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studied organometallic complexes besides salen-based complexes. For example, Maeda et al. [23] studied functionalized Zn(II) TPP (tetraphenylporphyrin) with eight quaternary ammonium bromides at the ortho, meta, or para positions of the meso-phenyl groups (Figure 7a; R=O(CH2)6N+Bu3Br−). The meta-substituted Zn(II) complexes showed very high activity. At 20 °C, they reported a cyclic carbonate yield of 82% with a TON (turnover number) of 1640 in 48 h under Processes 2020, 8, 548 10 of 22 atmospheric pressure of CO2. A very high TON of 240,000 can be achieved by increasing reaction temperature to 120 °C and initial CO2 pressure to 17 bar. In a mechanistic approach, DFT (density all different epoxides could be converted to cyclic carbonates with 100% selectivity at 20 ◦C under functional theory) calculation was employed to reveal the origin of merit of the meta-substituted atmospheric pressure, however, with low to moderate yields of 32–49% within 12–24 h of reaction time. catalyst. (a) (b) (c) Figure 7. Non-salen-based complexes: (a) metalloporphyrin-based complex; (b) binuclear aluminum Figure 7. Non-salen-based complexes: (a) metalloporphyrin-based complex; (b) binuclear aluminum scorpionate; (c) trinuclear aluminum scorpionate. scorpionate; (c) trinuclear aluminum scorpionate. Bimetallic Non-Salen Complexes De et al. [24] reported the synthesis of nonsymmetric aza-oxa cryptand derivatized with L- proline. The trinuclear Co(II) complex {[Co3(L)2(NCS)6]·(15CH3CN) (5acetone)(6H2O)} can be formed Castro-Osma et al. [25] studied bimetallic alluminium scorpionate as non-salen complexes by reacting the cryptand and Co(II) perchlorate in the presence of KSCN. With TBAB as a co-catalyst, (Figure 7b) and other organometallic complexes. Bimetallic aluminium scorpionate (Figure 7b; all different epoxides could be converted to cyclic carbonates with 100% selectivity at 20 °C under R = CH(Ph)Me and X = Et) shows the added benefit of using a bimetallic complex that is very atmospheric pressure, however, with low to moderate yields of 32%–49% within 12–24 h of reaction high active over monometallic complex catalysts. However changing this from a large alkyl group time. (R = CH(Ph)Me; X = Et) to a simple aryl group (R = Ph; X = Me) resulted in a significant decrease in catalytic activity, which is also lower than the activity of the monometallic complex. This is critically Bimetallic Non-Salen Complexes due to the nature of the subtituted group attached to the enamine nitrogen atom. Castro-Osma et al. [25] studied bimetallic alluminium scorpionate as non-salen complexes Trimetallic Non-Salen Complexes (Figure 7b) and other organometallic complexes. Bimetallic aluminium scorpionate (Figure 7b; R=CHIn(Pth)eMseamanedsXtu=dEyt,)Cshaoswtros-tOhesmadadetdabl.e[n2e5f]itaolsfousiynngtahebsiimzedtaltlricmceotmalplilcexaltuhmatiinsivuemryshcoigrhpiaocntiavte over monometallic complex catalysts. However changing this from a large alkyl group (Figure 7c) by adding trialkylaluminium to the oxygen atom of the previous bimetallic complex. (ORn=CthHe(bPahs)iMs oef; TXa=bElet)1,toallatrsiimeptalelliacrsyplrogvroiduepco(Rm=pPlhe;teXc=oMnvee)rrseiosnulotefdSOinwaithsi9g7n.i3f%icayniteldeocfresatysreenine catalytic activity, which is also lower than the activity of the monometallic complex. This is critically carbonate, except R = (S)-CH(Ph)Me; X = Me given 92% conversion and 90.2% yield at 10 bar and due to the nature of the subtituted group attached to the enamine nitrogen atom. room temperature for 24 h. Among trimetallic non-salen complexes, only R = Ph; X = Me can maintain the highest catalytic activity of 97.3% yield of styrene carbonate when the CO2 opearting pressure decreases to 1 bar. Another example is trimetallic amine-bis(benzotriazole phenolate) complexes with Ni(II), Co(II), and Zn (II) metal centers [26]. Trimetallic-nickel, trimetallic-cobalt, and trimetallic-zinc achieved conversion of 43%, 67%, and 91%. All the catalysts displayed the same trend of catalytic systems, for which TBAB gave better conversion as a co-catalyst than TBAI. A reasonable explanation for TBAB as a better co-catalyst for the cycloaddition of CO2 with CHO might be attributed to the balance between nucleophilicity and leaving ability of the bromide anion. 3.2. Heterogeneous Catalyst Various heterogeneous catalysts have been developed for the past few decades. The high demand for heterogeneous catalysts is due to the simple separation process [30]. In addition, the advantages of heterogeneous catalyst employment is their high recyclability and recovery of the product and catalyst [5]. However, due to their relatively low catalytic activity, most heterogeneous catalytic systemsPDF Image | Green Pathway Utilizing CO2 Cycloaddition Reaction Epoxide
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