过氧甲酸

过氧甲酸
Skeletal structure of performic acid	3D model of performic acid
	IUPAC名; Methaneperoxoic acid
别名	过甲酸; 过氧蚁酸
识别
CAS号	107-32-4
PubChem	66051
ChemSpider	59441
SMILES	O=COO;
性质
化学式	CH2O3
摩尔质量	62.02 g·mol−1
外观	无色液体
熔点	-18 °C
沸点	50 °C
pKa	7.1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

过氧甲酸（英語：Performic acid）是一种有机过氧酸，分子式为CH
2O
3。它是不稳定的无色液体，可由甲酸和过氧化氢混合制得。过氧甲酸有强氧化性和杀菌能力，被用于医疗和食品工业领域。

性质

过氧甲酸在室温下是无色液体，可溶于水、醇、乙醚、苯、氯仿等有机溶剂^[4]^[5]。因其具有强氧化性，被用于切割蛋白质中的二硫键^[6]，也被用于有机合成中的环氧化、羟化和氧化反应^[5]。在医疗和食品行业，过氧甲酸被用于消毒，其对病毒、细菌孢子、藻类、真菌、分枝杆菌及浮游生物等都有效。过氧甲酸氧化后的降解产物为水、二氧化碳和氧气，因此会作为杀菌剂普及^[4]^[7]。过氧甲酸的消毒作用快于过氧乙酸和过氧化氢^[8]。

过氧甲酸的主要缺点是高反应性和不稳定性，因此其需要在合成后的约12小时内使用。此外，加热过氧甲酸是十分危险的操作^[8]^[9]^[10] 。

合成

过氧甲酸可以通过甲酸与过氧化氢的平衡反应制备：

纯的过氧甲酸尚未制得^[4]，但是简单地混合等摩尔的反应物水溶液就可以得到浓度约48 %的过氧甲酸溶液。可以通过蒸馏将过氧甲酸的浓度提高至约90 %^[4]。

使用催化剂可以大规模地进行工业生产，但反应温度需控制在80 - 85 °C以下以防爆炸^[11]。催化剂可使用硝酸、氢氟酸、磷酸、硫酸或其盐^[4]^[12]；或是含有酯基的有机物，如羧酸酯^[13]、过氧乙酸^[8]。

安全性

过氧甲酸无毒，但对皮肤有刺激性（弱于过氧乙酸）。浓品（50 %以上）有强反应性，受热易分解，快速加热时会爆炸。室温下与甲醛、苯甲醛、苯胺等易燃物混合时可能会燃烧或爆炸，遇金属粉末会剧烈反应，乃至爆炸^[4]。

因此，处置泄漏的过氧甲酸需及时用冷水稀释，并用中性、不可燃的无机吸附剂（如蛭石）吸收^[5]。

参考文献

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014: 749. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001.
^ ^2.0 ^2.1 ^2.2 Elvers, B. et al. (ed.) (1991) Ullmann's Encyclopedia of Industrial Chemistry, 5th ed. Vol. A19, Wiley, p. 206
^ F. A. Carroll Perspectives on Structure and Mechanism in Organic Chemistry, Wiley-Interscience, 2010, ISBN 0-470-27610-X p. 416
^ ^4.0 ^4.1 ^4.2 ^4.3 ^4.4 ^4.5 Swern, Daniel. Organic Peracids.. Chemical Reviews. 1949, 45: 1. doi:10.1021/cr60140a001. In the absence of catalysts, performic acid explodes when heated rapidly to 80–85°C.
^ ^5.0 ^5.1 ^5.2 Pradyot Patnaik A comprehensive guide to the hazardous properties of chemical substances （页面存档备份，存于互联网档案馆）, Wiley-Interscience, 2007, ISBN 0-471-71458-5, p. 128
^ Simpson, R. J. Performic Acid Oxidation of Proteins. Cold Spring Harbor Protocols. 2007, 2007: pdb.prot4698. doi:10.1101/pdb.prot4698.
^ Gehr, R; Chen, D; Moreau, M. Performic acid (PFA): tests on an advanced primary effluent show promising disinfection performance (PDF). Water Science and Technology. 2009, 59 (1): 89–96. PMID 19151490. doi:10.2166/wst.2009.761. （原始内容 (PDF)存档于2010-11-16）.
^ ^8.0 ^8.1 ^8.2 Preuss, A., Fuchs, R., Huss, M. & Schneider, R. 2001 Aqueous Disinfecting Agent Containing Performic Acid and Peracetic Acid Process for Production and Process for Use Thereof 美國專利第6,211,237号, Issue date: April 3, 2001
^ Bydzovska, O. & Merka, V. Disinfecting Properties of Performic Acid Against Bacteriophage (X 174 as a Model of Small Envelope-free Viruses. J. Hygiene, Epidemiology Microbiology and Immunology. 1981, 25 (4): 414–423. PMID 6459365.
^ Ripin, D.H.B.; et al. Execution of a Performic Acid Oxidation on Multikilogram Scale. Org. Process Res. Dev. 2007, 11: 762. doi:10.1021/op700039r.
^ Elvers, B. et al. (ed.) (1991) Ullmann's Encyclopedia of Industrial Chemistry, 5th ed. Vol. A12, Wiley, p. 16
^ English, James; Gregory, J. Delafield. Performic Acid Hydroxylation of a,p-Unsaturated Acids and Esters. Journal of the American Chemical Society. 1947, 69: 2120. doi:10.1021/ja01201a016.
^ Matilla, T. and Aksela, R. 2000 Method for the Preparation of Aqueous Solutions Containing Performic Acid as Well as Their Use. 美國專利第6,049,002号, Issue date: April 11, 2000

