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Hexamethylenediamine is used in organic synthesis and polymerization of high molecular compounds.
Hexamethylenediamine is mainly used in the production of polyamide, such as nylon 66, Nylon 610, etc.
Hexamethylenediamine also used in the synthesis of diisocyanate, and used as urea-formaldehyde resin, epoxy resin curing agent, organic crosslinking agent.
CAS Number: 124-09-4
EC Number (EINECS): 204-679-6
MDL Number: MFCD00008243
IUPAC Name: Hexane-1,6-diamine (sometimes written 1,6-hexanediamine)
Molecular Formula: C₆H₁₆N₂
Molecular Weight: 116.2-116.21 g/mol
SYNONYMS:
HMDA, HMD, 1,6-Hexanediamine, 1,6-Diaminohexane, 1,6-Hexanediamine, 1,6-Hexylenediamine, Hexamethylendiamine, 1,6-Hexamethylenediamine, Hexylenediamine, NCI-C61405, Hexane-1,6-diamine, 1,6-Diaminohexane, 1,6-Hexanediamine, HEXAMETHYLENEDIAMINE, 1,6-Hexanediamine, 1,6-Diaminohexane, Hexane-1,6-diamine, HMDA, HMD, Dytek® HMD, 1,6-Diaminohexane, 1,6-Hexanediamine, HMDA, 1,6-Hexanediamine, Hexamethylenediamine, 124-09-4, HEXANE-1,6-DIAMINE, HMDA, 1,6-Hexylenediamine, HEXAMETHYLENE DIAMINE, 1,6-Diamino-n-hexane, diaminohexane, Hexane, 1,6-diamino-, NCI-C61405, HEX-NH2, NSC 9257, CCRIS 6224, H2N(CH2)6NH2, HSDB 189, UNII-ZRA5J5B2QW, EINECS 204-679-6, BRN 1098307, DTXSID5024922, AI3-37283, NSC-9257, HEXANEMETHYLENEDIAMINE-, DTXCID604922, CHEBI:39618, EC 204-679-6, 4-04-00-01320 (Beilstein Handbook Reference), RefChem:7518, HMD(A), 204-679-6, 1,6-Hexamethylenediamine, Hexylenediamine, MFCD00008243, ZRA5J5B2QW, CHEMBL303004, 6-aminohexylamine, HEXAMETHYLENE-1,6-13C2-DIAMINE, 1,6-DIAMINO(HEXANE-2,2,5,5-D4), 1,6-Diaminohexane-d12 dihydrochloride, 16D, CAS-124-09-4, vegetable-oil, N,N'-hexanediylbis-Amides, 1,6-Hexandiamine, vegetable oil fatty acids diamide vegetable-oil, n,n'-hexanediylbis-amide Amides, vegetable-oil, N,N'-hexanediylbis-, 1,6-Hexandiamine, vegetable oil fatty acids diamide, UN1783, UN2280, 1,6diaminohexane, 1,6 diaminohexane, 1.6-diaminohexane, 1,6-diamino hexane, 1,6-hexamethylenediamine, Hexamethylenediamine, solid, Hexamethylenediamine, 98%, 1,6-Diaminohexane, 2HCl, WLN: Z6Z, Hexamethylenediamine, solid, NCIOpen2_002722, SCHEMBL15085, UN 1783, (Salt/Mix), SCHEMBL421078, SCHEMBL654031, SCHEMBL893396, SCHEMBL2821952, SCHEMBL3122863, SCHEMBL3495284, SCHEMBL6248244, SCHEMBL7090279, SCHEMBL7517212, 1,6-HEXANEDIAMINE [MI], NSC9257, BB_NC-02277, HEXAMETHYLENE DIAMINE [HSDB], Tox21_202088, Tox21_303123, BBL027705, BDBM50323740, EBC-03090, MSK002130, SBB059999, STL281875, AKOS000118875, DB03260, FH16093, UN 2280, MSK002130-1000A, NCGC00091677-01, NCGC00091677-02, NCGC00257104-01, NCGC00259637-01, BP-14170, BP-21415, VS-08580, Hexamethylenediamine, technical grade, 70%, D0095, NS00001449, ST45255381, EN300-19313, G77311, AG-690/11351767, AG-690/11351768, F493072, Hexamethylenediamine, SAJ first grade, >=98.0%, Q424936, Hexamethylenediamine, solid [UN2280] [Corrosive], Hexane-1,6-diamine 100 microg/mL in Acetonitrile, 1,6-Hexanediamine Solution in Acetonitrile, 1000 ug/mL, Z104473514, InChI=1/C6H16N2/c7-5-3-1-2-4-6-8/h1-8H, 1,6-diamino-hexan, 1,6-Hexamethylenediamine, H2N(CH2)6NH2, hexamethylenediamine (1,6-hexanediamine), hexamethylenediamine, solid, Hexylenediamine, NCI-C61405, Hexamethylendiamine, 1,6-Hexanediamine, 1,6-Diaminohexane, Hexamethylenediamine, HMDA, 1,6-Hexylenediamine, 1,6-Diamino-n-hexane, Hexylenediamine, α,ω-Hexanediamine, V 1, Hi Perm, NSC 9257, 80HMD, Advancure, RT Advancure HD, Dytek 70, 6-Aminohexylamine, Dytek HMD, 1,6-Hexanediamine, Hexamethylenediamine, HMDA, 1,6-Diamino-n-Hexane, 1,6-Diaminohexane, 1,6-Hexylenediamine, H2N(CH2)6NH2, 1,6-Hexamethylenediamine, NCI-C61405, Hexylenediamine, HMDA, NCI-C61405, H2N(CH2)6NH2, Hexylenediamine, 1,6-Hexanediamine, 1,6-diamino-hexan, 1,6-Diaminohexane, hexane-1,6-diamine, Hexamethylendiamine, hexane-1,6-diaminium, Hexamethylenediamine, cyclohexane diammoniate, 1,6-Hexamethylenediamine, hexamethylenediamine, solid, 6-aminohexan-1-aminium chloride, hexamethylenediamine (1,6-hexanediamine)
Hexamethylenediamine is an amine-based organic compound.
