Methods for making 1,3-dihydroxyacetone (DHA) from glycerol
First Claim
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1. A method comprising:
- reacting glycerol with acetaldehyde or 1,1-diethoxyethane to produce 1,3-dihydroxyacetone (DHA), wherein the method comprises;
with an acid catalyst, forming glycerol acetal isomers from the glycerol and acetaldehyde or 1,1diethoxyethane, wherein at least one of the glycerol acetal isomers is a cis-5-hydroxy-2-methyl-1,3-dioxane isomer (cis-6 isomer);
separating the cis-6 isomer from the glycerol acetal isomers;
with an oxidation catalyst, oxidizing the cis-6 isomer to produce 2-methyl-1,3-dioxan-5-one (G-tone); and
combining the G-tone with water to produce 1,3-dihydroxyacetone (DHA), wherein the DHA is produced without using fermentation or direct oxidation of the glycerol.
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Abstract
A method comprising reacting glycerol with acetaldehyde or 1,1-diethoxyethane to produce 1,3-dihydroxyacetone (DHA), without using fermentation or direct oxidation of the glycerol is provided. DHA is useful in various products, including as a sunless tanning agent.
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Citations
28 Claims
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1. A method comprising:
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reacting glycerol with acetaldehyde or 1,1-diethoxyethane to produce 1,3-dihydroxyacetone (DHA), wherein the method comprises; with an acid catalyst, forming glycerol acetal isomers from the glycerol and acetaldehyde or 1,1diethoxyethane, wherein at least one of the glycerol acetal isomers is a cis-5-hydroxy-2-methyl-1,3-dioxane isomer (cis-6 isomer); separating the cis-6 isomer from the glycerol acetal isomers; with an oxidation catalyst, oxidizing the cis-6 isomer to produce 2-methyl-1,3-dioxan-5-one (G-tone); and combining the G-tone with water to produce 1,3-dihydroxyacetone (DHA), wherein the DHA is produced without using fermentation or direct oxidation of the glycerol. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28)
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13. A method comprising:
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combining glycerol and acetaldehyde in a first reactor to produce glycerol acetal isomers and water together with unreacted acetaldehyde; separating the glycerol acetal isomers from the unreacted acetaldehyde and water in an evaporator; distilling the glycerol acetal isomers in a vacuum distillation column with an acid catalyst;
removing cis-5-hydroxy-2-methyl-1,3-dioxane isomer (cis-6 isomer) from the vacuum distillation column;oxidizing the cis-6 isomer in a second reactor to produce 2-methyl-1,3-dioxan-5-one (G-tone); and combining the G-tone with water in a reactive distillation column to produce 1,3dihydroxyacetone (DHA). - View Dependent Claims (14, 15, 16, 17)
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Specification