CN109796392A - A kind of methyl ethyl ketone peroxide synthetic method that no three wastes generates - Google Patents
A kind of methyl ethyl ketone peroxide synthetic method that no three wastes generates Download PDFInfo
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Abstract
The present invention provides the methyl ethyl ketone peroxide synthetic methods that a kind of no three wastes generates.The technical solution makees solvent using repefral using hydrogen peroxide, butanone as raw material, is reacted by the anti-method for dripping butanone, after completion of the reaction, hydrophilic solvent is added again thereto, to realize that product liquid is homogeneous.This method has been broken in prior synthesizing method, it is necessary to first mix butanone and solvent, acidic catalyst is added, the technology prejudice of dripping hydrogen peroxide utilizes the acidity of hydrogen peroxide using using hydrogen peroxide as bottom material, the method being voluntarily catalyzed, this method do raw material with butanone without adding other acid, repefral makees solvent, after completion of the reaction, without dividing water, quantitative a kind of solvent is added into system, stabilizer blend is added, after mixing evenly.Reaction process of the present invention is very steady, and the synthesis process of product is generated without any three wastes, and products obtained therefrom has extremely good stability and good service performance.
Description
Technical field
The present invention relates to technical field of chemical engineering, and in particular to a kind of methyl ethyl ketone peroxide synthesis side that no three wastes generates
Method.
Background technique
Methyl ethyl ketone peroxide is the initiator of unsaturated polyester resin, has important shadow to the performance of unsaturated polyester resin
It rings.Unsaturated polyester resin is a kind of important high molecular material, and yield is other in megaton, and application range is extremely wide, including flies
More than ten of field such as machine, high-speed rail, ship, yacht, wind-power electricity generation, reinforced plastics, the conjunction of unsaturated polyester resin material
At being all to make initiator with methyl ethyl ketone peroxide wherein there is 90% or more kind, it can be seen that, PET industry is to peroxidating first
The demand of ethyl ketone product is not only very big, but also dependence is also very strong.
The traditional synthetic method of methyl ethyl ketone peroxide is passed through in the presence of solvent and acidic catalyst with butanone
The mode that hydrogen peroxide is added dropwise is synthesized, and there are many report of forefathers' this respect, only in terms of patent, German patent DE 4438147
(1994), DE1243195, hungarian patent HU.197707B, PCT Patent WO0009478 (2000), Japan Patent JP45-
19486 (1970), Chinese patent CN107999011A (2018), CN105237453A (2015) be all in this way, and
Chinese patent CN18000161A is still under conditions of acid is added being catalyzed although going forward side by side mode using double fluid
It is reacted, in this way, waste water still will generate, which is to solve the problems, such as the serialization of product synthesis.
Methyl ethyl ketone peroxide synthesis process addition acid carries out catalysis, and there are drawbacks, because under normal conditions, using
Acid, including sulfuric acid, nitric acid, trichloroacetic acid etc., sulfate radical, nitrate anion, the chloride ion etc. that these catalyst introduce, all can be serious
Influence methyl ethyl ketone peroxide product stability, so, after reaction, it usually needs product is layered, thus by these from
Son is molten to be separated together with water in water, in this way, synthesis process just generates a certain amount of waste water, these waste water generally contained
Oxide weight ratio 20% or so (in terms of hydrogen peroxide), because wherein containing the peroxides such as chloride ion, sulfate ion, nitrate ion
The sensible factor of compound, thus it is abnormally dangerous, it is reported that, in the safety accident of methyl ethyl ketone peroxide manufacturing enterprise, wastewater treatment
Caused explosion, ratio are very high.
The self stability of methyl ethyl ketone peroxide product is also a critically important problem, the mode of butanone is added dropwise, because of body
There is a large amount of hydrogen peroxide always in system, so, the component ratio of products obtained therefrom, there is very with hydrogen peroxide process is added dropwise
Big difference, the product form that this method generates, stability, which is apparently higher than, is added dropwise hydrogen peroxide process, this is in embodiment
Testing result in, embodiment is very the meaning it will be evident that this point, it be not only improve product Storage period and usability
Can, it is often more important that, if fruit product is unstable, product can gradually react again after decomposition, generate it is a kind of to vibration, it is friction, ultraviolet
The all very sensitive new peroxide such as light, this compound can be precipitated from product in low temperature, be formed and be crystallized, in product
Once there are a large amount of compounds, just it is easy to cause explosion, and we are using the scheme that butanone is added dropwise, and effectively solve
Product stability problems.
In environmental protection, in recent years, as Environmental requires continuing to increase for dynamics, methyl ethyl ketone peroxide product is closed
It at the wastewater problem of process, more highlights, traditional synthesis technology, synthesis process necessarily leads to waste water, although this effluent part
Amount is little, but content of organics (COD) is very high and extremely unstable, will have a large amount of oxygen to escape under room temperature, and simultaneous is put
Heat is just probably exploded after temperature reaches self-heating temperature, although these wastewater flow rates less, deal with difficulty
It is really not small, in recent years, it is directed to waste water stability problem, be born resin catalysis, although this method relieves drawing for ion
Enter problem, but the recovery processing process of resin is not only complicated, but also cost is also relatively high, so that product ton consumption obviously increases.It is comprehensive
It is upper described, seek a kind of neither generation waste water, while product has the methyl ethyl ketone peroxide synthetic method of good service performance again,
It is of great significance.
Summary of the invention
The present invention is directed to be directed to the technological deficiency of the prior art, a kind of methyl ethyl ketone peroxide synthesis that no three wastes generates is provided
Method, to solve the technical issues of conventional synthesis process of methyl ethyl ketone peroxide can generate the three wastes.
Another technical problem to be solved by the present invention is that its stability of methyl ethyl ketone peroxide synthesized by conventional method needs
Improve.
