Dibutyl tartrate

Dibutyl tartrate
	; Dibutyl tartrate, with no stereochemical detail
Names
	IUPAC name dibutyl 2,3-dihydroxybutanedioate
Identifiers
CAS Number	87-92-3;
3D model (JSmol)	Interactive image;
ChemSpider	190760;
ECHA InfoCard	100.001.623
EC Number	201-784-9;
PubChem CID	220014;
UNII	2D1V32IF1E;
CompTox Dashboard (EPA)	DTXSID10883265 ;
	InChI 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;
	SMILES CCCCOC(=O)C(C(C(=O)OCCCC)O)O;
Properties
Chemical formula	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)
Chiral rotation ([α]D)	+11.5
Refractive index (nD)	1.447
Hazards
Flash point	91 °C (196 °F; 364 K)
Autoignition; temperature	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).
	Infobox references

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

The dielectric constant of dibutyl tartrate is 9.4[7]

References

"Dibutyl tartrate". webbook.nist.gov.
Eeckhaut, Ann Van; Michotte, Yvette (2009). Chiral Separations by Capillary Electrophoresis. CRC Press. pp. 258–262. ISBN 978-1-4200-6934-1.
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.
Lawton, W. "Viscoelasticity of Zein-Starch Doughs". Cereal Chern. 69 (4): 351–355.
The Industrial Chemist. 20. Tothill Press. 1944. p. 98.
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.
CRC Handbook 84th edition page 6-175

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[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.

[4] Lawton, W. "Viscoelasticity of Zein-Starch Doughs". Cereal Chern. 69 (4): 351–355.

[5] The Industrial Chemist. 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