CN101066941A - Prepn process of ferric alkyl aryl sulfonate - Google Patents
Prepn process of ferric alkyl aryl sulfonate Download PDFInfo
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Abstract
The preparation process of ferric alkyl aryl sulfonate includes the following steps: reflux reaction between anhydrous ferric trichloride or ferric trichloride hexahydrate and alkyl aryl sulfonic acid in alcohol solution, eliminating solvent and hydrogen chloride gas at high temperature and low pressure to produce coarse product; washing with ethyl ether to eliminate excessive p-toluene sulfonic acid, and re-crystallizing in mixed solvent of methanol and acetonitrile to obtain purified ferric alkyl aryl sulfonate. The present invention provides also one other process for preparing ferric long chain (benzene) sulfonate. The present invention has low material cost and high product purity, and the product is used in electronic industry.
Description
Technical field
The present invention is the synthetic and method of purification of a kind of electronics rank ferric alkyl aryl sulfonate and solution thereof.
Background technology
Ferric alkyl aryl sulfonate has purposes very widely as catalyzer and oxygenant commonly used in a kind of organic synthesis.Compare with inorganic molysite,, be widely used in the organic reaction process thereby can be used as catalyzer, oxygenant or reaction raw materials because the relatively large lipophilicity negatively charged ion of its volume makes it all have good solubility in most organic solvents.Because the oxidizing potential that it is suitable, possesses good doping function simultaneously with the negatively charged ion that discharges after its reduction, so it is synthetic to be well suited for being used for the oxidation of PEDOT, PPY and PAN type conducting polymer, generate conductive polymers by its oxypolymerization and not only have excellent electric conductivity, and owing to mix to ionic volume steric hindrance, it possesses satisfactory stability under air medium and high temperature condition, so the class conducting polymer after coming out, just is widely used rapidly.Its Application Areas relates to: fields such as organic synthesis, electrolytic condenser, OLED, anti-static coating, organic semiconductor.
In the patent documentation [US4910645, US5812367, US6206937, US6556427, US6798664, US7087292] with it as oxygenant and 3,4-enedioxy thiophene reaction in prepares PEDOT type spirally wound solid electrolyte capacitor.Adopt the monomer and the oxygenant of proper ratio to mix,, under certain temperature sequence, carry out in-situ polymerization, form actual negative electrode with high conductivity electrical condenser to flood through charing, the capacitor body that changes into processing.Because the oxidizing potential of tosic acid iron is close with the oxidizing potential of EDOT, polymerization rate is moderate, makes steeping process to carry out smoothly, so existing large-scale application is in conductive polymers chemical capacitor field.
Patent documentation [US5,766,515, US 5,965,281, US 6,050,677, and US 6,083,635, US 6,136, and 372, US 6,515,417, and US 6,498,918, US 6,483, and 099, the 4-enedioxy thiophene numerous areas such as being applied to anti-static coating, OLED, printed circuit board (PCB) that combines is also arranged US 6,201,051] it as oxygenant and doping agent and 3.
Except that being used for chemical reaction, because its Application Areas relates to the electronic devices and components industry more, so the characteristics such as solids content of its purity, water content, outward appearance and viscosity and product are had particular requirement as catalyzer and the oxygenant.
Such as chlorion and sulfate ion to a lot of metals extremely oxide film the intensive corrosive nature is arranged, can destruction be arranged to the base material of conducting polymer, in particular for the reagent of electrical condenser, need strict these two kinds of ionic content of control.
And micro-water content is very big to the specific conductivity and the stability influence of the polymkeric substance that generated.The existence of less water makes the polymer conductivity that is generated reduce, and stability is also relatively poor, when being applied to solid electric capacity, showing as impedance and loss and becomes big, the lost of life of product.
Summary of the invention
The objective of the invention is has the ferric alkyl aryl sulfonate product of particular requirement in order to obtain to satisfy electron trade etc. by a series of methods of purification.
The preparation method of ferric alkyl aryl sulfonate of the present invention comprises following steps:
1) FERRIC CHLORIDE ANHYDROUS or Iron(III) chloride hexahydrate and alkyl aryl sulfonate are according to mol ratio (1: 2～1: 4) back flow reaction in ethanolic soln;
2) under temperature is 120 ℃～180 ℃ condition, remove solvent and hydrogen chloride gas then, generate the crude product of ferric alkyl aryl sulfonate;
3) wash crude product with ether, remove unnecessary alkyl aryl sulfonate;
4) mixed solvent with methyl alcohol and acetonitrile carries out the recrystallization purification to crude product, obtains the finished product of ferric alkyl aryl sulfonate.
