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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.
The phrase ipso nitration was first used by Perrin and Skinner in 1971, in an investigation into chloroanisole nitration. [18] In one protocol, 4-chloro- n -butylbenzene is reacted with sodium nitrite in t -butanol in the presence of 0.5 mol% Pd 2 (dba) 3 , a biarylphosphine ligand and a phase-transfer catalyst to provide 4-nitro- n -butylbenzene.
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 ...
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]
Chlorobenzene is treated with aqueous sodium hydroxide at 350 °C and 300 bar or molten sodium hydroxide at 350 °C to convert it to sodium phenoxide, which yields phenol upon acidification. [2] When 1-[ 14 C]-1-chlorobenzene was subjected to aqueous NaOH at 395 °C, ipso the substitution product 1-[ 14 C]-phenol was formed in 54% yield, while ...
Phenol is reduced to benzene when it is distilled with zinc dust or when its vapour is passed over granules of zinc at 400 °C: [22] C 6 H 5 OH + Zn → C 6 H 6 + ZnO. When phenol is treated with diazomethane in the presence of boron trifluoride (BF 3), anisole is obtained as the main product and nitrogen gas as a byproduct. C 6 H 5 OH + CH 2 N ...
1,3-Dinitrobenzene is accessible by nitration of nitrobenzene. The reaction proceeds under acid catalysis using sulfuric acid. The directing effect of the nitro group of nitrobenzene leads to 93% of the product resulting from nitration at the meta-position. The ortho- and para-products occur in only 6% and 1%, respectively. [1]
The Raschig–Hooker process's ability to make phenol makes it comparable to other methods, such as the Dow and Bayer process, which also converts benzene into phenol. In fact, the ability to recycle the hydrogen chloride made the Raschig–Hooker process preferable to the Dow and Bayer process, which requires its sodium chloride product to be ...