CN110280393A - A kind of isopropyl xanthan acid propynyl ester and preparation method thereof - Google Patents

A kind of isopropyl xanthan acid propynyl ester and preparation method thereof Download PDF

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Publication number
CN110280393A
CN110280393A CN201910494300.2A CN201910494300A CN110280393A CN 110280393 A CN110280393 A CN 110280393A CN 201910494300 A CN201910494300 A CN 201910494300A CN 110280393 A CN110280393 A CN 110280393A
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CN
China
Prior art keywords
isopropyl
propynyl ester
added
preparation
xanthan acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201910494300.2A
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Chinese (zh)
Inventor
张海龙
王咏梅
牟松
郭靖宇
王国刚
赵春艳
范志鸿
肖文革
赵越峰
关蕴
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Shenyang You Yan Mineral Chemical Co Ltd
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Shenyang You Yan Mineral Chemical Co Ltd
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Priority to CN201910494300.2A priority Critical patent/CN110280393A/en
Publication of CN110280393A publication Critical patent/CN110280393A/en
Pending legal-status Critical Current

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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B03SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03DFLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D1/00Flotation
    • B03D1/001Flotation agents
    • B03D1/004Organic compounds
    • B03D1/012Organic compounds containing sulfur
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C07C329/12Dithiocarbonic acids; Derivatives thereof
    • C07C329/14Esters of dithiocarbonic acids
    • C07C329/16Esters of dithiocarbonic acids having sulfur atoms of dithiocarbonic groups bound to acyclic carbon atoms
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B03SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03DFLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D2201/00Specified effects produced by the flotation agents
    • B03D2201/02Collectors
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B03SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03DFLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D2203/00Specified materials treated by the flotation agents; specified applications
    • B03D2203/02Ores
    • B03D2203/025Precious metal ores

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

It is specifically a kind of for the copper mine containing noble metals such as gold, silver and copper-molybdenum and the esters flotation reagent of other metalliferous minerals and preparation method thereof the present invention relates to isopropyl xanthan acid propynyl ester and preparation method thereof, there is following chemical structural formula:

