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ChemicalBook CAS DataBase List 2,4-Dinitrotoluene
121-14-2

2,4-Dinitrotoluene synthesis

11synthesis methods
4-Nitrotoluene is nitrated with mixed acid (containing equimolar HNO3) under controlled conditions and continuous operation to give a 96 % yield of 2,4-dinitrotoluene. In Meissner units, for tighter control of the whole process, cocurrent flow is used in each step to separate mono- and dinitration, but countercurrent flow is used between them to prevent underor overnitration; this is also done in one-step nitration plants. After nitration, if separation of the resulting emulsion is difficult, the introduction of pure product can give surprisingly rapid separation.
Alternative processes yield mixed isomer products. When toluene is nitrated directly under similar conditions with 2.1 equivalents of nitric acid, the product is a ca. 80 : 20 mixture of 2,4-dinitrotoluene and 2,6-dinitrotoluene [606-20-2]. Nitration of 2-nitrotoluene, which is sometimes present in surplus, gives a ca. 67 : 33 mixture of 2,4- and 2,6-dinitrotoluene. 
-

Yield:121-14-2 85% ,606-20-2 6.3% ,99-99-0 7.9%

Reaction Conditions:

with succinic acid anhydride;nitric acid at 4; for 50 h;Product distribution / selectivity;

Steps:

10
Examples 8 to 11 : Nitration of toluene using solid anhydridesExamples 8 to 1 1 illustrate the effect of the use of various solid acid anhydrides on the double nitration of toluene. In the examples 8 to 1 1 , a mixture of toluene (35 mmol, 3.75 ml), nitric acid (120 mmol, 5.04 ml), anhydride (120 mmol), zeolite Ηβ (Si/AI = 12.5; 2.0 g) and dichloromethane (10 ml) was stirred in a bath set at 50 °C for the stated period of time. The results are shown in Table 2.Table 2: The effect of solid acid anhydride on the nitration of toluene

References:

UNIVERSITY COLLEGE CARDIFF CONSULTANTS LIMITED;SMITH, Keith;EL-HITI, Gamal;ALOTAIBI, Mohammad WO2012/49513, 2012, A1 Location in patent:Page/Page column 10

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