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).
Infobox references

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 to 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

Phenol Chemical compound

Phenol (also called carbolic acid) 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 (−C6H5) bonded to a hydroxy group (−OH). Mildly acidic, it requires careful handling because it can cause chemical burns.

Butanone Chemical compound

Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

Dichloromethane Chemical compound

Dichloromethane (DCM or methylene chloride) is an organochloride compound with the formula CH2Cl2. This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with water, it is polar, and miscible with many organic solvents.

Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, odorless, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products.

Phthalic anhydride Chemical compound

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.

Nitrobenzene Chemical compound

Nitrobenzene is an organic compound 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.

Formamide Chemical compound

Formamide, also known as methanamide, is an amide derived from formic acid. It is a clear liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs, other pharmaceuticals, herbicides, pesticides and the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers.

Acetone Simplest ketone

Acetone, or propanone, is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colourless, highly volatile and flammable liquid with a characteristic pungent odour.

<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).

Maleic anhydride Chemical compound

Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and polymers.

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 readily reacts with moisture in humid air to produce a corrosive, toxic and irritating mist, to which even short exposures can cause serious damage to health (see safety). Ethylenediamine is the first member of the so-called polyethylene amines.

Diethylenetriamine 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.

Diethanolamine Chemical compound

Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2. Pure diethanolamine is a white solid at room temperature, but its tendencies to absorb water and to supercool mean it is often encountered as a colorless, viscous liquid. Diethanolamine is polyfunctional, being a secondary amine and a diol. Like other organic amines, diethanolamine acts as a weak base. Reflecting the hydrophilic character of the secondary amine and hydroxyl groups, DEA is soluble in water. Amides prepared from DEA are often also hydrophilic. In 2013, the chemical was classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans" (Group 2B).

<i>sec</i>-Butyl acetate Chemical compound

sec-Butyl acetate, or s-butyl acetate, is an ester commonly used as a solvent in lacquers and enamels, where it is used in the production of acyclic polymers, vinyl resins, and nitrocellulose. It is a clear flammable liquid with a sweet smell.

Chromyl chloride Chemical compound

Chromyl chloride is the inorganic compound with the formula CrO2Cl2. It is a reddish brown compound that is a volatile liquid at room temperature, which is unusual for transition metal complexes.

Epichlorohydrin Chemical compound

Epichlorohydrin is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents. It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrin is a highly reactive electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.

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.

4,4′-Methylenedianiline (MDA) is an organic compound with the formula CH2(C6H4NH2)2. It is a colorless or white solid. It is produced on industrial scale as a precursor to polyurethanes.

n-Butyl glycidyl ether is an industrial chemical used in adhesives, sealants, and as a paint or coating additive.

4,4-Diaminodicyclohexylmethane is the name for organic compounds with the formula CH2(C6H10NH2)2. It is classified as a diamine. In the epoxy industry it is often referred to as PACM, short for para-diamino­dicyclohexyl­methane. It is used as a curing agent for epoxy resins It finds particular use in epoxy flooring. Another use is to produce diisocyanates, which are precursors to polyurethane. The mixture is a colorless solid, but typical samples are yellowish and oily. The compound is produced as a mixture of three isomers by the hydrogenation of methylenedianiline. These isomers are, in decreasing order of their yield from the hydrogenation, trans-trans, cis-trans, and a small amount of cis-cis.

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.
  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.