Almonds, oil of bitter

Artificial materials include aUphatic, aromatic, and terpene compounds that are made synthetically as opposed to those isolated from natural sources. As an example, ben2aldehyde may be made synthetically or obtained from oil of bitter almond (51) and t-menthol may be made synthetically or isolated from oil of Mentha arvensis var. to give Bra2iUan mint oil or com mint oil. 

Adolph Baeyer is credited with the first recognition of the general nature of the reaction between phenols and aldehydes in 1872 ([2,5-7] [18], Table 5.1). He reported formation of colorless resins when acidic solutions of pyrogallic acid or resorcinol were mixed with oil of bitter almonds, which consists primarily benzaldehyde. Baeyer also saw resin formation with acidic and basic solutions of phenol and acetaldehyde or chloral. Michael and Comey furthered Baeyer s work with additional studies on the behavior of benzaldehyde and phenols [2,19]. They studied a variety of acidic and basic catalysts and noted that reaction vigor followed the acid or base strength of the catalyst. Michael et al. also reported rapid oxidation and darkening of phenolic resins when catalyzed by alkaline materials. 

Chemical Designations - Synonyms Benzoic Aldehyde, Oil of Bitter Almond Chemical Formula C HjCHO. 

Oil of bitter almonds is obtained from the ketiiels (seeds) of the ordinary blilei almond, P/iiiiii.i. T/iygdahis i.imyguulus commimis), a trse which is cultivated in F.urope, Asia. Northern. Africa, and California. The kernels of the peach and apricot yield cssenttal oils which are practically identical with that from the alraond, and many sample of almond oil " of commerce are no doubt derived froni peach and... 

Dodge has based a process for the determination of benzaldehyde. A strong (2 5 N) alcoholic potash solution is required for the estimation, which is performed. by allowing a mixture of 10 c.c. of this solution with 1 to 2 grams benzaldehyde to stand at the ordinary temperature for twenty-four hours, after which the unabsorbed pota is titrated back with N/2 hydrochloric acid. A blank test is also made, and from the amount of potash entering into reaction, the percentage of aldehyde can be calculated. The process breaks down in the assay of natural oil of bitter almonds, probably due to the presence of benzaldehyde cyanhydrin. 

Bittermand, /. bitter almond, -geiat, m. spirit (or essence) of bitter almond. -61, n. oil of bitter almond, beocaldfhyde (kUut-Uches) nitrobenzene, -wasser, n. bitter-almond water. 

The aromatic aldehydes have a pleasant odour. (Oil of bitter almonds, vanillin, piperonal.)... 

Synonyms AI3-01239 AIDS-169362 BRN 0507540 C-06813 Caswell No. 600 CCRIS 2841 EINECS 202-716-0 EPA pesticide chemical code 056501 Essence of mirbane Essence of myrbane Mirbane oil NCEC60082 Nitrobenzol NSC 9573 Oil of bitter almonds Oil of mirbane Oil of myrbane RCRA waste number U169 UN 1662. 

Aldehydes derived fiom the CflHs, jHo series of alcohols. 206 Benzoic aldehyde or oil of bitter almonds.206... 

Ocewtenee.—In monj balsams and gums. In putrid urine. JPrepar< ion.—1. By the oxidation of oil of bitter almonds (p.29C). 

BENZALDEHYDE. [CAS 100-52-7], C6H5CHO, formula weight 106.12, colorless liquid, mp bp -26°C, bp 179°C, sp gr 1.046. Sometimes referred to as artificial almond oil or oil of bitter almonds, hen/aldehyde has a characteristic nullike odor. The compound is slightly soluble in H20, but is miscible in all proportions with alcohol or ether. On standing in air, benzaldehyde oxidizes readily to benzoic acid. Commercially, benzalde-hyde may be produced by (1) heating benzal chloride C H CHCL with calcium hydroxide. (2i heating calcium benzoate and calcium formate ... 

Various methods are used in extracting the oils from the plant tissue. Many are distilled with water or steam, Hie oil being carried over with the distillate. In others, as for example oil of bitter almonds, the oil develops in the tissues only after fermentation. It is then obtained by distillation. Anollter method, and one especially used for more delicate and valuable oils, is called enfleurage. In this method the flowers containing the oil are spread as a thin layer over a layer of lard or olive oil. The latter absorbs the delicate oil in the flowers, after which distillation may separate the volatile oil from the other. 

