乙酸银

乙酸银
别名	醋酸银
识别
CAS号	563-63-3
PubChem	11246
ChemSpider	10772
SMILES	CC(=O)[O-].[Ag+];
InChI	1/C2H4O2.Ag/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1;
InChIKey	CQLFBEKRDQMJLZ-REWHXWOFAJ
EINECS	209-254-9
RTECS	AJ4100000
性质
化学式	AgC2H3O2
摩尔质量	166.912 g/mol g·mol⁻¹
外观	米黄色固体; 有微酸性气味
密度	3.259 g/cm3
沸点	220 °C（分解）
溶解性（水）	1.02 g/100 mL(20 °C)
危险性
警示术语	R：R37/38, R41, R50
安全术语	S：S26, S39, S61
欧盟分类	Xi N
	GHS危险性符号;
H-术语	H315, H319, H335, H400
P-术语	P261, P273, P305+351+338
NFPA 704	0 1 0
	致死量或浓度：
LD50（中位剂量）	36.7 mg/kg (小鼠)
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

乙酸银，又名醋酸银，是无机化合物，结构式为CH₃COOAg（或AgC₂H₃O₂）。它是一种光敏感的白色晶状固体。它是一种有用的试剂，在实验室中作为水溶性银离子源，氧化阴离子。它已被用于一些戒烟药物中。

合成与结构

乙酸银可以由乙酸和碳酸银在45–60 °C反应合成。冷却至室温后，产物以固体析出^[3]。

{\mathsf {Ag_{2}CO_{3}+2CH_{3}COOH\ {\xrightarrow {}}\ 2AgCH_{3}COO+CO_{2}\uparrow +H_{2}O}}

它也可以在浓硝酸银水溶液中与乙酸钠作用，生成沉淀制得。

乙酸银的结构为一对乙酸配体桥接中心的两个银，形成八元Ag₂O₄C₂环^[4]。

乙酸银在乙酸中的溶解度。

反应

羰基

乙酸银与一氧化碳（CO）一起，可以诱导伯和仲胺的羰基化。也可以使用其它银盐，但乙酸银产率最好。

{\mathsf {2R_{2}NH+2AgOAc+CO\ {\xrightarrow {}}\ [R_{2}N]_{2}CO+2HOAc+2Ag}}

加氢

乙酸银在吡啶溶液中吸收氢，并还原出金属银^[5]。

直接邻位芳基化

对于苄胺和N-甲基苄胺，乙酸银在直接邻位芳基化（装在芳环上的两个相邻的取代基）中是一种有用的试剂。该反应需要钯催化，乙酸银需稍过量^[6]。该反应比以前的邻位芳基化方法要短。

用途

在医疗领域，乙酸银被用于口香糖、喷剂和含片，防止吸烟者吸烟。这些产品中的银，随着烟进入吸烟者的口腔中，使吸烟者感受到不愉快的金属味，从而阻止他们吸烟。对500名成年吸烟者超过3个月的时间测试表明，含2.5毫克乙酸银的含片有“适当的疗效”。然而，一个为期12个月的测试却失败了。1974年，乙酸银在欧洲首次作为非处方戒烟含片（Repaton）推出，三年后推出了口香糖（Tabmint）^[7]。

安全

乙酸银对小鼠的腹腔注射LD₅₀为36.7 mg/kg。低剂量的乙酸银使小鼠高度兴奋，运动失调，中枢神经系统受抑，呼吸困难，甚至死亡^[8]。美国FDA建议，醋酸银的短时摄入量应限制在756毫克；摄入过多可能会导致银中毒^[7]^[9]。

