Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

A New Method in the Synthesis of Glycerol Monostearate Using Hypophosphorous Acid Catalyst

Document Type : Research Article

Authors
Hamid Reza Moghaddas Marzangoo
Mahboubeh Taherkhani
Rajabali Ebrahimi
Department of Chemistry, Takestan Branch, Islamic Azad University, Takestan, I.R. IRAN
Abstract
Glycerol monostearate (GMS) is an emulsifier and an important additive in the cosmetic, food and pharmaceutical industries. The aim of this research is to domestically produce this product in the country. In the GMS production method, specific control conditions along with a readily available and inexpensive catalyst called hypophosphorous acid (H3PO2) were used. The sample produced was compared with a control sample through IR, 13C-NMR, and 1H-NMR tests. Glycerol monostearate was synthesized with high yield and showed similar results to the control sample in all tests. This product replaced cocamidopropyl betaine in the formulation of shampoo. The shampoo sample was evaluated in sensitivity tests and a zein test. In the patch sensitivity test, a label containing the surfactant was placed on the arms of 10 testers, and no reports of sensitivity, itching, redness, or skin inflammation were observed within the specified time. In the panel sensitivity test, 10 panelists used this product and the moisture (Cor) and pH of the skin were also measured. The results of the moisture test showed an increase of 0.5 units of skin moisture compared to before using the sample. In the pH test, a 0.2 unit increase in skin pH of the testers was measured compared to before using the shampoo. In the zein test, skin sensitization by the shampoo and raw materials was evaluated. The result of this test for glycerol monostearate used in shampoo at a level of 65 milligrams of nitrogen from zein protein dissolved in 100 milliliters of sample solution indicates that this product is completely mild, does not cause skin sensitivity, and therefore is recommended as a replacement for cocamidopropyl betaine in scalp shampoo.
Keywords
Spinel
Cobalt
Aluminum
Combustion synthesis
Esterification reaction

