Polyglycerol Monoether and Process for Producing the Same

Abstract

A polyglycerol monoether is represented by following General Formula (1): RO—(C 3 H 6 O 2 ) n —H   (1) wherein R represents an alcohol residue having one to thirty carbon atoms; and “n” is an average number of moles of added glycerol units and represents a number of 2 or more, and has a content (peak area percentage) of monoether components of 75% or more and a content (peak area percentage) of diether components of 5% or less, as determined by reversed-phase partition high-performance liquid chromatography using a 80:20 (by volume) mixture of methanol and water as an eluent. The polyglycerol monoether may be prepared by adding a basic substance to an alcohol to yield an alkoxide, adding glycidol to the alkoxide, and subjecting them to a reaction at 0° C. to 100° C.

1 . A polyglycerol monoether represented by following General Formula (1):
   RO—(C 3 H 6 O 2 ) n —H  (1)   wherein R represents an alcohol residue having one to thirty carbon atoms; and “n” is an average number of moles of added glycerol units and represents a number of 2 or more,
 wherein the polyglycerol monoether has a content (peak area percentage) of monoether components of 75% or more and a content (peak area percentage) of diether components of 5% or less, as determined by reversed-phase partition high-performance liquid chromatography using a 80:20 (by volume) mixture of methanol and water as an eluent. 
   
   
   
       2 . The polyglycerol monoether according to  claim 1 , wherein the polyglycerol monoether has a content (peak area percentage) of polyglycerol components of 20% or less, as determined by reversed-phase partition high-performance liquid chromatography using a 80:20 (by volume) mixture of methanol and water as an eluent. 
   
   
       3 . A process for producing a polyglycerol monoether represented by following General Formula (1):
   RO—(C 3 H 6 O 2 ) n —H  (1)   wherein R represents an alcohol residue having one to thirty carbon atoms; and “n” is an average number of moles of added glycerol units and represents a number of 2 or more,   the process comprising the steps of adding a basic substance to an alcohol to yield an alkoxide; adding glycidol to the alkoxide; and subjecting them to a reaction at 0° C. to 100° C.   
   
   
       4 . The process for producing a polyglycerol monoether according to  claim 3 , further comprising carrying out the reaction between the alkoxide and glycidol at a temperature of 30° C. to 90° C. 
   
   
       5 . The process for producing a polyglycerol monoether according to one of  claims 3  or  4 , further comprising using an alcohol having one to thirty carbon atoms as the alcohol. 
   
   
       6 . The process for producing a polyglycerol monoether according to  claim 3 , further comprising using at least one selected from the group consisting of allyl alcohol, lauryl alcohol, stearyl alcohol, sterols, tocols, and 2-ethylhexanol as the alcohol. 
   
   
       7 . The process for producing a polyglycerol monoether according to  claim 3 , further comprising using 0.1 to 40 moles of glycidol per 1 mole of the alcohol. 
   
   
       8 . The process for producing a polyglycerol monoether according to  claim 3 , further comprising using, as the basic substance, at least one selected from the group consisting of lithium, sodium, potassium, and basic compounds containing them in an amount of 0.05 to 1.00 mole per 1 mole of the alcohol.