GB1100250A - Separating tertiary phosphines from olefinic compounds - Google Patents

Separating tertiary phosphines from olefinic compounds

Info

Publication number
GB1100250A
GB1100250A GB38101/66A GB3810166A GB1100250A GB 1100250 A GB1100250 A GB 1100250A GB 38101/66 A GB38101/66 A GB 38101/66A GB 3810166 A GB3810166 A GB 3810166A GB 1100250 A GB1100250 A GB 1100250A
Authority
GB
United Kingdom
Prior art keywords
apo
vitamin
formula
olefinic compounds
radicals
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
GB38101/66A
Inventor
Werner Reif
Peter Haug
Herwig Freyschlag
Horst Pommer
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik 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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB1100250A publication Critical patent/GB1100250A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/12—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)

Abstract

Olefinic compounds of formula <FORM:1100250/C4-C5/1> where R4, R5, R6 and R7 are hydrogen atoms or saturated or unsaturated aliphatic, cycloaliphatic, araliphatic or aromatic radicals, the total number of carbon atoms being at least eight, and in which radicals R4 and R5 and/or R6 and R7 may form a fiveto eight-membered ring, said compounds being contaminated by tertiary phosphines of formula <FORM:1100250/C4-C5/2> where R1, R2 and R3 are aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbon radicals having one to eight carbon atoms, are purified by contacting water-insoluble organic solutions of the olefinic compounds with aqueous solutions of peroxides or with redox resins bearing peroxide groups to convert the phosphines to tertiary phosphine oxides of formula <FORM:1100250/C4-C5/3> and then separating the tertiary phosphine oxides, e.g. by extraction with suitable solvents. Olefinic compounds which may be purified include axerophthene and lycopene.ALSO:Olefinic compounds of formula <FORM:1100250/C2/1> where R4, R5, R6 and R7 are hydrogen atoms or saturated or unsaturated aliphatic, cyclo-aliphatic, araliphatic or aromatic radicals which may contain ester, ether, nitrile, carbonyl or hydroxyl groups, the total number of carbon atoms being at least eight, and in which radicals R4 and R5 and/or R6 and R7 may form a fiveto eight-membered ring, said compounds being contaminated by tertiary phosphines of formula <FORM:1100250/C2/2> where R1, R2 and R3 are aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbon radicals having one to eight carbon atoms, are purified by contacting water-insoluble organic solutions of the olefinic compounds with aqueous solutions of peroxides or with redox resins bearing peroxide groups to convert the phosphines to tertiary phosphine oxides of formula <FORM:1100250/C2/3> and then separating the teritary phosphine oxides, e.g. by extraction with suitable solvents. In examples, Vitamin A acid ethyl ester, Vitamin A acetate and Vitamin A palmitate, all containing triphenyl phosphine, are dissolved in octane, cyclohexane and light naphtha, and contacted with aqueous solutions of potassium hydrogen permonosulphate, hydrogen peroxide and permonosulphuric acid and with a peroxide redox resin, the phosphine oxides then being removed by extraction with mixtures of methanol and water and ethanol and water. Other olefinic compounds which may be purified are linalool, dehydrolinalool, a -ionone, b -ionone, Vitamin A aldehyde, Vitamin A2 acetate, Vitamin A2 acid ethyl ester, axeropthene, b - apo - 121 - carotenal, b - apo-121-carotenal acetate, b -apo-121-carotenic acid ethyl ester, b -apo-81-carotenal, b -apo-81-caro-tenal acetate, b -apo-81-carotenic acid ethyl ester, a -carotene, b -carotene, lycopene, farnesylacetone and isophytol.
GB38101/66A 1965-08-26 1966-08-25 Separating tertiary phosphines from olefinic compounds Expired GB1100250A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB0083449 1965-08-26

Publications (1)

Publication Number Publication Date
GB1100250A true GB1100250A (en) 1968-01-24

Family

ID=6981974

Family Applications (1)

Application Number Title Priority Date Filing Date
GB38101/66A Expired GB1100250A (en) 1965-08-26 1966-08-25 Separating tertiary phosphines from olefinic compounds

Country Status (4)

Country Link
BE (1) BE685922A (en)
CH (1) CH471050A (en)
DE (1) DE1518590B1 (en)
GB (1) GB1100250A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116249456A (en) * 2020-10-21 2023-06-09 三井农林株式会社 Brain function improving agent

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1088951B (en) * 1957-11-27 1960-09-15 Hoffmann La Roche Process for the preparation of polyenecarboxylic acids or their esters
DE1158505B (en) * 1962-05-23 1963-12-05 Basf Ag Process for the preparation of compounds of the axerophthylidene series
DE1068710B (en) * 1958-08-06 1959-11-12 Badische Anilin- &. Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein Process for the preparation of compounds of the beta-ionylidene ethylidene series
DE1110633B (en) * 1960-02-20 1961-07-13 Bayer Ag Process for the production of vitamin A acid nitrile or esters
DE1165582B (en) * 1961-11-08 1964-03-19 Bayer Ag Process for the production of terminal ª ‡, ª ‰ -unsaturated acetylene compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116249456A (en) * 2020-10-21 2023-06-09 三井农林株式会社 Brain function improving agent

Also Published As

Publication number Publication date
DE1518590B1 (en) 1970-05-21
BE685922A (en) 1967-02-24
CH471050A (en) 1969-04-15

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