CN105540923B - A kind of method of 2 mercaptopyridine N oxides in removal waste water - Google Patents

A kind of method of 2 mercaptopyridine N oxides in removal waste water Download PDF

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CN105540923B
CN105540923B CN201510989031.9A CN201510989031A CN105540923B CN 105540923 B CN105540923 B CN 105540923B CN 201510989031 A CN201510989031 A CN 201510989031A CN 105540923 B CN105540923 B CN 105540923B
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waste water
pyrithione
layering
organic solvent
hours
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CN105540923A (en
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梁建明
孙常清
张大贵
颜国和
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ZHEJIANG PEGENT CHEMICAL CO Ltd
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    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F9/00—Multistage treatment of water, waste water or sewage
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/26—Treatment of water, waste water, or sewage by extraction
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/66—Treatment of water, waste water, or sewage by neutralisation; pH adjustment
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/30—Organic compounds
    • C02F2101/34—Organic compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/30—Organic compounds
    • C02F2101/38—Organic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/30—Organic compounds
    • C02F2101/40—Organic compounds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
    • C02F2103/34—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32
    • C02F2103/36—Nature of the water, waste water, sewage or sludge to be treated from industrial activities not provided for in groups C02F2103/12 - C02F2103/32 from the manufacture of organic compounds

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  • Life Sciences & Earth Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Processing Of Solid Wastes (AREA)
  • Removal Of Specific Substances (AREA)
  • Treatment Of Water By Oxidation Or Reduction (AREA)
  • Extraction Or Liquid Replacement (AREA)

Abstract

The method of 2 mercaptopyridine N oxides and its recycling in waste water are removed the invention discloses a kind of.The present invention comprises the following steps：(1) waste water containing 2 mercaptopyridine N oxides and organic solvent are pressed 7 at room temperature:1‑12:1 mixing, after stirring 12 hours, 0.5 1 hours are stood, layering, divides and removes waste water layer；After measured, 2 mercaptopyridine N oxide contents in the waste water layer removed are divided to be less than 0.05%；(2) at room temperature, deionized water is added in the organic solvent after step (1) layering, the sodium hydroxide solution that mass concentration is 30% is then added dropwise while stirring, until the pH value of mixed solution is 9 10,0.5 1 hours are stood after continuing stirring 0.5 1 hours, is layered.The present invention effectively reduces the content of 2 mercaptopyridine N oxides in waste water, and reduces the colourity of waste water and suspension, is offered convenience for three-protection design.