参考文献

^ ^1.0 ^1.1 ^1.2 ^1.3 Record of CAS RN 563-63-3 in the GESTIS Substance Database from the IFA（英语：Institute for Occupational Safety and Health）.
^ Datenblatt Silberacetat [Silberacetat安全信息单（MSDS）] (PDF). Herstellers Merck. [15. Januar 2012] （德语）.
^ Logvinenko, V.; Polunina, O.; Mikhailov, Yu; Mikhailov, K.; Bokhonov, B. Study of Thermal Decomposition of Silver Acetate. Journal of Thermal Analysis and Calorimetry. 2007, 90 (3): 813–816. doi:10.1007/s10973-006-7883-9.
^ Leif P. Olson, David R. Whitcomb, Manju Rajeswaran, Thomas N. Blanton, Barbara J. Stwertka "The Simple Yet Elusive Crystal Structure of Silver Acetate and the Role of the Ag−Ag Bond in the Formation of Silver Nanoparticles during the Thermally Induced Reduction of Silver Carboxylates" Chem. Mater., 2006, volume 18, pp 1667–1674. doi:10.1021/cm052657v
^ Wright, Leon; Well, Sol, Mills, G.A. Homogeneous Catalytic Hydrogenation III. Activation of Hydrogen by Cuprous and Silver Acetates in Pyridine and Dodecylamine. Journal of Physical Chemistry. 1955, 59: 1060–1064. doi:10.1021/j150532a016.
^ Lazareva, Anna; Daugulis. Olafs. Direct Palladium-Catalyzed Ortho-Arylation of Benzylamines. 2006, 8: 5211–5213. doi:10.1021/o1061919b.
^ ^7.0 ^7.1 Hymowitz, Norman; Eckholdt, Haftan. Effects of a 2.5-mg Silver Acetate Lozenge on Initial and Long-Term Smoking Cessation. Journal of Preventitive Medicine. 1996, 25 (5): 537–546. PMID 8888321. doi:10.1006/pmed.1996.0087.
^ Horner, Heidi C.; Roebuck, B.D.; Smith, Roger P.; English, Jackson P. Acute toxicity of some silver salts of sulfonamides in mice and the efficacy of penicillamine in silver poisoning. Drug and Chemical Toxicology. 1977, 6: 267–277 [2013-01-25]. （原始内容存档于2020-04-19）.
^ E. J. Jensen, E. Schmidt, B. Pedersen, R. Dahl. Effect on smoking cessation of silver acetate, nicotine and ordinary chewing gum, Influence of smoking history. Psychopharmacology. 1991, 104 (4): 470–474. PMID 1780416. doi:10.1007/BF02245651.

Редкол.: Никольский Б.П. и др. (编). Справочник химика. 2 3-е изд., испр. Л.: Химия. 1971: 1168.
Рипан Р., Четяну И. Неорганическая химия. Химия металлов. 2. М.: Мир. 1972: 871.

扩展阅读

F. H. MacDougall, and S. Peterson. Equilibria in Silver Acetate Solutions. The Journal of Physical Chemistry. 1947, 51 (6): 1346–1361. doi:10.1021/j150456a009.

[GESTIS-1] 1.0 ^1.1 ^1.2 ^1.3 Record of CAS RN 563-63-3 in the GESTIS Substance Database from the IFA（英语：Institute for Occupational Safety and Health）.

[Merck-2] Datenblatt Silberacetat [Silberacetat安全信息单（MSDS）] (PDF). Herstellers Merck. [15. Januar 2012] （德语）.

[ref_new-3] Logvinenko, V.; Polunina, O.; Mikhailov, Yu; Mikhailov, K.; Bokhonov, B. Study of Thermal Decomposition of Silver Acetate. Journal of Thermal Analysis and Calorimetry. 2007, 90 (3): 813–816. doi:10.1007/s10973-006-7883-9.

[4] Leif P. Olson, David R. Whitcomb, Manju Rajeswaran, Thomas N. Blanton, Barbara J. Stwertka "The Simple Yet Elusive Crystal Structure of Silver Acetate and the Role of the Ag−Ag Bond in the Formation of Silver Nanoparticles during the Thermally Induced Reduction of Silver Carboxylates" Chem. Mater., 2006, volume 18, pp 1667–1674. doi:10.1021/cm052657v

[ref_9-5] Wright, Leon; Well, Sol, Mills, G.A. Homogeneous Catalytic Hydrogenation III. Activation of Hydrogen by Cuprous and Silver Acetates in Pyridine and Dodecylamine. Journal of Physical Chemistry. 1955, 59: 1060–1064. doi:10.1021/j150532a016.

[ref_5-6] Lazareva, Anna; Daugulis. Olafs. Direct Palladium-Catalyzed Ortho-Arylation of Benzylamines. 2006, 8: 5211–5213. doi:10.1021/o1061919b.

[ref_4-7] 7.0 ^7.1 Hymowitz, Norman; Eckholdt, Haftan. Effects of a 2.5-mg Silver Acetate Lozenge on Initial and Long-Term Smoking Cessation. Journal of Preventitive Medicine. 1996, 25 (5): 537–546. PMID 8888321. doi:10.1006/pmed.1996.0087.

[ref_3-8] Horner, Heidi C.; Roebuck, B.D.; Smith, Roger P.; English, Jackson P. Acute toxicity of some silver salts of sulfonamides in mice and the efficacy of penicillamine in silver poisoning. Drug and Chemical Toxicology. 1977, 6: 267–277 [2013-01-25]. （原始内容存档于2020-04-19）.

[9] E. J. Jensen, E. Schmidt, B. Pedersen, R. Dahl. Effect on smoking cessation of silver acetate, nicotine and ordinary chewing gum, Influence of smoking history. Psychopharmacology. 1991, 104 (4): 470–474. PMID 1780416. doi:10.1007/BF02245651.

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