Ammonium N-(pyridin-2-ylmethyl)oxamate (AmPicOxam): A Novel Precursor of Calcium Oxalate Coating for Carbonate Stone Substrates
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization
2.2. Reaction of Compound 2 with CaCO3
2.3. Carbonate Stone Samples
2.4. Treatment of Carrara Marble Samples
2.5. Treatment of Biomicritic Limestone Samples
2.6. DFT Calculations
3. Materials and Methods
3.1. Physico-Chemical Characterization
3.2. Scanning Electron Microscopy
3.3. Ultrasonic Measurements
3.4. Colorimetric Measurements
3.5. Powder X-ray Diffraction
3.6. Single Crystal X-ray Diffraction
3.7. Hygric Measurements
3.8. Physico-Mechanical Measurements
3.9. QM Calculations
3.10. Synthesis
3.10.1. Synthesis of O-methyl-N-(pyridin-2-ylmethyl)oxamate (1)
3.10.2. Synthesis of Ammonium N-(pyridin-2-ylmethyl)oxamate (2)
3.10.3. Synthesis of N,N′-bis(pyridin-2-ylmethyl)oxalamide (3)
3.11. Reaction of Compound 2 with CaCO3 Powder
3.12. Coating Preparation
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Weathered White Carrara Marble | Treated Marble (5% w/w) | Treated Marble (12% w/w) | Biomicrite Limestone | Treated Biomicrite (5% w/w) | Treated Biomicrite (12% w/w) | ||
---|---|---|---|---|---|---|---|
Petrography | Mineralogic composition | Calcite, muscovite | Calcite, muscovite, weddellite | Calcite, muscovite, weddellite | Calcite, quartz, muscovite, microcline, albite, chamosite | Calcite, quartz, muscovite, microcline, albite, chamosite, weddellite | Calcite, quartz, muscovite, microcline, albite, hamosite, weddellite |
Dynamics | tuts (µm) | 52.4 ± 0.1 | 56.0 ± 0.1 | 38.9 ± 0.1 | 24.0 ± 0.1 | 27.6 ± 0.1 | 26.0 ± 0.1 |
vuts (km/s) | 1.5 ± 0.1 | 1.4 ± 0.1 | 2.1 ± 0.2 | 3.0 ± 0.2 | 2.9 ± 0.2 | 2.7 ± 0.2 | |
Ed (MN/m2) | 4.23 ± 0.08 | 3.55 ± 0.06 | 7.57 ± 0.19 | 20.3 ± 0.8 | 18.8 ± 0.7 | 16.6 ± 0.6 | |
Structure | ρa (g/cm3) | 2.62 (0.01) | 2.63 (0.01) | 2.63 (0.01) | 1.70 (0.04) | 1.72 (0.02) | 1.75 (0.03) |
ρr (g/cm3) | 2.708 (0.003) | 2.705 (0.006) | 2.711 (0.003) | 2.71 (0.01) | 2.689 (0.001) | 2.686 (0.003) | |
Ic % | 96.75 | 97.23 | 96.83 | 62.73 | 63.96 | 65.15 | |
ɸ % | 3.0 (0.4) | 2.8 (0.2) | 3.1 (0.5) | 29 (2) | 30.7 (0.5) | 29 (1) | |
Colorimetry | L* | 92.90 | 92.60 | 92.40 | 80.30 | 79.20 | 75.60 |
a* | 0.25 | 0.26 | −0.15 | 2.40 | 3.10 | 2.16 | |
b* | 0.26 | 3.70 | 4.91 | 17.70 | 21.70 | 17.14 | |
C | 3.08 | 3.71 | 4.91 | 17.86 | 21.92 | 17.28 | |
WICIELAB76 | 68.56 | 64.92 | 7.38 | – | – | – | |
YIASTME313 | 6.15 | 53.92 | 9.52 | 37.55 | 45.57 | 38.00 | |
ΔE*CIE1976 | – | 0.70 | 0.56 | – | 4.21 | 2.29 | |
ΔE*CIE2000 | – | 3.13 | 2.27 | – | 4.74 | 3.35 | |
Roughness | Ra (µm) | 2.6 (0.3) | 2.8 (0.2) | 2.8 (0.4) | 15 (1) | 17 (2) | 14 (3) |
Rz (µm) | 27 (5) | 30 (5) | 19 (4) | 122 (20) | 137 (8) | 76 (11) | |
Rq (µm) | 3.4 (0.4) | 3.8 (0.3) | 4 (1) | 19 (2) | 21 (3) | 17 (3) |
CA | ΔCA | DI | ΔDI | Po | ΔPo | ρr | Δρr | ρapp | Δρapp | |
---|---|---|---|---|---|---|---|---|---|---|
Carrara white marble | ||||||||||
Untreated | 7.16 | – | 31.86 | – | 5.70(4) | 2.6(0.2) | – | 2.7(0.2) | ||
Treated with 2 | 4.76 | −33.5% | 27.61 | 13.33% | 4.0(4) | –30% | 2.9(0.1) | 1.5% | 3.2(0.2) | –19% |
Biomicritic limestone | ||||||||||
Untreated | 13.22 | – | 3.95 | – | 41.0(3) | – | 2.8(0.2) | – | 1.7(0.1) | – |
Treated with 2 | 9.01 | −31.8% | 2.76 | −30.1% | 38.0(3) | –7% | 2.3(0.1) | –18% | 1.3(0.1) | –24% |
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Pintus, A.; Aragoni, M.C.; Carcangiu, G.; Caria, V.; Coles, S.J.; Dodd, E.; Giacopetti, L.; Gimeno, D.; Lippolis, V.; Meloni, P.; et al. Ammonium N-(pyridin-2-ylmethyl)oxamate (AmPicOxam): A Novel Precursor of Calcium Oxalate Coating for Carbonate Stone Substrates. Molecules 2023, 28, 5768. https://doi.org/10.3390/molecules28155768
Pintus A, Aragoni MC, Carcangiu G, Caria V, Coles SJ, Dodd E, Giacopetti L, Gimeno D, Lippolis V, Meloni P, et al. Ammonium N-(pyridin-2-ylmethyl)oxamate (AmPicOxam): A Novel Precursor of Calcium Oxalate Coating for Carbonate Stone Substrates. Molecules. 2023; 28(15):5768. https://doi.org/10.3390/molecules28155768
Chicago/Turabian StylePintus, Anna, M. Carla Aragoni, Gianfranco Carcangiu, Veronica Caria, Simon J. Coles, Eleanor Dodd, Laura Giacopetti, Domingo Gimeno, Vito Lippolis, Paola Meloni, and et al. 2023. "Ammonium N-(pyridin-2-ylmethyl)oxamate (AmPicOxam): A Novel Precursor of Calcium Oxalate Coating for Carbonate Stone Substrates" Molecules 28, no. 15: 5768. https://doi.org/10.3390/molecules28155768