Description

A kind of isopropyl xanthan acid propynyl ester and preparation method thereof
Technical field
The present invention relates to isopropyl xanthan acid propynyl ester and preparation method thereof, specifically a kind of isopropyl xanthan acid third Alkynes ester and preparation method thereof.
China's copper resource rich reserves, the 8% of Zhan Quanqiu reserves, but Large-scale Copper only accounts for 3%, and remaining is all middle-size and small-size mine Bed, and China's copper resource rich ore is few, lean ore and complicated difficult select smelting mine more;It is utilized especially as the large scale mining of copper resource, easily The copper ore resource of choosing is fewer and fewer;The copper resource development and utilization of complicated difficult choosing have become inexorable trend, low-grade, microfine, difficulty Selecting sulphide ore will be one of China's copper resource important sources;The also association of China's copper ore resource gold, silver abundant, molybdenum, sulphur etc. have Beneficial element and its mineral;Therefore, poor, thin, composition brass ore resources are researched and developed and sorts technology, it is beneficial to improve gold, silver, molybdenum, sulphur of association etc. The rate of recovery of element reinforces the comprehensive utilization ratio of copper ore resource, not only can create considerable economic benefit for bargh, The dependency degree to import copper resource can be reduced, is of great significance to the sustainable development for ensureing China's Copper Processing Industry.
Summary of the invention
In view of the above problems, the present invention provides a kind of isopropyl xanthan acid propynyl ester and preparation method thereof.
Isopropyl xanthan acid propynyl ester of the invention and preparation method thereof is characterized by with following chemical structural formula:
Isopropyl xanthan acid propynyl ester preparation method, comprising the following specific steps
Prepare isopropyl xanthan acid propynyl ester
Reaction kettle is added in the water of 2.5 times of sodium isopropyl xanthate amounts, starts agitating paddle, investment sodium isopropyl xanthate carries out molten Solution;
Hydrochloric acid is added into the complete solution of dissolution again, carries out neutralization reaction;
When pH value of solution=6.5~8, stop that hydrochloric acid is added, then by propargyl chloride be added in and good solution in, the chlorine of addition Propine and sodium isopropyl xanthate molar ratio are (0.95~1.05): 1, temperature T=30~60 DEG C are kept, 2~4h is kept the temperature;Reaction After, stratification obtains final products isopropyl xanthan acid propynyl ester.
Compared with prior art, beneficial effects of the present invention:
The isopropyl xanthan acid propynyl ester that the present invention provides, product content >=88%, conversion ratio >=85%.At present both at home and abroad not yet The research unit or manufacturer of such product are developed, raw material are nontoxic, and equipment investment is few, and simple production process is pollution-free, do not have There is waste generation, production cost is low;With a variety of substances with above structure prepared by the present invention, it is real to be applied to small-sized open circuit It tests and situ industrialization is tested;For, containing gold, the metalliferous mineral of the noble metals such as silver can increase substantially copper mine and expensive in copper mine The rate of recovery of metal.The collecting agent is also applied for copper-molybdenum and other metalliferous minerals simultaneously, has preferably to metal recovery rate is improved Effect, remarkable economic and social benefits.
Specific embodiment
1 isopropyl xanthan acid propynyl ester of embodiment
470 kilograms of clean waters are put into the enamel stirred tank of jacketed, start stirring, put into sodium isopropyl xanthate 188 It kilogram is dissolved;After completely dissolution to sodium isopropyl xanthate, hydrochloric acid is added dropwise, is adjusted to pH=6.5.Then 71.5 kilograms are added Propargyl chloride, temperature T=30 DEG C in reaction process keep the temperature 2h;Reaction terminates, and standing is layered for 24 hours, and organic phase is isopropyl xanthan Sour propynyl ester;The yield of isopropyl xanthan acid propynyl ester is 85.47% under such process conditions, content 88.36%;(this yield It is the average value of many experiments with content)
Every kind of ore all carries out repeating experiment and then takes its average value to each collecting agent and additive amount;Isopropyl xanthan acid propynyl ester It see the table below compared with isopropoxyethyl radicals thiourethane aeneficiation effect:
Collecting agent Dosage g/t Raw ore copper grade, % Cu Concentrate Grade, % Copper recovery, %
Isopropoxyethyl radicals thiourethane 10 1.12 20.63 92.02
Isopropyl xanthan acid propynyl ester 10 1.12 20.38 92.57
2 isopropyl xanthan acid propynyl ester of embodiment
470 kilograms of clean waters are put into the enamel stirred tank of jacketed, start stirring, put into sodium isopropyl xanthate 188 It kilogram is dissolved;After completely dissolution to sodium isopropyl xanthate, hydrochloric acid is added dropwise, is adjusted to pH=7.5;Then 75 kilograms of chlorine are added Propine, temperature T=45 DEG C in reaction process keep the temperature 2.5h;Reaction terminates, and standing is layered for 24 hours, and organic phase is isopropyl xanthan Sour propynyl ester;The yield of isopropyl xanthan acid propynyl ester is 86.41% under such process conditions, content 88.02%;(this yield It is the average value of many experiments with content)
Every kind of ore all to each collecting agent and and additive amount carry out repeating experiment and then take its average value;Isopropyl xanthan acid propine Ester see the table below compared with isopropoxyethyl radicals thiourethane aeneficiation effect:
Collecting agent Dosage g/t Raw ore copper grade, % Cu Concentrate Grade, % Copper recovery, %
Isopropoxyethyl radicals thiourethane 10 1.12 20.63 92.02
Isopropyl xanthan acid propynyl ester 10 1.12 21.17 93.13
3 isopropyl xanthan acid propynyl ester of embodiment
470 kilograms of clean waters are put into the enamel stirred tank of jacketed, start stirring, put into sodium isopropyl xanthate 188 It kilogram is dissolved;After completely dissolution to sodium isopropyl xanthate, hydrochloric acid is added dropwise, is adjusted to pH=8;Then 79 kilograms of chlorine third are added Alkynes, temperature T=60 DEG C in reaction process keep the temperature 4h;Reaction terminates, and standing is layered for 24 hours, and organic phase is isopropyl xanthan acid third Alkynes ester;The yield of isopropyl xanthan acid propynyl ester is 85.36% under such process conditions, content 88.79%;(this yield and contain Amount is the average value of many experiments)
Every kind of ore all to each collecting agent and and additive amount carry out repeating experiment and then take its average value;Isopropyl xanthan acid propine Ester see the table below compared with isopropoxyethyl radicals thiourethane aeneficiation effect:
Collecting agent Dosage g/t Raw ore copper grade, % Cu Concentrate Grade, % Copper recovery, %
Isopropoxyethyl radicals thiourethane 10 1.12 20.63 92.02
Isopropyl xanthan acid propynyl ester 10 1.12 20.56 92.88
4 isopropyl xanthan acid propynyl ester of embodiment
470 kilograms of clean waters are put into the enamel stirred tank of jacketed, start stirring, put into sodium isopropyl xanthate 188 It kilogram is dissolved.After completely dissolution to sodium isopropyl xanthate, hydrochloric acid is added dropwise, is adjusted to pH=6.5;Then 79 kilograms of chlorine are added Propine, temperature T=35 DEG C in reaction process keep the temperature 2.5h;Reaction terminates, and standing is layered for 24 hours, and organic phase is isopropyl xanthan Sour propynyl ester;The yield of isopropyl xanthan acid propynyl ester is 85.81% under such process conditions, content 89.07%;(this yield It is the average value of many experiments with content)
Every kind of ore all to each collecting agent and and additive amount carry out repeating experiment and then take its average value;The isopropyl of phase homogenous quantities Xanthic acid propynyl ester see the table below compared with aerofloat 226 aeneficiation effect:
5 isopropyl xanthan acid propynyl ester of embodiment
470 kilograms of clean waters are put into the enamel stirred tank of jacketed, start stirring, put into sodium isopropyl xanthate 188 It kilogram is dissolved.After completely dissolution to sodium isopropyl xanthate, hydrochloric acid is added dropwise, is adjusted to pH=8;Then 72 kilograms of chlorine third are added Alkynes, temperature T=55 DEG C in reaction process keep the temperature 3h;Reaction terminates, and standing is layered for 24 hours, and organic phase is isopropyl xanthan acid third Alkynes ester;The yield of isopropyl xanthan acid propynyl ester is 85.42% under such process conditions, content 88.63%;(this yield and contain Amount is the average value of many experiments)
Every kind of ore all to each collecting agent and and additive amount carry out repeating experiment and then take its average value.Isopropyl xanthan acid propine Ester see the table below compared with isopropoxyethyl radicals thiourethane aeneficiation effect:
Chilean Copper Ores