Hexamethylenediamine is a kind of diamine, which contains a carbon chain skeleton of hexane and amino functional groups at both ends.
Hexamethylenediamine is a colorless solid with strong ammonia odor, similar to piperidine.
Hexamethylenediamine is the organic compound with the formula H2N(CH2)6NH2.
Hexamethylenediamine is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups.
Hexamethylenediamine has a strong amine odor, similar to piperidine.
About 1 billion kilograms of Hexamethylenediamine are produced annually.
Hexamethylenediamine, solid is a colorless crystalline solid.
Hexamethylenediamine is soluble in water.
Hexamethylenediamine, solution appears as a clear colorless liquid.
Hexamethylenediamine is soluble in water.
Hexamethylenediamine is colorless crystalline solid or clear liquid.
Hexamethylenediamine, solid is a colorless crystalline solid.
Hexamethylenediamine is soluble in water.
Hexamethylenediamine, solution appears as a clear colorless liquid.
Hexamethylenediamine is a colorless crystalline solid or clear liquid.
Hexamethylenediamine (HMDA), colourless viscous liquid used in many industrial processes, particularly in plastics and rubbers.
Hexamethylenediamine that stands out from the other diamines are high outperform thermal stability and low vapor pressure making is a favourite for high-performance material.
Hexamethylenediamine is significant to reinforce resins, plastics and elastomers for applications in end products so as to demand for product durability & resilience.
Hexamethylenediamine (formally hexane-1,6-diamine) is a colorless, low-melting solid with an important industrial use.
Hexamethylenediamine and adipic acid (Molecule of the Week for February 9, 2015) are the starting materials for manufacturing nylon 6,6, a polyamide used widely in textiles and plastics.
The earliest synthesis of hexamethylenediamine is attributed to Theodor Curtius and Hans Clemm, Heidelberg University (Germany) chemists, who in 1900 made Hexamethylenediamine by hydrogenating adiponitrile.
In 1929, biochemists Karl H. Slotta and R. Tschesche at the University of Breslau (Germany) improved this process by generating hydrogen in situ from sodium metal and ethanol.
Hexamethylenediamine or 1,6-hexanediamine is a diamine with a hexamethylene hydrocarbon chain and amine functional groups at each end.
Hexamethylenediamine has a strong amine odor, similar to piperidine.
Hexamethylenediamine is produced from adiponitrile.
Hexamethylenediamine is an organic compound that is used as a precursor for the production of polyamide and polyurethane.
Hexamethylenediamine reacts with trifluoroacetic acid to form hexamethylene diamine.
The reaction mechanism involves the hydrophobic effect.
Hexamethylenediamine has been used as an antimicrobial agent in wastewater treatment and has been shown to be effective against solid tumours
Hexamethylenediamine has a hydroxyl group that can hydrogen bond with other molecules, which may help to explain its effectiveness against solid tumours.
Hexamethylenediamine (HMD) also named Hexane-1,6-diamine; 1,6-Hexanediamine or 1,6-Diaminohexane is a chemical compound with two amines functions.
Hexamethylenediamine (HMD) is obtained from hydrogenation of the adiponitrile.
Hexamethylenediamine (also called 1,6-diaminohexane and 1,6-hexanediamine) also known as hexamethylenediamine (H2N(CH2)6NH2) is a colorless solid, soluble in both water and alcohol.
Hexamethylenediamine is the second monomer used to produce nylon 6/6 with adipic acid or its esters.
The main route for the production of Hexamethylenediamine is the liquid-phase catalyzed hydrogenation of adiponitrile: NC(CH2)4CN+4H2→H2N(CH2)6NH2
Hexamethylenediamine or hexane-1,6-diamine, is the organic compound with the formula H2N(CH2)6NH2.
Hexamethylenediamine is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups.
The colorless solid (yellowish for some commercial samples), Hexamethylenediamine, has a strong amine odor.
Hexamethylenediamine is involved in the synthesis of Chlorhexidine.
Hexamethylenediamine, solid is a colorless crystalline solid.
Hexamethylenediamine is soluble in water.
Hexamethylenediamine is corrosive to metals and tissue.
Hexamethylenediamine, solution appears as a clear colorless liquid.
Hexamethylenediamine burns although some effort is required to ignite.
Hexamethylenediamine is soluble in water.
Hexamethylenediamine is a C6 alkane-alpha,-diamine.
Hexamethylenediamine has a role as a human xenobiotic metabolite.
Hexamethylenediamine derives from a hydride of a hexane.
Hexamethylenediamine, also known as 1,6-hexanediamine or HMDA, is an organic compound with the molecular formula C₆H₁₆N₂ (CAS 124-09-4) and the structure H₂N(CH₂)₆NH₂.
Hexamethylenediamine is a colorless, low-melting crystalline solid (melting point: 39–42 °C) that is highly soluble in water (up to 490 g/L) and has a boiling point of 204–205 °C.
Industrially, hexamethylenediamine is synthesized via the catalytic hydrogenation of adiponitrile, which is typically produced from butadiene via hydrocyanation.
