Patent GB-1087413-A (GB)
Title: Improvements in or relating to amines
Inventor: KOEBNER ADOLF
IPC: C09K23/00
Filed: 1963-06-25
Abstract: Amines of the formula <FORM:1087413/C3/1> where Z is a C8- 18 alkyl or alkenyl group or an alkylphenyl group possessing an alkyl substituent having from 6 to 16 carbons, R is -(CqH2qO)xH, Z(OCpH2p)n- or C1- 4 alkyl, p is 2 or 3, q is 2 or 3, n is 2-9 and x is 1-20, provided that when Z is alkylphenyl, the amine contains at least one hydroxy-propyl or condensed hydroxypropyl group, may be obtained by reacting an organic sulphate ester of the formula Z(OCpH2p)nOSO3M, where M is a cation, with an alkylolamine of the formula <FORM:1087413/C3/2> where R1 is the same as R or a hydrogen atom, in the presence of a solvolytic medium and a base at a temperature of at least 100 DEG  C., and optionally reacting the tertiary amine product with ethylene and/or propylene oxide to increase the value of x to not more than 20.  The solvolytic medium employed in the process is a highly polar liquid which is a solvent for the organic sulphate; it is preferably an excess of the alkylolamine reactant, but an aqueous medium containing a dissolved base, e.g. a tertiary amine or an alkali metal hydroxide or carbonate, or dimethyl sulphoxide, sulpholane or C10- 20 alcohols may also be used.  The cation M in the monosulphate is preferably an alkylolammonium ion derived from the reactant alkylolamine.  The optional second stage of the process may be effected by reacting the tertiary amine product from the first stage with the required molar amount of ethylene or propylene oxide or a mixture thereof, preferably under superatmospheric pressure and generally at 50-200 DEG  C. in the presence of a catalyst, e.g. a Lewis acid or a base.ALSO:Amines of the formula <FORM:1087413/C2/1> where Z is C8- 18 alkyl or alkenyl or an alkylphenyl group possessing an alkyl substituent having from 6 to 16 carbons, R is -(CqH2qO)xH, Z(OCpH2p)n- or C1- 4 alkyl, p is 2 or 3, q is 2 or 3, n is 2 to 9, x is 1-20, provided that when Z is alkyl phenyl, the amine contains at least one hydroxy propyl or condensed hydroxypropyl group, may be obtained by reacting an organic sulphate ester of the formula Z(OCpH2p)nOSO3M, where M is a cation, with an alkylolamine of the formula <FORM:1087413/C2/2> where R1 is the same as R or a hydrogen atom, in the presence of a solvolytic medium and a base at a temperature of at least 100 DEG  C., and optionally reacting the tertiary amine product with ethylene and/or propylene oxide to increase the value of x to not more than 20.  The solvolytic medium employed in the process is a highly polar liquid which is a solvent for the organic sulphate; it is preferably an excess of the alkylolamine reactant, but an aqueous medium containing a dissolved base, e.g. a tertiary amine or an alkali metal hydroxide or carbonate, or dimethyl sulphoxide, sulpholane and C10- 20 alcohols may also be used.  The cation M in the monosulphate is preferably an alkylolammonium ion derived from the reactant alkylolamine.  The optional second stage of the process may be effected by reacting the tertiary amine product from the first stage with the required molar amount of ethylene oxide, propylene oxide or mixture thereof, preferably under superatmospheric pressure and generally at 50-200 DEG  C. in the presence of a catalyst, e.g. a Lewis acid or a base. In examples, lauryltrioxyethylene bis - (2 - hydroxy ethyl)amine, p - nonyl phenyltetraoxyethylenebis - (2 - hydroxyethyl)amine, lauryl-trioxyethylene bis-(2 - hydroxypropy)amine and lauryl - trioxypropylene bis - (2 - hydroxyethyl)amine are prepared; other compounds of the invention are also specified.