Environmental Engineering Reference
In-Depth Information
In the addition reaction, the used basic catalyst can be an alkali metal hydroxide,
sodium carbonate and sodium alcohol. The addition reaction of multi-nitroalkane
does not need a catalyst because it has a stable strong acidic anion.
In the addition of nitromethane with group containing a double bond, hydrogen
atoms of nitroalkane are usually added to the atom of double bonds with less
hydrogen atoms, but the opposite results will be obtained with the presence of
unsaturated ethers. In the addition reaction between an unsaturated compound with
conjugated double bonds and an nitroalkane, double bonds will be isomerized.
NO 2
H 3 CCH 2 NO 2 +H 2 C=CH-CH=CH-CN
H 3 CCH
CH 2
CH
CH
NO 2
Nitroalkanes may also react with carbon-nitrogen double bond and nitrogen-
nitrogen double bond via addition reaction to form nitroalkylamines and unsatu-
rated nitro compounds [ 21 ].
R-CH
R-CH
+ R'NH 2
+ R''CH 2 NO 2
R'
C
NO 2
R'
N
Most of these reactions only can take place under acidic medium. If the R group
is an aromatic group, with an organic amine as catalyst, the reaction can take place
with product of
ˉ
-nitrostyrene.
C 6 H 5 CHO
þ
CH 3 NH 2 !
C 6 H 5 CH = NCH 3 þ
H 2 O
C 6 H 5 CH
¼
NCH 3 þ
CH 3 NO 2 !
C 6 H 5 CH
¼
NCHNO 2 þ
CH 3 NH 2
Nitroalkane and diazo salt can form the following product as:
O
H 5 C 6 N
N NO 2 + H 3 C
CH N
+
H 5 C 6 NH
NCCH 3
NO 2
NaNO 2
ONa
The product from this reaction can be dissolved in basic solution. With a sec-
ondary nitroalkane salt, the product was 2-nitro-2-phenylazopropane that is not
dissolved in basic solution.
O
CH 3
Cl + (H 3 C) 2 CH
N
H 5 C 6
N
N
C
NO 2
+NaCl
H 5 C 6
N
N
ONa
CH 3
-
double bond is not very stable and may explode or decompose to obtain the original
It is worth mentioning that, the addition product from nitroalkane and
-
N=N
Search WWH ::




Custom Search