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Methylene Bismorpholine is a low toxicity biocide specifically developed for the complete microbiological protection of metalworking fluids by incorporation into the concentrate.
Methylene Bismorpholine is a water based liquid, and it is described chemically as N,N1-methylene bis morpholine.
Methylene Bismorpholine is effective against bacteria and fungi, and it is recommended for formulating into the MWF concentrate.
CAS Number: 5625-90-1
Molecular Formula: C9H18N2O2
Molecular Weight: 186.25
EINECS Number: 227-062-3
Synonyms:Dimorpholinomethane, 5625-90-1, 4,4-Methylenedimorpholine, MORPHOLINE, 4,4'-METHYLENEDI-, 7O79DZW79Z, 4,4-methylene-bismorpholine, DTXSID8052859, DTXCID9031270, RefChem:506837, N,N'-Dimorpholinomethane, 4,4'-Methylenedimorpholine, 4-(morpholin-4-ylmethyl)morpholine, Morpholine, 4,4'-methylenebis-, N,N'-Methylenebismorpholine, MFCD00023369, bis(4-morpholinyl)methane, 4-[(morpholin-4-yl)methyl]morpholine, 4,4'-Methylenebismorpholine, Bismorpholino methane, n,n'-methylene-bis-morpholine, Bis(morpholino-)methan [German], Bis(morpholino-)methan, EINECS 227-062-3, BRN 0111886, UNII-7O79DZW79Z, 4-(morpholinomethyl)morpholine, AI3-62944, bismorpholinomethane, Contram ST-1, methylenebismorpholine, bis(morpholino)methane, N,N'-Dimorpholinomethane, Oprea1_332757, 4,4'-methanediyldimorpholine, 4-27-00-00203 (Beilstein Handbook Reference), SCHEMBL536772, SCHEMBL7709421, SCHEMBL11829900, FAA62590, AKOS002314380, 4,4'-METHYLENEBIS(MORPHOLINE), FS-4049, AC-12628, SY032818, DB-052882, CS-0236719, NS00008963, ST50410301, EN300-172423, G77474, Q865946, F2163-0188,mN,N’-Methylenebismorpholine, DIMORPHOLINOMETHANE, DIMORPHOLINOMETHONE, Morpholine,4,4-Methylenebis-, Methylene-bis-morpholine,N,N'-, MORPHOLINE44METHYLENEDI, 44METHYLENEBISMORPHOLINE, BIS-(MORPHOLINE-)METHANE
Methylene Bismorpholine, also known as Dimorpholinomethane or 4,4'-Methylenebismorpholine, is an organic heterocyclic compound that consists of two morpholine rings linked by a single methylene (-CH₂-) bridge, giving it the molecular formula C₉H₁₈N₂O₂.
The two morpholine rings are six-membered structures containing both a nitrogen atom and an oxygen atom, which confer the molecule with basicity, nucleophilicity, and the ability to form hydrogen bonds, while the central methylene group provides structural rigidity and spatial orientation that can influence its chemical reactivity and solubility.
Metal cutting fluid bactericide Methylene Bismorpholine is a slow-release bactericide with a broad spectrum and high efficiency and a certain gas-phase sterilization ability.
It is suitable for inhibiting the growth and reproduction of microorganisms in various humid environments, preventing the generation of putrefaction and foul odors, and ensuring safe operation of the system.
Methylene Bismorpholine is typically a colorless to pale yellow liquid or solid at room temperature, depending on purity and formulation, and it is soluble in many organic solvents, such as alcohols, ethers, and certain chlorinated solvents, but has limited solubility in water.
Its chemical structure and dual morpholine functionality make it a versatile intermediate in chemical synthesis, particularly in epoxy curing agents, polymer crosslinkers, and specialty resin production, where it can react with epoxides, isocyanates, or other electrophilic species to form stable, high-performance polymer networks.
Because of the nitrogen atoms in its morpholine rings, Methylene Bismorpholine exhibits moderate basicity, which allows it to act as a catalyst, stabilizer, or buffering agent in certain chemical reactions.
Methylene Bismorpholine is also used in industrial applications where controlled reactivity and bifunctional amine activity are needed, such as in coatings, adhesives, and elastomeric materials, as well as in metal surface treatment formulations, where it can contribute to corrosion inhibition and chemical stabilization.
