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HomeProduct name listHexamethyleneimine

Hexamethyleneimine

Synonym(s):Azepane;HMI;Homopiperidine;Perhydroazepine;Hexahydro-1H-azepine

  • CAS NO.:111-49-9
  • Empirical Formula: C6H13N
  • Molecular Weight: 99.17
  • MDL number: MFCD00006934
  • EINECS: 203-875-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-10-22 18:52:18
Hexamethyleneimine Structural

What is Hexamethyleneimine?

Chemical properties

clear colorless to light yellow liquid

The Uses of Hexamethyleneimine

Hexamethyleneimine is used as a pharmaceutical product and raw material for rubber products. It is also used as a intermediate for agrochemicals, zeolites, dyes , inks, rubber chemicals, textile chemicals, corrosion inhibitors, ore flotation.

The Uses of Hexamethyleneimine

A degradation product of herbicide Molinate in pot soil and rice plants.

Definition

ChEBI: An azacycloalkane that is cycloheptane in which one of the carbon atoms is replaced by a nitrogen atom.

Production Methods

Hexamethyleneimine is produced in 84% yield by heating hexamethylenediamine at 350 ℃ in a stream of hydrogen. The catalyst, ammonium vanadate on activated alumina, is prereduced with hydrogen at 500 ℃. Residues from the industrial distillation of hexamethylenediamine can be converted into hexamethyleneimine over aluminum silicate or aluminum oxide in a stream of nitrogen. For the preparation from caprolactam]. Hexamethyleneimine can be prepared by dimerizing acrolein, reducing the product to 2- hydroxymethyltetrahydropyran, expanding the ring to give oxepane, followed by treatment with ammonia over aluminum oxide at 350 ℃.

What are the applications of Application

The most important use is the conversion of hexamethyleneimine into S-ethylhexahy- dro-1H-azepine-1-carbothioate, the selective rice herbicide Molinate (C2H5 S–CO–NC6H12 , Zeneca).

General Description

A colorless liquid with an ammonia-like odor. Flash point 65°F. Toxic by ingestion. Corrosive to metals and tissue. Combustion produces toxic oxides of nitrogen.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

Hexamethyleneimine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides.

Hazard

Toxic by ingestion, strong irritant to tissue.

Health Hazard

Inhalation of vapor irritates respiratory tract; high concentrations may cause disturbance of the central nervous system. Ingestion causes burns of mouth and stomach. Contact with concentrated vapor may cause severe eye injury. Contact with liquid causes burns of eyes and skin.

Flammability and Explosibility

Highly flammable

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Purification Methods

Purify azepane by dissolving in Et2O and adding ethanolic HCl until all the base separates as the white hydrochloride, filter, wash with Et2O and dry it (m 236o). The salt is dissolved in the minimum volume of H2O and basified to pH ~ 14 with 10N KOH. The solution is extracted with Et2O, the extract is dried over KOH, evaporated and distilled. The free base is a FLAMMABLE and TOXIC liquid, and best kept as the salt. The nitrate has m 120-123o, the picrate has m 145-147o, and the tosylate has m 76.5o (ligroin). [Müller & Sauerwald Monatsh Chem 48 727 1027, Hjelt & Agback Acta Chem Scand 18 194 1964, Beilstein 20 II 1406, 20 III/IV 1406, 20/4 V 3.]

Properties of Hexamethyleneimine

Melting point: -37°C
Boiling point: 138 °C749 mm Hg(lit.)
Density  0.88 g/mL at 25 °C(lit.)
vapor pressure  7.4 mm Hg ( 21.1 °C)
refractive index  n20/D 1.466(lit.)
Flash point: 65 °F
storage temp.  Poison room
form  Liquid
pka pK1:11.07 (25°C)
color  Clear colorless to light yellow
Odor Ammonia-like.
explosive limit 1.6-9.9%(V)
Water Solubility  soluble
BRN  1084
CAS DataBase Reference 111-49-9(CAS DataBase Reference)
NIST Chemistry Reference 1H-Azepine, hexahydro-(111-49-9)
EPA Substance Registry System 1H-Azepine, hexahydro- (111-49-9)

Safety information for Hexamethyleneimine

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Corrosion
Corrosives
GHS05
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H225:Flammable liquids
H300:Acute toxicity,oral
H314:Skin corrosion/irritation
H331:Acute toxicity,inhalation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Hexamethyleneimine

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