Sulfonated graphene as highly efficient and reusable acid carbocatalyst for the synthesis of ester plasticizers
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- Μύρων Δαγκλής
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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 204 Supporting information for publication Sulfonated graphene as highly efficient and reusable acid carbocatalyst for the synthesis of ester plasticizers Bhaskar Garg, Tanuja Bisht and Yong-Chien Ling* Contents: Characterization data S2-S3 H and 3 C NMR spectrum of TBC S4-S5 H and 3 C NMR spectrum of THC S6-S7 H and 3 C NMR spectrum of TIBC S8-S9 H and 3 C NMR spectrum of DBP S0-S H and 3 C NMR spectrum of DP S2-S3 H and 3 C NMR spectrum of DIBP S4-S5 S
2 Tributyl citrate (TBC) H NMR (600 MHz, DMS-d 6, 298K): δ = 4.58 (bs, H, -H), 4.02 (t, 2H), 3.96 (t, 4H), 2.84(d, 2H, J = 5.2 Hz, -CH 2 ), 2.70 (d, 2H, J = 5.3 Hz, -CH 2 ), (m, 6H), (m, 6H), and 0.85(t, 9H); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = 72.50, (C=), 72.9 (C), 64.53, (--CH 2 ), 43.05, 34.74, 30.4, 8.62 (-CH 2 ), and 3.5 (-CH 3 ). Triethyl citrate (TEC) H NMR (600 MHz, DMS-d 6, 298K): δ = 6.0 (bs, H, -H), 4.09 (t, 2H), 3.99 (t, 4H), 2.80 (d, 2H, J = 5.2 Hz, -CH 2 ), 2.66 (d, 2H, J = 5.2 Hz, -CH 2 ), and. (t, 9H); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = 73.02, (C=), (C), 6.24, (--CH 2 ), (-CH 2 ), and 4.4 (-CH 3 ). Trimethyl citrate (TMC) H NMR (600 MHz, DMS-d 6, 298K): δ = 5.88 (bs, H, -H), 3.76 (s, 3H, -CH 3 ), 3.65 (s, 3H, -CH 3 ), 2.78 (d, 2H, J = 5.3 Hz, -CH 2 ), and 2.9 (d, 2H, J = 5.3 Hz, -CH 2 ); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = 75.52, (C=), (C), 55.02, (-CH 3 ), and (-CH 3 ). Tri-n-octyl citrate (TC) H NMR (600 MHz, DMS-d 6, 298K): δ = 4.04 (t, 2H), 3.96 (t, 4H), 2.8 (d, 2H, J = 5.6 Hz, -CH 2 ), 2.70 (d, 2H, J = 5.6 Hz, -CH 2 ), (m, 2H),.29 (br, 24H), and 0.85 (t, 9H); 3 C NMR (50 MHz, DMSd 6, 298K): δ = 74.25, (C=), (C), 64.75, (--CH 2 ), 42.67, 32.56, 3.3, 28.05, 27.94, 25.25, 25.07, (-CH 2 ), and 3.77 (-CH 3 ). Tri-n-hexyl citrate (THC) H NMR (600 MHz, DMS-d 6, 298K): δ = 4.0 (t, 2H), 3.95 (t, 4H), 2.83 (d, 2H, J = 5.5 Hz, -CH 2 ), 2.69 (d, 2H, J = 5.6 Hz, -CH 2 ), (m, 6H),.24 (br, 8H), and 0.84 (t, 9H); 3 C NMR (50 MHz, DMSd 6, 298K): δ = 72.44, 69.4 (C=), (C), 64.76, (--CH 2 ), 43.0, 32.56, 30.96, 28.06, 25.08, (-CH 2 ), and 3.77 (-CH 3 ). Triisobutyl