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Synthesis and Properties of Ethoxylated Glycerol Monooleate As Palm Oil Based Nonionic Surfactants

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Synthesis and Properties of Ethoxylated Glycerol Monooleate As Palm Oil Based Nonionic Surfactants ISSN 0853 – 2788 JKTI, Vol. 17, No. 1, Juni 2015 : 49 - 55 Akreditasi No : 540/AU1/P2MI-LIPI/06/2013 SYNTHESIS AND PROPERTIES OF ETHOXYLATED GLYCEROL MONOOLEATE AS PALM OIL BASED NONIONIC SURFACTANTS SINTESIS DAN PROPERTI GLISEROL MONOOLEAT ETOKSILAT SEBAGAI SURFAKTAN NONIONIK BERBASIS MINYAK KELAPA SAWIT Indri Badria Adilina, Egi Agustian, Yenny Meliana, and Anny Sulaswatty Research Centre for Chemistry – Indonesian Institute of Sciences Kawasan Puspiptek Serpong, Tangerang, Indonesia 15314 Email : [email protected] Diterima: 07 Maret 2015, Revisi: 27 Maret 2015, Disetujui: 10 April 2015 ABSTRACT Development of bio-based surfactants has been performed by various chemical Palm oil based nonionic surfactants were reactions, such as ethoxylation, synthesized by reacting glycerol monooleate with esterification, sulfonation, or amidation. In ethylene oxide at 80 ºC in the prescence of an alkaline catalyst. Purification of the products was the case of ethoxylation reaction, it conducted by use of acetic acid and black carbon generally occurs in the prescence of an which gave ethoxylated products (EGMO) with a alkaline catalyst, usually potassium higher level of viscocity and greater solubility in hydroxide (KOH) or sodium hydroxide water. Physical and chemical properties of the (NaOH), and a starter (2,3). The starter in the product such as surface activity, cloud point, acid value, ester value, hydroxyl value, and hydrophilic- synthesis of nonionic surfactant could be a lipophilic balance was also determined and results fatty alcohol, an alkyl phenol, or a fatty varied depending on the reagent molar ratio. The acid, which are hydrophobic molecules synthesized EGMO were soluble in water and containing a polar group with an active therefore show potential use as surface active agents hydrogen. Fatty alcohols do not in personal care and cosmetic products. predominantly exist in nature and a Keywords: nonionic surfactant, ethoxylation, reduction step from fatty esters is required glycerol monooleate, palm oilKata to obtain the fatty alcohol as a starting material and therefore a more effective method is desirable. INTRODUCTION Direct ethoxylation of fatty acid Palm oil is one of the highly potential methyl esters such as glycerol monooleate vegetable oils for the substitution of (GMO) is a favorable method since it is products derivered from petroleum such as able to reduce the production cycle of fatty surfactants. With the advanced alcohols thus significant cost reduction development of oleochemistry, surfactants could be expected(4,5). We have previously from palm oil is becoming an interesting reported a direct ethoxylation of GMO from issue to be investigated. Many types of palm oil in the presence of an alkaline surfactants are found in the market, among catalyst at temperatures of 120 to 180 ºC(6). them are ionic, nonionic, or zwitter ionic. The ethoxylation reaction proceeded and These surface active agents are used in ethylene oxide (EO) was inserted between many personal care and cosmetic products the carbonyl carbon and fatty acid group at as well as industrial processes. They can act the ester bond. The aim of this present as a detergent, emulsifier or dispersants in study is to further investigate the colloidal systems(1). preparation of ethoxylated glycerol monooleate (EGMO) at a lower 49 JKTI, Vol. 17, No. 1, Juni 2015 : 49 - 55 temperature of 80 ºC in 1 atm and purified by using acetic acid and adsorption determine their properties after purification with black carbon. with acetic acid and black carbon. Determination of physical and chemical MATERIAL AND METHODS properties of EGMO Acid, ester, and hydroxyl value were Materials determined by standard titration analysis. GMO was synthesized by a typical An Ostwald viscometer and picnometer esterification reaction of glycerol and fatty were used for determination of viscosity acid of palm oil which was provided by PT. and density. The solubility in water was Sumiasih, Indonesia. Ethylene oxide determined by observing the appearance of (Sigma Aldrich) and KOH (Merck) were 0.01–1 % EGMO product in demineralized used for the ethoxylation process. Water water. Surface tension analysis was was redistilled, acetic acid (Merck) and conducted using a torsiometer (Torsion carbon black were used for purification. Balance Supplies) for surface and interfacial tension of 0.05 % aqueous A 2 L autoclave reactor was used for EGMO product at 25 ºC equipped with a ethoxylation and gas chromatography Pt-Ir du Noüy ring. (Shimadzu 14A, column DB5-MS 30 m x 0.25 m x 0.25 μm, FID detector) was Cloud point was determined by required for determination of components freezing (± 4 ºC) 1 % of aqueous solution of in the starting material