GB758665A - Process for the oxidation of mono-methyl naphthalenes - Google Patents

Process for the oxidation of mono-methyl naphthalenes

Info

Publication number
GB758665A
GB758665A GB2790253A GB2790253A GB758665A GB 758665 A GB758665 A GB 758665A GB 2790253 A GB2790253 A GB 2790253A GB 2790253 A GB2790253 A GB 2790253A GB 758665 A GB758665 A GB 758665A
Authority
GB
United Kingdom
Prior art keywords
water
products
acids
oxidation
separated
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
GB2790253A
Inventor
Edwin Fenton Chandley
Edward Teggin Borrows
Herbert Max Emil Steiner
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.)
Petrochemicals Ltd
Original Assignee
Petrochemicals 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 Petrochemicals Ltd filed Critical Petrochemicals Ltd
Priority to GB2790253A priority Critical patent/GB758665A/en
Priority to FR1109353D priority patent/FR1109353A/en
Priority to DE1954P0012826 priority patent/DE1004161B/en
Publication of GB758665A publication Critical patent/GB758665A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
    • C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
    • C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Monomethyl naphthalene is oxidized in the side chain by subjecting a monomethyl naphthalene in solution in a solvent comprising one or more fatty acids and containing a metallic oxidation catalyst in solution, to the action of oxygen at a temperature of from 150 DEG to 250 DEG C. with continuous removal of water formed from the reaction mixture, and recovering the resultant oxidation products. The process may be carried out at atmospheric or higher pressures. Specified solvents are fatty acids boiling below 250 DEG C.-such as acetic, propionic, butyric, isobutyric, isovaleric and caproic acids, the acids boiling between 150 DEG and 250 DEG C. being used at atmospheric or elevated pressures and those boiling below 150 DEG C. at elevated pressures. The acids form azeotropes with water and are used to remove water from the reaction mixture. The water may also be removed by a water-binding agent and the anhydrides of acetic, butyric, isobutyric and isovaleric acids are mentioned. The catalysts are organic salts such as cobalt and manganese acetates. Either a - or b -methyl naphthalene or a mixture of isomers may be used, and the material must be free of sulphur or sulphur compounds. The products are naphthoic acid, naphthaldehyde, naphthyl-methyl-naphthoate and, since the solvent is a fatty acid, the naphthyl-methyl ester thereof. These products may be separated from the oxidation product. Alternatively the oxidation product is hydrolysed, the naphthoic acid separated and the naphthyl carbinol, naphthaldehyde and unchanged methyl naphthalene recycled. In examples (1) b -methyl naphthalene, butyric acid and a mixture of cobalt and manganese acetates are placed in a cylindrical glass reactor heated to 195-200 DEG C., oxygen is passed in at the bottom, water is separated from the condensed vapours, and the products are separated by known methods; (2) as in (1) but using a mixture of a - and b -isomers; (3) as in (1) but the oxidation product is stripped free of butyric acid and catalyst and hydrolysed by refluxing with aqueous caustic soda, the naphthoic acid is removed and the non-acidic oxidation products recycled.
GB2790253A 1953-10-09 1953-10-09 Process for the oxidation of mono-methyl naphthalenes Expired GB758665A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB2790253A GB758665A (en) 1953-10-09 1953-10-09 Process for the oxidation of mono-methyl naphthalenes
FR1109353D FR1109353A (en) 1953-10-09 1954-10-06 Improvements to the oxidation processes of mono-methyl naphthalenes
DE1954P0012826 DE1004161B (en) 1953-10-09 1954-10-07 Process for the side chain oxidation of monomethylnaphthalene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2790253A GB758665A (en) 1953-10-09 1953-10-09 Process for the oxidation of mono-methyl naphthalenes

Publications (1)

Publication Number Publication Date
GB758665A true GB758665A (en) 1956-10-10

Family

ID=10267127

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2790253A Expired GB758665A (en) 1953-10-09 1953-10-09 Process for the oxidation of mono-methyl naphthalenes

Country Status (3)

Country Link
DE (1) DE1004161B (en)
FR (1) FR1109353A (en)
GB (1) GB758665A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3183279A (en) * 1961-05-11 1965-05-11 Sun Oil Co Purification of 2-methylnaphthalenes by selective oxidation of their isomers
EP0071166A1 (en) * 1981-07-24 1983-02-09 Hoechst Aktiengesellschaft Process for the preparation of aromatic aldehydes
US8471074B2 (en) 2007-03-14 2013-06-25 Solvay (Societe Anonyme) Process for the manufacture of dichloropropanol
US8507643B2 (en) 2008-04-03 2013-08-13 Solvay S.A. Composition comprising glycerol, process for obtaining same and use thereof in the manufacture of dichloropropanol
US8519198B2 (en) 2005-05-20 2013-08-27 Solvay (Societe Anonyme) Method for making an epoxide
US8536381B2 (en) 2008-09-12 2013-09-17 Solvay Sa Process for purifying hydrogen chloride
US8715568B2 (en) 2007-10-02 2014-05-06 Solvay Sa Use of compositions containing silicon for improving the corrosion resistance of vessels
US8795536B2 (en) 2008-01-31 2014-08-05 Solvay (Societe Anonyme) Process for degrading organic substances in an aqueous composition
US9309209B2 (en) 2010-09-30 2016-04-12 Solvay Sa Derivative of epichlorohydrin of natural origin
US9663427B2 (en) 2003-11-20 2017-05-30 Solvay (Société Anonyme) Process for producing epichlorohydrin

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1117098B (en) * 1957-09-16 1961-11-16 Sancier Aries Process for the production of phthalic anhydride

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3183279A (en) * 1961-05-11 1965-05-11 Sun Oil Co Purification of 2-methylnaphthalenes by selective oxidation of their isomers
EP0071166A1 (en) * 1981-07-24 1983-02-09 Hoechst Aktiengesellschaft Process for the preparation of aromatic aldehydes
US9663427B2 (en) 2003-11-20 2017-05-30 Solvay (Société Anonyme) Process for producing epichlorohydrin
US8519198B2 (en) 2005-05-20 2013-08-27 Solvay (Societe Anonyme) Method for making an epoxide
US8591766B2 (en) 2005-05-20 2013-11-26 Solvay (Societe Anonyme) Continuous process for preparing chlorohydrins
US8471074B2 (en) 2007-03-14 2013-06-25 Solvay (Societe Anonyme) Process for the manufacture of dichloropropanol
US8715568B2 (en) 2007-10-02 2014-05-06 Solvay Sa Use of compositions containing silicon for improving the corrosion resistance of vessels
US8795536B2 (en) 2008-01-31 2014-08-05 Solvay (Societe Anonyme) Process for degrading organic substances in an aqueous composition
US8507643B2 (en) 2008-04-03 2013-08-13 Solvay S.A. Composition comprising glycerol, process for obtaining same and use thereof in the manufacture of dichloropropanol
US8536381B2 (en) 2008-09-12 2013-09-17 Solvay Sa Process for purifying hydrogen chloride
US9309209B2 (en) 2010-09-30 2016-04-12 Solvay Sa Derivative of epichlorohydrin of natural origin

Also Published As

Publication number Publication date
DE1004161B (en) 1957-03-14
FR1109353A (en) 1956-01-25

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