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4,4'-Methylenedianiline

Chemical Properties Uses Uses Preparation
4,4'-Methylenedianiline
4,4'-Methylenedianiline structure
CAS No.
101-77-9
Chemical Name:
4,4'-Methylenedianiline
Synonyms
MDA;DADPM;ht972;Tonox;HT 972;Tonox R;MDA-100;Tonox 22;Curithane;sumicurem
CBNumber:
CB7718182
Molecular Formula:
C13H14N2
Formula Weight:
198.26
MOL File:
101-77-9.mol

4,4'-Methylenedianiline Properties

Melting point:
89-91 °C(lit.)
Boiling point:
242 °C2 mm Hg(lit.)
Density 
1.15
refractive index 
1.5014 (estimate)
Flash point:
430 °F
solubility 
water: soluble
form 
neat
pka
5.32±0.25(Predicted)
Water Solubility 
Slightly soluble. <0.1 g/100 mL at 19 ºC
Merck 
14,2980
BRN 
474706
CAS DataBase Reference
101-77-9(CAS DataBase Reference)
Indirect Additives used in Food Contact Substances
4,4'-METHYLENEDIANILINE
FDA 21 CFR
177.1680; 177.2280; 177.2600
EWG's Food Scores
6
FDA UNII
GG5LL7OBZC
IARC
2B (Vol. 39, Sup 7) 1987
NIST Chemistry Reference
Benzenamine, 4,4'-methylenebis-(101-77-9)
Proposition 65 List
4,4'-Methylenedianiline
EPA Substance Registry System
4,4'-Methylenedianiline (101-77-9)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07,GHS08,GHS09
Signal word  Danger
Hazard statements  H317-H341-H350-H370-H373-H411-H302-H401
Precautionary statements  P201-P260-P280-P308+P311-P273-P308+P313-P301+P312a-P405-P501a
Hazard Codes  T,N
Risk Statements  45-39/23/24/25-43-48/20/21/22-51/53-68
Safety Statements  53-45-61
RIDADR  UN 2651 6.1/PG 3
WGK Germany  3
RTECS  BY5425000
TSCA  Yes
HazardClass  6.1
PackingGroup  III
HS Code  29215900
Toxicity LD50 oral in rabbit: 620mg/kg
NFPA 704
1
3 0

4,4'-Methylenedianiline price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 31640 4,4′-Diaminodiphenylmethane analytical standard 101-77-9 250mg $94.4 2021-12-16 Buy
Sigma-Aldrich 18139 4,4′-Diaminodiphenylmethane certified reference material, TraceCERT 101-77-9 50mg $150 2021-12-16 Buy
TCI Chemical M0220 4,4'-Diaminodiphenylmethane >98.0%(T) 101-77-9 25g $16 2021-12-16 Buy
TCI Chemical M0220 4,4'-Diaminodiphenylmethane >98.0%(T) 101-77-9 500g $39 2021-12-16 Buy
Alfa Aesar A15645 4,4'-Diaminodiphenylmethane 97% 101-77-9 50g $22.3 2021-12-16 Buy

4,4'-Methylenedianiline Chemical Properties,Uses,Production

Chemical Properties

4,4'-Methylenedianiline is a light brown crystalline solid with a faint amine odor. lt is very slightly soluble in water and soluble in alcohol, benzene,and ether. lt is combustible when exposed to heat or flame. When heated to decomposition,it emits toxic fumes of aniline and nitrogen oxides (NOx). The dihydrochloride is a crystalline solid that is soluble in water.
4,4'-Methylenedianiline
4,4'-Methylenedianiline is primarily used to produce 4,4-'methylenedianiline diisocyanate and other polymeric isocyanates which are used to manufacture polyurethane foams.

Uses

4,4'-Methylenedianiline is used in the production of polyurethane foams and epoxy resins. Potential contributor in pulmonary arterial hypertension (PAH) in rats through alteration of the serotenergic transport system. Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants. Dyes and metabolites, Environmental Testing.

