Advances in the Synthesis of Energetic Compounds Based on 1,2,3-Triazoles

doi:10.6023/cjoc202204010

Abstract

Energetic compounds based on 1,2,3-triazole have the features of high density, high enthalpy of formation and good thermal stability, and these compounds have been extensively studied by researchers in recent years. The latest achievements of energetic compounds based on monocyclic 1,2,3-triazole, polycyclic 1,2,3-triazole and fused ring 1,2,3-triazole are reviewed, and their preparation, sensitivities and detonation performance are also summarized in details. The results show that 1,2,3-triazole compounds have good performance and stability. These compounds show important research value and potential for application in the field of energetic materials. Finally, the development status of 1,2,3-triazole compounds is summarized and prospected, and the possible research directions of various 1,2,3-triazole energetic materials in the future are put forward, in order to provide some reference for researchers engaged in energetic materials.

Key words: 1,2,3-triazole, energetic material, synthesis, sensitivity, detonation performance, research progress

Cite this article

Zujia Lu, Jian Qin, Jinting Wu, Wenli Cao, Baolong Kuang, Jianguo Zhang. Advances in the Synthesis of Energetic Compounds Based on 1,2,3-Triazoles[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 526-554.

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Compd.^a	T_m^b/℃	T_d^c/℃	ρ^d/(g•cm^-3)	Δ_fH^e/(kJ•mol^-1)	p^f/GPa	D^g/(m•s^-1)	IS^h/J	FSⁱ/N	ESD^j/J	Method^k
1a	99	178	1.75	119.3	30.5	8366	21.5	-	-	K-J
1b*	99	201	1.69	577.1	27.0	7948	3.1	-	-	K-J
1c	112	163	1.72	1042.7	28.9	8187	5.7	-	-	K-J
1d	133	152	1.86	232.3	37.3	9082	-	-	-	K-J
1e*	-	151	1.69 (298)	-75.8	19.2	6699	40	-	-	K-J
1f*	138	149	1.77 (298)	263.2	26.8	7818	6.5	-	-	K-J
1g*	111	148	1.72 (298)	407.8	25.9	7742	40	-	-	K-J
1h*	112	162	1.71 (298)	204.2	25.4	7687	40	-	-	K-J
1i*	-	131	1.87 (298)	69.4	30.7	8231	28	-	-	K-J
2a	87	242	1.59	116.4	23.7	7596	28.9	-	-	K-J
2b*	93	224	1.59	574.0	23.1	7509	3.4	-	-	K-J
2c	90	197	1.57	1056.8	23.0	7524	6.9	-	-	K-J
2d	82	177	1.70	234.1	29.7	8320	-	-	-	K-J
2e*	145	183	1.56	1463.7	21.2	7239	28.2	-	-	K-J
3	-	105	1.80	367.0	33.0	8743	-	-	-	K-J
3b	189	230	1.51	256.8	20.4	7587	-	-	-	K-J
3c	71	187	1.50	494.5	20.9	7783	-	-	-	K-J
3d	86	147	1.51	407.7	18.6	7403	-	-	-	K-J
3e*	-	226	1.62	888.3	21.2	7765	-	-	-	K-J
3f	142	162	1.54	64.6	19.3	7282	-	-	-	K-J
3g	-45	195	1.43	684.2	19.2	7532	-	-	-	K-J
3h	92	192	1.63	600.2	22.7	7957	-	-	-	K-J
5b*	50	155	1.72 (173)	681.8	32.1	8784	3	42	0.3	5.05
5c	-	154	1.71	766.7	31.5	8800	3	42	0.5	5.05
5d*	210	220	1.71 (173)	1550.9	31.9	8860	2	14	0.3	5.05
5e*	165	185	1.74 (173)	1755.8	33.6	9013	1	18	0.2	5.05
Compd.^a	T_m^b/℃	T_d^c/℃	ρ^d/(g•cm^-3)	Δ_fH^e/(kJ•mol^-1)	p^f/GPa	D^g/(m•s^-1)	IS^h/J	FSⁱ/N	ESD^j/J	Method^k
6a*	-	210	1.92 (173)	256.1	36.7	8823	1	20	0.02	5.06
6c*	-	184	1.83 (173)	468.0	39.9	9406	1	20	0.8	5.05
6d*	-	149	1.80 (173)	531.3	40.7	9426	1	20	0.2	5.05
6e*	-	210	1.75 (173)	621.6	37.6	9337	5	6	0.1	5.05
6f*	-	185	1.68 (173)	761.9	32.6	8954	>5	20	0.2	5.05
7*	-	175	1.72 (150)	282.7	28.2	8425	<1	14~16	-	6.05
8*	-	100	1.77 (150)	276.4	29.6	8602	<1	16~18	-	6.05
TNT		295	1.65	-59.3	21.3	7303	36.6	353
RDX		210	1.8	70.7	34.9	8795	7.4	120
HMX		280	1.91	74.8	39.2	9144	7	120
CL-20		210	2.04	397.8	45.2	9706	4	94
TATB		360	1.94	-154.2	32.1	8544	50	>360

Compd.^a	T_m^b/℃	T_d^c/℃	ρ^d/(g•cm^-3)	Δ_fH^e/(kJ•mol^-1)	p^f/GPa	D^g/(m•s^-1)	IS^h/J	FSⁱ/N	ESD^j/J	Method^k
1a	99	178	1.75	119.3	30.5	8366	21.5	-	-	K-J
1b*	99	201	1.69	577.1	27.0	7948	3.1	-	-	K-J
1c	112	163	1.72	1042.7	28.9	8187	5.7	-	-	K-J
1d	133	152	1.86	232.3	37.3	9082	-	-	-	K-J
1e*	-	151	1.69 (298)	-75.8	19.2	6699	40	-	-	K-J
1f*	138	149	1.77 (298)	263.2	26.8	7818	6.5	-	-	K-J
1g*	111	148	1.72 (298)	407.8	25.9	7742	40	-	-	K-J
1h*	112	162	1.71 (298)	204.2	25.4	7687	40	-	-	K-J
1i*	-	131	1.87 (298)	69.4	30.7	8231	28	-	-	K-J
2a	87	242	1.59	116.4	23.7	7596	28.9	-	-	K-J
2b*	93	224	1.59	574.0	23.1	7509	3.4	-	-	K-J
2c	90	197	1.57	1056.8	23.0	7524	6.9	-	-	K-J
2d	82	177	1.70	234.1	29.7	8320	-	-	-	K-J
2e*	145	183	1.56	1463.7	21.2	7239	28.2	-	-	K-J
3	-	105	1.80	367.0	33.0	8743	-	-	-	K-J
3b	189	230	1.51	256.8	20.4	7587	-	-	-	K-J
3c	71	187	1.50	494.5	20.9	7783	-	-	-	K-J
3d	86	147	1.51	407.7	18.6	7403	-	-	-	K-J
3e*	-	226	1.62	888.3	21.2	7765	-	-	-	K-J
3f	142	162	1.54	64.6	19.3	7282	-	-	-	K-J
3g	-45	195	1.43	684.2	19.2	7532	-	-	-	K-J
3h	92	192	1.63	600.2	22.7	7957	-	-	-	K-J
5b*	50	155	1.72 (173)	681.8	32.1	8784	3	42	0.3	5.05
5c	-	154	1.71	766.7	31.5	8800	3	42	0.5	5.05
5d*	210	220	1.71 (173)	1550.9	31.9	8860	2	14	0.3	5.05
5e*	165	185	1.74 (173)	1755.8	33.6	9013	1	18	0.2	5.05
Compd.^a	T_m^b/℃	T_d^c/℃	ρ^d/(g•cm^-3)	Δ_fH^e/(kJ•mol^-1)	p^f/GPa	D^g/(m•s^-1)	IS^h/J	FSⁱ/N	ESD^j/J	Method^k
6a*	-	210	1.92 (173)	256.1	36.7	8823	1	20	0.02	5.06
6c*	-	184	1.83 (173)	468.0	39.9	9406	1	20	0.8	5.05
6d*	-	149	1.80 (173)	531.3	40.7	9426	1	20	0.2	5.05
6e*	-	210	1.75 (173)	621.6	37.6	9337	5	6	0.1	5.05
6f*	-	185	1.68 (173)	761.9	32.6	8954	>5	20	0.2	5.05
7*	-	175	1.72 (150)	282.7	28.2	8425	<1	14~16	-	6.05
8*	-	100	1.77 (150)	276.4	29.6	8602	<1	16~18	-	6.05
TNT		295	1.65	-59.3	21.3	7303	36.6	353
RDX		210	1.8	70.7	34.9	8795	7.4	120
HMX		280	1.91	74.8	39.2	9144	7	120
CL-20		210	2.04	397.8	45.2	9706	4	94
TATB		360	1.94	-154.2	32.1	8544	50	>360

Compd.^a	T_m^b/℃	T_d^c/℃	ρ^d/(g•cm^-3)	Δ_fH^e/(kJ•mol^-1)	p^f/GPa	D^g/(m•s^-1)	IS^h/J	FSⁱ/N	ESD^j/J	Method^k
9a	116	159	1.50	117.0	20.1	7839	>40	>360	-	6.01
9c	113	200	1.48	277.0	22.0	8188	>40	>360	-	6.01
9d	199	265	1.42	100.0	16.1	7239	>40	>360	-	6.01
9e	141	233	1.44	193.0	18.1	7612	>40	>360	-	6.01
9f	153	211	1.55	310.0	23.6	8489	>40	>360	-	6.01
9g	157	201	1.55	426.0	25.2	8724	>40	>360	-	6.01
10	278	297	1.84	134.7	35.7	8909	81.3 (cm)	-	-	K-J
10a	120	124	1.62	140.0	22.5	7945	>40	>360	-	6.01
10c	149	171	1.64	298.0	29.2	9067	>40	>360	-	6.01
10d	237	251	1.57	131.0	21.4	8066	>40	>360	-	6.01
10e	175	219	1.61	222.0	24.7	8557	>40	>360	-	6.01
10f	152	191	1.58	343.0	25.3	8676	>40	>360	-	6.01
10g	169	181	1.66	448.0	30.2	9354	>40	>360	-	6.01
11a*	-	194	1.68	130.0	28.9	8418	12.5	160	-	6.01
11b	126	178	1.86	173.0	38.0	9302	11	108	-	6.01
11d	-	221	1.70	107.0	26.3	8292	17.5	>360	-	6.01
11e*	114	206	1.71	199.0	27.6	8532	25	360	-	6.01
11f*	120	192	1.64	321.0	26.2	8436	15	80	-	6.01
11g	114	195	1.74	423.0	31.7	9129	12.5	72	-	6.01
12*	-	130	1.87	226.6	36.9	8876	3.5	-	-	5.05
12a*	-	214	1.83	159.0	35.4	9139	2.5	80	-	6.01
12b*	105	185	1.85	119.0	38.8	9464	7	64	-	6.01
12c	-	155	1.73	347.0	34.2	9505	2	80	-	6.01
12d	-	216	1.75	141.0	28.4	8639	10	288	-	6.01
12e	176	187	1.57	329.0	24.1	8405	10	>360	-	6.01
12f	147	200	1.58	594.0	26.7	8814	15	>360	-	6.01
12g	-	205	1.65	466.0	28.3	8799	2	72	-	6.01
13	169	-	1.58	125.1	20.8	7497	>40	-	-	5.05
14	-	112	1.74	196.1	30.0	8350	25	-	-	5.05
15	-	149	1.77	523.0	32.9	8669	4	-	-	5.05
15a	-	136	1.65	488.0	30.2	8856	3.5	64	-	6.01
15c	-	115	1.63	649.0	29.6	8884	4	96	-	6.01
15d*	-	142	1.60	476.0	23.8	8229	4	56	-	6.01
Compd.^a	T_m^b/℃	T_d^c/℃	ρ^d/(g•cm^-3)	Δ_fH^e/(kJ•mol^-1)	p^f/GPa	D^g/(m•s^-1)	IS^h/J	FSⁱ/N	ESD^j/J	Method^k
15e	-	112	1.63	566.0	26.2	8611	4	144	-	6.01
15f	-	110	1.59	686.0	26.4	8646	2	80	-	6.01
15g	-	102	1.60	796.0	28.1	8896	7.5	120	-	6.01
16	124	-	1.65	493.9	26.3	8096	8	-	-	5.05
17	132	141	1.75	594.6	33.0	8756	3	-	-	5.05
18	79	-	1.70	174.0	28.5	8126	35	-	-	5.05
19*	94	190	1.83	274.6	36.2	8843	24	-	-	5.05
20*	-	-	1.72 (150)	-	-	-	-	-	-	6.01
21*	-	212	1.73	229.3	28.0	8511	26	240	-	6.01
22*	190	194	1.71	242.2	27.4	8451	7	120	-	6.01
TNT		295	1.65	-59.3	21.3	7303	36.6	353
RDX		210	1.8	70.7	34.9	8795	7.4	120
HMX		280	1.91	74.8	39.2	9144	7	120
CL-20		210	2.04	397.8	45.2	9706	4	94
TATB		360	1.94	-154.2	32.1	8544	50	>360

Compd.^a	T_m^b/℃	T_d^c/℃	ρ^d/(g•cm^-3)	Δ_fH^e/(kJ•mol^-1)	p^f/GPa	D^g/(m•s^-1)	IS^h/J	FSⁱ/N	ESD^j/J	Method^k
9a	116	159	1.50	117.0	20.1	7839	>40	>360	-	6.01
9c	113	200	1.48	277.0	22.0	8188	>40	>360	-	6.01
9d	199	265	1.42	100.0	16.1	7239	>40	>360	-	6.01
9e	141	233	1.44	193.0	18.1	7612	>40	>360	-	6.01
9f	153	211	1.55	310.0	23.6	8489	>40	>360	-	6.01
9g	157	201	1.55	426.0	25.2	8724	>40	>360	-	6.01
10	278	297	1.84	134.7	35.7	8909	81.3 (cm)	-	-	K-J
10a	120	124	1.62	140.0	22.5	7945	>40	>360	-	6.01
10c	149	171	1.64	298.0	29.2	9067	>40	>360	-	6.01
10d	237	251	1.57	131.0	21.4	8066	>40	>360	-	6.01
10e	175	219	1.61	222.0	24.7	8557	>40	>360	-	6.01
10f	152	191	1.58	343.0	25.3	8676	>40	>360	-	6.01
10g	169	181	1.66	448.0	30.2	9354	>40	>360	-	6.01
11a*	-	194	1.68	130.0	28.9	8418	12.5	160	-	6.01
11b	126	178	1.86	173.0	38.0	9302	11	108	-	6.01
11d	-	221	1.70	107.0	26.3	8292	17.5	>360	-	6.01
11e*	114	206	1.71	199.0	27.6	8532	25	360	-	6.01
11f*	120	192	1.64	321.0	26.2	8436	15	80	-	6.01
11g	114	195	1.74	423.0	31.7	9129	12.5	72	-	6.01
12*	-	130	1.87	226.6	36.9	8876	3.5	-	-	5.05
12a*	-	214	1.83	159.0	35.4	9139	2.5	80	-	6.01
12b*	105	185	1.85	119.0	38.8	9464	7	64	-	6.01
12c	-	155	1.73	347.0	34.2	9505	2	80	-	6.01
12d	-	216	1.75	141.0	28.4	8639	10	288	-	6.01
12e	176	187	1.57	329.0	24.1	8405	10	>360	-	6.01
12f	147	200	1.58	594.0	26.7	8814	15	>360	-	6.01
12g	-	205	1.65	466.0	28.3	8799	2	72	-	6.01
13	169	-	1.58	125.1	20.8	7497	>40	-	-	5.05
14	-	112	1.74	196.1	30.0	8350	25	-	-	5.05
15	-	149	1.77	523.0	32.9	8669	4	-	-	5.05
15a	-	136	1.65	488.0	30.2	8856	3.5	64	-	6.01
15c	-	115	1.63	649.0	29.6	8884	4	96	-	6.01
15d*	-	142	1.60	476.0	23.8	8229	4	56	-	6.01
Compd.^a	T_m^b/℃	T_d^c/℃	ρ^d/(g•cm^-3)	Δ_fH^e/(kJ•mol^-1)	p^f/GPa	D^g/(m•s^-1)	IS^h/J	FSⁱ/N	ESD^j/J	Method^k
15e	-	112	1.63	566.0	26.2	8611	4	144	-	6.01
15f	-	110	1.59	686.0	26.4	8646	2	80	-	6.01
15g	-	102	1.60	796.0	28.1	8896	7.5	120	-	6.01
16	124	-	1.65	493.9	26.3	8096	8	-	-	5.05
17	132	141	1.75	594.6	33.0	8756	3	-	-	5.05
18	79	-	1.70	174.0	28.5	8126	35	-	-	5.05
19*	94	190	1.83	274.6	36.2	8843	24	-	-	5.05
20*	-	-	1.72 (150)	-	-	-	-	-	-	6.01
21*	-	212	1.73	229.3	28.0	8511	26	240	-	6.01
22*	190	194	1.71	242.2	27.4	8451	7	120	-	6.01
TNT		295	1.65	-59.3	21.3	7303	36.6	353
RDX		210	1.8	70.7	34.9	8795	7.4	120
HMX		280	1.91	74.8	39.2	9144	7	120
CL-20		210	2.04	397.8	45.2	9706	4	94
TATB		360	1.94	-154.2	32.1	8544	50	>360

Compd.^a	T_m^b/℃	T_d^c/℃	ρ^d/(g•cm^-3)	Δ_fH^e/(kJ•mol^-1)	p^f/GPa	D^g/(m•s^-1)	IS^h/J	FSⁱ/N	ESD^j/J	Method^k
24a*	-	131	2.04 (296)	-135.0	28.3	8715	1	60	-	6.02
25*	83	142	1.73 (296)	564.0	30.8	8619	1.25	32	-	6.02
TNT		295	1.65	-59.3	21.3	7303	36.6	353
RDX		210	1.8	70.7	34.9	8795	7.4	120
HMX		280	1.91	74.8	39.2	9144	7	120
CL-20		210	2.04	397.8	45.2	9706	4	94
TATB		360	1.94	-154.2	32.1	8544	50	>360

1,2,3-三唑类含能化合物的合成研究进展