Environmental Engineering Reference
In-Depth Information
CH
3
CH
3
CHONO
2
+OH
CHOH+NO
3
CH
3
CH
3
CH
3
CHONO
2
+OH
CH
2
=CH-CH
3
+NO
3
+H
2
O
CH
3
CH
3
CH
3
CHONO
2
+OH
C=O+NO
2
+H
2
O
CH
3
CH
3
Only alcohol can be produced in the hydrolysis process of isopropyl nitrate in
neutral condition.
If sodium ethoxide is used, only butyl ethyl ether and sodium nitrate are pro-
duced in the reaction between tert-butyl nitrate and benzyl cyanide. Transesterifi-
-
cation reaction would not happen in this circumstance.
In the mixture of secondary alcohol or primary alcohol with tertiary esters, the
products of secondary alcohol esters or primary alcohol esters would be further
chemically combined immediately. A hydrogen atom in the raw esters would react
with
-
cation reaction would happen for tert-butyl nitrite because of the instability of NO.
ʱ
-carbon atom to form alcohols, which would not be oxidized. Transesterifi-
5.1.4 Reduction of Nitrate Esters
There are many methods to reduce nitrate esters from ester groups to alcoholic
hydroxyl groups, most likely to obtain the corresponding alcohols. The oldest, also
the most common, reduction method is the reductive hydrolysis by alkali sul
de or
alkali sulfhydrate, such as sodium sul
de, ammonium sul
de, or corresponding
sulfhydrate [
39
]. Transesteri
cation reaction would happen in the hydrolysis of
nitrate esters by sulfuric acid to form sulfate esters [
40
].
The corresponding alcohols can be obtained in several reaction conditions for
nitrate esters. For examples, in acetic acid solvent, iron is used as a reducer for
nitrate esters [
41
]. In pressure condition, iron and zinc are used to reduce nitrate
esters in acetic acid solvent, and palladium is used as a catalyst in the hydrogenation
process. By using palladium or platinum catalysts, nitrate esters is reduced by
hydrazine. The yield of reduction is up to 60
80 %. Some gases, such NO, N
2
, and
H
2
O, are also obtained in the reduction process.
Nitrate esters can be reduced in acetic anhydride if zinc is used in the reaction, or
reduced by electrolysis. They are prone to be reduced if lithium aluminum hydride
is used. The reaction is
-
finished in ether solution and the corresponding alcohols are
