Organic Chemistry of Explosives

334 Miscellaneous Explosive Compounds

OH

O

O

HO

O

O

O

O

Cl

O

O

O

O

N 3

2 ClCH 2 CH 2 OH

H 2 SO 4 , PhCH 3

90 % 1

2

(BAEA)

EtOH, NaN 3

72 %

Cl

N 3

Figure 8.1

Agrawal and co-workers^6 synthesized the energetic plasticizer bis(2-azidoethyl)adipate (2)

(BAEA) from the reaction of bis(2-chloroethyl)adipate (1) with sodium azide in ethanol (72 %).

N 3

O

O

O

O

N 3

N 3

O

O

O

O

N 3

CH 2 OCOCH 2 N 3

C

CH 2 OCOCH 2 N 3

O 2 N

CH 2 OCOCH 2 N 3

CH 2 OCOCH 2 N 3

N 3 CH 2 OCOCH 2 CH 2 OCOCH 2 N 3

3

(EGBAA)

4

(DEGBAA)

5

(TMNTA)

6

(PETKAA)

O

CH 2 OCOCH 2 N 3

Figure 8.2

Drees and co-workers^7 synthesized a number of energetic azido plasticizers whose structures

are based on those of known nitrate ester plasticizers. EGBAA (3), DEGBAA (4), TMNTA (5)

and PETKAA (6) are synthesized from the corresponding chloroacetate esters with sodium

azide in DMSO.

O O

O

O

N 3

N 3

N 3

N 3

7

O

O

N 3 N 3

8

N 3 O

O

O

O

N 3

N 3

N 3 9

Figure 8.3

Several other azido esters has been reported, including (7),^5 (8)^8 and (9),^9 which are syn-

thesized along similar routes of ester formation followed by substitution of halogen with azide

anion or in the reverse order.