CN109485603A - A kind of preparation method of the 8-hydroxyquinoline of no solid waste output - Google Patents
A kind of preparation method of the 8-hydroxyquinoline of no solid waste output Download PDFInfo
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- CN109485603A CN109485603A CN201811284259.8A CN201811284259A CN109485603A CN 109485603 A CN109485603 A CN 109485603A CN 201811284259 A CN201811284259 A CN 201811284259A CN 109485603 A CN109485603 A CN 109485603A
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- hydroxyquinoline
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
- C01D5/00—Sulfates or sulfites of sodium, potassium or alkali metals in general
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of preparation methods of the 8-hydroxyquinoline of no solid waste output, glycerol is formed into methacrylaldehyde under sulfuric acid dehydration, methacrylaldehyde reacts cyclic condensation with o-aminophenol, 8-hydroxyquinoline semi-finished product are dehydrated into through o-nitrophenol oxidation again, and the sulfuric acid in semi-finished product is neutralized with liquid alkaline, 8-hydroxyquinoline crude product is obtained after centrifuge is separated by solid-liquid separation again, crude product is distilled, is sliced to obtain 8-hydroxyquinoline.Present invention reaction is mild, and industrialized producing technology strong operability, reaction is easy to control, and subsequent processing is simple, and equipment investment is few, energy saving, and has recycled raw material and increased economic benefit, and the yield of 8-hydroxyquinoline can reach 85% or more.
Description
Technical field
The invention belongs to chemical industry synthesis fields, and in particular to a kind of preparation method of 8 oxyquinolines.
Background technique
8-hydroxyquinoline is a kind of white or pale yellow crystals or crystalline powder, not soluble in water and ether, be dissolved in ethyl alcohol,
Acetone, chloroform, benzene or diluted acid can distil, and corrosivity is smaller, low toxicity, LD504800mg/kg.Traditional 8-hydroxyquinoline be by
O-aminophenol is made through cyclization reaction.Traditional technique for preparing 8-hydroxyquinoline is that glycerol is added in acid tolerance response pot,
It is slowly added into the concentrated sulfuric acid under stiring, while o-aminophenol, o-nitrophenol being sequentially added, adds oleum, adds
Heat is warming up to 125 DEG C, stops heating, warms naturally to 140 DEG C, keeps the temperature 4h, is cooled to 100 DEG C and holds 10 times of amounts hereinafter, being pumped into
In the acidproof pot of water (based on o-aminophenol), stirring is heated to 75 ~ 80 DEG C, being neutralized to pH with 30% sodium hydroxide solution is
7 ~ 7.2, sediment is released while hot, is cooled to bulk, through Decompression Sublimation, obtains 8-hydroxyquinoline finished product.There are two for this technique
Disadvantage: it firstly, traditional handicraft is to be added at one time oleum, heats up after oleum first either is added at low temperature, also
It is first to heat up that oleum is added afterwards, the amount of being added at one time is big, and sulfuric acid reaction acutely, unevenly, is easy to produce a variety of by-products
To later collection using that can have an impact, all very high, 8- hydroxyl is required to technological operation, control moreover, being added at one time sulfuric acid
The yield of quinoline is also relatively low only 70% or so；Secondly, centrifuge mother liquor is concentrated by concentration kettle in traditional handicraft, residue is made
Dangerous waste processing is concentrated by triple effect evaporator, and recycling industry makees dangerous waste processing, the glycerol in residue is caused not return again
It receives and utilizes, process is tedious, cost is excessively high for processing dangerous waste.
Summary of the invention
Goal of the invention: in view of the above-mentioned deficiencies in the prior art, it is an object of the present invention to provide a kind of 8- hydroxyl of no solid waste output
The preparation method of base quinoline.
Technical solution: in order to achieve the above object of the invention, what the present invention was specifically performed by: a kind of no solid waste output
8-hydroxyquinoline preparation method, glycerol is formed into methacrylaldehyde under sulfuric acid dehydration, methacrylaldehyde is anti-with o-aminophenol
It answers cyclic condensation, then is dehydrated into 8-hydroxyquinoline semi-finished product through o-nitrophenol oxidation, and with liquid alkaline by the sulfuric acid in semi-finished product
It neutralizes, then obtains 8-hydroxyquinoline crude product after centrifuge is separated by solid-liquid separation, crude product is distilled, is sliced to obtain 8-hydroxyquinoline.
