Musk Toluene

The natural musks were always very expensive and their macrocyclic structures presented synthetic challenges which were not conquered, even on laboratory scale, until the pioneering work of Ruzicka in 1926. It was therefore of major importance to the fragrance industry when, in 1888, Baur discovered the nitromusks. He had actually been working on explosives and noticed that the product of t-butylation of trinitrotoluene (TNT) had a pleasant, sweet, musky odour. The compound was named Musk Baur (38), although the alternative name, Musk Toluene , eventually became more common. For a while it was also known as Tonkinol because of the similarity of its odour to that of musk Tonkin. Baur then searched for analogues of this material and... 

Still later Baur has shown that if an acetyl group is introduced into the butyl toluene molecule, and the methyl ketone thus formed is nitrated, artificial musk (ketone musk) is produced. One part of butyl toluene, 10 parts of carbon disulphide, and 6 parts of aluminium chloride are cooled in a flask and 6 parts of acetyl chloride are run in quickly. After distillation on a water-bath, the residue is poured on to ice and treated in the usual manner. The acetyl derivative is obtained as an oil with a pleasant aromatic odour, boiling at 255° to 258°, of the formula—... 

Musk AW, Peters JM, Diberardinis L, et al. 1982. Absence of respiratory effects in subjects exposed to low concentrations of toluene diisocyanate and diphenylmethyldiisocyanate. J Occup Med 24(10) 746-750. 

T rinitro-5-( tert-hutyl)-2-methoxy- toluene, yel ndls, having an odor of musk, mp 69 70° was prepd from the Ag salt of butyltrinitro-ortho -cresol as described in Ref 2, or by nitrating butyl-ortho-methoxytoluene(Ref 2). The expl props of these trinitro-derivs were not detd Refs l)Beil 6,[507-8] 2)A.Baur, Ber 27,... 

Refs 3 Sc 6) 2,4,6- Trinitro-3-(iso-butyl)-toluene, crysts(from dil ale), having an odor resembling that of musk, mp 124° was prepd by nitrating m-iso butyltoluene(Refs l 5) and2,4,6-Trinitro 3-(tert-butylytoluene, It yel ndls(from ale), having an odor of musk, mp 96-7° readily sol in ale, eth, chlf, benz Sc petr eth insol in w was prepd by nitrating m-tert-butyltoluene(Refs 2,4,6 7). 

By using water-soluble organic solvents, usually referred to as precipitants, the reaction can be directed to produce only one cyclodextrin. In the presence of toluene, the enzyme from B. macerans produces only (3-cyclodextrin and linear starch chains. Beta-cyclodextrin can be separated from the soluble starch chains and recovered as a precipitated toluene complex. In the presence of decanol, a-cyclodextrin is the only cyclodextrin produced using the enzyme from B. macerans.21,22 Precipitants such as large cyclic compounds similar to musk oil23 or a-naphthol and methyl ethyl ketone (butanone)24 can be used to produce 8-cyclodextrin. 

One of the earliest perfumery materials to be produced industrially was benzaldehyde, prepared from toluene in 1866. In 1868 coumarin was first synthesized, soon to be followed by heliotropin, ionone, and vanillin. The first nitro musks appeared in 1888, and amyl salicylate in 1898. Since then, for the last hundred years, the history of perfumery has been dominated by the creation of new aromatic chemicals. 

Litz [100] assessed the ecotoxicity of 44 organic contaminants in biosolids and provided an overview of the compounds found to be of primary relevance (Table 7). Toluene, 1,4-dichlorobenzene, 1,2,4-trichlorobenzene, hexachloro-benzene, 1,1,1-trichloroethene, tetrachloroethene, DDT (incl. DDE, DDD), lindane, 2,4-dichlorophenol, pentachlorophenol, Ugilec, bromophosethyl, silicones, and phenols were proposed as substances of secondary relevance. Litz [100] stated a need for additional information for the following substances clofibrin acid, chloroparaffins, EDTA, musk xylene, tris-(chloroethyl) phosphate, deca-, penta- and octabromodiphenyl ethers, 2,4,6-trichlorophenol, 2,4-dimethyl phenol, ethynyl estradiol, polyacrylic acid sodium salt, polyacrylamides (cationic), and DNBP (di-n-butyl phthalate). 

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