From Petrochemical Polyurethanes to Biobased Polyhydroxyurethanes, Macromolecules, vol.46, pp.3771-3792, 2013. ,
Non-isocyanate polyurethanes: from chemistry to applications, RSC Adv, vol.3, p.4110, 2013. ,
Isocyanate-Free Routes to Polyurethanes and Poly(hydroxy Urethane)s, Chem. Rev, vol.115, pp.12407-12439, 2015. ,
URL : https://hal.archives-ouvertes.fr/hal-01365096
, Green Chemistry : Theory and Practice, Oxford Uni, 1998.
How well can renewable resources mimic commodity monomers and polymers?, J. Polym. Sci. Part A Polym. Chem, vol.50, pp.1-15, 2012. ,
Green polymer chemistry and bio-based plastics: Dreams and reality, Macromol. Chem. Phys, vol.214, pp.159-174, 2013. ,
,
Novel green fatty acid-based bis-cyclic carbonates for the synthesis of isocyanate-free poly(hydroxyurethane amide)s, RSC Adv, vol.4, p.25795, 2014. ,
Solubility in CO2 and carbonation studies of epoxidized fatty acid diesters: towards novel precursors for polyurethane synthesis, Green Chem, vol.12, p.2205, 2010. ,
URL : https://hal.archives-ouvertes.fr/hal-00679371
Activated lipidic cyclic carbonates for non-isocyanate polyurethane synthesis, Polym. Chem, vol.7, pp.1439-1451, 2016. ,
URL : https://hal.archives-ouvertes.fr/hal-01364916
New aromatic amine based on cardanol giving new biobased epoxy networks with cardanol, Eur. J. Lipid Sci. Technol, vol.117, pp.178-189, 2015. ,
URL : https://hal.archives-ouvertes.fr/hal-01113805
Long-Chain Linear C 19 and C 23 Monomers and Polycondensates from Unsaturated Fatty Acid Esters, Macromolecules, vol.44, pp.4159-4166, 2011. ,
Polyamide precursors from renewable 10-undecenenitrile and methyl acrylate via olefin cross-metathesis, Green Chem, vol.14, p.2179, 2012. ,
URL : https://hal.archives-ouvertes.fr/hal-00864808
Polyamides based on the renewable monomer, 1,13-tridecane diamine II: Synthesis and characterization of nylon 13,6, Polym. (United Kingdom), vol.54, pp.1141-1149, 2013. ,
Highly efficient oxyfunctionalization of unsaturated fatty acid esters: an attractive route for the synthesis of polyamides from renewable resources ,
Preparation and synthetic applications of cyano compounds, Triple-Bonded Funct. Groups, vol.2, 1983. ,
Designer magnets containing cyanides and nitriles, Acc. Chem. Res, vol.34, pp.563-570, 2001. ,
March's Advanced Organic Chemistry: Reactions, Mechanisms, And Structure 7th edition, 2013. ,
One step synthesis of acetonitrile from ethanol via ammoxidation over Sb-V-P-O/Al2O3 catalsy, J. Chem. Soc. Chem. Commun, pp.234-235, 1993. ,
Catalytic oxidative synthesis of nitriles directly from primary alcohols and ammonia, Angew. Chemie -Int. Ed, vol.48, pp.6286-6288, 2009. ,
Metal oxidecatalyzed ammoxidation of alcohols to nitriles and promotion effect of gold nanoparticles for one-pot amide synthesis, Appl. Catal. A Gen, pp.85-90, 2012. ,
Copper(II)-catalysed aerobic oxidation of primary alcohols to aldehydes, Chem. Commun, pp.2414-2419, 2003. ,
Chemoselective Oxidation of Alcohols to Carbonyl Compounds Catalyzed by a DABCO-Copper Complex under Mild Conditions, Adv. Synth. Catal, vol.349, pp.2253-2258, 2007. ,
Aerobic Oxidation of Benzylic Alcohols in Water by 2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO)/Copper(II) 2-N -Arylpyrrolecarbaldimino Complexes, Adv. Synth. Catal, vol.351, pp.2625-2632, 2009. ,
Highly practical copper(I)/TEMPO catalyst system for chemoselective aerobic oxidation of primary alcohols, J. Am. Chem. Soc, vol.133, pp.16901-16911, 2011. ,
