GB960305A - Process for the production of cyclododecene with a preponderant content of cis-cyclododecene - Google Patents

Process for the production of cyclododecene with a preponderant content of cis-cyclododecene

Info

Publication number
GB960305A
GB960305A GB42198/62A GB4219862A GB960305A GB 960305 A GB960305 A GB 960305A GB 42198/62 A GB42198/62 A GB 42198/62A GB 4219862 A GB4219862 A GB 4219862A GB 960305 A GB960305 A GB 960305A
Authority
GB
United Kingdom
Prior art keywords
cyclododecene
distilled
heated
cyclododecadiene
diluent
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
GB42198/62A
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.)
Huels AG
Original Assignee
Chemische Werke Huels AG
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 Chemische Werke Huels AG filed Critical Chemische Werke Huels AG
Publication of GB960305A publication Critical patent/GB960305A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
    • C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
    • C07C1/323—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom the hetero-atom being a nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/273—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a twelve-membered ring
    • C07C13/275—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a twelve-membered ring the twelve-membered ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered

Landscapes

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

Abstract

Cyclododecene (mainly the cis isomer) is prepared by converting 1,5-cyclododecadiene in known manner to the monoepoxide which is catalytically isomerized to cyclododecenone and the semi-carbazone thereof is heated with an alkaline reagent in the presence of a diluent. The 1,5-cyclododecadiene may be prepared by heating the semicarbazone of cyclododecadien - (1,5) - one - (9) with an alkaline reagent in the presence of a diluent. The 1,5-cyclododecadiene, which may be dissolved in solvents e.g. ethyl acetate or acetone, is epoxidized with a solution of per-acids or hydrogen peroxide and organic acids or buffer solutions in a single or multiphase system. The epoxide is distilled off, heated to 115-125 DEG C. and an isomerisation catalyst e.g. magnesium iodide, is added and the mixture is stirred and distilled in vacuo. The cyclododecenone with at least a stoichiometric amount of semicarbazide hydrochloride is heated to boiling in the presence of potassium acetate in alcoholic or aqueous alcoholic solution. The solvent is then distilled off, the residue is treated with dilute strong acid e.g. hydrochloric acid, separated and heated with the alkaline reagents e.g. the alkali and alkaline earth metal alcoholates of aliphatic, cycloaliphatic monohydric or dihydric alcohols, higher polyglycols or monoglycol ethers. The organic phase of the mixture is then extracted and distilled to yield the cyclododecene. An excess of alcohol may be employed in the formation of the alcoholate when it serves as a diluent.
GB42198/62A 1961-11-09 1962-11-08 Process for the production of cyclododecene with a preponderant content of cis-cyclododecene Expired GB960305A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC25469A DE1150675B (en) 1961-11-09 1961-11-09 Process for the production of cyclododecene with predominant content of cis-cyclododecene

Publications (1)

Publication Number Publication Date
GB960305A true GB960305A (en) 1964-06-10

Family

ID=7017896

Family Applications (1)

Application Number Title Priority Date Filing Date
GB42198/62A Expired GB960305A (en) 1961-11-09 1962-11-08 Process for the production of cyclododecene with a preponderant content of cis-cyclododecene

Country Status (2)

Country Link
DE (1) DE1150675B (en)
GB (1) GB960305A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11203729B2 (en) 2014-04-24 2021-12-21 Firmenich Sa Unsaturated macrocyclic epoxide as perfuming ingredient

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1103325B (en) * 1959-12-21 1961-03-30 Huels Chemische Werke Ag Process for the preparation of cis- and trans-cyclododecene

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11203729B2 (en) 2014-04-24 2021-12-21 Firmenich Sa Unsaturated macrocyclic epoxide as perfuming ingredient

Also Published As

Publication number Publication date
DE1150675B (en) 1963-06-27

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