This process, first developed in the early 20th century and refined for large-scale production, yields high-purity Hexamethylenediamine essential for polymer applications.
Hexamethylenediamine's global production exceeds millions of tons annually, driven by the nylon market valued at over $35 billion as of 2023.
Hexamethylenediamine's flash point is 85 °C, necessitating careful handling in industrial settings.
USES and APPLICATIONS of HEXAMETHYLENEDIAMINE:
Hexamethylenediamine is used for Nylon 66, polyurethane foam raw materials and epoxy resin curing agent.
Hexamethylenediamine is mostly used in the synthesis of nylon 66 and 610 resin, also used in the synthesis of polyurethane resin, ion exchange resin and hexylene diisocyanate, and used as a curing agent for urea-formaldehyde resin, epoxy resin, etc., organic crosslinking agent, etc., also used as a stabilizer for textile and paper industry, bleaching agent, aluminum alloy corrosion inhibitor and chloroprene rubber emulsifier.
Hexanediamine and hydrochloric acid salt below 28 °c to obtain 1, 6-hexanediamine hydrochloride ([6055-52-3]), can be used to produce bactericide chlorhexidine acetate.
Hexanediamine also has some applications in the production of adhesives, aviation coatings and rubber vulcanization accelerators.
Hexamethylenediamine is used in organic synthesis and polymerization of polymer compounds.
Hexamethylenediamine is mainly used in the production of polyamide, such as nylon 66, Nylon 610, etc.;
Hexamethylenediamine is also used in the synthesis of diisocyanate;
Hexamethylenediamine is used as urea-formaldehyde resin, epoxy resin curing agent, organic crosslinking agent.
Hexamethylenediamine can be produced from adiponitrile, hexanediol and caprolactam, but almost all processes for the large-scale production of hexamethylene diamine are based on adiponitrile.
Hexamethylenediamine is used organic synthesis, nylon 66 intermediate.
Hexamethylenediamine is an important organic chemical intermediate, which is mostly used as a raw material for the synthesis of polyamide, such as for the synthesis of nylon-6e salt, but also commonly used as urea resin and epoxy resin curing agent and crosslinking agent.
At present, with the development of synthetic fiber industry, the demand for Hexamethylenediamine compounds in the world is increasing, and the market demand is larger.
Hexamethylenediamine is used in organic synthesis and polymerization of high molecular compounds.
Hexamethylenediamine is mostly used for the synthesis of nylon 66 and 610 resin, also used for the synthesis of polyurethane resin, ion exchange resin and hexylene diisocyanate, also used for the preparation of crosslinking agent, adhesive, aviation coatings, epoxy resin curing agent, rubber vulcanization accelerator, and used as textile and paper industry stabilizer, bleaching agent, aluminum alloy corrosion inhibitor and neoprene emulsifier.
Hexamethylenediamine is mainly used in the production of polyamide, such as nylon 66, Nylon 610, etc.; Also used in the synthesis of diisocyanate; And used as urea-formaldehyde resin, epoxy resin curing agent, organic crosslinking agent.
Hexamethylenediamine can be produced from adiponitrile, hexanediol and caprolactam, but almost all processes for the large-scale production of
Hexamethylenediamine are based on adiponitrile.
Hexamethylenediamine serves as a key intermediate in the synthesis of chlorhexidine, a widely used antiseptic and disinfectant.
Hexamethylenediamine is incorporated through the formation of hexamethylene bridges in the reaction of hexamethylenediamine dihydrochloride with sodium dicyanamide to form hexamethylene bisdicyanoguanidine, which is then condensed with 4-chloroaniline hydrochloride to yield chlorhexidine dihydrochloride.
This application leverages the diamine structure to create the bridging moiety essential for chlorhexidine's antimicrobial properties, commonly employed in surgical scrubs, wound care, and oral hygiene products.
Beyond pharmaceuticals, hexamethylenediamine functions as a cross-linking agent in various specialty applications.
In water treatment, Hexamethylenediamine is utilized in the formulation of ion-exchange resins and antimicrobial polymers, where it reacts with epoxide groups to enhance durability and prevent biofouling in filtration systems.
Additionally, Hexamethylenediamine serves as a component in fuel additives, particularly in deposit control formulations derived from polyisobutylene succinic anhydride reactions, which help mitigate engine deposits and improve fuel stability.
In lubricants and corrosion inhibitors, hexamethylenediamine contributes to synthetic additive blends that protect metal surfaces by forming protective films, enhancing performance in industrial oils.
Hexamethylenediamine also finds use in textile finishing agents, where it is applied in treatments for flame retardancy, hydrophobicity, and crease resistance on fabrics like cotton.
For instance, Hexamethylenediamine's ammonium salts combined with phosphonic acid derivatives enable one-step finishing processes that improve fabric durability without compromising breathability.
These niche applications collectively represent a minor share of global hexamethylenediamine production, accounting for under 10% of demand, primarily overshadowed by polymer uses.
However, interest in bio-based derivatives is expanding, with research into production of renewable hexamethylenediamine from lysine fermentation, including a 2024 enzymatic cascade achieving up to 65% conversion, showing promise for sustainable antiseptics and additives.
Hexamethylenediamine is used to make nylon.
Applications of Hexamethylenediamine in the Plastic & Rubber Industry: Hexamethylenediamine is very important in the plastic and rubber industry, an essential precursor to nylon and many other polyamides, nylon is part of our daily lives and we all wear nylon from time to time due to it being the very foundation for many materials that are incredibly durable, yet also lightweight.
