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Methyl isocyanate

Methyl isocyanate (MIC) is an organic


compound with the molecular formula
CH3NCO. Synonyms are
isocyanatomethane, methyl
carbylamine and MIC. Methyl
isocyanate is an intermediate chemical
in the production of carbamate
pesticides (such as carbaryl,
carbofuran, methomyl, and aldicarb). It
has also been used in the production
of rubbers and adhesives. As a highly
toxic and irritating material, it is
extremely hazardous to human health.
It was the principal toxicant involved in
the Bhopal disaster, which killed nearly
2,259 people initially and officially
3,787 people in total.[5][6][7][8][9][10][11]

Methyl isocyanate

Names

Preferred IUPAC name


Isocyanatomethane

Other names
Methyl isocyanate
methyl carbylamine
MIC

Identifiers

CAS Number 624-83-9

3D model (JSmol) Interactive


image

ChEBI CHEBI:59059

ChemSpider 11727

ECHA InfoCard 100.009.879

IUPHAR/BPS 6290
PubChem CID 12228

InChI
InChI=1S/C2H3NO/c1-3-2-4/h1H3
Key: HAMGRBXTJNITHG-UHFFFAOYSA-N

SMILES
O=C=N/C

Properties

Chemical formula H3CNCO

Molar mass 57.051 g/mol

Appearance Colorless liquid

Odor Sharp, pungent


odor[1]

Density 0.9230 g/cm3 at


27 C

Melting point 45 C (49 F;


228 K) [2]
Boiling point 38.3 C
(100.9 F;
311.4 K) [2]

Solubility in water 10% (15C)[1]

Vapor pressure 57.7 kPa

Structure

Dipole moment 2.8 D

Thermochemistry

Std enthalpy of 92.0 kJmol1[2]


formation (fHo298)

Hazards

EU classification (DSD) F+ T+
(outdated)

R-phrases (outdated) R12, R24/25,


R26, R37/38,
R41, R42/43,
R63

S-phrases (outdated) (S1/2), S26,


S27/28,
S36/37/39, S45,
S63

NFPA 704 3
4 3
W

Flash point 7 C (19 F;


266 K)

Autoignition 534 C (993 F;


temperature
807 K)

Explosive limits 5.326%[2]

Lethal dose or concentration (LD, LC):

LD50 (median dose) 120 mg/kg (oral,


mouse)
51.5 mg/kg
(oral, rat)[3]

LC50 (median 6.1 ppm (rat, 6


concentration) hr)
12.2 ppm
(mouse, 6 hr)
5.4 ppm (guinea
pig, 6 hr)
21 ppm (rat, 2
hr)[3]

US health exposure limits (NIOSH):

PEL (Permissible) TWA 0.02 ppm


(0.05 mg/m3)
[skin][1]

REL (Recommended) TWA 0.02 ppm


(0.05 mg/m3)
[skin][1]
IDLH (Immediate danger) 3 ppm[1]

Related compounds

Related compounds Methyl


isothiocyanate

Except where otherwise noted, data are given


for materials in their standard state (at 25 C
[77 F], 100 kPa).

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Infobox references

Physical properties
Methyl isocyanate (MIC) is a colorless,
poisonous, lachrymatory (tearing
agent), flammable liquid.[12] It is
soluble in water to 610 parts per 100
parts, but it also reacts with water (see
Reactions below).

Manufacture
Methyl isocyanate is usually
manufactured by the reaction of
monomethylamine and phosgene. For
large scale production, it is
advantageous to combine these
reactants at higher temperature in the
gas phase. A mixture of methyl
isocyanate and two moles of hydrogen
chloride is formed, but N-
methylcarbamoyl chloride (MCC) forms
as the mixture is condensed, leaving
one mole of hydrogen chloride as a
gas.

