GB267954A - Manufacture of unsaturated aldehydes - Google Patents

Manufacture of unsaturated aldehydes

Info

Publication number
GB267954A
GB267954A GB7460/27A GB746027A GB267954A GB 267954 A GB267954 A GB 267954A GB 7460/27 A GB7460/27 A GB 7460/27A GB 746027 A GB746027 A GB 746027A GB 267954 A GB267954 A GB 267954A
Authority
GB
United Kingdom
Prior art keywords
acetaldehyde
acid
acetylene
cyclohexylidene
methyl
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
GB7460/27A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of GB267954A publication Critical patent/GB267954A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
    • 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
    • C07C45/511—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 involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/512—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 involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group

Landscapes

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

Abstract

267,954. Rupe, H. March 22, 1926, [Convention date]. Unsaturated aldehydes are obtained by treating with acid or an acid derivative an acetylene alcohol which contains a free hydrogen atom in the acetylene group and in which the hydroxyl group is attached to a carbon atom next but one to that to which the free hydrogen atom is attached. The acetylene alcohols may be cyclic, aliphatic or aromatic-aliphatic, whilst the acid may be, for example, formic acid, acetic acid, hydrochloric acid, sulphuric acid, or acetic anhydride. The products are useful for the manufacture of pharmaceutical preparations and perfumes. An example is given of the preparation of cyclohexylidene-acetaldehyde by heating 1-ethinylcyclohexanol-(1) with formic acid. In similar manner, #-methylcinnamic aldehyde can be obtained from ethylmethylphenylcarbinol, isopropylidene-acetaldehyde from ethinyldimethylcarbinol, sec-butylidene-acetaldehyde from ethinylmethylethylcarbinol, 3-methycyclohexylidene-acetaldehyde from 1-ethinyl-3-methylcyclohexanol-(1), and 2-methyl- 5-isopropyl-cyclohexylidene-acetaldehyde from 1- ethinyl-2-methyl-5-isopropyl-cyclohexanol-(1). The acetylene alcohols used as starting materials may be made by the action of acetylene on the sodium compound of a ketone. The semicarbazones of cyclohexylidene-acetaldehyde, 3-methylcyclohexylidene-acetaldehyde, 2-methyl-5-isopropylcyclohexylidene-acetaldehyde, isopropylidene-acetaldehyde, and sec-butylideneacetaldehyde are described. The oxime and bisulphite compound of cyclobexylidene-acetaldehyde are mentioned.
GB7460/27A 1926-03-22 1927-03-17 Manufacture of unsaturated aldehydes Expired GB267954A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH267954X 1926-03-22

Publications (1)

Publication Number Publication Date
GB267954A true GB267954A (en) 1927-06-09

Family

ID=4476685

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7460/27A Expired GB267954A (en) 1926-03-22 1927-03-17 Manufacture of unsaturated aldehydes

Country Status (1)

Country Link
GB (1) GB267954A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2544562A (en) * 1947-07-18 1951-03-06 Stanolind Oil & Gas Co Process for recovering aldehydes and ketones
US3057888A (en) * 1957-04-05 1962-10-09 Hoffmann La Roche Processes for and intermediates in the manufacture of unsaturated aldehydes and ketones
EP0360091A2 (en) * 1988-09-17 1990-03-28 BASF Aktiengesellschaft Process for the preparation of alkyl-substituted cinnamic aldehydes

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2544562A (en) * 1947-07-18 1951-03-06 Stanolind Oil & Gas Co Process for recovering aldehydes and ketones
US3057888A (en) * 1957-04-05 1962-10-09 Hoffmann La Roche Processes for and intermediates in the manufacture of unsaturated aldehydes and ketones
EP0360091A2 (en) * 1988-09-17 1990-03-28 BASF Aktiengesellschaft Process for the preparation of alkyl-substituted cinnamic aldehydes
EP0360091A3 (en) * 1988-09-17 1990-06-27 Basf Aktiengesellschaft Process for the preparation of alkyl-substituted cinnamic aldehydes
US4996365A (en) * 1988-09-17 1991-02-26 Basf Aktiengesellschaft Preparation of alkyl-substituted cinnamaldehydes

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