Hexamethylenediamine's main uses are as a raw material in the production of nylon polymers, production of hexamethylene diisocyanate (HDI) for use as monomer feedstock in polyurethane production cross-link agent in epoxy resins.
Hexamethylenediamine and adipic acid are the starting materials for nylon 6,6, which is widely used in textiles and plastics.
Hexamethylenediamine reduce yellowing in PU resin.
Hexamethylenediamine can react with the phosgene and produce the HexamethylenDiIsocyanate (HDI).
The main uses of Hexamethylenediamine are epoxy curing agents, petroleum, adhesives, inks, scale and corrosion inhibitors, water treatment chemicals and disinfectants.
Polymer production: Hexamethylenediamine is primary use is as a raw material to make nylon 6-6 via polycondensation with adipic acid.
Polyurethane industry: Precursor to hexamethylene diisocyanate (HDI) for polyurethanes.
Crosslinking agent: Hexamethylenediamine is used in epoxy resins.
Chemical intermediate: Hexamethylenediamine is used in synthesis of specialty chemicals, elastomers, fiber and plastics modifications.
Additional roles of Hexamethylenediamine include preparation of adhesives, ceramics, and certain carbamate derivatives.
Hexamethylenediamine is used almost exclusively for the production of polymers, an application that takes advantage of its structure.
Hexamethylenediamine is difunctional in terms of the amine groups and tetra functional with respect to the amine hydrogens.
The great majority of Hexamethylenediamine is consumed by the production of nylon 66 via condensation with adipic acid.
Otherwise hexamethylene diisocyanate (HDI) is generated from Hexamethylenediamine by phosgenation as a monomer feedstock in the production of polyurethane.
Hexamethylenediamine also serves as a cross-linking agent in epoxy resins.
Applications & Uses of Hexamethylenediamine: Isocyanates, Scale and corrosion inhibitors, Water treatment chemicals, Epoxy curing agents, Polyamide resins, adhesives, inks, fibers, and Petroleum additives.
Hexamethylenediamine is used to make nylon.
Hexamethylenediamine (HMDA) is a significant organic compound in the field of polymer science and materials research, primarily known for its pivotal role as a monomer in the production of nylon-6,6, among other polyamides.
Hexamethylenediamine serves as a building block, where its bifunctional nature allows for the formation of long, chain-like molecules through a condensation reaction with adipic acid, resulting in polymers characterized by high tensile strength and thermal resistance.
Beyond its application in polymer synthesis, hexamethylenediamine is also utilized in the manufacture of a wide array of industrial products, including coatings, adhesives, and certain types of resins, where its properties are leveraged to enhance durability and chemical resistance.
Its utility in research extends into the realm of materials science, where hexamethylenediamine′s reactivity and ability to form complex compounds are explored for the development of innovative materials with potential applications in various industries.
As a key aliphatic diamine, Hexamethylenediamine serves primarily as a monomer in the industrial production of nylon 6,6 through polycondensation with adipic acid, enabling the synthesis of durable polymers used in textiles, plastics, and engineering materials.
Beyond nylon, Hexamethylenediamine finds uses in polyurethanes, water treatment resins, adhesives, and specialty chemicals, leveraging its reactivity as a bifunctional amine.
-Polymer production uses of Hexamethylenediamine:
Hexamethylenediamine (HMDA) is predominantly utilized in the production of nylon 6,6, a high-performance polyamide formed through step-growth polycondensation with adipic acid.
This reaction involves the condensation of the diamine and diacid monomers, eliminating water to form amide linkages and yielding a linear polymer with repeating units.
The balanced equation for the polymerization is:
nceH2N(CH2)6NH2+nceHOOC(CH2)4COOH→[−ceNH(CH2)6NHCO(CH2)4CO−]n+2nceH2O
This process typically occurs in aqueous solution under controlled temperature and pressure conditions to form the nylon salt intermediate, followed by heating to drive polymerization and achieve high molecular weight.
Over 90% of global Hexamethylenediamine production is consumed in polymer applications, with nylon 6,6 accounting for the majority due to its widespread use in textiles, automotive parts, and engineering plastics.
The global nylon 6,6 market exceeded 2 million tons annually by 2025, reflecting sustained demand for Hexamethylenediamine's mechanical strength, thermal stability, and versatility in fiber and resin forms.
A smaller but significant portion of Hexamethylenediamine is converted to hexamethylene diisocyanate (HDI) via phosgenation, where the diamine reacts with phosgene to produce the diisocyanate, which serves as a key precursor for polyurethane production.
HDI-based polyurethanes are valued for their flexibility, abrasion resistance, and use in coatings, adhesives, and foams.
Hexamethylenediamine also functions as a curing agent in epoxy resin systems, reacting with epoxide groups to form cross-linked thermoset networks that enhance mechanical properties, chemical resistance, and adhesion in composites and coatings.
This application leverages Hexamethylenediamine's bifunctional reactivity to achieve high cross-linking density in the cured resin.
OTHER INDUSTRIES OF SIGNIFICANCE of HEXAMETHYLENEDIAMINE:
Hexamethylenediamine is also important to various other industries including:
*Oil & Gas:
Ingredients for corrosion inhibitors and drilling fluids.
*Construction:
In certain adhesives and sealants (bonding).
*Personal care:
Conditioning benefit in hair and skin care.
*HI&I (Household, Industrial and Institutional):
Surfactant in cleaning products.
*Petroleum-Based Lubricants and Greases:
For the development of high performance lubricants.
*Pharma:
Hexamethylenediamine is used as an intermediate in pharmaceutical assays.