The methyl isocyanate is obtained by


treating the MCC with a tertiary amine,
such as N,N-dimethylaniline, or with
pyridine[13] or by separating it by using
distillation techniques.[14]
Methyl isocyanate is also
manufactured from N-
methylformamide and air. In the latter
process, it is immediately consumed in
a closed-loop process to make
methomyl.[15] Other manufacturing
methods have been reported.[16][17]

Reactions
Methyl isocyanate reacts readily with
many substances that contain N-H or
O-H groups. With water, it forms 1,3-
dimethylurea and carbon dioxide with
the evolution of heat (325 calories per
gram of MIC):

At 25 C, in excess water, half of the


MIC is consumed in 9 min.;[18] if the
heat is not efficiently removed from the
mixture, the rate of the reaction will
increase and rapidly cause the MIC to
boil. If MIC is in excess, 1,3,5-
trimethylbiuret is formed along with
carbon dioxide.[12] Alcohols and
phenols, which contain an O-H group,
react slowly with MIC, but the reaction
can be catalyzed by trialkylamines or
dialkyltin dicarboxylate. Oximes,
hydroxylamines, and enols also react
with MIC to form methylcarbamates.[12]
These reactions produce the products
described below (Uses).

Ammonia, primary, and secondary


amines rapidly react with MIC to form
substituted ureas. Other N-H
compounds, such as amides and
ureas, react much more slowly with
MIC.[19]

It also reacts with itself to form a trimer


or higher molecular weight polymers.
In the presence of catalysts, MIC
reacts with itself to form a solid trimer,
trimethyl isocyanurate, or a higher
molecular weight polymer:

Sodium methoxide, triethyl phosphine,


ferric chloride and certain other metal
compounds catalyze the formation of
the MIC-trimer, while the high-
molecular-weight polymer formation is
catalyzed by certain trialkylamines.
Since the formation of the MIC trimer is
exothermic (298 calories per gram of
MIC), the reaction can lead to violent
boiling of the MIC. The high-molecular-
weight polymer hydrolyzes in hot water
to form the trimethyl isocyanurate.
Since catalytic metal salts can be
formed from impurities in commercial
grade MIC and steel, this product must
not be stored in steel drums or
tanks.[12]
Hazards
Methyl isocyanate (MIC) is extremely
toxic. The threshold limit value set by
the American Conference on
Government Industrial Hygienists is
0.02 ppm. MIC is toxic by inhalation,
ingestion and contact in quantities as
low as 0.4 ppm. Exposure symptoms
includes coughing, chest pain,
dyspnea, asthma, irritation of the eyes,
nose and throat, as well as skin
damage. Higher levels of exposure,
over 21 ppm, can result in pulmonary
or lung edema, emphysema and
hemorrhages, bronchial pneumonia
and death. Although the odor of methyl
isocyanate cannot be detected at 5
ppm by most people, its potent
lachrymal properties provide an
excellent warning of its presence (at a
concentration of 24 parts per million
(ppm) subject's eyes are irritated, while
at 21 ppm, subjects could not tolerate
the presence of methyl isocyanate in
air).[20]

Proper care must be taken to store


methyl isocyanate because of its ease
of exothermically polymerizing (see
Reactions) and its similar sensitivity to
water. Only stainless steel or glass
containers may be safely used; the MIC
must be stored at temperatures below
40 C (104 F) and preferably at 4 C
(39 F).

The toxic effect of the compound was


apparent in the Bhopal disaster, when
around 42,000 kilograms (93,000 lb) of
methyl isocyanate and other gases
were released from the underground
reservoirs of the Union Carbide India
Limited (UCIL) factory, over a
populated area on December 3, 1984,
immediately killing thousands.

Extraterrestrial occurrence

Methyl isocyanate around young Sun-like stars


detected by ALMA.[21]

On 30 July 2015, scientists reported


that upon the first touchdown of the
Philae lander on comet 67/P's surface,
measurements by the COSAC and
Ptolemy instruments revealed sixteen
organic compounds, four of which
were seen for the first time on a comet,
including acetamide, acetone, methyl
isocyanate and
propionaldehyde.[22][23][24]