[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014: 749. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001.

[u1-2] 2.0 ^2.1 ^2.2 Elvers, B. et al. (ed.) (1991) Ullmann's Encyclopedia of Industrial Chemistry, 5th ed. Vol. A19, Wiley, p. 206

[3] F. A. Carroll Perspectives on Structure and Mechanism in Organic Chemistry, Wiley-Interscience, 2010, ISBN 0-470-27610-X p. 416

[j2-4] 4.0 ^4.1 ^4.2 ^4.3 ^4.4 ^4.5 Swern, Daniel. Organic Peracids.. Chemical Reviews. 1949, 45: 1. doi:10.1021/cr60140a001. In the absence of catalysts, performic acid explodes when heated rapidly to 80–85°C.

[b1-5] 5.0 ^5.1 ^5.2 Pradyot Patnaik A comprehensive guide to the hazardous properties of chemical substances （页面存档备份，存于互联网档案馆）, Wiley-Interscience, 2007, ISBN 0-471-71458-5, p. 128

[6] Simpson, R. J. Performic Acid Oxidation of Proteins. Cold Spring Harbor Protocols. 2007, 2007: pdb.prot4698. doi:10.1101/pdb.prot4698.

[7] Gehr, R; Chen, D; Moreau, M. Performic acid (PFA): tests on an advanced primary effluent show promising disinfection performance (PDF). Water Science and Technology. 2009, 59 (1): 89–96. PMID 19151490. doi:10.2166/wst.2009.761. （原始内容 (PDF)存档于2010-11-16）.

[pat2-8] 8.0 ^8.1 ^8.2 Preuss, A., Fuchs, R., Huss, M. & Schneider, R. 2001 Aqueous Disinfecting Agent Containing Performic Acid and Peracetic Acid Process for Production and Process for Use Thereof 美國專利第6,211,237号, Issue date: April 3, 2001

[9] Bydzovska, O. & Merka, V. Disinfecting Properties of Performic Acid Against Bacteriophage (X 174 as a Model of Small Envelope-free Viruses. J. Hygiene, Epidemiology Microbiology and Immunology. 1981, 25 (4): 414–423. PMID 6459365.

[10] Ripin, D.H.B.; et al. Execution of a Performic Acid Oxidation on Multikilogram Scale. Org. Process Res. Dev. 2007, 11: 762. doi:10.1021/op700039r.

[11] Elvers, B. et al. (ed.) (1991) Ullmann's Encyclopedia of Industrial Chemistry, 5th ed. Vol. A12, Wiley, p. 16

[12] English, James; Gregory, J. Delafield. Performic Acid Hydroxylation of a,p-Unsaturated Acids and Esters. Journal of the American Chemical Society. 1947, 69: 2120. doi:10.1021/ja01201a016.

[13] Matilla, T. and Aksela, R. 2000 Method for the Preparation of Aqueous Solutions Containing Performic Acid as Well as Their Use. 美國專利第6,049,002号, Issue date: April 11, 2000

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