Synthesis and Application of Oximes for Mineral Processing and Metallurgy

SUN Qing; WANG Shuai; ZHONG Hong

doi:10.13779/j.cnki.issn1001-0076.2020.02.002

2020 Vol. 40, No. 2

Article Contents

Article navigation > Conservation and Utilization of Mineral Resources > 2020 > 40(2): 10-16

Next Article Previous Article

SUN Qing, WANG Shuai, ZHONG Hong. Synthesis and Application of Oximes for Mineral Processing and Metallurgy[J]. Conservation and Utilization of Mineral Resources, 2020, 40(2): 10-16. doi: 10.13779/j.cnki.issn1001-0076.2020.02.002

Citation:

SUN Qing, WANG Shuai, ZHONG Hong. Synthesis and Application of Oximes for Mineral Processing and Metallurgy[J]. Conservation and Utilization of Mineral Resources, 2020, 40(2): 10-16. doi: 10.13779/j.cnki.issn1001-0076.2020.02.002

Synthesis and Application of Oximes for Mineral Processing and Metallurgy

Hunan Provincial Key Laboratory of Efficient and Clean Utilization of Manganese Resources, College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China

More Information

Corresponding author: ZHONG Hong, zhongh@csu.edu.cn

Received Date: 10 February 2020

Publish Date: 25 April 2020

Abstract

Abstract

Oxime compounds, which have unique chemical reactivity, can coordinate with a variety of metal ions and have broad application prospects. The structures and properties of oximes, including aldoxime, ketoxime, hydroxamic acid and amidoxime, were reviewed. The synthesis methods of new multi-functional chelating oximes, such as carboxyl hydroxamic acid, amide-alkylhydroximic acid, thiol oxime, olefin oxime, amino amidoxime, bis(amidoxime) and oxime polymer, and the improvement of traditional oxime compounds were introduced. The updated progress of their application in the fields of flotation and metallurgy were also reviewed.
- oxime /
- synthesis /
- flotation /
- metallurgy

FullText(HTML)

