GB369614A - Improvements in the manufacture and production of organic compounds containing nitrogen - Google Patents

Improvements in the manufacture and production of organic compounds containing nitrogen

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Publication number
GB369614A
GB369614A GB2753130A GB2753130A GB369614A GB 369614 A GB369614 A GB 369614A GB 2753130 A GB2753130 A GB 2753130A GB 2753130 A GB2753130 A GB 2753130A GB 369614 A GB369614 A GB 369614A
Authority
GB
United Kingdom
Prior art keywords
esters
sulphuric
acid
alcohol
ester
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
GB2753130A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB2753130A priority Critical patent/GB369614A/en
Publication of GB369614A publication Critical patent/GB369614A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/18Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings

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

Abstract

To effect alkylation of ammonia bases, at least two molecules of the latter are reacted with one molecule of neutral or acid esters of oxygen bearing, preferably polybasic mineral acids with aliphatic alcohols containing more than five carbon atoms. If salts of the acid esters are employed one molecule or more of the ammonia bases may be used for each molecule of the esters. The products are stated to be emulsifying agents. Suitable mineral acid esters are sulphuric esters of aliphatic primary, secondary or tertiary alcohols, such as hexyl alcohol, ethylpropyl carbinol, dimethyl-isobutylcarbinol, decanol, dodecanol, pentadecanol, cetyl alcohol, heptadecanol, octodecyl alcohol, 9 : 10-octodecene-1-ol, octodecandioll, sorbitol, alcohols obtained by the oxidation of paraffin wax or by the reduction of aliphatic carboxylic acids or their esters, such as tallow, olive oil, soya bean oil, train oil, castor oil, or coconut oil or other animal or vegetable fats and oils. The sulphuric esters obtained from any hydroxy containing aliphatic compound, e.g. hydroxystearic acid, ricinoleic acid, tetradecyldihydroxypropylether or from unsaturated aliphatic compounds, e.g. hexylene, octodecylene, oleic acid or its esters or amides may also be employed. In place of the sulphuric esters, esters of boric, phosphoric or sulphurous acids may be used. Suitable ammonia bases, besides ammonia, are methylamine, ethylamine, butylamine, hexylamine, diethylamine, trimethylamine, tributylamine, ethylenediamine or cycloaliphatic amines, aniline, mono- or di-methylaniline, naphthylamine, benzylamine, aminoanthraquinone, piperidine, pyridine, quinoline, and pyrrol. Amines which contain hydroxyl, halogen, nitro, ester, ether or other groups attached to a carbon atom, e.g. ethanolamines, propanolamines or other mono-, di- or tri-alkylolamines are also suitable. Unless a very large excess of base is used, more than one aliphatic residue is introduced into the base. In examples: (1) the sulphuric ester of crude dodecyl alcohol is heated in an autoclave with aqueous ammonia; (2) the sodium or ammonium salt of the sulphuric ester of octodecyl alcohol is heated with aqueous ammonia, methylamine, mono- or tri-ethanolamine or 1 : 3-propanolamine; (3) the alcohols obtained by the catalytic reduction of coco fat are esterified by means of phosphorus oxychloride and then treated with cyclohexylamine; (4) the same mixture of alcohols are sulphonated with chlorsulphonic acid, and the resulting esters, either as such or in the form of their sodium salts are treated with dimethylaniline, crude monoethanolamine, hexamethylenetetramine, di- or tri-methylamine and with tetraethylammoniumchloride; when the latter is used the reaction is effected in the presence of p aqueous caustic soda; (5) the sodium salt of olein alcohol sulphuric ester is treated with dimethylamine; (6) n-butylamine is alkylated by means of the sodium salt of the disulphuric ester of octodecandiol and of sorbitol sulphuric ester.ALSO:To effect alkylation of ammonia bases, at least two molecules of the latter are reacted with one molecule of neutral or acid esters of oxygen bearing, preferably polybasic mineral acids with aliphatic alcohols containing more than five carbon atoms. If salts of the acid esters are employed one molecule or more of the ammonia bases may be used for each molecule of the esters. The products are stated to be wetting, cleansing and emulsifying agents, and also intermediates