Tetrabutylammonium hydrogen sulfate Property

Melting point:

171-174 °C

Boiling point:

213.3-593.92℃[at 101 325 Pa]

Density 

1.01

vapor pressure 

0Pa at 25℃

storage temp. 

Store below +30°C.

solubility 

H2O: soluble10% (w/v), clear, colorless

form 

Solution

color 

White to beige

Specific Gravity

1.01

PH

1-2 (100g/l, H2O, 20℃)

Odor

Amine like

PH Range

1 - 2

Water Solubility 

Soluble

Sensitive 

Hygroscopic

λmax

λ: 210 nm Amax: 0.06
λ: 220 nm Amax: 0.05
λ: 230 nm Amax: 0.03
λ: 260 nm Amax: 0.02
λ: 500 nm Amax: 0.02

BRN 

3599663

Stability:

Stable, but moisture sensitive. Incompatible with strong oxidizing agents.

InChIKey

SHFJWMWCIHQNCP-UHFFFAOYSA-M

LogP

0.96 at 25℃

CAS DataBase Reference

32503-27-8(CAS DataBase Reference)

NIST Chemistry Reference

Tetrabutylammonium hydrogen sulfate(32503-27-8)

EPA Substance Registry System

Tetrabutylammonium sulfate (1:1) (32503-27-8)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

8-10

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29239000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Tetrabutylammonium hydrogen sulfate Chemical Properties,Usage,Production

Chemical Properties

It is a stable, hygroscopic, white powder.

Uses

A compound that displays antibacterial properties due to the presence of the quaternary amine and the counter ion. Tetrabutylammonium hydrogen sulfate is an ion pairing reagent that is used in liquid chromatography. It is frequently utilized in the analysis of pharmaceutical compounds and metabolites.

Uses

Phase transfer catalyst Tetra-n-butylammonium hydrogen sulfate shows antibacterial properties due to the presence of the quaternary amine and the counter ion. It serves as a phase-transfer catalyst, surface-active agent, solvent, intermediate, active ingredient for conditioners, antistatic agent, detergent sanitizers, softener for textiles and paper products, emulsifying agents and pigment dispersers. Tetrabutylammonium hydrogensulfate is used as a cocatalyst in the synthesis of propionic acid and the ketones by hydrocarboxylation of ethylene. It is also used as an efficient catalyst in the N-alkylation reactions of benzanilides, cyclization of beta-amino acids to beta-lactams, conversion of nitriles to amides, dehydrohalogenation of aryl 2-haloethyl ethers to give vinyl ethers and in the oxidation of alcohols.

Preparation

Tetrabutylammonium hydrogen sulfate can be prepared from tetrabutylammonium azide by treating it with potassium hydrogen sulfate and 10% aqueous sulfuric acid in aqueous medium or from tetrabutylammonium thiocyanate by treating it with relatively concentrated sulfuric acid (70%) at 75 °C.

General Description

Tetrabutylammonium hydrogensulfate, a quaternary ammonium salt, is a phase-transfer reagent. It It serves as solvent for the dissolution of ruthenium(II) complex fac-[Ru(CO)2(H2O)3(C(O)C2H5)][CF3SO3]. It participates as a cocatalyst in the reaction medium for the preparation of alternating polyketones and propionic acid.

Purification Methods

The sulfate crystallises from acetone. It has been used as a phase transfer catalyst.

References

[1] H. N. KARADE M. P K M Sathe. An efficient synthesis of 1, 8-dioxo-octahydroxanthenes using tetrabutylammonium hydrogen sulfate[J]. Arkivoc, 2007, 2007 1. DOI:10.3998/ARK.5550190.0008.D28.
[2] A. J. PARDEY. New media in homogeneous catalysis: wet sodium or tetrabutylammonium hydrogensulfate salts for reppe syntheses catalyzed by a ru(ii) carbonyl complex[J]. Journal of Coordination Chemistry, 2004, 57 1: 871-882. DOI:10.1080/00928970410001721998.
[3] A. J. PARDEY. Hydrocarboxylation and stepwise alternating oligomerization of carbon monoxide and ethylene catalyzed by cis-[Rh(CO)2(amine)2](PF6) complexes in a wet liquid tetrabutylammonium hydrogensulfate[J]. Polyhedron, 2004, 23 1: 1677-1683. DOI:10.1016/J.POLY.2004.03.023.
[4] NEETU TEWARI Rama P T Namrata Dwivedi. Tetrabutylammonium hydrogen sulfate catalyzed eco-friendly and efficient synthesis of glycosyl 1,4-dihydropyridines[J]. Tetrahedron Letters, 2004, 45 49: Pages 9011-9014. DOI:10.1016/j.tetlet.2004.10.057.