Wohler was also a co-discoverer of beryllium and silicon, as well as the synthesis of calcium carbide, among others. In 1834, WOhler and Liebig published an investigation of the oil of bitter almonds. They proved by their experiments that a group of carbon, hydrogen, and oxygen atoms can behave like an element, take the place of an element, and can be exchanged for elements in chemical compounds. Thus the foundation was laid of the doctrine of compound radicals, a doctrine which had a profound influence on the development of chemistry. 

The friendship of Woehler and Liebig stands out as a sublime example of scientific fraternity. Liebig spared no words in praise of his friend. The achievement of our joint work upon uric acid and oil of bitter almonds was his work. Without envy and without jealousy, hand in hand we plodded our way ... 

The nineteenth century also produced reagents for the one-electron oxidation of suitable substrates. For example, sulfuric acid was employed for many years as an analytical reagent because of some color reactions. Thus, Laurent treated benzimid , C28H10O2+HAz, a residue from the oil of bitter almonds (ben-zaldehyde) and observed an indigo blue solution [34]. On the other hand, the blue solution observed by Liebermann upon treatment of chrysene with sulfuric acid can be attributed to the chrysene radical cation [43]. 

There are also natural products that contain cyanide, for example the plant cassava (see pp. 255-6) and various fruit kernels such as almonds, apricots, and apples. Oil of bitter almonds, which is used in cooking, contains enough cyanide to be lethal, and people have committed suicide by drinking it. 

In 1841, Laurent obtained thiobenzaldehyde decamer from reacting oil of bitter almonds (which is mostly benzaldehyde) with ammonium sulfate (1841LA320), although the size of the oligomer was not established until... 

Aromatic Compounds—The carbo-cyclic compounds which in number far exceed those of the aliphatic series were originally called aromatic compounds because many of them possess aromatic properties, e.g.j oil of wintergreen, oil of bitter almonds, etc. They were included with the paraffin compounds in the various groups of alcohols, aldehydes, acids, etc. Later it was found that they differed from the aliphatic compounds and finally it was shown that the hydrocarbon benzene is related to the aromatic compounds just as methane is to the aliphatic compounds, i.e,j as the mother substance. 

Mono-nitro benzene is a pale yellow liquid heavier than water sp. gr. 1.2 boiling point 209.4 melting point +3 . It distils with water vapor and is soluble in alcohol. It is known as oil of mirhane, but because of its resemblance in odor to oil of bitter almonds it is used as a substitute for the latter in perfumes. The chief importance of the compound is due to its easy preparation and its transformation by reduction into amino benzene or aniline, through which it becomes the starting point in the manufacture of dyes. 

Conversely, as previously stated, the aldehydes on reduction yield the primary alcohols and in the case of benzaldehyde, which is a commonly occurring substance in oil of bitter almonds, this method is used in the preparation of the alcohol. In the case of the secondary alcohols oxidation to ketones is not easily accomplished but the reverse reaction, the reduction of the ketones to secondary alcohols does take place with ease. 

Step C Preparation of -2-ThiopheruMehyde). To the reaction mixture described under Step A is added enough 10% sodium hydroxide to r e the of the mixture to 5-6.5, preferably 6.0-6.5 (as determined by Hydrion Paper). The mixture is then steam distilled any material (unreacted thiophene) coming over below 100° is discarded. The 2-thiophenealdehyde is collected in the distillate. Steam distillation is continued until all odor (oil of bitter almonds) of 2-thiophenealdehyde disappears. If the distillate is basic, it is acidified with hydrochloric acid to a pH of. 2-4. The product is taken up in ether and the aqueous layer extracted twice more with ether. The ether solution is dried over calcium sulfate, the ether is removed by distillation, and the product is distilled from a Claisen flask, b.p. 72.5° at 7 mm., np 1.5920. 

C. Nitrogenated oils, containing carbon, hydrogen and oxygen with nitrogen (from HCN). Example Oil of Bitter Almonds. 

Shaath NA, Benveniste B. Natural oil of bitter almond. Perfum Flavor 1991 16(Nov-Dec) 17, 19-24. 

The new oil is benzyl alcohol, GeHsGHaOH. It is produced together with a salt of benzoic acid, GeHsGOgH, when benzaldehyde or oil of bitter almonds, GsHsGHO, is treated with a base. The reaction has become known as the Gan-nizzaro reaction (1853).—O.T.B.]... 

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