洛沙坦类似物的合成研究以及铜渣氯浸渣的脱硫方法研究
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摘要
肾素-血管紧张素系统(RAS)在人体血压调节中起着重要作用。选择性干扰RAS较直接的手段是在受体水平上拮抗AT_1受体激素。就肽类拮抗剂而言,由于其口服吸收有限,持续时间短,使其做为治疗及药理学工具的用途均受到限制。洛沙坦是第一个具有口服活性的非肽类受体拮抗剂,它的发现促进了许多同类药物的研究。我们总结了近些年非肽类AngⅡ受体拮抗剂的研究进展,并分析了洛沙坦的构效关系及其合成策略。本文设计了六个化合物,对它们的合成进行了探索研究,初步得到两个化合物,其他化合物仍在进一步合成研究中。
另外我们还对金川公司二冶炼厂镍电解车间除铜时产生的铜渣氯浸渣进行了物相分析,分别测定了铜渣氯浸渣中硫、镍、铜、氯等元素的含量,并对铜渣氯浸渣进行了脱硫研究,为铜渣氯浸渣的回收利用提供了依据。
The rennin-angiotensin system (RAS) plays an important role in the regulation of blood pressure. An alternate and more direct mode of selectively blocking the RAS is by antagonists of the effector hormone AT_1 at the receptor level. As far as peptide analogs of antagoulsts are concerned, their usefulness as therapeutic agents and pharmacological tools has been hampered by their lack of oral absorption, short duration of action. Lorsatan is the first nonpeptide analogs of antagonist which has better orally activity. Its discovery has stimulated the design of a large number of congeners.we summarized the work of recent nonpeptide AngⅡantagoulsts, explained the structure-activity relationships and the synthesis of Lorsatan. We designed six compounds in this paper, and obtained two compounds. Other compounds were still synthesized furtherly.
In addition, we have studied the phase analysis of copper residue leached by chloride which was generated by nickel electrolytic plant of JinChuan company, determined the contents of sulfur, nickel, copper, chlorine, studied the methods of desulfurization which provided a basis for recycling of copper residue leached by chloride.
另外我们还对金川公司二冶炼厂镍电解车间除铜时产生的铜渣氯浸渣进行了物相分析,分别测定了铜渣氯浸渣中硫、镍、铜、氯等元素的含量,并对铜渣氯浸渣进行了脱硫研究,为铜渣氯浸渣的回收利用提供了依据。
The rennin-angiotensin system (RAS) plays an important role in the regulation of blood pressure. An alternate and more direct mode of selectively blocking the RAS is by antagonists of the effector hormone AT_1 at the receptor level. As far as peptide analogs of antagoulsts are concerned, their usefulness as therapeutic agents and pharmacological tools has been hampered by their lack of oral absorption, short duration of action. Lorsatan is the first nonpeptide analogs of antagonist which has better orally activity. Its discovery has stimulated the design of a large number of congeners.we summarized the work of recent nonpeptide AngⅡantagoulsts, explained the structure-activity relationships and the synthesis of Lorsatan. We designed six compounds in this paper, and obtained two compounds. Other compounds were still synthesized furtherly.
In addition, we have studied the phase analysis of copper residue leached by chloride which was generated by nickel electrolytic plant of JinChuan company, determined the contents of sulfur, nickel, copper, chlorine, studied the methods of desulfurization which provided a basis for recycling of copper residue leached by chloride.
引文
1.李岩,陈玉彬。非肽类血管紧张素Ⅱ受体拮抗剂研究进展,中国药物化学杂志,1998,8(3),220。
2.Sealey L.E.;Laragh J.H.Raven Press:New York,1990,1287.
3.戴生明,朱铨英,苏定冯。血管紧张素Ⅱ(angiotensinⅡ)受体的研究进展,药学实践杂志.1995,13(3),141。
4.1)John V.Duncia,Andrew T.Chiu,David J.Carini,George B.Gregory,Alexander L.Johnson,William A.Price,Gregory J.Wells,Pancras C.Wong,Joseph C.Calabrese,Pieter B.M.W.M.Timmermans.The discovery of potent nonpeptide angiotensin Ⅱ receptor antagonists:a new class of potent antihypertensives J.Med Chem.1990,33,1312;
2)王金东.洛沙坦和氟伐他汀在意大利获准。国外药讯,1995,8,25。
5.张玮,孙武,熊方武。国外上市新药。国外医药-合成药、生化药、制剂分册,1996,17(2),118。
6.Mealy N.;Castaner.Elisartan Potassium.Antihypertensive,Angiotensin Ⅱantagonist.J.Drugs Future,1996,21(2),139.
