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101-68-8

Basic Information
CAS No.: 101-68-8
Name: 4,4'-Diphenylmethane diisocyanate
Article Data: 57
Molecular Structure:
Molecular Structure of 101-68-8 (4,4'-Diphenylmethane diisocyanate)
Formula: C15H10N2O2
Molecular Weight: 250.257
Synonyms: 4,4'-Methylenediphenyl diisocyanate;4,4'-Methylenediphenylene isocyanate;Bis(p-isocyanatophenyl)methane;Di-(4-isocyanatophenyl)methane;Diphenylmethane-4,4'-diisocyanate;Diphenylmethane diisocyanate;Diphenylmethyl diisocyanate;Isocyanic acid, diphenylmethylene ester;Methylenebis(phenyl isocyanate);Methylenebis-p-phenylene diisocyanate;Methylene bisphenyl diisocyanate;Methylenedi-p-phenylene diisocyanate;4,4`-diphenylmethane diisocyanate;4,4'-Diphenylmethane diisocyanate;
EINECS: 202-966-0
Density: 1.19 g/cm3
Melting Point: 38-44 °C
Boiling Point: 373.4 °C at 760 mmHg
Flash Point: 154 °C
Solubility: decomposes in water
Appearance: white to light yellow flakes or crystals
Hazard Symbols: HarmfulXn,ToxicT,CorrosiveC
Risk Codes: 42/43-36/37/38-20
Safety: 45-36/37-23
Transport Information: UN 2811
PSA: 58.86000
LogP: 3.21200
Synthetic route

4,4'-methylenediphenyl dicarbamate

101-68-8

di(4-isocyanatophenyl)methane

Conditions
ConditionsYield
With copper In para-xylene at 220℃; under 2625.26 Torr; for 2h; Reagent/catalyst; Pressure; Temperature; Solvent;98.7%
7450-63-7

dimethyl 4,4'-methylenebis(1,4-phenylene)diurethane

101-68-8

di(4-isocyanatophenyl)methane

Conditions
ConditionsYield
With zinc diacetate; 1-((ethoxycarbonyl)methyl)-3-methylimidazolium tetrafluoroborate In neat (no solvent) at 25 - 230℃; for 0.25h; Catalytic behavior; Mechanism; Reagent/catalyst; Solvent; Inert atmosphere;96%
N-trimethyl-butyltetrafluoroboric acid; zinc(II) oxide at 200 - 240℃; under 48.7549 Torr; for 2.66667h;84%
With montmorillonite K-10 In decalin at 190℃; for 24h;40%
With boron trichloride; triethylamine In benzene for 0.5h; Heating;87 % Chromat.
32315-10-9

bis(trichloromethyl) carbonate

101-77-9

4,4'-diamino diphenyl methane

101-68-8

di(4-isocyanatophenyl)methane

Conditions
ConditionsYield
at 130℃; for 2h;92%
In ethyl acetate for 4h; Heating;90%
10097-16-2

(methylenedi-4,1-phenylene)bis-carbamic acid diethyl ester

101-68-8

di(4-isocyanatophenyl)methane

Conditions
ConditionsYield
With isocyanurate for 200h; Reflux;92%
With boron trichloride; triethylamine In benzene for 0.5h; Heating;93 % Chromat.
101-65-5

N,N'-(4,4'-methanediyl-di-phenyl)-bis-carbamic acid diphenyl ester

101-68-8

di(4-isocyanatophenyl)methane

Conditions
ConditionsYield
With DURANATE TPA-100 In 1,2-dichloro-benzene at 250℃; under 6000.6 Torr; for 200h; Inert atmosphere;86%
at 130 - 220℃; under 3.75038 - 450.045 Torr; for 240h; Product distribution / selectivity;82.3%
at 230℃; under 9.75098 Torr; Product distribution / selectivity; Industry scale;
75-44-5

phosgene

101-77-9

4,4'-diamino diphenyl methane

101-68-8

di(4-isocyanatophenyl)methane

Conditions
ConditionsYield
With hydrogenchloride; N-benzyl-N,N,N-triethylammonium chloride In water; 1,2-dichloro-benzene at 40 - 160℃; for 5h; pH=2 - 3;85.8%
With N,N-dimethyl-aniline; toluene
With 1,2-dichloro-benzene
In chlorobenzene at 90℃; under 7500.75 Torr; Inert atmosphere;

4,4'-methylenediphenylene biscarbamate

101-68-8

di(4-isocyanatophenyl)methane

Conditions
ConditionsYield
With benzoyl chloride In dodecane at 210℃; for 2.5h; Solvent;85%

4,4'-methylenediphenyldicarbamayl fluoride

101-68-8

di(4-isocyanatophenyl)methane

Conditions
ConditionsYield
at 160℃; for 0.5h; Glovebox;81%
47636-24-8

dibutyl diphenyl methane-4,4’-dicarbamate

101-68-8

di(4-isocyanatophenyl)methane

Conditions
ConditionsYield
tetrabutylphosphonium bis(trifluoromethanesulfonyl)imide at 180 - 240℃; under 48.7549 Torr; for 2.66667h;79%
216142-79-9

C25H36N4O2

101-68-8

di(4-isocyanatophenyl)methane

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 185℃; under 760.051 Torr; for 1.5h; Product distribution / selectivity;79%
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  • Hot Sale 4,4'-Diphenylmethane Diisocyanate (Mdi)

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    101-68-8

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  • 4,4′-Methylenebis(phenyl isocyanate) Diphenylmethane-4,4'-diisocyanate

  • Casno:

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  • Benzene,1,1'-methylenebis[4-isocyanato-

  • Casno:

    101-68-8

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  • 4,4'-Diphenylmethane diisocyanate

  • Casno:

    101-68-8

    4,4'-Diphenylmethane diisocyanate

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Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. Community Right-To-Know List.