citrate (TIBC) H NMR (600 MHz, DMS-d 6, 298K): δ = 5. (bs, H, -H), 3.8 (d, 2H, J = 6.4 Hz, --CH 2 ), 3.7 (d, 4H, J = 6.4 Hz, --CH 2 ), 2.87 (d, 2H, J = 5.2 Hz, -CH 2 ), 2.76 (d, 2H, J = 5. Hz, -CH 2 ), (m, 2H, - CH-), (m, H, -CH-), 0.84 (d, 2H, J = 6.6 Hz, -CH 3 ), and 0.79 (d, 6H, J = 6.6 Hz, -CH 3 ); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = 72.74, 69.6 (C=), (C), 7.3, 70.3 (--CH 2 ), (- CH 2 ), 30.74, (-CH-), 9.22 and 9.00 (-CH 3 ). Triisopropyl citrate (TIPC) H NMR (600 MHz, DMS-d 6, 298K): δ = (m, H, --CH-), (m, 2H, --CH-), 2.85 (d, 2H, J = 5.5 Hz, -CH 2 ), 2.79 (d, 2H, J = 5.5 Hz, -CH 2 ),.8 (d, 6H, J = 6.4 Hz, -CH 3 ), and.4 (d, 2H, J = 6.4 Hz, -CH 3 ); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = 74.64, (C=), 72.9 (C), 68.43, (--CH-), (-CH 2 ), 2.62 and 2.57 (-CH 3 ). Tri-n-active amyl citrate (TAAC) H NMR (600 MHz, DMS-d 6, 298K): δ = 4.32 (bs, H, -H), 3.8 (br, 2H, --CH 2 ), 3.7 (br, 4H, --CH 2 ), 2.86 (d, 2H, J = 5.3 Hz, -CH 2 ), 2.74 (d, 2H, J = 5.3 Hz, -CH 2 ), (m, 2H, -CH-), (m, 6H, -CH 2 -), (m, H, -CH-), 0.83 (t, 9H, -CH 3 ), and 0.78 (d, 9H, J = 4.9 Hz, -CH 3 ); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = 72.5, (C=), (C), 68.5, (--CH 2 ), 42.95, (-CH 2 ), 37.3, (-CH-), (-CH 2 ), 6.09 and 0.99 (-CH 3 ). Dibutyl phthalate (DBP) H NMR (600 MHz, DMS-d 6, 298K): δ = 7.6 (dd, 2H, J = 8.7, 3.2 Hz), 7.5 (dd, 2H, J = 8.7, 3.2 Hz), 4.8 (t, 4H, --CH 2 ), (m, 4H, -CH 2 ), (m, 4H, -CH 2 ), 0.82 (t, 6H, -CH 3 ); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = (C=), 3.94 (C), 3.27, (CH, Aromatic), (--CH 2 ), 30.3, 8.74 (-CH 2 ), 3.37 (-CH 3 ). Diethyl phthalate (DEP) S2
3 H NMR (600 MHz, DMS-d 6, 298K): δ = 7.6 (dd, 2H, J = 8.5, 2.9 Hz), 7.5 (dd, 2H, J = 8.5, 2.9 Hz), 4.27 (t, 4H, --CH 2 ),.23 (t, 6H, -CH 3 ); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = (C=), (C), 3.45, (CH, Aromatic), 6.4 (--CH 2 ), 3.87 (-CH 3 ). Dimethyl phthalate (DMP) H NMR (600 MHz, DMS-d6, 298K): δ = 8. (dd, 2H, J = 8.6, 3. Hz), 7.7 (dd, 2H, J = 8.6, 3. Hz), 3.87 (s, 6H, -CH 3 ); 3 C NMR (50 MHz, DMS-d6, 298K): δ = (C=), (C), 3.97, 28.3 (CH, Aromatic), 3.8 (-CH 3 ). Di-n-octyl phthalate (DP) H NMR (600 MHz, DMS-d 6, 298K): δ = 7.6 (dd, 2H, J = 8.8, 3. Hz), 7.5 (dd, 2H, J = 8.8, 3. Hz), 4.5 (t, 4H, --CH 2 ), (m, 4H, -CH 2 ), (m, 20H, -CH 2 ), 0.78 (t, 6H, -CH 3 ); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = (C=), 