Calcium Carbide and its Recent Advances in Biomass Conversion

Siew Ping Teong; Yugen Zhang

doi:10.1016/j.jobab.2020.04.002

Volume 5 Issue 2

May 2020

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Siew Ping Teong, Yugen Zhang. Calcium Carbide and its Recent Advances in Biomass Conversion[J]. Journal of Bioresources and Bioproducts, 2020, 5(2): 96-100. doi: 10.1016/j.jobab.2020.04.002

Citation:

Siew Ping Teong, Yugen Zhang. Calcium Carbide and its Recent Advances in Biomass Conversion[J]. Journal of Bioresources and Bioproducts, 2020, 5(2): 96-100. doi: 10.1016/j.jobab.2020.04.002

Siew Ping Teong, Yugen Zhang. Calcium Carbide and its Recent Advances in Biomass Conversion[J]. Journal of Bioresources and Bioproducts, 2020, 5(2): 96-100. doi: 10.1016/j.jobab.2020.04.002

Citation:

Siew Ping Teong, Yugen Zhang. Calcium Carbide and its Recent Advances in Biomass Conversion[J]. Journal of Bioresources and Bioproducts, 2020, 5(2): 96-100. doi: 10.1016/j.jobab.2020.04.002

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Calcium Carbide and its Recent Advances in Biomass Conversion

doi: 10.1016/j.jobab.2020.04.002

Siew Ping Teong,
Yugen Zhang^,

Institute of Bioengineering and Nanotechnology, 31 Biopolis Way, the Nanos, Singapore 138669, Singapore

More Information

Corresponding author: Yugen ZHANG, E-mail addresses:ygzhang@ibn.a-star.edu.sg
Received Date: 2020-01-21
Accepted Date: 2020-02-19
Publish Date: 2020-05-01

Abstract

Abstract

Calcium carbide (CaC₂) is a sustainable source of acetylene which plays an important role in organic synthesis due to its active triple bonds and terminal protons. Solid CaC₂ has several advantages over acetylene gas such as easy handling, convenient storage and transportation. The CaC₂ is considered as a safer and more convenient source of acetylene. The chemistry of the CaC₂ is not confined to its use as a source of acetylene and its applications are not limited to the known reactions of acetylene. With the CaC₂ chemistry being actively developing recently, it may eventually lead to the development of new transformations of alkyne chemistry. Herein, this mini review is focused on the synthesis and application of the CaC₂ in biomass transformations.
- calcium carbide (CaC₂),
- biomass,
- transformation,
- conversion

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References(45)

References

Chuentragool, P., Vongnam, K., Rashatasakhon, P., Sukwattanasinitt, M., Wacharasindhu, S., 2011. Calcium carbide as a cost-effective starting material for symmetrical diarylethynes via Pd-catalyzed coupling reaction. Tetrahedron 67, 8177-8182. doi: 10.1016/j.tet.2011.08.042

Favorskii, A.E., 1905. Action of potassium hydroxide on mixtures of ketones and phenylacetylene, Zh. Russ. Fiz.-Khim. O-va. 37, 643-645.

Favorskii, A.E., 1907. Action of caustic potential on the mixing of ketones with phenylacetylene. Bull. Soc. Chim. Fr. 2, 1087-1088.

Galkin, K.I., Ananikov, V.P., 2016. Alkynes as a versatile platform for construction of chemical molecular complexity and realization of molecular 3D printing. Russ. Chem. Rev. 85, 226-247. doi: 10.1070/RCR4611

Hosseini, A., Pilevar, A., Hogan, E., Mogwitz, B., Schulze, A.S., Schreiner, P.R., 2017. Calcium carbide catalytically activated with Tetra-n-butyl ammonium fluoride for Sonogashira cross coupling reactions. Org. Biomol. Chem. 15, 6800-6807. doi: 10.1039/C7OB01334E

Hosseini, A., Seidel, D., Miska, A., Schreiner, P.R., 2015. ChemInform abstract:fluoride-assisted activation of calcium carbide:a simple method for the ethynylation of aldehydes and ketones. ChemInform 46, 2808-2811. http://med.wanfangdata.com.cn/Paper/Detail/PeriodicalPaper_PM25997788

Kim, C.S., Baddour, R.F., Howard, J.B., Meissner, H.P., 1979. CaC₂Production from CaO and coal or hydrocarbons in a rotating-arc reactor. Ind. Eng. Chem. Proc. Des. Dev. 18, 323-328. doi: 10.1021/i260070a027

Ledovskaya, M.S., Voronin, V.V., Rodygin, K.S., 2018. Methods for the synthesis of O-, S- and N-vinyl derivatives. Russ. Chem. Rev. 87, 167-191. doi: 10.1070/RCR4782

Ledovskaya, M.S., Voronin, V.V., Rodygin, K.S., Ananikov, V.P., 2020. Efficient labeling of organic molecules using ¹³C elemental carbon:universal access to ¹³C2-labeled synthetic building blocks, polymers and pharmaceuticals. Org. Chem. Front. 7, 638-647. doi: 10.1039/C9QO01357A

