111-49-9

Usage

Uses

1. Used in Pharmaceutical Industry:
Hexamethyleneimine is used as a pharmaceutical product and raw material for the synthesis of various drugs and medications. It serves as an intermediate in the production of pharmaceutical compounds due to its unique chemical properties.
2. Used in Rubber Industry:
Hexamethyleneimine is utilized as a raw material in the rubber industry for the production of rubber products. Its chemical structure allows it to be a valuable component in the manufacturing process of rubber materials.
3. Used in Agrochemicals:
Hexamethyleneimine serves as an intermediate in the synthesis of agrochemicals, which are chemicals used in the agricultural industry to enhance crop production and protect plants from pests and diseases.
4. Used in Zeolite Production:
Hexamethyleneimine is used in the production of zeolites, which are microporous alkali metal aluminosilicate minerals. Zeolites have various applications, including water purification, gas separation, and as catalysts in the petrochemical industry.
5. Used in Dye and Ink Manufacturing:
Hexamethyleneimine is employed as an intermediate in the manufacturing of dyes and inks, contributing to the development of vibrant and long-lasting colorants for various applications.
6. Used in Rubber Chemicals:
As an intermediate, hexamethyleneimine is used in the production of rubber chemicals, which are additives that improve the properties of rubber materials, such as durability, flexibility, and resistance to wear.
7. Used in Textile Chemicals:
Hexamethyleneimine is utilized in the textile industry as an intermediate for the synthesis of textile chemicals, which are used to enhance the quality, appearance, and performance of textile products.
8. Used in Corrosion Inhibitors:
Hexamethyleneimine is used in the development of corrosion inhibitors, which are chemicals that protect metals from corrosion and extend their service life.
9. Used in Ore Flotation:
Hexamethyleneimine is employed in the mining industry as an intermediate in the production of chemicals used in ore flotation, a process that separates valuable minerals from waste material.
10. Used in Environmental Applications:
Hexamethyleneimine is a degradation product of the herbicide Molinate, which is used in pot soil and rice plants. Its presence in the environment indicates its potential role in the breakdown and degradation of certain herbicides, contributing to a more sustainable agricultural ecosystem.

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

Highlyflammable

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.]

InChI:InChI=1/C6H13N/c1-2-4-6-7-5-3-1/h7H,1-6H2/p+1

Upstream product

• 105-60-2 caprolactam 
• 7203-96-5 1-azacycloheptane-2-thione 
• 2525-16-8 O-methylcaprolactim 
• 124-09-4 1,6-Hexanediamine 
• 16036-99-0 6-(ethylamino)hexyl chloride 
• 26342-09-6 6-amino-1-bromo-n-hexane 
• 119026-21-0 6-iodo-hexylamine 
• 111-69-3 hexanedinitrile 
• 17721-45-8 1-tosylazepane 
• 1192-95-6 hexahydro-1-methyl-1H-azepine 
• 2228-79-7 1,5,6,7-Tetrahydro-2H-azepin-2-one 
• 4048-33-3 6-amino-1-hexanol 
• 13093-04-4 N,N'-dimethyl-1,6-hexanediamine 
• 53563-25-0 hexamethyleneiminium hexamethyleneiminothiocarbamate 

Downstream Products

• 4048-33-3 6-amino-1-hexanol 
• 6052-48-8 S-Morpholinothiocarbonyl-N,N-hexamethylen-sulfenamid 
• 14992-07-5 1-[1,3-bis-(4-chloro-benzyl)-2-oxo-2λ⁵-[1,3,2]diazaphosphinan-2-yl]-azepane 
• 36146-44-8 2-azepan-1-yl-3-[(2-oxo-oxazolidin-3-ylimino)-methyl]-pyrido[1,2-a]pyrimidin-4-one 
• 17386-25-3 1-(2-phenyl-thiazol-4-ylmethyl)-azepane 
• 17386-11-7 4-azepan-1-ylmethyl-thiazol-2-ylamine 
• 13929-37-8 Rifamycin-B-hexamethylenimid 
• 24489-20-1 azepane-1-carboxylic acid 4-[2-(5-methyl-isoxazole-3-carbonylamino)-ethyl]-benzenesulfonylamide 
• 89516-64-3 3-(2,4-dichlorobenzyl)-5-(N-hexamethyleniminomethyl)-1-phenylthiobarbituric acid 
• 97051-09-7 3-(4-Azepan-1-yl-but-2-ynyl)-5-phenyl-3H-[1,3,4]thiadiazol-2-one; hydrochloride 
• 97064-77-2 3-(4-Azepan-1-yl-but-2-ynyl)-5-(4-chloro-phenyl)-3H-[1,3,4]thiadiazol-2-one; hydrochloride 
• 97051-15-5 3-(4-Azepan-1-yl-but-2-ynyl)-5-(4-nitro-phenyl)-3H-[1,3,4]thiadiazol-2-one; hydrochloride 
• 84459-65-4 1-[4-(5-Phenyl-[1,3,4]thiadiazol-2-ylsulfanyl)-but-2-ynyl]-azepane 
• 83108-19-4 1-{4-[5-(4-Chloro-phenyl)-[1,3,4]thiadiazol-2-ylsulfanyl]-but-2-ynyl}-azepane 

