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Progress in Chemistry 2019, Vol. 31 Issue (9): 1303-1313 DOI: 10.7536/PC190137 Previous Articles   Next Articles

Direct Synthesis of Organic Compounds Using Calcium Carbide as the Acetylene Source

Rugang Fu1,**(), Zheng Li2, Lei Gao2   

  1. 1. Key Laboratory of Hexi Corridor Resources Utilization of Gansu, College of Chemistry and Chemical Engineering, Hexi University, Zhangye 734000, China
    2. College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China
  • Received: Online: Published:
  • Contact: Rugang Fu
  • About author:
    ** E-mail:
  • Supported by:
    The Key laboratory of Hexi Corridor Resources Utilization of Gansu(No.XZ1802)
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Traditionally, calcium carbide is a widely used raw material in organic synthesis. It is always first converted into acetylene gas and subsequently used to prepare organic compounds. Acetylene gas is inflammable and explosive, posing the problem of storage and transportation. In addition, directly using acetylene gas as precursor needs harsh reaction conditions and complicated operation, which greatly limits its further application. Recently, it is shown that calcium carbide could be quickly prepared from renewable biochar at relatively low temperature. Such progress allows calcium carbide as a green and economical raw material. Therefore, the direct use of calcium carbide as a green acetylene source instead of acetylene gas and acetylene reagent to prepare various important organic chemicals will be a simple and green way. In this review, the major progress to date, as well as related reaction types and reaction mechanism towards the application of calcium carbide for specific organic reaction and synthesis have been summarized. The trend of using calcium carbide as a solid acetylene source to construct organic compounds is also prospected.

Key words: calcium carbide, acetylene source, organic synthesis
Fig. 1 Traditional production route of calcium carbide
Fig. 2 Green production route of calcium carbide
Scheme. 1 The representative reaction of acetylene
Fig. 3 Organic chemicals produced from calcium carbide
Scheme. 2 Use of calcium carbide in Aldol condensation/esterification reaction as dehydrant[20, 21]
Scheme. 3 Reaction of calcium carbide with benzyl alcohol[22]
Scheme. 4 Reaction mechanism of calcium carbide with benzyl alcohol[22]
Scheme. 5 Reaction of calcium carbide with natural alcohols[23]
Scheme. 6 Reaction of calcium carbide with epoxides/aromatic ethers[24]
Scheme. 7 Reaction of fluorine mediated calcium carbide with alcohols/phenols[25]
Scheme. 8 Reaction mechanism of alcohols/phenols in CaC2/KF system[25]
Scheme. 9 Reaction of calcium carbide with thiols[26]
Scheme. 10 Reaction mechanism of calcium carbide with thiols[26]
Scheme. 11 Reaction of calcium carbide with disulfides[27]
Scheme. 12 Reaction of calcium carbide with indole/phenol[28]
Scheme. 13 Reaction of calcium carbide and acetone[29]
Scheme. 14 Reaction of calcium carbide with aldehydes/ketones[30]
Scheme. 15 Reaction of fluorine assisted calcium carbide with aldehydes/ketones[31]
Scheme. 16 Reaction mechanism of fluorine assisted calcium carbide with cyclohexanone[31]
Scheme. 17 Reaction of calcium carbide with benzaldehydes[32]
Scheme. 18 Reaction of calcium carbide with cycloketones[33]
Scheme. 19 Reaction of calcium carbide with oximes[34]
Scheme. 20 Reaction mechanism of calcium carbide with oximes[34]
Scheme. 21 Cyclization of calcium carbide with oximes[35]
Scheme. 22 Cyclization of calcium carbide with hydrazone[36]
Scheme. 23 Cyclization of calcium carbide with salicylaldehyde p-tosylhydrazones/2-hydroxyacetopheneones[37]
Scheme. 24 Reaction mechanism of calcium carbide with Salicylaldehyde p-Tosylhydrazones[37]
Scheme. 25 Reaction of calcium carbide with tertiary amines[45]
Scheme. 26 Reaction mechanism of calcium carbide with tertiary amines[45]
Scheme. 27 Reaction of calcium carbide with azides[46]
Scheme. 28 Reaction of calcium carbide with aryl boric acids[47]
Scheme. 29 Reaction of calcium carbide with azides[48]
Scheme. 30 Reaction of calcium carbide with aldehydes and amines[49]
Scheme. 31 Reaction of calcium carbide with aromatic aldehydes and amines[50]
Scheme. 32 Reaction of calcium carbide with aliphatic aldehydes and secondary amines[51]
Scheme. 33 Reaction mechanism of calcium carbide with aliphatic aldehydes and secondary amines[51]
Scheme. 34 Reaction of calcium carbide with isoquinolines and alkyl esters[52]
Scheme. 35 Reaction mechanism of calcium carbide with isoquinoline and alkynyl ester[52]
Scheme. 36 Reaction of calcium carbide with potassium ferrocyanide and aryl iodides[53]
Scheme. 37 Reaction of calcium carbide with alkyl tin halides[54]
Scheme. 38 Reaction of calcium carbide with bromine benzene[55]
Scheme. 39 Reaction mechanism of calcium carbide with bromine benzene[55]
Scheme. 40 Reaction of calcium carbide with iodine benzene[56]
Scheme. 41 The reaction of calcium carbide with benzene diiodobenzenes[57]
Scheme. 42 The reaction of calcium carbide with benzene halides[58]
Scheme. 43 Diagram of the reaction tube of calcium carbide with aryl benzene[58]
Scheme. 44 Reaction of calcium carbide with aryl boric acids/aryl borate esters[59]
Scheme. 45 The mechanism for the reaction of calcium carbide with aryl boric acids[59]
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