References
1. "NIOSH Pocket Guide to Chemical
Hazards #0423" . National Institute for
Occupational Safety and Health (NIOSH).
2. Lide, David R., ed. (2006). CRC
Handbook of Chemistry and Physics
(87th ed.). Boca Raton, FL: CRC Press.
ISBN 0-8493-0487-3.
ISBN 0-8493-0487-3.
3. "Methyl isocyanate" . Immediately
Dangerous to Life and Health. National
Institute for Occupational Safety and
Health (NIOSH).
4.
http://www.nmsu.edu/safety/programs/
chem_safety/NFPA-ratingJ-R.htm
5. Methyl Isocyanate. Union Carbide F-
41443A 7/76. Union Carbide
Corporation, New York 1976
6. Operating Manual Part II. Methyl
Isocyanate Unit. Union Carbide India
Limited, Agricultural Products Division,
1979
7. Broughton E (2005). "The Bhopal
disaster and its aftermath: a review" .
Environmental Health. 4 (1): 6.
doi:10.1186/1476-069X-4-6 .
PMC 1142333 . PMID 15882472 .
8. Eckerman I (2001). "Chemical Industry
and Public Health Bhopal as an
example" (pdf). MPH. Gteborg, Sweden:
Nordic School of Public Health. 2001
(24). ISSN 1104-5701 .
9. Eckerman I (2004). The Bhopal Saga -
Causes and Consequences of the World's
Largest Industrial Disaster . India:
Universities Press. ISBN 81-7371-515-7.
10. Rosenberg J. "At 1984 - Huge Poison
10. Rosenberg J. "At 1984 - Huge Poison
Gas Leak in Bhopal, India" . About.com.
Retrieved 2008-07-10.
11. Eckerman I (2013). "Bhopal Gas
Catastrophe 1984: Causes and
Consequences" . Reference Module in
Earth Systems and Environmental
Sciences. Elsevier. ISBN 978-0-12-
409548-9.
12. Union Carbide Corporation "Methyl
Isocyanate" Product Information
Publication, F-41443, November 1967.
13. US patent 2480088 , Slocombe, R. J.;
Hardy, E. E., "Process of Producing
Carbamyl Chlorides", issued 1949-08-23,
assigned to Monsanto
assigned to Monsanto
14. FR patent 1400863 , Merz, W.,
"Procd et dispositif de prparation
d'isocyanates d'alkyle", issued 1965-05-
28, assigned to Bayer
15. Chemical Week, "A fleeting existence
for toxic-gas molecules" p. 9, June 12,
1985.
16. DE patent 2828259 , Giesselmann, G.;
Guenther, K.; Fuenten, W., "Verfahren zur
Herstellung von Methyl Isocyanate",
issued 1980-01-10, assigned to Degussa
17. "A safer method for making
carbamates". Chemical Week. 1985b (20):
136. 1985.
18. Castro EA, Moodie RB, Sansom PJ
(1985). "The kinetics of hydrolysis of
methyl and phenyl isocyanates". Journal
of the Chemical Society, Perkin
Transactions 2. 1985 (5): 737742.
doi:10.1039/P29850000737 .
19. March J (1985). Advanced Organic
Chemistry (3rd ed.). New York: John
Wiley & Sons. p. 802.
20. Kimmerle G, Eben A (1964). "Zur
Toxizitt von Methylisocyanat und
dessen quantitativer Bestimmung in der
Luft". Archiv fr Toxikologie. 20 (4): 235
241. doi:10.1007/bf00577897 .
21. "ALMA Finds Ingredient of Life
21. "ALMA Finds Ingredient of Life
Around Infant Sun-like Stars" .
www.eso.org. Retrieved 8 June 2017.
22. Jordans F (30 July 2015). "Philae
probe finds evidence that comets can be
cosmic labs" . The Washington Post.
Associated Press. Retrieved 30 July
2015.
23. "Science on the Surface of a Comet" .
European Space Agency. 30 July 2015.
Retrieved 30 July 2015.
24. Bibring JP, Taylor MG, Alexander C,
Auster U, Biele J, Finzi AE, Goesmann F,
Klingehoefer G, Kofman W, Mottola S,
Seidenstiker KJ, Spohn T, Wright I (31
July 2015). "Philae's First Days on the
Comet - Introduction to Special Issue" .
Science. 349 (6247): 493.
Bibcode:2015Sci...349..493B .
doi:10.1126/science.aac5116 .
PMID 26228139 . Retrieved 30 July 2015.

External links
NIOSH Safety and Health Topic:
Isocyanates , from the website of the
National Institute for Occupational
Safety and Health (NIOSH).
U.S. National Library of Medicine:
Hazardous Substances Databank
Methyl isocyanate
Retrieved from
"https://en.wikipedia.org/w/index.php?
title=Methyl_isocyanate&oldid=803430072"

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