Alcohols jojoba

Oil phase Mineral oil Isopropyl myristate Beeswax Cottonseed oil Cetostearyl alcohol Lanolin (and derivatives) White soft paraffin Yellow soft paraffin Canola oil Cetyl alcohol Arachis (peanut) oil Oleic acid Isopropyl palmitate Castor oil Stearyl alcohol Jojoba oil Stearic acid Silicone oils... 

See Magnesium coco-sulfate Alcohols, jojoba. See Jojoba alcohol Alcohols, lanolin. See Lanolin alcohol Alcohols, palm. See Palm alcohol Alcohols, palm kernel Alcohols, palm kernel oil. See Palm kernel alcohol Alcohols, palm kernel oil, monoester with sulfuric acid, ammonium salt. See Ammonium palm kernel sulfate Alcohols, palm oil. See Palm alcohol Alcohols, tallow. See Tallow alcohol Alcohols, tallow, hydrogenated. See Hydrogenated tallow alcohol A/co/ec 14(/, Aicoiec 439-C, Aicoiec 440-WD-, Aicoiec 495-, Aicoiec 662, Aicoiec BS, Aicoiec Extra A Aicoiec F-KXy, Aicoiec FF-10(t, Aicoiec Granuies, Aicoiec PG,... 

Synonyms Alcohols, jojoba Jobacohol Definition Alcohol fraction obtained by saponification of jojoba oil Toxicoiogy LD (oral, mouse) > 50 ml/kg Uses Emollient in cosmetics Jojoba (Buxus chinensis) extract CAS 90045-98-0 EINECS/ELINCS 289-964-3 Synonyms Buxus chinensis Jojoba extract Simmondsia chinensis extract Definition Extract of the nuts of the jojoba, Buxus chinensis... 

Isosorbide laurate Isostearamidopropyl morpholine lactate Isostearic acid Isostearyl alcohol Isostearyl avocadate Isostearyl behenate Isostearyl benzoate Isostearyl erucate Isostearyl glyceryl pentaerythrityl ether Isostearyl isononanoate Isostearyl isostearate Isostearyl lactate Isostearyl myristate Isostearyl neopentanoate Isostearyl octanoate Isotridecyl cocoate Isotridecyl isononanoate Isotridecyl myristate Japan (Rhus succedanea) wax Japan wax, synthetic Jojoba alcohol Jojoba esters Jojoba (Buxus chinensis) oil Jojoba oil, synthetic Jojoba wax... 

Jojoba Oil Jojoba oil is often referred to a hquid wax. It is not a triglyceride, but contains more than 90% esters of long-chain unsaturated fatty acids with unsaturated fatty alcohols. Jojoba oil is relatively stable to oxidation. It is widely used in cosmetics. There are numerous derivatives of jojoba available such as waxes or butters that are naturally derived. 

Fats and oils are one of the oldest classes of chemical compounds used by humans. Animal fats were prized for edibiUty, candles, lamp oils, and conversion to soap. Fats and oils are composed primarily of triglycerides (1), esters of glycerol and fatty acids. However, some oils such as sperm whale (1), jojoba (2), and orange roughy (3) are largely composed of wax esters (2). Waxes (qv) are esters of fatty acids with long-chain aUphatic alcohols, sterols, tocopherols, or similar materials. 

Jojoba. Jojoba oil [61789-91-1] is obtained from the seeds of the jojoba plant grown in semiarid regions of Costa Rica, Israel, Mexico, and the United States. The oil is made up of ca 80 wt % of esters of eicos-ll-enoic and docos-13-enoic acids, and eicos-ll- -l-ol, and docos-13- -l-ol, ca 17 wt % of other hquid esters, with the balance being free alcohols, free acids, and steroids. Jojoba oil is used primarily in the formulation of cosmetics. Hydrogenated jojoba oil is a wax used in candles and other low volume specialty apphcations. 

Jojoba is a desert crop that gives a small bean containing about 50% of a wax, a fatty acid ester with a fatty alcohol. The only other large source of such a wax is sperm whale oil, traditionally used in fine lubricants (see Lubrication and lubricants). Because the sperm whale is an endangered species, relatively Httle sperm whale oil is available and there is a large market for a substitute. Jojoba oil has been found to be usable for most of these appHcations. The jojoba oil is obtained by simply pressing the nut followed by conventional refining. Some jojoba oil is used in cosmetics (qv). 

The shape-selectivity of ZSM-5 is particularly remarkable. Active centres at the inner walls of the catalyst readily release protons to organic reactant molecules forming carbonium ions, which in turn, through loss of water and a succession of C—C forming steps, yield a mixture of hydrocarbons that is similar to gasoline. The feedstock can be methanol, ethanol, corn oil or jojoba oil. The shape-selectivity of this catalyst is particularly striking, as can be seen from the product distribution obtained for the dehydration of three different alcohols (Table 8.2). The product distribution can be understood in terms of the intermediate pore size of ZSM-5, which can accommodate linear alkanes and isoalkanes as well as monocyclic aromatic hydrocarbons smaller than 1, 3, 5-trimethyl benzene. In Table 8.3, we list some of the recent innovations in catalysis, to highlight the important place occupied by molecular-sieve catalysts. 