Wherein, the mass ratio of the glycerol, sulfuric acid, o-nitrophenol, o-aminophenol, liquid alkaline and water be 10 ~ 15:14 ~
20:2~5:4~8:35~40:1~2。
Wherein, the content of sodium hydroxide is 30wt% in the liquid alkaline.
Specifically, 8-hydroxyquinoline preparation method the following steps are included:
(1) stand-by by formula measurement glycerol, sulfuric acid, o-nitrophenol, o-aminophenol, liquid alkaline and water；
(2) it is condensed: reaction kettle is added in glycerol, the sulfuric acid of formula sulfuric acid total weight 50 ~ 55% is added dropwise, and controls temperature in the kettle and exists
60 DEG C hereinafter, drop acid after stir 15 ~ 20 minutes, then sequentially add o-aminophenol, o-nitrophenol, continue control kettle
It below interior temperature 60 C and stirs 30 ~ 40 minutes, reaction kettle is heated, when temperature in the kettle rises to 130 ~ 135 DEG C, be added dropwise
Residual sulfuric acid simultaneously controls 135 ~ 140 DEG C of temperature, keeps the temperature 2 ~ 3 hours for 135 ~ 140 DEG C of temperature of control after the concentrated sulfuric acid is added dropwise, heat preservation
After material in kettle is cooled to 100 DEG C, into reaction kettle plus water management temperature that remaining unreacted is steamed no more than 125 DEG C is adjacent
Temperature in the kettle is cooled to 100 DEG C or less after distillation by nitrophenol；
(3) it neutralizes: liquid alkaline being slowly added dropwise into reaction kettle, and controls temperature 60 C hereinafter, when pH value reaches 6.5 ~ 7.0 in kettle
Stop that liquid alkaline is added dropwise, by being centrifugally separating to obtain the crude product and centrifuge mother liquor of solid 8-hydroxyquinoline, aqueous, sulphur in centrifuge mother liquor
Sour sodium, glycerol and a small amount of by-product；
(4) MVR evaporates: after MVR is concentrated by evaporation, sodium sulphate is precipitated centrifuge mother liquor with crystal form, is centrifugated out sodium sulphate,
And mainly contain glycerol, Shao Liangshui, sodium sulphate and reaction by-product in residual mother liquor；
(5) glycerol recycles: residual mother liquor squeezes into glycerol distillation kettle with dehvery pump, is warming up to 100 DEG C and distills 2 ~ 3 under condition of negative pressure
Hour, the waste water steamed is delivered to Sewage Disposal, then heats to 180 DEG C and distill 4 ~ 5 hours under condition of negative pressure, steam
Glycerol, sulfur acid sodium, a small amount of glycerol and a small amount of by-product in bottoms,
Bottoms enter roaster roasting recycling sodium sulphate；
(6) it distills: distillation still will be added by the crude product for the 8-hydroxyquinoline being centrifugally separating to obtain, be warming up to 120 DEG C and steam water
Point, then control vacuum degree in kettle and be lower than -0.09Mpa, kettle temperature starts to distill at 160 ~ 180 DEG C, when kettle temperature reach 200 DEG C with
When upper, distillation is finished, and collects distillate, and residue send to roaster and roasts recycling sodium sulphate；
(7) it is sliced, packs: will be cooled down after the distillate import slices machine of collection, and be sliced, pack, obtain finished product 8- hydroxyl
Base quinoline.
Wherein, the step (4), step (5) gained water are back to step (3) and carry out neutralization reaction.
The utility model has the advantages that the present invention, compared with traditional technology, there are following advantages:
(1) part of sulfuric acid is added dropwise at 60 DEG C in the present invention, after be warming up to 140 DEG C of reactions, and residual sulfuric acid is added dropwise, to make entirely
Condensation reaction is mild, and industrialized producing technology strong operability, reaction is easy to control；
(2) present invention recycles sodium sulphate, remaining residual ight vacuum distillation using mechanical steam recompression technology to centrifuge mother liquor
Mode, recycling glycerol are reused, and residue enters roaster and continues roasting recycling sodium sulphate, so that subsequent processing is simple, equipment
Less investment, it is energy saving, and recycled raw material and increased economic benefit；
(3) yield of 8-hydroxyquinoline obtains stablizing raising in the present invention, can reach 85% or more.