*Agriculture:
Crop pest and weed control.
BENEFITS & INDUSTRIAL VALUE of HEXAMETHYLENEDIAMINE:
Essential industrial raw chemical for engineering polymers and high-performance materials.
Hexamethylenediamine enables production of strong polymers like nylon with excellent mechanical properties.
Hexamethylenediamine facilitates custom chemical syntheses due to its bifunctional amine reactivity.
ENVIRONMENTAL & REACTIVITY of HEXAMETHYLENEDIAMINE:
Moderately biodegradable and does not bioaccumulate significantly.
Incompatible with oxidizing agents, strong acids, and some organic materials.
SYNTHESIS of HEXAMETHYLENEDIAMINE:
Hexamethylenediamine was first reported by Theodor Curtius.
Hexamethylenediamine is produced by the hydrogenation of adiponitrile:
NC(CH2)4CN + 4 H2 → H2N(CH2)6NH2
The hydrogenation is conducted on molten adiponitrile diluted with ammonia, typical catalysts being based on cobalt and iron.
The yield is good, but commercially significant side products are generated by virtue of reactivity of partially hydrogenated intermediates.
These other products include 1,2-diaminocyclohexane, hexamethyleneimine, and the triamine bis(hexamethylenetriamine).
An alternative process uses Raney nickel as the catalyst and adiponitrile that is diluted with hexamethylenediamine itself (as the solvent).
This process operates without ammonia and at lower pressure and temperature.
PHYSICAL CHARACTERISTICS of HEXAMETHYLENEDIAMINE:
Hexamethylenediamine is a colorless.
Physical state:
Viscous liquid at room temperature (crystallizes near its melting point).
Odor:
Slight and characteristic, typical of amines.
Viscosity:
High viscosity, aiding specific industrial processes.
Solubility:
soluble in water, and a series of other polar solvents.
Thermal stability:
Outstanding thermal stability, suitable for high-temperature industrial process.
Reactivity:
Moderately reactive due to its two amino groups (-NH2), enabling its use in chemical syntheses such as polymers.
Volatility:
Low vapor pressure, minimizing evaporation at ambient temperatures.
Chemical compatibility:
many acids and reactive chemicals are compatible creating salts and polymers.
Hygroscopic:
slightly hygroscopic, can take small quantities of moisture from air.
PRODUCTION of HEXAMETHYLENEDIAMINE:
Industrial synthesis
The primary industrial synthesis of hexamethylenediamine (HMDA) involves the catalytic hydrogenation of adiponitrile (ADN), derived mainly from butadiene via hydrocyanation.
The reaction proceeds as follows:
NC(CH2)4CN+4H2→H2N(CH2)6NH2
This process is conducted in the liquid phase, typically in the presence of excess ammonia to promote selectivity and suppress side reactions.
The hydrogenation occurs at temperatures of 100–150 °C and pressures of 100–300 bar, using fixed-bed or slurry reactors to ensure efficient contact between the gaseous hydrogen, liquid ADN, and solid catalyst.
Common catalysts include Raney nickel, cobalt-based systems, or iron-based formulations, often promoted by ammonia to enhance activity and minimize cyclization byproducts.
These conditions achieve high conversions, typically exceeding 95%, with yields of Hexamethylenediamine around 98% under optimized operation.
Key byproducts include 1,2-diaminocyclohexane, formed via intramolecular cyclization, and hexamethyleneimine, resulting from partial reduction and rearrangement.
Purification is achieved through multi-stage distillation, separating Hexamethylenediamine (boiling point 205 °C) from unreacted ADN, ammonia, and heavier impurities to meet polymer-grade specifications (>99.9% purity).
Global production capacity for Hexamethylenediamine via this route stands at approximately 2 million tons per year as of 2025, predominantly in integrated facilities co-producing nylon precursors.
For example, in June 2025, BASF started up a new world-scale plant in Chalampé, France, increasing its annual Hexamethylenediamine production capacity to 260,000 metric tons.
The process is energy-intensive due to high-pressure requirements but benefits from high atom economy and established infrastructure.
ALTERNATIVE METHODS
Bio-based production routes for hexamethylenediamine (HMDA) have emerged as sustainable alternatives to traditional petroleum-derived methods, leveraging microbial fermentation of renewable feedstocks such as sugars derived from maize or potato starch.
These processes typically involve engineered microorganisms that convert glucose or fructose into key precursors, such as adipic acid or its intermediates (e.g., muconic acid or glucaric acid), which are then chemically reduced to Hexamethylenediamine via hydrogenation of the corresponding dinitrile.
For instance, Genomatica has developed a fermentation-based technology using genetically modified bacteria to produce bio-Hexamethylenediamine directly from plant sugars, enabling the creation of renewably sourced nylon 6,6 precursors.
In laboratory settings, Hexamethylenediamine can be prepared through the reduction of adiponitrile (adipic acid dinitrile), a straightforward hydrogenation using catalysts like Raney nickel or cobalt under moderate pressure and temperature conditions, yielding Hexamethylenediamine with high selectivity after intermediate formation of aminonitriles.
Alternatively, variants of the Curtius rearrangement offer a multi-step route from adipic acid: the diacid is first converted to
Hexamethylenediamine's diacyl azide, which undergoes thermal decomposition to a diisocyanate, followed by hydrolysis and decarboxylation to afford the diamine.
These methods are valued for their precision in small-scale synthesis, though they require careful handling of hazardous intermediates like azides.
Life-cycle assessments of bio-based Hexamethylenediamine routes indicate potential environmental advantages, particularly in greenhouse gas emissions relative to fossil-based processes when accounting for biomass carbon sequestration and renewable energy inputs.
