Synthesis, characterization and surface activity of alkyl m-xylene sulfonate isomers

Article abstract of DOI:10.1007/s11743-012-1358-8

This paper deals with the synthesis of a series of alkyl m-xylene sulfonate isomers (with the m-xylene located at the eighth carbon atom along the long alkyl chain) by the Friedel-Crafts reaction, and the Grignard reaction followed by hydrogenation. The structures were confirmed by ¹H NMR. All analytical methods indicated high levels of purity of the isomers with the eighth carbon atom at the long alkyl chain. The critical micelle concentration (CMC), surface tension and maximum surface excess concentration at the CMC and area per molecule at the interface were determined. As the long alkyl chains increased the surfactant molecule tends to pack closely at the gas-liquid interface. Accordingly, the CMC decreased, the adsorption density increased, and the surface tension reduction was strengthened.

Full text of DOI:10.1007/s11743-012-1358-8

J Surfact Deterg (2012) 15:631–636
DOI 10.1007/s11743-012-1358-8
ORIGINAL ARTICLE
Synthesis, Characterization and Surface Activity of Alkyl
m-Xylene Sulfonate Isomers
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Huo-xin Luan Wen-xiang Wu Jie-cheng Cheng Tao Yu Guang-miao Qu
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Ya-bin Xu Guo-qiao Li Xiao-yu Gao An-jun Li Dan-dan Yuan
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Wei Tong Zhong Li Kang Liu Guo-yu Liu Wei Ding
Received: 20 September 2011 / Accepted: 18 April 2012 / Published online: 11 May 2012
Ó AOCS 2012
Abstract This paper deals with the synthesis of a series of
alkyl m-xylene sulfonate isomers (with the m-xylene located
at the eighth carbon atom along the long alkyl chain) by the
Friedel–Crafts reaction, and the Grignard reaction followed
byhydrogenation.Thestructureswereconfirmedby1HNMR.
All analytical methods indicated high levels of purity of the
isomers with the eighth carbon atom at the long alkyl chain.
The critical micelle concentration (CMC), surface tension and
maximum surface excess concentration at the CMC and area
per molecule at the interface were determined. As the long
alkyl chains increased the surfactant molecule tends to pack
closely at the gas–liquid interface. Accordingly, the CMC
decreased, the adsorption density increased, and the surface
tension reduction was strengthened.
role in this technique. When surfactant solutions are added
to the reservoir, they can lower interfacial tension between
oil and water, change the rock wettability and solubiliza-
tion, thus contribute to EOR [3–7]. Most surfactants used
in EOR are mixtures of different compounds, such as
petroleum sulfonates and heavy alkyl benzene sulfonates,
which are mainly composed of alkyl benzene sulfonates
with different molecular weights and alkyl chain lengths.
Because of their complex components and unidentified
structures, it is difficult to elucidate the relationship
between the structures and properties. This motivates
researchers to synthesize the alkyl aryl sulfonates with
definite structures. A considerable number of investigations
have been reported on the synthesis and surface properties
of alkylbenzene sulfonate with the definite structures.
