Synthesis of Solketal Catalyzed by Acid-Modified Pyrolytic Carbon Black from Waste Tires
Abstract
:1. Introduction
2. Results and Discussion
2.1. Physicochemical Characterization of the rCB Samples
2.2. Catalytic Activity in Glycerol Acetalization Reaction with Acetone
3. Materials and Methods
3.1. Functionalization of rCB
3.2. Preparation of rCB Composite
3.3. Physicochemical Characterization of the Catalysts
3.4. Catalytic Tests
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Sample | Sulfonation Time [hour] | Source of -SO3H Group | SBET a [m2/g] | Smicro b [m2/g] | Smeso c [m2/g] | Vtot d [cm3/g] | Vmicro e [cm3/g ×10−4] | D f [nm] |
---|---|---|---|---|---|---|---|---|
rCB | - | - | 75 | 3 | 72 | 0.22 | 0.35 | 28.7 |
rCB_SA_3h | 3 | H2SO4 | 68 | 13 | 55 | 0.19 | 54.61 | 31.1 |
rCB_SA_24h | 24 | H2SO4 | 91 | 17 | 74 | 0.26 | 71.47 | 26.0 |
rCB_BDS_20h | 20 | C6H7NO3S | 60 | 3 | 57 | 0.20 | 3.98 | 28.6 |
G/rCB_SA_3h | 3 | H2SO4 | 111 | 44 | 67 | 0.12 | 196.74 | 13.6 |
Sample | C [wt.%] | H [wt.%] | N [wt.%] | S [wt.%] | O a [wt.%] | Ash b [wt.%] | Total Acidity c [mmol H+/g] | Density of Acid Centers d [mmol H+/m2 ×10−4] |
---|---|---|---|---|---|---|---|---|
rCB | 68.5 | 0.8 | 0.1 | 2.2 | 2.9 | 25.5 | 0.1 | 0.7 |
rCB_SA_3h | 77.0 | 0.9 | 0.1 | 2.3 | 6.1 | 13.6 | 1.0 | 14.0 |
rCB_SA_24h | 69.7 | 0.7 | 0.1 | 1.7 | 6.1 | 21.7 | 0.9 | 9.3 |
rCB_BDS_20h | 72.4 | 1.0 | 0.3 | 1.5 | 4.2 | 20.6 | 0.5 | 7.5 |
G/rCB_SA_3h | 68.5 | 1.7 | 0.1 | 2.3 | 11.9 | 15.5 | 1.9 | 17.1 |
Sample | C | O | S | Si | Zn |
---|---|---|---|---|---|
rCB | 74.0 | 14.9 | 2.2 | 8.4 | 0.5 |
rCB_SA_3h | 76.4 | 15.7 | 3.9 | 4.0 | 0.0 |
G/rCB_SA_3h | 69.9 | 19.8 | 3.9 | 6.4 | 0.0 |
Binding Energy [eV] | Assignment | Sample | ||
---|---|---|---|---|
rCB [%] | rCB_SA_3h [%] | G/rCB_SA_3h [%] | ||
163.0–165.5 | -C-S-C- | 76.9 | 35.8 | 37.5 |
167.5 and 170.5 | -C-SOx-C- | 23.1 | 64.2 | 62.5 |
Binding Energy [eV] | Assignment | Sample | ||
---|---|---|---|---|
rCB [%] | rCB_SA_3h [%] | G/rCB_SA_3h [%] | ||
284.5 | C-C, C-H, C=C | 65.4 | 69.0 | 65.3 |
285.9–286.1 | C-O in phenol, alcohols, ethers, C-S | 19.8 | 17.8 | 18.0 |
287.2–288.0 | C=O in carbonyl and quinone | 6.6 | 3.9 | 6.4 |
288.4–289.7 | O-C=O in carboxyl, esters, carbonate | 3.4 | 5.7 | 5.5 |
>291.0 | π-π* | 4.8 | 3.6 | 4.8 |
Catalyst | Operating Conditions | Catalytic Performance | Ref. |
---|---|---|---|
AC-S-18M | a batch reactor Gly:A molar ratio = 1:1, t = 6 h; RT; 2.7 wt.% of catalyst | XGly = 64%, SSolketal = 98% | [83] |
AC-S-18M | a batch reactor Gly:A molar ratio = 1:4, t = 6 h; RT; 2.7 wt.% of catalyst | XGly = 97%, SSolketal = 96% | [83] |
GC-1:2 | a batch reactor Gly:A molar ratio = 1:3, t = 2 h; RT; 3 wt.% of catalyst | XGly = 84%, SSolketal = 90% | [33] |
BS 9.2 | a batch reactor Gly:P molar ratio = 1:10, t = 2 h; 55 °C; 0.2 wt.% of catalyst | XGly = 90%, SSolketal = 98% | [19] |
SCS1 | a batch reactor Gly:A molar ratio = 1:6, t = 2 h; 70 °C; 5 wt.% of catalyst | XGly = 79%, SSolketal = 76% | [75] |
HSCS1 | a batch reactor Gly:A molar ratio = 1:6, t = 2 h; 70 °C; 5 wt.% of catalyst | XGly = 82%, SSolketal = 98% | [75] |
rCB_SA_3h | a batch reactor Gly:A molar ratio = 1:1, t = 0.5 h; 40 °C; 1 wt.% of catalyst | XGly = 92%, SSolketal = 96% | This work |
G/rCB_SA_3h | a batch reactor; Gly:A molar ratio = 1:1, t = 0.5 h; 40 °C; 1 wt.% of catalyst | XGly = 92%, SSolketal = 97% | This work |
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Kowalska-Kuś, J.; Malaika, A.; Held, A.; Jankowska, A.; Janiszewska, E.; Zieliński, M.; Nowińska, K.; Kowalak, S.; Końska, K.; Wróblewski, K. Synthesis of Solketal Catalyzed by Acid-Modified Pyrolytic Carbon Black from Waste Tires. Molecules 2024, 29, 4102. https://doi.org/10.3390/molecules29174102
Kowalska-Kuś J, Malaika A, Held A, Jankowska A, Janiszewska E, Zieliński M, Nowińska K, Kowalak S, Końska K, Wróblewski K. Synthesis of Solketal Catalyzed by Acid-Modified Pyrolytic Carbon Black from Waste Tires. Molecules. 2024; 29(17):4102. https://doi.org/10.3390/molecules29174102
Chicago/Turabian StyleKowalska-Kuś, Jolanta, Anna Malaika, Agnieszka Held, Aldona Jankowska, Ewa Janiszewska, Michał Zieliński, Krystyna Nowińska, Stanisław Kowalak, Klaudia Końska, and Krzysztof Wróblewski. 2024. "Synthesis of Solketal Catalyzed by Acid-Modified Pyrolytic Carbon Black from Waste Tires" Molecules 29, no. 17: 4102. https://doi.org/10.3390/molecules29174102