Patent GB-401435-A (GB)
Title: Improvements in the manufacture and production of amino compounds
IPC: C07C209/60
Filed: 1932-07-15
Abstract: N-hydroxyalkyl aminocarboxylic acids or derivatives thereof are prepared by the action of primary or secondary amines containing at least one hydroxyalkyl group on acids containing a carboxyl group in an aliphatic chain in which a double bond is present in a , b -position to the carboxyl group; instead of the free acids, their salts or saponifiable derivatives may be used, such as their esters, nitriles, amides, imides, halides or anhydrides.  Acids p  and derivatives specified are acrylic acid and its chloride, amide, N-alkyl amides, nitrile, and alkyl esters up to the octodecyl ester; crotonic acid and its nitrile, chloride, allyl ester and N-alkylol amides; a , b -hydrosorbic acid (CH3CH2CH2CH : CHCOOH); itaconic acid; cinnamic acid; maleic acid and its anhydride or imide; fumaric acid and its diethyl ester and dinitrile.  Amines specified as suitable are mono- and di-ethanolamines; propanolamine; methylethanolamine; primary or secondary decylol-, hexadecylol-, and octodecylol-amines; 1-amino-2:3-dihydroxypropane; arylhydroxyalkyl amines such as N-ethanolaniline; and cycloalkylhydroxyalkyl amines such as N-cyclohexylbutanolamine. The products are mainly b -hydroxyalkylamino compounds containing the group -CHRCH2 CO-, where R is a hydroxyalkylamino group which may be substituted on the nitrogen atom with an alkyl, cycloalkyl, or aryl group; the corresponding a -hydroxyalkylamino compounds are obtained in subordinate amount.  The reaction may be effected at a temperature up to 200 DEG  C. in the presence or absence of a condensing agent, such as a strong acid or acid salt, and (or) an inert solvent; a number of solvents are specified.  A substance which prevents polymerization of the starting material, such as copper powder or a copper salt, may also be added. According to the conditions, the products may be the free hydroxyalkylamino acids or their salts, or derivatives corresponding to the derivatives used as starting materials, or the hydro y-alkylamides of the acids; in the last two cases, the acids or salts may be obtained by saponification.  The products may be converted into salts or amides with organic or inorganic acids, or esterified, e.g. with acetic, oleic or stearic acid or acid anhydrides or halides such as benzoyl chloride, or etherified, e.g., with alkyl halides, alkylene oxides, or alkylene halogenhydrins; if the products contain the NH group they may be alkylated or hydroxyalkylated in known manner.  The products are useful as solvents or softening agents for nitrocellulose and other lacquer materials.  In the examples, (1) ethyl acrylate is treated with with monopropanolamine to produce the compound OHC3H6NHCH2CH2COOC2H5; the product may be saponified or alkylated or esterified, as described above; (2) diethyl fumarate is treated with monoethanolamine, yielding the diethyl ester of N-hydroxyethyl aminosuccinic acid; (3) allyl crotonate is treated with monoethanolamine to produce the compound OHC2H4NHCH(CH3)CH2COOCH2CH : CH2; (4) acrylic nitrile is treated with diethanolamine to produce the compound (OHC2H4)2NCH2 CH2CN; the product may be saponified to give the corresponding acid, or subjected to catalytic hydrogenation to produce the corresponding diamine; (5) acrylic nitrile is treated with monoethanolamine to produce the compound OHC2H4NHCH2CH2CN; (6) crotonic acid or crotonic chloride is treated with monoethanolamine to produce the amide OHC2H4 NHCH(CH3) CH2 CONHC2 H4OH, which is saponified to produce the acid; (7) ethyl acrylate is treated with cyclohexylethanolamine to produce the compound C6H11N(C2H4 OH)CH2CH2COOC2H5.  Specifications 306,116, 337,737, and 337,774, [all in Class 2 (iii), Dyes &c.], are referred to.