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Potassium tert-butoxide

Basic information Strong organic alkaline Related chemical reaction Strong alkaline condensing agent Laboratory method for preparation of potassium tert-butoxide Precautions Uses Safety Related Supplier

Potassium tert-butoxide Basic information

Product Name:
Potassium tert-butoxide
CAS:
865-47-4
MF:
C4H9KO
MW:
112.21
EINECS:
212-740-3
Mol File:
865-47-4.mol
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Potassium tert-butoxide Chemical Properties

Melting point:
256-258 °C (dec.)(lit.)
Boiling point:
275°C
Density 
0.910 g/mL at 20 °C
vapor pressure 
1 mm Hg ( 220 °C)
Flash point:
54 °F
storage temp. 
Flammables area
solubility 
Soluble in hexane, toluene, diethyl ether and terahydrofuran.
form 
Solution
color 
White to off-white
Specific Gravity
0.902
PH
13 (5g/l, H2O, 20℃)Hydrolysis
Water Solubility 
REACTS
Sensitive 
Moisture Sensitive
BRN 
3556712
Stability:
Stable, but reacts violently with water and acids, possibly leading to fire. Incompatible with water, acids, halogenated hydrocarbons, alcohols, strong oxidizing agents, ketones, carbon dioxide.
InChIKey
LPNYRYFBWFDTMA-UHFFFAOYSA-N
CAS DataBase Reference
865-47-4(CAS DataBase Reference)
EPA Substance Registry System
2-Methyl-2-propanol, potassium salt (865-47-4)
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Safety Information

Hazard Codes 
F,C,Xi
Risk Statements 
11-19-22-34-35-14-20-36/37-37
Safety Statements 
16-26-36/37/39-43-45-7/9-8-43A-33-27-29
RIDADR 
UN 3274 3/PG 2
WGK Germany 
1
10-21
Autoignition Temperature
483 °C
Hazard Note 
Flammable solid/Corrosive
TSCA 
Yes
HazardClass 
8
PackingGroup 
I
HS Code 
29051900

MSDS

  • Language:EnglishProvider:KtB
  • Language:EnglishProvider:SigmaAldrich
  • Language:EnglishProvider:ACROS
  • Language:EnglishProvider:ALFA
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Potassium tert-butoxide Usage And Synthesis

Strong organic alkaline

Potassium tert-butoxide is an important kind of organic base with its alkalinity being stronger than potassium hydroxide. Because of the induction effect of three methyl groups in the (CH3) 3CO-, it has stronger alkalinity and activity than other potassium alkoxides, thus being a very excellent catalyst. In addition, as a kind of strong alkaline, potassium tert-butoxide is widely used in the organic synthesis of chemical, pharmaceutical, and pesticide such as trans-esterification, condensation, rearrangement, polymerization, loop opening and the production of heavy metal orthoester. It can be used to catalyze the Michael addition reaction, Pinacol rearrangement reaction and Ramberg-Backlund rearrangement reaction. Potassium tert-butoxide is used as a condensing agent, which can be used to catalyze Darzens condensation reaction and Stobbe condensation reaction. It is also the most effective alkaline for traditional akloxide-haloform reaction generating dihalogenated carbene. Therefore, potassium tert-butoxide has attracted more and more attention from chemical, pharmaceutical, pesticide and other industries. As potassium tert-butoxide has such a wide application, the domestic and international demand for high purity potassium tert-butoxide is very large. However, due to its production cost is higher than other alkali metal alkoxides, the production technology needs to be improved, so in-depth study of potassium tert-butoxide is particularly important.

Related chemical reaction

1, Take N-formyl-o-toluidine as raw material, 350~360 °C, have it reacted with potassium tert-butoxide to generate indole. After separation, the indole is further reacted with chloroacetic acid reaction to obtain β-indole acetic acid.
2, β-ring citral is first reacted with acrylic magnesium bromide to have Grignard reaction to generate alcohol, the resulting alcohol is then oxidized into ketone, followed by isomerization using potassium tert-butoxide as a catalyst to become β-ketone.
3, Take citral and allyl Grignard reagents as raw materials for reaction to generate 6, 10-dimethyl-4-hydroxy-1, 5, 9-undecatriene, followed by the oxidation reaction by Collins reagent to generate 6, 10-dimethyl-1,5,9-undecatrien-4-one, which is then subject to isomerization under the action of tert-butanol potassium to generate damascone. The damascone, under the action of Tin chloride or phosphoric acid, can have cyclization to obtain damascenone.
4, Take 2, 6, 6-trimethylcyclohexane-2-alkenyl formaldehyde to have reaction with allyl Grignard agent to generate cyclohexenyl butenol, followed by the oxidation under copper-zinc catalyst to generate cyclohexane alkenyl ketene, followed by isomerization in the alkali solution of potassium tert-butoxide, being able to generate Damascenone.
5, Darzen reaction: aldehydes and ketones, in the presence of alkaline reagents, can have ester-aldol condensation reaction with α-halo acid ester, while having the hydrogen halogen lost, generating α, β-epoxy ester. Common alkaline reagents include sodium ethoxide, sodium amide, sodium metal, potassium tert-butoxide and so on.
6. Stobbe reaction: aldehydes, ketones and succinate ester, in the presence of alkaline catalysts (such as sodium ethoxide, potassium tert-butoxide, sodium chloride, etc.) have reaction similar to the aldol condensation reaction, generating succinate or its monoester with the methylene replaced by hydrocarbon.

