PRIORITATILE CHIMIEI PENTRU O DEZVOLTARE DURABILA PRIOCHEM 8- ICECHIM- Bucuresti 25-26 octombrie 2012

Adina Ionuta Gavrila, Petre Chipurici

Faculty of Applied Chemistry and Material Science, University Politehnica of Bucharest, 149 Calea Victoriei, 1st district, Bucharest, Romania

INTRODUCTION

Biosurfactants are very important because they can replace chemically synthesized surfactants in many industrial applications 1. These biosurfactants can be
obtained from renewable substrates, that are readily available and inexpensive 2. Surfactants based on carbohydrates are biocompatible, completely biodegradable, non-
toxic, without odour and taste and non-irritant for skin. For this reason they are used in pharmaceutical, medicine, bioremediation and food areas 3.
The purpose of this paper is to develop an efficient enzymatic method for the synthesis of carbohydrate esters of fatty acids. Development of synthetic methods
involve improving the outcome of the reaction rate, conversion, regioselectivity, productivity, safety and catalytic stability. The main objective is the development of
enzymatic methods for obtaining glucose esters with fatty acids, using solvents as adjuvants in the esterification process. The experimental program followed the
influence of various parameters on the conversion of fatty acids (temperature reaction; enzyme concentration; type of fatty acid; solvent type).

RESULTS AND DISCUSSION

The enzymatic synthesis presents the advantages of higher yields and milder reaction conditions, resulting in high quality products with low energy
consumption.
This type of esterification is benefic for production of biosurfactants having applications in food and cosmetics.
The objectives of the project are:
- the development of enzymatic methods for obtaining glucose esters with fatty acids;
- the influence of working parameters on enzymatic esterification reaction
- use solvents as adjuvants in the esterification process.
Development of synthetic methods involve improving of the reaction rate, conversion, regioselectivity, productivity, safety and catalytic stability.
The main operations performed to achieve synthesis:
- carbohydrate (glucose) together with fatty acid (myristic acid), solvent and molecular sieves are preheated to 40 °C.
- the enzyme was added and the esterification takes place at 55-60°C.
- after esterification reaction mixture is filtered to remove the enzyme and molecular sieves. Ester solutions were analyzed by HPLC chromatography.

100 100 100

Acetone 5% 56-57 °C reflux
90 Methy ethyl ketone 90 8% 90 o
40 C
12% o
80 80 80 30 C
15%
Fatty acid conversion, %

Fatty acid conversion, %

Fatty acid conversion, %

70 70 70

60 60 60

50 50 50

40 40 40

30 30 30

20 20 20

10 10 10

0 0 0
0 2 4 6 8 10 0 2 4 6 8 10 0 2 4 6 8 10
Time, h Time, h Time, h

The influence of different solvents on fatty acid The influence of the amount of enzyme in the Influence of reaction temperature on
conversion on the enzymatic esterification of glucose conversion of fatty acid conversion of fatty acid
with myristic acid

CONCLUSIONS

•The advantages of enzymatic synthesis are higher yields and milder reaction conditions, resulting in high quality products with low energy consumption.
•The results obtained in the experiments show the possibility of obtaining of glucose fatty acid esters by enzymatic esterification.
• Increasing the temperature leads to the increasing of acid conversion, but temperatures higher than 60 ° C denaturation of the enzyme can occur.
• Increasing the concentration of the enzyme leads to an increase in fatty acid conversion. A significant increase occurs up to 12% enzyme concetration
and then is just a small increase and does not justify the use of large amounts of enzyme.
•Glucose esters of fatty acids are used as emulsifiers in foods, cosmetics and pharmaceuticals.
REFERENCES
1. Kosaric N., Pure & Appl. Chem., 64 (11), pp. 1731-1737,1992.
2. Baccile, N.; Nassif, N.; Malfatti, L.; Van Bogaert, I. N. A.; Soetaert, W.; Pehau-Arnaudet, G.; Babonneau, F. Green Chem., 12, 1564–1567, 2010.
3. Chang, S. W., Shaw, J. F., New Biotechnology, 26 (3-4), pp. 109-116, 2009.

E-mail: adinagav@yahoo.coo