乙酸銨

乙酸銨
	IUPAC名; Ammonium ethanoate
英文名	Ammonium acetate
識別
CAS號	631-61-8
PubChem	517165
ChemSpider	11925
SMILES	O=C([O-])C.[NH4+];
InChI	1/C2H4O2.H3N/c1-2(3)4;/h1H3,(H,3,4);1H3;
InChIKey	USFZMSVCRYTOJT-UHFFFAOYAY
ChEBI	62947
RTECS	AF3675000
性質
化學式	C2H7NO2
摩爾質量	77.08 g·mol−1
外觀	白色易潮解晶體
氣味	輕微乙酸味
密度	1.17 g/cm3（20 °C）; 1.073 g/cm3（25 °C）
熔點	113 °C（386 K）（）
溶解性（水）	102 g/100 mL（0 °C）; 148 g/100 mL（4 °C）; 143 g/100 mL（20 °C）; 533 g/100 mL（80 °C）
溶解性	可溶於乙醇、SO2、丙酮和液氨
溶解性（甲醇）	7.89 g/100 mL（15 °C）; 131.24 g/100 g（94.2 °C）
溶解性（二甲基甲醯胺）	0.1 g/100 g
pKa	9.9
pKb	33
磁化率	-41.1·10−6 cm3/mol
黏度	21
結構
晶體結構	正交晶系
熱力學
ΔfHm⦵298K	−615 kJ/mol
危險性
	GHS危險性符號;
GHS提示詞	Warning
H-術語	H303, H316, H320, H333
P-術語	P281, P335
主要危害	刺激性
NFPA 704	1 1 1
閃點	136 ℃
	致死量或濃度：
LD50（中位劑量）	386 mg/kg（小鼠，靜脈注射）
相關物質
其他陰離子	硝酸銨，硫酸銨
其他陽離子	乙酸鈉，乙酸鉀
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

乙酸銨是乙酸的銨鹽，分子式為CH₃COONH₄。它是白色、易潮解的晶體，可以由乙酸和氨反應而成。它可以在商業上買到。^[5]

製備[編輯]

乙酸銨可以由碳酸銨和乙酸中和而成或是由冰醋酸和氨氣反應而成：^[6]

\mathrm {2\ CH_{3}COOH+(NH_{4})_{2}CO_{3}\longrightarrow 2\ NH_{4}(CH_{3}COO)+\ H_{2}O+\ CO_{2}\uparrow }

\mathrm {CH_{3}COOH+NH_{3}\longrightarrow NH_{4}(CH_{3}COO)}

反應[編輯]

乙酸銨加熱脫水，生成乙醯胺：^[7]

\mathrm {CH_{3}COONH_{4}\ {\xrightarrow[{}]{\Delta }}\ CH_{3}{-}CO{-}NH_{2}+H_{2}O}

在有機合成中，乙酸銨可用來引入氮原子。^[7]它和醇在銥催化劑存在下反應，生成叔胺。^[8]^[7]

\mathrm {CH_{3}COONH_{4}+3RCH_{2}OH\ {\xrightarrow[{}]{(CpIr^{*}Cl_{2})_{2}}}\ N(CH_{2}R)_{3}+CH_{3}COOH+3H_{2}O}

乙酸銨、1,3-二羰基化合物和苯偶姻衍生物的一鍋法會生成四取代吡咯，反應不需要溶劑和催化劑。^[9]^[7]

在漢奇吡啶合成反應的變種中，1,4-二氫吡啶的衍生物可以通過β-羰基羧酸酯、醛和乙酸銨的反應產生。^[10]^[7]

用處[編輯]

乙酸銨可用作緩衝物質。^[11]由於它在低壓下會揮發，因此在製備質譜樣品時被用於替代不揮發的緩衝物質。^[12]乙酸銨也被用作食品添加劑，食品添加劑國際編碼為264。它已被澳大利亞和紐西蘭批准使用。^[13]

此外，乙酸銨還用於紡織和橡膠工業、農業和食品技術以及各種有機合成中。^[14]

參考資料[編輯]