GMO. Vapour ethoxylation product and then heating it to Pressure Osmosis (VPO K700 KNAEUR 100 ºC. The temperature when the clear with Euro Osmo K7000) and liquid solution suddenly becomes cloudy is chromatography-mass spectroscopy (Perkin recorded as the cloud point. Sodium Elmer Series 200) was applied for chloride was used when the cloud point was molecular weight determination. For not observed to the boiling point of water. surface tension analysis, a tensiometer Hydrophylic lipophylic balance (HLB) (Torsion Balance Supplies) equipped with a which is useful to identify surfactants for Pt–Ir du Noüy ring was used. Viscosity was oil in water systems was determined by a determined with an Ostwald viscometer, calculation made by Sasol Olefin & whereas density was revealed with a Surfactants with the following equation(7): standard picnometer. HLB = 20 x MW Hydrophilic (1) Methods MW Total Synthesis of ethoxylated glycerol monoleate The molecular weight of the (EGMO) ethoxylation product was determined by GMO and 1 % KOH were introduced vapor pressure osmosis whereas samples into the reactor and the mixture was stirred were injected to the sample valve and the for 2 hours without heating until the molecular weight was recorded. mixture was neutral. EO was flowed into Composition of the products was evaluated the reactor and the mixture was heated at 80 by LC-MS with positive ion mode. ºC for 2 hours. At the end of the process, Methanol and water with ratio 80:20 was the reaction was stirred for 3 hours in room used as the mobile phase at a flow rate of temperature of 29 ºC. Ethoxylation was 0.1 mL/min. Electrospray was carried out performed with variation of molar ratio of using column C18 (RP 18) Vydac with GMO and EO. The EGMO product was column length of 250 mm, ID: 2 mm, and particle size: 5μm. 50 Synthesis and Properties of Ethoxylated Glycerol Monooleate as Palm Oil Based Nonionic Surfactants : Indri Badria Adilina, dkk RESULT AND DISCUSSION Direct ethoxylation of GMO GMO as the starting material was analyzed by gas chromatography. The GMO were synthesized by a typical fischer esterification of glycerol and a mixture of fatty acid from palm oil which mainly contained oleic acid, commercially available in the local market. The types of fatty acid in the esters in the synthesized GMO were determined as shown in Fig. 1. Results show that the GMO sample was Fig. 1 Types and composition of fatty acids in dominated by esters of oleic acid (76.58 %) the startingmaterial and linoleic acid (16.44 %). Other fatty acid esters with small concentration were also An amount of KOH was used as a detected as stearic acid (2.41 %), palmitic catalyst in the ethoxylation reaction and acid (0.83 %), and linolenic acid (0.20 %). therefore purification is needed to separate Synthesis of the nonionic surfactant the catalyst from the product, whereas the was performed by reacting GMO with EO unreacted EO which remained in the gas at 80 ºC in the prescence of an alkaline form after the reaction was purged out of catalyst. Table 1 shows the parameters of the reactor. The process resulted in three reaction of the ethoxylation products. GMO EGMO products based on the variation of as the starting material has one ester group reagent molar ratio GMO : EO, labeled as in its molecule. As reported in other direct A, B, and C. The three EGMO products ethoxylation papers (1-5), the ethylene oxide is selectively inserted between the carbonyl group and ester bond. The ethoxylation product consists of two parts; the hydrophobic portion from oleic acid and the hydrophilic portion from ethylene oxide insertion. Scheme 2. Ethoxylation of GMO to ethoxylated glycerol monooleate (EGMO) Scheme 1. Esterification of glycerol and oleic acid to glycerol monooleate (GMO) 51 JKTI, Vol. 17, No. 1, Juni 2015 : 49 - 55 Table 1. Ethoxylation products and reaction parameters GMO : EO EGMO KOH Time Temperature Purification pH (mol) (% wt/wt) (minute) (ºC) 1:2 A 1 120 80 - 9.8 1:6 B 1 120 80 - 7.8 1:10 C 1 120 80 - 7.8 1:2 AP 1 120 80 Purfied 5.0 1:6 BP 1 120 80 Purified 5.0 1:10 CP 1 120 80 Purified 3.8 EGMO = ethoxylated products; GMO:EO = molar ration of GMO and EO; A, B, C = ethoxylated products A, B, and C before purification; AP, BP, and CP = ethoxylated products A, B, and C after purification Physical and chemical properties of increase of pressure and reagent molar EGMO product ratio. The acid and ester values of EGMO The amount of hydrophilic part in the products are illustrated in Fig. 2. It can be molecule which is the amount of EO seen that an increase of acid value was inserted into the structure was analyzed and detected after purification. Before the calculated by LC-MS method as can be EGMO purification, the acid value of A seen in Table 2. When a higher GMO : EO was 0.41. An increase of more than 5 points ratio was applied, a larger number of EO was seen after purification where the acid and average molecular weight (MW) was value of AP elevated to 6.07.
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