Strong alkaline condensing agent

Potassium tert-butoxide is a strong alkaline condensing agent with its alkalinity is stronger than sodium methoxide and sodium ethoxide. At room temperature, this product is white or white-like solid powder with its chemical formula being (CH3) 3C-O-K, molecular weight being 112.21, density being 0.929, the melting point of 256-258 ° C and the boiling point being 275 ° C. It is easy to absorb moisture. It is soluble in tert-butanol with the solution being relative stable, and commonly used in the dehydrohalogenation reaction of halogenated hydrocarbon. Being exposure to air decomposition, it can be decomposed into potassium oxide and tert-butyl alcohol when coming across water. It can be manufactured through the reaction between butanol and potassium, followed by the vacuum distillation of tert-butanol in the system.
It is widely used the condensation reaction, rearrangement and ring-opening reaction in organic synthesis. People generally apply tert-butanol solution. Potassium tert-butoxide is a kind of organic alkaline corrosion products with strong moisture absorption property and should be sealed for storage. We need to pay attention to prevention of fire and sunshine during the storage and transportation. It should be stored in a cool, ventilated and dry place.

Laboratory method for preparation of potassium tert-butoxide

The potassium metal was added to the freshly distilled tert-butanol under nitrogen atmosphere, refluxed to until the potassium was completely melted. Further incubate for 1 hour. The excess amount of t-butyl alcohol was distilled off with the remaining white solid subjecting to vacuum drying under reduced pressure at 180-190 °C for 10 h. Then we can obtain the crystal powder of potassium tert-butanol. It needs to saved be under the nitrogen atmosphere for using. It should be kept away from air & water, or will become pink. The yield, calculated according to potassium, is more than 99%. The chemical reaction equation for the reaction between tert-butyl alcohol and metal potassium for preparation of potassium tert-butoxide is as follows:
The chemical reaction equation for the reaction between tert-butyl alcohol and metal potassium for preparation of potassium tert-butoxide.

Precautions

Potassium tert-butoxide has two types, liquid and solid. Usually the liquid industrial product is the tert-butanol solution of tert-butanol potassium with the color of the product being light yellow or milky white, being slightly turbid, in which the content of potassium tert-butoxide being 10% to 12%; the solid product is generally white or white powder in which the potassium tert-butoxide content is 95% to 97%.
Potassium tert-butoxide is organic alkaline corrosion product with strong moisture absorption property. It should be generally sealed for storage, generally stored in a cool, dry, ventilated warehouse. It should be kept away from heat and isolated from fire isolation as well as being protected from sun exposure. Potassium tert-butoxide has a strong corrosive effect on the skin. During the handling and loading process, the operator should wear a protective mask to prevent corrosion and burning by potassium tert-butoxide.
The above information is edited by Tongtong from Chemicalbook.

Uses

It can be used in pesticides, pharmaceuticals, printing and dyeing, catalysts and so on
Potassium tert-butoxide, as a strong alkaline, is widely used in the condensation, rearrangement and ring opening reaction in organic production in the fields of chemical, pharmaceutical and pesticide.

Chemical Properties

white crystalline powder

Uses

Usually used for greener amidation of esters.

Fire Hazard

Potassium tert-butoxide is a flammable solid. It ignites on heating. Being very strongly basic, its reactions with acids are highly exothermic. Contact of solid powder with drops of sulfuric acid and vapors of acetic acid caused ignition after an induction period of 0.5 and 3 minutes, respectively (Manwaring 1973). Ignition occurs upon reactions with many common solvents of the type ketone, lower alcohols, esters, and halogenated hydrocarbons. Such solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone, methanol, ethanol, n-propanol, isopropanol, ethyl acetate, n-propyl formate, n-butyl acetate, chloroform, methylene chloride, carbon tetrachloride, epichlorohydrin, dimethyl carbonate, and diethyl sulfate (NFPA 1997). Such ignition may arise from accidental contact of the alkoxide with these solvents and may be attributed to sudden release of energy from exothermic reactions. However, slow mixing of the powder with excess solvent will dissipate the heat. It reacts violently with water, producing tert-butanol and potassium hydroxide, as follows:
K―OC―(C4H9)3+H2O → tert-C4H9OH +KOH
The addition of potassium tert-butoxide to the solvent dimethyl sulfoxide can cause ignition of the latter (Bretherick 1995).

Purification Methods

It sublimes at 220o/1mm. The last traces of tert-BuOH are removed by heating at 150-160o/2mm for 1hour. It is best prepared afresh as likely impurities are tert-BuOH, KOH and K2CO3 depending on its exposure to air. Its solubility at 25-26o in hexane, toluene, Et2O, and THF is 0.27%, 2.27%, 4.34% and 25.0%, respectively. [Feuer et.al. J Am Chem Soc 78 4364, Doering & Urban J Am Chem Soc 78 5938 1956, Beilstein 1 IV 1612.]

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CAS:865-47-4
Purity:98% Package:10g;50g;100g;250g;500g
Basic information Strong organic alkaline Related chemical reaction Strong alkaline condensing agent Laboratory method for preparation of potassium tert-butoxide Precautions Uses Safety Related Supplier