Standards and Recommendations

OSHA PEL: CL 0.02 ppm
ACGIH TLV: 0.005 ppm
DFG MAK: 0.05 mg/m3; Confirmed Animal Carcinogen with Unknown Relevance to Humans
NIOSH REL: (Diisocyanates) TWA 0.005 ppm; CL 0.02 ppm/10M
DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD; DOT Class: 6.1; Label: Poison; DOT Class: 6.1; Label: Poison, Flammable Liquid; DOT Class: 3; Label: Flammable Liquid, Poison

Analytical Methods

For occupational chemical analysis use OSHA: #18, superseded by #47.

Specification

The 4,4'-Diphenylmethane diisocyanate, with the cas registry number 101-68-8, has the IUPAC name of 1-isocyanato-4-[(4-isocyanatophenyl)methyl]benzene. Following are the basic information of this chemical: This chemical is a kind of white to light yellow flakes or crystals with strong irritating odour, and is not soluble in water while soluble in acetone, benzene, kerosene and nitrobenzene. Its product categories are various, including diphenylmethanes (for high-performance polymer research); functional materials; reagent for high-performance polymer research; alphabetic; m; meta - meth. Besides, it is sensitive and is incompatible with strong oxidizing agents. When store it, keep it in the dry, cool and well-ventilated storeroom, away from the containing water products, alcohol and amine products.

The characteristics of 4,4'-Diphenylmethane diisocyanate are as follows:
 (1)ACD/LogP: 4.94; (2)ACD/LogD (pH 5.5): 4.93; (3)ACD/LogD (pH 7.4): 4.93; (4)ACD/BCF (pH 5.5): 3314.7; (5)ACD/BCF (pH 7.4): 3314.7; (6)ACD/KOC (pH 5.5): 11522.03; (7)ACD/KOC (pH 7.4): 11522.03; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 58.86 ; (11)Index of Refraction: 1.587; (12)Molar Refractivity: 74.38 cm3; (13)Molar Volume: 221 cm3; (14)Polarizability: 29.49 ×10-24 cm3; (15)Surface Tension: 45.6 dyne/cm; (16)Density: 1.13 g/cm3; (17)Flash Point: 154 °C; (18)Enthalpy of Vaporization: 62.06 kJ/mol; (19)Boiling Point: 373.4 °C at 760 mmHg; (20)Vapour Pressure: 9.02E-06 mmHg at 25°C; (21)Exact Mass: 250.074228; (22)MonoIsotopic Mass: 250.074228; (23)Topological Polar Surface Area: 58.9; (24)Heavy Atom Count: 19; (25)Complexity: 332.

Production method of 4,4'-Diphenylmethane diisocyanate is as below:
 4,4'-methanediyl-bis-aniline could react with carbonic acid bis-trichloromethyl ester to produce bis-(4-isocyanato-phenyl)-methane, with the following condition: reaction time: 2 hours; reaction temp.: 130 ℃; yield: 92%.

Use of 4,4'-Diphenylmethane diisocyanate:
 Methylene bisphenyl isocyanate could react with 2-trimethylsilanyloxy-ethylamine to produce 2-Trimethylsiloxyaethylisocyanat, with the following condition: reaction temp.: 200 ℃; yield: 84%.

As to its usage, it is widely used in many ways. It could be used in producing PU Elastomers, synthetic fibre, artificial leather, and solventless coatings; It could also be used as the adhesives in the rubber and plastic industry.

Safety information of 4,4'-Diphenylmethane diisocyanate:
While dealing with this chemical, you should be very cautious. It is irritating to eyes, respiratory system and skin, and may cause sensitisation by inhalation and skin contact; Besides being a kind of toxic chemical, it may at low levels cause damage to health; Then it may also destroy living tissue on contact for it is corrosive. Therefor, you should take the following instructions. Wear suitable protective clothing and gloves and do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer). If in case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).

Additionally, the following datas could be converted into the molecular structure:
(1)SMILES:O=C=N\c1ccc(cc1)Cc2ccc(\N=C=O)cc2
(2)InChI:InChI=1/C15H10N2O2/c18-10-16-14-5-1-12(2-6-14)9-13-3-7-15(8-4-13)17-11-19/h1-8H,9H2
(3)InChIKey:UPMLOUAZCHDJJD-UHFFFAOYAD

Below are the toxicity informatin of 4,4'-Diphenylmethane diisocyanate :

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TCLo inhalation 130ppb/30M (0.13ppm) IMMUNOLOGICAL INCLUDING ALLERGIC: INCREASED IMMUNE RESPONSE American Industrial Hygiene Association Journal. Vol. 27, Pg. 121, 1966.
 
mouse LD50 oral 2200mg/kg (2200mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 63, 1982.
rat LC50 inhalation 178mg/m3 (178mg/m3)   American Industrial Hygiene Association Journal. Vol. 43, Pg. 89, 1982.
 
rat LD50 oral 9200mg/kg (9200mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. OTS0516728