M-Xylylenediamine

Last updated
m-Xylylenediamine
M-Xylylenediamine.svg
Names
Preferred IUPAC name
1,1′-(1,3-Phenylene)di(methanamine)
Other names
m-Xylene-α,α'-diamine
1,3-Benzenedimethanamine
MXDA
m-Phenylenebis(methylamine)
1,3-Bis(aminomethyl)benzene
1,3-Phenylenedimethanamine
1,3-Xylylenediamine
m-Xylylenediamine
1,3-Xylenediamine
m-Xylenediamine
1,3-Bis(aminomethyl)benzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.575 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 216-032-5
PubChem CID
RTECS number
  • PF8970000
UNII
UN number 2735
  • InChI=1S/C8H12N2/c9-5-7-2-1-3-8(4-7)6-10/h1-4H,5-6,9-10H2
  • C1=CC(=CC(=C1)CN)CN
Properties
C8H12N2
Molar mass 136.198 g·mol−1
AppearanceColorless liquid
Odor Amine [1]
Density 1.032 g/cm3 (20°C) [2]
Melting point 14 °C; 58 °F; 288 K [2]
Boiling point 247 °C; 477 °F; 520 K [2]
Miscible (20°C) [2]
Vapor pressure 0.03 mmHg (25°C) [2]
Hazards
Flash point 117 °C; 243 °F; 390 K [2]
Lethal dose or concentration (LD, LC):
700 ppm/1 hour (rat, inhalation) [3]
930 mg/kg (rat, oral) [3]
2 g/kg (rabbit, skin) [3]
NIOSH (US health exposure limits):
REL (Recommended)
C 0.1 mg/m3 [skin] [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

m-Xylylenediamine is an organic compound with the formula C6H4(CH2NH2)2. A colorless oily liquid, it is produced by hydrogenation of isophthalonitrile. [4]

Contents

Uses and reactions

m-Xylylenediamine (MXDA) is used in a variety of industrial applications including amine based curing agents for epoxy resins [5] which may then be formulated into coatings, adhesives, sealants, and elastomers. [1]

m-Xylylenediamine undergoes the Sommelet reaction to give isophthalaldehyde. [6]

Hazards

Exposure to m-xylylenediamine may occur by inhalation, skin contact, eye exposure, or ingestion. It can cause chemical burns, tissue damage, delayed pulmonary edema, shock, and skin sensitization. Symptoms of inhalation include a burning sensation in the respiratory tract, cough, sore throat, labored breathing, and dyspnea (shortness of breath). It is also flammable and produces toxic fumes when burned. m-Xylylenediamine reacts with acids, acid chlorides, and acid anhydrides. [1] [7]

Related Research Articles

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Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<span class="mw-page-title-main">Epoxy</span> Type of material

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

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<span class="mw-page-title-main">Nitrobenzene</span> Chemical compound

Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents.

<span class="mw-page-title-main">Ethylbenzene</span> Hydrocarbon compound; precursor to styrene and polystyrene

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

<i>p</i>-Xylene Chemical compound

p-Xylene (para-xylene) is an aromatic hydrocarbon. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The p- stands for para-, indicating that the two methyl groups in p-xylene occupy the diametrically opposite substituent positions 1 and 4. It is in the positions of the two methyl groups, their arene substitution pattern, that it differs from the other isomers, o-xylene and m-xylene. All have the same chemical formula C6H4(CH3)2. All xylene isomers are colorless and highly flammable. The odor threshold of p-xylene is 0.62 parts per million (ppm).

<span class="mw-page-title-main">Maleic anhydride</span> Chemical compound

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Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

<span class="mw-page-title-main">Diethylenetriamine</span> Chemical compound

Diethylenetriamine (abbreviated Dien or DETA) and also known as 2,2’-Iminodi(ethylamine)) is an organic compound with the formula HN(CH2CH2NH2)2. This colourless hygroscopic liquid is soluble in water and polar organic solvents, but not simple hydrocarbons. Diethylenetriamine is structural analogue of diethylene glycol. Its chemical properties resemble those for ethylene diamine, and it has similar uses. It is a weak base and its aqueous solution is alkaline. DETA is a byproduct of the production of ethylenediamine from ethylene dichloride.

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<span class="mw-page-title-main">Epichlorohydrin</span> Chemical compound

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Perchloryl fluoride is a reactive gas with the chemical formula ClO
3
F
. It has a characteristic sweet odor that resembles gasoline and kerosene. It is toxic and is a powerful oxidizing and fluorinating agent. It is the acid fluoride of perchloric acid.

<span class="mw-page-title-main">Glycidol</span> Chemical compound

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<span class="mw-page-title-main">Diepoxybutane</span> Chemical compound

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References

  1. 1 2 3 "M-Xylylenediamine". PubChem.
  2. 1 2 3 4 5 6 7 NIOSH Pocket Guide to Chemical Hazards. "#0671". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 3 "RTECS PF88DF10". NIOSH.
  4. Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363. ISBN   3527306730.
  5. "MXDA│Epoxy Resin Curing Agents│MITSUBISHI GAS CHEMICAL CO.,INC". www.aromaticchemicals.com. Retrieved 2018-08-19.
  6. Ackerman, J. H.; Surrey, A. R. (1967). "Isophthalaldehyde". Organic Syntheses. 47: 76. doi:10.15227/orgsyn.047.0076.
  7. "1,3-BIS(AMINOMETHYL)BENZENE". International Chemical Safety Cards.