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Methyl isocyanate
Names
Other names
Methyl isocyanate
methyl carbylamine
MIC
Identifiers
ChEBI CHEBI:59059
ChemSpider 11727
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
Structure
Thermochemistry
Hazards
EU classification (DSD) F+ T+
(outdated)
NFPA 704 3
4 3
W
Related compounds
verify (what is ?)
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.
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):
Extraterrestrial occurrence
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
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