Description
Isopropyl laurate is an ester with the formula C15H30O2and has low toxicity. Due to its physicochemical properties, it has a wide range of uses, as a flavoring agent for fragrances, lubricants, surfactants, or emerging solvents. Industrially, isopropyl laurate is prepared by esterification of lauric acid and isopropanol in the presence of a catalyst.
Uses
Isopropyl laurate can be used in the preparation of cosmetic products. Since it can supply an odor similar to alcohol, it is used as an ingredient in perfumes with a maximum concentration of 8%. It has moisturizing, emollient, emulsifying, and surfactant properties, and it can also be added to lotions, facial cosmetics, soaps, and shampoos.
It can prepare lubricants. It has low toxicity to the human body, so it is used as a lubricant in lamination processing and food packaging production. In addition, it has a lower boiling point than ordinary industrial lubricants and can be removed at low temperatures.
It acts as a solvent. Since it is a long-chain ester, it can replace other non-biodegradable short- and medium-chain esters. It has good solubility, high boiling point, good flow characteristics, and gloss, replacing many toxic and persistent industrial solvents in the environment.
It can be used as a binder for cigarette filters or as a plasticizer in polymers such as food packaging and toys.
Definition
ChEBI: Isopropyl dodecanoate is a fatty acid ester obtained by the formal condensation of carboxy group of dodecanoic acid with propan-2-ol. A metabolite found in human saliva. It has a role as a human metabolite. It is a fatty acid ester and an isopropyl ester. It is functionally related to a dodecanoic acid.
Flammability and Explosibility
Notclassified
Synthesis
General procedure for the synthesis of isopropyl dodecanoate (3a) from lauric acid (1a) (2.01 g, 10.0 mmol) and isopropanol: lauric acid (1a) was dissolved in methanol (10 mL) and the solution was transferred to a syringe. The syringe was mounted on a syringe pump. The methanol solution was pumped at a flow rate of 0.177 mL/min into a stainless steel column (4.0 mm ID x 50 mm length, 0.53 mL internal volume) filled with HO-SAS (334 mg). The stainless steel column was immersed in an oil bath at 110°C for heating. The system was connected to a back-pressure regulator and the pressure was maintained at 75 psi. the mixture eluted during the initial 10 min of the reaction was discarded. Subsequently, the reaction mixture was collected within 3 min and n-decane was added as an internal standard for gas chromatography (GC) analysis. The reaction mixture was continued to be collected in a glass flask for 30 min, after which the solvent was removed by evaporation. The crude product was purified by fast column chromatography on silica gel (SiO2) with hexane/ethyl acetate (5:1 v/v) as eluent, resulting in isopropyl dodecanoate (3a) (1.13 g, 99% yield).
References
[1] Chemistry Letters, 1997, # 1, p. 55 - 56
[2] Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 7, p. 680 - 684
[3] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 5, p. 607 - 612
[4] Medicinal Chemistry Research, 2011, vol. 20, # 6, p. 769 - 781
[5] Organic Preparations and Procedures International, 2005, vol. 37, # 1, p. 87 - 92
