イソシアン酸

関: isocyanate

WordNet

a salt or ester of isocyanic acid
street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/09/30 13:54:15」(JST)

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Isocyanic acid is a chemical compound with the formula HNCO, discovered in 1830 by Liebig and Wöhler.^[3] This colourless substance is volatile and poisonous, with a boiling point of 23.5 °C. Isocyanic acid is the simplest stable chemical compound that contains carbon, hydrogen, nitrogen, and oxygen, the four most commonly found elements in organic chemistry and biology.

Preparation and reactions

Isocyanic acid can be made by protonation of the cyanate anion, such as from salts like potassium cyanate, by either gaseous hydrogen chloride or acids such as oxalic acid.^[4]

H⁺ + NCO^- → HNCO

HNCO also can be made by the high-temperature thermal decomposition of cyanuric acid, a trimer.

C₃H₃N₃O₃ → 3 HNCO

Isocyanic acid hydrolyses to carbon dioxide and ammonia:

HNCO + H₂O → CO₂ + NH₃

At sufficiently high concentrations, isocyanic acid oligomerizes to give cyanuric acid and cyamelide, a polymer. These species usually are easily separated from liquid- or gas-phase reaction products. Dilute solutions of isocyanic acid are stable in inert solvents, e.g. ether and chlorinated hydrocarbons.^[5]

Isocyanic acid reacts with amines to give ureas (carbamides):

HNCO + RNH₂ → RNHC(O)NH₂.

This reaction is called carbamylation.

HNCO adds across electron-rich double bonds, such as vinylethers, to give the corresponding isocyanates.

Isocyanic acid is also present in various forms of smoke, including smog and cigarette smoke. It was detected using mass spectrometry, and easily dissolves in water, posing a health risk to the lungs.^[6]

Isomers: Cyanic acid and fulminic acid

Low-temperature photolysis of solids containing HNCO has been shown to make H-O-C≡N, known as cyanic acid or hydrogen cyanate; it is a tautomer of isocyanic acid.^[7] Pure cyanic acid has not been isolated, and isocyanic acid is the predominant form in all solvents.^[5] Sometimes information presented for cyanic acid in reference books is actually for isocyanic acid.^{[citation needed]}

Cyanic and isocyanic acids are isomers of fulminic acid (H-C=N-O), an unstable compound.^[8]

References

^ Cyanamide also has this name, and for which it is more systematically correct
^ Pradyot Patnaik. Handbook of Inorganic Chemicals. McGraw-Hill, 2002, ISBN 0-07-049439-8
^ Liebig, J.; Wöhler, F. (1830). "Untersuchungen über die Cyansäuren". Ann. Phys. 20 (11): 394. Bibcode:1830AnP....96..369L. doi:10.1002/andp.18300961102.
^ Fischer, G.; Geith, J.; Klapötke, T. M.; Krumm B. (2002). "Synthesis, Properties and Dimerization Study of Isocyanic Acid" (PDF). Z. Naturforsch. 57b (1): 19–25.
^ ^a ^b A. S. Narula, K. Ramachandran “Isocyanic Acid” in Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons, New York. doi:10.1002/047084289X.ri072m Article Online Posting Date: April 15, 2001.
^ Preidt, Robert. "Chemical in Smoke May Pose Health Risk". MyOptumHealth. AccuWeather. Retrieved 14 September 2011.
^ Jacox, M.E.; Milligan, D.E. (1964). "Low-Temperature Infrared Study of Intermediates in the Photolysis of HNCO and DNCO". Journal of Chemical Physics. 40 (9): 2457–2460. Bibcode:1964JChPh..40.2457J. doi:10.1063/1.1725546.
^ Kurzer, Frederick (2000). "Fulminic Acid in the History of Organic Chemistry". Journal of Chemical Education. 77 (7): 851–857. Bibcode:2000JChEd..77..851K. doi:10.1021/ed077p851.

External links

Walter, Wolfgang (1997). Organic Chemistry: A Comprehensive Degree Text and Source Book. Chichester: Albion Publishing. p. 364. ISBN 978-1-898563-37-2. Retrieved 2008-06-21.
Cyanic acid from NIST Chemistry WebBook (accessed 2006-09-09)

UpToDate Contents

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English Journal

Fragmentation of diamide derivatives of 3,4-ethylenedioxythiophene.