However, these benefits may be offset by higher eutrophication impacts from agricultural feedstocks.
Economic analyses highlight that bio-routes currently face higher production costs compared to conventional methods, limiting widespread adoption despite yield efficiencies approaching 90% in optimized fermentations—comparable to industrial benchmarks.
Pilot-scale developments underscore progress toward commercialization, with Genomatica operating pre-commercial facilities in partnership with Aquafil for bio-Hexamethylenediamine integration into nylon production since 2022, and a 2024 collaboration with BASF to scale fermentation technology for polyamide 6,6 applications.
These initiatives aim to achieve cost parity through process intensification, though challenges persist in feedstock scalability and enzyme stability for large-volume output as of 2025.
PROPERTIES of HEXAMETHYLENEDIAMINE:
PHYSICAL PROPERTIES
Hexamethylenediamine is a colorless crystalline solid that melts at a low temperature, often appearing as a yellowish liquid in commercial forms due to handling or minor impurities.
Hexamethylenediamine has a melting point of 39–42 °C and a boiling point of 204.6 °C.
The relative density of the solid form of Hexamethylenediamine is 0.978 at 19.5 °C (approximately 0.978 g/cm³), and the density of the liquid form is 0.84 g/cm³ at 50 °C.
Hexamethylenediamine exhibits a strong amine odor, characteristic of its fishy or ammonia-like scent.
Hexamethylenediamine demonstrates high solubility in water, approximately 500 g/L at 20 °C, and is also soluble in organic solvents such as ethanol and ether.
CHEMICAL PROPERTIES of HEXAMETHYLENEDIAMINE:
Hexamethylenediamine possesses the molecular formula H₂N(CH₂)₆NH₂ and a molar mass of 116.20 g/mol.
Hexamethylenediamine features a linear aliphatic structure comprising a six-carbon chain with primary amine (-NH₂) groups attached to each terminal carbon, conferring it the properties typical of a symmetrical diamine.
As a dibasic amine, hexamethylenediamine demonstrates significant basicity, with pKₐ values for its conjugate acids reported as 11.02 and 10.24 at 25°C.
These values reflect the sequential protonation of the two amine groups, where the first protonation is stronger due to reduced electrostatic repulsion compared to the second.
Hexamethylenediamine readily reacts with acids to form diammonium salts, exemplified by its combination with dicarboxylic acids to yield ionic compounds stable under certain conditions.
Additionally, the polar N-H bonds in the amine groups facilitate hydrogen bonding, both as donors and acceptors, which enhances intermolecular interactions and contributes to its behavior in aqueous environments.
Spectroscopic characterization confirms these structural features.
In infrared (IR) spectroscopy, the symmetric and asymmetric N-H stretching modes of the primary amine groups appear as distinct bands in the 3300–3500 cm⁻¹ region.
Proton nuclear magnetic resonance (¹H NMR) reveals the methylene protons α to the amines at approximately 2.7 ppm (triplet), while the remaining chain methylene protons resonate between 1.2 and 1.5 ppm as multiplets, consistent with an unbranched alkane chain influenced by the terminal functional groups.
NATURE of HEXAMETHYLENEDIAMINE:
Hexamethylenediamine is a white Flake Crystal, ammonia odor, flammable.
Melting point 41~42 deg C.
Boiling Point 204~205 deg C.
The relative density was 0. 883.
Viscosity (50 ℃)1. 46kPa -s.
Refractive index 4498.
Flash point 81 °c.
Slightly soluble in water: O ℃,lOOmL water dissolved 2.Og, 30 ℃,lOOmL water dissolved 0.85g; Difficult to dissolve in ethanol, ether and benzene.
Moisture and carbon dioxide are readily absorbed in the air.
PREPARATION METHOD of HEXAMETHYLENEDIAMINE:
According to the different sources of starting materials used, Hexamethylenediamine production method at present, the method of hydrogenation of adiponitrile and the method of using adipic acid as raw material are used in industrial production.
Adiponitrile catalytic hydrogenation method this method is divided into low pressure and high pressure two.
(1) low pressure method with adiponitrile as raw material, framework nickel as catalyst, ethanol as solvent, sodium hydroxide as co-catalyst, according to a certain proportion of the mixing tank after mixing, the reaction is carried out at a temperature of 70~90 ℃ and a pressure of 2~3MPa to obtain three kinds of materials: gas phase, liquid phase and solid phase.
After filtration, the reaction solution is sent to a distillation tower and subjected to distillation and rectification, dealcoholization, dehydration, Coke removal, removal of light and heavy components, top extraction distillation to obtain fine 1,6 A hexanediamine product, the yield of up to 97%.
(2) high pressure method with skeleton cobalt as catalyst, liquid ammonia as diluent, hydrogen, adiponitrile and liquid ammonia with 38:1:25(mol) respectively, the pump was sent to the preheater, and the mixture was heated to 90 ° C., and then sent to the fixed bed reactor at 90-150 ° C.
And 19.6-29.
Under the pressure of 4MPa, the reaction is carried out, and the gas and liquid phase are condensed and separated to obtain crude 1,6-Hexamethylenediamine, which is then continuously distilled through 5 distillation columns to dehydrate, de-coke, the light and heavy components and impurities are removed and purified by rectification to obtain a finished product of 1, 6-hexanediamine with a yield of 90%-93%.
