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GB417072A - Improvements in or relating to the manufacture of vanillin and its homologues and other parahydroxy aldehydes such as protocatechuic aldehyde - Google Patents

Improvements in or relating to the manufacture of vanillin and its homologues and other parahydroxy aldehydes such as protocatechuic aldehyde

Info

Publication number
GB417072A
GB417072A GB1083033A GB1083033A GB417072A GB 417072 A GB417072 A GB 417072A GB 1083033 A GB1083033 A GB 1083033A GB 1083033 A GB1083033 A GB 1083033A GB 417072 A GB417072 A GB 417072A
Authority
GB
United Kingdom
Prior art keywords
azobenzene
eugenol
nitrobenzene
vanillin
homologue
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
GB1083033A
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.)
MICHAEL FRANCIS CARROLL
A Boake Roberts and Co Ltd
Original Assignee
MICHAEL FRANCIS CARROLL
A Boake Roberts and 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 MICHAEL FRANCIS CARROLL, A Boake Roberts and Co Ltd filed Critical MICHAEL FRANCIS CARROLL
Priority to GB1083033A priority Critical patent/GB417072A/en
Publication of GB417072A publication Critical patent/GB417072A/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
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties

Landscapes

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

Abstract

Vanillin or its homologues or protocatechuic aldehyde or other p-hydroxyaldehydes are manufactured by oxidation of iso-eugenol or the equivalent body parent to the aldehyde to be produced, by means of a nitro-compound in the presence of caustic alkali and in the presence of azobenzene or a homologue thereof, e.g. p-azotoluene, as solvent. The isoeugenol or equivalent body is advantageously first produced from eugenol or its equivalent by isomerization in the presence of caustic alkali and in the presence of azobenzene or a homologue thereof. In an example, eugenol (or clove oil) is heated to 190--200 DEG C. with caustic potash, water and azobenzene, the mixture is cooled to 120 DEG C., caustic soda solution is added and nitrobenzene is then run in slowly. Water is then added, unchanged nitrobenzene removed azobenzene filtered off and used in subsequent batches and vanillin isolated from the product. Isoeugenol obtained by isomerization of eugenol otherwise than in the presence of azobenzene, or by any other means, may be employed as starting material, in which case azobenzene is added before the caustic soda and nitrobenzene. In some cases, e.g. in the oxidation of 1-hydroxy-2-ethoxymethoxy-4-propenylbenzene, some azoxybenzene is produced in addition to azobenzene, in which case the mixture may be used as solvent for subsequent batches or the azoxybenzene may first be reduced to azobenzene by means of iron powder or other suitable reducing agent. If the nitrobenzene be replaced by p-nitrotoluene or a homologue thereof or other nitro-body the resulting azotoluene or other azo-body may be used in subsequent batches. Specifications 271,818, 271,819, and 285,451, [all in Class 2 (iii)], are referred to.
GB1083033A 1933-04-11 1933-04-11 Improvements in or relating to the manufacture of vanillin and its homologues and other parahydroxy aldehydes such as protocatechuic aldehyde Expired GB417072A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1083033A GB417072A (en) 1933-04-11 1933-04-11 Improvements in or relating to the manufacture of vanillin and its homologues and other parahydroxy aldehydes such as protocatechuic aldehyde

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1083033A GB417072A (en) 1933-04-11 1933-04-11 Improvements in or relating to the manufacture of vanillin and its homologues and other parahydroxy aldehydes such as protocatechuic aldehyde

Publications (1)

Publication Number Publication Date
GB417072A true GB417072A (en) 1934-09-27

Family

ID=9975089

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1083033A Expired GB417072A (en) 1933-04-11 1933-04-11 Improvements in or relating to the manufacture of vanillin and its homologues and other parahydroxy aldehydes such as protocatechuic aldehyde

Country Status (1)

Country Link
GB (1) GB417072A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103483163A (en) * 2012-06-13 2014-01-01 龙海市贝特利生物科技有限公司 New process for directly isomerizing clove leaf oil into isoeugenol

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103483163A (en) * 2012-06-13 2014-01-01 龙海市贝特利生物科技有限公司 New process for directly isomerizing clove leaf oil into isoeugenol
CN103483163B (en) * 2012-06-13 2015-12-16 龙海市贝特利生物科技有限公司 A kind of novel process being directly isomerizated into isoeugenol by clove leaf oil

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