Hexamethyleneimine

Base Information

• Chemical Name: Hexamethyleneimine
• CAS No.: 111-49-9
• Molecular Formula: C6H13N
• Molecular Weight: 99.1759
• Hs Code.: 2933.90
• European Community (EC) Number: 203-875-9
• NSC Number: 16236
• UN Number: 2493
• UNII: CZD076G73R
• DSSTox Substance ID: DTXSID1026879
• Nikkaji Number: J22.113I
• Wikipedia: Azepane
• Wikidata: Q421530
• Metabolomics Workbench ID: 54644
• ChEMBL ID: CHEMBL1375444
• Mol file: 111-49-9.mol

Synonyms:hexahydroazepine;hexahydroazepine hydrochloride;perhydroazepine

Chemical Property of Hexamethyleneimine

Chemical Property:

• Appearance/Colour: clear liquid with ammonia-like odor
• Vapor Pressure: 7.4 mm Hg ( 21.1 °C)
• Melting Point: -37 °C
• Refractive Index: 1.463
• Boiling Point: 142.666 °C at 760 mmHg
• PKA: pK1:11.07 (25°C)
• Flash Point: 18.333 °C
• PSA: 12.03000
• Density: 0.825 g/cm³
• LogP: 1.47880
• Storage Temp.: Poison room
• Water Solubility.: soluble
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 99.104799419
• Heavy Atom Count: 7
• Complexity: 37.4
• Transport DOT Label: Flammable Liquid Corrosive

Purity/Quality:

Hexamethylenimine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F; T+
• Hazard Codes: T,T+,F
• Statements: 10-20-25-34-28-11
• Safety Statements: 26-36/37/39-45-28A-16-1

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Cyclic
• Canonical SMILES: C1CCCNCC1
• Uses: A degradation product of herbicide Molinate in pot soil and rice plants. 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.

Technology Process of Hexamethyleneimine

There total 90 articles about Hexamethyleneimine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.0%

α-hydromuconic acid (2583-24-6) → hexamethylene imine (111-49-9) + ε-caprolactam (171257-01-5) + adipamide (628-94-4)

Guidance literature:

α-hydromuconic acid; With 5% palladium on Al₂O₃; ammonia; In 1,4-dioxane; at 20 ℃; for 0.5h; under 2625.26 Torr; Autoclave;

With hydrogen; In 1,4-dioxane; at 250 ℃; for 3h; under 12751.3 Torr; Autoclave;

Reference yield: 45.0%

3-hydroxyadipic acid → hexamethylene imine (111-49-9) + ε-caprolactam (171257-01-5) + adipamide (628-94-4)

Guidance literature:

3-hydroxyadipic acid; With 5% palladium on Al₂O₃; ammonia; In 1,4-dioxane; at 20 ℃; for 0.5h; under 2625.26 Torr;

With hydrogen; In 1,4-dioxane; at 250 ℃; for 3h; under 12751.3 Torr; Autoclave;

Reference yield: 23.4%

1,6-hexanediol (629-11-8) → hexamethylene imine (111-49-9) + 1,6-Hexanediamine (124-09-4) + 6-amino-1-hexanol (4048-33-3)

Guidance literature:

With ammonia; hydrogen; In water; at 180 ℃; for 4h; under 7500.75 - 27752.8 Torr; Reagent/catalyst; Solvent; Pressure; Time;

upstream raw materials:

caprolactam

1-azacycloheptane-2-thione

O-methylcaprolactim

1,6-Hexanediamine

Downstream raw materials:

N,N-Tetramethylen-hexamethyleniminium-bromid

7-(azepane-1-yl)-3,4,5,6-tetrahydro-2H-azepine

phenyl azepane-1-carboxylate

2-(1-Hexamethyleneimino)-1-phenylethanol

Refernces

• 1、 Salagre,Medina,Serra,Sueiras,Cesteros. "Nickel-magnesia catalysts: An alternative for the hydrogenation of 1,6-hexanedinitrile". . p. 202 - 209. Retrieved 2002.
• 2、 Lv, Yang,Cui, Haishuai,Liu, Pingle,Hao, Fang,Xiong, Wei,Luo, He′an. "Functionalized multi-walled carbon nanotubes supported Ni-based catalysts for adiponitrile selective hydrogenation to 6-aminohexanenitrile and 1,6-hexanediamine: Switching selectivity with [Bmim]OH". . p. 330 - 351. Retrieved 2019.
• 3、 Lv, Yang,Hao, Fang,Xiong, Shaofeng,Liu, Pingle,Luo, He'An. "Catalytic properties of nickel/sepiolite promoted with potassium and lanthanum in adiponitrile hydrogenation under mild conditions". . p. 60933 - 60939. Retrieved 2016.
• 4、 Li, Hexing,Wang, Minghui,Xu, Yeping. "Gas-phase adiponitrile hydrogenation over modified Ni-P/SiO2 amorphous catalysts". . p. 1048 - 1049. Retrieved 2000.
• 5、 -. "METHOD FOR PRODUCING HEXAMETHYLENE DIAMINE". Paragraph 0033-0055. . Retrieved 2021/02/13.
• 6、 Coeck, Robin,De Vos, Dirk E.. "One-pot reductive amination of carboxylic acids: a sustainable method for primary amine synthesis". supporting information. p. 5105 - 5114. Retrieved 2020/08/25.