GB494768A - Aromatic polyether chlorides - Google Patents

Aromatic polyether chlorides

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Publication number
GB494768A
GB494768A GB12671/37A GB1267137A GB494768A GB 494768 A GB494768 A GB 494768A GB 12671/37 A GB12671/37 A GB 12671/37A GB 1267137 A GB1267137 A GB 1267137A GB 494768 A GB494768 A GB 494768A
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GB
United Kingdom
Prior art keywords
phenol
condensed
ether
dichlorodiethyl ether
phenols
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
GB12671/37A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
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 Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB494768A publication Critical patent/GB494768A/en
Expired legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

b -Chloroalkoxyalkyl ethers of monoyhdric phenols substituted in the nucleus with an aliphatic hydrocarbon radicle of 8-18 carbon atoms are prepared by reacting the phenols with a b , b 1-dichlorodialkyl ether in the resence of a concentrated aqueous solution of an alkali-metal hydroxide. Specified phenols are straight or branchedchain octyl-, decyl-, dodecyl-, hexadecyl-, oleyl- or octadecylphenols; the correspondingly substituted cresols or xylenols may also be used, and other nuclear substituents, e.g. a chlorine atom or a nitro or alkoxy group, may also be present. The ethers used are of the type XCH2 CHROCHRCH2X, where X is chlorine and R is hydrogen or a methyl, ethyl, propyl, butyl, amyl or other alkyl group. In the examples, (1) p-(a , a , g , g -tetramethylbutyl) phenol is condensed with b , b 1-dichlorodiisopropyl ether or (example 2) with b , b 1-dichlorodiethyl ether; (3) o-methyl-p-a , a , g , g -tetramethylbutyl) phenol or (example 4) o-chloro-p-(a , a , g , g -tetramethylbutyl) phenol, or (example 5) caprylphenol or (example 6) laurylphenol or (example 7) cetylphenol or (example 8) stearylphenol is condensed with b , b 1-dichlorodiethyl ether; (9) a higher alcohol fraction, obtained from the reaction of hydrogen with carbon monoxide, is condensed with phenol in the presence of zinc chloride, and the product is treated with b , b 1-dichlorodiethyl ether; (10) undecylphenol is treated with b , b 1-dichlorodiethyl ether. The products may be converted into emulsifying agents by sulphonation of the benzene ring or by replacement of the terminal chlorine atom by a hydrophilic group. Specifications 494,766 and 494,769 are referred to.ALSO:b -Chloroalkoxyalkyl ethers of monohydric phenols substituted in the nucleus with an aliphatic hydrocarbon radicle of 8-18 carbon atoms are prepared by reacting the phenols with a b , b 1-dichlorodialkyl ether in the presence of a concentrated aqueous solution of an alkali-metal hydroxide. Preferably, one mol. of the phenol is heated with 3-4 mols. of the dichlorodialkyl ether in the presence of 1-1,5 mol. of alkali hydroxide. Specified phenols are straight or branched-chain octyldecyl-, dodecyl-, hexadecyl-, oleyl- or octadecyl-phenols; the correspondingly substituted cresols or xylenols may also be used, and other nuclear substituents, e.g. a chlorine atom or a nitro or alkoxy group, may also be present. The ethers used are of the type XCH2CHROCHRCH2X, where X is chlorine and R is hydrogen or a methyl, ethyl, propyl, butyl, amyl or other alkyl group. In the examples: (1) p-(a , a , g , g -tetramethylbutyl) phenol is condensed with b , b 1-dichlorodiisopropyl ether or (example 2) with b , b 1-dichlorodiethyl ether; (3) o-methyl-p-(a , a , g , g -tetramethylbutyl)phenol (made from o-cresol and diisobutylene in the presence of sulphuric acid) is condensed with b , b 1-dichlorodiethyl ether; (4) o-chloro-p-(a , a , g , g -tetramethylbutyl)-phenol is condensed with b , b 1-dichlorodiethyl ether; (5) sec.-octyl borate is condensed with phenol in the presence of boron fluoride, and the caprylphenol so obtained is treated with b , b 1-dichlorodiethyl ether; (6) lauryl alcohol is heated with phenol in the presence of zinc chloride, and the laurylphenol so obtained is condensed with b , b 1-dichlorodiethyl ether; (7) cetylphenol (prepared from phenol and cetyl alcohol in the presence of zinc chloride) is condensed with b , b 1-dichlorodiethyl ether; (8) stearylphenol (prepared from phenol and n-octadecanol-1 in the presence of zinc chloride) is condensed with b , b 1-dichlorodiethyl ether; (9) a higher alcohol fraction, obtained from the reaction of hydrogen with carbon monoxide, is condensed with phenol in the presence of zinc chloride, and the product is treated with b , b 1-dichlorodiethyl ether; (10) phenol and 5-ethylnonanol-2 are condensed in the presence of zinc chloride and the undecylphenol so obtained is treated with b -b 1-dichlorodiethyl ether. The products may be converted into detergents and emulsifying agents by sulphonation of the benzene ring or by replacement of the terminal chlorine atom by a hydrophilic group. Specifications 494,766 and 494,769 are referred to.
GB12671/37A 1937-02-24 1937-05-04 Aromatic polyether chlorides Expired GB494768A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US494768XA 1937-02-24 1937-02-24

Publications (1)

Publication Number Publication Date
GB494768A true GB494768A (en) 1938-11-01

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ID=21960024

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12671/37A Expired GB494768A (en) 1937-02-24 1937-05-04 Aromatic polyether chlorides

Country Status (1)

Country Link
GB (1) GB494768A (en)

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