Abstract
Jojoba liquid wax is a mixture of esters of long-chain fatty acids and fatty alcohols mainly C38:2–C46:2. The oil exhibits excellent emolliency on the skin and, therefore, is a component in many personal care cosmetic formulations. The virgin oil is a component of the seed of the jojoba (Simmondsia chinensis) plant which occurs naturally in the Sonora Desert in the United States and northwestern Mexico as well as in the northeastern Sahara desert. The seed contains 50–60% oil by dry weight. The plant has been introduced into Australia, Argentina, and Israel for commercial production of the jojoba oil. As a natural lubricant, we are seeking to explore its potential as a renewable industrial lubricant additive. Thus, we have chemically modified the carbon-carbon double bonds in the oil structure in order to improve its already good resistance to air oxidation so as to enhance its utility as well as its shelf life in nonpersonal care applications. To achieve this goal, we have hydroxylated its –C=C– bonds. Acylation of the resulting hydroxyl moieties has generated short-chain vicinal acyl substituents on the oil which keep the wax liquid, improving its cold flow properties and also protecting it from auto-oxidation and rancidity.
Highlights
Jojoba liquid wax is a mixture of esters of long-chain fatty acids and fatty alcohols mainly C38:2–C46:2. e oil exhibits excellent emolliency on the skin and, is a component in many personal care cosmetic formulations. e virgin oil is a component of the seed of the jojoba (Simmondsia chinensis) plant which occurs naturally in the Sonora Desert in the United States and northwestern Mexico as well as in the northeastern Sahara desert. e seed contains 50–60% oil by dry weight. e plant has been introduced into Australia, Argentina, and Israel for commercial production of the jojoba oil
Recent efforts to explore synthetic and enzymatic development of jojoba-like mimics or analogue esters are yet other approaches aimed at narrowing the availability gap [16, 17]. e latter approaches will become more practical when long-chain fatty acids from oilseed crops are commercially available using developing improved separation techniques for such oils. e ready availability of these Journal of Analytical Methods in Chemistry long-chain fatty acids and fatty alcohols as synthons will greatly facilitate synthetic approaches to jojoba-like esters
Hydration of the jojoba oil to the tetrahydroxy jojoba intermediate was via the oxirane which was carried out in a one-pot reaction. e oxirane was characterized from a sampled aliquot by its Fourier-transform infrared (FT-IR) spectrum having an additional relatively strong singlet asymmetric absorption band at 847 cm−1 and a H–C–O–C–H stretch at 2985 cm−1 (Figure 2(a)). is 847 cm−1 band of the diepoxy jojoba oil is in contrast to epoxy triglycerides which consistently give an asymmetric doublet at 825–845 cm−1
Summary
Jojoba liquid wax is a mixture of esters of long-chain fatty acids and fatty alcohols mainly C38:2–C46:2. e oil exhibits excellent emolliency on the skin and, is a component in many personal care cosmetic formulations. e virgin oil is a component of the seed of the jojoba (Simmondsia chinensis) plant which occurs naturally in the Sonora Desert in the United States and northwestern Mexico as well as in the northeastern Sahara desert. e seed contains 50–60% oil by dry weight. e plant has been introduced into Australia, Argentina, and Israel for commercial production of the jojoba oil. Introduction e jojoba plant, Simmondsia chinensis (Link), is native to the Sonora Desert of northwestern Mexico, California and neighboring states [1] It produces capsules with seeds which are rich in a unique oil that is a liquid wax. Jojoba oil is highly emollient and lends itself to use as a component in myriads of personal care cosmetic formulations Derivatization of this oil has been practiced for many years producing halogenated products from which polyunsaturated analogues of jojoba oil intermediates were generated for research and other needs [9,10,11,12,13]. E latter approaches will become more practical when long-chain fatty acids from oilseed crops are commercially available using developing improved separation techniques for such oils. The aim is to tap the natural emolliency of the oil into an improved cold flow-modified jojoba oil in the form of the acetate, propionate, and valerate esters that act as lubricant additive agents for base lubricant oils
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