GB844825A - Preparation of oxygenated products from cyclic mono-olefins by ozonization and oxidation - Google Patents

Preparation of oxygenated products from cyclic mono-olefins by ozonization and oxidation

Info

Publication number
GB844825A
GB844825A GB27174/58A GB2717458A GB844825A GB 844825 A GB844825 A GB 844825A GB 27174/58 A GB27174/58 A GB 27174/58A GB 2717458 A GB2717458 A GB 2717458A GB 844825 A GB844825 A GB 844825A
Authority
GB
United Kingdom
Prior art keywords
group
ozonization
vinyl
heptene
bicyclo
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
GB27174/58A
Inventor
Philip Sigmon Bailey
Robert Hood Perry Jr
Charles Anschel Cohen
Leland Kenneth Beach
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering Co
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 Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Publication of GB844825A publication Critical patent/GB844825A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
    • C07D323/02—Five-membered rings
    • 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
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/34—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with ozone; by hydrolysis of ozonides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C07D321/02—Seven-membered rings
    • C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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)

Abstract

Vinyl monomers are polymerized with a catalyst comprising the products obtained by ozonizing a bicyclo (2.2.1)-2 heptene dissolved in a normal C1 to C10 aliphatic alcohol (see Group IV(b)). The ozonization products may be represented by the formula: <FORM:0844825/IV(a)/1> wherein R is hydrogen or a C1 to C4 alkyl group, P and R11 taken together are a cyclizing peroxide group and R111 is OH or OR1 and otherwise P is a hydroperoxide group and R11 and R111 taken together are oxygen and R1 is a normal C1 to C10 alkyl group. Vinyl monomers specified include styrene, methyl acrylate and methacrylate acrylonitrile, vinyl acetate, vinyl halides such as vinyl chloride, vinyl ketones, vinyl sulphonamides, butadiene, chloroprene and mixtures thereof. The polymerization may be carried out as a mass, suspension, solution or emulsion process, The polymerization of methyl methacrylate and styrene in the presence of a mixture obtained by ozonizing norbonnylene in methanol is described.ALSO:A process for preparing a dicarboxylic acid from a bicyclo (2,2.1)-2-heptene comprises reacting the bicyclo (2,2.1)-2-heptene with ozone in the presence of a solvent for the heptene at a temperature of from -100 DEG C. to +30 DEG C. and oxidising the reaction product thus obtained with hydrogen peroxide or molecular oxygen containing a catalytic amount of ozone in the presence of water and/or aliphatic monocarboxylic acids to obtain a dicarboxylic acid. Olefinic starting materials specified include norbornylene, 5-methyl-5-ethyl-, 5-propyl-, 5,5,6-trimethyl and 5,6-dimethyl bicyclo (2,2.1)-2-heptenes. Solvents specified for use in the ozonization step include lower aliphatic acids e.g. formic and acetic acids, esters of C1 to C14 aliphatic alcohols with C1 to C4 monocarboxylic acids e.g. methyl and ethyl formates and acetates and halogenated hydrocarbons such as carbon tetrachloride and chloroform which are inert under the reaction conditions. Alternatively C1 to C10 aliphatic alcohols may be employed as solvents in the first step when alkoxy peroxides of the formula: <FORM:0844825/IV(b)/1> wherein R represents hydrogen or a C1 to C4 alkyl group and P and R11 taken together are a cyclizing peroxide group and R111 is OH or OR1 or otherwise P is a hydroperoxide group and R11 and R111 taken together are oxygen and wherein R1 is a normal C1 to C10 alkyl group, are obtained. The ozonization of norbornylene in the presence of inert solvents and methanol and the subsequent oxidation of the ozonization products to cis-1,3-cyclopentane dicarboxylic acids by means of hydrogen peroxide and aqueous formic acid or a mixture of oxygen and ozone are described. The ozonization products catalize the polymerization of vinyl monomers (see Group IV(a)).
GB27174/58A 1957-09-26 1958-08-25 Preparation of oxygenated products from cyclic mono-olefins by ozonization and oxidation Expired GB844825A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US1093358XA 1957-09-26 1957-09-26

Publications (1)

Publication Number Publication Date
GB844825A true GB844825A (en) 1960-08-17

Family

ID=22327119

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27174/58A Expired GB844825A (en) 1957-09-26 1958-08-25 Preparation of oxygenated products from cyclic mono-olefins by ozonization and oxidation

Country Status (2)

Country Link
DE (1) DE1093358C2 (en)
GB (1) GB844825A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR9201627A (en) * 1991-05-02 1992-12-15 Hoechst Ag PROCESS FOR THE PREPARATION OF POLYCARBOXYLIC ACIDS WITH AT LEAST THREE CARBOXYL GROUPS AND THEIR DERIVATIVES

Also Published As

Publication number Publication date
DE1093358B (en) 1960-11-24
DE1093358C2 (en) 1961-05-10

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