmaceutical compositions containing them
US6555700B1 (en) 1995-05-01 2003-04-29 Scotia Holdings Plc 1,3-propane diol esters and ethers and methods for their use in drug delivery
USRE40546E1 (en) * 1996-05-01 2008-10-21 Scarista, Ltd. 1,3-Propane diol esters and ethers and methods for their use in drug delivery

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT164026B (en) * 1947-02-21 1949-09-26 Ciba Geigy Process for the preparation of esters of olefin carboxylic acids
DE805641C (en) * 1948-10-02 1951-05-25 Basf Ag Process for the production of ª ‡, ª ‰ -unsaturated carboxylic acids and their derivatives
US2582911A (en) * 1950-07-12 1952-01-15 Rohm & Haas Preparation of acrylic esters
US2613222A (en) * 1951-04-06 1952-10-07 Rohm & Haas Preparation of acrylic acid and its anhydride
DE895767C (en) * 1951-09-04 1953-11-05 Basf Ag Process for the production of ª ‡, ª ‰ -unsaturated carboxylic acids or their decoctions
US2778848A (en) * 1953-01-21 1957-01-22 Rohm & Haas Preparation of acrylates
DE1005954B (en) * 1954-10-27 1957-04-11 Basf Ag Process for the production of polyene carboxylic acid esters or nitriles

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6015821A (en) * 1995-05-01 2000-01-18 Horrobin; David Frederick Nicotinic acid esters and pharmaceutical compositions containing them
US6555700B1 (en) 1995-05-01 2003-04-29 Scotia Holdings Plc 1,3-propane diol esters and ethers and methods for their use in drug delivery
USRE40480E1 (en) * 1995-05-01 2008-09-02 Scarista Limited 1,3-Propane diol esters and ethers and methods for their use in drug delivery
USRE43632E1 (en) * 1995-05-01 2012-09-04 Scarista, Ltd. 1,3-propane diol esters and ethers and methods for their use in drug delivery
USRE40546E1 (en) * 1996-05-01 2008-10-21 Scarista, Ltd. 1,3-Propane diol esters and ethers and methods for their use in drug delivery

Also Published As

Publication number Publication date
CH366554A (en) 1963-01-15
DE1133720B (en) 1962-07-26
CH389587A (en) 1965-03-31

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