Subjects

[1] Moran-Valero M.I., Ruiz-Henestrosa V.M.P., Pilosof A.M.R., Synergistic Performance of Lecithin and Glycerol Monostearate in Oil/Water Emulsions. Colloids and surfaces. B, Biointerfaces, 151: 68-75 (2017).
[2] Chan P.N.A., Chemical Properties and Applications of Food Additives: Flavor, Sweeteners, Food Colors, Texturizers. In: Cheung, P. (eds) Handbook of Food Chemistry. Springer, Berlin, Heidelberg (2014).
[3] Silva T.J., Barrera-Arellano D., Ribeiro A.P.B., Oleogel-Based Emulsions: Concepts, Structuring Agents, and Applications in Food J. food sci., 86(7): 2785-2801 (2021).
[4] Wu S., Wang G., Lu Z., Li Y., Zhou X., Chen L., Cao, J., Zhang L., Effects of Glycerol Monostearate and Tween 80 on the Physical Properties and Stability of Recombined Low-Fat Dairy Cream. Dairy Sci. & Technol., 96: 377-390 (2016).
[5] Han L., Wang T., Preparation of Glycerol Monostearate from Glycerol Carbonate and Stearic Acid, RSC Adv., 6: 34137-34145 (2016).
[6] Nagtode V.S., Cardoza C., Yasin H.K.A., Mali S.N., Tambe S.M., Roy P., Singh K., Goel A., Amin P.D., Thorat B.R., Cruz J.N., Pratap A.P., Green Surfactants (Biosurfactants): A Petroleum-Free Substitute for Sustainability-Comparison, Applications, Market, and Future Prospects. ACS omega, 8(13): 11674-11699 (2023).
[7] Mengesha A.E., Wydra R.J., Hilt J.Z., Bummer P.M., Binary Blend of Glyceryl Monooleate and Glyceryl Monostearate for Magnetically Induced Thermo-Responsive Local Drug Delivery System. Pharm. Res., 30(12): 3214-3224 (2013). 
[8] Krog N.J., Sparso F.V., Food Emulsifiers: Their Chemical and Physical Properties, in Food Emulsions, ed. S.E. Friberg, K. Larsson and J. Sjoblom, Marcel Dekker, Inc., New York, 45-91 (2004).
[9] Fiume M.M., Bergfeld W.F., Belsito D.V., Hill R.A., Klaassen, C.D., Liebler, D.C., Marks, J.G., Jr, Shank, R.C., Slaga, T. J., Snyder, P. W., Gill, L. J., Heldreth, B., Safety Assessment of Monoglyceryl Monoesters as Used in Cosmetics. Int J Toxicol., 39(3): 93S-126S (2020).
[10] Saatkamp R.H., Dos Santos B.M., Sanches M.P., Conte J., Rauber G.S., Caon T., Parize A.L., Drug-Excipient Compatibility Studies in Formulation Development: A Case Study with Benznidazole and Monoglycerides. J Pharm Biomed Anal, 235: 115634 (2023).
[11] Trotta M., Debernardi F., Caputo, O., Preparation of Solid Lipid Nanoparticles by a Solvent Emulsification-Diffusion Technique Int. J. Pharm., 257: 153-160 (2003).
[12] Ziobrowski Z., Kiss K., Rotkegel A., Nemestthy N., Krupiczk R., Gubicza L., Pervaporation Aided Enzymatic Production of Glycerol, Monostearate in Organic Solvents. Desalination Desalination, 241(1-3): 212-217 (2009).
[13] Ahmed R.A., Rashid S., Ruparelia K, Huddersman K., Transesterification Reaction of Tristearin (TS) & Glycerol Mono Stearate (GMS) Over Surface Basified PAN Fibrous Solid Catalyst, Energy Adv., 2: 1604-1625 (2023).
[14] Rytczak P., Kozilkiewicz M., Okruszek A., The Chemical Synthesis of Phosphorothioate and Phosphorodithioate Analogues of Lysophosphatidic Acid (LPA) and Cyclic Phosphatidic Acid (CPA), New J. Chem., 34: 1008-1017 (2010).
[15] Liu L., Corma A., Metal Catalysts for Heterogeneous Catalysis: From Single Atoms to Nanoclusters and Nanoparticles. Chem. Rev., 118(10): 4981-5079 (2018).
[16] Kavadia M.R., Yadav M.G., Odaneth A.A., Arvind M.L., Production of Glyceryl Monostearate by Immobilized Candida Antarctica B Lipase in Organic Media, J. Appl. Biotechnol. Bioeng., 2(3): 96-102 (2017).
[17] Yu C.C., Lee Y.S., Cheon B.S., Lee S.H., Synthesis of Glycerol Monostearate with High Purity. Bull. Korean. Chem. Soc., 24(8): 1229 (2003).
[18] Byun H.G., Eom T.K., Jung W.K., Kim S.K., Lipase Catalyzed Production of Monoacylglycerols by the Esterification of Fish Oil Fatty acids with Glycerol. Biotechnol., Bioprocess Eng., 12: 491-496 (2007).
[19] Freitas L, Perez V.H., Santos J.C., De Castro H.F., Enzymatic Synthesis of Glyceride Esters in Solvent-Free System: Influence of the Molar Ratio Lipase Source and Functional Activating Agent of the Support. J. Braz. Chem. Soc., 18(7): 1360-1366 (2007).
[20] Yesiloglu Y., Kilic I., Lipase-Catalyzed Esterification of Glycerol and Oleic Acid. JAOCS. 81(3): 281-284 (2004).
[21] Tinoco A., Gonçalves F., Costa A.F., Freitas D.S., Cavaco-Paulo A., Ribeiro A., Keratin:Zein Particles as Vehicles for Fragrance Release on Hair. Industrial Crops and Products. 159: 113067 (2021).
[22] Duvnjak, M., Kljak, K., Grbeša, D. (2021). Nitrogen Storage in Crops: Case Study of Zeins in Maize. IntechOpen. doi: 10.5772/intechopen.95380
[23] نعمت دوست م.، امانی ح.، ملک محمودی ش.، کریمی نژاد ح.، تولید آزمایشگاهی بیوسورفکتانت رامنولیپید به منظور کاربرد در تولید شامپوهای سبز، نشریه شیمی و مهندسی شیمی ایران، 40(3): 361-371 (1400)
[24] امین محلاتی ع.ر.، عالم زاده ا.، بررسی تولید استر استئاریک اسید سوربیتن، نشریه شیمی و مهندسی شیمی ایران، 33(3): 19-24 (1393)