3.84 (C), 3.00, (CH, Aromatic), 65.0 (-- CH 2 ), 3.30, 28.77, 28.72, 28.04, 25.60, 22. (-CH 2 ), 3.6 (-CH 3 ). Di-n-hexyl phthalate (DHP) H NMR (600 MHz, DMS-d 6, 298K): δ = 7.6 (dd, 2H, J = 8.6, 3. Hz), 7.5 (dd, 2H, J = 8.6, 3. Hz), 4.3 (t, 4H, --CH 2 ), (m, 4H, -CH 2 ),.5-.8 (m, 2H, -CH 2 ), 0.79 (t, 6H, -CH 3 ); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = (C=), 3.97 (C), 3.65, (CH, Aromatic), (--CH 2 ), 3.38, 28.89, 25.60, (-CH 2 ), 3.70 (-CH 3 ). Diisobutyl phthalate (DIBP) H NMR (600 MHz, DMS-d 6, 298K): δ = 7.7 (dd, 2H, J = 8.9, 3.2 Hz), 7.6 (dd, 2H, J = 8.9, 3.2 Hz), 3.99 (d, J = 6.6 Hz, 4H, --CH 2 ), (m, 2H, -CH-), 0.88 (d, 6H, -CH 3 ); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = (C=), 3.87 (C), 3.22, (CH, Aromatic), 7.02 (--CH 2 ), (CH, Aliphatic), 8.82 (-CH 3 ). Di-n-active amyl phthalate (DAAP) H NMR (600 MHz, DMS-d 6, 298K): δ = 7.7 (dd, 2H, J = 8.8, 3.0 Hz), 7.6 (dd, 2H, J = 8.8, 3.0 Hz), (m, 2H, --CH 2 ), (m, 2H, --CH 2 ), (m, 2H, -CH), (m, 4H, -CH 2 ), 0.88 (d, 6H, -CH 3 ), 0.84 (t, 6H, -CH 3 ); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = (C=), 3.96 (C), 3.27, (CH, Aromatic), (--CH 2 ), 37.2 (CH, Aliphatic), (-CH 2 ), 6.04, 0.90 (-CH 3 ). Di(2-ethylhexyl) phthalate (DEHP) H NMR (600 MHz, DMS-d 6, 298K): δ = 7.7 (dd, 2H, J = 8.8, 3. Hz), 7.5 (dd, 2H, J = 8.8, 3. Hz), (m, 4H, --CH 2 ), (m, 2H, -CH), (q, 4H, -CH 2 ), (m, 2H, -CH 2 ), 0.85 (t, 6H, -CH 3 ), 0.80 (t, 6H, -CH 3 ); 3 C NMR (50 MHz, DMS-d 6, 298K): δ = 67.8 (C=), (C), 32.23, (CH, Aromatic), 66.9 (--CH 2 ), (CH, Aliphatic), 29.35, 28.62, 23.9, (-CH 2 ), 4.22, 2.36 (-CH 3 ). S3
4 H Figure S. H NMR spectrum of tributyl citrate (TBC) S4
5 H Figure S2. 3 C NMR spectrum of tributyl citrate (TBC) S5
6 H Figure S3. H NMR spectrum of trihexyl citrate (THC) S6
7 H Figure S4. 3 C NMR spectrum of trihexyl citrate (THC) S7
8 H Figure S5. H NMR spectrum of triisobutyl citrate (TIBC) S8
9 H Figure S6. 3 C NMR spectrum of triisobutyl citrate (TIBC) S9
10 Figure S7. H NMR spectrum of dibutyl phthalate (DBP) S0
11 Figure S8. 3 C NMR spectrum of dibutyl phthalate (DBP) S
12 Figure S9. H NMR spectrum of dioctyl phthalate (DP) S2
13 Figure S0. 3 C NMR spectrum of dioctyl phthalate (DP) S3
14 Figure S. H NMR spectrum of diisobtyl phthalate (DIBP) S4
15 Figure S2. 3 C NMR spectrum of diisobtyl phthalate (DIBP) S5
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