The present invention is also in described step 2) and 3) between in steps 2 ') crude product is dissolved in the dehydrated alcohol again, add an amount of reactive reagent, remove the chlorion and the sulfate ion of trace, filter the elimination insolubles after, slough solvent.
Positively charged ion in the reactive reagent of the present invention is silver ions and barium ion, and negatively charged ion is at least a in tosic acid root, Phenylsulfonic acid root, alkyl aryl sulfonate root, nitrate radical or the hydroxide radical.
And the add-on of response type reagent is to be as the criterion with the measured detrimental impurity ionic amount of chromatography of ions, waits mole or excessive a little adding.
After after described step 4), also having the ferric alkyl aryl sulfonate process vacuum-drying of step 5), be dissolved in the alcoholic solvent, obtain the solution of ferric alkyl aryl sulfonate the recrystallization purification.
Described alcoholic solvent is at least a in ethanol, Virahol, the butanols.
The volume ratio of methyl alcohol and acetonitrile is 1: 5 in the described mixed solvent.
The preparation method of chain alkyl aromatic sulphonic acid iron of the present invention comprises following steps:
A) FERRIC CHLORIDE ANHYDROUS or Iron(III) chloride hexahydrate and chain alkyl aromatic azochlorosulfonate acid sodium react in water according to mol ratio (1: 2～1: 4);
B) filter the product of separating out in the water outlet, clean the back oven dry, make the crude product of chain alkyl aromatic sulphonic acid iron;
C) mixed solvent with methyl alcohol and acetonitrile carries out the recrystallization purification to crude product, obtains the finished product of chain alkyl aromatic sulphonic acid iron.
At described step b) and c) between b ' in steps) crude product is dissolved in the dehydrated alcohol again, add an amount of reactive reagent, remove the chlorion and the sulfate ion of trace, filter the elimination insolubles after, slough solvent.
Positively charged ion in the reactive reagent is silver ions and barium ion, and negatively charged ion is at least a in tosic acid root, Phenylsulfonic acid root, alkyl aryl sulfonate root, nitrate radical or the hydroxide radical.
The add-on of response type reagent is to be as the criterion with the measured detrimental impurity ionic amount of chromatography of ions, waits mole or excessive a little adding.
After after described step c), also having the chain alkyl aromatic sulphonic acid iron process vacuum-drying of step d), be dissolved in the alcoholic solvent, obtain the solution of chain alkyl aromatic sulphonic acid iron the recrystallization purification.
Described alcoholic solvent is at least a in ethanol, Virahol, the butanols.
The volume ratio of methyl alcohol and acetonitrile is 1: 5 in the described mixed solvent.
The present invention is with lower material cost, acquisition can be satisfied the ferric alkyl aryl sulfonate product that electron trade etc. has particular requirement, can effectively control purity, water content, outward appearance and the viscosity of ferric alkyl aryl sulfonate product and the characteristics such as solids content of product.
The present invention adopts vacuum-drying and is that the mode of band aqua component distillation combines with the propyl carbinol, and the moisture content that can control the finished product is below 1%.
The present invention carries out coarse filtration by centrifuging to reaction solution, and then by tubulose polypropylene microfiltration membrane, and throw out that can the filtering trace obtains good vitreous state.
The present invention is dissolved in the ferric alkyl aryl sulfonate product in the alcoholic solvents such as ethanol, Virahol, butanols, and identical containing admittedly down, the viscosity of ethanolic soln is minimum, butanols the highest.Consider in the use, may exist decompression operation down, when reducing viscosity, need to control the saturated vapor pressure of solution again.So the alcoholic solvent by several different viscositys, different boiling mixes, and the ferric alkyl aryl sulfonate product is dissolved in the mixed solvent of gained.
Embodiment
Below in conjunction with specific embodiment the present invention is described in further details.