Method using adipic acid as raw material in this method, adipic acid vapor and excess ammonia are heated to 340 ℃ by silica gel and other dehydration catalysts to generate adiponitrile, and then methanol and liquid ammonia are added thereto, with diatomite nickel as catalyst, in 90~100 ℃, with 10. 1325~20. 265MPa hydrogen reduction to get the finished product
HISTORY of HEXAMETHYLENEDIAMINE:
DISCOVERY
Hexamethylenediamine, also known as 1,6-diaminohexane, was first synthesized and reported in 1900 by German chemists Theodor Curtius and Hans Clemm at Heidelberg University.
Their pioneering work involved the hydrogenation of adiponitrile (NC-(CH₂)₄-CN) to yield the target diamine, marking the initial laboratory preparation of this compound.
This method relied on reducing the dinitrile using hydrogen gas, a process that effectively converted the nitrile groups to primary amines while preserving the six-carbon chain length.
The synthesis was detailed in their publication in the Journal für Praktische Chemie, volume 62, pages 189–211, under the broader study of hydrazides and azides of organic acids.
Curtius and Clemm described the reaction conditions and isolated the product with a characteristic amine odor, confirming its structure through basic analytical techniques available at the time, such as boiling point determination and derivative formation.
This work built on Curtius's expertise in nitrogen-containing compounds, highlighting the diamine's reactivity as a bifunctional molecule suitable for further organic transformations.
Subsequent early laboratory methods in the 1900s–1910s expanded on nitrile reduction, often employing catalytic hydrogenation or chemical reductants like sodium in ethanol to achieve similar conversions from adiponitrile or related precursors.
Degradation routes, such as oxidative breakdown of longer-chain hexamethylene derivatives (e.g., from natural products or synthetic polymers), were explored but proved less efficient and were not central to the initial characterizations.
These approaches underscored hexamethylenediamine's role as a versatile building block in synthetic chemistry, though industrial-scale applications emerged later.
COMMERCIALIZATION
Hexamethylenediamine's development accelerated in the 1930s under DuPont's research led by Wallace Carothers, who synthesized it as a key monomer for nylon 6,6 in 1935, driven by efforts to create synthetic fibers amid growing demand for alternatives to silk.
By 1938, DuPont secured a foundational patent (US 2,130,948) for linear polyamides including those from hexamethylenediamine and adipic acid, enabling the polymer's commercialization.
Pilot plants at Belle, West Virginia, from 1937 to 1939 refined hexamethylenediamine production via adiponitrile hydrogenation, preparing for industrial scale-up.
The first commercial plant for hexamethylenediamine integrated into nylon production became operational in December 1939 at Seaford, Delaware, with an initial capacity of about 4 million pounds annually for the polymer, directly tied to synthetic fiber needs for consumer goods like hosiery.
World War II intensified adoption, as production shifted to military applications such as parachutes and tire cords by 1941, prompting rapid capacity expansions by DuPont to meet wartime demands.
Post-1950s, hexamethylenediamine production grew significantly with global nylon demand, as companies like DuPont licensed technologies and built additional facilities; by the 1970s, related nylon output exceeded 3 million metric tons annually worldwide.
Scaling of hydrogenation processes advanced through key patents, such as US 3,152,186 (1964) for continuous adiponitrile conversion, adopted by firms including BASF and later Invista (spun off from DuPont in 2004).
By the 2000s, global hexamethylenediamine capacity had reached over 1 million tons annually, reflecting its status as an industrial staple for polymers.
As of 2023, global hexamethylenediamine production capacity exceeds 1.5 million metric tons annually, driven by demand in automotive and textile sectors.
PHYSICAL and CHEMICAL PROPERTIES of HEXAMETHYLENEDIAMINE:
IUPAC Name: Hexane-1,6-diamine (sometimes written 1,6-hexanediamine)
Common Name: Hexamethylenediamine (HMDA)
CAS Registry Number: 124-09-4
EC Number (EINECS): 204-679-6
Molecular Formula: C6H16N2
Molecular Weight: 116.2–116.21 g/mol
Structure: Linear aliphatic diamine with six methylene (CH₂) groups terminating in two amine (–NH₂) groups.
Physical Description
Appearance: Colorless or white crystalline solid (commercial samples may be slightly yellow).
Odor: Strong amine (fish-like) odor.
Melting point: ~39–45 °C.
Boiling point: ~204–205 °C.
Density: ≈0.84–0.89 g/mL.
Solubility: Highly soluble in water; also soluble in alcohols and many polar organic solvents.
Vapor density: ~4 (vs air).
pH (in water): ~12.4 (strongly basic).
Hygroscopic (absorbs moisture).
Chemical Properties
Strong organic base (amine).
Forms stable salts with organic/inorganic acids (e.g., nylon salt with adipic acid).
Log P (partition coefficient): ~0.3–0.4 (reflecting moderate organic affinity).