Copper-catalyzed aerobic oxidative synthesis of aryl nitriles from benzylic alcohols and aqueous ammonia, Org. Biomol. Chem, vol.11, pp.3349-54, 2013. ,
Highly practical synthesis of nitriles and heterocycles from alcohols under mild conditions by aerobic double dehydrogenative catalysis, Org. Lett, vol.15, pp.1850-1853, 2013. ,
Copper-Catalyzed Synthesis of Nitriles by Aerobic Oxidative Reaction of Alcohols and Ammonium Formate, European J. Org. Chem, vol.2013, pp.5106-5110, 2013. ,
Copper/TEMPO catalysed synthesis of nitriles from aldehydes or alcohols using aqueous ammonia and with air as the oxidant, Chem. Commun, vol.49, pp.6030-6032, 2013. ,
Quantitative synthesis of bis(cyclic carbonate)s by iron catalyst for non-isocyanate polyurethane synthesis, Green Chem, vol.17, pp.373-379, 2015. ,
Long-Chain Aliphatic Polymers To Bridge the Gap between Semicrystalline Polyolefins and Traditional Polycondensates, Chem. Rev, vol.116, pp.4597-4641, 2016. ,
, aqueous ammonia (0.29 mL). 1 H NMR (CDCl3, 25 °C, 400 MHz) ? (ppm): 5.38 (m, 2H), vol.2
, CuI (122 mg, 0.64 mmol, 20 mol%), bpy (100 mg, 0.64 mmol, 20 mol%), TEMPO (100 mg, 0.64 mmol, 20 mol%), acetonitrile (5 mL) and aqueous ammonia (0.5 mL). 1 H NMR (CDCl3, 25 °C, Figure S8: 1 H NMR spectrum in CDCl3 of nitrile obtained from oleyl alcohol. (*) Impurities From citronellol: citronellol (0.5 g, 3.2 mmol)
, CD3OD, 25 °C, 100 MHz) ? (ppm): 41.96 (CH2-NH2), p.2916, 2850.
, Figure S15: 1 H NMR spectra in CD3OD of UndC20-diamine. (*) Impurities
, After 3 days, the reactor was cooled down to RT and slowly depressurized to the atmospheric pressure. The mixture was reconcentrated on rotary evaporator. The 1 H NMR of the final mixture revealed a conversion of 98%. The UndCC-ether was purified by flash chromatography using a mixture of cyclohexane and ethyl acetate (100:0 to 81:19), and obtained as a viscous transparent liquid, 16H). 13 C NMR (CDCl3, 25°C, 100 MHz) ? (ppm):137.9 (CH=CH2), 113.2 (CH=CH2), 70.7 (OCH2-CH2), 70.4 (CH2O-CH2CH2), vol.49, p.1760
Into a round-bottom flask, the UndCC-ether (5g, 18.5 mmol) and 1 st generation Grubbs catalyst (76.2 mg, 0.093 mmol, 0.5% mol) were charged under nitrogen. The contents were vigorously stirred at 35°C for 24 hours. The equilibrium was driven thank to the removal under vacuum of the produced ethylene. The product was then purified with flash chromatography using a mixture of dichloromethane and methanol as eluent ,
Stacked 1 H NMR spectra of (1) undecen-1-ol ,
, Und-bCC-ether was obtained as a grey solid. Yield=53%. 1 H NMR (CDCl3, 25°C, 400 MHz) ? (ppm): 5.38 (m, 2H), 4.80 (m, 2H), 4.49 and 4.39 (t, 4H), 3.64 (m, 4H), 3.50 (t, 4H), 1.97 (m, 4H), 1.56 (m, 6H), 1.27 (m, 26H). 13 C NMR (CDCl3, 25°C, 100 MHz) ? (ppm): 154.5 (OCOO), vol.130
, CH2-CH=CH), vol.32, pp.2-2, 1141.
, C NMR (CDCl3, 25°C, 100 MHz) ? (ppm): 173.0 (CH2-OCO-CH2), 154.5 (OCOO), 130.5 (CH=CH), 73.7 (CH-CH2-OCO), 65.7 (CH2-CH-CH2-OCO), vol.62
, 1 eq of dried diglycerol (5 g, 30 mmol) was mixed with 15 eq of dimethyl carbonate (40.7 g, 452 mmol) and heated up to 90°C. 0.05 eq of La2O3 (0.49 g, 1.5 mmol) was then inserted and the contents were PHUs were synthesized from Und-bCC-ether, Und-bCC-ester, and with 1,10-decanediamine (10DA) and UndC20-diamine (20DA) as comonomers. The polymerizations were, DGDC synthesis : : Into a round-bottom flask equipped with a refrigerant
, Figure S20: 1 H NMR spectrum of PHU1 from 10 DA and Und-bCC-ester. Analysis performed in DMSO) (* : residual monomers