Specific embodiment
Embodiment 1:
10:14:2:4:35:1 in mass ratio takes glycerol, sulfuric acid, o-nitrophenol, o-aminophenol, liquid alkaline and water stand-by；It will be sweet
Reaction kettle is added in oil, and the sulfuric acid of formula sulfuric acid total weight 50 ~ 55% is added dropwise, and controls temperature in the kettle at 60 DEG C hereinafter, drop acid finishes
It stirs 15 ~ 20 minutes afterwards, then sequentially adds o-aminophenol, o-nitrophenol, continue 60 DEG C of temperature in the kettle of control or less simultaneously
Stirring 30 ~ 40 minutes, heats reaction kettle, when temperature in the kettle rises to 130 ~ 135 DEG C, residual sulfuric acid is added dropwise and controls temperature
135 ~ 140 DEG C of degree keeps the temperature 2 ~ 3 hours for 135 ~ 140 DEG C of temperature of control after the concentrated sulfuric acid is added dropwise, by material in kettle after heat preservation
100 DEG C are cooled to, into reaction kettle plus water management temperature is not more than 125 DEG C and steams remaining unreacted o-nitrophenol, has distilled
Temperature in the kettle is cooled to 100 DEG C or less after finishing；Liquid alkaline is slowly added dropwise into reaction kettle, and controls temperature 60 C hereinafter, working as kettle
Interior pH value stops that liquid alkaline is added dropwise when reaching 6.5 ~ 7.0, female by the crude product and centrifugation that are centrifugally separating to obtain solid 8-hydroxyquinoline
Liquid, aqueous, sodium sulphate, glycerol and a small amount of by-product in centrifuge mother liquor；Centrifuge mother liquor is after MVR is concentrated by evaporation, and sodium sulphate is with crystalline substance
Body form is precipitated, and is centrifugated out sodium sulphate, and mainly contains glycerol, Shao Liangshui, sodium sulphate and reaction by-product in residual mother liquor；
Residual mother liquor squeezes into glycerol distillation kettle with dehvery pump, is warming up to 100 DEG C and distills 2 ~ 3 hours under condition of negative pressure, the waste water steamed
It is delivered to Sewage Disposal, 180 DEG C is then heated to and is distilled 4 ~ 5 hours under condition of negative pressure, steams glycerol, in bottoms
Sulfur acid sodium, a small amount of glycerol and a small amount of by-product, bottoms enter roaster roasting recycling sodium sulphate；Centrifuge separation will be passed through
Distillation still is added in the crude product of obtained 8-hydroxyquinoline, is warming up to 120 DEG C and steams moisture, then control in kettle vacuum degree lower than-
0.09Mpa, kettle temperature start to distill at 160 ~ 180 DEG C, and when kettle temperature reaches 200 DEG C or more, distillation is finished, and collect distillate, residual
Slag send to roaster and roasts recycling sodium sulphate；It will be cooled down after the distillate import slices machine of collection, and be sliced, pack, obtained
To finished product 8-hydroxyquinoline.
Embodiment 2:
15:20:5:8:40:2 in mass ratio takes glycerol, sulfuric acid, o-nitrophenol, o-aminophenol, liquid alkaline and water to wait for
With；Glycerol is added reaction kettle, the sulfuric acid of formula sulfuric acid total weight 50 ~ 55% is added dropwise, and control temperature in the kettle at 60 DEG C hereinafter,
It is stirred 15 ~ 20 minutes after drop acid, then sequentially adds o-aminophenol, o-nitrophenol, continue to control temperature in the kettle 60
DEG C or less and stir 30 ~ 40 minutes, reaction kettle is heated, when temperature in the kettle rises to 130 ~ 135 DEG C, be added dropwise residual sulfuric acid
And 135 ~ 140 DEG C of temperature are controlled, and 2 ~ 3 hours are kept the temperature for 135 ~ 140 DEG C of temperature of control after the concentrated sulfuric acid is added dropwise, it will after heat preservation
Material is cooled to 100 DEG C in kettle, and into reaction kettle plus water management temperature is not more than 125 DEG C and steams remaining unreacted ortho-nitrophenyl
Temperature in the kettle is cooled to 100 DEG C or less after distillation by phenol；Liquid alkaline is slowly added dropwise into reaction kettle, and controls temperature 60 C
Hereinafter, stopping that liquid alkaline is added dropwise when pH value reaches 6.5 ~ 7.0 in kettle, by the crude product for being centrifugally separating to obtain solid 8-hydroxyquinoline
And centrifuge mother liquor, aqueous, sodium sulphate, glycerol and a small amount of by-product in centrifuge mother liquor；Centrifuge mother liquor is after MVR is concentrated by evaporation, sulphur
Sour sodium is precipitated with crystal form, is centrifugated out sodium sulphate, and mainly containing glycerol, Shao Liangshui, sodium sulphate and anti-in residual mother liquor
Answer byproduct；Residual mother liquor squeezes into glycerol distillation kettle with dehvery pump, is warming up to 100 DEG C and distills 2 ~ 3 hours under condition of negative pressure, steams
Waste water out is delivered to Sewage Disposal, is then heated to 180 DEG C and is distilled 4 ~ 5 hours under condition of negative pressure, steams glycerol, is steamed
Sulfur acid sodium in residue, a small amount of glycerol and a small amount of by-product are evaporated, bottoms enter roaster roasting recycling sodium sulphate；It will pass through
Distillation still is added in the crude product for the 8-hydroxyquinoline being centrifugally separating to obtain, and is warming up to 120 DEG C and steams moisture, then controls vacuum in kettle
Degree is lower than -0.09Mpa, and kettle temperature starts to distill at 160 ~ 180 DEG C, and when kettle temperature reaches 200 DEG C or more, distillation is finished, and collects and steams
Distillate, residue send to roaster and roast recycling sodium sulphate；It will be cooled down after the distillate import slices machine of collection, and be sliced,
Packaging, obtains finished product 8-hydroxyquinoline.