Stolić I, Bratoš I, Kovačević G, Bajić M.SourceDepartment of Chemistry and Biochemistry, Faculty of Veterinary Medicine, University of Zagreb, Heinzelova 55, 10000, Zagreb, Croatia.
Rapid communications in mass spectrometry : RCM.Rapid Commun Mass Spectrom.2012 May 15;26(9):1023-31. doi: 10.1002/rcm.6196.
The sequential product ion (MS(n)) fragmentation of four symmetric diamide derivatives of 3,4-ethylenedioxythiophene were characterized using ion trap mass spectrometry with electrospray ionization and their fragmentation patterns were studied. The experimental data consists of mass spectra obtained
PMID 22467451

Revisiting the reactivity of uracil during collision induced dissociation: tautomerism and charge-directed processes.

Beach DG, Gabryelski W.SourceDepartment of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada.
Journal of the American Society for Mass Spectrometry.J Am Soc Mass Spectrom.2012 May;23(5):858-68. Epub 2012 Feb 14.
In our recent work towards the nontarget identification of products of nucleic acid (NA) damage in urine, we have found previous work describing the dissociation of NA bases not adequate to fully explain their observed reactivity. Here we revisit the gas-phase chemistry of protonated uracil (U) duri
PMID 22351291

Japanese Journal

尿素分解過程の解明に向けたイソシアン酸の高精度計測法の開発

自動車技術会論文集 49(2), 235-240, 2018
NAID 130006565478

尿素SCR 触媒解析技術（第１報）

自動車技術会論文集 44(1), 51-56, 2013
NAID 130006318196

尿素を還元剤とする無触媒NO還元反応機講の数値計算による検討

化学工学論文集 27(5), 616-623, 2001-09-20
NAID 10007267868

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リンク元	「isocyanate」「イソシアン酸」

「isocyanate」

Isocyanic acid
Names
	IUPAC name Isocyanic acid
	Other names Carbimide
Identifiers
CAS Number	75-13-8 ; 420-05-3 (cyanic acid) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29202 ;
ChemSpider	6107 ;
ECHA InfoCard	100.109.068
PubChem CID	6347;
	InChI InChI=1S/CHNO/c2-1-3/h2H Key: OWIKHYCFFJSOEH-UHFFFAOYSA-N ; InChI=1/CHNO/c2-1-3/h2H Key: OWIKHYCFFJSOEH-UHFFFAOYAE;
	SMILES O=C=[N@H];
Properties
Chemical formula	HNCO
Molar mass	43.03 g/mol
Appearance	Colorless liquid or gas (b.p. near room temperature)
Density	1.14 g/cm3 (20 °C)
Melting point	−86 °C (−123 °F; 187 K)
Boiling point	23.5 °C (74.3 °F; 296.6 K)
Solubility in water	Dissolves
Solubility	Soluble in benzene, toluene, ether
Conjugate base	Isocyanate
Hazards
Main hazards	Poisonous
	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

　　[★]

n.

イソシアネート、イソシアン酸、ソシアン酸塩

関: isocyanic acid

「イソシアン酸」

　　[★]

英: isocyanic acid、isocyanate
関: イソシアン酸塩

[1] Cyanamide also has this name, and for which it is more systematically correct

[2] Pradyot Patnaik. Handbook of Inorganic Chemicals. McGraw-Hill, 2002, ISBN 0-07-049439-8

[3] Liebig, J.; Wöhler, F. (1830). "Untersuchungen über die Cyansäuren". Ann. Phys. 20 (11): 394. Bibcode:1830AnP....96..369L. doi:10.1002/andp.18300961102.

[4] Fischer, G.; Geith, J.; Klapötke, T. M.; Krumm B. (2002). "Synthesis, Properties and Dimerization Study of Isocyanic Acid" (PDF). Z. Naturforsch. 57b (1): 19–25.

[eEROS-5] A. S. Narula, K. Ramachandran “Isocyanic Acid” in Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons, New York. doi:10.1002/047084289X.ri072m Article Online Posting Date: April 15, 2001.

[6] Preidt, Robert. "Chemical in Smoke May Pose Health Risk". MyOptumHealth. AccuWeather. Retrieved 14 September 2011.

[7] Jacox, M.E.; Milligan, D.E. (1964). "Low-Temperature Infrared Study of Intermediates in the Photolysis of HNCO and DNCO". Journal of Chemical Physics. 40 (9): 2457–2460. Bibcode:1964JChPh..40.2457J. doi:10.1063/1.1725546.

[8] Kurzer, Frederick (2000). "Fulminic Acid in the History of Organic Chemistry". Journal of Chemical Education. 77 (7): 851–857. Bibcode:2000JChEd..77..851K. doi:10.1021/ed077p851.

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isocyanic acid