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The nitration product produced on the largest scale, by far, is nitrobenzene. Many explosives are produced by nitration including trinitrophenol (picric acid), trinitrotoluene (TNT), and trinitroresorcinol (styphnic acid). [3] Another but more specialized method for making aryl–NO 2 group starts from halogenated phenols, is the Zinke nitration.
At the time, phenol was obtained from coal as a co-product of coke ovens and the manufacture of gas for gas lighting. Laclede Gas reports being asked to expand production of phenol (and toluene) to assist the war effort. [16] Both Monsanto [17] and Dow Chemical [18] began manufacturing synthetic phenol in 1915, with Dow being the main producer ...
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group (−NO 2) into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters ( −ONO 2 ) between alcohols and nitric acid (as occurs in the synthesis of nitroglycerin ).
Synthesis of DNP (right) from phenol and nitric acid via 2-Nitrophenol and 4-Nitrophenol. DNP has the chemical formula HOC 6 H 3 (NO 2) 2. As a solid, it is a yellow, crystalline and has a sweet, musty odor. [1] [2] It sublimates, is volatile with steam, and is soluble in most organic solvents as well as aqueous alkaline solutions. [2]
4-Nitrophenol is a product of the enzymatic cleavage of several synthetic substrates such as 4-nitrophenyl phosphate (used as a substrate for alkaline phosphatase), 4-nitrophenyl acetate (for carbonic anhydrase), 4-nitrophenyl-β-D-glucopyranoside and other sugar derivatives which are used to assay various glycosidase enzymes.
In female elephants, the two compounds 3-ethyl phenol and 2-ethyl 4,5 dimethylphenol have been detected in urine samples. [70] Temporal glands secretion examination showed the presence of phenol, m-cresol and p-cresol (4-methyl phenol) during musth in male elephants. [71] [72] [73] p-Cresol and o-cresol are also components of the human sweat.
Nitration of m-Nitrotoluene. The ortho effect also occurs when a meta-directing group is positioned in a meta arrangement relative to an ortho–para-directing group, a new substituent introduced into the molecule tends to preferentially occupy the ortho position relative to the meta-directing group rather than the para position.
Phenol oxidation with hypervalent iodine reagents leads to the formation of quinone-type products or iodonium ylides, depending on the structure of the phenol. Trapping of either product is possible with a suitable reagent, and this method is often employed in tandem with a second process.