4,4′-(Hexafluoroisopropylidene)diphthalic anhydride

4,4′-(Hexafluoroisopropylidene)diphthalic anhydride
Names
	Preferred IUPAC name 5,5′-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)di(2-benzofuran-1,3-dione)
Identifiers
CAS Number	1107-00-2;
3D model (JSmol)	Interactive image;
ChemSpider	63843;
ECHA InfoCard	100.012.882
EC Number	214-170-0;
PubChem CID	70677;
UNII	N2GA6JCU7H ;
CompTox Dashboard (EPA)	DTXSID7061487 ;
	InChI InChI=1S/C19H6F6O6/c20-18(21,22)17(19(23,24)25,7-1-3-9-11(5-7)15(28)30-13(9)26)8-2-4-10-12(6-8)16(29)31-14(10)27/h1-6H Key: QHHKLPCQTTWFSS-UHFFFAOYSA-N;
	SMILES C1=CC2=C(C=C1C(C3=CC4=C(C=C3)C(=O)OC4=O)(C(F)(F)F)C(F)(F)F)C(=O)OC2=O;
Properties
Chemical formula	C19H6F6O6
Molar mass	444.241 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314, H335
Precautionary statements	P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P363, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

Synthesis

The raw materials for 6FDA are hexafluoroacetone and orthoxylene. With hydrogen fluoride as a catalyst, the compounds react to 4,4′-(hexafluoroisopropylidene)bis(o-xylene). This is oxidized with potassium permanganate to 4,4′-(hexafluoroisopropylidene)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

^ U.S. Patent 3310573, "Diaryl fluoro compounds" van 21 maart 1967 aan Du Pont
^ Mrsevic, Miroslav; Düsselberg, David; Staudt, Claudia (2012-05-25). "Synthesis and characterization of a novel carboxyl group containing (co)polyimide with sulfur in the polymer backbone". Beilstein Journal of Organic Chemistry. 8 (1): 776–786. doi:10.3762/bjoc.8.88. ISSN 1860-5397. PMC 3388866. PMID 23015826.
^ Kawakami, Hiroyoshi; Mikawa, Masato; Takagi, Jun; Nagaoka, Shoji (January 1996). "Gas transfer and blood compatibility of fluorinated polyimide membranes". Journal of Biomaterials Science, Polymer Edition. 7 (12): 1029–1038. doi:10.1163/156856296X00525. ISSN 0920-5063. PMID 8880435.

[1] U.S. Patent 3310573, "Diaryl fluoro compounds" van 21 maart 1967 aan Du Pont

[2] Mrsevic, Miroslav; Düsselberg, David; Staudt, Claudia (2012-05-25). "Synthesis and characterization of a novel carboxyl group containing (co)polyimide with sulfur in the polymer backbone". Beilstein Journal of Organic Chemistry. 8 (1): 776–786. doi:10.3762/bjoc.8.88. ISSN 1860-5397. PMC 3388866. PMID 23015826.

[3] Kawakami, Hiroyoshi; Mikawa, Masato; Takagi, Jun; Nagaoka, Shoji (January 1996). "Gas transfer and blood compatibility of fluorinated polyimide membranes". Journal of Biomaterials Science, Polymer Edition. 7 (12): 1029–1038. doi:10.1163/156856296X00525. ISSN 0920-5063. PMID 8880435.

[1]

[2]

[3]