Description

A kind of method of pyrithione in removal waste water
Technical field
The invention belongs to chemical field, more particularly to a kind of side for removing 2- mercaptopyridine-N- oxides in waste water Method and its recycling.
Background technology
Pyrithione is slightly soluble in water, is soluble in highly basic, and it is organic to be dissolved in halogenated hydrocarbons, aromatic hydrocarbon, ether and ester etc. Solvent, for preparing various pyrithiones, and pyrithione as bactericide be widely used in daily washing cosmetic and The fields such as paint of coating industry.At present in industrial production 2- mercapto-pyridine-n-oxides preparation, typically using 2- chloropyridines as Initiation material, it is made through hydrogen peroxide oxidation, mercaptolation, concrete technology synthetic route is as follows：
In actual production, after 2- chloropyridines are oxidized, sulfhydrylation obtains pyrithione sodium salt, 2- mercaptos Pyridine-N-oxide sodium salt need to use hydrochloric acid or sulfuric acid to adjust pH to 2-3, separate out 2- mercapto-pyridine-n-oxide solids, filtering Obtained pyrithione solid repeated hydrogenation sodium hydroxide solution dissolving, is made pyrithione sodium salt Solution, then go to prepare various pyrithiones, this acid out and alkali soluble process are a purification process, it is therefore an objective to improve 2- mercaptos Pyridine-N-oxide sodium salt quality.
Present problem is that after the pyrithione solid of acid out filters, 0.3- is still remained in caused waste water PH value and filtration temperature when how much 0.4% pyrithione, its residual quantity depend primarily on filtering etc..Cause Pyrithione be not in itself it is very stable, for a long time meet light and heat can change colour, also easily with it is other in other waste water Compound is reacted, so, the height of concentration containing pyrithione can produce certain colourity and turbidity in waste water, directly enter Enter wastewater treatment equipment, waste water can be made to be difficult to handle, moreover, pyrithione is a bactericide, to wastewater biochemical The microorganism of processing has inhibitory action, and according to our practical experiences, caused waste water contains pyrithione after filtering Content is relatively beneficial to wastewater biochemical below 0.05% and handled.
2- mercaptopyridine-N- oxygen how is removed and utilized to the waste water of the pyrithione containing 0.3-0.4% Compound, document report is had no at present, generally zinc sulfate or copper sulphate can be added to produce ZPT (copper) precipitation in waste water To remove pyrithione, but ZPT (copper) content reclaimed is low, and need to further purify could be effectively sharp With, and new pollution can be produced.So, we need to seek removing and the Application way of new pyrithione.
The content of the invention
The present invention seeks in view of the shortcomings of the prior art, there is provided one kind removes pyrithione in waste water Method and its recycling.
The technical solution adopted for the present invention to solve the technical problems step is as follows：
Step (1) mixes with organic solvent in certain ratio at room temperature, by the waste water containing pyrithione Close, after stirring 1-2 hours, stand 0.5-1 hours, layering, divide and remove waste water layer.After measured, 2- sulfydryls pyrrole in the waste water layer removed is divided Pyridine-N- oxide contents are less than 0.05%, and point waste water removed is placed in Waste Water Treatment.
The waste water containing pyrithione and the mixed proportion of organic solvent mentioned in described step (1) is 7:1-12:1。
Described organic solvent includes the toluene and Mixed XYLENE of arene, the dichloromethane of halogenated hydrocarbon, three chloromethanes Alkane and 1,2- dichloromethane, ethyl acetate, methyl acetate and the Ethyl formate of esters, the methyl tertiary butyl ether(MTBE) and isopropyl of ethers Ether；
The preferred toluene of described organic solvent and methyl tertiary butyl ether(MTBE).
The pH value for the waste water containing pyrithione mentioned in described step (1) is 2-6.
Step (2) is added in the organic solvent after step (1) layering at room temperature, by deionized water, and then side is stirred The sodium hydroxide solution that mass concentration is 30% is added dropwise in side, until the pH value of mixed solution is 9-10, continues to stir 0.5-1 hours 0.5-1 hours are stood afterwards, layering, the water layer separated is pyrithione sodium salt solution, and 2- sulfydryls pyrrole in water layer The content of pyridine-N- oxide sodium salts is 35-41%, and the water layer can be used in producing pyrithione.
Organic solvent layer after being layered in described step (2) can be used in 2- sulfydryls pyrrole in next group waste water after benefit is measured The removing and its recycling of pyridine-N- oxides.
The deionized water and the mass ratio of waste water mentioned in described step (2) are 1：300-500.
The present invention has the beneficial effect that：
The present invention not only effectively reduces the content of pyrithione in waste water, and makes the colourity of waste water Reduce with suspension, offered convenience for three-protection design, and the pyrithione sodium salt reclaimed can be used for producing pyrrole Pyridine thioketones salt, brings certain economic benefit.
If in pyrithione sodium salt production process, the 2- mercaptopyridine-N- oxides that acid out goes out are only Filter, is directly extracted with organic solvent, and this can consume a large amount of organic solvents, increase production cost and safety in production hidden danger, and meeting The risk of a large amount of organic solvents is remained in increase final products pyrithione.And the present invention makes whole technique green.
Embodiment
With reference to example, the invention will be further described.
Embodiment 1
In 5L glass reaction bottle, add 0.5 ㎏ toluene, add pH value be adjusted in advance 3-4 containing 2- mercaptopyridines- The ㎏ of N- oxides waste water 4.5, is stirred at room temperature 1 hour, sampling of wastewater analysis, at this moment-the N- of mercaptopyridine containing 2- oxygen in waste water Compound is 0.042%, stands 0.5 hour, layering, separates waste water layer.
Layering finishes, and adds 0.01 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 0.015 is added dropwise, and is 9 to pH value, stirs Mix 0.5 hour, stand 0.5 hour, layering, separate the ㎏ of water layer 0.039, its pyrithione sodium salt content is 40.3%.
Embodiment 2
In 5L glass reaction bottle, 0.6 ㎏ dichloromethane is added, pH value is added and contains 2- mercaptopyridines-N- for 2-3 The ㎏ of oxide waste water 4.5, it is stirred at room temperature 1 hour, sampling of wastewater analysis, is containing pyrithione in waste water 0.033%, 0.5 hour is stood, layering, separates waste water layer.
Layering finishes, and adds 0.015 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 0.016 is added dropwise, and is 9 to pH value, stirs Mix 0.5 hour, stand 0.5 hour, layering, separate the ㎏ of water layer 0.046, its pyrithione sodium salt content is 35.5%.
Embodiment 3
In 5L glass reaction bottle, 0.5 ㎏ methyl tertiary butyl ether(MTBE)s are added, add that pH value is adjusted to 4-5 in advance contains 2- The ㎏ of mercapto-pyridine-n-oxide waste water 4.5, it is stirred at room temperature 1 hour, sampling of wastewater analysis, mercaptopyridine containing 2- in waste water- N- oxides are 0.038%, stand 0.5 hour, layering, separate waste water layer.
Layering finishes, and adds 0.01 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 0.015 is added dropwise, and is 9 to pH value, stirs Mix 0.5 hour, stand 0.5 hour, layering, separate the ㎏ of water layer 0.04, its pyrithione sodium salt content is 40.2%.
Embodiment 4
In 5L glass reaction bottle, 0.4 ㎏ methyl tertiary butyl ether(MTBE)s are added, add that pH value is adjusted to 4-5 in advance contains 2- The ㎏ of mercapto-pyridine-n-oxide waste water 4.5, it is stirred at room temperature 2 hours, sampling of wastewater analysis, mercaptopyridine containing 2- in waste water- N- oxides are 0.04%, stand 1 hour, layering, separate waste water layer.
Layering finishes, and adds 0.009 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 0.015 is added dropwise, and is 10 to pH value, Stirring 0.5 hour, 0.5 hour is stood, layering, separate the ㎏ of water layer 0.038, its pyrithione sodium salt content is 41.0%.
Embodiment 5
In 5L glass reaction bottle, 0.5 ㎏ ethyl acetate is added, add that pH value is adjusted to 5-6 in advance contains 2- sulfydryls The ㎏ of pyridine-N-oxides waste water 4.5, it is stirred at room temperature 1 hour, sampling of wastewater analysis ,-N- the oxygen of mercaptopyridine containing 2- in waste water Compound is 0.041%, stands 0.5 hour, layering, separates waste water layer.
Layering finishes, and adds 0.01 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 0.017 is added dropwise, and is 9 to pH value, stirs Mix 0.5 hour, stand 0.5 hour, layering, separate the ㎏ of water layer 0.042, its pyrithione sodium salt content is 38.8%.
Embodiment 6
In 5L glass reaction bottle, 0.45 ㎏ methyl acetates are added, add that pH value is adjusted to 5-6 in advance contains 2- mercaptos The ㎏ of pyridine-N-oxide waste water 4.5, it is stirred at room temperature 1 hour, sampling of wastewater analysis ,-the N- of mercaptopyridine containing 2- in waste water Oxide is 0.042%, stands 0.5 hour, layering, separates waste water layer.
Layering finishes, and adds 0.01 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 0.016 is added dropwise, and is 9 to pH value, stirs Mix 0.5 hour, stand 0.5 hour, layering, separate the ㎏ of water layer 0.041, its pyrithione sodium salt content is 39.1%.
Embodiment 7
In 5L glass reaction bottle, 3.75 ㎏ Ethyl formates are added, add that pH value is adjusted to 5-6 in advance contains 2- mercaptos The ㎏ of pyridine-N-oxide waste water 4.5, it is stirred at room temperature 1 hour, sampling of wastewater analysis ,-the N- of mercaptopyridine containing 2- in waste water Oxide is 0.046%, stands 0.5 hour, layering, separates waste water layer.
Layering finishes, and adds 0.01 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 0.016 is added dropwise, and is 9 to pH value, stirs Mix 0.5 hour, stand 0.5 hour, layering, separate the ㎏ of water layer 0.038, its pyrithione sodium salt content is 39.3%.
Embodiment 8
In 5L glass reaction bottle, add 0.643 ㎏ chloroforms, add pH value be 2-3 containing 2- mercaptopyridines- The ㎏ of N- oxides waste water 4.5, is stirred at room temperature 1 hour, sampling of wastewater analysis, contains pyrithione in waste water For 0.03%, 0.5 hour is stood, layering, separates waste water layer.
Layering finishes, and adds 0.015 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 0.016 is added dropwise, and is 9 to pH value, stirs Mix 0.5 hour, stand 0.5 hour, layering, separate the ㎏ of water layer 0.046, its pyrithione sodium salt content is 36.7%.
Embodiment 9
In 5L glass reaction bottle, 0.6 ㎏ 1 is added, 2- dichloroethanes, pH value is added and contains 2- sulfydryl pyrroles for 2-3 The ㎏ of pyridine-N- oxides waste water 4.5, is stirred at room temperature 1 hour, sampling of wastewater analysis, and-the N- of mercaptopyridine containing 2- is aoxidized in waste water Thing is 0.034%, stands 0.5 hour, layering, separates waste water layer.
Layering finishes, and adds 0.015 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 0.016 is added dropwise, and is 9 to pH value, stirs Mix 0.5 hour, stand 0.5 hour, layering, separate the ㎏ of water layer 0.047, its pyrithione sodium salt content is 35.1%.
Embodiment 10
In 5L glass reaction bottle, 0.55 ㎏ Mixed XYLENEs are added, add that pH value is adjusted to 3-4 in advance contains 2- mercaptos The ㎏ of pyridine-N-oxide waste water 4.5, it is stirred at room temperature 1 hour, sampling of wastewater analysis, at this moment the pyrrole of sulfydryl containing 2- in waste water Pyridine-N- oxides are 0.043%, stand 0.5 hour, layering, separate waste water layer.
Layering finishes, and adds 0.01 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 0.015 is added dropwise, and is 9 to pH value, stirs Mix 0.5 hour, stand 0.5 hour, layering, separate the ㎏ of water layer 0.04, its pyrithione sodium salt content is 40.2%.
Embodiment 11
In 5L glass reaction bottle, 0.45 ㎏ isopropyl ethers are added, add that pH value is adjusted to 4-5 in advance contains 2- sulfydryls The ㎏ of pyridine-N-oxides waste water 4.5, it is stirred at room temperature 1 hour, sampling of wastewater analysis ,-N- the oxygen of mercaptopyridine containing 2- in waste water Compound is 0.039%, stands 0.5 hour, layering, separates waste water layer.
Layering finishes, and adds 0.01 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 0.015 is added dropwise, and is 9 to pH value, stirs Mix 0.5 hour, stand 0.5 hour, layering, separate the ㎏ of water layer 0.039, its pyrithione sodium salt content is 40.5%.
Embodiment 12：
In 5000L reactor, 500 ㎏ toluene are added, contain 2- mercaptopyridine-N- oxygen with what pump squeezed into pH value 2-3 The ㎏ of compound waste water 4500, it is stirred at room temperature 1 hour, sampling of wastewater analysis, is containing pyrithione in waste water 0.044%, 1 hour is stood, layering, the waste water separated removes Waste Water Treatment.
Layering finishes, and adds 10 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 15 is added dropwise, and is 9 to pH values, stirring 0.5 Hour, 1 hour is stood, layering, water layer barrelling is separated, is weighed as 40 ㎏, its content is 39.5%.This 2- mercaptopyridine-N- oxygen After compound sodium salt solution is concentrated, for producing pyrithione.Toluene is still in a kettle, useless for lower batch after appropriate benefit amount The removing and utilization of pyrithione in water.
Embodiment 13：
In the 5000L of embodiment 12 reactor, 10 ㎏ toluene are added, squeeze into pH value with pump is adjusted to containing for 4-5 in advance There is the ㎏ of pyrithione waste water 4500, be stirred at room temperature 1 hour, sampling of wastewater analysis, 2- mercaptos contained by waste water Pyridine-N-oxide is 0.041%, stands 1 hour, and layering, the waste water separated removes Waste Water Treatment.
Layering finishes, and adds 10 ㎏ deionized waters, and the ㎏ of 30% sodium hydroxide solution 15 is added dropwise, and is 10 to pH values, stirring 0.5 hour, 1 hour is stood, layering, water layer barrelling is separated, is weighed as 39.8 ㎏, its content is 39.9%.This 2- sulfydryl pyrrole After pyridine-N- oxide, sodiums salting liquid is concentrated, for producing pyrithione.Toluene still in a kettle, after appropriate benefit amount, is used for The removing and utilization of pyrithione in waste water are criticized down.

Claims (3)

  1. A kind of 1. method for removing pyrithione in waste water, it is characterised in that comprise the following steps：
    Step (1) at room temperature, the waste water containing pyrithione is mixed with organic solvent in certain ratio, stirred After mixing 1-2 hours, 0.5-1 hours are stood, layering, divides and removes waste water layer；After measured, 2- mercaptopyridines-N- in the waste water layer removed is divided Oxide content is less than 0.05%, and point waste water removed is placed in Waste Water Treatment；
    The waste water containing pyrithione and the mixed proportion of organic solvent mentioned in described step (1) are 7:1- 12:1；
    Described organic solvent is selected from the toluene and Mixed XYLENE of arene, the dichloromethane of halogenated hydrocarbon, chloroform and 1,2- dichloromethane, ethyl acetate, methyl acetate and the Ethyl formate of esters, in the methyl tertiary butyl ether(MTBE) and isopropyl ether of ethers It is one or more；
    Step (2) is added in the organic solvent after step (1) layering at room temperature, by deionized water, then drips while stirring Add the sodium hydroxide solution that mass concentration is 30%, until the pH value of mixed solution be 9-10, continue quiet after stirring 0.5-1 hours .5-1 hours are set to 0, are layered, the water layer separated is pyrithione sodium salt solution, and 2- mercaptopyridines in water layer- The content of N- oxide sodium salts is 35-41%, and the water layer can be used in producing pyrithione；
    The deionized water and the mass ratio of waste water mentioned in described step (2) are 1：300-500；
    The pH value for the waste water containing pyrithione mentioned in described step (1) is 2-6.
  2. A kind of 2. method for removing pyrithione in waste water as claimed in claim 1, it is characterised in that step (1) organic solvent described in is one or more in toluene and methyl tertiary butyl ether(MTBE).
  3. 3. a kind of method for removing pyrithione in waste water as claimed in claim 1, it is characterised in that described The step of (2) in be layered after organic solvent layer can be used in pyrithione in next group waste water after benefit is measured Removing.
CN201510989031.9A 2015-12-24 2015-12-24 A kind of method of 2 mercaptopyridine N oxides in removal waste water Active CN105540923B (en)

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Publication number Priority date Publication date Assignee Title
CN107602459A (en) * 2017-08-22 2018-01-19 重庆中邦科技有限公司 A kind of process for effectively purifying of sodium pyrithione
CN108439646B (en) * 2018-04-17 2020-08-14 中南大学 Pretreatment method of high-concentration organic wastewater in production process of mercapto heterocyclic compounds

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CN105129894A (en) * 2015-09-09 2015-12-09 江西玛德精细化学工业有限公司 High efficiency extraction method of T-acid mother liquor
CN105174348A (en) * 2015-10-30 2015-12-23 朱忠良 Separation method for strong-polarity organic matter molecules in coking wastewater

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EP1889811A1 (en) * 2006-08-17 2008-02-20 Unilever N.V. Aqueous media purification method and device comprising a functionalised polyhipe resin
CN101074211A (en) * 2007-06-18 2007-11-21 浙江工业大学 Process for treating high-purity pyridine solution
CN102127008A (en) * 2011-01-18 2011-07-20 中国中化股份有限公司 Method for recycling pyridine from chemical production wastewater
CN103570609A (en) * 2013-10-28 2014-02-12 南通天泽化工有限公司 Preparation method for 2,3-dichloropyridine
CN104591452A (en) * 2015-01-27 2015-05-06 浙江工商大学 Method for treating wastewater generated in production of 2-naphthol
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CN105129894A (en) * 2015-09-09 2015-12-09 江西玛德精细化学工业有限公司 High efficiency extraction method of T-acid mother liquor
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