過氧甲酸

過氧甲酸
Skeletal structure of performic acid	3D model of performic acid
	IUPAC名; Methaneperoxoic acid
別名	過甲酸; 過氧蟻酸
識別
CAS號	107-32-4
PubChem	66051
ChemSpider	59441
SMILES	O=COO;
性質
化學式	CH2O3
摩爾質量	62.02 g·mol−1
外觀	無色液體
熔點	-18 °C
沸點	50 °C
pKa	7.1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

過氧甲酸（英語：Performic acid）是一種有機過氧酸，分子式為CH
2O
3。它是不穩定的無色液體，可由甲酸和過氧化氫混合製得。過氧甲酸有強氧化性和殺菌能力，被用於醫療和食品工業領域。

性質

過氧甲酸在室溫下是無色液體，可溶於水、醇、乙醚、苯、氯仿等有機溶劑^[4]^[5]。因其具有強氧化性，被用於切割蛋白質中的二硫鍵^[6]，也被用於有機合成中的環氧化、羥化和氧化反應^[5]。在醫療和食品行業，過氧甲酸被用於消毒，其對病毒、細菌孢子、藻類、真菌、分枝桿菌及浮游生物等都有效。過氧甲酸氧化後的降解產物為水、二氧化碳和氧氣，因此會作為殺菌劑普及^[4]^[7]。過氧甲酸的消毒作用快於過氧乙酸和過氧化氫^[8]。

過氧甲酸的主要缺點是高反應性和不穩定性，因此其需要在合成後的約12小時內使用。此外，加熱過氧甲酸是十分危險的操作^[8]^[9]^[10] 。

合成

過氧甲酸可以通過甲酸與過氧化氫的平衡反應製備：

純的過氧甲酸尚未製得^[4]，但是簡單地混合等摩爾的反應物水溶液就可以得到濃度約48 %的過氧甲酸溶液。可以通過蒸餾將過氧甲酸的濃度提高至約90 %^[4]。

使用催化劑可以大規模地進行工業生產，但反應溫度需控制在80 - 85 °C以下以防爆炸^[11]。催化劑可使用硝酸、氫氟酸、磷酸、硫酸或其鹽^[4]^[12]；或是含有酯基的有機物，如羧酸酯^[13]、過氧乙酸^[8]。

安全性

過氧甲酸無毒，但對皮膚有刺激性（弱於過氧乙酸）。濃品（50 %以上）有強反應性，受熱易分解，快速加熱時會爆炸。室溫下與甲醛、苯甲醛、苯胺等易燃物混合時可能會燃燒或爆炸，遇金屬粉末會劇烈反應，乃至爆炸^[4]。

因此，處置泄漏的過氧甲酸需及時用冷水稀釋，並用中性、不可燃的無機吸附劑（如蛭石）吸收^[5]。

參考文獻

^ 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 （頁面存檔備份，存於網際網路檔案館）, 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. （原始內容 (PDF)存檔於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號, 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號, 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 （頁面存檔備份，存於網際網路檔案館）, 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. （原始內容 (PDF)存檔於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號, 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號, Issue date: April 11, 2000

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