GB762340A - Unsaturated polycarbonyl compounds and a process for preparing them - Google Patents

Unsaturated polycarbonyl compounds and a process for preparing them

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Publication number
GB762340A
GB762340A GB35483/54A GB3548354A GB762340A GB 762340 A GB762340 A GB 762340A GB 35483/54 A GB35483/54 A GB 35483/54A GB 3548354 A GB3548354 A GB 3548354A GB 762340 A GB762340 A GB 762340A
Authority
GB
United Kingdom
Prior art keywords
dicarboxylic acid
carbon atoms
dimethyl
methyl
octadecadiene
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
GB35483/54A
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.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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 Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Publication of GB762340A publication Critical patent/GB762340A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/40—Peroxy compounds containing nitrogen atoms
    • 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
    • C07C407/00—Preparation of peroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
    • C07C409/14—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom belonging to a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/16—Peroxy compounds the —O—O— group being bound between two carbon atoms not further substituted by oxygen atoms, i.e. peroxides
    • C07C409/18—Peroxy compounds the —O—O— group being bound between two carbon atoms not further substituted by oxygen atoms, i.e. peroxides at least one of the carbon atoms belonging to a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/20—Peroxy compounds the —O—O— group being bound to a carbon atom further substituted by singly—bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/20—Peroxy compounds the —O—O— group being bound to a carbon atom further substituted by singly—bound oxygen atoms
    • C07C409/22—Peroxy compounds the —O—O— group being bound to a carbon atom further substituted by singly—bound oxygen atoms having two —O—O— groups bound to the carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
    • C07C49/796—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring polycyclic
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/54—Halogenated acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Diethylenic dicarboxylic acids of the formula <FORM:0762340/IV(a)/1> wherein each R represents a hydrogen atom, a halogen atom or a hydrocarbon radical comprising 1-12 carbon atoms, and n is an integer equalling 3-9 (inclusive) and esters thereof are suitable for use as plasticisers for nitrocellulose and polyvinyl chloride resins. These compounds may be obtained by reacting a compound having 4-18 carbon atoms and having 2 conjugated double bonds, e.g. butadiene, chloroprene, isoprene and derivatives thereof with a cyclic peroxide obtained, for example, by reacting hydrogen peroxide with cyclohexanone, methyl cyclohexanone, cyclopentanone, and methyl cyclopentanone, in the presence of a redox reducing agent. Octadecadiene-7,11-dicarboxylic acid-1,18 and others are mentioned.ALSO:The invention comprises an unsaturated polycarbonyl compound of the general formula: <FORM:0762340/IV(b)/1> in which R represents a hydrogen atom, a halogen atom or a hydrocarbon radical comprising 1-12 carbon atoms, each symbol A represents a bivalent hydrocarbon radical having a carbon chain of 3-9 (inclusive) carbon atoms and each symbol X represents an hydroxyl, cyano, hydrocarbon, alkoxy, cycloalkoxy or aryloxy group, the last four of which may contain each 1-12 (inclusive) carbon atoms, and the preparation thereof by reacting a compound containing 4-18 (inclusive) carbon atoms in its molecule and having two conjugated double bonds, in the presence of a redox reducing agent, with a cyclic peroxide of the general formula: <FORM:0762340/IV(b)/2> in which the additional symbols X1 and Y1 are such that X1 represents an hydroxyl, hydroperoxy, cyano, hydrocarbon, alkoxy, cycloalkoxy or aryloxy group, the last four of which may each comprise 1-12 carbon atoms, and Y represents a hydrogen atom or an <FORM:0762340/IV(b)/3> radical. The cyclic peroxides used as starting materials and having the formulae: <FORM:0762340/IV(b)/4> and <FORM:0762340/IV(b)/5> can be obtained by reacting a cyclic ketone with hydrogen peroxide, e.g. by reacting cyclohexanone, cyclopentanone, methyl cyclopentanone, methyl cyclohexanone with hydrogen peroxide. Additionally compounds of the formula: <FORM:0762340/IV(b)/6> wherein R1 represents a hydrocarbon radica containing 1-12 carbon atoms and compounds of the formula: <FORM:0762340/IV(b)/7> wherein Z represents a hydrocarbon radical, a cyano, carboxy or alkoxy group may be utilized. The other starting material may comprise butadiene, chloroprene, isoprene and derivatives thereof. As redox reducing agent there may be used ferrous ions, chromous irons, vanadous ions, sodium bisulphite, sodium formaldehyde sulphoxylate and l-ascorbic acid. The reaction may be effected in acid medium between -15 DEG and 50 DEG C. Examples disclose the production of (1) the diethylenic dibasic acid HOOC-(CH2)5-(C4H6)2 -(CH2)5-COOH and dichloro-octadecadiene 7,11-dicarboxylic acids-1,18; (2) octadecadiene-7,11-dicarboxylic acid - 1,18, the dimethyl esters of 7-vinyl-hexadecene-9-dicarboxylic acid-1,16, esters of dimethyl-octadecadiene-7,11-dicarboxylic acids-1,18, 7,9- and 7,10-dimethyl-7-vinylhexadecene-9-dicarboxylic acid-1,16 and 9 and 10-methyl-7-isopropenyl - hexadecene - 9 - dicarboxylic acid-1,16; (3) the same dimethyl esters of the C20-diethylenic dicarboxylic acids as Example (2); (4) the dimethyl esters of hexadecadiene-6,10-dicarboxylic acid-1,16 and 6-vinyl-tetradecene-8-dicarboxylic acid-1,14, the dimethyl ester of dichlorohexadecadiene-6,10-dicarboxylic acid-1,16, the methyl ester of octadecadiene-7,11-dicarboxylic acid-1,18, and the C22-diketonitrile having the formula NC-CO-(CH2)6-CH = CH-(CH2)2-CH = CH-(CH2)6-CO-CN; (5) a mixture of the methyl esters of 3,16-dimethyl - octadecadiene - 7,11 - dicarboxylic acid - 1,18 and 3,14 - dimethyl - 7 - vinyl-hexadecene - 9 - dicarboxylic acid - 1,16; (6) compounds having the formulae: <FORM:0762340/IV(b)/8> (7) the diketone <FORM:0762340/IV(b)/9>
GB35483/54A 1953-12-07 1954-12-07 Unsaturated polycarbonyl compounds and a process for preparing them Expired GB762340A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US762340XA 1953-12-07 1953-12-07

Publications (1)

Publication Number Publication Date
GB762340A true GB762340A (en) 1956-11-28

Family

ID=22130743

Family Applications (1)

Application Number Title Priority Date Filing Date
GB35483/54A Expired GB762340A (en) 1953-12-07 1954-12-07 Unsaturated polycarbonyl compounds and a process for preparing them

Country Status (2)

Country Link
FR (1) FR1121551A (en)
GB (1) GB762340A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1192640B (en) * 1961-12-05 1965-05-13 Basf Ag Process for the production of mixed oligomers from 1, 3-dienes and acrylic acid esters, acrylic acid amide or acrylic acid nitrile

Also Published As

Publication number Publication date
FR1121551A (en) 1956-08-21

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