Claims (1)

1. a kind of isopropyl xanthan acid propynyl ester and preparation method thereof, it is characterised in that have following chemical structural formula:
Isopropyl xanthan acid propynyl ester preparation method, comprising the following specific steps
Prepare isopropyl xanthan acid propynyl ester
Reaction kettle is added in the water of 2.5 times of sodium isopropyl xanthate amounts, starts agitating paddle, investment sodium isopropyl xanthate carries out molten Solution;
Hydrochloric acid is added into the complete solution of dissolution again, carries out neutralization reaction;
When pH value of solution=6.5~8, stop that hydrochloric acid is added, then by propargyl chloride be added in and good solution in, the chlorine of addition Propine and sodium isopropyl xanthate molar ratio are (0.95~1.05): 1, temperature T=30~60 DEG C are kept, 2~4h is kept the temperature;Reaction After, stratification obtains final products isopropyl xanthan acid propynyl ester.
CN201910494300.2A 2019-06-09 2019-06-09 A kind of isopropyl xanthan acid propynyl ester and preparation method thereof Pending CN110280393A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN86101646A (en) * 1985-07-12 1987-01-07 陶氏化学公司 The new collector composition that is used for froth flotation method
CN101992151A (en) * 2010-11-11 2011-03-30 西北矿冶研究院 High-sulfur copper ore collecting agent
CN102702055A (en) * 2012-05-30 2012-10-03 西北矿冶研究院 Dialkyl amido amine methyl xanthate compound and synthetic method thereof
WO2016024240A1 (en) * 2014-08-12 2016-02-18 Stellenbosch University Conjugate for treating malaria
CN106432022A (en) * 2015-08-06 2017-02-22 北京天任瑞创科技发展有限公司 Preparation method for alkyl xanthate allyl ester compound

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN86101646A (en) * 1985-07-12 1987-01-07 陶氏化学公司 The new collector composition that is used for froth flotation method
CN101992151A (en) * 2010-11-11 2011-03-30 西北矿冶研究院 High-sulfur copper ore collecting agent
CN102702055A (en) * 2012-05-30 2012-10-03 西北矿冶研究院 Dialkyl amido amine methyl xanthate compound and synthetic method thereof
WO2016024240A1 (en) * 2014-08-12 2016-02-18 Stellenbosch University Conjugate for treating malaria
CN106432022A (en) * 2015-08-06 2017-02-22 北京天任瑞创科技发展有限公司 Preparation method for alkyl xanthate allyl ester compound

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ALIEV, M. I. 等: "Synthesis of some xanthates", 《ZHURNAL OBSHCHEI KHIMII》 *
牟松等: "一种烷基黄原酸酯类药剂的合成研究 ", 《有色矿冶》 *

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