Related news

Synthesis and NMR characterization of SAPO-35 from non-aqueous systems using Hexamethyleneimine (cas 111-49-9) template08/29/2019

SAPO-35 was synthesized using hexamethyleneimine template in non-aqueous systems. X-ray diffraction and scanning electron micrograph analysis shows the synthesized sample is pure and well crystalline. Presence of four stages (1.6%, 0.8%, 7.8% and 8.4%) of weight loss is observed by TG/DTA analys...detailed

Synthesis and characterization of MCM-49/ZSM-35 composite zeolites in the Hexamethyleneimine (cas 111-49-9) and cyclohexamine system08/28/2019

A novel route for synthesis of MCM-49/ZSM-35 composite zeolites with different compositions in a mixed amine system containing hexamethyleneimine (HMI) and cyclohexamine (CHA) has been developed. Furthermore, both MCM-49 zeolite and ZSM-35 zeolite can be successfully synthesized by adjusting the...detailed

Synthesis, characterization and catalytic properties of a LEV type silicoaluminophosphate molecular sieve, SAPO-35 from aqueous media using aluminium isopropoxide and Hexamethyleneimine (cas 111-49-9) template08/27/2019

A small-pore silicoaluminophosphate molecular sieve, SAPO-35 was synthesized using hexamethyleneimine template and aluminium isopropoxide as aluminium source in aqueous media is reported for the first time. Pure, highly crystalline samples were obtained in short period (96 h). The samples crysta...detailed

Hexamethyleneimine (cas 111-49-9) and pivalonitrile as location probe molecules of Lewis acid sites on MWW-type zeolites08/26/2019

Locations of Lewis acid sites (LASs) on three MWW-type zeolites, the conventional Al-containing MWW zeolite (Al-MWW), acid-treated Al-containing MWW zeolite (Al-MWW-AT) and interlayer-expanded Al-containing MWW zeolite (Al-IEZ-MWW), were clarified by IR method using hexamethyleneimine (HMI), piv...detailed

Synthesis of SAPO-16 molecular sieve in non-aqueous medium by microwave method using Hexamethyleneimine (cas 111-49-9) as a template08/23/2019

An Aluminophosphate with sequence number Six Teen (AST) type framework silico alumino phosphate (SAPO-16) molecular sieve is successfully synthesized through an eco-friendly, economic and a faster crystallization method by microwave treatment. In the present investigation, SAPO-16 is synthesized...detailed

Synthesis and characterization of platinum(II) and (IV) complexes containing Hexamethyleneimine (cas 111-49-9) ligand: crystal structure of [PtII(Hexamethyleneimine (cas 111-49-9))2(cyclobutanedicarboxylato)]·H2O08/22/2019

A series of new platinum(II) and platinum(IV) complexes of the type [PtII(HMI)2X] (where HMI=hexamethyleneimine, X=dichloro, sulfato, 1,1-cyclobutanedicarboxylato [CBDCA], oxalato, methylmalonato, or tatronato) and [PtIV(HMI)2Y2Cl2] (where Y=hydroxo, acetato, or chloro) were synthesized and char...detailed

Volumetric properties of Hexamethyleneimine (cas 111-49-9) and of its mixtures with water08/21/2019

Densities of pure hexamethyleneimine and of its aqueous solutions have been measured at atmospheric pressure, using an Anton Paar digital vibrating tube densimeter, from 273.16 to 363.15 K and from 283.15 to 353.15 K, respectively. Acceptable representations of experimental data are found using ...detailed

Study on the oxidation transformation of Hexamethyleneimine (cas 111-49-9) in a confined region of zeolites08/20/2019

Two kinds of zeolites (mordenite and AlPO4-5, with MOR and AFI topology, respectively) have been synthesized using hexamethyleneimine (HMI) as structure directing agent. It is found that HMI is incorporated intact in its protonated form in MOR and AFI. Furthermore, the oxidation of HMI restricte...detailed

Relevant academic research and scientific papers

Reductive amination of 1,6-hexanediol with Ru/Al2O3 catalyst in supercritical ammonia