Embodiment one,
Place a three-necked flask of 1 liter that reflux exchanger is housed with a hydration tosic acid of 1 mole Iron(III) chloride hexahydrate and 3 moles, add 250 milliliters of dehydrated alcohols, reflux half an hour, again under vacuum decompression, remove the second alcohol and water fully, take off most solvent after, be warming up to 160 ℃, keeping vacuum tightness is following 3 hours of 2KPa, the crude product russet that is dewatered fully.Again be dissolved in crude product in the dehydrated alcohol, add an amount of reactive reagent, remove the chlorion and the sulfate ion of trace, after filtering the elimination insolubles, slough solvent, removing the free tosic acid three times with ether washing, is that the mixed solvent of 1: 5 (v/v) carries out recrystallization to it and obtains good orange crystal with methyl alcohol and acetonitrile again.
The orange crystal of gained is as in the vacuum drying oven, and keeping vacuum tightness is under the 100Pa, 70 ℃ 20 hours.To be dissolved in the excessive propyl carbinol through vacuum drying product, and obtain transparent butanol solution, underpressure distillation is concentrated into that to contain admittedly be 65%, and in the vacuum distillation process, butanols can be further and the minor amount of water azeotropic, and it is taken out of.Add dehydrated alcohol again and regulate its concentration to 50%, measuring its viscosity is 80mPas.Detecting moisture content with Ka Er-Fei Xiu micro-moisture titration apparatus is 0.8%, below the content 3PPM by chromatography of ions chlorine detection ion and sulfate ion.
Embodiment two,
Place a three-necked flask of 1 liter that reflux exchanger is housed with a hydration tosic acid of 1 mole FERRIC CHLORIDE ANHYDROUS and 3 moles, add 250 milliliters of dehydrated alcohols, reflux half an hour, again under vacuum decompression, remove the second alcohol and water fully, take off most solvent after, be warming up to 180 ℃, keeping vacuum tightness is following 3 hours of 2KPa, obtains crude product russet.Again be dissolved in crude product in the dehydrated alcohol, add an amount of reactive reagent, the chlorion of place to go trace and sulfate ion, after filtering the elimination insolubles, slough solvent, remove unnecessary tosic acid three times with ether washing, with the mixed solvent of methyl alcohol and acetonitrile it is carried out recrystallization again and obtain good orange crystal.
The orange crystal of gained is as in the vacuum drying oven, 70 ℃ 20 hours.It is dissolved in the excessive propyl carbinol, obtains transparent butanol solution, be evaporated to that to contain admittedly be 65%, add dehydrated alcohol again and regulate concentration to 55%, measuring its viscosity is 100mPas.Detect moisture content 0.9% with Ka Er-Fei Xiu micro-moisture titration apparatus, below the content 3PPM by chromatography of ions chlorine detection ion and sulfate ion.。
Embodiment three,
Place a three-necked flask of 1 liter that reflux exchanger is housed with a hydration tosic acid of 1 mole FERRIC CHLORIDE ANHYDROUS and 2 moles, add 250 milliliters of dehydrated alcohols, reflux half an hour, again under vacuum decompression, remove the second alcohol and water fully, take off most solvent after, be warming up to 120 ℃, keeping vacuum tightness is following 3 hours of 2KPa, obtains crude product russet.Again be dissolved in crude product in the dehydrated alcohol, add an amount of reactive reagent, the chlorion of place to go trace and sulfate ion, after filtering the elimination insolubles, slough solvent, remove unnecessary tosic acid three times with ether washing, with the mixed solvent of methyl alcohol and acetonitrile it is carried out recrystallization again and obtain good orange crystal.
The orange crystal of gained is as in the vacuum drying oven, 70 ℃ 20 hours.It is dissolved in the excessive dehydrated alcohol, is evaporated to that to contain admittedly be 55%.Detect moisture content 1.2% with Ka Er-Fei Xiu micro-moisture titration apparatus.
Embodiment four,
Hydration tosic acid with 1 mole Iron(III) chloride hexahydrate and 4 moles reacts, and the reactions steps of present embodiment is identical with embodiment one.
Iron(III) chloride hexahydrate and FERRIC CHLORIDE ANHYDROUS can be exchanged among above-mentioned four embodiment.
Embodiment five,
Sodium dodecylbenzene sulfonate with 1 mole FERRIC CHLORIDE ANHYDROUS and 3 moles places 1 liter three-necked flask, adds 700 ml waters, and stirring reaction 48 hours does not observe the Sodium dodecylbenzene sulfonate particle of white in reaction system.With the reaction solution decompress filter, obtain the xanchromatic filter cake, wash repeatedly with clear water.After the filter cake vacuum-drying with gained, again be dissolved in the dehydrated alcohol, add an amount of reactive reagent, remove the chlorion and the sulfate ion of trace, after filtering the elimination insolubles, sloughing solvent, is that the mixed solvent of 1: 5 (v/v) carries out recrystallization to it and obtains good orange crystal with methyl alcohol and acetonitrile.
