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

EC Number |

* 214-170-0

PubChem CID

* 70677

UNII |

* N2GA6JCU7H Y

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 pictograms |
GHS Signal word | Danger

GHS hazard statements

| H314, H335

GHS precautionary statements

| 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

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

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" (in en). Beilstein Journal of Organic Chemistry 8 (1): 776–786. doi:10.3762/bjoc.8.88. ISSN 1860-5397. PMID 23015826. PMC 3388866. https://www.beilstein-journals.org/bjoc/articles/8/88.
3. ↑ Kawakami, Hiroyoshi; Mikawa, Masato; Takagi, Jun; Nagaoka, Shoji (January 1996). "Gas transfer and blood compatibility of fluorinated polyimide membranes" (in en). Journal of Biomaterials Science, Polymer Edition 7 (12): 1029–1038. doi:10.1163/156856296X00525. ISSN 0920-5063. PMID 8880435. https://www.tandfonline.com/doi/full/10.1163/156856296X00525.

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*[CID]: Compound ID
*[H314]: Causes severe skin burns and eye damage
*[H335]: May cause respiratory irritation
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P363]: Wash contaminated clothing before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …