Ammonia → Tatb

HRID 2358476

Reaction equation

HRID 2358476 reaction equation
C[O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[C:7]([O:12]C)[C:6]([N+:14]([O-:16])=[O:15])=[C:5]([O:17]C)[C:4]=1[N+:19]([O-:21])=[O:20].N.[C:23]1([NH2:40])[C:28]([N+:29]([O-:31])=[O:30])=[C:27]([NH2:32])[C:26]([N+:33]([O-:35])=[O:34])=[C:25]([NH2:36])[C:24]=1[N+:37]([O-:39])=[O:38]>>[N+:9]([C:8]1[C:3]([OH:2])=[C:4]([N+:19]([O-:21])=[O:20])[C:5]([OH:17])=[C:6]([N+:14]([O-:16])=[O:15])[C:7]=1[OH:12])([O-:11])=[O:10].[C:23]1([NH2:40])[C:24]([N+:37]([O-:39])=[O:38])=[C:25]([NH2:36])[C:26]([N+:33]([O-:35])=[O:34])=[C:27]([NH2:32])[C:28]=1[N+:29]([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 222Ammonia3×HCID 18286TatbHCID 113127111,3,5-Trimethoxy-2,4,6-trinitrobenzene

Product 2

HCID 18286TatbHCID 4555524Trinitrophloroglucinol

Procedure

One method of synthesizing TATB from phloroglucinol is described in GB 2355715. Phloroglucinol, also known as 1,3,5-trihydroxybenzene, is nitrated using sodium nitrite and nitric acid, forming trinitrophloroglucinol (“TNPG”), which is also known as 1,3,5-trihydroxy-2,4,6-trinitrobenzene. The nitric acid is added sequentially or in multiple additions. When cooled, a solid is produced, which is filtered, washed with 3 M hydrochloric acid (“HCl”), and dried, yielding a solid product that is a monohydrate of TNPG. The monohydrate of TNPG is a free-flowing solid. The TNPG is alkoxylated using a trialkyl orthoformate, such as trimethyl orthoformate, forming 1,3,5-trimethoxy-2,4,6-trinitrobenzene. Methanol and methyl formate are also formed and are removed by distillation. The solution of 1,3,5-trimethoxy-2,4,6-trinitrobenzene is concentrated, yielding 1,3,5-trimethoxy-2,4,6-trinitrobenzene as a solid, which is recrystallized from ethanol. The purified 1,3,5-trimethoxy-2,4,6-trinitrobenzene is then aminated using liquid ammonia or gaseous ammonia, filtered, washed with N-methylpyrrolidinone and methanol, and dried, yielding crystals of the TATB. To conduct the amination reaction, a solution of the 1,3,5-trimethoxy-2,4,6-trinitrobenzene is cooled to −10° C. and ammonia gas is introduced. If liquid ammonia is used, the animation reaction is conducted at room temperature and a pressure of 8-9 bar, or at atmospheric pressure and −33° C. If gaseous ammonia is used, the animation reaction is conducted at atmospheric pressure or at a pressure of 8-9 bar. At higher temperatures, the method is described as being less energy efficient. The TATB synthesis utilizes multiple drying and isolation acts to produce solid products of TNPG, TETNB, and TATB.

Workup

  1. customis recrystallized from ethanol
  2. filtrationfiltered
  3. washwashed with N-methylpyrrolidinone and methanol
  4. customdried
  5. customyielding crystals of the TATB
  6. customthe amination reaction
  7. customthe animation reaction
  8. customis conducted at room temperature
  9. customat atmospheric pressure and −33° C
  10. customthe animation reaction
  11. customutilizes multiple drying

Sources & evidence

ORD record
ord-fb27e47e4b334fbcbd65a33c2c7474f7
Source dataset
uspto-grants-2010_07
Patent number
US07763753B1

Linked notes

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