Its dual-ring structure and reactive secondary amine groups also make it a compound of interest in polymer chemistry research, where it is utilized to improve mechanical properties, thermal stability, and chemical resistance of cured epoxy systems and other high-performance materials.
Because of its bifunctional amine character, Methylene Bismorpholine is also employed in metal treatment formulations and corrosion inhibitors, where it can interact with metal surfaces to form protective layers and enhance chemical stability, and in polymer research, where it is investigated as a building block for novel crosslinkers, dendrimers, and functionalized polymer networks.
Its chemical versatility, reactivity, and structural characteristics make it a key intermediate in the manufacture of specialty chemicals, high-performance polymers, and advanced material systems, and it is valued in both laboratory-scale synthesis and large-scale industrial applications.
Boiling point: 122-124 °C at 12 mmHg
Density: 1.04 g/cm3
Refractive index: 1.4790 (estimate)
Storage temp.: 2-8°C
pKa: 6.91 ± 0.10 (Predicted)
Appearance: Colorless to light yellow Liquid
Water Solubility: Soluble in water
InChI: InChI=1S/C9H18N2O2/c1-5-12-6-2-10(1)9-11-3-7-13-8-4-11/h1-9H2
InChIKey: MIFZZKZNMWTHJK-UHFFFAOYSA-N
SMILES: C(N1CCOCC1)N1CCOCC1
Methylene Bismorpholine, or Dimorpholinomethane, is a bifunctional heterocyclic compound characterized by two morpholine rings connected through a central methylene bridge, which allows it to act as a reactive amine with two nucleophilic sites, making it highly suitable for crosslinking reactions in polymer and resin chemistry.
The presence of oxygen and nitrogen heteroatoms in each morpholine ring imparts hydrogen-bonding ability, polarity, and moderate basicity, which not only influences its solubility in organic solvents but also facilitates interactions with a wide variety of electrophilic compounds, including epoxides, isocyanates, and anhydrides.
In industrial and research contexts, Methylene Bismorpholine is used as a curing agent for epoxy resins, polyurethane systems, and other thermosetting polymers, where it contributes to enhanced mechanical strength, thermal stability, chemical resistance, and dimensional stability of the resulting polymer networks.
Its dual-ring structure enables even distribution of reactive sites, allowing it to form dense, crosslinked polymer matrices that are highly resistant to degradation under heat, moisture, or chemical exposure.
Methylene Bismorpholine can serve as a catalyst, stabilizer, or additive in chemical formulations, assisting in controlled polymerization, improved adhesion, or surface modification of materials, as well as acting as a buffering agent in certain reactions where maintaining pH is critical.
Its moderate water solubility and good miscibility with many organic solvents make it suitable for industrial coatings, adhesives, sealants, and elastomeric materials, where precise chemical reactivity and compatibility with other formulation components are essential.
Methylene Bismorpholine containing biocidal products are used as bactericides for the preservation of fuels and metal working fluids which are prone to bacterial decay.
Two out of seven studies submitted were suitable for proof of preservation, whereas the remaining five studies, which also covered mycobacteria and fungi, were rather suitable for proof of disinfection properties.
Methylene Bismorpholine is a formaldehyde-releaser.
The biocidal activity of Methylene Bismorpholine is due to the interaction of the released formaldehyde with protein, DNA and RNA.
The interaction with protein results from a combination with the primary amide and the amino groups.
Methylene Bismorpholine reacts with carboxyl, sulfhydryl and hydroxyl groups.
As formaldehyde is not specific for one cellular target the development of resistances is not to be expected.
Methylene Bismorpholine is intended to be incorporated by industrial users into fuels during the formulation process, which is carried out automatically, to act as a preservative with bactericidal activity.
Uses Of Methylene Bismorpholine:
Methylene Bismorpholine is employed as intermediate for pharmaceutical.
Methylene Bismorpholineis widely utilized in industrial and chemical applications primarily as a curing agent for epoxy resins and polyurethane systems, where its dual morpholine rings provide two nucleophilic sites capable of reacting with epoxide or isocyanate groups, allowing it to form highly crosslinked, thermoset polymer networks that exhibit enhanced mechanical strength, thermal stability, chemical resistance, and dimensional stability.
This makes it particularly valuable in the production of coatings, adhesives, sealants, elastomers, and composite materials, where robust chemical and physical properties are essential for long-term performance in demanding environments.
In the polymer and materials research sectors, Methylene Bismorpholine is used as a bifunctional crosslinker or intermediate, enabling the design of advanced polymeric systems, dendrimers, and functionalized resins that benefit from its even distribution of reactive sites, which ensures uniform curing, dense network formation, and superior performance characteristics.
Its reactivity with electrophilic compounds such as epoxides, anhydrides, and isocyanates allows manufacturers to tailor polymer properties for specific applications, including high-performance coatings, corrosion-resistant layers, and chemically resistant industrial materials.
Methylene Bismorpholine also serves as a stabilizer, buffering agent, or catalyst in chemical formulations, where its moderate basicity and nucleophilic character can control reaction rates, maintain pH, and improve the stability of sensitive ingredients during polymerization or curing processes.
In addition, Methylene Bismorpholine is employed in metal treatment and surface protection formulations, where it interacts with metal substrates to form protective layers that reduce corrosion and improve adhesion of coatings, contributing to the longevity and reliability of industrial equipment and surfaces.
Furthermore, its solubility in organic solvents and compatibility with a wide range of materials makes it suitable for use in specialty coatings, adhesives, sealants, and elastomeric formulations, while in laboratory research it is often applied as a model bifunctional amine for the development of novel polymer networks, crosslinkers, and advanced materials, highlighting its versatility across both industrial-scale production and experimental studies.
Methylene Bismorpholine is extensively employed in industrial polymer chemistry as a bifunctional curing agent, where its two morpholine rings linked by a methylene bridge react efficiently with epoxide, isocyanate, or anhydride groups, enabling the formation of highly crosslinked, three-dimensional polymer networks that display outstanding mechanical strength, chemical resistance, thermal stability, and dimensional integrity, making it indispensable in applications such as high-performance coatings, protective films, adhesives, sealants, and composite materials designed for both industrial and consumer products.
In addition to its role in conventional thermoset systems, Methylene Bismorpholine is used in specialty polymer and resin development, where researchers exploit its bifunctional amine structure to design functionalized polymers, dendrimers, and advanced crosslinked networks with tailored properties, including enhanced toughness, improved elasticity, controlled degradation rates, and resistance to environmental stressors.
Its dual nucleophilic sites allow for precise control over polymer architecture, which is critical in applications such as electronic encapsulants, corrosion-resistant coatings, and high-performance industrial adhesives.
Methylene Bismorpholine is also utilized as a catalyst, stabilizer, and buffering agent in various chemical processes, where its moderate basicity and reactive amine groups facilitate controlled polymerization, prevent premature curing, and stabilize sensitive chemical intermediates, ensuring consistent quality and performance in industrial formulations.
In metal treatment and surface engineering, Methylene Bismorpholine functions to enhance adhesion of protective coatings, inhibit corrosion, and improve surface durability, making it a valuable additive in maintenance formulations for machinery, pipelines, and metal structures.
Safety Profile Of Methylene Bismorpholine:
Methylene Bismorpholine can cause moderate to severe skin irritation upon direct contact, manifesting as redness, itching, and possible dermatitis, especially with prolonged or repeated exposure, and it may lead to allergic skin reactions in sensitive individuals.
Accidental contact with the eyes can result in irritation, redness, watering, and discomfort, which underscores the importance of using protective gloves, long sleeves, and eye protection when handling the compound in industrial or laboratory settings.
Inhalation of dust, vapors, or aerosols of Methylene Bismorpholine may irritate the mucous membranes of the respiratory tract, causing coughing, throat discomfort, and mild breathing difficulty.
Although it is not highly volatile, adequate ventilation, fume hoods, and respirators are recommended when working with the powder or during processes that can generate airborne particles.
Repeated or prolonged exposure to Methylene Bismorpholine has the potential to cause skin sensitization and allergic reactions, meaning that even small subsequent exposures could lead to enhanced dermal irritation or dermatitis in susceptible individuals.
Proper personal protective equipment (PPE) and strict hygiene practices, including washing hands and exposed skin after contact, are essential to prevent sensitization.