The orange crystal of gained is as in the vacuum drying oven, and keeping vacuum tightness is under the 100Pa, and 70 ℃ following 20 hours.Product after vacuum-drying is dissolved in the excessive propyl carbinol, obtains transparent butanol solution, be evaporated to that to contain admittedly be 65%, add butanols again and regulate concentration to 55%, measuring its viscosity is 125mPas.Detect moisture content 0.7% with Ka Er-Fei Xiu micro-moisture titration apparatus.
Embodiment six
Sodium dodecylbenzene sulfonate with 1 mole Iron(III) chloride hexahydrate and 4 moles places 1 liter three-necked flask, adds 700 ml waters and reacts.Other steps are identical with embodiment five.
Embodiment seven
With the Sodium dodecylbenzene sulfonate in the dinonylnaphthalene sulfonic acid sodium alternate embodiment five, participate in reaction by 1 mole of FERRIC CHLORIDE ANHYDROUS and 2 moles of dinonylnaphthalene sulfonic acid sodium, other steps are identical with embodiment five.
Embodiment eight,
Substitute tosic acid with dibutyl naphthalene sulfonic acid, all the other steps and embodiment are together.It is 55% butanol solution that the product of gained is joined, and measuring its viscosity is 120mPas.Detecting moisture content with Ka Er-Fei Xiu micro-moisture titration apparatus is 0.6%, below the content 3PPM by chromatography of ions chlorine detection ion and sulfate ion.
Embodiment nine,
Place a three-necked flask of 1 liter that reflux exchanger is housed with the Witco 1298 Soft Acid of 1 mole Iron(III) chloride hexahydrate and 4 moles, add 250 milliliters of dehydrated alcohols, reflux half an hour, again under vacuum decompression, remove the second alcohol and water fully, take off most solvent after, be warming up to 160 ℃, keeping vacuum tightness is following 3 hours of 2KPa, the thick material of the xanchromatic that is dewatered fully.Crude product is dissolved in the dehydrated alcohol again, adds an amount of reactive reagent, remove the chlorion and the sulfate ion of trace, after filtering the elimination insolubles, sloughing solvent, with ether washing, is that the mixed solvent of 1: 5 (v/v) carries out recrystallization to it with methyl alcohol and acetonitrile again.
The orange crystal of gained is as in the vacuum drying oven, and keeping vacuum tightness is under the 100Pa, 70 ℃ 20 hours.To be dissolved in the excessive propyl carbinol through vacuum drying product, obtain transparent butanol solution, be evaporated to that to contain admittedly be 65%, and add butanols again and regulate its concentration to 55%,, measuring its viscosity is 125mPas.Detecting moisture content with Ka Er-Fei Xiu micro-moisture titration apparatus is 0.8%, below the content 3PPM by chromatography of ions chlorine detection ion and sulfate ion.
Embodiment ten,
Witco 1298 Soft Acid with 1 mole FERRIC CHLORIDE ANHYDROUS and 2 moles reacts, and the reactions steps of present embodiment is identical with embodiment nine.
Positively charged ion in the reactive reagent in the foregoing description is silver ions and barium ion, and negatively charged ion is at least a in tosic acid root, Phenylsulfonic acid root, alkyl aryl sulfonate root, nitrate radical or the hydroxide radical.The add-on of response type reagent is to be as the criterion with the measured detrimental impurity ionic amount of chromatography of ions, waits mole or excessive a little adding.
Above-mentioned ethanol as alcoholic solvent, butanols also can be replaced by Virahol.
Claims (10)
1, a kind of preparation method of ferric alkyl aryl sulfonate is characterized in that, comprises following steps:
1) FERRIC CHLORIDE ANHYDROUS or Iron(III) chloride hexahydrate and alkyl aryl sulfonate are according to mol ratio (1: 2～1: 4) back flow reaction in ethanolic soln;
2) under temperature is 120 ℃～180 ℃ condition, remove solvent and hydrogen chloride gas then, generate the crude product of ferric alkyl aryl sulfonate;
3) wash crude product with ether, remove unnecessary alkyl aryl sulfonate;
4) mixed solvent with methyl alcohol and acetonitrile carries out the recrystallization purification to crude product, obtains the finished product of ferric alkyl aryl sulfonate.
