Epoxidation of glycerol and derivatives therefrom

Abstract

A method producing a surfactant from glycerol by converting glycerol, in a first step, to glycidol, polymerizing glycidol to an aliphatic alcohol and finally substituting a hydroxyl group with a substitute anion.

1 . A method of producing a surfactant from glycerol which includes the steps of:
 (a) converting glycerol to glycidol;   (b) polymerizing glycidol to produce an aliphatic alcohol with a molecular formula C n H (2n+2) Oy, wherein n and y are numerical integers with n in the range 3 to 30 and y=n−1; and   (c) substituting the hydroxyl moiety of the alcohol with a suitable head group.   
     
     
         2 . The method according to  claim 1 , wherein the conversion of glycerol to glycidol includes the steps of dehydrating glycerol to acrolein (propenal), hydrogenating acrolein to allyl alcohol and epoxidizing allyl alcohol, with hydrogen peroxide, to glycidol. 
     
     
         3 . The method according to  claim 2 , wherein a zeolite based catalyst is used in the dehydration step. 
     
     
         4 . The method according to  claim 2 , wherein a hydrogenating catalyst, including a support and at least one transition metal on the support, is used in the hydrogenation step. 
     
     
         5 . The method according to  claim 4 , wherein the at least one transition metal is cadmium, silver or iron. 
     
     
         6 . The method according to  claim 2 , wherein an epoxidizing catalyst, being a titanium molecular sieve or a gold containing catalyst, is used in the epoxidizing step. 
     
     
         7 . The method according to  claim 1 , wherein polymerization, in step (b), takes place by heating glycidol, in an acidic medium, for a predetermined period, the length of which is dependent upon the number of carbon atoms (n) required in a tail group of the surfactant. 
     
     
         8 . The method according to  claim 7 , wherein the polymerization step is initiated with boron trifluoride. 
     
     
         9 . The method according to  claim 7 , wherein the tail group has a length in a range n=10 to 20. 
     
     
         10 . The method according to  claim 1 , wherein the head group is an anionic moiety. 
     
     
         11 . The method according to  claim 10 , wherein the anionic moiety is any one of the following: a carboxylate; a sulphate; a sulphonate; or a phosphate; or a salt thereof. 
     
     
         12 . The method according to  claim 1 , wherein the head group is a non-ionic moiety. 
     
     
         13 . The method according to  claim 7 , wherein the non-ionic moiety is urea, MEA, an amide or an imide. 
     
     
         14 . The method according to  claim 13 , wherein the urea moiety is substituted for the hydroxyl moiety in step (c) by heating the alcohol in the presence of an equimolar amount of urea. 
     
     
         15 . A method of producing glycidol from glycerol which includes the steps of:
 a) dehydrating glycerol to acrolein;   b) hydrogenating the acrolein to allyl alcohol; and   c) epoxidizing the allyl alcohol with hydrogen peroxide, to glycidol.   
     
     
         16 . The method according to  claim 15 , wherein a zeolite based catalyst is used in the dehydration step. 
     
     
         17 . The method according to  claim 15 , wherein a hydrogenating catalyst, including a support and at least one transition metal on the support, is used in the hydrogenation step. 
     
     
         18 . The method according to  claim 17 , wherein the at least one transition metal is cadmium, silver or iron. 
     
     
         19 . The method according to  claim 15 , wherein an epoxidizing catalyst, being a titanium molecular seive or a gold containing catalyst, is used in the epoxidizing step. 
     
     
         20 . The method according to  claim 15 , which includes the additional step of polymerizing glycidol to produce an aliphatic alcohol by heating glycidol in an acidic medium, for a predetermined period. 
     
     
         21 . The method according to  claim 20 , wherein the polymerization step is initiated with boron trifluoride. 
     
     
         22 . The method according to  claim 20 , which includes the additional step of substituting the hydroxyl moiety on the alcohol with a head group to produce a surfactant. 
     
     
         23 . The method according to  claim 22 , wherein the predetermined period of time during which glycidol is heated is dependent upon the number of carbon atoms required in a tail group of the surfactant. 
     
     
         24 . The method according to  claim 23 , wherein the tail group of surfactant has a length in the range n=10 to 20. 
     
     
         25 . The method according to  claim 22 , wherein the head group is an anionic moiety. 
     
     
         26 . The method according to  claim 25 , wherein the anionic moiety is any one of the following: a carboxylate; a sulphate; a sulphonate; or a phosphate; or a salt thereof. 
     
     
         27 . The method according to  claim 22 , wherein the head group is a non-ionic moiety. 
     
     
         28 . The method according to  claim 27 , wherein the non-ionic moiety is urea, MEA, an amide or an imide. 
     
     
         29 . The method according to  claim 28 , wherein the urea moiety is substituted for the hydroxyl moiety in step (c) by heating the alcohol in the presence of an equimolar amount of urea. 
     
     
         30 . A method of producing an explosive compound from glycerol which includes the steps of:
 (a) converting glycerol to glycidol;   (b) polymerizing glycidol (the monomer) to produce an aliphatic polyol (the polymer) with molecular formula C n H (2n+2) Oy, wherein n and y are numerical integers, with n in the range 3 to 30 and y=n−1;   (c) activating the aliphatic polyol by substituting each of the hydroxyl moieties with a suitable leaving group to form an activated intermediate; and (d) nitrating the activated intermediate to substitute each of the leaving groups with a nitrate moiety to produce the explosive compound.   
     
     
         31 . The method according to  claim 30 , wherein the aliphatic polyol is 1,2,3,4,5,6 heptanol (C 7 H 16 O 6 ). 
     
     
         32 . The method according to  claim 30 , wherein the leaving group is anyone of the following: chloride, iodide, bromide, azide (N 3   − ), thiocyanate (SON − ) or nitro (NO 2 ). 
     
     
         33 . The method according to  claim 30 , wherein the leaving group is a chloride ion and the aliphatic polyol is activated with chloride by bubbling chlorine gas through a solution of the polyol in a chlorination process. 
     
     
         34 . The method according to  claim 30 , wherein the activated intermediate is 2,3,4,5,6 pentanitroheptane. 
     
     
         35 . The method according to  claim 30 , wherein the nitration step (d) includes the addition of a nitrate salt to the activated intermediate. 
     
     
         36 . The method according to  claim 30 , wherein the explosive compound is 2,4,6 trinitroheptane.