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羟胺

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羟胺
IUPAC名
hydroxylamine
识别
CAS号 7803-49-8  ✓
PubChem 787
ChemSpider 766
SMILES
InChI
InChIKey AVXURJPOCDRRFD-UHFFFAOYAD
Gmelin 478
3DMet B01184
EINECS 232-259-2
ChEBI 15429
RTECS NC2975000
KEGG C00192
MeSH Hydroxylamine
性质
化学式 NH2OH
摩尔质量 33.0298 g·mol⁻¹
外观 白色固体
密度 1.21 g/cm3
熔点 33 °C
沸点 110 °C
溶解性 可溶于冷水,热水中分解
结构
偶极矩 0.67553 D
热力学
ΔfHmo298K −39.9 kJ/mol
So298K ? J K−1 mol−1
危险性
警示术语 R:R5, R22, R37/38, R41, R43, R48/22, R50
安全术语 S:S2, S22, S26, S36/37/39, S61
欧盟分类 Xn, N
NFPA 704
NFPA 704.svg
3
3
1
 
相关物质
相关化学品 盐酸羟胺硫酸羟胺
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

qiǎng(英语:Hydroxylamine),又称羟基胺,可看作NH3中的一个HOH取代而形成的衍生物,其分子式为NH2OH。室温下为不稳定的白色晶体,容易潮解[1] 常以水溶液的形式使用。

1999年来,两家生产羟胺的工厂发生了爆炸,但羟胺的爆炸性原理尚不明确。[2] 研究表明,二价或三价铁盐会催化50%羟胺溶液的分解,羟胺及衍生物最好以盐的形式储存。

羟胺有顺式和反式两种异构体,固态时为反式,气态可能是顺式和反式的混合物。

生产

NH2OH的生产方法有以下几种:

  • 0°C下,用HSO4/SO2还原亚硝酸铵的水溶液,生成[NH4]2[N(OH)(OSO2)2],进一步水解得到硫酸羟胺(NH3OH)2SO4
NH4NO2 + 2SO2 + NH3 + H2O → [NH4]2[N(OH)(OSO2)2]
[NH4]+2[N(OH)(OSO2)2]2− + H2O → [NH4][NH(OH)(OSO2)] + [NH4][HSO4]
2[NH4]+[NH(OH)(OSO2)] + 2H2O → [NH3(OH)]2[SO4] + [NH4]2[SO4]
HNO2 + 2 HSO3 → [N(OH)(OSO2)2]2− + H2O → [NH(OH)(OSO2)] + [HSO4]
[NH(OH)(OSO2)] + H3O+ (100 °C/1 h) → [NH3(OH)]+ + [HSO4]
[NH3(OH)]Cl + NaOBu → NH2OH + NaCl + BuOH[1]

反应

羟胺与亲电试剂,如烷基化试剂反应生成N或O取代产物:

R-X + NH2OH → R-ONH2 + HX
R-X + NH2OH → R-NHOH + HX

反应成

R2C=O + NH2OH∙HCl , NaOH → R2C=NOH + NaCl + H2O

肟通常是具有固定熔点的固体,其生成与分解反应可用于纯化羰基化合物。丁二酮肟等肟类也是常用的配体试剂。

羟胺与氯磺酸反应生成羟胺-O-磺酸,是生产己内酰胺的原料之一:

HOSO2Cl + NH2OH → NH2OSO2OH + HCl

羟胺-O-磺酸应于0°C储存,使用时也需要用碘量法来测定纯度。

还原羟胺及衍生物(R-NHOH)得到[3]

NH2OH (Zn/HCl) → NH3
R-NHOH (Zn/HCl) → R-NH2

羟胺可与金属离子配位,且生成的配合物具有键合异构:M ← NH2OH 和 M ← ONH3

用途

羟胺及其衍生物的用途有:

安全

羟胺对呼吸系统、皮肤、眼部及黏膜具刺激性,吞食有害,为潜在的诱变剂。[5] 羟胺在加热时可能发生爆炸。

参见

参考资料

  1. ^ 1.0 1.1 Greenwood and Earnshaw. Chemistry of the Elements. 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431-432. 1997.
  2. ^ Japan Science and Technology Agency Failure Knowledge Database 互联网档案馆存档,存档日期2007-12-20..
  3. ^ Smith, Michael and Jerry March. March's advanced organic chemistry : reactions, mechanisms, and structure. New York. Wiley. p. 1554. 2001.
  4. ^ Patnaik, Pradyot. Handbook of Inorganic Chemicals. McGraw Hill. pp. 385-386. 2003.
  5. ^ MSDS Sigma-Aldrich

外部链接

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羟胺
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