^ ^1.0 ^1.1 ^1.2 Pradyot, Patnaik. Handbook of Inorganic Chemicals. The McGraw-Hill Companies, Inc. 2003. ISBN 0-07-049439-8.
^ ^2.0 ^2.1 ^2.2 Safety Data Sheet of Ammonium Acetate (PDF). tedia.com. Tedia Company Inc. 2011-08-12 [2014-06-10]. （原始內容存檔 (PDF)於2022-12-07）.
^ ^3.0 ^3.1 ^3.2 ^3.3 ^3.4 Ammonium acetate. [2022-08-26]. （原始內容存檔於2014-07-14）.
^ Davidson, Arthur W.; McAllister, Walter H. Solutions of Salts in Pure Acetic Acid. Ii. Solubilities of Acetates1. Journal of the American Chemical Society. 1930, 52 (2): 507–519. ISSN 0002-7863. doi:10.1021/ja01365a010.
^ Hosea Cheung; Robin S. Tanke; G. Paul Torrence, Acetic Acid, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a01_045.pub2
^ Brannt, William. A practical treatise on the manufacture of vinegar. Lancaster, PA: Henry Carey Baird & Co. 1914: 316–317.
^ ^7.0 ^7.1 ^7.2 ^7.3 ^7.4 Ammonium acetate. In: e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley and Sons, 1999–2013, abgerufen am 17. Februar 2018.
^ Yamaguchi, Ryohei; Kawagoe, Shoko; Asai, Chiho; Fujita, Ken-ichi. Selective Synthesis of Secondary and Tertiary Amines by Cp*Iridium-Catalyzed Multialkylation of Ammonium Salts with Alcohols. Organic Letters (American Chemical Society (ACS)). 2007-12-13, 10 (2): 181–184. ISSN 1523-7060. doi:10.1021/ol702522k.
^ Bhat, Subrahmanya Ishwar; Trivedi, Darshak R. A catalyst- and solvent-free three-component reaction for the regioselective one-pot access to polyfunctionalized pyrroles. Tetrahedron Letters (Elsevier BV). 2013, 54 (41): 5577–5582. ISSN 0040-4039. doi:10.1016/j.tetlet.2013.07.153.
^ Heydari, Akbar; Azizi, Kobra; Azarnia, Jamshid; Karimi, Meghdad; Yazdani, Elahe. Novel Magnetically Separable Sulfated Boric Acid Functionalized Nanoparticles for Hantzsch Ester Synthesis. Synlett (Georg Thieme Verlag KG). 2016-04-26, 27 (12): 1810–1813. ISSN 0936-5214. doi:10.1055/s-0035-1561441.
^ Williams, Robert J.; Lyman, Carl M. The Use of Ammonium Acetate as a Buffer. Journal of the American Chemical Society (American Chemical Society (ACS)). 1932, 54 (11): 4458–4458. ISSN 0002-7863. doi:10.1021/ja01350a503.
^ Berman, Elena S. F.; Fortson, Susan L.; Checchi, Kyle D.; Wu, Ligang; Felton, James S.; Kuang Jen, J. Wu; Kulp, Kristen S. Preparation of single cells for imaging/profiling mass spectrometry. J Am Soc Mass Spectrom. 2008, 19 (8): 1230–1236. PMID 18565760. doi:10.1016/j.jasms.2008.05.006 .
^ Australia New Zealand Food Standards Code Standard 1.2.4 - Labelling of ingredients. [2011-10-27]. （原始內容存檔於2013-09-02）.
^ Barthakur, Madan. Ammonium Acetate. Synlett (Georg Thieme Verlag KG). 2007, 2007 (9): 1475–1476. ISSN 0936-5214. doi:10.1055/s-2007-980375.

[pphoic-1] 1.0 ^1.1 ^1.2 Pradyot, Patnaik. Handbook of Inorganic Chemicals. The McGraw-Hill Companies, Inc. 2003. ISBN 0-07-049439-8.

[tedia-2] 2.0 ^2.1 ^2.2 Safety Data Sheet of Ammonium Acetate (PDF). tedia.com. Tedia Company Inc. 2011-08-12 [2014-06-10]. （原始內容存檔 (PDF)於2022-12-07）.

[chemister-3] 3.0 ^3.1 ^3.2 ^3.3 ^3.4 Ammonium acetate. [2022-08-26]. （原始內容存檔於2014-07-14）.

[4] Davidson, Arthur W.; McAllister, Walter H. Solutions of Salts in Pure Acetic Acid. Ii. Solubilities of Acetates1. Journal of the American Chemical Society. 1930, 52 (2): 507–519. ISSN 0002-7863. doi:10.1021/ja01365a010.

[Ullmann-5] Hosea Cheung; Robin S. Tanke; G. Paul Torrence, Acetic Acid, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a01_045.pub2

[6] Brannt, William. A practical treatise on the manufacture of vinegar. Lancaster, PA: Henry Carey Baird & Co. 1914: 316–317.

[eEROS-7] 7.0 ^7.1 ^7.2 ^7.3 ^7.4 Ammonium acetate. In: e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley and Sons, 1999–2013, abgerufen am 17. Februar 2018.

[8] Yamaguchi, Ryohei; Kawagoe, Shoko; Asai, Chiho; Fujita, Ken-ichi. Selective Synthesis of Secondary and Tertiary Amines by Cp*Iridium-Catalyzed Multialkylation of Ammonium Salts with Alcohols. Organic Letters (American Chemical Society (ACS)). 2007-12-13, 10 (2): 181–184. ISSN 1523-7060. doi:10.1021/ol702522k.

[Bhat-9] Bhat, Subrahmanya Ishwar; Trivedi, Darshak R. A catalyst- and solvent-free three-component reaction for the regioselective one-pot access to polyfunctionalized pyrroles. Tetrahedron Letters (Elsevier BV). 2013, 54 (41): 5577–5582. ISSN 0040-4039. doi:10.1016/j.tetlet.2013.07.153.

[Azizi-10] Heydari, Akbar; Azizi, Kobra; Azarnia, Jamshid; Karimi, Meghdad; Yazdani, Elahe. Novel Magnetically Separable Sulfated Boric Acid Functionalized Nanoparticles for Hantzsch Ester Synthesis. Synlett (Georg Thieme Verlag KG). 2016-04-26, 27 (12): 1810–1813. ISSN 0936-5214. doi:10.1055/s-0035-1561441.

[11] Williams, Robert J.; Lyman, Carl M. The Use of Ammonium Acetate as a Buffer. Journal of the American Chemical Society (American Chemical Society (ACS)). 1932, 54 (11): 4458–4458. ISSN 0002-7863. doi:10.1021/ja01350a503.

[12] Berman, Elena S. F.; Fortson, Susan L.; Checchi, Kyle D.; Wu, Ligang; Felton, James S.; Kuang Jen, J. Wu; Kulp, Kristen S. Preparation of single cells for imaging/profiling mass spectrometry. J Am Soc Mass Spectrom. 2008, 19 (8): 1230–1236. PMID 18565760. doi:10.1016/j.jasms.2008.05.006 .

[13] Australia New Zealand Food Standards Code Standard 1.2.4 - Labelling of ingredients. [2011-10-27]. （原始內容存檔於2013-09-02）.

[14] Barthakur, Madan. Ammonium Acetate. Synlett (Georg Thieme Verlag KG). 2007, 2007 (9): 1475–1476. ISSN 0936-5214. doi:10.1055/s-2007-980375.

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