4,4′-(Hexafluoroisopropylidene)diphthalic anhydride

4,4′-(Hexafluoroisopropylidene)diphthalic anhydride (6FDA) is an aromatic organofluorine compound and the dianhydride of 4,4'-(hexafluorisopropylidene)bisphthalic acid (name derived from phthalic acid).

4,4′-(Hexafluoroisopropylidene)diphthalic anhydride
Names
IUPAC name
5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.882
EC Number
  • 214-170-0
Properties
C19H6F6O6
Molar mass 444.241 g·mol−1
Hazards
GHS pictograms
GHS Signal word Danger
H314, H318, H335
P260, P261, P264, P271, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P363, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis

The raw materials for 6FDA are hexafluoracetone and orthoxylene. With hydrogen fluoride as a catalyst, the compounds react to 4.4'-(hexafluorisopropylidene)bis(o-xylene). This is oxidized with potassium permanganate to 4,4'-(hexafluorisopropylidene)bisphthalic acid. Dehydration gives the dianhydride 6FDA.[1]

Applications

6FDA is used as monomer for the synthesis of fluorinated polyimides. These are prepared by the polymerisation of 6FDA with an aromatic diamine such as 3,5-diaminobenzoic acid or 4,4'-diaminodiphenyl sulfide.[2] Such fluorinated polyimides are used in special applications, e. g. used to make gas-permeable polymer membranes,[3] in the field of microelectronics and optics, such as optical lenses from polymers, OLEDs, or high-performance CMOS-contact image sensors (CISs).

These polyimides are typically soluble in common organic solvents, facilitating their production and processing. They have very low water absorption, which makes them particularly suitable for special optical applications.

References
  1. U.S. Patent 3310573, "Diaryl fluoro compounds" van 21 maart 1967 aan Du Pont
  2. Miroslav Mrsevic, David Düsselberg, Claudia Staudt. "Synthesis and characterization of a novel carboxyl group containing (co)polyimide with sulfur in the polymer backbone". Beilstein J. Org. Chem. (2012), vol. 8, pp. 776-786.
  3. H. Kawakami, M. Mikawa, J. Takagi, S. Nagaoka. "Gas transfer and blood compatibility of fluorinated polyimide membranes." Journal of Biomaterials Science, Polymer Edition (1996), vol. 7, pp. 1029-1038. PMID 8880435
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