Environmental Engineering Reference
In-Depth Information
5.1.3 Hydrolysis of Nitrate Esters
Monohydric alcohol and polyhydric alcohol nitrate would be hydrolyzed in weak
alkaline or weak acidic agents, but they are relatively dif
cult to be hydrolyzed in
neutral agents. The hydrolysis process is shown in the following equation.
RONO
2
þ
H
2
O
!
ROH
þ
HNO
3
Besides the main products of alcohols and acids, other compounds, including
aldehyde, ketone, hydroxycarboxylic acid, unsaturated hydrocarbons, and nitrous
acid, can be obtained in the hydrolysis process of nitrate esters [
31
].
In general, the corresponding alcohols can be obtained in the hydrolysis process
of esters, but rather a series of other compounds.
ð
Þ
2
þ
!
KNO
2
þ
2KNO
3
þ
þ
þ
C
3
H
4
ONO
2
5KOH
CH
3
COOK
HCOOK
3H
2
O
This equation cannot stand for all hydrolysis process of esters [
32
,
33
]. In the
same conditions, the hydrolysis products of different nitrate esters include phenolic
resin, oxalic acid, and ammonium. In alkaline agents, glycerol is not found in the
hydrolysis products [
34
].
If thiophenol is involved in nitroglycerine, glycerol is formed in hydrolysis in
alkaline agents.
Nitrous acid is only produced in the hydrolysis of nitrate esters with peroxide
structure. Under the in
uence of hydrolytic reagent, the structure of nitrate esters
would be changed to peroxide structure. Thus, nitrous acid would be produced in
the process.
fl
ROONO
þ
H
2
O
!
ROOH
þ
HNO
2
RCH
2
ONO
2
þ
H
2
O
!
RCH
2
OOH
þ
HNO
3
RCH
2
OOH
!
RCHO
þ
H
2
O
When nitrate esters are hydrolyzed in neutral agents and ethanol is treated by
potassium nitrate solution, the ethanol will not be oxidized even under boiling
solution [
35
]. Olefin is produced in the hydrolysis of tertiary alcohol nitrate. Under
the circumstance, besides the corresponding alcohols, a certain amount of isobu-
tylene is produced:
C
4
H
9
OH
2
H
3
O
þ
NO
C
4
H
9
ONO
2
þ
2H
2
O
!
H
3
O
þ
NO
3
C
4
H
9
ONO
2
þ
H
2
O
!
C
4
H
8
þ
In the hydrolysis of benzyl nitrate, both benzyl alcohol and benzaldehyde are
produced:
