13552-44-8 Usage
Chemical Properties
4,4’-Diaminodiphenylmethane is a pale yel-
low crystalline solid (turns light brown on contact with air)
with a faint amine-like odor.
Uses
In 1987, about 600 million lb of MDA was produced in the
United States captively as a chemical intermediate; additional
amounts were also imported. Approximately 99% of
theMDAand polymericMDAproduced in the United States,
usually by the acid-catalyzed reaction of aniline with formaldehyde,
is used as a chemical intermediate in the closedsystem
production of methylene diisocyanate (MDI) and
polymeric MDI, which are used extensively in the manufacture
of rigid semiflexible polyurethane foams for automobile
safety cushioning, and also in the production of wire coatings.
MDA is also used as a hardener or curing agent for
epoxy resins (providing cross-linkages), in the manufacture
of various natural and synthetic rubbers as an antioxidant, in
the production of polyurethane elastomers, as a curing agent
for neoprene, as an antioxidant in rubber, in the preparation of
polyamide–imide resins, as a metal deactivator fuel additive
(neutralizes the catalytic effect of copper associated with fuel
oxidation), and in the production of polymers for synthetic
fibers in the textile industry.
General Description
Light beige fine powder.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 13552-44-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,5,5 and 2 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 13552-44:
(7*1)+(6*3)+(5*5)+(4*5)+(3*2)+(2*4)+(1*4)=88
88 % 10 = 8
So 13552-44-8 is a valid CAS Registry Number.
13552-44-8Relevant articles and documents
Exclusion complexes of the HCl salts of benzidine and bis(4-aminophenyl) methane with two methyl-substituted cucurbiturils
Yan, Ying,Xue, Sai-Feng,Cong, Hang,Zhang, Jian-Xing,Zhang, Yun-Qian,Zhu, Qian-Jiang,Tao, Zhu
, p. 2136 - 2143 (2009)
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
A structural and spectroscopic investigation of the hydrochlorination of 4,4′-methylenedianiline
Gibson, Emma K.,Winfield, John M.,Muir, Kenneth W.,Carr, Robert H.,Eaglesham, Archie,Gavezzotti, Angelo,Lennon, David
scheme or table, p. 3824 - 3833 (2011/07/30)
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.