Uses

Production of methylene diphenyl diisocyanate (MDI), which is used to produce polyurethanes; hardening agent for epoxy resins, anticorrosive materials, printed circuit parts, dyestuff intermediates, filament-wound pipe, and wire coatings

Preparation

93 g (1 mole) of aniline are dissolved in 96 % alcohol and to the cooled solution with proper stirring 120 g (1 mole) of 40 % formaldehyde solution are gradually added. After the addition is completed a second molecular portion of aniline, 93 g (1 mole) of aniline are added and the reaction is continued until the odor of formaldehyde has disappeared. The complete the reaction the mixture is refluxed for 2 hours. 130 g (1 mole) of aniline hydrochloride are then added, and boiling continued for a further 12 hours. The alcohol is distilled off, the residue made alkaline with the solution of sodium hydroxide and the excess of aniline removed by distillation with superheated steam. The residual oil, which consists of 4,4′-diaminodiphenylmethane, is then purified by solution in dilute hydrochloric acid and reprecipitation with dilute alkali. The 4,4′-diaminodiphenylmethane base is filtered off, washed and dried.
Preparation of 4,4′-methylenedianiline
Organic medical chemicals, by M. Barrowliff, 188-189, 1921

Description

Diaminodiphenylmethane is an aromatic diamine used as a curing agent in epoxy res ins of t11e bisphenol A type, as in the production of plastics, isocyanates, adhesives, elastomers, polyuret11ane (elastic and rigid foams, paints, lacquers, adhesives, binding agents, synt11etics rubbers, and elastomeric fibers) and butyl rubber. Diaminodiphenylmet11ane is also a by-product of azo dyes. It is also possibly formed by hydrolysis of diphenylmethane-4A'-diisocyanate.

Chemical Properties

4,4’-Diaminodiphenylmethane is a pale yellow crystalline solid (turns light brown on contact with air) with a faint amine-like odor.

Chemical Properties

white to yellow or beige flakes or crystals

Uses

4,4'-methylenedianiline be used as organic intermediates. Mainly used for the synthesis of polyimide and as curing agent of epoxy resin.

Uses

As chemical intermediate in production of isocyanates and polyisocyantes for preparation of polyurethane foams, Spandex fibers; as curing agent for epoxy resins and urethane elastomers; in production of polyamides; in the determination of tungsten and sulfates; in preparation of azo dyes; as corrosion inhibitor.

Uses

4,4'-Diaminodiphenyl-methane is used in the determination of tungsten and sulfates; in the preparation of azo dyes; cross-linking agent for epoxy resins; in the preparation of isocyanates and polyisocyanates; in the rubber industry as a curative for neoprene, as an anti-frosting agent (antioxidant) in footwear; raw material in preparation of poly(amide-imide) resins (used in magnet-wire enamels); curing agent for epoxy res ins and urethane elastomers; corrosion inhibitor; rubber additive (accelerator, antidegradant, retarder) in tires and heavy rubber products; in adhesives and glues, laminates, paints and inks, PVC products, handbags, eyeglass frames, plastic jewelry, electric encapsulators, surface coatings, spandex clothing, hairnets, eyelash curlers, earphones, balls, shoe soles, face masks.

Definition

ChEBI: An aromatic amine that is diphenylmethane substituted at the 4-position of each benzene ring by an amino group.

General Description

A tan flake or lump solid with a faint fishlike odor. May be toxic by inhalation or ingestion, and may be irritating to skin. Insoluble in water.

Air & Water Reactions

Oxidizes slowly in air in a reaction catalyzed by light. Somewhat hygroscopic. Insoluble in water.

Reactivity Profile

4,4'-Methylenedianiline polymerizes if heated above 257° F. Incompatible with strong oxidizing agents. 4,4'-Methylenedianiline is also incompatible with acids. Catalyzes isocyanate-alcohol and epoxide reactions. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Safety Profile

Confirmed carcinogen with experimental tumorigenic data. Human poison by ingestion. Poison by subcutaneous and intraperitoneal routes. Human systemic effects by ingestion: rigidity, jaundice, other liver changes. An eye irritant. Mutation data reported. It is not rapidly absorbed through the skin. Combustible when exposed to heat or flame. When heated to decomposition it emits highly toxic fumes of aniline and NOx.

Potential Exposure

Used as an intermediate and as a curing agent. Approximately 99% of the DDM produced is con- sumed in its crude form (occasionally containing not more than 50% DDM and ply-DDM) at its production site by reac- tion with phosgene in the preparation of isocyanates and poly- isocyanates. These isocyanates and polyisocyanates are employed in the manufacture of rigid polyurethane foams which find application as thermal insulation. Polyisocyanates are also used in the preparation of the semiflexible polyure- thane foams used for automotive safety cushioning. DDM is also used as: an epoxy hardening agent; a raw material in the production of polyurethane elastomers; in the rubber industry as a curative for Neoprene and as an antifrosting agent (anti- oxidant) in footwear; a raw material in the production of Quana nylon; and a raw material in the preparation of poly (amide-imide) resins (used in magnet wire enamels).