7.Hilditch A;Hunt A A;Travers A;Polley J;Drew G M;Middlemiss D;Judd D B;Ross B C;Robertson M.GR138950,a novel angiotensin AT1 receptor antagonist.J.Pharmacology,1993,108,239.
8.Kenakin T.The classification of drugs and drug receptors in isolated tissues.Pharmacology Rev.1984,36(3),165.
9.Robison K.A.;Robinson C.P.Saprisartan.Antihypertensive,Angiotensin Ⅱreceptor antagonist.J.Drugs Future,1996,21(11),1129.
10.Vans M.J.A.,Redemann N.Arznein-Forsch,1996,46(8),755.
11.Shibouta Y.;Inada Y.;Ojima M..Nonpeptide angiotensin Ⅱ-receptor antagonists.Yakuri to Chiryo,1996,24(10),2207.
12.Kito G.;Norimoto S.;Shiomi M.Arznein-Forsch,1996,46(1),572.
13.蒋巡天,华维一。非肽类血管紧张素Ⅱ受体拮抗剂的构效关系研究。药学进展,1995,19(3),145。
14.Nathan B.Mantlo,Prasun K.Chakravarty,Debra L.Ondeyka,Peter K.S.Siegl, Raymond S. Chang, Victor J. Lotti, Kristie A. Faust, Terry W. Schorn, Tsing Bau Chen. Potent, orally active imidazo[4,5-b]pyridine-based angiotensin II receptor antagonists. J. Med. Chem. 1991, 34(9), 2919.
15. Wong P.C., Christ D.D., Wong N. Nonpeptide angiotensin II receptor antagonist: pharmacokinetics and pharmacodynamics in rats of EXP3174, an active metabolite of losartan. Pharmacody-namics, 1996, 52(1), 25.
16. M. McIntyre,R. J. MacFadyen, P. A. Meredith, R. Brouard, J. L. Reid. Dose-Ranging Study of the Angiotensin II Receptor Antagonist Irbesartan (SR 47436/BMS-186295) on Blood Pressure and Neurohormonal Effects in Salt-Deplete Men. J. Cardiovascular Pharmacol, 1996, 28 (1), 101.
17. J. S. Harmat Nicholas, Raffaello Giorgi, Fabrizio Bonaccorsi, Guido Cerbai,Spartaco M. Colombani, Anna R. Renzetti, Rocco Cirillo, Alessandro Subissi,Giuliano Alagona. 4-Diazinyl- and 4-Pyridinylimidazoles: Potent Angiotensin II Antagonists. A Study of Their Activity and Computational Characterization.J. Med. Chem. 1995, 38(15), 2925.
18. Werner W. K. R. Mederski, Dieter Dorsch, Heinz-Hermann Bokel, Norbert Beier,Ingeborg Lues, Pierre Schelling.Non-Peptide Angiotensin II Receptor Antagonists: Synthesis and Biological Activity of a Series of Novel 4,5-Dihydro-4-oxo-3H-imidazo[4,5-c]pyridine Derivatives. J. Med. Chem. 1994, 37(11), 1632.
19. Alka Bali, Yogita Bansal, M. Sugumaran, Jatinder Singh Saggu, P. Balakumar, Gurpreet Kaur, Gulshan Bansal, Ajay Sharma, Manjeet Singh. Design, synthesis, and evaluation of novelly substituted benzimidazole compounds as angiotensin II receptor antagonists.Bioorganic & Medicinal Chemistry Letters, 2005,15, 3962.
20. Daljit S. Dhanoa, Scott W. Bagley, Raymond S. L. Chang, Victor J. Lotti, Tsing Bau Chen, Salah D. Kivlighn, Gloria J. Zingaro, Peter K. S. Siegl, Arthur A.Patchett, William J. Greenlee. Non-peptide angiotensin II receptor antagonists. 2.Design, synthesis, and biological activity of N-substituted (phenylamino) phenylacetic acids and acyl sulfonamides. J. Med. Chem. 1993, 36(26), 4239.
