New perfluorovinylethers through the bis(fluoroxy)difluoromethane (BDM) chemistry

Author(s): Navarrini, W; Corti, S.

Source: JOURNAL OF FLUORINE CHEMISTRY

Volume: 125 Issue: 2 Pages: 189-197

DOI: 10.1016/j.jfluchem.2003.07.011 Published: FEB 2 2004

ABSTRACT:

In the present work we give an overview of the CF2(OF)(2) radical reactivity and report the synthesis of new perfluorovinylethers. CF2=CF-OCF2OCF2CF3 and CF2=CF-OCF2OCF2CF2OCF3 are prepared in a semi-continuous methodology starting from CF2(OF)(2). These highly reactive vinylethers are characterized by the OCF2O group directly bonded to the insaturation. For this reason they are excellent candidates for the preparation of very low T-g perfluororubbers.

http://www.sciencedirect.com/science/article/pii/S0022113903002732

Perfluoro-4-methyl-1,3-dioxole: a new monomer for high-T-g amorphous fluoropolymers

Author(s): Russo, A; Navarrini, W.

Source: JOURNAL OF FLUORINE CHEMISTRY

Volume: 125 Issue: 1 Pages: 73-78

DOI: 10.1016/j.jfluchem.2003.10.009 Published: JAN 1 2004

ABSTRACT:

A 4-Chloro-5-trifluoromethyl-2,2,4-trifluoro-1,3-dioxolane (1) was synthesised by reaction of CF2(OF)(2) with CF3-CH=CFCl; the elimination of HCl from (1) in basic conditions led to the formation of dioxole perfluoro-4-methyl-1,3-dioxole (2). Both these synthetic steps gave the corresponding product in high yield. A new synthetic route for the preparation of CF3-CH=CFCl, starting from CF2ClBr and CH2=CF2, together with some examples of polymerisation products obtained by reaction of dioxole (2) with fluoroolefins are also reported.

http://www.sciencedirect.com/science/article/pii/S0022113903003099

Copolymers of perfluorodioxoles

US Patent: 6335408

Date: Gen 1 2002

Inventors: Walter. Navarrini, Antonio Russo

US6335408B1 – PDF

Hydro-Fluoroalkylvinylethers and Process for Obtaining Them

US Patent: 6300526 B1

Date: Oct. 9, 2001

Inventors: W. Navarrini, A. Russo

US6300526 B1 – PDF

Crown ethers as pre-organised exo-receptors in the divergent recognition of alpha,omega-diiodoperfluoroalkanes

Author(s): Navarrini, W; Metrangolo, P; Pilati, T; Resnati, G.

Source: NEW JOURNAL OF CHEMISTRY

Volume: 24 Issue: 10 Pages: 777-780

DOI: 10.1039/b002247k Published: 2000

ABSTRACT:

Both the nitrogen atoms of Kryptofix(R) 2.2. 1 act as electron-donors to the iodine atoms of alpha,omega-diiodoperfluoroalkanes 2a,b giving rise to infinite 1D chains 3a,b as white crystalline solids which are stable in air at room temperature. The structural features of these non-covalent co-polymers have been studied using various techniques (IR, H-1 NMR, F-19 NMR, X-ray diffraction) and it has been established that when Kryptofix 2.2. is halogen bonded to iodides 2, it adopts the same conformation as when in the pure form, namely the exo-exo topology. The co-existence of halogen-bonding and hydrogen-bonding in supramolecular architectures 3 suggests pre-organisation of the interacting partners as a new strategy in the rational design of divergent self-assembly processes.

http://pubs.rsc.org/en/Content/ArticleLanding/2000/NJ/b002247k#!divAbstract

Infrared and Raman analyses of the halogen-bonded non-covalent adducts formed by alpha,omega-diiodoperfluoroalkanes with DABCO and other electron donors

Author(s): Messina, MT; Metrangolo, P; Navarrini, W; Radice, S; Resnati, G; Zerbi, G.

