GB751598A - Meta-substituted phenols and method for their synthesis - Google Patents

Meta-substituted phenols and method for their synthesis

Info

Publication number
GB751598A
GB751598A GB34979/53A GB3497953A GB751598A GB 751598 A GB751598 A GB 751598A GB 34979/53 A GB34979/53 A GB 34979/53A GB 3497953 A GB3497953 A GB 3497953A GB 751598 A GB751598 A GB 751598A
Authority
GB
United Kingdom
Prior art keywords
hydroperoxides
isopropyl
acid
tri
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
GB34979/53A
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.)
Occidental Chemical Corp
Original Assignee
Hooker Electrochemical 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 Hooker Electrochemical Co filed Critical Hooker Electrochemical Co
Publication of GB751598A publication Critical patent/GB751598A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/04—Phenol
    • 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
    • C07C409/00—Peroxy compounds
    • 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
    • C07C409/04—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 being acyclic
    • C07C409/08—Compounds containing six-membered aromatic rings
    • 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
    • C07C409/04—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 being acyclic
    • C07C409/08—Compounds containing six-membered aromatic rings
    • C07C409/10—Cumene hydroperoxide
    • 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
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/08—Acetone

Landscapes

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

Abstract

The invention comprises 3:5-di-isopropyl phenol and 5-isopropyl resorcinol, and a process for their manufacture wherein a mono- or di-hydroperoxide of 1:3:5-tri-isopropyl benzene is ketonically decomposed. Phloroglucinol is obtained by decomposition of the trihydroperoxide. The hydroperoxides are prepared by the oxidation with oxygen or an oxygen-containing gas of 1:3:5-tri-isopropyl benzene, alone or in the presence of a catalyst such as sodium hydroxide, potassium hydroxide, calcium hydroxide, pyridine, tribenzylamine, iron stearate, copper acetate or hexa-pyridine cobaltic chloride. An induction period in the oxidation is overcome by the addition of a small amount of the monohydroperoxide. For the preparation of the monohydroperoxide conversions of up to 30 per cent calculated as monohydroperoxide are employed. Similarly for the di- and tri-hydroperoxides conversions of 60-80 per cent and of at least 80 per cent respectively are employed. The monohydroperoxide is separated from the di- and tri-hydroperoxides by fractional distillation or by precipitating the di- and tri-hydroperoxides as their sodium or other suitable salts. The di- and tri-hydroperoxides are separated by fractional crystallization. The separated hydroperoxides may be decomposed to give acetone and 3:5-di-isopropyl phenol or 5-isopropyl resorcinol or phloroglucinol, or alternatively the mixture of hydroperoxides is decomposed and the phenols separated by known methods. The ketonic decomposition occurs when the hydroperoxides are heated or treated with ultra-violet light but preferably acid decomposing agents are used such as organic sulphonic acids, ferric chloride, perchloric acid, sulphuric acid, phosphoric acid, hydrochloric acid, trichloracetic acid and hydrogen chloride. 3:5-Di-isopropyl phenol forms phenolic resins when reacted with formaldehyde in acid or alkaline medium and 5-isopropyl resorcinol reacts with formaldehyde to form a liquid glue. The preparation of the hydroperoxides from 1:3:5-tri-isopropyl benzene by heating and passing air in the presence of catalysts and the monohydroperoxide, by heating in the presence of air and a metal naphthenate, and by heating in a thin film in air is described. In Examples (1) a solution of the monohydroperoxide in 1:3:5-tri-isopropyl benzene is decomposed with p-toluene sulphonic acid and 3:5-di-isopropyl phenol recovered and converted into the corresponding phosphate by reaction with phosphorus oxychloride; (2) a solution of the dihydroperoxide in toluene is added to a toluene solution of p-toluene sulphonic acid and 5-isopropyl resorcinol obtained; (3) a solution of the trihydroperoxide in glacial acetic acid is decomposed by the addition of perchloric acid and phloroglucinol obtained. Specification 754,125, [Group IV (a)], is referred to.
GB34979/53A 1952-12-18 1953-12-16 Meta-substituted phenols and method for their synthesis Expired GB751598A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US751598XA 1952-12-18 1952-12-18

Publications (1)

Publication Number Publication Date
GB751598A true GB751598A (en) 1956-06-27

Family

ID=22123950

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34979/53A Expired GB751598A (en) 1952-12-18 1953-12-16 Meta-substituted phenols and method for their synthesis

Country Status (1)

Country Link
GB (1) GB751598A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5888356A (en) * 1981-11-19 1983-05-26 Sumitomo Chem Co Ltd Preparation of triisopropylbenzene trihydroperoxide
US4463197A (en) * 1981-12-01 1984-07-31 Sumitomo Chemical Company, Limited Method for purifying phloroglucin
US4463199A (en) * 1981-12-01 1984-07-31 Sumitomo Chemical Company, Limited Method for producing phloroglucin
US4469899A (en) * 1981-08-27 1984-09-04 Sumitomo Chemical Company, Limited Process for producing phloroglucin

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4469899A (en) * 1981-08-27 1984-09-04 Sumitomo Chemical Company, Limited Process for producing phloroglucin
JPS5888356A (en) * 1981-11-19 1983-05-26 Sumitomo Chem Co Ltd Preparation of triisopropylbenzene trihydroperoxide
JPS6345666B2 (en) * 1981-11-19 1988-09-12 Sumitomo Chemical Co
US4463197A (en) * 1981-12-01 1984-07-31 Sumitomo Chemical Company, Limited Method for purifying phloroglucin
US4463199A (en) * 1981-12-01 1984-07-31 Sumitomo Chemical Company, Limited Method for producing phloroglucin

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