ChemInform Abstract: REACTION OF ORGANIC CARBONATES WITH AMINES. III. REACTION OF AMINES WITH ALKYLENE CARBONATES

Abstract

Die Alkylencarbonate (I1), erhalten aus den Epoxiden (I) und CO2, werden mit den Aminen (III) zu den Urethanen (IV) umgesetzt.

Chemo-Enzymatic Synthesis and Characterization of Renewable Thermoplastic and Thermoset Isocyanate-Free Poly(hydroxy)urethanes from Ferulic Acid Derivatives

“…Silica gel flash chromatography was performed on an Interchim puriflash 4100 using a variable cyclohexane/ethyl acetate gradient of elution. Chemical structures of the prepared compounds were determined by 1 H and 13 C NMR spectroscopy with a Bruker Fourier Ultrashield 300 MHz spectrometer at room temperature in (CD 3 ) 2 CO or (CD 3 ) 2 SO. Trimethylsilane was used as external references for 1 H NMR, and shifts are given in ppm.…”

“…1 H NMR (300 MHz, acetone-d 6 , ppm): δ 1.62 (m, 4H, H 1 ), 2.61 (t, 3 J H4−H5 = 9 Hz, 4H, H 4 ), 2.86 (m, 4H, H 5 ), 3.81 (s, 6H, H 12 ), 4.05 (t, 3 J H2−H1 = 6 Hz, H 2 ), 4.22 (dd, 3 J H14−H15 = 12 Hz, 4 J H13−H15 = 3 Hz, 2H, H 15 ), 4.28 (dd, 3 J H14−H15 = 12 Hz, 4 J H13−H15 = 3 Hz, 2H, H 13 ), 4.57 (dd, 3 J H13−H14 = 9 Hz, 4 J H13−H15 = 6 Hz, 2H, H 13 ), 4.69 (t, 2H, H 15 ), 5.15 (m, 2H, H 14 ), 6.77 (dd, 3 J H7−H8 = 6 Hz, 4 J H7−H11 = 3 Hz, 2H, H 7 ), 6.91 (s, 2H, H 11 ), 6.93 (d, 3 J H7−H8 = 6 Hz, 2H, H 8 ). 13 C NMR (75. Overall yield from ferulic acid: 52%.…”

“…The cyclocarbonate-amine reaction, described for the first time in the 1930s by Carothers et al, − has been widely studied and used since the 1960s , and allows us to dispense with isocyanate in polyurethane synthesis. Thus, this NIPU route has attracted the attention of the polymer community − for the syntheses of poly­(hydroxy)­urethane materials and led to the development of some commercial systems.…”

A new way of creating cellular polyurethane materials: NIPU foams

“…Recently, Thebault et al [24,25] prepared non-isocyanate polyurethanes by carbonation of hydrolysable tannin followed by reaction with a primary amine. The cyclic carbonate/amine reaction, already studied in the past by Whelan et al and Mikheev et al [26,27], avoids the use of isocyanates and diamines and permits the formation of poly(hydroxyurethane)s (PHUs) with hydroxyl groups. This method was tremendously studied and has recently attracted much attention, particularly by Endo et al [23,[28][29][30][31] and Figovsky et al [32,33].…”

Absolute Configuration of C2‐Symmetric Spiroselenurane: 3,3,3′,3′‐Tetramethyl‐1,1′‐spirobi[3 H,2,1]Benzoxaselenole

“…2–4 However, diisocyanates are not biobased and are generally very harmful reactants for human health. Therefore, an old reaction is currently gaining much attention as an alternative route for the synthesis of PUs: step‐growth polyaddition of dicyclocarbonates and diamines 5, 6. This method is quite interesting since no hazardous isocyanates are used and dicyclocarbonate reactants can be obtained from renewable resources such as glycerin.…”