CH503671A - Isomerisation of 3-carene to 4-carene, and production - of d-trans-isolimonene, d-trans-2-methane,l-methol - Google Patents

Isomerisation of 3-carene to 4-carene, and production - of d-trans-isolimonene, d-trans-2-methane,l-methol

Info

Publication number
CH503671A
CH503671A CH964667A CH964667A CH503671A CH 503671 A CH503671 A CH 503671A CH 964667 A CH964667 A CH 964667A CH 964667 A CH964667 A CH 964667A CH 503671 A CH503671 A CH 503671A
Authority
CH
Switzerland
Prior art keywords
trans
carene
isolimonene
converted
psig
Prior art date
Application number
CH964667A
Other languages
German (de)
Inventor
Bogert Booth Albert
Original Assignee
Hercules Inc
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 US563383A external-priority patent/US3407242A/en
Priority claimed from US563370A external-priority patent/US3407241A/en
Application filed by Hercules Inc filed Critical Hercules Inc
Publication of CH503671A publication Critical patent/CH503671A/en

Links

Classifications

    • 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
    • C07C13/16—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring
    • C07C13/20—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring with a cyclohexene ring
    • C07C13/21—Menthadienes
    • 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
    • C07C13/16—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring
    • C07C13/20—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring with a cyclohexene ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • C07C5/05—Partial hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
    • C07C5/25—Migration of carbon-to-carbon double bonds
    • C07C5/2506—Catalytic processes
    • C07C5/2556—Catalytic processes with metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
    • C07C5/25—Migration of carbon-to-carbon double bonds
    • C07C5/2506—Catalytic processes
    • C07C5/2562—Catalytic processes with hydrides or organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
    • C07C5/25—Migration of carbon-to-carbon double bonds
    • C07C5/2506—Catalytic processes
    • C07C5/2562—Catalytic processes with hydrides or organic compounds
    • C07C5/2575—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
    • C07C5/31—Rearrangement of carbon atoms in the hydrocarbon skeleton changing the number of rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • 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
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Abstract

3-Carene is converted into 4-carene in high yield by isomerisation over a noble metal, base metal or metal oxide hydrogenation catalyst in the presence of H2 at elevated temp. and pressure. Specifically, d-3-carene is used, the catalyst is Cu chromite and H2 pressure is 50 psig., or the catalyst is Ni or Pd, temp. 125-175 degrees and pressure 50-500 psig. Alternatively, a strong base can be used, opt. in the presence of a promoter. The d-4-carene obtd. is converted to d-trans-isolimonene by heating to 180 degrees. The isolimonene can be polymerised to a hard terpene resin, and d-trans-isolimonene can also be selectively hydrogenated to d-trans-2-menthene which can be converted to laevo-menthol. Pt and pref. Ru are suitable catalysts, at a conc. of is not >1 wt.%, at 0-100 degrees and up to 100 psig. The d-trans-2-menthene can also be produced by 1) treatment with a hydrogen halide followed by dehalogenation, or 2) treatment with Al(iBu)3 to give the Al deriv. which is then decomposed by active H cpds., e.g. H2O, with sepn. of Al(OH)3. The d-trans-isolimonene can also be isomerised to d-2,4(8)-p-menthadiene by a strong base, e.g. KOBu-t/Me2SO, which can be converted by known means to l-menthol.
CH964667A 1966-07-07 1967-07-06 Isomerisation of 3-carene to 4-carene, and production - of d-trans-isolimonene, d-trans-2-methane,l-methol CH503671A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US563383A US3407242A (en) 1966-07-07 1966-07-07 Isomerization of 3-carene to 4-carene and further conversion of the 4-carene
US563370A US3407241A (en) 1966-07-07 1966-07-07 Isomerization of 3-carene to 4-carene and further conversion of 4-carene

Publications (1)

Publication Number Publication Date
CH503671A true CH503671A (en) 1971-02-28

Family

ID=27073270

Family Applications (2)

Application Number Title Priority Date Filing Date
CH1740170A CH525849A (en) 1966-07-07 1967-07-06 Process for the production of d-2,4 (8) -p-menthadiene
CH964667A CH503671A (en) 1966-07-07 1967-07-06 Isomerisation of 3-carene to 4-carene, and production - of d-trans-isolimonene, d-trans-2-methane,l-methol

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH1740170A CH525849A (en) 1966-07-07 1967-07-06 Process for the production of d-2,4 (8) -p-menthadiene

Country Status (4)

Country Link
JP (1) JPS5231861B1 (en)
CH (2) CH525849A (en)
DE (1) DE1618521A1 (en)
GB (1) GB1194710A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56127533U (en) * 1980-02-21 1981-09-28
JPS6191813A (en) * 1984-10-11 1986-05-09 シャープ株式会社 Transparent touch panel
JPS636645U (en) * 1986-06-30 1988-01-18

Also Published As

Publication number Publication date
JPS5231861B1 (en) 1977-08-17
GB1194710A (en) 1970-06-10
CH525849A (en) 1972-07-31
DE1618521A1 (en) 1972-06-08

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Legal Events

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