References

[1]	M. H. Dindar, S. A.M. Fathi, M. R. Yaftian, et al. Solid phase extraction of copper(II) ions using C18-silica disks modified by oxime ligands[J]. Journal of Hazardous Materials, 2010, 179(1-3):289-294. doi: 10.1016/j.jhazmat.2010.02.092 CrossRef Google Scholar
[2]	梁高杰,陈文汨,范尚.赤泥沉降用新型氧肟酸絮凝剂的合成与应用[J].中南大学学报(自然科学版),2017,48(2):295-301. Google Scholar
[3]	安鹏,匙芳廷,文君,等.电子转移活化再生催化剂原子转移自由基聚合法制备吸附剂及其吸铀性能[J].同位素,2018,31(2):84-92. Google Scholar
[4]	G. A. Hope, A. Numprasanthai, A. N. Buckley, et al. Bench-scale flotation of chrysocolla with n-octanohydroxamate[J]. Minerals Engineering, 2012, 36-38:12-20. Google Scholar
[5]	I. Narin, Y. Surme, E. Bercin, et al. SP70-α-benzoin oxime chelating resin for preconcentration-separation of Pb(II), Cd(II), Co(II) and Cr(III) in environmental samples[J]. Journal of Hazardous Materials, 2007, 145(1-2):113-119. doi: 10.1016/j.jhazmat.2006.11.001 CrossRef Google Scholar
[6]	张首才,孙丽娟.二茂铁羟肟酸去除铜(Ⅱ)、镍(Ⅱ)、锌(Ⅱ)、铬(Ⅲ)的研究[J].化学工程师,2009(8):63-64. doi: 10.3969/j.issn.1002-1124.2009.08.021 CrossRef Google Scholar
[7]	贾云,钟宏,王帅,等.捕收剂的分子设计与绿色合成[J].中国有色金属学报,2020,30(2):456-466. Google Scholar
[8]	钟宏,刘威,王帅.一种羟肟酸盐捕收剂的制备方法.201810510460.7[P].2018-05-24. Google Scholar
[9]	颜玲玲,殷志刚,蒋玉仁.2-羟肟基正壬酸对一水硬铝石的浮选脱硅性能[J].广州化学,2010,35(3):26-32. doi: 10.3969/j.issn.1009-220X.2010.03.006 CrossRef Google Scholar
[10]	Y.R. Jiang, Y.F. Pan, D. Chen, et al. A theoretical study of the effect of carboxyl hydroxamic acid on the flotation behavior of diaspore and aluminosilicate minerals[J]. Clays and Clay Minerals, 2012, 60(1):52-62. doi: 10.1346/CCMN.2012.0600105 CrossRef Google Scholar
[11]	L.Q. Deng, S. Wang, H. Zhong, et al. N-(6-(hydroxyamino)-6-oxohexyl) decanamide collector:Flotation performance and adsorption mechanism to diaspore[J]. Applied Surface Science, 2015, 347:79-87. doi: 10.1016/j.apsusc.2015.03.138 CrossRef Google Scholar
[12]	郑林禄,杨发福.醛肟基杯[4]芳烃衍生物的合成及性能研究[J].化学试剂,2013,35(3):282-284. Google Scholar
[13]	肖友军,贺燕华,陈建钗.2-羟基-5-特辛基苯乙酮肟的合成及表征[J].有色金属科学与工程,2014,5(5):97-100. Google Scholar
[14]	张彩霞,舒庆,刘若琳,等.新型铜萃取剂对十二烷基苯基羧基甲酮肟的合成及其萃铜性能[J].有色金属科学与工程,2017,8(6):36-42. Google Scholar
[15]	J.J. Xiao, G.Y. Liu, H. Zhong, et al. The flotation behavior and adsorption mechanism of O-isopropyl-S-[2-(hydroxyimino) propyl] dithiocarbonate ester to chalcopyrite[J]. Journal of the Taiwan Institute of Chemical Engineers, 2017, 71:38-46. doi: 10.1016/j.jtice.2016.12.022 CrossRef Google Scholar
[16]	H.F. Xu, H. Zhong, Q. Tang, et al. A novel collector 2-ethyl-2-hexenoic hydroxamic acid:Flotation performance and adsorption mechanism to ilmenite[J]. Applied Surface Science, 2015, 353:882-889. doi: 10.1016/j.apsusc.2015.06.072 CrossRef Google Scholar
[17]	张严,卢宇熙,王帅,等.偕氨肟捕收剂对石英和磁铁矿的浮选性能[J].矿产保护与利用,2019(4):104-108. Google Scholar
[18]	H. Xu, T.W. Chu, X.Y. Wang, et al. Facile synthesis of bis(hydroxamamide)-based tetradentate ligands for 99mTc-radiopharmaceutical[J]. Applied Radiation and Isotopes, 2005, 62(6):919-922. doi: 10.1016/j.apradiso.2004.12.008 CrossRef Google Scholar
[19]	李海普,梁璀,李学明,等.含异羟肟酸基团的高分子絮凝剂的制备[J].轻金属,2010(5):19-24. Google Scholar
[20]	刘西艳,许璐,张晓敏,等.一种偕胺肟基纤维材料对模拟盐湖水中铀的吸附研究[J].中国科学:化学,2018,48(5):518-526. Google Scholar
[21]	孟勇,苏胜培,毛丽秋,等.丙烯酰胺-丙烯酸-丙烯羟肟酸共聚物乳液脱除电镀废水中的重金属离子[J].化工进展,2009,28(11):2072-2075. Google Scholar
[22]	Z.F. Cao, P. Qiu, S. Wang, et al. Benzohydroxamic acid to improve iron removal from potash feldspar ores[J]. Journal of Central South University, 2018, 25(9):2190-2198. doi: 10.1007/s11771-018-3907-4 CrossRef Google Scholar
