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GB893268A - Metal salts of 2-carboxy-3-metallo-propenes - Google Patents

Metal salts of 2-carboxy-3-metallo-propenes

Info

Publication number
GB893268A
GB893268A GB40568/59A GB4056859A GB893268A GB 893268 A GB893268 A GB 893268A GB 40568/59 A GB40568/59 A GB 40568/59A GB 4056859 A GB4056859 A GB 4056859A GB 893268 A GB893268 A GB 893268A
Authority
GB
United Kingdom
Prior art keywords
carboxy
metal
compounds
metallo
propene
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
GB40568/59A
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.)
Ethyl Corp
Original Assignee
Ethyl Corp
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
Priority claimed from US846819A external-priority patent/US3108134A/en
Application filed by Ethyl Corp filed Critical Ethyl Corp
Publication of GB893268A publication Critical patent/GB893268A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/14—Monocyclic dicarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C07C57/08—Crotonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
    • C07C57/48—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/02—Magnesium compounds

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)
  • Enzymes And Modification Thereof (AREA)

Abstract

893,268. Metal salts of 2-carboxy-3-metallopropenes. ETHYL CORPORATION. Nov. 30, 1959 [Dec. 2, 1958], No. 40568/59. Class 2 (3). The invention comprises a metal salt of 2- carboxy-3-metallo-propene. They may be of formula (when both the metal of the salt and the metallo-substituent are monovalent) where each R represents hydrogen or hydrocarbon groups which can be the same or different, R<SP>1</SP> is an alkylene group and M and M<SP>l</SP> are metals which may be the same or different. It is preferred that M and M<SP>1</SP> are alkali or alkaline earth metals. They may be prepared by reacting a metal salt of a 2-carboxy-propene with a metallating agent such as a metal amide, hdyride or in some cases the metal itself and compounds of formula RxM. Lower alkyl derivatives of metal amides may also be used. Compounds specified include sodium, potassium, lithium, calcium and magnesium amides, potassium, aluminium, magnesium, cacsium, beryllium, rubidium, copper, titanium and zirconium hydrides, amyl sodium, disodiooctadiene, dimethyl and diethyl zinc. The reaction may be carried out at a temperature between 160‹C. and 300‹C. The reactants should be of particle size below about 50 microns. An inert atmosphere such as argon, nitrogen or krypton is employed: in some circumstances it is preferred to carry out the reaction under an inert liquid blanket such as a high boiling hydrocarbon oil. Sub-atmospheric pressure may be used to ensure rapid removal of volatile by-products. Many metal salts according to the invention are specified. The compounds of the invention are highly reactive. Carbonation with solid carbon dioxide followed by hydrolysis yields dicarboxylic acid (e.g. the sodium salt of 2-carboxy-3-sodiopropene yields itaconic acid). Alkylation yields longer chain acid salts, and using excess of an organo halide the compounds yield esters of long chain acids. Reaction with compounds of formula RX 2 where X is a functional group reactive with the 3-metallo substituent yields polyester derivatives. Sulphur gives rise to the sodium mercaptide, and epoxidation gives rise to the appropriate metallic hydroxy alkanates. Transmetallation gives rise to organo metallic compounds, e.g. the sodium salt of 2-carboxy-3- sodio propene reacts with a trialkyl tin halide to give the sodium salt of 2-carboxy-3-(trialkyl tin)- propene.
GB40568/59A 1958-12-02 1959-11-30 Metal salts of 2-carboxy-3-metallo-propenes Expired GB893268A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US893268XA 1958-12-02 1958-12-02
US846819A US3108134A (en) 1959-10-16 1959-10-16 Metallometallic salt of unsaturated carboxylic acid

Publications (1)

Publication Number Publication Date
GB893268A true GB893268A (en) 1962-04-04

Family

ID=31980818

Family Applications (2)

Application Number Title Priority Date Filing Date
GB40568/59A Expired GB893268A (en) 1958-12-02 1959-11-30 Metal salts of 2-carboxy-3-metallo-propenes
GB34921/60A Expired GB912559A (en) 1958-12-02 1960-10-12 Metallic salts

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB34921/60A Expired GB912559A (en) 1958-12-02 1960-10-12 Metallic salts

Country Status (3)

Country Link
DE (2) DE1155778B (en)
FR (2) FR1243589A (en)
GB (2) GB893268A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1240699A (en) * 1984-05-14 1988-08-16 Thomas R. Verhoeven Preparation of dibenzo(b,f)thiepin compounds

Also Published As

Publication number Publication date
FR1270929A (en) 1961-09-01
GB912559A (en) 1962-12-12
DE1155778B (en) 1963-10-17
DE1175671B (en) 1964-08-13
FR1243589A (en) 1961-01-16

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