Jojoba wax, used in candles and cosmetics, is partially composed of the ester of stearic acid and a straight-chain C22 alcohol. Draw the structure of this ester. 

Esters obtained from alcohols and fatty acids have many remarkable applications. Those from long chain acids (12-20 carbon atoms) and short chain alcohols (3-8 carbon atoms) have been widely employed in the food, cosmetic, and pharmaceutical industries (1). Natural esters such as those from jojoba oil, carnauba wax, and whale oil have been used. However, these oils are expensive and are not usually available in large amounts. Therefore, it is desirable to develop methods for the production of such esters using cheaper and more plentiful raw materials (2). 

The jojoba plant (Simmondsia chinensis) produces wax esters rather than tri-acylglycerols in its seeds and it has become a significant crop for the cosmetic sector. Its wax consists mainly of long-chain fatty acids linked to long-chain fatty alcohols. 

The enzymatic esterification of oleic acid and oleyl alcohol to obtain oleyl oleate, which is a synthetic analogue of jojoba oil, was studied. The reaction was catalyzed by a commercially available immobilized lipase from Rhizomucor miehei. As solvents, carbon dioxide and liquid n-butane were used. Reactions were performed in a batch and in continuously operating high pressure reactors. 

Garver et al. (1992) developed an assay that measures the activity of the acyl-CoA alcohol transacyiase involved in the biosynthesis of storage liquid wax esters in jojoba and some microbes and algae. 

Jojoba oil is not a triacylglycerol but a mixture of wax esters based mainly on 20 1 and 22 1 acids and alcohols. It contains C40, C42, and C44 esters with two isolated double bonds (one in the acyl chain and one in the alkyl chain). The oil serves as replacement for sperm whale oil, which is proscribed in most countries because the sperm whale is an endangered species. At present, jojoba oil is a high-priced oil used mainly in cosmetics, but it has excellent lubricating properties and could be used extensively for this purpose if available in sufficient quantity at an appropriate price. 

Another oil of interest for lubricants is jojoba oil as a replacement of sperm whale oil, the use of which is now banned. Jojoba oil is not a triglyceride but is a wax ester composed mainly of straight chain esters of C20-C22 monounsaturated acids and alcohols. The major constituents, shown in Fig. 6.11, are eicosenyl and docosenyl eicosenoates, where m = 9 and n = 10, 12 ... 

Charge linoleic acid, safflower oil, jojoba oil, petrolatum, behenyl erucate, and cetyl alcohol and heat to 70°C. 

Jojoba oil consists primarily of wax esters of the acids listed here and long-chain alcohols. Kapok oil also contains up to 15% cyclopropene acids. 

The composition of hpids on the surface of leaves, stems, and fruits is quite different from that of hpids that form intracellular membranes. Their role is the protection of sensitive plant tissues against the loss of water and other biologically important volatiles. Waxes (i.e., esters of FA with monofunctional alcohols) are the most important components of these lipids. Some plant waxes are of commercial importance, such as camauba or candellila wax. They are solid at room temperature and in temperate climates, with the exception of liquid jojoba wax, and are plastic or even liquid in tropical climates. They contain bound saturated long-chain FA and alcohols. Waxes on the surface of apples and other fruits from temperate zones are solids or semisolid pastes, consisting of terpenes, ceryl cerotate, ceryl palmitate, and other esters. In the wax from lettuce leaves, higher alcohols prevail, with only small amounts of free FA (Bakker et al., 1998). Other components, such as alkanes, ketones, esters, secondary alcohols, were detected in other vegetables (e.g., in kale or rutabaga). 

Jojoba (jojoba oil). A perennial, dioecious plant (Sim-mondsia chinensis, Buxaceae) indigenous to California and Mexico. Oil content of seeds 45-50%, protein up to 30%. J. oil mp. 6.8-7°C, bp. 389°C. J. oil is an exception among the plant oils since it does not contain triglycerides but ra er a liquid wax ester. The main components of J. oil are docosenyl eicosenoate (37 %), eicosenyl eicosenoate (24%), and eicoseny 1 do-cosenoate (11%), thus mainly wax esters with 40 and 42 C atoms. The wax esters of J. oils are very stable to oxidation (see linoleic acid) since they consist to > 95% of mono-unsaturated fatty alcohols and acids of the ffl9-series. 

Bromination of jojoba oil in carbon tetrachloride yielded tetrabromojojoba derivatives at 20°C (9). When treated with excess base, these bromides yielded the corresponding acetylenes from Z,Z olefins of jojoba or allenes from the E,E isomerized jojoba (Scheme 2) with the expected hydrolysis to acid and alcohol. Allylic bromination (nonregiospecific) with A-bromosuccsinimide (NBS) followed by dehydro-halogenation yielded polyunsaturated oils with degrees of unsaturation up to the hexaenoic jojoba derivative (10). These highly unsaturated materials were envisioned... 

In cosmetic applications the freedom in using different oils is greater. Long-chain fatty acids, fatty alcohols, and simple esters such as isopropyl myristate (IPM), jojoba oil, and essential oils are only a few of the examples. In addition, various waxes, sterols, and paraffin oils have been tried. 

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