乙おつ酸さん铵

乙おつ酸さん铵
	IUPAC名めい; Ammonium ethanoate
英文えいぶん名めい	Ammonium acetate
识别
CAS号ごう	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
性せい质
化学かがく式しき	C2H7NO2
摩ま尔质量りょう	77.08 g·mol−1
外そと观	白色はくしょく易えき潮解ちょうかい晶あきら体からだ
氣味きみ	轻微乙おつ酸味さんみ
密度みつど	1.17 g/cm3（20 °C）; 1.073 g/cm3（25 °C）
熔点	113 °C（386 K）（）
溶解ようかい性せい（水みず）	102 g/100 mL（0 °C）; 148 g/100 mL（4 °C）; 143 g/100 mL（20 °C）; 533 g/100 mL（80 °C）
溶解ようかい性せい	可か溶于乙おつ醇あつし、SO2、丙へい酮和わ液えき氨
溶解ようかい性せい（甲きのえ醇あつし）	7.89 g/100 mL（15 °C）; 131.24 g/100 g（94.2 °C）
溶解ようかい性せい（二甲基甲酰胺）	0.1 g/100 g
pKa	9.9
pKb	33
磁化じか率りつ	-41.1·10−6 cm3/mol
黏度	21
结构
晶あきら体からだ结构	正せい交晶系けい
热力学がく
ΔでるたfHm⦵298K	−615 kJ/mol
危险性せい
	GHS危险性せい符号ふごう;
GHS提示ていじ词	Warning
H-术语	H303, H316, H320, H333
P-术语	P281, P335
主要しゅよう危害きがい	刺激しげき性せい
NFPA 704	1 1 1
闪点	136 ℃
	致死ちし量りょう或ある浓度：
LD50（中位ちゅうい剂量）	386 mg/kg（小しょう鼠ねずみ，静せい脉注射ちゅうしゃ）
相あい关物质
其他阴离子こ	硝酸しょうさん铵，硫酸りゅうさん銨
其他阳离子こ	乙おつ酸さん钠，乙おつ酸さん鉀
	若わか非ひ注ちゅう明あかり，所有しょゆう数すう据すえ均ひとし出自しゅつじ标准状じょう态（25 ℃，100 kPa）下した。

乙おつ酸さん銨是これ乙おつ酸さん的てき铵盐，分子ぶんし式しき為ためCH₃COONH₄。它是白色はくしょく、易えき潮解ちょうかい的てき晶あきら体からだ，可か以由乙おつ酸さん和わ氨反はん应而成なり。它可以在商しょう业上买到。^[5]

制せい备

乙おつ酸さん铵可以由碳酸铵和かず乙おつ酸さん中和ちゅうわ而成或ある是ぜ由ゆかり冰醋酸さくさん和わ氨气反はん应而成なり：^[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)}

反はん应

乙おつ酸さん铵加热脱水だっすい，生成せいせい乙おつ酰胺：^[7]

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

在ざい有ゆう机つくえ合成ごうせい中ちゅう，乙おつ酸さん铵可用よう来らい引入氮原子げんし。^[7]它和醇あつし在ざい铱催化か剂存在そんざい下か反はん应，生成せいせい叔胺。^[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}

乙おつ酸さん铵、1,3-二に羰基化合かごう物ぶつ和わ苯偶姻衍生物せいぶつ的てき一いち锅法会かい生成せいせい四よん取と代がわ吡咯，反はん应不需要じゅよう溶剂和わ催化剂。^[9]^[7]

在ざい汉奇吡啶合成ごうせい反はん应的てき变种中ちゅう，1,4-二氢吡啶的衍生物可以通过βべーた-羰基羧酸酯、醛和かず乙おつ酸さん铵的反はん应产生せい。^[10]^[7]

用よう处

乙おつ酸さん铵可用作ようさく缓冲物ぶつ质。^[11]由よし于它在ざい低てい压下会かい挥发，因いん此在制せい备质谱样品ひん时被用よう于替代だい不ふ挥发的てき缓冲物ぶつ质。^[12]乙おつ酸さん铵也被ひ用作ようさく食品しょくひん添加てんか剂，食品しょくひん添加てんか剂国际编码为264。它已被ひ澳大利おおとし亚和纽西兰批准ひじゅん使用しよう。^[13]

此外，乙おつ酸さん铵还用よう于纺织和橡とち胶工业、农业和わ食品しょくひん技わざ术以及各种有机つくえ合成ごうせい中ちゅう。^[14]

参考さんこう资料

^ ^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]. （原始げんし内容ないよう存そん档 (PDF)于2022-12-07）.
^ ^3.0 ^3.1 ^3.2 ^3.3 ^3.4 Ammonium acetate. [2022-08-26]. （原始げんし内容ないよう存そん档于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]. （原始げんし内容ないよう存そん档于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]. （原始げんし内容ないよう存そん档 (PDF)于2022-12-07）.

[chemister-3] 3.0 ^3.1 ^3.2 ^3.3 ^3.4 Ammonium acetate. [2022-08-26]. （原始げんし内容ないよう存そん档于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]. （原始げんし内容ないよう存そん档于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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