Data for: Optimization of an eco-friendly dyeing process in both laboratory scale and pilot scale supercritical carbon dioxide unit for polypropylene fabrics
Description
IR and 1H NMR of the new synthesized dyes Butyl 4-((2-(3-chlorophenyl)-1-cyano-2-oxoethyl) diazenyl) benzoate (3a) This compound was obtained as Yellow crystals from ethanol, 90 % yield, m.p 140-142 oC. IR (ν/cm-1): 1481.06-1565.23(N=N), 1602.2(C=C aromatic), 1639.2 (C=O), 1700.91(C=O), 2223.05(CN), 2873.42(CH saturated), 2958.27 (CH unsaturated), 3216.88(NH), 1HNMR (500MHz,CDCl3): δ 0.999(3H, t, CH3), 1.476(2H, m, CH2), 1.65(2H, m, CH2), 4.058(1H, s, CH(CN)(CO)), 4.346(2H, t, OCH2), 7.285(2H, m, Ar-H), 7.493(2H, m, Ar-H), 7.594-7.625(1H, m, Ar-H), 7.905(1H, m, Ar-H), 8.013(1H, t, Ar-H), 8.13 (2H, m, Ar-H),9.487 (1H, s, NH exchange with D2O).MS (ESI) m/z Calc. for C20H18ClN3O3 (383.5). found 383.1[M]+,384.09[M+1]+, 385.09 [M+2]+. Pentyl-4-((2-(3-chlorophenyl)-1-cyano-2-oxoethyl) diazenyl) benzoate (3b) This compound was obtained as Yellow crystals from ethanol, 96% yield, IR (ν/cm-1): 1484.48-1535.06 (N=N), 1604.48 (C=C aromatic), 1639.2 (C=O), 1697.05(C=O), 2210.02(CN), 3216.68(NH). 1H-NMR (500MHz,DMSO-D): δ 0.917(3H, m), 1.04(2H , m), 1.209 (2H, m), 1.585 (2H, m), 4.261(2H, m, CH(O)(CO)), 4.775 (1H, S, CH(CO)(CN)), 7.435 (2H, d, Ar-H), 7.516(1H, m, Ar-H), 7.716(1H, m, Ar-H), 7.818 (1H ,d, Ar-H), 7.914(1H,m, Ar-H), 7.948 (2H, m, Ar-H), 12.65 (1H, s, NH exchange with D2O ).13C-NMR (125.76MHz, DMSO-D): δ 22.341, 24.5, 25.5, 30.248, 39.5, 111.06, 114.519, 116.064, 126.804, 127.93, 128.454, 128.826, 129.713, 130.14, 130.934, 132.079, 132.737, 132.813, 145.661, 166.074, 186.028.MS (ESI) m/z Calc. for C21H20ClN3O3( 397.5). found 397.12 [M]+, 398.12 [M+1]+, 399.16 [M+2]+. Hexyl -4-(2-(2-(3-chlorophenyl)-1-cyano-2-oxoethylidene) hydrazinyl) benzoate (3c): This compound was obtained as Yellow crystals from ethanol, 95 % yield, IR (ν/cm-1): 1484.48-1535.06(N=N), 1604.48 (C=C aromatic), 1639.2(C=O), 1697.05 (C=O), 2210.02(CN), 3216.68(NH). 1H-NMR (500MHz, CDCl3) : δ 0.911(3H, t), 1.271(2H, m), 1.346 (2H, m), 1.452 (2H, m), 1.78 (2H, m), 4.334(2H, m, CH(O)(CO)), 7.433(2H, t, Ar-H), 7.586-7.607(2H, m, Ar-H), 7.998-8.016(2H, m, Ar-H), 8.095-8.142(2H, m, Ar-H), 9.6(1H, s, NH exchange with D2O). 13C-NMR (125.76MHz, CDCl3): 14.009, 22.546, 25.693, 28.65, 31.455, 65.449, 115.459, 116.451, 128.316, 129.852, 130.262, 130.92, 131.464, 131.683, 133.906, 134.707, 170.704, 170.714.MS (ESI) m/z Calc. for C22H22ClN3O3 (411.5). found 411.02[M]+, 412.02[M+1]+, 413.13[M+2]+. Butyl 4-((5-amino-3-(3-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl) diazenyl) benzoate (4a): This compound was obtained as Orange crystals from ethanol, 70 % yield, m.p: 188-190oC. IR (ν/cm-1): 1373.07-1488.78 (N=N), 1608.34(C=C aromatic), 1714.48 (C=O), 2873.42 (CH saturated), 2958.27 (CH unsaturated), 3201.26-3293.82 (NH2). 1H-NMR (500MHz, DMSO-D ): δ0.925(3H, m, CH3), 1.425(2H, m, CH2), 1.701(2H, m, CH2), 4.268(2H, t, OCH2), 6.644(2H, s, NH2 exchange with D2O), 7.306 (2H, dd, Ar-H), 7.358 (2H, t, Ar-H), 7.418 (3H, m, Ar-H) ,7.49 (2H, m, Ar-H), 7.798(2H, m, Ar-H), 8.047(2H, m, Ar-H).13C NMR (1