Baumgartner [8, 9] synthesized the isomers of dodecyl
benzene sulfonate with the benzene ring attached at dif-
ferent positions on the dodecyl chain for the first time. The
detergency and wetting properties were reported and rela-
ted with different structures and much work was focused
on the foaming, wetting, surface tension. Doe [10, 11] and
Wade [12] studied the interfacial tension between n-alkane
and an aqueous solution of hexadecyl benzene sulfonate
isomers with the benzene ring located from the 2nd to the
8th carbon atom, i.e., from 2-phenyl hexadecane sulfonate
to 8-phenyl hexadecane sulfonate, and they characterized
the surfactants by the concept of the preferred alkane car-
bon number (nmin) to attain minimum tension. As the
benzene ring point of attachment is shifted from the
extreme to the center of the n-hexadecane chain, the sur-
factant becomes more hydrophobic, but it is also more
water soluble, which is an apparently paradoxical associ-
ation of properties. In recent years, Yang [13, 14] and Zhao
[15] synthesized a series of the hexadecyl benzene sulfo-
nates. Zhang [16] synthesized multi-n-alkyl benzene
Keywords Alkyl m-xylene sulfonate Á Isomerization Á
Surface activity
Introduction
Chemical flooding is an important method for enhanced oil
recovery (EOR) [1, 2] and surfactants play an important
H. Luan Á W. Wu Á T. Yu Á G. Qu Á Y. Xu Á G. Li Á X. Gao Á
A. Li Á D. Yuan Á W. Tong Á Z. Li Á K. Liu Á
G. Liu Á W. Ding (&)
College of Chemistry and Chemical Engineering, Northeast
Petroleum University, Daqing 163318, China
e-mail: dingwei40@126.com
H. Luan Á W. Wu
Petroleum Development Engineering, Northeast Petroleum
University, Daqing 163318, China
J. Cheng
Daqing Oilfield Limited Company of CNPC, Daqing 163453,
China
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Scheme 1 Synthesis route of
Cx-8MXS
OH
R1CHR2
R1CHR2
R1C=O
__ C__
R1
R2MgBr H3C
R2
H3C
R1COCl
H3C
H3C
HSO3Cl
NaOH
H3C
Pd / C
H2
SO3Na
CH3
CH3
CH3
CH3
CH3
a
d
c
b
1
R1=C7H15 R2=C7H15
C15-8MXS
C16-8MXS
C17-8MXS
2
3
R1=C8H17
R1=C9H19
R2=C7H15
R2=C7H15
sulfonates and reported characteristic parameters such as
the critical micellar concentration (CMC), and the surface
and interfacial tension at CMC. Qu [17] synthesized a
series of isomers of hexadecyl o-xylene sulfonates and
reported on some of their properties. However, the syn-
thesis and surface properties of alkyl m-xylene sulfonate
isomers where the aryl located at the eighth carbon atom
along the long alkyl chain have not been reported.
Hydrogen and nitrogen were of high grade purity from
XueLong (99.99 % purity, Daqing China). 1H-NMR
spectra were obtained with the Bruker FT-300 spectrome-
ter using CDCl3 as solvent. Chemical shifts (d) were
reported in ppm related to internal tetramethylsilane. After
some optimization trials, the alkyl m-xylene sulfonate
isomers (C15-8MXS, C16-8MXS, C17-8MXS) was carried
out through the following steps [18].
In this paper we present the synthesis of a series of
isomers of alkyl m-xylene sulfonate and we report their
properties. The correct name of the sulfonate final product
in which the sulfonated aryl ring group is located at the
eighth carbon atom of long alkyl chain could be n-penta-
decane (or n-hexadecane, or n-heptadecane) 8-m-xylene
sulfonate and it is abbreviated in what follows as
Cx-8MXS. The same kind of abbreviation is used for the other
isomers, with the number ‘‘x’’ indicating the total number
of carbon atoms in the alkyl chain. The routes to attain the
synthesized compounds are illustrated in Scheme 1. The
details are discussed later in the experimental section.
Because of the steric hindrance, the acylation cannot take
place in the ortho position of one of the methyl groups of
the aryl ring; as a consequence, there is only one possible
final isomer of the alkyl m-xylene sulfonate. It means that
the only isomeric variation is due to the attachment posi-
tion of the m-xylene on the long alkyl chain.
Synthesis of Ketones
1-(2,4-Dimethyl-phenyl)-1-octanone (1a)
Octanoyl chloride (0.10 mol, 16.2 g) was added dropwise
to a stirred solution of anhydrous AlCl3 (0.13 mol, 17.36 g)
and m-xylene (0.40 mol, 42.4 g), the mixture was cooled in
an ice-water bath for 30 min and then heated at a reflux for
3 h. The mixture was then cooled and decomposed with
ice-cooled dilute hydrochloric acid (100 mL). After the
phase of separation, the upper layer was washed with a
NaHCO3 solution and deionized water until it became
neutral, and finally dried over anhydrous calcium chloride.
The excess of m-xylene was removed by distillation and
the solvent was evaporated under reduced pressure. Com-
pound 1a was obtained with a 85.31 % yield.
1-(2,4-Dimethyl-phenyl)-1-nonanone (2a)
Experimental Procedures
Nonanoyl chloride (0.10 mol, 17.6 g) was added dropwise
to a stirred solution of anhydrous AlCl3 (0.13 mol, 17.36 g)
and m-xylene (0.40 mol, 42.4 g), compound 2a was
obtained with a 83.52 % yield as yellow oil starting from
following the same procedure described for 1a.
