Advanced Materials Research Vols 550-553 (2012) pp 75-79 Online: 2012-07-26

© (2012) Trans Tech Publications, Switzerland

doi:10.4028/www.scientific.net/AMR.550-553.75

Preparation of Alkyl Polyglucoside Surfactants by One-Step

Jiayin Li a, Yanjun Liu b, Guo Zheng c, Yu Sund, Yaning Haoe, Tao Fuf

Tianjin textile fiber interfacial treatment engineering center, Tianjin Polytechnic University, Tianjin
300160, China
a
jiayinli2011@yeah.com, byjliu72@126.com, czhengguo@tjpu.edu.cn, dsunyu_1980@126.com,
e
haoyaning58@126.com, fft0680@163.com

Keywords: Glucose; Alkyl Polyglucoside; Synthesis; Yield;

Abstract. Dodecyl polyglucoside was synthesized by glucose and dodecanol using
P-toluenesulfonic acid as catalyst. The effects catalyst type, proportion of material, reaction
temperature and pressure were discussed in this paper. The most appropriate reaction conditions:
mole ratio of laurel alcohol and glucose 6:1, mass of ratio of P-toluenesulfonic and glucose 0.008:1,
reaction temperature 120˚C and reaction pressure 5.0kPa.

Introduction
Alkyl polyglucoside (APG) is a type of new pollution-free non-ionic surfactant. It combines
many advantages of non-ionic and anionic surface active agents [1]. This excellent type of
surfactants have such superior properties as low surface tension, high surfactivity, strong detersive
power, rich and stable foam, good compatibility with other surfactants and stable surface-active in
high concentration of electrolyte solution [2,3]. In addition, APG is obtained by aldolization using
glucose and fatty alcohols, the sources of which are widely and also be renewable and friendly
materials [4]. The other excellent performances of these surfactants are no stimulation to the skin
and eye, non-toxic, mild biodegradability. Therefore, it is widely used in many products, such as
detergent, cleaning agents, cosmetics, medicines additives, industrial emulsifier, ect.
At present, a variety of routes are used for synthesis alkyl glycoside, but the methods of one-step
process and two-step process are mainly used in industrial production [5,6]. Double alcohol
exchange steps are omitted in one-step method, where there are almost no low-level alkyl
polyglucoside exist in products with leading to process simple. And this approach is used in
industrialization. So in this paper, we focused on analysis the effects of the type of catalyst,
proportion of material, reaction temperature and pressure on yield of product [7]. The best reaction
conditions were confirmed to optimize this reaction.

Experiments
Materials. Dodecanol, (C12H26O), was supplied by Tianjin guangfu fine chemical industry research
institute. Glucose, (C6H12O6), was obtained from Nanjing yudehheng fine chemicals company.
P-toluenesulfonic acid, (C7H8O3S), P-TSA, was purchased from Rizhao lideshi chemical industry.
Sodium carbonate (Na2CO3) and 30% hydrogen peroxide (H2O2), were purchased from Tianjin
chemical reagent factory. Fehling reagent, was received by self-made.
The synthesis for dodecyl polyglucoside. Fig.1 illustrates that the synthesis mechanism for
alkyl polyglucoside. For all the reactions similar installations were used, consisting of a four-necked
round-bottom flask with stirrer, thermometer and vacuum device, the established ratio of dodecanol
and P-TSA were added into the reaction vessel. When the mixture reached desired temperature

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76 Advances in Chemical Engineering II

about 90-100˚C, then glucose was added in this system, keep reaction conditions at 120˚C /5.0kPa
for 3.5h. The end of reaction was confirmed by Fehling reagent [8]. After reaction finishing, cooled
the filtrate to 90˚C, and then adjusted pH value between 8.0 to 9.0 by 10% sodium bicarbonate
solution and filtered the mixture to separate the unreacted glucose. And then the reaction mixture
distilled at 140˚C /5.0kPa for 2h to remove excessive dodecanol. Finally 30% H2O2 was added in
mixture to bleach, getting light-yellow and transparent liquid.

CH2OH CH2 OH CH2OH

O O
O
H+ + -H2 O
HO OH HO O H HO OH +
OH OH
H
OH OH
OH
CH2OH CH2OH CH2OH
O O O
ROH + -H+
HO OH + HO OH O R HO O R
OH
H
OH OH
OH

Fig.1 The synthesis mechanism for alkyl polyglucoside

Yield of dodecyl polyglucoside
MI
Yielddp(%) = × 100
MG
Yielddp-Yield of dodecyl polyglucoside,%;
MI-Mass of dodecyl polyglucoside, g;
MG-Mass of glucose, g;

Results and discussion

The effect factors were investigated during preparing dodecyl polyglucoside, such as catalyst
type, proportion of material, reaction temperature and reaction pressure.
Effect of catalyst. Catalyst has great influence on the colour and lustre of products and plays an
important role in post-processing. So the choice of catalysts for the synthesis of APG plays a key
role. All advantages and disadvantages of these kinds of catalysts which are mentioned in the
literatures are considered. At present, inorganic acids, organic acids and solid acid are catalysts
which used commonly, such as dodecybenzene sulfonic acid, P-toluenesulfonic acid, sulfuric acid.
When the other conditions were set as followed: mole of ratio dodecanol and glucose 6:1, mass of
ratio P-TSA and glucose 0.008:1, reaction temperature 120˚C, reaction pressure 5.0kPa, the yield
and colour of products with different catalysts were shown in Table 1. From Table 1, it shows that
reaction rate, product color, the yield of dodecyl polyglucoside are superior to the other two
catalysts when adopted P-toluenesulfonic as catalyst. So in this paper chose P-toluenesulfonic as
catalyst.