Source: JOURNAL OF MOLECULAR STRUCTURE

Volume: 524 Pages: 87-94

DOI: 10.1016/S0022-2860(99)00445-7 Published: JUN 13 2000

ABSTRACT:

An attractive intermolecular interaction which has been called “halogen bonding” exists between the nitrogen, sulfur, or oxygen atoms present in HC motifs and the iodine atom of PFC residues. The “halogen bonding” is strong enough to overcome the low affinity existing between PFC and HC compounds, driving their self-assembly into supramolecular architectures. The non-covalent co-polymer formed by 1,2-diiodotetrafluoroethane with diazabicyclooctane has been prepared and characterised by FT-IR and -Raman spectroscopies. We propose the changes shown by the vibrational spectra of single PFC and HC components when involved in halogen bonded co-polymers as diagnostic probes of the interaction and as tools to rank the electron-donor ability of differently heteroatom substituted hydrocarbons.

http://www.sciencedirect.com/science/article/pii/S0022286099004457

COD ID: 7051307

From Repository: Crystallography Open Database.

Author(s): Navarrini, Walter; Metrangolo, Pierangelo; Pilati, Tullio; Resnati, Giuseppe

Source: Crystallography Open Database Source URL: http://www.crystallography.net/information_card.php?cif=7051307 Published Year: 2000

Compounds Containing Triazine Ring

US Patent: 5910587

Date: Jun. 8, 1999

Inventors: I. Wlassics, W. Navarrini

US5910587 – PDF

Organic hypofluorites and their new role in industrial fluorine chemistry

Author(s): Navarrini, W; Tortelli, V; Russo, A; Corti, S.

Source: JOURNAL OF FLUORINE CHEMISTRY

Volume: 95 Issue: 1-2 Pages: 27-39

DOI: 10.1016/S0022-1139(98)00296-6 Published: JUN 4 1999

ABSTRACT:

In this work a historical background of the synthesis and chemistry of fluorinated organic hypofluorites is given and some of the known applications of this class of compounds are reviewed. Recently, new industrial processes based on hypofluorite chemistry have been developed for the production of a variety of fluoromonomers. These processes are all based on the addition of hypofluorites having different structures to fluorinated olefins. Some mechanistic features of this key reaction are discussed, in terms of reactivity and stability of the intermediate primary radicals deriving from homolytic cleavage of the hypofluorite bond. Various aspects of these new processes are described and, in the light of these recent achievements, it is shown how hypofluorite chemistry has acquired great importance as a powerful and versatile methodology for the production of fluoromonomers of prominent industrial interest.

http://www.sciencedirect.com/science/article/pii/S0022113998002966

Fluoroelastomeric Compositions

US Patent: 5902857

Date: May 11, 1999

Inventors: I. Wlassics, V. Tortelli, W. Navarrini, M. Albano

US5902857 – PDF

Process for preparing perhaloethers from perhaloolefins and new perhaloethers thereby obtained

US Patent: 5877357

Date: Feb 03 1999

Inventors: Marraccini Antonio, Pasquale Antonio, Fiorani, Tiziana, Navarrini Walter.

US5877357 – PDF

Process for Preparing Fluoroxy-or Chloroxy-Perfluoroacylefluorides

US Patent: 5756841

Date: May 26, 1998

Inventors: D. D. Desmarteau, J. D. O. Anderson, W. Navarrini

US5756841 – PDF

Floorinated Polymers and Copolymers Containing Cyclic Structures

US Patent: 5710345

Date: Jan. 20, 1998

Inventors: W. Navarrini, V. Tortelli, A. Zedda

US5710345 – PDF

Phosphazene Derivatives and Use of Same as Stabilizers for Oils and Greases Based on Perfluoropolyethers

US Patent: 5705668

Date: Jan. 6, 1998

Inventors: P. Odello, W. Navarrini, R. D. Chambers, C. Corti

US5705668 – PDF

Process for Preparing Perhaloethers from Perhaloolefins and New Perhaloethers so Obtained

US Patent: 5648560

Date: Jul. 15, 1997

Inventors: A. Marraccini, A. Pasquale, T. Fiorani, W. Navarrini

US5648560 – PDF