Hexamethylenediamine (HMDA) is an important reagent for the synthesis of Nylon-6,6, and it is usually produced by the hydrogenation of adiponitrile using a toxic reagent of hydrocyanic acid. Herein, we developed an environmental friendly route to produce HMDA via catalytic reductive amination of 1,6-hexanediol (HDO) in the presence of hydrogen. The activities of several heterogeneous metal catalysts such as supported Ni, Co, Ru, Pt, Pd catalysts were screened for the present reaction in supercritical ammonia without any additives. Among the catalysts examined, Ru/Al2O3 presented a high catalytic activity and highest selectivity for the desired product of HMDA. The high performance of Ru/Al2O3 was discussed based on the Ru dispersion and the surface properties like the acid-basicity. In addition, the reaction parameters such as reaction temperature, time, H2 and NH3 pressure were examined, and the reaction processes were discussed in detail.

Nickel-magnesia catalysts: An alternative for the hydrogenation of 1,6-hexanedinitrile

Two Ni-MgO systems were synthesized and characterized as Ni catalysts for the hydrogenation of 1,6-hexanedinitrile (adiponitrile) in the gas phase. All three catalysts displayed high selectivity to 1,6-hexanediamine, for a total conversion with a maximum

Improved catalytic performance of acid-activated sepiolite supported nickel and potassium bimetallic catalysts for liquid phase hydrogenation of 1,6-hexanedinitrile

Different inorganic acids were used to activate sepiolite, and the acid-activated sepiolites supported nickel and potassium bimetallic catalysts were prepared. Nitrogen adsorption-desorption, hydrogen chemisorption, ammonia temperature programmed desorption (NH3-TPD), temperature programmed reduction (TPR), powder X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), Fourier Transform Infrared Spectroscopy (FTIR) and energy dispersive X-ray (EDX) were used to characterize the catalysts. The catalytic performance of the acid-activated sepiolite supported K-Ni bimetallic catalysts were investigated in 1,6-hexanedinitrile (HDN) hydrogenation in liquid phase. It was revealed that the potassium could increase the alkalinity of the catalyst with the aim of inhibiting the formation of the 1-azacycloheptane (ACH). And the addition of potassium reduces the particle size of nickel and improves its dispersion. Compared with hydrochloric acid and sulfuric acid, nitric acid treatment increases more silanol groups (Si[sbnd]OH) on the sepiolite surface, which is helpful to nickel particles adsorption and dispersion. Nitric acid activated sepiolite supported nickel and potassium bimetallic catalysts (K-Ni/NASEP) present the best catalytic performance, the conversion of HDN comes up to 92.0% under moderate conditions of lower temperature and pressure, the selectivity to 6-aminocapronitrile (ACN) and 1,6-hexanediamine (HDA) is up to 95.2%.

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

Functionalized multi-walled carbon nanotubes supported nickel-based catalysts were prepared and applied in adiponitrile (ADN) hydrogenation. The characterization results show that different functional groups such as NH2– COOH– OH– on MWCNTs surface can effectively act on metal ions by electrostatic attractions and chemical interactions so as to provide nucleation sites, and N species in MWCNTs can act as active sites for Ni deposition due to the strong electronic interactions between N species and Ni so as to promote ultra-small Ni nanoparticles formation, decrease NiO reduction activation energy, increase zero-valent Ni amounts as well as Ni nanoparticles dispersion. Furthermore, the doped N increases the lewis basicity, which favors the formation of primary amine of 6-aminohexanenitrile (ACN) and 1,6-hexanediamine (HDA). Moreover, the basic ionic liquid [Bmim]OH may switch the selectivity by inhibiting nucleophilic addition of the primary amine to the α-carbon of aldimine via the stabilization of –NH2 groups in the amino-imine intermediates so as to impede by-products formation. In addition, the mechanism for ADN hydrogenation in [Bmim]OH was studied by density functional theory calculations. Under optimized conditions, it gives 97.80% total selectivity to ACN and HDA at 95.34% ADN conversion over Ni/N-MWCNTs-800 in the presence of [Bmim]OH.

Catalytic properties of nickel/sepiolite promoted with potassium and lanthanum in adiponitrile hydrogenation under mild conditions

Ni/sepiolite, potassium and (or) lanthanum doped Ni/sepiolite catalysts were prepared by the incipient impregnation method and characterized by N2 adsorption-desorption, temperature programmed reduction (TPR), hydrogen chemisorption, powder X-ray diffraction (XRD), ammonia temperature programmed desorption (NH3-TPD), transmission electron microscopy (TEM) and scanning electron microscopy (SEM). It was revealed that the potassium could inhibit the formation of the ACH by-product by neutralizing some acid sites on the catalyst, and the lanthanum could efficiently reduce the diameter and improve the dispersion of the active nickel particles. These catalysts were tested in liquid phase hydrogenation of adiponitrile (ADN). The products include 6-aminocapronitrile (ACN), hexamethylenediamine (HMDA), 1-azacycloheptane (ACH) and C12 compounds. It shows that the catalyst doped with potassium and lanthanum gives the best catalytic performance, the selectivity to ACN and HMDA reaches to 91.32% at 92.56% conversion of adiponitrile under 393 K and 2.0 MPa.

Liquid phase hydrogenation of adiponitrile over directly reduced Ni/SiO2 catalyst

Liquid phase hydrogenation of adiponitrile (ADN) to 6-aminocapronitrile (ACN) and hexamethylenediamine (HMD) was investigated on Ni/SiO2 catalysts prepared under different conditions. In this reaction, the highly reactive imine intermediate forms condensation byproducts by reacting with the primary amine products (ACN and HMD). A highly dispersed Ni/SiO2 catalyst prepared by the direct reduction of Ni(NO3)2/SiO2 was found to suppress the condensation reactions by promoting the hydrogenation of adsorbed imine, and it gave excellent hydrogenation activity and primary amine selectivity. Addition of NaOH increased the primary amine selectivity to 79% at the ADN conversion of 86%.

Gas-phase adiponitrile hydrogenation over modified Ni-P/SiO2 amorphous catalysts

Gas-phase hydrogenation of adiponitrile was carried out in a fixed-bed reactor at 1 atm pressure, and in the absence of ammonia. In comparison with other Ni-based catalysts, the Ni-P/SiO2 amorphous catalyst exhibited higher activity and/or better selectivity to 1,6-hexanediamine, which could be further improved by W or MgO-additives.

Surface Characterization and Hydrogenation Properties of Several Nickel/α-Alumina Catalysts

Studies of the chemical preparation, X-ray photoelectron spectra (XPS), activation energies of reduction, temperature-programmed reduction (TPR), X-ray diffraction (XRD) and catalytic activities of several nickel/α-alumina catalysts have been caried out for the catalytic hydrogenation of hexanedinitrile, in a continuous process at 1 atm pressure, 443 K, and in the absence of ammonia.XPS results show complete reduction of non-stoichiometric NiO on α-alumina at temperatures higher than 623 K and higher surface nickel dispersion with increasing nickel content anddecreasing reduction temperatures.Activation energies of reduction for the α-alumina-supported non-stoichiometric NIO were higher than those of the unsupported non-stoichiometric NiO.TPR results show that the initial and final temperatures of reduction of the α-alumina-supported nonstoichiometric NiO are higher with unsupported NiO, confirming the inhibiting effect of α-alumina on NiO reduction.XRD measurements show the presence of α-alumina, NiO and Ni phases, and also the increase in crystallite size with increasing reduction temperature.Catalytic conversions increase with the nickel content and selectivities toward 6-aminohexanenitrile increase at lower nickel contents, high space velocities, and higher metallic sintering, probably owing to the presence of a higher content of specific crystal sites responsible for the production of 6-aminohexanenitrile.A mechanism is proposed.

METHOD FOR PRODUCING HEXAMETHYLENE DIAMINE

To provide a method for producing hexamethylene diamine from 1,6-hexanediol and ammonia, under easy-to-control mild conditions.SOLUTION: A method for producing hexamethylene diamine includes reacting 1,6-hexanediol with ammonia in the presence of a solvent by means of a noble metal-supporting catalyst.SELECTED DRAWING: None

Efficient hydrogenation of aliphatic amides to amines over vanadium-modified rhodium supported catalyst

This work presents a highly efficient catalytic hydrogenation system developed for the selective transformation of tertiary N,N-dimethyldodecanamide and secondary azepan-2-one amides to the corresponding amines. Industrial hydrogenation catalysts Pd/Al2O3, Pt/Al2O3 and Rh/Al2O3 were modified with vanadium (V) or molybdenum (Mo) species as oxophilic centres. The modified catalysts were prepared by deposition of V or Mo precursor on supported catalysts via impregnation method. The catalysts were characterized by ICP-OES, XRD, XPS, H2-TPR, FTIR, CO-chemisorption, TEM, SEM-EDX and TGA. Modified Rh-V/Al2O3 catalyst displayed the best performance affording high yield and selectivity >95 % to the desired tertiary and secondary amines at moderate reaction conditions of T H2 0 sites and oxophilic Vδ+ sites in the bimetallic Rh-V/Al2O3 catalyst were determined to be beneficial for the selective dissociation of C[dbnd]O bond of the carboxamides into the desired amines.