Embodiment 3:
11:14.4:2.7:4.6:38.2:1 in mass ratio takes glycerol, sulfuric acid, o-nitrophenol, o-aminophenol, liquid alkaline and water
For use；Glycerol is added reaction kettle, the sulfuric acid of formula sulfuric acid total weight 50 ~ 55% is added dropwise, and control temperature in the kettle 60 DEG C with
Under, it is stirred 15 ~ 20 minutes after drop acid, then sequentially adds o-aminophenol, o-nitrophenol, continue to control temperature in the kettle
60 DEG C or less and stirring 30 ~ 40 minutes, reaction kettle is heated, when temperature in the kettle rises to 130 ~ 135 DEG C, remaining sulphur is added dropwise
Acid simultaneously controls 135 ~ 140 DEG C of temperature, 2 ~ 3 hours is kept the temperature for 135 ~ 140 DEG C of temperature of control after the concentrated sulfuric acid is added dropwise, after heat preservation
Material in kettle is cooled to 100 DEG C, into reaction kettle plus water management temperature is not more than 125 DEG C and steams remaining unreacted ortho-nitrophenyl
Temperature in the kettle is cooled to 100 DEG C or less after distillation by phenol；(3) it neutralizes: liquid alkaline being slowly added dropwise into reaction kettle, and controls
Temperature 60 C when pH value reaches 6.5 ~ 7.0 in kettle hereinafter, stop that liquid alkaline is added dropwise, by being centrifugally separating to obtain solid 8- hydroxyl quinoline
The crude product and centrifuge mother liquor of quinoline, aqueous, sodium sulphate, glycerol and a small amount of by-product in centrifuge mother liquor；Centrifuge mother liquor evaporates dense through MVR
After contracting, sodium sulphate is precipitated with crystal form, is centrifugated out sodium sulphate, and mainly contains glycerol, Shao Liangshui, sulfuric acid in residual mother liquor
Sodium and reaction by-product；Residual mother liquor squeezes into glycerol distillation kettle with dehvery pump, is warming up to 100 DEG C and distills 2 ~ 3 under condition of negative pressure
Hour, the waste water steamed is delivered to Sewage Disposal, then heats to 180 DEG C and distill 4 ~ 5 hours under condition of negative pressure, steam
Glycerol, sulfur acid sodium, a small amount of glycerol and a small amount of by-product in bottoms, bottoms enter roaster roasting recycling sulfuric acid
Sodium；Distillation still will be added by the crude product for the 8-hydroxyquinoline being centrifugally separating to obtain, is warming up to 120 DEG C and steams moisture, then control
Vacuum degree is lower than -0.09Mpa in kettle processed, and kettle temperature starts to distill at 160 ~ 180 DEG C, when kettle temperature reaches 200 DEG C or more, distillation
It finishes, collects distillate, residue send to roaster and roasts recycling sodium sulphate；It will be carried out after the distillate import slices machine of collection cold
But, it and is sliced, packs, obtain finished product 8-hydroxyquinoline.
Claims (5)
1. a kind of preparation method of the 8-hydroxyquinoline of no solid waste output, which is characterized in that by glycerol under sulfuric acid dehydration
Methacrylaldehyde is formed, methacrylaldehyde reacts cyclic condensation with o-aminophenol, then is dehydrated into 8-hydroxyquinoline through o-nitrophenol oxidation
Semi-finished product, and neutralized the sulfuric acid in semi-finished product with liquid alkaline, then 8-hydroxyquinoline crude product is obtained after centrifuge is separated by solid-liquid separation,
Crude product is distilled, is sliced to obtain 8-hydroxyquinoline.