Materials
The purity of all the chemicals being used was high grade.
Caprylyl chloride, nonanoyl chloride, and decanoyl chlo-
ride were from Shalong (Huzhou Zhejiang Province
China). n-Bromoheptane were from Yancheng (Jiangsu
Province China). m-Xylene, ethyl ether, magnesium strips,
anhydrous calcium chloride and sodium hydroxide were
obtained from Kemiou (Tian Jin China). All reagents were
distilled prior to use. Pd/C catalyst (5 %) was provided by
the Dalian Institute of Chemical Physics (Dalian China).
1-(2,4-Dimethyl-phenyl)-1-decanone (3a)
Decanoyl chloride (0.10 mol, 19.0 g) was added dropwise
to a stirred solution of anhydrous AlCl3 (0.13 mol, 17.36 g)
and m-xylene (0.40 mol, 42.4 g), compound 3a was
obtained with a 82.93 % yield as yellow oil starting from
following the same procedure described for 1a.
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633
Synthesis of Alcohols
until the pressure stabilized. Then the catalyst was filtered
off and washed with petroleum ether. The filtrate was then
decomposed with water. The aqueous solution was
extracted twice with petroleum ether. The solvent was
washed with NaHCO3 solution and distilled water,
respectively, until neutral, and dried over anhydrous cal-
cium chloride. The alkyl m-xylene isomers were obtained
after distillation under reduced pressure. Compound 1c was
obtained with a 93.24 % yield.
8-(2,4-Dimethyl)phenyl-pentadecyl-8-alcohol (1b)
The reaction was conducted under nitrogen. Traces of
iodine were used to initiate the Grignard reaction. n-bro-
moheptane (0.1 mol, 17.91 g) was added dropwise to the
mixture of the magnesium strips (50.4 g, 2.1 mol) and
Et2O (50 mL), then the reaction was placed in reflux until
the magnesium strips had disappeared. A suspension of 1a
(0.05 mol, 11.58 g) in Et2O (50 mL) was added dropwise
over 30 min to the Grignard reagent and heated at reflux
for 2 h. The resulting mixture was decomposed by ice-cold
dilute hydrochloric acid (100 mL). After the separation
phase, the aqueous solution was extracted three times with
ether. All extracts were combined, washed with deionized
water until neutral and dried over anhydrous calcium
chloride. Then 1b was distilled under reduced pressure.
Compound 1b was obtained with a 85.31 % yield.
8-(2,4-Dimethyl)phenyl-hexadecane (2c)
2b (0.05 mol, 17.35 g) in glacial acetic acid (50 mL) and
perchloric acid (1.0 mL) using 1.0 MPa H2 and 1.0 g Pd/C
(5 %) catalysts Pd/C was added in high-pressure reactor
reaction 12 h until the pressure stabilized. Compound 2c
was obtained with a 95.66 % yield as a yellow oil starting
from following the same procedure described for 1c.
8-(2,4-Dimethyl)phenyl-heptadecane (3c)
8-(2,4-Dimethyl)phenyl-hexadecyl-8-alcohol (2b)
3b (0.05 mol, 18.05 g) in glacial acetic acid (50 mL) and
perchloric acid (1.0 mL) using 1.0 MPa H2 and 1.0 g Pd/C
(5 %) catalysts Pd/C was added in high-pressure reactor
reaction 12 h until the pressure stabilized. Compound 3c
was obtained with a 96.12 % yield as yellow oil starting
from following the same procedure described for 1c.
n-Bromoheptane (0.1 mol, 17.91 g) was added dropwise to
the mixture of the magnesium strips (50.4 g, 2.1 mol) and
Et2O (50 mL), then the reaction was placed in reflux until
the magnesium strips had disappeared. A suspension of 1a
(0.05 mol, 12.28 g) in Et2O (50 mL) was added dropwise
over 30 min to the Grignard reagent and heated at reflux
for 2 h. Compound 2b was obtained with a 89.78 % yield
as yellow oil starting from following the same procedure
described for 1b.