21. Cappelli, A.; Pericot Mohr, G.; Gallelli, A.; Rizzo, M.; Anzini, M.; Vomero, S.;Mennuni, L.; Ferrari, F.; Makovec, F.; Menziani, M. C.; De Benedetti, P. G.;Giorgi, G..
1.Srinivas,K.;Nair,C.K.Snehalatha;Ramesh,S.;Pardhasaradhi,M.A rapid and efficient synthesis of 2-butyl-5-chloro-3H-imidazole-4-carboxaldehyde.Synthesis,2004,4,506.
2.Griffiths,G.J.;Hauck,M.B.;ImwinkeLried,R.;Kohr,J.;Roten,C.A.;Stucky,G.C.;GosteLi,J.J.Org.Chem.,1999,64(22),8084.
3.ALdrich P.E.;Dunica J.V.;Pierce M.E.U.S.Patent.1989,4874867,.
4.晁淑军,惠新平,李硕,许鹏飞,张自义,王勤,王燕玲。含均三唑环的新型联苯四唑衍生物的合成及抗菌活性,化学学报2005,63(6),525.
5.IsmaiL,Mohamed A.H.;Barker,Stewart;Abou EL ELLa,DaLaL A.;Abouzid,KhaLed A.M.;Toubar,Rabab A.;Todd,Matthew H.Design and Synthesis of New TetrazoLyl-and Carboxy-biphenylylmethyl-quinazolin-4-one Derivatives as Angiotensin Ⅱ AT_1Receptor Antagonists.Journal of Medicinal Chemistry 2006,49(5),1526.
6.De,B.;Winn,M.;Zydowsky,T.M.;Kerkman,D.J.;DeBemardis,J.F.;Lee,J.;Buckner,S.;Warner,R.;Brune,M.Discovery of a novel class of orally active,non-peptide angiotensin Ⅱ antagonists.Journal of Medicinal Chemistry 1992,35(20),3714.
7.Basappa,B.H.Doreswamy;Mahendra,M.;ManteLingu,K.;Sridhar,M.A.;Prasad,J.Shashidhara;Rangappa,K.S.Reduction of aldehydes and oximes to their corresponding alcohols and amines by catalytic hydrogenation method.Indian Journal of Chemistry,Section B:Organic Chemistry Including Medicinal Chemistry 2005,44B(1),148.
8.Larsen,Robert D.;King,Anthony O.;Chen,Cheng Y.;Corley,Edward G.;Foster,Bruce S.;Roberts,F.Edward;Yang,Chunhua;Lieberman,David R.;Reamer,Robert A.Efficient Synthesis of Losartan,A Nonpeptide Angiotensin Ⅱ Receptor Antagonist.Journal of Organic Chemistry 1994,59(21),6391.
9.Fritz Voegtle;Norbert Eisen;Sybille Franken;Petra BueLLesbach;Heinrich Puff.Doubly clamped cope systems.Journal of Organic Chemistry 1987,52(25),5560.
10.Colin-Messager,Sandrine;Girard,Jean Pierre;Rossi,Jean Claude.Convenient method for the preparation of trityl ethers from secondary alcohols.Tetrahedron Letters 1992,33(19),2689.
11.Lu,Rong Jian;Liu,Daipei;Giese,Roger W.Detritylation with ytterbium triflate.Tetrahedron Letters 2000,41(16),2817-2819.
12.Larry R.Hillis;Robert C.RonaLd.Total synthesis of(-)-grahamimycin Al Journal of Organic Chemistry 1985,50(4),470.
13.John Mann;Alison Thomas.A novel approach to cis-chrysanthemic acids.Tetrahedron Letters 1986,27(30),3533.
14.Yuying C.Hwang;Frank W.Fowler.Diels-Alder reaction of 1-azadienes:A total synthesis of deoxynupharidine.Journal of Organic Chemistry,1985,50(15),2719.
15.Martin Newcomb;Michael T.Burchill;Thomas M.Deeb.A mechanistic probe study of potential electron-transfer reactions of Lithium dialkylamides.J.Am.Chem.Soc.,1988,110(19),6528.
16.Iwao Chujo;Yoshiaki Masuda;Kenji Fujino;Sachiko Kato;Takehiro Ogasa.Synthetic study on novel immunosuppressant KF20444.Bioorganic & Medicinal Chemistry 2001,9(12),3273.