Carcinogenicity

4,4′-Methylenedianiline and its dihydrochloride salt are reasonably anticipated to be human carcinogens based on sufficient evidence of carcinogenicity from studies in experimental animals.

Environmental Fate

MDA is a pale brown crystalline powder with a faint aminelike odor. Exposure to air and light results in polymerization and oxidation of MDA. When heated, MDA produces toxic fumes of aniline and nitrogen oxides.
Most MDA enters the environment when it is produced or used to make other compounds. Forty-five percent of the produced compound is released to deep soil, 52.6% to the air, and 2.4% to land and water. Once in the environment, it will be mainly present as tiny particles in the air and it is removed from the atmosphere by dry deposition, rain, and snow scavenging. A small amount is transformed by reaction with hydroxyl radicals. In water, most of MDA will attach to particles and sediments, and will eventually settle to the bottom.
The estimated half-life of biodegradation in surface water, groundwater, and soil is 1–7 days, 2–14 days, and 1–7 days, respectively. With respect to aquatic ecosystems, bioconcentration factor values of 3.0–14 suggest that bioconcentration is low, in addition this compound does not tend to build up in the food chain. When released to soil, it is expected to have slight to no mobility. Similarly, volatilization from both moist and dry soil surfaces is not expected to be important.

Shipping

UN2651 4,40 -Diaminodiphenyl methane, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Crystallise the amine from water, 95% EtOH or *benzene. [Beilstein 13 IV 390.]

Toxicity evaluation

Currently, the mechanism of action is not completely understood and has been mostly assessed from information on structurally similar compounds. Many of the toxic properties of MDA have been attributed to metabolic intermediates, as these compounds are metabolically activated by N-oxidation to metabolites, such as N-hydroxymethylenedianiline, that react with DNA, RNA, and proteins.
Different studies suggest that both liver and thyroid are targets for MDA toxicity in humans and animals. Liver toxicity has been linked to impair mitochondrial function and structure, apoptosis, and increased oxidative stress. It may be caused by a reactive electrophile formed during metabolism since liver has the enzymatic routes necessary for such activation. Experimental studies indicate that biliary epithelial cells are damaged earlier than parenchymal cells and bile is a major route of exposure to MDA. The mechanism of thyroid toxicity has not yet been resolved. It has been observed that MDA exposure can induce a slight decrease in thyroid hormones in rats, thus triggering secretion of thyroid-stimulating hormone (TSH), which induced thyroid hyperplasia. Some of the induced adverse effects observed after MDA exposure (e.g., reduced food consumption, lower body weight gain, and effects on red cells, lymphocytes, and clotting parameters) could be explained as secondary responses.
MDA is carcinogenic to animals. The mechanism of liver or thyroid tumor development remains unclear. Even if cell injury may give indications of a nongenotoxic mechanism, it remains still unproved, and there are also positive genotoxic data in vitro and in vivo which indicate that a genotoxic mechanism may be related to the formation of a reactive metabolic intermediate cannot be excluded. Regarding thyroid cancer, hypersecretion of TSH may have a contribution to tumor formation.

Incompatibilities

Dust forms and explosive mixture with air. May polymerize in temperatures .125℃ . A weak base. Incompatible with strong oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong acids. Flammable gas- eous hydrogen may be generated in combination with strong reducing agents, such as hydrides .

Waste Disposal

Controlled incineration (oxides of nitrogen are removed from the effluent gas by scrubbers and/or thermal devices).

4,4'-Methylenedianiline Preparation Products And Raw materials

Raw materials

Preparation Products


4,4'-Methylenedianiline Suppliers

Global( 327)Suppliers
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Related articles


View Lastest Price from 4,4'-Methylenedianiline manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-10-19 MDA
101-77-9
US $48.00-40.00 / KG 1公斤 99% 20tons Guangzhou Sunton Biotechnology Co., Ltd.
2021-08-31 4,4'-diaminodiphenylmethane
101-77-9
US $50.00 / KG 1KG 99% 500tons/month Wuhan Shuokang Biological Technology Co.,Ltd
2021-08-31 4,4'-Methylenedianiline
101-77-9
US $10.00 / KG 100KG 99% 100 mt Hebei Guanlang Biotechnology Co., Ltd.

4,4'-Methylenedianiline Spectrum


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