US2010727A - Naphthenic alcohol esters of fatty acids - Google Patents

Naphthenic alcohol esters of fatty acids Download PDF

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Publication number
US2010727A
US2010727A US648725A US64872532A US2010727A US 2010727 A US2010727 A US 2010727A US 648725 A US648725 A US 648725A US 64872532 A US64872532 A US 64872532A US 2010727 A US2010727 A US 2010727A
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Prior art keywords
fatty acids
esters
alcohol esters
naphthenic
naphthenic alcohol
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Expired - Lifetime
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US648725A
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Kirstahler Alfred
Kaiser Wilhelm Jacob
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/06—Protein or carboxylic compound containing

Definitions

  • the said valuable high-molecular compounds are obtained according to the invention by converting the said esters with organic hydroxy compounds, aliphatic, hydroaromatic or aliphaticaromatic alcohols and phenols.
  • the organic hydroxy compounds are preferably employed in the form of their alkali compounds.
  • the aliphatic alcohols containing 6 or more carbon atoms and having a saturated or unsaturated nature also the naphthenic alcohols and the resin alcohols have been found to be particularly suitable.
  • the alcoholsobtainable from paraffin, also aliphatic-aromatic alcohols, such as benzyl alcohol, beta-phenyl-ethyl alcohol and the like may be employed, likewise polyvalent alcohols.
  • the lat-halogen fatty acids such as mono-chloracetic acid, monobromsuccinic acid, dichlor-acetic acid, a-bromolauric acid have been found to be particularly suitable.
  • aliphatic carboxylic acids which are substituted by halogen in other positions, furthermore carboxylic acids of other series containing replaceable halogen atoms, such as for example benzyl chloride-4-carboxylic acid, 2- chlorobenzoic acid or its substitution products, such as for example 5-sulpho-2-chlorobenzoic acid.
  • the new high-molecular compounds in so far as they are insoluble in water, should find an appllcation in the perfume industry, furthermore as softening agents or the like.
  • the water-soluble products manufactured according to the present invention possess saponaceous properties.
  • Examples (1) 23 parts by weight of sodium metal are dissolved in 600 parts by weight of phenol, and 262 parts by weight of dodecyl chloracetic. ester are added to this solution. The mixture is then heated for 8 hours at 100 C. in the absence of atmospheric moisture.
  • the dodecyl phenoxyacetic ester is obtained as a white crystalline mass.
  • Anew class of hydroaromatic esters of carboxylic acids corresponding to the formula R O-R -CO-O-R in which R denotes a radical of a group consisting of fatty acid acyl radicals and aryl radicals, R CO-O denotes a saturated fatty acid radical and R denotes a radical of naphthenic alcohol.
  • a new class of hydroaromatic esters of carboxylic acids corresponding to the formula R O-R CO-O-R in which R denotes an aryl radical, R -CO-O denotes a saturated fatty acid radical, and R denotes a radical of naphthenic alcohol.

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

Description

Patented Aug. 6, 1935 NlTE ST NAPHTHENIC ALCOHOL ESTERS F FATTY ACIDS Alfred Kirstahler, Dusseldorf, and Wilhelm Jacob Kaiser, Dusseldorf-Benrath, Germany,
signors to firm Henkel & (Die. Gesellsohaft mit beschrankter Haftung, Dusseldorf, Germany No Drawing. Application December 23, 1932, In Germany January 4,
Serial No. 648,725. 1932 2 Claims.
unsubstituted or substituted, saturated or unsaturated, aliphatic, hydroaromatic or aliphaticaromatic compounds containing hydroxyl, and having at least 6 carbon atoms, and on the other, of acids containing reactive halogen atoms or the derivatives or substitution products of such acids.
The said valuable high-molecular compounds are obtained according to the invention by converting the said esters with organic hydroxy compounds, aliphatic, hydroaromatic or aliphaticaromatic alcohols and phenols. The organic hydroxy compounds are preferably employed in the form of their alkali compounds.
Of the hydroxyl compounds which are necessary for the synthesis of the said esters, the aliphatic alcohols containing 6 or more carbon atoms and having a saturated or unsaturated nature, also the naphthenic alcohols and the resin alcohols have been found to be particularly suitable. The alcoholsobtainable from paraffin, also aliphatic-aromatic alcohols, such as benzyl alcohol, beta-phenyl-ethyl alcohol and the like may be employed, likewise polyvalent alcohols. It is also possible, however, to employ other aliphatic compounds containing hydroxyl groups, and having at least 6 carbon atoms, such as for example the saturated or unsaturated hydroxy fatty acids and their derivatives, such as esters and amines, and the hydroxyalkyl esters of fatty acids and the like, the hydroxyalkyl ethers or hydroxyalkyl thioethers of the higher alcohols and so on.
Of the acids which contain reactive halogen atoms and which are necessary for the synthesis of the said esters, the lat-halogen fatty acids, such as mono-chloracetic acid, monobromsuccinic acid, dichlor-acetic acid, a-bromolauric acid have been found to be particularly suitable. Instead of such (ii-halogen acids, however, it is also possible to employ aliphatic carboxylic acids which are substituted by halogen in other positions, furthermore carboxylic acids of other series containing replaceable halogen atoms, such as for example benzyl chloride-4-carboxylic acid, 2- chlorobenzoic acid or its substitution products, such as for example 5-sulpho-2-chlorobenzoic acid.
The new high-molecular compounds, in so far as they are insoluble in water, should find an appllcation in the perfume industry, furthermore as softening agents or the like.
The water-soluble products manufactured according to the present invention possess saponaceous properties.
They may be employed alone or together with other soaps, saponaccous substances, filling substances, compounds which give off active oxygen and the like.
Examples (1) 23 parts by weight of sodium metal are dissolved in 600 parts by weight of phenol, and 262 parts by weight of dodecyl chloracetic. ester are added to this solution. The mixture is then heated for 8 hours at 100 C. in the absence of atmospheric moisture.
After working up in the usual manner, the dodecyl phenoxyacetic ester is obtained as a white crystalline mass.
Meltin point 33-34" C. Boiling point 240-245 C. at 17 The tetradecyl and hexadecyl esters of phenoxy-acetic acid, and their mixtures, may be manufactured in a similar manner.
The same com- We claim:
1. Anew class of hydroaromatic esters of carboxylic acids corresponding to the formula R O-R -CO-O-R in which R denotes a radical of a group consisting of fatty acid acyl radicals and aryl radicals, R CO-O denotes a saturated fatty acid radical and R denotes a radical of naphthenic alcohol.
2. A new class of hydroaromatic esters of carboxylic acids corresponding to the formula R O-R CO-O-R in which R denotes an aryl radical, R -CO-O denotes a saturated fatty acid radical, and R denotes a radical of naphthenic alcohol.
ALFRED KIRSTAHLER. WILHELM JACOB KAISER.
US648725A 1932-01-04 1932-12-23 Naphthenic alcohol esters of fatty acids Expired - Lifetime US2010727A (en)

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DE2010727X 1932-01-04

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2769833A (en) * 1953-11-02 1956-11-06 Diamond Alkali Co Production of phenoxy acid esters through the potassium phenolate
US2952702A (en) * 1952-11-12 1960-09-13 Morton Chemical Co Preparation of polyhalo aryloxy acetic acid esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2952702A (en) * 1952-11-12 1960-09-13 Morton Chemical Co Preparation of polyhalo aryloxy acetic acid esters
US2769833A (en) * 1953-11-02 1956-11-06 Diamond Alkali Co Production of phenoxy acid esters through the potassium phenolate

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