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.

    Original languageEnglish (US)
    Pages (from-to)1141-1145
    Number of pages5
    JournalOrganic Process Research and Development
    Volume16
    Issue number5
    DOIs
    StatePublished - May 18 2012

    Profile

    acetals
    distillation
    glycerols
    Distillation
    isomers
    acids
    Hematopoiesis
    catalysts
    products
    Afferent Loop Syndrome
    acetaldehyde
    vacuum
    Scandium
    Agglutination Tests

    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

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

    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.",
    author = "Xi Hong and Omar McGiveron and Lira, {Carl T.} and Alvaro Orjuela and Lars Peereboom and Miller, {Dennis J.}",
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    AU - McGiveron,Omar

    AU - Lira,Carl T.

    AU - Orjuela,Alvaro

    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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