2, the preparation method of a kind of ferric alkyl aryl sulfonate according to claim 1, it is characterized in that, in described step 2) and 3) between in steps 2 ') be dissolved in crude product in the dehydrated alcohol again, add an amount of reactive reagent, remove the chlorion and the sulfate ion of trace, after filtering the elimination insolubles, slough solvent.
3, the preparation method of a kind of ferric alkyl aryl sulfonate according to claim 2, it is characterized in that, positively charged ion in the reactive reagent is silver ions and barium ion, negatively charged ion is at least a in tosic acid root, Phenylsulfonic acid root, alkyl aryl sulfonate root, nitrate radical or the hydroxide radical, the add-on of response type reagent is to be as the criterion with detrimental impurity ionic amount, waits mole or excessive a little adding.
4, the preparation method of a kind of ferric alkyl aryl sulfonate according to claim 1, it is characterized in that, after after described step 4), also having the ferric alkyl aryl sulfonate process vacuum-drying of step 5) with the recrystallization purification, be dissolved in the alcoholic solvent, obtain the solution of ferric alkyl aryl sulfonate, described alcoholic solvent is at least a in ethanol, Virahol, the butanols.
According to the preparation method of the described a kind of ferric alkyl aryl sulfonate of each claim among the claim 1-4, it is characterized in that 5, the volume ratio of methyl alcohol and acetonitrile is 1: 5 in the mixed solvent.
6, a kind of preparation method of chain alkyl aromatic sulphonic acid iron is characterized in that, comprises following steps:
A) FERRIC CHLORIDE ANHYDROUS or Iron(III) chloride hexahydrate and chain alkyl aromatic azochlorosulfonate acid sodium react in water according to mol ratio (1: 2～1: 4);
B) filter the product of separating out in the water outlet, clean the back oven dry, make the crude product of chain alkyl aromatic sulphonic acid iron;
C) mixed solvent with methyl alcohol and acetonitrile carries out the recrystallization purification to crude product, obtains the finished product of chain alkyl aromatic sulphonic acid iron.
7, the preparation method of a kind of chain alkyl aromatic sulphonic acid iron according to claim 6, it is characterized in that, at described step b) and c) between b ' in steps) be dissolved in crude product in the dehydrated alcohol again, add an amount of reactive reagent, remove the chlorion and the sulfate ion of trace, after filtering the elimination insolubles, slough solvent.
8, the preparation method of a kind of chain alkyl aromatic sulphonic acid iron according to claim 7, it is characterized in that, positively charged ion in the reactive reagent is silver ions and barium ion, negatively charged ion is at least a in tosic acid root, Phenylsulfonic acid root, alkyl aryl sulfonate root, nitrate radical or the hydroxide radical, the add-on of response type reagent is to be as the criterion with detrimental impurity ionic amount, waits mole or excessive a little adding.
9, the preparation method of a kind of chain alkyl aromatic sulphonic acid iron according to claim 6, it is characterized in that, after after described step c), also having the chain alkyl aromatic sulphonic acid iron process vacuum-drying of step d) with the recrystallization purification, be dissolved in the alcoholic solvent, obtain the solution of chain alkyl aromatic sulphonic acid iron, described alcoholic solvent is at least a in ethanol, Virahol, the butanols.