Synthesis of Alkyl m-Xylene Sulfonates Isomers
2,4-Dimethyl-5-(1-heptyl)octyl Sodium Phenyl Sulfonate
(1d)
8-(2,4-Dimethyl)phenyl-heptadecyl-8-alcohol (3b)
Chlorosulfonic acid (0.05 mol, 5.53 g) was added dropwise
to the 1c (0.05 mol, 15.8 g). The reaction proceeded for
2 h at 10 °C. The sulfonation product was neutralized with
a sodium hydroxide solution. After phase separation, the
mixture was recrystallized three times with anhydrous
ethanol. The final product was filtered and dried in a vac-
uum oven at 80 °C. The purity of the product was deter-
mined by the two-phase titration methods. Purity: 98.8 %.
n-Bromoheptane (0.1 mol, 17.91 g) was added dropwise to
the mixture of the magnesium strips (50.4 g, 2.1 mol) and
Et2O (50 mL), then the reaction was placed in reflux until
the magnesium strips had disappeared. A suspension of 1a
(0.05 mol, 12.98 g) in Et2O (50 mL) was added dropwise
over 30 min to the Grignard reagent and heated at reflux
for 2 h. Compound 3b was obtained with a 89.78 % yield
as yellow oil starting from following the same procedure
described for 1b.
1
The structure was confirmed by H NMR.
1d 1H NMR [300 MHz, (CDCl3)] d = 0.80–0.88
(t, –CH3, 6H), 1.06–1.22(b, –CH2–, 20H), 1.42–1.52
(t, Me–CH2–, 4H), 2.74(m, –CH–, 1H), 2.18–2.28(s, Ar–H1,
6H), 7.64(s, Ar–H2, 1H).
Synthesis of Alkyl m-Xylene Isomers
8-(2,4-Dimethyl)phenyl-pentadecane (1c)
2,4-Dimethyl-5-(1-octyl)octyl Sodium Phenyl Sulfonate
(2d)
The alkyl m-xylene isomers were synthesized by hydro-
genation of the corresponding 1b (0.1 mol, 33.3 g) in
glacial acetic acid (50 mL) and perchloric acid (1.0 mL)
using 1.0 MPa H2 and 1.0 g Pd/C (5 %) catalysts. Pd/C
was added in the high-pressure reactor for 12 h reaction
Chlorosulfonic acid (0.05 mol, 5.53 g) was added dropwise
to the 2c (0.05 mol, 16.5 g) the reaction proceeded for 2 h
at 10 °C as the procedure described for 1d. The purity of
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J Surfact Deterg (2012) 15:631–636
2d was determined by the two-phase titration methods.
Purity: 98.3 %. The structure was confirmed by 1H NMR.
Table 1 Boiling stage of the intermediates
R1
R2
Boiling stage (°C)
Pressure (MPa)
1
2d H NMR (300 MHz, CDCl3)d:0.762–0.831(t, –CH3
Ketone
C7H15
C8H15
C9H19
Alcohol
C7H15
C8H15
C9H19
Alkane
C7H15
C8H15
C9H19
1, 3H), 0.841–0.868(t, –CH3 2,3H), 1.072–1.145(b, –CH2–,
22H), 1.482(m, Me–CH2–, 4H), 1.900(s, Ar–CH3 1, 3H),
2.128–2.160 (s, Ar–CH3 2, 3H), 2.314–2.369(m, –CH–, 1H),
6.985(s, Ar–H1, 1H), 7.555(s, Ar–H2, 1H).
C7H15
C7H15
C7H15
247–251
252–255
257–258
0.088
0.088
0.094
C7H15
C7H15
C7H15
240–242
310–314
240–265
0.086
0.078
0.093
2,4-Dimethyl-5-(1-octyl)nonyl Sodium Phenyl Sulfonate
(3d)
Chlorosulfonic acid(0.05 mol, 5.53 g) was added dropwise
to the 3c (0.05 mol, 17.2 g). The reaction proceeded for
2 h at 10 °C as the procedure described for 1d. The purity
of 3d was determined by the two-phase titration methods.
C7H15
C7H15
C7H15
223–225
284–286
214–227
0.086
0.078
0.092
1
Purity: 98.9 %. The structure was confirmed by H NMR.
