Dibutyl tartrate

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Dibutyl tartrate
Dibutyl tartrate no-chiral.png
Dibutyl tartrate, with no stereochemical detail
Names
IUPAC name
dibutyl 2,3-dihydroxybutanedioate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.623 Edit this at Wikidata
EC Number
  • 201-784-9
UNII
  • InChI=1S/C12H22O6/c1-3-5-7-17-11(15)9(13)10(14)12(16)18-8-6-4-2/h9-10,13-14H,3-8H2,1-2H3
    Key: PCYQQSKDZQTOQG-UHFFFAOYSA-N
  • CCCCOC(=O)C(C(C(=O)OCCCC)O)O
Properties
C12H22O6
Molar mass 262.302 g·mol−1
Density 1.091
Melting point 21 °C (70 °F; 294 K)
Boiling point 320 °C (608 °F; 593 K)
+11.5[clarification needed]
1.447
Hazards
Flash point 91 °C (196 °F; 364 K)
284 °C (543 °F; 557 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dibutyl tartrate is a di-ester of tartaric acid and butanol.[1] It has been used as a chiral oil to separate enantiomers in chromatography.[2][3] Another use is in farinographs.[4] Yet another use is as a plasticizer.[5] The material is classed as "green" as it is made from natural products, and is biodegradable.[6]

Properties[edit]

The dielectric constant of dibutyl tartrate is 9.4[7]

References[edit]

  1. ^ "Dibutyl tartrate". webbook.nist.gov.
  2. ^ Eeckhaut, Ann Van; Michotte, Yvette (2009). Chiral Separations by Capillary Electrophoresis. CRC Press. pp. 258–262. ISBN 978-1-4200-6934-1.
  3. ^ Kahle, Kimberly A.; Foley, Joe P. (June 2007). "Two-chiral-component microemulsion electrokinetic chromatography–chiral surfactant and chiral oil: Part 1. Dibutyl tartrate". Electrophoresis. 28 (11): 1723–1734. doi:10.1002/elps.200600551. PMID 17464962. S2CID 41187551.
  4. ^ Lawton, W. "Viscoelasticity of Zein-Starch Doughs". Cereal Chern. 69 (4): 351–355.
  5. ^ The Industrial Chemist. Vol. 20. Tothill Press. 1944. p. 98.
  6. ^ Zawada, Krzysztof; Plichta, Andrzej; Jańczewski, Dominik; Hajmowicz, Halina; Florjańczyk, Zbigniew; Stępień, Magdalena; Sobiecka, Agnieszka; Synoradzki, Ludwik (26 May 2017). "Esters of Tartaric Acid, A New Class of Potential "Double Green" Plasticizers". ACS Sustainable Chemistry & Engineering. 5 (7): 5999–6007. doi:10.1021/acssuschemeng.7b00814.
  7. ^ CRC Handbook 84th edition page 6-175