CAS No.: 124-09-4
EC No.: 204-679-6
Formula: C6H16N2
Molecular Weight: ~116.2 g/mol
Appearance: Colorless to white solid
Odor: Strong amine odor
Melting Point: ~39–45 °C
Boiling Point: ~204–205 °C
Density: ~0.84–0.89 g/mL
Solubility: Very soluble in water; soluble in alcohol
pH(aqueous):~12.4
Flash Point:~80–94°C
Explosive Limits:~0.7–6.3%(v/v)
Vapor Density:~4(vsair)
Hygroscopic:Yes
Chemical formula:C6H16N2
Molar mass:116.208g·mol−1
Appearance:Colourless crystals
Density:0.84g/mL
Melting point:39to42°C
Boiling point:204.6°C
Solubility in water:490gL−1
log P:0.386
Thermochemistry
Std enthalpy of formation (ΔfH⦵298):−205kJmol−1
Linear Formula:NH2(CH2)6NH2
CAS Number:124-09-4
Molecular Weight:116.20
UNSPSC Code:12352100
NACRES:NA.22
PubChem Substance ID:24895434
EC Number:204-679-6
Beilstein/REAXYS Number:1098307
MDL number:MFCD00008243
Assay:98%
Bp:204-205°C
Physical state:crystalline
Color:colourless
Odor:No data available
Melting point/freezing point:42-45°C
Boiling point:199-205°C
Flammability:No data available
Upper explosion limit:6,3%(V)
Lower explosion limit:0,7%(V)
Flash point:80°C-closed cup
Autoignition temperature:315°C
Decomposition temperature:No data available
pH:12,4 at 100g/l at 25°C
Viscosity, kinematic:No data available
Viscosity, dynamic:No data available
Water solubility:0,637g/l at 20°C-OECD Test Guideline 105-soluble
Partition coefficient, n-octanol/water:log Pow:0,02
Vapor pressure:10hPa at 78,47°C
Density:0,89g/cm3 at 25°C
Relative density:0,978 at 19,5°C
Relative vapour density:4(vs air)
Particle characteristics:No data available
Explosive properties:No data available
Oxidizing properties:none
Surface tension:71,5mN/m at 1g/l at 20°C-OECD Test Guideline 115
Molecular Weight:116.20g/mol
XLogP3-AA:-0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:116.131348519Da
Monoisotopic Mass:116.131348519Da
Topological Polar Surface Area:52Ų
Heavy Atom Count:8
Formal Charge:0
Complexity:31.5
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Physical State:Solid
Storage:Desiccate at room temperature
Assay:98%
Form:crystalline solid
Refractive index n20/D:1.439(lit.)
SMILES:NCCCCCCN
InChI:1S/C6H16N2/c7-5-3-1-2-4-6-8/h1-8H2
InChI key:NAQMVNRVTILPCV-UHFFFAOYSA-N
CAS No:124-09-4
Product Code:FH16093
MDL No:MFCD00008243
Chemical Formula:C6H16N2
Molecular Weight:116.2g/mol
Smiles:C(CCCN)CCN
Melting Point:42°C
Boiling Point:205°C
Flash Point:80°C
Long Term Storage:store at 10°C-25°C, keep dry, keep under inert gas:Nitrogen
Empirical formula:C6H16N2
Molar mass (M):116,21g/mol
Density (D):0,83g/cm³
Melting point:42-45°C(lit.)
Boiling point:204-205°C
Density:0.89g/mL at 25°C(lit.)
Vapor density:4(vs air)
Vapor pressure:0.25hPa(20°C)
Refractive index:n20/D 1.439(lit.)
Flash Point:201°F
Storage temp.:Store below +30°C
Solubility:alcohol:soluble(lit.)
pKa:11.857(at 0°C)
Form:Solution
Color:White, may discolor during storage
pH:12.4 (100g/l,H2O,25°C)
Odor:pyridine odor
Explosive limit:0.9-7.6%(V)
Water Solubility:490g/L(20°C)
Sensitive:Hygroscopic
Merck:14,4695
BRN:1098307
Exposure limits:ACGIH:TWA 0.5 ppm
Stability:Stable.
Incompatible with strong oxidizing agents, strong acids, organic materials.
Cosmetics Ingredients Functions:BUFFERING
InChI:1S/C6H16N2/c7-5-3-1-2-4-6-8/h1-8H2
InChIKey:NAQMVNRVTILPCV-UHFFFAOYSA-N
SMILES:NCCCCCCN
LogP:0.4 at 25°C
CAS DataBase Reference:124-09-4
NIST Chemistry Reference:1,6-Hexanediamine(124-09-4)
EPA Substance Registry System:Hexamethylenediamine(124-09-4)
CAS Number:124-09-4
Molecular Formula:C6H16N2
Density:0.93g/cm³
Boiling Point:205°C
Melting Point:42°C
CAS:124-09-4
EINECS:204-679-6
InChI:InChI=1/C6H12.2H2N/c1-2-4-6-5-3-1;;/h1-6H2;2*1H3
Molecular Formula:C6H16N2
Molar Mass:116.2
Density:0.89g/mL at 25°C(lit.)
Melting Point:42-45°C(lit.)
Boiling Point:204-205°C
Flash Point:201°F
Water Solubility:490g/L(20°C)
Solubility:alcohol:soluble(lit.)
Vapor Pressure:0.25hPa(20°C)
Vapor Density:4(vs air)
Appearance:Solution
Color:White, may discolor during storage
Exposure Limit:ACGIH:TWA 0.5 ppm
Merck:14,4695
BRN:1098307
pKa:11.857(at 0°C)
pH:12.4 (100g/l,H2O,25°C)
Storage Condition:Store below +30°C
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, organic materials.
Sensitive:Hygroscopic
Explosive Limit:0.9-7.6%(V)
Refractive Index:n20/D 1.439(lit.)
Physical and Chemical Properties:White flaky crystals, with ammonia odor
FIRST AID MEASURES of HEXAMETHYLENEDIAMINE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available
ACCIDENTAL RELEASE MEASURES of HEXAMETHYLENEDIAMINE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
FIRE FIGHTING MEASURES of HEXAMETHYLENEDIAMINE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
EXPOSURE CONTROLS/PERSONAL PROTECTION of HEXAMETHYLENEDIAMINE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.
HANDLING and STORAGE of HEXAMETHYLENEDIAMINE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of HEXAMETHYLENEDIAMINE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