3d 1H NMR (300 MHz, CDCl3)d = 0.853(t, –CH3,
6H),1.202(b, –CH2–, 24H),1.468(t, Me–CH2–, 4H),
2.289(s, Ar–CH3, 6H), 2.692(m, –CH–, 1H), 6.751(s, Ar–H1,
1H), 7.635(s, Ar–H2, 1H).
75
70
65
60
55
50
45
40
35
30
25
C15-8MXS
C16-8MXS
C17-8MXS
The structures of 1d, 2d, 3dwere confirmed by
1H-NMR spectral analyses. All analytical methods indi-
cated a high level of purity of all the isomers.
Results and Discussion
Properties and Purity of Intermediates and Final
Products
Alkyl m-xylene sulfonates isomers were prepared follow-
ing Scheme 1. The boiling points of the intermediates are
listed in Table 1. It can be seen that the boiling point
increased for the alkyl chain longer. And from ketone to
alkane, the boiling point becomes lower. The purities of the
Cx-MXS isomers was determined by two-phase titration
methods. C15-8MXS, C16-8MXS, C17-8MXS recrystal-
lized three times and their purities were 98.8, 98.3, 98.9 %
respectively.
-6.0
-5.5
-5.0
-4.5
-4.0
-3.5
-3.0
-2.5
log Concentration (M)
Fig. 1 Surface tension versus aqueous molar concentration (log
scale) of synthesized Cx-MXS isomers
correction factor which accounts for the nonsphericity of
the drop. Each surface tension value was determined from
the average at least five measurements.
Surface Tension Studies of Different Alkyl m-Xylene
Sulfonate isomers
Figure 1 shows the plot of surface tension versus con-
centration (in a log scale) of alkyl m-xylene sulfonates
isomers, exhibiting a break point which correspond to a
well-defined CMC beyond which remains essentially con-
stant. As the long alkyl chains increased, the m-xylene ring
located at the eighth carbon atom along the long alkyl
chains. The surfactant molecule tends to pack at the gas–
liquid interface closely. This is because the surfactant
molecules hydrophobic chain crimp together at the gas–
liquid interface. Accordingly, the CMC decreased, the
adsorption density increases, and the tension reduction is
strengthened.
The surface tension was measured by the drop-volume
technique in a water bath with thermostat control at
298 0.1 K. The time scale for one drop was 3–50 min
depending on the time required to attain equilibrium. The
surface tension was then measured three times for each
sample with a 3–50 min interval between each reading to
ensure equilibrium data. The surface tension (c) is given by
c = Fmg/R = uFVDq/R, where R is the tip’s radius, Dq
the difference of the two phases, g the local gravity
acceleration, V the volume of one drop, F(R/V)1/3 is a
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635
-4.0
-4.1
-4.2
-4.3
-4.4
-4.5
-4.6
-4.7
Table 2 cCMC and CMC values of Cx-8MXS
A (nm2) pC20
Alkyl m-xylene Sulfonate
Linear Fit
Surfactant
CMC
(10-5
mol L-1
cCMC
Cmax
(mN m-1
)
(10-10 mol
)
cm-2
)
C15-8MXS 7.98
C16-8MXS 4.32
C17-8MXS 2.45
25.9
0.911
1.43
1.84
1.82
1.16
0.90
6.68
5.95
5.84
26.03
26.61
Table 3 Variation of CMC compared with the Rosen equation
Log(CMC) =-0.2469-0.2569*m
Carbon atom number of the
hydrophobic chain
15
16
17
R2=0.9994
CMC calculated by the Rosen
expression
-2.82
-3.114 -3.408
15.0
15.5
16.0
16.5
17.0
CMC value of the fitting equation
-4.1004 -4.3573 -4.6142
Alkyl chain length
Fig. 2 Plot of CMC values versus alkyl chain length of alkyl
m-xylene sulfonate
Area per Molecule and Efficiency of Adsorption
The surface excess, C at the air–water interface was cal-
culated by applying the Gibbs adsorption isotherm equa-
tion. The area per molecule at the interface was estimated
from the corresponding value of C. Table 2 summarized
the values of CMC, cCMC, Cmax, Amin and pC20. As the
long alkyl chains increases, the surfactant molecule tends
to be packed more closely at the gas–liquid interface.
