HEXAFLUOROACETYLACETONE

HEXAFLUOROACETYLACETONE Property

Boiling point:

70-71 °C (lit.)

Density 

1.47 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.332(lit.)

Flash point:

32 °C

storage temp. 

Inert atmosphere,Room Temperature

form 

Liquid

pka

4.30±0.10(Predicted)

color 

Clear colorless to slightly yellow

Specific Gravity

1.470

Water Solubility 

Not miscible in water.

Sensitive 

Hygroscopic

BRN 

1790138

InChIKey

QAMFBRUWYYMMGJ-UHFFFAOYSA-N

CAS DataBase Reference

1522-22-1(CAS DataBase Reference)

EPA Substance Registry System

2,4-Pentanedione, 1,1,1,5,5,5-hexafluoro- (1522-22-1)

Safety

Hazard Codes 

C,F,Xi

Risk Statements 

10-20/21/22-34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2920 8/PG 2

WGK Germany 

3

F 

3

Hazard Note 

Flammable/Corrosive

TSCA 

T

HazardClass 

8

PackingGroup 

II

HS Code 

29147000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

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.

HEXAFLUOROACETYLACETONE Chemical Properties,Usage,Production

Description

HEXAFLUOROACETYLACETONE acts as a chelating ligand. For example, it can forms metal-chelate complexes with Ca(II), Zn (II), Cu(II), Ni(II), Co(II), Nd(III), Rh(III), Fe(III) and Cr(III), making it be useful in extracting related metal ions. It can also be used as liquid crystal intermediate.

References

Chattoraj, S. C., A. G. C. Jr, and R. E. Sievers. "Cadmium and zinc chelates of hexafluoroacetylacetone the gas phase reaction of a novel volatile cadmium complex with hydrogen sulphide." Journal of Inorganic & Nuclear Chemistry 28.9(1966):1937-1943.
Tomazic, Branko B., and J. W. O'Laughlin. "Synergic extraction of iron with hexafluoroacetylacetone and tributyl phosphate." Analytical Chemistry 45.8(2002):1519-1526.
http://www.sigmaaldrich.com/catalog/product/aldrich/238309?lang=en&region=US
https://www.alfa.com/zh-cn/catalog/L01693/

Chemical Properties

clear colorless to slightly yellow liquid

Uses

1,1,1,5,5,5-Hexafluoro-2,4-pentanedione acts as a chelating ligand. It is used as liquid crystal intermediate.

General Description

Hexafluoroacetylacetone forms metal-chelate complexes with Cu(II), Ni(II), Co(II), Nd(III), Rh(III), Fe(III) and Cr(III). Hexafluoroacetylacetone on hydration yields 1,1,1,5,5,5-hexafluoropentane-2,2,4,4-tetraol.

Synthesis

The general procedure for the synthesis of 1,1,1,5,5,5-hexafluoroacetylacetophenone from 1,1,1,5,5,5-hexafluoroacetylacetophenone dihydrate was as follows: 6.8 g (69 mmol, 4.9 eq.) of concentrated sulfuric acid was slowly added to 3.4 g (14 mmol, 1 eq.) of 1,1,1,5,5,5-hexafluoroacetylacetophenone dihydrate at 10 °C. The reaction mixture was stirred at room temperature for 3 hours and 35 minutes and the formation of a two-phase system was observed. Upon completion of the reaction, the mixture was left to stratify and the dehydrated organic phase was separated to obtain the dehydrated organic phase. 2.7 g of the target product 1,1,1,5,5,5-hexafluoroacetylacetone was finally obtained in 93% yield. The structure of the product was confirmed by 1H-NMR and 19F-NMR: 1H-NMR [internal standard: (CH3)4Si, deuterated solvent: CD3CN] δ 10.45 (2H); 19F-NMR [internal standard: CFCl3, deuterated solvent: CD3CN] δ -77.18 (6F).

Purification Methods

It forms a dihydrate which has no UV spectrum compared with max (CHCl3) 273nm ( 7,800) for the anhydrous ketone. The dihydrate decomposes at ~90o. The hydrate (10g) plus anhydous CaSO4 (Drierite, 30g) are heated and distilled, the distillate is treated with more CaSO4 and redistilled. When the distillate is treated with aqueous NaOH and heated, the dihydrate crystallises on cooling. The Cu complex has m 135o (after sublimation). [Gilman et al. J Am Chem Soc 78 2790 1956, Belford et al. J Inorg Nucl Chem 2 11 1956, Beilstein 1 IV 3681.]

References

[1] Patent: US6384286, 2002, B1. Location in patent: Page column 5-6
[2] Patent: US6384286, 2002, B1. Location in patent: Page column 5
[3] Patent: US6384286, 2002, B1. Location in patent: Page column 5
[4] Patent: US6384286, 2002, B1. Location in patent: Page column 5
[5] Patent: US6384286, 2002, B1. Location in patent: Page column 4 - 5