A reactive distillation process to produce 5-hydroxy-2-methyl-1,3-dioxane from mixed glycerol acetal isomers

Xi Hong, Omar McGiveron, Carl T. Lira, Alvaro Orjuela, Lars Peereboom, Dennis J. Miller

Research output: Contribution to journalArticle

  • 4 Citations

Abstract

The four cyclic glycerol acetal isomers can be readily produced via the acid-catalyzed reaction of glycerol with acetaldehyde or a related acetal species. In the presence of the acid catalyst used in acetal formation, the isomers interconvert to form an equilibrated mixture that contains similar quantities of the four products. Vacuum distillation can separate the four acetals into their purified forms, with the cis-5-hydroxy-2-methyl-1,3-dioxane (1) as the most volatile. When the distillation is carried out in the presence of an acid catalyst to promote interconversion, 1 is obtained as a nearly pure distillate stream. This is further adapted to a continuous reactive distillation which produced 90-96% 1. Thus a novel process is presented to convert glycerol to the desired acetal (1), which can be further converted to products such as 1,3-propanediol and dihydroxyacetone.

LanguageEnglish (US)
Pages1141-1145
Number of pages5
JournalOrganic Process Research and Development
Volume16
Issue number5
DOIs
StatePublished - May 18 2012

Profile

acetals
Acetals
distillation
glycerols
Distillation
Isomers
Glycerol
isomers
acids
Acids
Dihydroxyacetone
catalysts
Catalysts
Acetaldehyde
acetaldehyde
products
1,4-dioxane
Vacuum
vacuum

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

A reactive distillation process to produce 5-hydroxy-2-methyl-1,3-dioxane from mixed glycerol acetal isomers. / Hong, Xi; McGiveron, Omar; Lira, Carl T.; Orjuela, Alvaro; Peereboom, Lars; Miller, Dennis J.

In: Organic Process Research and Development, Vol. 16, No. 5, 18.05.2012, p. 1141-1145.

Research output: Contribution to journalArticle

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abstract = "The four cyclic glycerol acetal isomers can be readily produced via the acid-catalyzed reaction of glycerol with acetaldehyde or a related acetal species. In the presence of the acid catalyst used in acetal formation, the isomers interconvert to form an equilibrated mixture that contains similar quantities of the four products. Vacuum distillation can separate the four acetals into their purified forms, with the cis-5-hydroxy-2-methyl-1,3-dioxane (1) as the most volatile. When the distillation is carried out in the presence of an acid catalyst to promote interconversion, 1 is obtained as a nearly pure distillate stream. This is further adapted to a continuous reactive distillation which produced 90-96{\%} 1. Thus a novel process is presented to convert glycerol to the desired acetal (1), which can be further converted to products such as 1,3-propanediol and dihydroxyacetone.",
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AU - Peereboom,Lars

AU - Miller,Dennis J.

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AB - The four cyclic glycerol acetal isomers can be readily produced via the acid-catalyzed reaction of glycerol with acetaldehyde or a related acetal species. In the presence of the acid catalyst used in acetal formation, the isomers interconvert to form an equilibrated mixture that contains similar quantities of the four products. Vacuum distillation can separate the four acetals into their purified forms, with the cis-5-hydroxy-2-methyl-1,3-dioxane (1) as the most volatile. When the distillation is carried out in the presence of an acid catalyst to promote interconversion, 1 is obtained as a nearly pure distillate stream. This is further adapted to a continuous reactive distillation which produced 90-96% 1. Thus a novel process is presented to convert glycerol to the desired acetal (1), which can be further converted to products such as 1,3-propanediol and dihydroxyacetone.

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