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Sodium ethoxide

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Sodium ethoxide Basic information

Product Name:
Sodium ethoxide
Synonyms:
  • Sodium ethoxide 95%
  • Sodium ethoxide 96%
  • Sodium ethoxide solution
  • sodium ethylate solution
  • Sodiumethoxideinethanol
  • Sodium ethoxide, 21% in ethanol, pure
  • SODIUM ETHYLATE SOLUTION, ~21% IN ETHYL ALCOHOL, DENAT.
  • SODIUM ETHOXIDE, 21 WT. % SOLUTION IN DE NATURED ETHYL ALCOHOL
CAS:
141-52-6
MF:
C2H5NaO
MW:
68.05
EINECS:
205-487-5
Product Categories:
  • Organics
  • metal alkoxide
  • Classes of Metal Compounds
  • Na (Sodium) Compounds (excluding simple sodium salts)
  • Typical Metal Compounds
Mol File:
141-52-6.mol
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Sodium ethoxide Chemical Properties

Melting point:
260 °C
Boiling point:
91°C
Density 
0.868 g/mL at 25 °C
vapor density 
1.6 (vs air)
vapor pressure 
<0.1 mm Hg ( 20 °C)
refractive index 
n20/D 1.386
Flash point:
48 °F
storage temp. 
Store at +15°C to +25°C.
solubility 
Soluble in ethanol and methanol.
form 
Liquid
color 
Yellow to brown
Specific Gravity
0.868
PH
13 (5g/l, H2O, 20℃)
Water Solubility 
Miscible
Sensitive 
Moisture Sensitive
Hydrolytic Sensitivity
7: reacts slowly with moisture/water
Merck 
14,8539
BRN 
3593646
Stability:
Reacts violently with acids, water. Incompatible with chlorinated solvents, moisture. Absorbs carbon dioxide from the air. Highly flammable.
CAS DataBase Reference
141-52-6(CAS DataBase Reference)
EPA Substance Registry System
Ethanol, sodium salt (141-52-6)
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Safety Information

Hazard Codes 
F,C,Xi,N
Risk Statements 
11-14-34-36/37/38-68/20/21/22-51/53-20/21/22
Safety Statements 
8-16-26-43-45-36/37/39-36-61
RIDADR 
UN 3274 3/PG 2
WGK Germany 
1
3-8-10-23
Autoignition Temperature
30 - 50 °C
TSCA 
Yes
HazardClass 
4.2
PackingGroup 
II
HS Code 
29051900
Hazardous Substances Data
141-52-6(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 598 mg/kg

MSDS

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Sodium ethoxide Usage And Synthesis

Chemical Properties

White powder, sometimes having brownish tinge; readily hydrolyzes to alcohol and sodium hydroxide.

Physical properties

White or yellowish powder; hygroscopic; darkens and decomposes on exposure to air; decomposes in water forming sodium hydroxide and ethanol; dissolves in absolute ethanol.

Uses

Sodium ethoxide is used in organic synthesis for condensation reactions. It also is a catalyst in many organic reactions.

Uses

Sodium ethoxide, 21% w/w in ethanol is used as a strong base in organic synthesis. It finds application in various chemical reactions such as condensation, esterification, alkoxylation and etherifcation. It is actively involved in Claisen condensation, Stobbe reaction and Wolf-kishner reduction. It is an important starting material for the synthesis of ethyl ester and diethyl ester of malonic acid. In Williamson ether synthesis, it reacts with ethyl bromide to form diethyl ether.

Definition

ChEBI: An organic monosodium salt that has ethoxide as the counterion.

Preparation

Sodium ethoxide is prepared by reacting sodium with absolute ethanol:
2Na + 2C2H5OH → 2C2H5ONa + H2
Sodium in small quantities is added to absolute alcohol at 10°C. The temperature is raised to warming (to about 38°C). The mixture is cooled again and sodium and absolute alcohol are added gradually followed by careful warming. The process is repeated to obtain a sufficient yield of the p

Hazard

As for caustic soda, ethanol. Sodium hydroxide is formed when sodium ethylate is exposed to moisture.

Purification Methods

It is a hygroscopic powder which should be stored under N2 in a cool place. A likely impurity is EtOH which can be removed by warming at 60-80o under high vacuum. It is hydrolysed by H2O to yield NaOH and EtOH. Other impurities, if kept in air for long periods are NaOH and Na2CO3. In this case the powder cannot be used if these impurities affect the reactivity, and a fresh sample should be acquired [IR: Seubold J Org Chem 21 156 1956]. [Beilstein 1 H 311, 1 IV 1289.]

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