17.Robert D.Larsen,Anthony O.King,Cheng Y.Chen,Edward G.Corley,Bruce S.Foster,F.Edward Roberts,Chunhua Yang,David R.Lieberman,Robert A.Reamer.Efficient Synthesis of Losartan,A Nonpeptide Angiotensin Ⅱ Receptor Antagonist.Journal of Organic Chemistry 1994,59(21),6391.
18.路军,葛红光,白银娟。无溶剂微波照射下2-取代苯并咪唑的合成,有机化学,2002,10,105。
19.Evan P.Kyba,Shiuh Tzung Liu,Kannappan ChockaLingam,B.Raghava Reddy.A general synthesis of substituted fluorenones and azafluorenones.Journal of Organic Chemistry 1988,53(15),3513.
20.James G.Smith,Peter W.Dibble,Richard E.Sandborn.The preparation and reactions of naphtha[1,2-c]furan and naphtho[2,3-c]furan.Journal of Organic Chemistry 1986,51(20),3762.
1.辛云霞。铜渣氯浸渣的回收利用,金川镍钻研究设计院。
2.张琦。硫物相分析测定方法的应用,黄金,2006,11,015。
3.李涛。热压氧化浸出有价金属过程中硫的物相分析,黄金,2006,11,013。
4.岩石矿物分析第一分册(第三版)地质出版社
5.北京矿冶研究总院,《化学物相分析》.冶金工业出版社,1979年。
6.金川有色金属公司技术标准Q/YSJC12-FX15.3-2000。
7.昆明冶金研究所,化学物相分析操作规程(二),1984年。
8.吴柏林。《冶金分析与测试》.《冶金分析分册》,1984年。
9.金川冶金过程中产品化学物相分析方法研究(二)。
10.鲁顺利。从高铁闪锌矿的高压酸浸渣中提取硫磺,昆明理工大学报1999,38(5),127。
11.张启卫,章永化。从软锰矿与黄铁矿硫酸浸出渣中回收硫磺的研究。1002-4336(2002)01-0008-03
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2.Sealey L.E.;Laragh J.H.Raven Press:New York,1990,1287.
3.戴生明,朱铨英,苏定冯。血管紧张素Ⅱ(angiotensinⅡ)受体的研究进展,药学实践杂志.1995,13(3),141。
4.1)John V.Duncia,Andrew T.Chiu,David J.Carini,George B.Gregory,Alexander L.Johnson,William A.Price,Gregory J.Wells,Pancras C.Wong,Joseph C.Calabrese,Pieter B.M.W.M.Timmermans.The discovery of potent nonpeptide angiotensin Ⅱ receptor antagonists:a new class of potent antihypertensives J.Med Chem.1990,33,1312;
2)王金东.洛沙坦和氟伐他汀在意大利获准。国外药讯,1995,8,25。
5.张玮,孙武,熊方武。国外上市新药。国外医药-合成药、生化药、制剂分册,1996,17(2),118。
6.Mealy N.;Castaner.Elisartan Potassium.Antihypertensive,Angiotensin Ⅱantagonist.J.Drugs Future,1996,21(2),139.
7.Hilditch A;Hunt A A;Travers A;Polley J;Drew G M;Middlemiss D;Judd D B;Ross B C;Robertson M.GR138950,a novel angiotensin AT1 receptor antagonist.J.Pharmacology,1993,108,239.
8.Kenakin T.The classification of drugs and drug receptors in isolated tissues.Pharmacology Rev.1984,36(3),165.
9.Robison K.A.;Robinson C.P.Saprisartan.Antihypertensive,Angiotensin Ⅱreceptor antagonist.J.Drugs Future,1996,21(11),1129.
10.Vans M.J.A.,Redemann N.Arznein-Forsch,1996,46(8),755.
11.Shibouta Y.;Inada Y.;Ojima M..Nonpeptide angiotensin Ⅱ-receptor antagonists.Yakuri to Chiryo,1996,24(10),2207.
12.Kito G.;Norimoto S.;Shiomi M.Arznein-Forsch,1996,46(1),572.
13.蒋巡天,华维一。非肽类血管紧张素Ⅱ受体拮抗剂的构效关系研究。药学进展,1995,19(3),145。
14.Nathan B.Mantlo,Prasun K.Chakravarty,Debra L.Ondeyka,Peter K.S.Siegl, Raymond S. Chang, Victor J. Lotti, Kristie A. Faust, Terry W. Schorn, Tsing Bau Chen. Potent, orally active imidazo[4,5-b]pyridine-based angiotensin II receptor antagonists. J. Med. Chem. 1991, 34(9), 2919.
