Patent GB-802325-A (GB)
Title: Improvements in or relating to alkyl polyglyceryl ether compounds
IPC: C07C43/00
Filed: 1955-06-14
Abstract: Detergent compositions contain a mixture of alkyl and/or alkenyl polyglyceryl ether derivatives of the formula ROZnH, where R is an alkyl or alkenyl radical of 8-22 carbon atoms, Z is at least one of the groups <FORM:0802325/III/1> and <FORM:0802325/III/2> (where M is a soluble sulphonate, chlorine or hydroxy substituent) and n is 1, 2, 3 or 4, the mixture containing at least 10 mol. per cent of said compounds where n is 2 and at least one of the M groups is soluble sulphonate, for example those in which the cation is sodium, potassium, ammonium, calcium, magnesium and alkylolammonium (the alkylol group containing 2 or 3 carbon atoms), and also at most 10 mol. per cent of compounds where, whatever the value of n, M is chlorine and/or hydroxy.  Alcohols referred to from which the ethers are derived are those derived from tallow, from coconut oil, from palm oil and from hardened marine oil, and also alcohols obtained by the oxo-process an dodecyl alcohol.  Specification 421,527 is referred to.ALSO:The invention comprises a mixture of alkyl and/or alkenyl polyglyceryl ether derivatives of the formula ROZnH, where R is an alkyl or alkenyl radical of 8-22 carbon atoms, Z is at least one of the groups <FORM:0802325/IV (b)/1> and <FORM:0802325/IV (b)/2> (where M is a soluble sulphonate, chlorine or hydroxy substituent) and n is 1, 2, 3 or 4, the mixture containing at least 10 mol. per cent of said compounds where n is 2 and at least one of the M groups is soluble sulphonate, and at most 10 mol. per cent of compounds where, whatever the value of n, M is chlorine and/or hydroxy; and their preparation by separately heating a solution of sodium or potassium sulphite, preferably containing 50 to 60 per cent by weight of water, and a mixture of alkyl- and/or alkenyl-chloroglyceryl ethers, prepared by reacting 100 moles of the alcohols ROH with at least 105 mols. of epichlorhydrin, each to about 350-370 DEG  F., passing the heated materials through a comingling zone and then through a reaction zone of such size that the passage of the comingled stream requires 4-20 minutes, the temperature being 350-415 DEG  F., and recycling a minor portion of the stream leaving the reaction zone to the comingling zone, the major portion being released from the reaction pressure to a lower pressure in a receiving zone.  This process is preferably worked as a continuous synthesis of sulphonate compounds.  The cation in the sulphonate radical of the final products may be sodium, potassium, ammonium, calcium, magnesium or alkylol-ammonium (the alkylol group containing 2 or 3 carbon atoms), the last four of these being prepared by passing a solution of the sodium compounds over an ion-exchange resin to exchange Na for H and then neutralizing the acid with ammonium, alkylol-ammonium, calcium or magnesium compounds, e.g. hydroxides or carbonates.  A graph shows the relations between the amount of epichlorhydrin used in the first stage and the products obtained, above 10 per cent of chlorodiglyceryl ether existing at about 5 per cent excess of epichlorhydrin and about 7 1/2 per cent of alcohol being unreacted at this point.  An apparatus suitable for use in the process of the invention, which is advantageously conducted at a pH of 8 to 10 maintained by feeding caustic soda solution to the comingling zone, is described with the aid of a drawing.  In an example dodecyl alcohol is reacted with an 80 per cent molar excess of epichlorhydrin in the presence of stannic chloride catalyst, the resulting ether mixture is washed and distilled and the alkyl dichlorodiglyceryl ethers of dodecanol boiling at 190 DEG  C. at 1 mm. so obtained are heated at 375 DEG  F. with aqueous potassium sulphite to give a product containing 0.11 per cent of organic chlorine and 11.08 per cent of organically combined SO3.  Further procedures describe the preparation of chloroglyceryl ethers from the C12 cut produced in fractionally distilling the alcohols made by the sodium reduction of coconut oil.  Other alcohols from which the ethers may be derived referred to are those made from tallow, those from the middle cut of coconut fatty alcohols in general, those from palm oil and hardened marine oil and alcohols obtained by the oxo process.  Specification 421,527 is referred to.