IUPAC-NIST Solubilities Database

IUPAC-NIST Solubility Database
NIST Standard Reference Database 106

Solubility System: Acetonitrile with Esters

Components:
   (1) Esters; C20H40O2; []  NIST Chemistry WebBook for detail
   (2) Acetonitrile; C2H3N; [75-05-8]  NIST Chemistry WebBook for detail

Original Measurements:
   Schmid, H.H.O.; Mangold, H.K.; Lundberg, W.O., Microchem. J. 9, 134 (1965).

Variables:
   Temperature = 328 K to 348 K

Prepared By:
   Valerii P. Sazonov

Experimental Data:   (Notes on the Nomenclature)

Upper critical solution temperatures of the binary systems acetonitrile (1) + ester (2)
t/°C	T/K	Chemical Name
55.0	328.2	Nonadecyl methanoate; C20H40O2; [66455-49-0]
56.5	329.7	Octadecyl ethanoate; C20H40O2; [822-23-1]
61.0	334.2	Methyl nonadecanoate; C20H40O2; [1731-94-8]
64.0	337.2	Heptadecyl propanoate; C20H40O2; [66455-48-9]
65.0	338.2	Ethyl octadecanoate; C20H40O2; [111-61-5]
68.0	341.2	Hexadecyl butanoate; C20H40O2; [6221-99-4]
68.5	341.7	Propyl heptadecanoate; C20H40O2; [26718-84-3]
71.0	344.2	Butyl hexadecanoate; C20H40O2; [111-06-8]
71.5	344.7	Tetradecyl hexanoate; C20H40O2; [71801-23-5]
73.5	346.7	Dodecyl octanoate; C20H40O2; [20292-09-5]
74.0	347.2	Hexyl tetradecanoate; C20H40O2; [42231-99-2]
75.0	348.2	Octyl dodecanoate; C20H40O2; [5303-24-2]
75.0	348.2	Decyl decanoate; C20H40O2 [1654-86-0]

Method/Apparatus/Procedure:
   The synthetic method was used. A Reichert microscope, type RCH, equipped with a heating stage was used as described elsewhere.¹ The disappearance and reappearance of the interface between (1) and (2) could be observed without difficulty.

Source and Purity of Materials:
   (1) Baker Chemical Co.; reagent, No. 9011; n(20 °C, D) = 1.3445, d(20 °C, 4 °C) = 0.780.
   (2) Methyl, ethyl and butyl esters purchased from Applied Science Laboratories; propyl and hexyl esters, formate, acetate, propanoate and butyrate prepared by direct esterification; other esters synthesized by transesterification; purified.

Estimated Errors:

   Temperature: ± 0.5 K.

References:
   1. H. H. O. Schmid, H. K. Mangold, and W. O. Lundberg, J. Am. Oil Chem. Soc. 42, 372 (1965).