Ledovskaya, M.S., Voronin, V.V., Rodygin, K.S., Posvyatenko, A.V., Egorova, K.S., Ananikov, V.P., 2019. Direct synthesis of deuterium-labeled O-, S-, N-vinyl derivatives from calcium carbide. Synthesis 51, 3001-3013. doi: 10.1055/s-0037-1611518

Lehmann, J., 2007. A handful of carbon. Nature 447, 143-144. doi: 10.1038/447143a

Li, G.D., Liu, Q.Y., Liu, Z.Y., Zhang, Z.C., Li, C.Y., Wu, W.Z., 2010. Production of calcium carbide from fine biochars. Angew. Chem. Int. Ed. 49, 8480-8483. doi: 10.1002/anie.201004169

Li, Y.J., Meng, H., Lu, Y.Z., Li, C.X., 2016. Efficient catalysis of calcium carbide for the synthesis of isophorone from acetone. Ind. Eng. Chem. Res. 55, 5257-5262. doi: 10.1021/acs.iecr.6b00484

Li, Z.K., Liu, Z.Y., Wang, R.X., Guo, X.J., Liu, Q.Y., 2018. Conversion of bio-char to CaC₂ at low temperatures-morphology and kinetics. Chem. Eng. Sci. 192, 516-525. doi: 10.1016/j.ces.2018.07.059

Lin, Z.W., Yu, D.Y., Sum, Y.N., Zhang, Y.G., 2012. Synthesis of functional acetylene derivatives from calcium carbide. ChemSusChem 5, 625-628. doi: 10.1002/cssc.201100649

Mabood, F., Jan, M.R., Shah, J., Jabeen, F., Alam, S., Sadiq, M., Hussain, J., Hussain, Z., 2010a. Catalytic conversion of waste inner tube rubber (isobutylene isoprene) into valuable products. J. Chem. Soc. Pak. 32, 767-773. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=495b8f7734b0e6621c53cafbbfd5da6c

Mabood, F., Shah, J., Jan, M.R., Hussain, Z., Jabeen, F., 2010b. Catalytic conversion of waste low density polyethylene into valuable products. J. Chem. Soc. Pak. 32, 574-581. https://www.researchgate.net/publication/286356634_Catalytic_Conversion_of_Waste_Low_Density_Polyethylene_into_Valuable_Products

Matake, R., Adachi, Y., Matsubara, H., 2016. Synthesis of vinyl ethers of alcohols using calcium carbide under superbasic catalytic conditions (KOH/DMSO). Green Chem. 18, 2614-2618 doi: 10.1039/C5GC02977E

Matake, R., Niwa, Y., Matsubara, H., 2015. Phase-vanishing method with acetylene evolution and its utilization in several organic syntheses. Org. Lett. 17, 2354-2357. doi: 10.1021/acs.orglett.5b00827

Pääkkönen, A., Tolvanen, H., Kokko, L., 2019. The economics of renewable CaC₂ and C₂H₂ production from biomass and CaO. Biomass Bioenergy 120, 40-48. doi: 10.1016/j.biombioe.2018.10.020

Parshina, L.N., Oparina, L.A., Gusarova, N.K., Trofimov, B.A., 2019. Towards C1 chemistry:methanol vinylation by CaC₂ in water in the presence of potassium or sodium carbonates. J. Chem. Technol. Biotechnol. 94, 1945-1950. doi: 10.1002/jctb.5976

Rattanangkool, E., Vilaivan, T., Sukwattanasinitt, M., Wacharasindhu, S., 2016. An atom-economic approach for vinylation of indoles and phenols using calcium carbide as acetylene surrogate. Eur. J. Org. Chem. 2016, 4347-4353. doi: 10.1002/ejoc.201600666

Reppe, W., 1956. Vinylierung. Justus Liebigs Ann. Chem. 601, 81-138. doi: 10.1002/jlac.19566010106

Rodygin, K.S., Bogachenkov, A., Ananikov, V.P., 2018a. Vinylation of a secondary amine core with calcium carbide for efficient post-modification and access to polymeric materials. Molecules 23, 648. doi: 10.3390/molecules23030648

Rodygin, K.S., Ananikov, V.P., 2016a. An efficient metal-free pathway to vinyl thioesters with calcium carbide as the acetylene source. Green Chem. 18, 482-486. doi: 10.1039/C5GC01552A

Rodygin, K.S., Gyrdymova, Y.V., Zarubaev, V.V., 2017. Synthesis of vinyl thioethers and bis-thioethenes from calcium carbide and disulfides. Mendeleev Commun. 27, 476-478. doi: 10.1016/j.mencom.2017.09.015

Rodygin, K.S., Kostin, A.A., Ananikov, V.P., 2015. Calcium carbide as a convenient acetylene source in the synthesis of unsaturated sulfides, promising functionalized monomers. Mendeleev Commun. 25, 415-416. doi: 10.1016/j.mencom.2015.11.004

