Radical telomerisation of vinylidene fluoride with diethyl hydrogenphosphonate

Duc, Michel; Boutevin, Bernard; Améduri, Bruno

doi:10.1016/s0022-1139(01)00475-4

Cited by 27 publications

(34 citation statements)

References 29 publications

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“…In the same way Boutevin et al [40] have studied the telomerization of styrene with the same telogen and have estimated the C T ¼ 9 Â 10 À4 . More recently Duc et al [41] have realized the radical telomerization of difluoroethylene with diethyl hydrogenphosphonate under the same conditions as we used. The authors have obtained telomers with increased molecular weight and have isolated the first four adducts by distillation.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of New Methacrylic Phosphonated Surface Active Monomer

Senhaji

Robin

Achchoubi

et al. 2004

Macro Chemistry & Physics

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Summary: The synthesis of novel methacrylic phosphonated surface‐active monomer by an original method is described. The crucial stage is the telomerization of undec‐10‐enyl acetate with dialkyl (alkyl = methyl or ethyl) hydrogenphosphonate. The phosphonated acetate obtained is selectively hydrolysed to give dialkyl(11‐hydroxyundecyl)phosphonate as a precursor. The alcohol function allows setting of methacrylic side, which is highly reactive in radical polymerization. Particularly, by mono‐dealkylation of dimethyl phosphonate in a selective and quantitative way, the potassium iodide permits to get, at one stage, the expected salt of sodium methyl phosphonate. The new surface‐active sodium methyl(11‐methacryloyloxyundecyl)phosphonate is characterized by 1H and 31P NMR. Its critical micelle concentration evaluated by conductometry is 2.4 × 10−2 mol · l−1.Synthesis of dialkyl(11‐methacryloyloxyundecyl)phosphonate (DAHP) without protection of alcohol function.imageSynthesis of dialkyl(11‐methacryloyloxyundecyl)phosphonate (DAHP) without protection of alcohol function.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of New Methacrylic Phosphonated Surface Active Monomer

Senhaji

Robin

Achchoubi

et al. 2004

Macro Chemistry & Physics

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“…[21][22][23] With respect to our considerations we have chosen the last method and used radical addition of DEHP to the unsaturated compounds, a route already used by many authors from our group. [24][25][26][27][28][29] The reaction was carried out without solvent at The telomerization reaction was monitored by SEC. We observed that the monomer disappeared entirely after a 10 h reaction time, unlike the nonfunctionalized alkenes (of type CH 3 -(CH 2 ) n -CH CH 2 , n ¼ 5, 9 and 15) for which Pelaprat et al [25] obtained 100% product after 5 h at the same temperature.…”

Section: Resultsmentioning

confidence: 99%

“…This is in good agreement with other studies carried out in our laboratory. [24,27,31] After distillation of the excess DEHP, the addition product was isolated with a quantitative yield and characterized by 1 H NMR, 31 P NMR and FT-IR.…”

Section: Resultsmentioning

confidence: 99%

“…Boutevin et al [31] have studied the radical telomerization of styrene with the same telogen (DEHP) and found the C T to be 9 Â 10 À4 . More recently, Duc et al [24] realized the radical telomerization of difluoroethylene with DEHP under the same conditions as those we used. The authors have obtained telomers with increased molecular weight and have separated the first four adducts by distillation.…”

Section: Determination Of the Dehp C T Transfer Constantmentioning

confidence: 98%

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Determination of the Kinetic Constants of the Telomerization of 10‐Undecenol with Alkyl Hydrogenphosphonate

Senhaji

Robin

Achoubi

et al. 2004

Macro Chemistry & Physics

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Summary: The telomerization of 10‐undecenol with alkyl hydrogenphosphonate was studied in order to synthesize telomers of different molecular weights. The study showed that telomers from 10‐undecenol could be obtained despite the fact that the double bond has a low reactivity. The kinetic constant Kp2/KTe was determined to be 7 × 10−4 l · mol−1 · s−1 at 135 °C and the transfer constant CT was 0.057. These values are normal for a low activity telogen such as hydrogenphosphonate and for slightly reactive monomers like 10‐undecenol.SEC chromatogram of telomers obtained in the reaction of 10‐undecenol addition.imageSEC chromatogram of telomers obtained in the reaction of 10‐undecenol addition.

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“…These latters can be produced by the radical telomerization of various fluoroalkenes (tetrafluoroethylene, hexafluoropropylene, vinylidene fluoride, chlorotrifluoroethylene, dichlorodifluoroethylene), [55][56][57][58][59][60][61][62][63] with dialkyl hydrogenophosphate as listed in Table 2 and Scheme 5:…”

Section: Telomerization Of Tfp In the Presence Of Diethyl Hydrogenophmentioning

confidence: 99%

Original fluorinated surfactants potentially non-bioaccumulable

Kostov

Boschet

Améduri

2009

Journal of Fluorine Chemistry

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Radical telomerisation of vinylidene fluoride with diethyl hydrogenphosphonate

Cited by 27 publications

References 29 publications

Synthesis and Characterization of New Methacrylic Phosphonated Surface Active Monomer

Synthesis and Characterization of New Methacrylic Phosphonated Surface Active Monomer

Determination of the Kinetic Constants of the Telomerization of 10‐Undecenol with Alkyl Hydrogenphosphonate

Original fluorinated surfactants potentially non-bioaccumulable

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