13552-44-8

Usage

Uses

Used in Chemical Industry:
4,4'-Methylenedianilinium dichloride is used as a chemical intermediate for the production of methylene diisocyanate (MDI) and polymeric MDI. These are extensively used in the manufacture of rigid and semiflexible polyurethane foams for automobile safety cushioning.
Used in Textile Industry:
MDA is used in the production of polymers for synthetic fibers, contributing to the development of various textile products.
Used in Rubber Industry:
4,4'-Methylenedianilinium dichloride serves as a hardener or curing agent for epoxy resins, providing cross-linkages. It is also utilized as an antioxidant in the manufacture of various natural and synthetic rubbers, as well as a curing agent for neoprene.
Used in Fuel Industry:
MDA acts as a metal deactivator fuel additive, neutralizing the catalytic effect of copper associated with fuel oxidation, which helps in improving the efficiency and performance of fuels.
Used in Plastics and Resins Industry:
4,4'-Methylenedianilinium dichloride is used in the preparation of polyamide-imide resins, which are essential in the production of high-performance plastics and resins with specific properties for various applications.

Air & Water Reactions

May be sensitive to prolonged exposure to air and light. Water soluble.

Reactivity Profile

In aqueous solution behaves as an acid. Materials in this group are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible. Many of these compounds catalyze organic reactions.

Fire Hazard

Flash point data for 4,4'-methylenedianilinium dichloride are not available; however, 4,4'-methylenedianilinium dichloride is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic and neoplastigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx and HCl.

Upstream product

• 101-77-9 4,4'-diamino diphenyl methane 

Downstream Products

• 86234-57-3 N,N-(Methylenedi-4,1-phenylene)bis(1,2-ethanediamine) 

Relevant academic research and scientific papers

Exclusion complexes of the HCl salts of benzidine and bis(4-aminophenyl) methane with two methyl-substituted cucurbiturils

The interaction between two partially methyl-substituted cucurbiturils, a sym-tetramethyl-substituted cucurbit[6]uril (TMeQ[6]) and a meta-hexamethyl- substituted cucurbituril (m-HMeQ[6]), with the hydrochloride salt of benzidine (g1·HCl) and the analogue

Reversible capture and release of aromatic amines by vicinal tricarbonyl compound

In this paper, we report reversible capture and release of aromatic amines by diphenylpropanetrione (DPPT). Addition of aromatic amines to the central carbonyl group occurred readily at ambient temperature to provide the aromatic amine adducts of DPPT (DPPT-aromatic amines), which has a hemiaminal structure. On the other hand, washing a solution of DPPT-aromatic amine with diluted hydrochloric acid (HCl) enabled successful recovery of DPPT to demonstrate the reversible nature of this system.

A structural and spectroscopic investigation of the hydrochlorination of 4,4′-methylenedianiline

The hydrochlorination of 4,4′-methylenedianiline, NH 2C6H4CH2C6H 4NH2 (MDA), in chlorobenzene to produce 4,4′-methylenedianiline dihydrochloride, [H3NC 6H4CH2C6H4NH 3]Cl2 (MDA·2HCl) is an important reaction for the production of isocyanates, which are used to manufacture polyurethanes. This reaction is examined here. MDA is moderately soluble in chlorobenzene, whereas MDA·2HCl is effectively insoluble. Controlled addition of anhydrous HCl to MDA in chlorobenzene led to the isolation of a solid whose stoichiometry is MDA·HCl. Crystals obtained from solutions of MDA·HCl in methanol were found by X-ray analysis to consist of the basic hydrochloride salt, [MDAH2][Cl]2[MDA]2H2O, which is stabilised by complex hydrogen-bonding. The starting material MDA has an H-bonded structure in which the molecules are linked in a one-dimensional chain. Hydrogen-bonding is extensive in MDA·2HCl which contains ladders of [H3NC6H4CH2C6H 4NH3]2+ dications stabilised by N-H...Cl linkages. Energy calculations on the crystalline systems allow an identification of the main factors in intermolecular cohesion; these are related to melting temperature and solubility data. Such improvements in understanding of solute-solute interactions are prerequisites for improving the atom economy of this important stage within the polyurethane manufacture process chain. The solid phase IR spectrum of MDA·2HCl is diagnostic, principally as a result of a Fermi resonance process.