GB816253A - Improvements relating to the production of benzaldehyde from toluene - Google Patents

Improvements relating to the production of benzaldehyde from toluene

Info

Publication number
GB816253A
GB816253A GB154757A GB154757A GB816253A GB 816253 A GB816253 A GB 816253A GB 154757 A GB154757 A GB 154757A GB 154757 A GB154757 A GB 154757A GB 816253 A GB816253 A GB 816253A
Authority
GB
United Kingdom
Prior art keywords
toluene
chlorination
benzaldehyde
chloride
benzal
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
GB154757A
Inventor
Robert W Harris
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.)
CHEMON CORP
Original Assignee
CHEMON CORP
Filing date
Publication date
Application filed by CHEMON CORP filed Critical CHEMON CORP
Publication of GB816253A publication Critical patent/GB816253A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/093Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C07C17/14Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/42Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
    • C07C45/43Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis of >CX2 groups, X being halogen

Landscapes

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

Abstract

A process for the production of benzaldehyde comprises reacting toluene at elevated temperatures in the liquid phase with chlorine until no more than about 35 per cent of the toluene has been converted to benzal chloride, distilling the reaction mass to separate the benzal chloride and hydrolysing the benzal chloride to benzaldehyde. The toluene should be dry and substantially pure, e.g. nitration grade toluene. The chlorination may be effected by bubbling chlorine into toluene or refluxing toluene in the presence of gaseous chlorine. The chlorination may take place in the presence of ultra-violet light or phosphorus trichloride. Plastic or glass reaction vessels should be used; the use of metal-containing catalysts or equipment being avoided. The hydrolysis may be effected with aqueous sulphuric acid, steam and compounds of zinc or water. In examples: toluene is chlorinated under reflux whilst exposed to ultra-violet light, until the specific gravity rises to 1-16 at room temperature. The chlorinated product is fractionated and the benzal chloride fraction is hydrolysed with steam to obtain benzaldehyde (1), and in a similar process the chlorination is discontinued when the specific gravity rises to 1.02 at room temperature (2). Other fractions obtained contain benzyl chloride and mixtures of benzyl and benzal chlorides. The benzyl chloride may be returned to the chlorination process.
GB154757A 1957-01-15 Improvements relating to the production of benzaldehyde from toluene Expired GB816253A (en)

Publications (1)

Publication Number Publication Date
GB816253A true GB816253A (en) 1959-07-08

Family

ID=1626879

Family Applications (1)

Application Number Title Priority Date Filing Date
GB154757A Expired GB816253A (en) 1957-01-15 Improvements relating to the production of benzaldehyde from toluene

Country Status (1)

Country Link
GB (1) GB816253A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3089908A (en) * 1960-09-06 1963-05-14 Pittsburgh Chemical Company Preparation of terephthalaldehyde from xylene dichloride
EP0011281A2 (en) * 1978-11-16 1980-05-28 Hoechst Aktiengesellschaft Process for the preparation of p-tert.-butyl benzaldehyde and the derivatives thereof substituted in the nucleus by halogen.
EP0045429A2 (en) * 1980-08-01 1982-02-10 Bayer Ag Process for the preparation of 4-tert. butylbenzaldehydes
US4450298A (en) * 1981-07-21 1984-05-22 Central Glass Company, Limited Vapor phase catalytic hydrolysis of benzal chloride or its halogen- or trifluoromethyl-substitute to form benzaldehyde or substitute
CN114456049A (en) * 2022-01-24 2022-05-10 连云港市工投集团利海化工有限公司 Preparation method and device of benzaldehyde

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3089908A (en) * 1960-09-06 1963-05-14 Pittsburgh Chemical Company Preparation of terephthalaldehyde from xylene dichloride
EP0011281A2 (en) * 1978-11-16 1980-05-28 Hoechst Aktiengesellschaft Process for the preparation of p-tert.-butyl benzaldehyde and the derivatives thereof substituted in the nucleus by halogen.
EP0011281A3 (en) * 1978-11-16 1980-09-03 Hoechst Aktiengesellschaft Process for the preparation of p-tert.-butyl benzaldehyde and the derivatives thereof substituted in the nucleus by halogen, p.-tert. butylbenzal bromide formed thereby as intermediate and the derivatives thereof substituted in the nucleus by halogen
US4277421A (en) * 1978-11-16 1981-07-07 Hoechst Aktiengesellschaft Process for the manufacture of para-tert.butylbenzaldehyde and its derivatives which are halogen-substituted at the nucleus
EP0045429A2 (en) * 1980-08-01 1982-02-10 Bayer Ag Process for the preparation of 4-tert. butylbenzaldehydes
EP0045429A3 (en) * 1980-08-01 1982-03-17 Bayer Ag Process for the preparation of 4-tert. butylbenzaldehydes
US4450298A (en) * 1981-07-21 1984-05-22 Central Glass Company, Limited Vapor phase catalytic hydrolysis of benzal chloride or its halogen- or trifluoromethyl-substitute to form benzaldehyde or substitute
CN114456049A (en) * 2022-01-24 2022-05-10 连云港市工投集团利海化工有限公司 Preparation method and device of benzaldehyde
CN114456049B (en) * 2022-01-24 2023-02-17 连云港市工投集团利海化工有限公司 Preparation device of benzaldehyde

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