GB654035A - Manufacture of beta-isopropylnaphthalene hydroperoxide and beta-naphthol - Google Patents

Manufacture of beta-isopropylnaphthalene hydroperoxide and beta-naphthol

Info

Publication number
GB654035A
GB654035A GB2820248A GB2820248A GB654035A GB 654035 A GB654035 A GB 654035A GB 2820248 A GB2820248 A GB 2820248A GB 2820248 A GB2820248 A GB 2820248A GB 654035 A GB654035 A GB 654035A
Authority
GB
United Kingdom
Prior art keywords
isopropylnaphthalene
hydroperoxide
naphthol
carried out
oxidation
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
GB2820248A
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 GB2820248A priority Critical patent/GB654035A/en
Publication of GB654035A publication Critical patent/GB654035A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
    • 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
    • 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

Landscapes

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

Abstract

b -Isopropylnaphthalene hydroperoxide is prepared by oxidizing b -isopropylnaphthalene in the liquid phase in the substantial absence of heavy metal oxidation catalysts at elevated temperatures with molecular oxygen, it may then be treated with acidic substances to give b -naphthol. The oxidation is preferably carried out between 100 DEG and 150 DEG C., e.g. 110-135 DEG C., and in the presence of an alkaline substance, e.g. alkali metal carbonates or hydroxides, tertiary alkali metal phosphates, and sodium bicarbonate. The oxygen may be mixed with inert gases or vapours, e.g. nitrogen, carbon dioxide or steam. The process may be either batch or continuous, and may be carried out with the b -isopropylnaphthalene dispersed in water with, e.g., stearates, oleates, and lauryl sulphates, with the pH maintained between 7 and 12 with alkali, and the temperature between 70 DEG C. and the boiling-point of water at the operating pressure. The oxidation may be carried out in an inert solvent, or excess isopropylnaphthalene; the hydroperoxide may be isolated, e.g. by distillation or extraction. The hydrolysis of the peroxide is preferably done at elevated temperatures; an inert solvent may be used, e.g. unchanged isopropylnaphthalene. Many suitable acids are specified, e.g. sulphuric acid, and other acidic substances, e.g. aluminium chloride and regenerated hydrogen ion-exchange materials. Acetone is a by-product in this hydrolysis. b -Isopropylnaphthalene is prepared by alkylation of naphthalene with propylene. In the examples, (1-5), b -isopropylnaphthalene is oxidized to the hydroperoxide and (6-10), subsequently hydrolysed to b -naphthol.
GB2820248A 1948-10-30 1948-10-30 Manufacture of beta-isopropylnaphthalene hydroperoxide and beta-naphthol Expired GB654035A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2820248A GB654035A (en) 1948-10-30 1948-10-30 Manufacture of beta-isopropylnaphthalene hydroperoxide and beta-naphthol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2820248A GB654035A (en) 1948-10-30 1948-10-30 Manufacture of beta-isopropylnaphthalene hydroperoxide and beta-naphthol

Publications (1)

Publication Number Publication Date
GB654035A true GB654035A (en) 1951-05-30

Family

ID=10271916

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2820248A Expired GB654035A (en) 1948-10-30 1948-10-30 Manufacture of beta-isopropylnaphthalene hydroperoxide and beta-naphthol

Country Status (1)

Country Link
GB (1) GB654035A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2727927A (en) * 1954-06-02 1955-12-20 American Cyanamid Co Recovery of beta-naphthol
US2771491A (en) * 1953-09-21 1956-11-20 Hercules Powder Co Ltd Selective oxidation of beta-isopropylnaphthalene to beta-isopropylnaphthalene hydroperoxide
DE969234C (en) * 1951-11-08 1958-05-14 Bayer Ag Process for the production of aromatic or hydroaromatic hydroperoxides
DE969266C (en) * 1951-04-28 1958-05-14 Rhone Poulenc Sa Process for the production of cumene hydroperoxide by the catalytic oxidation of cumene
US2911391A (en) * 1952-12-31 1959-11-03 Hercules Powder Co Ltd Polymer hydroperoxides
EP0370729A1 (en) * 1988-11-25 1990-05-30 Mitsui Petrochemical Industries, Ltd. Process for producing isopropylnaphthols
EP0796833A2 (en) * 1996-03-20 1997-09-24 Rütgers Kureha Solvents GmbH Process for the preparation of hydroxyaromatics

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE969266C (en) * 1951-04-28 1958-05-14 Rhone Poulenc Sa Process for the production of cumene hydroperoxide by the catalytic oxidation of cumene
DE969234C (en) * 1951-11-08 1958-05-14 Bayer Ag Process for the production of aromatic or hydroaromatic hydroperoxides
US2911391A (en) * 1952-12-31 1959-11-03 Hercules Powder Co Ltd Polymer hydroperoxides
US2771491A (en) * 1953-09-21 1956-11-20 Hercules Powder Co Ltd Selective oxidation of beta-isopropylnaphthalene to beta-isopropylnaphthalene hydroperoxide
DE1015431B (en) * 1953-09-21 1957-09-12 Distillers Co Yeast Ltd Process for the preparation of ª‰-isopropylnaphthalene hydroperoxide
US2727927A (en) * 1954-06-02 1955-12-20 American Cyanamid Co Recovery of beta-naphthol
EP0370729A1 (en) * 1988-11-25 1990-05-30 Mitsui Petrochemical Industries, Ltd. Process for producing isopropylnaphthols
EP0796833A2 (en) * 1996-03-20 1997-09-24 Rütgers Kureha Solvents GmbH Process for the preparation of hydroxyaromatics
EP0796833A3 (en) * 1996-03-20 1998-04-01 Rütgers Kureha Solvents GmbH Process for the preparation of hydroxyaromatics
US6107527A (en) * 1996-03-20 2000-08-22 Rutgers Kureha Solvents Gmbh Process for the production of hydroxy-aromatic substances
CN1080714C (en) * 1996-03-20 2002-03-13 吕特哥斯库勒哈溶剂有限公司 Process for production of hydroxy-aromatic substances

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