for dyes and pharmaceutical products. Suitable mineral acid esters are sulphuric esters of aliphatic primary, secondary, or tertiary alcohols, such as hexyl alcohol, ethylpropyl carbinol, dimethyl-isobutylcarbinol, decanol, dodecanol, pentadecanol, cetyl alcohol, heptadecanol, octodecyl alcohol, 9 : 10-octodecene-1-ol, octodecandiol, sorbitol, alcohols obtained by the oxidation of paraffin wax or by the reduction of aliphatic carboxylic acids or their esters such as tallow, olive oil, soya bean oil, train oil, castor oil, or coco nut oil or other animal or vegetable fats and oils. The sulphuric esters obtained from any hydroxy containing aliphatic compound, e.g. hydroxystearic acid, ricinoleic acid, tetradecyldihydroxypropylether (obtained from tetradecylalcoholate and glycerol-a -chlorhydrin) or from unsaturated aliphatic compounds, e.g. hexylene, octodecylene, oleic acid or its esters or amides may also be employed. In place of the sulphuric esters, esters of boric, phosphoric or sulphurous acids may be used. Suitable ammonia bases, besides ammonia, are methylamine, ethylamine, butylamine, hexylamine, diethylamine, trimethylamine tributylamine, ethylenediamine or cycloaliphatic amines, aniline, mono- or di-methylaniline, naphthylamine, benzylamine, aminoanthraquinone, piperidine, pyridine, quinoline and pyrrol. Amines which contain hydroxyl, halogen, nitro, ester, ether, or other groups attached to a carbon atom, e.g. ethanolamines, propanolamines or other mono-, di- or tri-alkylolamines, are also suitable. Diluents, e.g. water, ethyl alcohol, benzene, dibutylether, xylene or nitrobenzene and copper containing catalysts, e.g. copper, copper alloys or salts, may be used for the reaction. Unless a very large excess of base is used, more than one aliphatic residue is introduced into the base. In examples: (1) the sulphuric ester of crude dodecyl alcohol, obtained by means of chlorsulphonic acid, is heated in an autoclave with aqueous ammonia: (2) the sodium or ammonium salt of the sulphuric ester of octodecyl alcohol is heated with aqueous ammonia, methylamine, mono- or triethanolamine or 1 : 3-propanolamine; (3) the alcohols obtained by the catalytic reduction of cocofat are esterified by means of phosphorus oxychloride and then treated with cyclohexylamine; (4) the same alcohols are sulphonated with chlorsulphonic acid, and the resulting esters, either as such or in the form of their sodium salts, are treated with dimethylaniline, crude monoethanolamine, hexamethylenetetramine, di- or tri-methylamine and with tetraethylammoniumchloride; when the latter is used the reaction is effected in the presence of aqueous caustic soda; (5) the sodium salt of olein alcohol sulphuric ester, obtained by sulphonation with chlorsulphonic acid in presence of ether is treated with dimethylamine; (6) butylamine is alkylated by means of the sodium salts of the disulphuric ester of octodecandiol, obtained by treatment with chlorsulphonic acid in the presence of ether, and of sorbitol sulphuric ester, obtained by sulphonation with oleum. Specifications 267,132, 278,982, 306,116, [all in Class 2 (iii), Dyes &c.], and 350,080 are referred to.
GB2753130A 1930-09-15 1930-09-15 Improvements in the manufacture and production of organic compounds containing nitrogen Expired GB369614A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2753130A GB369614A (en) 1930-09-15 1930-09-15 Improvements in the manufacture and production of organic compounds containing nitrogen

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2753130A GB369614A (en) 1930-09-15 1930-09-15 Improvements in the manufacture and production of organic compounds containing nitrogen

Publications (1)

Publication Number Publication Date
GB369614A true GB369614A (en) 1932-03-15

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
GB2753130A Expired GB369614A (en) 1930-09-15 1930-09-15 Improvements in the manufacture and production of organic compounds containing nitrogen

Country Status (1)

Country Link
GB (1) GB369614A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5993842A (en) * 1994-12-12 1999-11-30 Zeneca Limited Microcapsules containing suspensions of biologically active compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5993842A (en) * 1994-12-12 1999-11-30 Zeneca Limited Microcapsules containing suspensions of biologically active compounds

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