Table 1
The influence of different catalyst for reaction
catalyst reaction time [h] Yield dp [%] colour of product
dodecylbenzenesulfonic acid 4.5 108 brown
p-toluenesulfonic acid 3.5 140 light-yellow
sulfuric acid 4 89 brownish
 Advanced Materials Research Vols. 550-553 77

Effect of mole ratio of dodecanol and glucose. When the reaction temperature, reaction
pressure and the mass ratio of P-TSA and glucose were fixed, respectively, 120˚C, 5.0kPa, 0.008:1,
there would be some variations on the yield with the mole ratio of laurel alcohol and glucose
changed, as was shown in Fig.2. Along with the ratio increasing, the yield of dodecyl polyglucoside
is firstly rise but get reduce trend later and reach maximum at mole ratio 6:1. The reason for this
phenomenon may be due to excessive alcohol which led to the concentration of catalyst get down,
consequently making the speed of reaction influenced. In addition, excessive alcohol would
increase the load in dealcoholization process. Thus, the most suitable mole ratio was 6:1.

150

140
Yield of lauryl glucoside/%

130

120

110

100

90

80
2 3 4 5 6 7

Mole ratio of dodecanol and glucose

Fig. 2 Effect of mole ratio of dodecanol and glucose

Effect of mass ratio of P-TSA and glucose. With the purpose of obtain the appropriate mass
ratio of p-TSA and glucose, the reaction temperature, reaction pressure and the mole ratio of laurel
and glucose were as followed: 120˚C, 5.0kPa, 6:1, when having the mass ratio of P-STA and
glucose changed, the result was given in Fig.3. It is obvious that the yield of dodecyl polyglucoside
reached maximum when the mass ratio at 0.008:1, and it indicate that increasing the concentration
of P-TSA is benefit for reaction. While the mass ratio continued increasing, the yield is decrease
instead. This is because the existence of large doses of catalyst would lead to react rapidly, and
much water cannot eliminate promptly in a short time. A great quantity sticky polysaccharide even
agglomerate carbonization could be formed during polymerization in the water environment.
Therefore, the yield of dodecyl polyglucoside and the quality of the products are seriously
influenced. Accordingly the most appropriate mass ratio was 0.008:1.

140

130
Yield of lauryl glucoside/%

120

110

100

90

80
0.004 0.005 0.006 0.007 0.008 0.009 0.010 0.011

Mass ratio of P-TSA and glucose

Fig. 3 Effect of mass ratio of P-TSA and glucose

78 Advances in Chemical Engineering II

Effect of reaction temperature. Glucose is a kind of thermal substance. Temperature is too high
to result in the colour of product getting deep and the quality of product will be affected severely.
Fixed other conditions as follow: mole ratio 6:1, mass ratio 0.008:1, reaction pressure 5.0kPa, and
the effect of reaction temperature on yield of product was observed with different reaction
temperature (Fig.4). Form Fig.4, dodecyl polyglucoside yield increases as the reaction temperature
present upward trend, and reach a maximum at 120˚C. But then the temperature rise again, yield
declined instead. The high temperature is more advantageous to side effects between glucose ring,
and this phenomenon become more obvious under the higher temperature. After considerating of
the above factors comprehensively, the optimum reaction temperature was 120˚C.

140

120
Yield of lauryl glucoside/%

100

80

60

40

20

100 105 110 115 120 125 130

Reaction temperature/℃

Fig. 4 Effect of reaction temperature

Effect of reaction pressure. The reaction pressure on yield of product was researched with
different reaction pressure and mole ratio, mass ratio, reaction temperature as followed: 6:1, 0.008:1,
120˚C. And the result was given in Fig.5, which indicate that the affection of reaction pressure on
yield of product is considerably obvious. Dehydration too quickly and completely was not
convenient to reaction continued, and the existence of a little water can enhance the catalyst
ionization to provide a large enough of hydrogen. The suitable reaction pressure was fixed 5.0kPa.

160
Yield of lauryl glucoside/%

150

140

130

120

110
2 3 4 5 6 7
Reaction pressure/kPa

Fig. 5 Effect of reaction pressure

 Advanced Materials Research Vols. 550-553 79

Conclusion
Dodecyl polyglucoside was synthesized by glucose and dodecanol using p-toluenesulfonic acid
as catalyst. The effect factors were investigated and obtained optimum condition as followed: the
mole ratio of dodecanol and glucose 6:1, the mass ratio of P-TSA and glucose 0.008:1, reaction
temperature 120˚C, reaction pressure 5.0kPa. At this condition, the light colour product was
obtained and the yield was relatively high, reaching 140.2%. The advantages of this synthetic route
were process route short, easy to operate and needs low energy and cost.

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[4] M.A. Camblor, A.Corma, S. Iborra, S. Miquel, J. Primo and S. Valencia: Journal of Catalysts,
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Advances in Chemical Engineering II
10.4028/www.scientific.net/AMR.550-553

Preparation of Alkyl Polyglucoside Surfactants by One-Step

10.4028/www.scientific.net/AMR.550-553.75