15. Wong P.C., Christ D.D., Wong N. Nonpeptide angiotensin II receptor antagonist: pharmacokinetics and pharmacodynamics in rats of EXP3174, an active metabolite of losartan. Pharmacody-namics, 1996, 52(1), 25.
16. M. McIntyre,R. J. MacFadyen, P. A. Meredith, R. Brouard, J. L. Reid. Dose-Ranging Study of the Angiotensin II Receptor Antagonist Irbesartan (SR 47436/BMS-186295) on Blood Pressure and Neurohormonal Effects in Salt-Deplete Men. J. Cardiovascular Pharmacol, 1996, 28 (1), 101.
17. J. S. Harmat Nicholas, Raffaello Giorgi, Fabrizio Bonaccorsi, Guido Cerbai,Spartaco M. Colombani, Anna R. Renzetti, Rocco Cirillo, Alessandro Subissi,Giuliano Alagona. 4-Diazinyl- and 4-Pyridinylimidazoles: Potent Angiotensin II Antagonists. A Study of Their Activity and Computational Characterization.J. Med. Chem. 1995, 38(15), 2925.
18. Werner W. K. R. Mederski, Dieter Dorsch, Heinz-Hermann Bokel, Norbert Beier,Ingeborg Lues, Pierre Schelling.Non-Peptide Angiotensin II Receptor Antagonists: Synthesis and Biological Activity of a Series of Novel 4,5-Dihydro-4-oxo-3H-imidazo[4,5-c]pyridine Derivatives. J. Med. Chem. 1994, 37(11), 1632.
19. Alka Bali, Yogita Bansal, M. Sugumaran, Jatinder Singh Saggu, P. Balakumar, Gurpreet Kaur, Gulshan Bansal, Ajay Sharma, Manjeet Singh. Design, synthesis, and evaluation of novelly substituted benzimidazole compounds as angiotensin II receptor antagonists.Bioorganic & Medicinal Chemistry Letters, 2005,15, 3962.
20. Daljit S. Dhanoa, Scott W. Bagley, Raymond S. L. Chang, Victor J. Lotti, Tsing Bau Chen, Salah D. Kivlighn, Gloria J. Zingaro, Peter K. S. Siegl, Arthur A.Patchett, William J. Greenlee. Non-peptide angiotensin II receptor antagonists. 2.Design, synthesis, and biological activity of N-substituted (phenylamino) phenylacetic acids and acyl sulfonamides. J. Med. Chem. 1993, 36(26), 4239.
21. Cappelli, A.; Pericot Mohr, G.; Gallelli, A.; Rizzo, M.; Anzini, M.; Vomero, S.;Mennuni, L.; Ferrari, F.; Makovec, F.; Menziani, M. C.; De Benedetti, P. G.;Giorgi, G..
1.Srinivas,K.;Nair,C.K.Snehalatha;Ramesh,S.;Pardhasaradhi,M.A rapid and efficient synthesis of 2-butyl-5-chloro-3H-imidazole-4-carboxaldehyde.Synthesis,2004,4,506.
2.Griffiths,G.J.;Hauck,M.B.;ImwinkeLried,R.;Kohr,J.;Roten,C.A.;Stucky,G.C.;GosteLi,J.J.Org.Chem.,1999,64(22),8084.
3.ALdrich P.E.;Dunica J.V.;Pierce M.E.U.S.Patent.1989,4874867,.
4.晁淑军,惠新平,李硕,许鹏飞,张自义,王勤,王燕玲。含均三唑环的新型联苯四唑衍生物的合成及抗菌活性,化学学报2005,63(6),525.
5.IsmaiL,Mohamed A.H.;Barker,Stewart;Abou EL ELLa,DaLaL A.;Abouzid,KhaLed A.M.;Toubar,Rabab A.;Todd,Matthew H.Design and Synthesis of New TetrazoLyl-and Carboxy-biphenylylmethyl-quinazolin-4-one Derivatives as Angiotensin Ⅱ AT_1Receptor Antagonists.Journal of Medicinal Chemistry 2006,49(5),1526.
6.De,B.;Winn,M.;Zydowsky,T.M.;Kerkman,D.J.;DeBemardis,J.F.;Lee,J.;Buckner,S.;Warner,R.;Brune,M.Discovery of a novel class of orally active,non-peptide angiotensin Ⅱ antagonists.Journal of Medicinal Chemistry 1992,35(20),3714.
