Orange Oil, Distilled

A flask containing 15.0 gm (0.25 mole) of sodium azide in 100 ml of acetonitrile is stirred and cooled in an ice bath while 18.3 gm (0.113 mole) of iodine monochloride is added over a 10-20 min period. After stirring for an additional 5-10 min, 5.6 gm (0.1 mole) of isobutylene is added and then the reaction is allowed to warm to room temperature for 20 hr. The red-brown slurry is poured into 250 ml of water, extracted with 100 ml of ether three times, washed with 150 ml of 5 % sodium thiosulfate, washed four times with 250 ml portions of water, and dried over magnesium sulfate. The ether is removed at reduced pressure, leaving a slightly orange oil. Distillation behind a barricade yields 13.5 gm (60%), b.p. 68°-69°C (7 mm), n% 1.5292. 

Orange Oil, Distilled, occurs as a colorless to pale yellow liquid with a mild citrus floral odor. It is the volatile oil obtained by distillation from the fresh peel or juice of the... 

Citrus reticulata oil. See Tangerine (Citrus reticulata) oil Mandarin orange oil Citrus sinensis. See Orange oil, distilled Orange oil terpeneless Citrus sinensis extract. See Orange (Citrus aurantium duicis) extract Citrus sinensis oil. See Orange (Citrus aurantium duicis) oil... 

Orange oil, coldpressed. See Orange (Citrus aurantium dulcis) oil Orange oil, distilled... 

Oleoresin parsley leaf Oleoresin parsley seed Oleoresin turmeric Olibanum (Bosweliia carterii) oil Onion (Allium cepa) oil Orange (Citrus aurantium dulcis) extract Orange (Citrus aurantium dulcis) flower oil Orange (Citrus aurantium dulcis) oil Orange oil, distilled Orange (Citrus aurantium dulcis) peel extract... 

Adulterants such as lemon oil and terpenes are frequently used and may be detected by distillation tests as given for lemon and orange oils. Distilled oil of limes, the usual oil of commerce, is obtained from Jamaica, Dominica, and Tahiti, but chiefly from the island of Montserrat, the... 

By this process lemon oils are found to contain some 2 5 to 3 per cent, aldehydes, hand-pressed lime oil 8 per cent., citron or cedrat oil 4 per cent., and orange oil 0 75 to 1 per cent, but more recent work has shown that these results are somewhat too low, due probably in part to some of the aldehydes distilling over with the terpenes, and for oils containing only a small percentage of aldehydes, a volumetric method, such as the hydroa lamine process, as modified by A. H. Bennet is much to be preferred, as being both simpler and more rapid to carry out, and also. more accurate. 

Solutions of freshly prepared (Z)-ethene-l, 2-dithiol (1.84 g, 20 mmol) and trisulfur dichloride (3.34 g, 20mmol), each in Et20 (100 mL), were added at an equal rate to EtzO (1.5L) over 6 8 h with stirring under N2. The mixture was further stirred for several hours and then evaporated, leaving an orange oil which contained 80% of pentathiepin. The oil was purified by distillation at rt in vacuo and condensing the distillate in a trap cooled with acetone/solid C02. Small amounts of the pure product were obtained as yellow drops. 

These can be the natural material itself one example would be pieces of vanilla pod or an extract, e.g. vanilla extract. Extracts can be prepared in several ways. One is to distil or to steam distil the material of interest. Another is to extract the raw material with a solvent, e.g. ethyl alcohol. Alternatively, some materials are extracted by coating the leaves of a plant with cocoa butter and allowing the material of interest to migrate into the cocoa butter. These techniques are also used in preparing perfumery ingredients, indeed materials like orange oil are used in both flavours and perfumes. 

Several unsaturated cyclic hydrocarbons, having the general formula C]qHj5, occur in certain fragrant natural oils that are distilled from plant materials. These hydrocarbons are called terpenes and include pinene (in turpentine) and limonene (in lemon and orange oils). 

The volatile oil containing the essential flavor/aroma of the named plant, herb, root, bark, flower, etc. The volatile oil is obtained by distillation or expression, e.g. expressed Orange oil. 

A concentrated essential oil. Folding is a gravimctric/volumetric measure of the strength of a concentrated essential oil expressed as a multiple of a standard. A folded Citrus oil would be compared to the expressed oil (steam distilled oil in the case of distilled Lime oil), e.g. 5 x Orange oil. 

When all the diethylamine has been added the mixture is stirred for a further 10 min and then concentrated under reduced pressure. The residue is dissolved in methylene chloride (200 mL), washed with water (2 x 200 mL) and saturated brine (2 x 50 mL), and concentrated under reduced pressure to give an orange oil. The oil is distilled at reduced pressure to give 23.5-24.5 g (86-90%) of N,N-diethyl-2-methoxybenzamide (118-120°C/0.1 mm) as a straw-colored liquid. 

C. S-Dodeoen-2-one. The 3-carboxy-5-dodecen-2-one (9.0 g, 0.040 mol) is stirred in 150 mL of carbon tetrachloride (Note 16) in a 500-mL, three-necked, round-bottomed flask which is fitted with a reflux condenser, thermometer. Teflon-covered magnetic stirrer, and a ground-glass stopper. After the orange-yellow solution is heated at reflux for 1 hr, TLC analysis shows the reaction to be complete (Note 17). The reaction mixture is concentrated under reduced pressure with warming to afford 7.1 g (0.039 mol, 98%) of a red-orange oil. The product is sufficiently pure for most purposes. It may be purified by vacuum distillation at 105-107°C/2.7 mm (5.2 g, 0.03 mol, 71%) which yields a pale yellow oil (Note 18). 

The crude product is chromatographed on 350 g of silica (Note 8) using 1 1 ether-petroleum ether (40-60) as eluant. The chromatography is monitored by TLC (Note 9) and the appropriate fractions are combined. Removal of the solvent with a rotary evaporator gives a pale orange oil (Note 10) which was further purified by distillation to give 11.7 g (68%) of the 0-ester, bp 69-72 C (0.2 mm) (Note 11). ... 

Production of Citrus Essence Oils. Distillative concentration of citrus juices yields essence oils, which separate from the aqueous phase in the receiver when the distillate condenses. The composition of essence oils is similar to that of peel oils, but the essence oils usually contain larger quantities of aliphatic ethyl esters (e.g., ethyl butyrate in orange essence oil). Thus, their aroma resembles that of a particular juice more than that of peel oils. 

The encapsulated orange oil (0.1 g) was rehydrated in 7.5 ml distilled water via the use of a vortex mixer for 30 sec. Acetone (50 pi) containing 100 jug ethyl heptanoate (internal standard) was added and mixed for another 30 sec. This solution was forced through a preconditioned Sep-pak CIS reverse phase cartridge. 

Encapsulated orange oil samples (150 mg) were weighed into 10 ml vials and dissolved in 850 mg distilled water. Four ml of acetone containing 0.25 mg/ml 2-octanone as an internal standard were added dropwise to the dissolved samples. The samples were continuously agitated throughout the addition of the internal standard solution using a vortex mixer. 

Figures 1-4 illustrate the IFT behavior of four citrus oils against water as a function of time at different temperatures. All but one of the lemon oil 2 and orange oil 2 runs were made with triple distilled water. All lemon oil 1 and orange oil 1 runs were made with mono distilled water. Surface tension of the two water samples differed by 0.2 dynes/cm (mean of 6 runs). This difference is not believed to make a major contribution to the IFT aging behavior observed.

Figure 1. YIT aging behavior of the orange oil 2/triple distilled water interface ZS, 1.2 C O>O 50°C.

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