2. the preparation method of the 8-hydroxyquinoline according to claim 1 without solid waste output, which is characterized in that the glycerol,
Sulfuric acid, o-nitrophenol, o-aminophenol, liquid alkaline and water mass ratio be 10 ~ 15:14 ~ 20:2 ~ 5:4 ~ 8:35 ~ 40:1 ~ 2.
3. the preparation method of the 8-hydroxyquinoline of no solid waste output according to claim 1 or claim 2, which is characterized in that the liquid
The content of sodium hydroxide is 30wt% in alkali.
4. the preparation method of the 8-hydroxyquinoline according to claim 3 without solid waste output, which is characterized in that including following step
It is rapid:
(1) stand-by by formula measurement glycerol, sulfuric acid, o-nitrophenol, o-aminophenol, liquid alkaline and water；
(2) it is condensed: reaction kettle is added in glycerol, the sulfuric acid of formula sulfuric acid total weight 50 ~ 55% is added dropwise, and controls temperature in the kettle and exists
60 DEG C hereinafter, drop acid after stir 15 ~ 20 minutes, then sequentially add o-aminophenol, o-nitrophenol, continue control kettle
It below interior temperature 60 C and stirs 30 ~ 40 minutes, reaction kettle is heated, when temperature in the kettle rises to 130 ~ 135 DEG C, be added dropwise
Residual sulfuric acid simultaneously controls 135 ~ 140 DEG C of temperature, keeps the temperature 2 ~ 3 hours for 135 ~ 140 DEG C of temperature of control after the concentrated sulfuric acid is added dropwise, heat preservation
After material in kettle is cooled to 100 DEG C, into reaction kettle plus water management temperature that remaining unreacted is steamed no more than 125 DEG C is adjacent
Temperature in the kettle is cooled to 100 DEG C or less after distillation by nitrophenol；
(3) it neutralizes: liquid alkaline being slowly added dropwise into reaction kettle, and controls temperature 60 C hereinafter, when pH value reaches 6.5 ~ 7.0 in kettle
Stop that liquid alkaline is added dropwise, by being centrifugally separating to obtain the crude product and centrifuge mother liquor of solid 8-hydroxyquinoline, aqueous, sulphur in centrifuge mother liquor
Sour sodium, glycerol and a small amount of by-product；
(4) MVR evaporates: after MVR is concentrated by evaporation, sodium sulphate is precipitated centrifuge mother liquor with crystal form, is centrifugated out sodium sulphate,
And mainly contain glycerol, Shao Liangshui, sodium sulphate and reaction by-product in residual mother liquor；
(5) glycerol recycles: residual mother liquor squeezes into glycerol distillation kettle with dehvery pump, is warming up to 100 DEG C and distills 2 ~ 3 under condition of negative pressure
Hour, the waste water steamed is delivered to Sewage Disposal, then heats to 180 DEG C and distill 4 ~ 5 hours under condition of negative pressure, steam
Glycerol, sulfur acid sodium, a small amount of glycerol and a small amount of by-product in bottoms,
Bottoms enter roaster roasting recycling sodium sulphate；
(6) it distills: distillation still will be added by the crude product for the 8-hydroxyquinoline being centrifugally separating to obtain, be warming up to 120 DEG C and steam water
Point, then control vacuum degree in kettle and be lower than -0.09Mpa, kettle temperature starts to distill at 160 ~ 180 DEG C, when kettle temperature reach 200 DEG C with
When upper, distillation is finished, and collects distillate, and residue send to roaster and roasts recycling sodium sulphate；
(7) it is sliced, packs: will be cooled down after the distillate import slices machine of collection, and be sliced, pack, obtain finished product 8- hydroxyl
Base quinoline.
5. the preparation method of the 8-hydroxyquinoline according to claim 4 without solid waste output, which is characterized in that the step
(4), water obtained by step (5) is back to step (3) and carries out neutralization reaction.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115181064A (en) * | 2022-08-22 | 2022-10-14 | 生工生物工程（上海）股份有限公司 | Purification method of 8-hydroxyquinoline |
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| CN115181064A (en) * | 2022-08-22 | 2022-10-14 | 生工生物工程（上海）股份有限公司 | Purification method of 8-hydroxyquinoline |
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