GB819835A - Process for the production of monopentachlorophenyl ethers of trihydric alcohols or their acetals or ketals - Google Patents

Process for the production of monopentachlorophenyl ethers of trihydric alcohols or their acetals or ketals

Info

Publication number
GB819835A
GB819835A GB16143/57A GB1614357A GB819835A GB 819835 A GB819835 A GB 819835A GB 16143/57 A GB16143/57 A GB 16143/57A GB 1614357 A GB1614357 A GB 1614357A GB 819835 A GB819835 A GB 819835A
Authority
GB
United Kingdom
Prior art keywords
ether
ketal
acetal
trihydric alcohol
acid
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
GB16143/57A
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB819835A publication Critical patent/GB819835A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • C07C41/50—Preparation of compounds having groups by reactions producing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • C07C41/50—Preparation of compounds having groups by reactions producing groups
    • C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/12—Saturated ethers containing halogen
    • C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms

Landscapes

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

Abstract

Mono-pentachlorophenyl ethers of trihydric alcohols or their acetals or ketals, are prepared by reacting an acetal or ketal of a trihydric alcohol with hexachlorobenzene in the presence of an acid-binding agent and either isolating the ether of the acetal or ketal of the trihydric alcohol or hydrolysing the ether to the monopentachlorophenyl ether of the free trihydric alcohol. In a preferred form the reaction may be carried out continuously by acetalizing or ketalizing the trihydric alcohol in a known manner by heating it with an acetal or ketal of the mono-pentachlorophenyl ether obtained from the same trihydric alcohol, separating the mono-pentachlorophenyl ether of the trihydric alcohol from the acetal or ketal of the trihydric alcohol, reacting the latter with hexachlorobenzene in the presence of an acid-binding agent to give the acetal or ketal ether, heating again with the same trihydric alcohol and continuing the reactions in this manner. The acetals or ketals used may be formed from such alcohols as glycerol, trimethylol ethane, trimethylol propane or trimethylol butane using aldehydes or ketones such as formaldehyde, acetaldehyde, benzaldehyde, acetone, methyl ethyl ketone or cyclohexanone. The reaction of the acetal or ketal with hexachlorobenzene may take place in the presence of a metal hydroxide and a solvent such as benzene, toluene or xylene at the boiling point of the solvent so that the water of reaction is azeotropically distilled off. The acetal or ketal ether may be hydrolysed to the ether of the free alcohol by treating with steam in the presence of small quantities of acid. The continuous process may be carried out by heating the acetal or ketal ether with the trihydric alcohol at 120 DEG to 200 DEG C. in the presence of an acidic catalyst including highly dispersed substances such as alumina and acid forms of ion exchange resins using an inert diluent, if desired. In the examples: (1) 2,2-pentamethylene-5-ethyl-5-methylol-1,3-dioxan is heated with C6Cl6 and KOH and the resulting ketal ether hydrolysed with steam and acid to trimethylolpropane mono-pentachlorophenyl ether; (2) 2,2 - dimethyl - 5 - ethyl - 5 - pentachlorophenoxymethyl - 1,3 - dioxan is heated with trimethylol propane in the presence of H3PO4, 2,2 - dimethyl - 5 - ethyl - 5 - methylol - 1,3 - dioxan is distilled out and is reacted with C6Cl6 in the presence of NaOH and the residue is then distilled under high vacuum to give trimethylolpropane monopentachlorophenyl ether; (3) 2,2 - dimethyl - 5 - pentachlorophenoxymethyl-1,3-dioxolan is heated with glycerol in the presence of highly dispersed alumina (pH 2-3), 2,2 - dimethyl - 5 - methylol - 1,3 - dioxolan is distilled out and reacted with C6Cl6 in the presence of KOH and the residue distilled to give glycerol monopentachlorophenyl ether.
GB16143/57A 1956-05-26 1957-05-21 Process for the production of monopentachlorophenyl ethers of trihydric alcohols or their acetals or ketals Expired GB819835A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE819835X 1956-05-26

Publications (1)

Publication Number Publication Date
GB819835A true GB819835A (en) 1959-09-09

Family

ID=6735775

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16143/57A Expired GB819835A (en) 1956-05-26 1957-05-21 Process for the production of monopentachlorophenyl ethers of trihydric alcohols or their acetals or ketals

Country Status (1)

Country Link
GB (1) GB819835A (en)

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