GB786341A - Manufacture of catechol - Google Patents

Manufacture of catechol

Info

Publication number
GB786341A
GB786341A GB5366/55A GB536655A GB786341A GB 786341 A GB786341 A GB 786341A GB 5366/55 A GB5366/55 A GB 5366/55A GB 536655 A GB536655 A GB 536655A GB 786341 A GB786341 A GB 786341A
Authority
GB
United Kingdom
Prior art keywords
catechol
dihydroperoxide
tetrahydronaphthalene
decomposition
monohydroperoxide
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
GB5366/55A
Inventor
Donald Peter Young
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.)
Distillers Co Yeast Ltd
Distillers Co Ltd
Original Assignee
Distillers Co Yeast Ltd
Distillers Co Ltd
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 Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Priority to GB5366/55A priority Critical patent/GB786341A/en
Priority to FR1200025D priority patent/FR1200025A/en
Publication of GB786341A publication Critical patent/GB786341A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
    • 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
    • C07C407/00—Preparation of peroxy compounds
    • C07C407/003—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

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

Abstract

Catechol is prepared by oxidizing, in the liquid phase by means of molecular oxygen, a 1 : 2 : 3 : 4-tetrahydronaphthalene which is substituted by a straight-chain alkyl group in each of the 1 and 4 positions, to a 1 : 4-dialkyl-1 : 2 : 3 : 4 - tetrahydronaphthalene dihydroperoxide, decomposing the dihydroperoxide by means of an acidic catalyst and recovering catechol from the decomposition mixture. Specified 1 : 4 - dialkyl - 1 : 2 : 3 : 4 - tetrahydro - naphthalenes are 1 : 4 - dimethyl- or -diethyl-or -dipropyl- or -dibutyl- or 1-methyl-4-ethyl-1 : 2 : 3 : 4 - tetrahydronaphthalene. The oxidation is conveniently carried out at 60-120 DEG C. and preferably in the presence of an alkali such as an alkali metal hydroxide or carbonate or an alkaline earth metal oxide or hydroxide. The oxidation product contains the dihydroperoxide, which exists as cis and trans isomers, and some monohydroperoxide. The dihydroperoxide can be extracted from the oxidation product with aqueous alkali metal hydroxide and it is preferred to decompose the extracted dihydroperoxide rather than the mixture containing the monohydroperoxide. The decomposition is carried out by treating the dihydroperoxides, preferably in solution in an inert organic solvent at elevated temperatures with an acidic catalyst such as sulphuric acid or alkanesulphonic acids. The decomposition produces as well as the catechol, diketones and minor amounts of diketophenols. Thus, 1:4-diethyl - 1 : 2 : 3 : 4 - tetrahydronaphthalene dihydroperoxide gives catechol, octane-3 : 6-dione and minor amounts of 1-o-hydroxybenzoylpentan-3-one. The catechol is extracted from the decomposition mixture by distilling it preferably after neutralization of the acid catalyst, dissolving the residue in an organic solvent such as benzene or carbon tetrachloride and extracting the catechol with water. The diketone can be recovered from the organic solvent layer. In examples: (1) 1 : 4 - diethyl - 1 : 2 : 3 : 4 - tetrahydronaphthalene was oxidized with oxygen in the presence of aqueous sodium carbonate or potassium carbonate, or calcium hydroxide, the dihydroperoxide extracted with aqueous sodium hydroxide and separated into its isomers (in one example the monohydroperoxide is also isolated) either of which on decomposition with sulphuric acid or a mixed alkanesulphonic acid gave catechol, octane-3 : 6-dione and a small amount of 1 - o - hydroxybenzoylpentan - 3 - one; (2) 1 : 4 - dimethyl - 1 : 2 : 3 : 4 - tetrahydronaph - was oxidized with oxygen in the presence of aqueous sodium carbonate, the dihydroperoxide isomers and monohydroperoxide isolated, the mixture of the dihydroperoxides and one of the isomers being decomposed with sulphuric acid to give catechol and acetonylacetone. Specification 646,102 is referred to.
GB5366/55A 1955-02-23 1955-02-23 Manufacture of catechol Expired GB786341A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB5366/55A GB786341A (en) 1955-02-23 1955-02-23 Manufacture of catechol
FR1200025D FR1200025A (en) 1955-02-23 1956-02-03 Catechol preparation process

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5366/55A GB786341A (en) 1955-02-23 1955-02-23 Manufacture of catechol

Publications (1)

Publication Number Publication Date
GB786341A true GB786341A (en) 1957-11-13

Family

ID=9794743

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5366/55A Expired GB786341A (en) 1955-02-23 1955-02-23 Manufacture of catechol

Country Status (2)

Country Link
FR (1) FR1200025A (en)
GB (1) GB786341A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4339613A (en) * 1980-03-14 1982-07-13 Pcuk Produits Chimiques Ugine Kuhlmann Superacid catalyzed preparation of resorcinol from meta-diisopropylbenzene

Also Published As

Publication number Publication date
FR1200025A (en) 1959-12-17

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