Accordingly, the CMC decreases, cCMC increases, the
surface area per molecule becomes smaller, and Cmax
increases, and the branched hydrophobic chain tends to
crimp together at the gas–liquid interface and reduces the
packing density at the gas–liquid interface.
decreased, and every increased a –CH2–, the CMC value
was reduced by almost half (Fig. 2). For the Rosen reported
equation of sodium alkane-1-sulfonate Log(CMC) =
1.59 - 0.294 9 m [20].
Acknowledgments This research was financially supported by the
National Key Basic Research Development Program (2005CB
221305).
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China and in the same year joined the School of Chemistry and
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Ya-bin Xu received a master’s degree in 2009 from the Northeast
Petroleum University in Heilongjiang Province of the P.R. China.
Xu’s fields of interest are the structure and the relationships of the
properties of novel surfactants.
Guo-qiao Li received a master’s degree in 2007 from the Northeast
Petroleum University in Heilongjiang Province of the P.R. China. Li’s
fields of interest are the structure and the relationships of the
properties of novel surfactants.
Xiao-yu Gao received a master’s degree in 2009 from the Northeast
Petroleum University in Heilongjiang Province of the P.R. China.
Gao’s fields of interest are the structure and the relationships of the
properties of novel surfactants.
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An-jun Li received a master’s degree in 2009 from the Northeast
Petroleum University in Heilongjiang Province of the P.R. China. Li’s
fields of interest are the structure and the relationships of the
properties of novel surfactants.
Dan-dan Yuan has been studying for a master’s degree at the
Northeast Petroleum University in Heilongjiang Province of the
People’s Republic of China since 2009. Yuan’s fields of interest are
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Author Biographies
Wei Tong received a master’s degree in 2010 from the Northeast
Petroleum University in Heilongjiang Province of the P.R. China.
Tong’s fields of interest are the structure and the relationships of the
properties of novel surfactants.
Huo-xin Luan received a master’s degree in 2010 from the Northeast
Petroleum University in Heilongjiang Province of the P.R. China,
then studied at the Oil–Gas Field Development Project majoring for a
Ph.D. at the Northeast Petroleum University of the P.R. China.
Zhong Li received a master’s degree in 2010 from the Northeast
Petroleum University in Heilongjiang Province of the P.R. China. Li’s
fields of interest are the structure and the relationships of the
properties of novel surfactants.
Wen-xiang Wu graduated in 1984 and in the same year worked at the
Northeast Petroleum University in Heilongjiang Province of the P.R.
China as a research chemist, mainly concentrating on oil and gas
development with a focus on enhancing oil recovery since then. He
received his Ph.D. in 1996 from the Northeast Petroleum University
in Heilongjiang Province of the P.R. China.
Kang Liu has been studying for a master’s degree at the Northeast
Petroleum University in Heilongjiang Province of the People’s
Republic of China since 2010. His fields of interest are the structure
and the relationships of the properties of novel surfactants.
Jie-cheng Cheng graduated in 1983 from Heilongjiang University in
Harbin of the P.R. China and in the same year joined to Daqing
Oilfield Limited Company of CNPC as a superior oilfield engineer.
He received his Ph.D. in 2000 from Dalian University of Technology
and is working with research in oil and gas development with a focus
on enhancing oil recovery.
Guo-yu Liu received a master’s degree in 2010 from the Northeast
Petroleum University in Heilongjiang Province of the P.R. China.
Liu’s fields of interest are the structure and relationships of the
properties of novel surfactants.
Tao Yu graduated in 1977 and in the same year worked at the
Northeast Petroleum University in Heilongjiang Province of the P.R.
China as a research chemist, mainly concentrating on the synthesis
and applications of surfactants and polymers.
Wei Ding graduated in 1985 and in the same year worked at Daqing
Petroleum Institute in Heilongjiang Province of the P.R. China as a
research chemist, mainly concentrating on the synthesis and appli-
cations of surfactants and polymers. He received his Ph.D. in 2005
from the Daqing Petroleum Institute in Heilongjiang Province of the
P.R. China.
Guang-miao Qu received a master’s degree in 2004 from the
Northeast Petroleum University in Heilongjiang Province of the P.R.
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