7.Basappa,B.H.Doreswamy;Mahendra,M.;ManteLingu,K.;Sridhar,M.A.;Prasad,J.Shashidhara;Rangappa,K.S.Reduction of aldehydes and oximes to their corresponding alcohols and amines by catalytic hydrogenation method.Indian Journal of Chemistry,Section B:Organic Chemistry Including Medicinal Chemistry 2005,44B(1),148.
8.Larsen,Robert D.;King,Anthony O.;Chen,Cheng Y.;Corley,Edward G.;Foster,Bruce S.;Roberts,F.Edward;Yang,Chunhua;Lieberman,David R.;Reamer,Robert A.Efficient Synthesis of Losartan,A Nonpeptide Angiotensin Ⅱ Receptor Antagonist.Journal of Organic Chemistry 1994,59(21),6391.
9.Fritz Voegtle;Norbert Eisen;Sybille Franken;Petra BueLLesbach;Heinrich Puff.Doubly clamped cope systems.Journal of Organic Chemistry 1987,52(25),5560.
10.Colin-Messager,Sandrine;Girard,Jean Pierre;Rossi,Jean Claude.Convenient method for the preparation of trityl ethers from secondary alcohols.Tetrahedron Letters 1992,33(19),2689.
11.Lu,Rong Jian;Liu,Daipei;Giese,Roger W.Detritylation with ytterbium triflate.Tetrahedron Letters 2000,41(16),2817-2819.
12.Larry R.Hillis;Robert C.RonaLd.Total synthesis of(-)-grahamimycin Al Journal of Organic Chemistry 1985,50(4),470.
13.John Mann;Alison Thomas.A novel approach to cis-chrysanthemic acids.Tetrahedron Letters 1986,27(30),3533.
14.Yuying C.Hwang;Frank W.Fowler.Diels-Alder reaction of 1-azadienes:A total synthesis of deoxynupharidine.Journal of Organic Chemistry,1985,50(15),2719.
15.Martin Newcomb;Michael T.Burchill;Thomas M.Deeb.A mechanistic probe study of potential electron-transfer reactions of Lithium dialkylamides.J.Am.Chem.Soc.,1988,110(19),6528.
16.Iwao Chujo;Yoshiaki Masuda;Kenji Fujino;Sachiko Kato;Takehiro Ogasa.Synthetic study on novel immunosuppressant KF20444.Bioorganic & Medicinal Chemistry 2001,9(12),3273.
17.Robert D.Larsen,Anthony O.King,Cheng Y.Chen,Edward G.Corley,Bruce S.Foster,F.Edward Roberts,Chunhua Yang,David R.Lieberman,Robert A.Reamer.Efficient Synthesis of Losartan,A Nonpeptide Angiotensin Ⅱ Receptor Antagonist.Journal of Organic Chemistry 1994,59(21),6391.
18.路军,葛红光,白银娟。无溶剂微波照射下2-取代苯并咪唑的合成,有机化学,2002,10,105。
19.Evan P.Kyba,Shiuh Tzung Liu,Kannappan ChockaLingam,B.Raghava Reddy.A general synthesis of substituted fluorenones and azafluorenones.Journal of Organic Chemistry 1988,53(15),3513.
20.James G.Smith,Peter W.Dibble,Richard E.Sandborn.The preparation and reactions of naphtha[1,2-c]furan and naphtho[2,3-c]furan.Journal of Organic Chemistry 1986,51(20),3762.
1.辛云霞。铜渣氯浸渣的回收利用,金川镍钻研究设计院。
2.张琦。硫物相分析测定方法的应用,黄金,2006,11,015。
3.李涛。热压氧化浸出有价金属过程中硫的物相分析,黄金,2006,11,013。
4.岩石矿物分析第一分册(第三版)地质出版社
5.北京矿冶研究总院,《化学物相分析》.冶金工业出版社,1979年。
6.金川有色金属公司技术标准Q/YSJC12-FX15.3-2000。
7.昆明冶金研究所,化学物相分析操作规程(二),1984年。
8.吴柏林。《冶金分析与测试》.《冶金分析分册》,1984年。
9.金川冶金过程中产品化学物相分析方法研究(二)。
10.鲁顺利。从高铁闪锌矿的高压酸浸渣中提取硫磺,昆明理工大学报1999,38(5),127。
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