According to the preparation method of the described a kind of chain alkyl aromatic sulphonic acid iron of each claim among the claim 6-9, it is characterized in that 10, the volume ratio of methyl alcohol and acetonitrile is 1: 5 in the mixed solvent.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101973913A (en) * | 2010-10-22 | 2011-02-16 | 山东星之联生物科技股份有限公司 | Clean synthetic method of high purity iron(III) p-toluenesulfonate |
| CN102464795A (en) * | 2010-11-18 | 2012-05-23 | 财团法人工业技术研究院 | Oxidant for forming solid capacitor, electrolyte composition comprising oxidant, solid capacitor and manufacturing method of solid capacitor |
| CN102557993A (en) * | 2011-12-30 | 2012-07-11 | 山东星之联生物科技股份有限公司 | Preparation method of oxidant as well as doping agent for synthesizing conductive high polymer |
| CN102617410A (en) * | 2012-03-15 | 2012-08-01 | 长春万成生物电子工程有限公司 | Method for purifying 3,4,5,6-tetrahalogenated phenolsulfonphthalein |
| CN102911089A (en) * | 2012-11-06 | 2013-02-06 | 广州化学试剂厂 | Method for preparing iron p-toluenesulfonate and solution thereof |
| CN103113268A (en) * | 2013-01-31 | 2013-05-22 | 深圳新宙邦科技股份有限公司 | Iron sulfonate and preparation method of alcoholic solution thereof |
| CN107827785A (en) * | 2017-11-07 | 2018-03-23 | 黄建文 | A kind of synthetic method of p-methyl benzenesulfonic acid iron |
| CN109369339A (en) * | 2018-11-01 | 2019-02-22 | 惠州市宙邦化工有限公司 | A kind of processing method of p-methyl benzenesulfonic acid iron butanol solution waste material |
| CN113024421A (en) * | 2019-12-25 | 2021-06-25 | 惠州市宙邦化工有限公司 | Purification method of p-toluenesulfonic acid iron solution |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3814730A1 (en) * | 1988-04-30 | 1989-11-09 | Bayer Ag | SOLID ELECTROLYTE AND ELECTROLYTE CONDENSERS CONTAINING THEM |
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| CN101973913A (en) * | 2010-10-22 | 2011-02-16 | 山东星之联生物科技股份有限公司 | Clean synthetic method of high purity iron(III) p-toluenesulfonate |
| CN101973913B (en) * | 2010-10-22 | 2012-09-19 | 山东星之联生物科技股份有限公司 | Clean synthesis method of high purity iron(III) p-toluenesulfonate |
| CN102464795A (en) * | 2010-11-18 | 2012-05-23 | 财团法人工业技术研究院 | Oxidant for forming solid capacitor, electrolyte composition comprising oxidant, solid capacitor and manufacturing method of solid capacitor |
| CN102557993B (en) * | 2011-12-30 | 2013-07-24 | 山东星之联生物科技股份有限公司 | Preparation method of oxidant as well as doping agent for synthesizing conductive high polymer |
| CN102557993A (en) * | 2011-12-30 | 2012-07-11 | 山东星之联生物科技股份有限公司 | Preparation method of oxidant as well as doping agent for synthesizing conductive high polymer |
| CN102617410B (en) * | 2012-03-15 | 2013-11-06 | 长春万成生物电子工程有限公司 | Method for purifying 3,4,5,6-tetrahalogenated phenolsulfonphthalein |
| CN102617410A (en) * | 2012-03-15 | 2012-08-01 | 长春万成生物电子工程有限公司 | Method for purifying 3,4,5,6-tetrahalogenated phenolsulfonphthalein |
| CN102911089A (en) * | 2012-11-06 | 2013-02-06 | 广州化学试剂厂 | Method for preparing iron p-toluenesulfonate and solution thereof |
| CN102911089B (en) * | 2012-11-06 | 2013-12-11 | 广州化学试剂厂 | Method for preparing iron p-toluenesulfonate and solution thereof |
| CN103113268A (en) * | 2013-01-31 | 2013-05-22 | 深圳新宙邦科技股份有限公司 | Iron sulfonate and preparation method of alcoholic solution thereof |
| CN103113268B (en) * | 2013-01-31 | 2016-03-02 | 深圳新宙邦科技股份有限公司 | The preparation method of sulfonic acid iron and alcoholic solution thereof |
| CN107827785A (en) * | 2017-11-07 | 2018-03-23 | 黄建文 | A kind of synthetic method of p-methyl benzenesulfonic acid iron |
| CN109369339A (en) * | 2018-11-01 | 2019-02-22 | 惠州市宙邦化工有限公司 | A kind of processing method of p-methyl benzenesulfonic acid iron butanol solution waste material |
| CN109369339B (en) * | 2018-11-01 | 2021-09-17 | 惠州市宙邦化工有限公司 | Method for treating waste p-toluenesulfonic acid iron n-butanol solution |
| CN113024421A (en) * | 2019-12-25 | 2021-06-25 | 惠州市宙邦化工有限公司 | Purification method of p-toluenesulfonic acid iron solution |
| CN113024421B (en) * | 2019-12-25 | 2022-06-28 | 惠州市宙邦化工有限公司 | Purification method of p-toluenesulfonic acid iron solution |
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