Rodygin, K.S., Vikenteva, Y.A., Ananikov, V.P., 2019. Calcium-based sustainable chemical technologies for total carbon recycling. ChemSusChem 12, 1483-1516. doi: 10.1002/cssc.201802412

Rodygin, K.S., Werner, G., Kucherov, F.A., Ananikov, V.P., 2016b. Calcium carbide:a unique reagent for organic synthesis and nanotechnology. Chem. Asian J. 11, 965-976. doi: 10.1002/asia.201501323

Rodygin, K.S., Werner, I., Ananikov, V.P., 2018b. A green and sustainable route to carbohydrate vinyl ethers for accessing bioinspired materials with a unique microspherical morphology. ChemSusChem 11, 292-298. doi: 10.1002/cssc.201701489

Sum, Y.N., Yu, D.Y., Zhang, Y.G., 2013. Synthesis of acetylenic alcohols with calcium carbide as the acetylene source. Green Chem. 15, 2718. doi: 10.1039/c3gc41269e

Teong, S.P., Chua, A.Y.H., Deng, S.Y., Li, X.K., Zhang, Y.G., 2017a. Direct vinylation of natural alcohols and derivatives with calcium carbide. Green Chem. 19, 1659-1662. doi: 10.1039/C6GC03579E

Teong, S.P., Lim, J., Zhang, Y.G., 2017b. Vinylation of aryl ether (lignin β-O-4 linkage) and epoxides with calcium carbide through C-O bond cleavage. ChemSusChem 10, 3198-3201. doi: 10.1002/cssc.201701153

Teong, S.P., Yu, D.Y., Sum, Y.N., Zhang, Y.G., 2016. Copper catalysed alkynylation of tertiary amines with CaC₂ via sp3 C-H activation. Green Chem. 18, 3499-3502. doi: 10.1039/C6GC00872K

Thavornsin, N., Sukwattanasinitt, M., Wacharasindhu, S., 2014. Direct synthesis of poly(p-phenyleneethynylene)s from calcium carbide. Polym. Chem. 5, 48-52. doi: 10.1039/C3PY01068F

Trofimov, B.A., Atavin, A.S., 1964. About one preparative method of producing vinyl ethers using calcium carbide. Prikl. Khim. Zhurnal. 37, 2706-2708.

Turberg, M., Ardila-Fierro, K.J., Bolm, C., Hernández, J.G., 2018. Altering copper-catalyzed A 3 couplings by mechanochemistry:one-pot synthesis of 1, 4-diamino-2-butynes from aldehydes, amines, and calcium carbide. Angew. Chem. Int. Ed. 57, 10718-10722. doi: 10.1002/anie.201805505

Wang, D., Liu, Z.Y., Liu, Q.Y., 2019a. Efficient conversion of ethanol to 1-butanol and C5-C9 alcohols over calcium carbide. RSC Adv. 9, 18941-18948. doi: 10.1039/C9RA02568E

Wang, D., Liu, Z.Y., Liu, Q.Y., 2019b. One-pot synthesis of methyl-substituted benzenes and methyl-substituted naphthalenes from acetone and calcium carbide. Ind. Eng. Chem. Res. 58, 6226-6234. doi: 10.1021/acs.iecr.9b00175

Werner, G., Rodygin, K.S., Kostin, A.A., Gordeev, E.G., Kashin, A.S., Ananikov, V.P., 2017. A solid acetylene reagent with enhanced reactivity:fluoride-mediated functionalization of alcohols and phenols. Green Chem. 19, 3032-3041. doi: 10.1039/C7GC00724H

Wilson, J.M., 1895. Proceedings of the institute, stated meeting held Wednesday, March 20, 1895. J. Frankl. Inst. 139, 321-341. doi: 10.1016/0016-0032(95)90080-2

Wu, Y.W., Zheng, Q., Weng, C.S, 2018. An experimental study on the detonation transmission behaviours in acetylene-oxygen-Argon mixtures. Energy 143, 554-561. doi: 10.1016/j.energy.2017.11.019

Xu, X.B., Meng, H., Lu, Y.Z., Li, C.X., 2018. Aldol condensation of refluxing acetone on CaC₂ achieves efficient coproduction of diacetone alcohol, mesityl oxide and isophorone. RSC Adv. 8, 30610-30615. doi: 10.1039/C8RA05965A

Yu, D.Y., Sum, Y.N., Ean, A.C.C., Chin, M.P., Zhang, Y.G., 2013. Acetylide Ion (C22-) as a synthon to link electrophiles and nucleophiles:a simple method for enaminone synthesis. Angew. Chem. Int. Ed. 52, 5125-5128. doi: 10.1002/anie.201301019

Zhang, W.W., Wu, H.Y., Liu, Z.Q., Zhong, P., Zhang, L., Huang, X.B., Cheng, J., 2006. The use of calcium carbide in one-pot synthesis of symmetric diaryl ethynes. Chem. Commun., 4826. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=273e80c4c2521fd1dc66ced4b9a5c2c2

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