[23]	蒋玉仁,胡岳华,曹学锋.新型螯合捕收剂COBA结构与捕收性能的关系[J].中国有色金属学报,2001,11(4):702-706. doi: 10.3321/j.issn:1004-0609.2001.04.035 CrossRef Google Scholar
[24]	王明细,蒋玉仁.新型螯合捕收剂COBA浮选黑钨矿的研究[J].矿冶工程,2002,22(1):56-57. doi: 10.3969/j.issn.0253-6099.2002.01.018 CrossRef Google Scholar
[25]	戴婷,王帅,钟宏.N-烃基酰氨基己基羟肟酸对菱锰矿的浮选性能与吸附机理[J].中国锰业,2018,36(4):142-146. Google Scholar
[26]	L.Q. Deng, H. Zhong, S. Wang, et al. A novel surfactant N-(6-(hydroxyamino)-6-oxohexyl)octanamide:Synthesis and flotation mechanisms to wolframite[J]. Separation and Purification Technology, 2015, 145:8-16. doi: 10.1016/j.seppur.2015.02.029 CrossRef Google Scholar
[27]	肖静晶,刘广义,钟宏.N-丁氧基丙基-S-[2-(肟基)丙基]二硫代氨基甲酸酯浮选孔雀石的疏水机理[J].中国有色金属学报,2018,28(2):416-424. Google Scholar
[28]	S. Liu, H. Zhong, G.Y. Liu, et al. Cu(I)/Cu(II) mixed-valence surface complexes of S-[(2-hydroxyamino)-2-oxoethyl]-N,N-dibutyldithiocarbamate:Hydrophobic mechanism to malachite flotation[J]. Journal of Colloid and Interface Science, 2018, 512:701-712. doi: 10.1016/j.jcis.2017.10.063 CrossRef Google Scholar
[29]	S. Liu, G.Y. Liu, H. Zhong, et al. The role of HABTC's hydroxamate and dithiocarbamate groups in chalcopyrite flotation[J]. Journal of Industrial and Engineering Chemistry, 2017, 52:359-368. doi: 10.1016/j.jiec.2017.04.015 CrossRef Google Scholar
[30]	H.F. Xu, H. Zhong, S. Wang, et al. Synthesis of 2-ethyl-2-hexenal oxime and its flotation performance for copper ore[J]. Minerals Engineering, 2014, 66-68:173-180. Google Scholar
[31]	黄志强.新型阳离子捕收剂的合成及其对铝硅矿物的浮选性能与机理研究[D].长沙:中南大学,2015. Google Scholar
[32]	Q. Kong, X.Z. Bai, H.J. Lin, et al. Improved determination of salicylaldoxime in water samples by liquid-liquid extraction followed by high performance liquid chromatographic analysis[J]. Journal of Central South University, 2018, 25(4):701-708. doi: 10.1007/s11771-018-3774-z CrossRef Google Scholar
[33]	H. Miyasaka, A. Saitoh, S. Yanagida, et al. Nickel(II) and iron(II) mononuclear complexes with 1-methylimidazole-2-aldoximate:New building units for molecule-assembled magnetic materials[J]. Inorganica Chimica Acta, 2005, 358(12):3525-3535. doi: 10.1016/j.ica.2005.05.010 CrossRef Google Scholar
[34]	A. Parus, K. Wieszczycka, A. Olszanowski. Solvent extraction of cadmium(II) from chloride solutions by pyridyl ketoximes[J]. Hydrometallurgy, 2011, 105(3-4):284-289. doi: 10.1016/j.hydromet.2010.10.007 CrossRef Google Scholar
[35]	S. Panigrahi, P. K. Parhi, K. Sarangi, et al. A study on extraction of copper using LIX 84-I and LIX 622N[J]. Separation and Purification Technology, 2009, 70(1):58-62. doi: 10.1016/j.seppur.2009.08.013 CrossRef Google Scholar
[36]	L.Q. Li, H. Zhong, Z.F. Cao, et al. Recovery of copper(II) and nickel(II) from plating wastewater by solvent extraction[J]. Chinese Journal of Chemical Engineering, 2011, 19(6):926-930. doi: 10.1016/S1004-9541(11)60073-6 CrossRef Google Scholar
[37]	K. Prochaska,黄宗良.含两个羟肟基团的螯合萃取剂的界面活性和铜的萃取速率[J].湿法冶金,1995(2):47-50. Google Scholar
[38]	周洁,王劲松,林艳,等.5,11,17,23,29,35-六羧基-37,38,39,40,41,42-六羟肟酸甲氧基杯[6]芳烃对铀(Ⅵ)的萃取[J].环境工程学报,2015,9(11):5315-5321. doi: 10.12030/j.cjee.20151129 CrossRef Google Scholar
[39]	时文中,朱国才.氯化铵氯化-二酰异羟肟酸萃取法从粉煤灰中提取锗的研究[J].河南大学学报(自然科学版),2007(2):147-151,156. doi: 10.3969/j.issn.1003-4978.2007.02.009 CrossRef Google Scholar
[40]	王其观,胡慧萍,陈湘攀,等.含氧肟酸基团絮凝剂的合成及其对赤泥的沉降效果[J].轻金属,2013(8):20-23. Google Scholar
[41]	J. Stemper, W. Tuo, E. Mazarío, et al. Synthesis of bis(amidoxime)s and evaluation of their properties as uranyl-complexing agents[J]. Tetrahedron, 2018, 74(21):2641-2649. doi: 10.1016/j.tet.2018.04.016 CrossRef Google Scholar