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Glycerine acetate

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(Redirected from Monoacetin)
Glycerine acetate

R = H or CH3C(=O)
Names
Other names
glycerol acetate
glyceryl acetate
1,2,3-propanetriol acetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.216 Edit this at Wikidata
EC Number
  • 1-monoacetin: 247-704-6
  • 1,2-diacetin: 246-941-2
  • triacetin: 203-051-9
RTECS number
  • triacetin: AK3675000
UNII
  • 1-monoacetin: InChI=1S/C5H10O4/c1-4(7)9-3-5(8)2-6/h5-6,8H,2-3H2,1H3
    Key: KMZHZAAOEWVPSE-UHFFFAOYSA-N
  • 1,2-diacetin: InChI=1S/C7H12O5/c1-5(9)11-4-7(3-8)12-6(2)10/h7-8H,3-4H2,1-2H3
    Key: UXDDRFCJKNROTO-UHFFFAOYSA-N
  • triacetin: InChI=1S/C9H14O6/c1-6(10)13-4-9(15-8(3)12)5-14-7(2)11/h9H,4-5H2,1-3H3
    Key: URAYPUMNDPQOKB-UHFFFAOYSA-N
  • 1-monoacetin: CC(=O)OCC(CO)O
  • 1,2-diacetin: CC(=O)OCC(CO)OC(=O)C
  • triacetin: CC(=O)OCC(COC(=O)C)OC(=O)C
Properties
Variable
Molar mass Variable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Glycerine acetate is a mixture of esters produced from the esterification of glycerol (1) with acetic acid. This reaction produces five congeners:

  • the two monoacetylglycerols / MAG / monoacetin (2 and 3)
  • the two diacetylglycerols / DAG / diacetin / glyceryl diacetate (4 and 5)
  • the one triacetalglycerol / TAG / triacetin (6)
Structures of all possible acetate esters of glycerol
Structures of all possible acetate esters of glycerol

In addition, two of the congeners, 2 and 4, are chiral and can exist in either of two enantiomeric forms.

Uses

[edit]

DAG and TAG can be used as fuel additives for improving the cold and viscosity properties of biodiesel or the antiknocking properties of gasoline.[1]

Notes

[edit]
  1. ^ J. A. Melero; R. vanGrieken; G. Morales; M. Paniagua (2007). "Acidic Mesoporous Silica for the Acetylation of Glycerol: Synthesis of Bioadditives to Petrol Fuel". Energy & Fuels. 21 (3): 1782–1791. doi:10.1021/ef060647q.