1434
J. Chem. Eng. Data 2010, 55, 1434–1436
Solubilities of N-[(4-Bromo-3,5-difluorine)phenyl]acrylamide in Benzene,
Methanol, Pyridine, Ethanol, Acetonitrile, and Toluene at
Temperatures between (284.65 and 348.95) K
Xinding Yao,† Xinbao Li,‡ Yanxun Li,† Tingliang Luo,† and Guoji Liu*,†
College of Chemical and Energy Engineering, Zhengzhou University, Zhengzhou 450001, P.R. China, and
North China Institute of Water Conservancy and Hydroelectric Power, Zhengzhou 450011, P.R. China
The solubility of N-[(4-bromo-3,5-difluorine)phenyl]acrylamide (BDPA) in pure benzene, methanol, pyridine,
ethanol, acetonitrile, and toluene was measured at temperatures ranging from (284.65 to 348.95) K under
atmospheric pressure. A laser monitoring observation technique was used to determine the dissolution of
the solid phase in solid + liquid mixture. The experimental solubility data were correlated with the modified
Apelblat equation.
Introduction
Fluorine-containing polymers are particularly attractive and
useful compounds because of their unique properties including
high thermal, chemical, aging, and weather resistance, low
Figure 1. Structure of BDPA.
dielectric constants, refractive index, surface energy, and
flammability.1,2 There are various approaches for preparing
fluorine-containing acrylate emulsion, such as synthesizing
CH), (7.26 to 7.34) (m, 2H, ArH), (7.43 to 7.44) (m, 1H, NH),
core-shell fluorine-containing polyacrylate emulsion with
high-resolution molecular masses (calcd for C9H6ONF2Br
fluorine-freeacrylateandfluorine-containingacrylatemonomers.3-5
261.9679, found 261.9676)] were obtained by filtering, washing,
N-[(4-Bromo-3,5-difluorine)phenyl]acrylamide (BDPA, Fig-
and drying.
ure 1) is a new fluorine-containing acrylate monomer for
Its mass fraction purity was more than 99.2 %, determined
polyreaction. BDPA was synthesized by the interaction of
by high-performance liquid chromatography (HPLC). The
4-bromo-3,5-difluoroaniline with acryloyl chloride in the pres-
melting point is (455.0 ( 0.3) K (measured by DSC). All of
ence of triethylamine. Crude BDPA was gained after concen-
the solvents, benzene, methanol, pyridine, ethanol, acetonitrile,
trating and filtrating. For an extensive fluorine-containing
and toluene (purchased from the Tianjin Kewei of China) used
polymer investigation, crude BDPA has to be purified by
for experiments were analytical reagent grade, and their mass
crystallization. To improve the purity and yield of BDPA, the
fraction purities were higher than 99.8 %. Distilled, deionized
solubility data of BDPA in different solvents are required.
water of HPLC grade was used throughout.
In this article, solubility measurement of BDPA in pure
benzene, methanol, pyridine, ethanol, acetonitrile, and toluene
in the temperatures ranging from (284.65 to 348.95) K were
performed at atmospheric pressure by a laser monitoring
Apparatus and Procedure. The solubility of BDPA in six
pure solvents was measured by the method that was described
in the literature.8-10 The experiments were carried out in a 50
mL jacketed glass vessel with a magnetic stirrer. The temper-
observation technique. Experimental data were correlated by
the modified Apelblat equation.6,7
ature, with an uncertainty of ( 0.05 K, was controlled by
circulating water through the outer jacket. To prevent the
evaporation of the solvent, a condenser vessel was introduced.
A laser monitoring system, which consisted of a laser generator,
a photoelectric transformer, and a light intensity display, was
used to determine the disappearance of the last crystal in the
mixtures. An electronic balance (Shimadzu AX200) with an
uncertainty of ( 0.0001 g was used for the mass measurements.
Experimental Section
Materials. The BDPA was produced in our laboratory.
Portions of 200 mL of ethyl acetate, 32.1 g of 4-bromo-3,5-
difluoroaniline, 25 g of sodium bicarbonate, and 0.5 g of ethyl
hydroxylamine were put into a 500 mL four-mouth flask,
respectively, and then 22 mL of acryloyl chloride was dropwise
added. The mixture was maintained for 10 h at the temperature
of 293.15 K, followed by 15 h of reflux. Ethyl acetate was
removed by distillation and then cooled to room temperature.
During the measurement, predetermined excess amounts of
solute and solvent of known masses were added to the jacket
vessel. The contents of the vessel were stirred continuously for
30 min at a fixed temperature. Then, additional solvent of known
mass was introduced to the cell. When the last solute just
disappeared, the laser intensity penetrating through the vessel
reached a maximum, and the solvent mass consumed in the
measure was recorded. Together with the mass of solute, the
solubility would be obtained. The saturated mole fraction
solubility of BDPA can be determined from eq 1
1
BDPA [12 g, mp (454.9 to 455.5) K, H NMR (CDCl3, 400
MHz) δ: (5.83 to 5.86) (m, 2H, CH2), (6.19 to 6.26) (m, 1H,
* Corresponding author. Phone: 86 0371 67781101. E-mail: guojiliu@
zzu.edu.cn.
† Zhengzhou University.
‡ North China Institute of Water Conservancy and Hydroelectric Power.
10.1021/je900609f 2010 American Chemical Society
Published on Web 12/15/2009
Yao, Xinding