To realize the above technical purpose, the invention adopts the following technical scheme:
The methyl ethyl ketone peroxide synthetic method that a kind of no three wastes generates, comprising the following steps: by the hydrogen peroxide of formula ratio and
Repefral is added to the container, and butanone is persistently added dropwise thereto under agitation, until end of reaction.This method
First hydrogen peroxide and repefral are added in reaction vessel, butanone is added dropwise under agitation, is begun with guarantee system
It is in suitable acid range catalytic condition eventually.
Preferably, system temperature is 0~40 DEG C during the dropwise addition；It is further preferred that system temperature is
20~40 DEG C.
Preferably, the molar ratio of dioxygen water consumption and butanone dosage is 1.6~2.1:1；It is further preferred that hydrogen peroxide
The molar ratio of dosage and butanone dosage is 1.8~1.9:1.
Preferably, the duration of the dropwise addition is 0.5~3h；It is further preferred that the duration of the dropwise addition
For 1.5~2.5h.
Preferably, after completion of the reaction, hydrophilic solvent is added to reaction system.
Preferably, after completion of the reaction, hydrophilic solvent and product stabilizer, stirring, until product is added to reaction system
Stabilizer dissolution.
Preferably, the hydrophilic solvent includes ethylene glycol, diethylene glycol or glycerine.
A kind of synthesis for the methyl ethyl ketone peroxide product that stable and synthesis process no three wastes generates the present invention provides product
Method.The technical solution makees solvent using repefral using hydrogen peroxide, butanone as raw material, passes through the anti-butanone that drips
Method is reacted, and after completion of the reaction, hydrophilic solvent is added again thereto, to realize that product liquid is homogeneous.This method
Break in prior synthesizing method, it is necessary to first butanone and solvent be mixed, acidic catalyst, the skill of dripping hydrogen peroxide is added
Art prejudice, using using hydrogen peroxide as bottom material, using the acidity of hydrogen peroxide, the method being voluntarily catalyzed, this method is without adding
Other acid do raw material with butanone, and repefral makees solvent, and after completion of the reaction, without dividing water, it is fixed to add into system
A kind of solvent of amount, adds stabilizer blend, after mixing evenly.
Be compared with the traditional method compared with technical advantage of the invention embodies a concentrated reflection of in the following areas: 1, reaction process is very flat
Surely, synthesis process safety is improved.2, the synthesis process of product is generated without any three wastes, that is, solves the problems, such as the three wastes, together
When, and relieve the unstability bring security risk of waste water.3, product service performance is good.4, the production synthesized with this method
Product, stability have exceeded currently reported similar product.In conclusion the present invention devises a completely new synthesis road
The product of line, route synthesis effectively prevents the generation of the three wastes under the premise of guaranteeing products application performance, meanwhile, product
Stability be also greatly improved, product storage experiment in, the stability of the technique sintetics has reached
The best level of similar products at home and abroad.
Specific embodiment
Below by specific embodiments of the present invention will be described in detail.In order to avoid excessive unnecessary details,
It will not be described in detail in following embodiment to belonging to well known structure or function.Approximation used in following embodiment
Language can be used for quantitative expression, show to allow quantity to have certain variation in the case where not changing basic function.It is fixed except having
Adopted outer, technical and scientific term used in following embodiment has the phase being commonly understood by with those skilled in the art of the invention
Same meaning.
Embodiment 1
Be equipped with stirring, thermometer, dropping funel 250ml four-hole bottle in, be added sequentially into 90g (1.323mol)
50% hydrogen peroxide, the repefral of 15.0g 99.5%, finishes, and starts stirring, under agitation, passes through outside
Temperature of reaction system is controlled at 20-22 DEG C, then by dropping funel, 50.5g is slowly added dropwise into system by water bath with thermostatic control
The butanone of (0.700mol), time for adding maintain 2.0h or so, after being added dropwise, continue to be stirred to react 1.0h in this temperature,
After completion of the reaction, under agitation, diethylene glycol 45g, product stabilizer 0.004g is added to system, continues 10 points of stirring
Clock obtains product 200g, active o content 9.81% until stabilizer is completely dissolved.
Embodiment 2
Be equipped with stirring, thermometer, dropping funel 250ml four-hole bottle in, be added sequentially 15.0g's 99.5%
Repefral, the butanone of 50.5g (0.700mol), finishes, and starts stirring, under agitation, instills to system
The nitric acid of 0.3g 60-65% controls temperature of reaction system at 20-22 DEG C then by external water bath with thermostatic control, then passes through drop
Liquid funnel, 50% hydrogen peroxide of 90g (1.323mol) is slowly added dropwise into system, and time for adding maintains 2.0h or so, drips
Bi Hou continues to be stirred to react 1.0h in this temperature, then stops stirring, and heat preservation stands 0.5h, separates moisture about 33.0g, divide water
After, stirring is started again, under agitation, diethylene glycol 50.0g, product stabilizer 0.004g is added to system,
Continuous stirring 10 minutes, until stabilizer is completely dissolved, obtains product volume 172.8g, active o content 9.82%.
Embodiment 3
Be equipped with stirring, thermometer, dropping funel 250ml four-hole bottle in, be added sequentially 15.0g's 99.5%
Repefral, the butanone of 50.5g (0.700mol), finishes, and starts stirring, under agitation, instills 0.3g
The sulfuric acid of 95-98% controls temperature of reaction system at 20-22 DEG C then by external water bath with thermostatic control, then is leaked by dropping liquid
Bucket, 50% hydrogen peroxide of 90g (1.323mol) is slowly added dropwise into system, and time for adding maintains 2.0h or so, after being added dropwise,
Continue to be stirred to react 1.0h in this temperature, then stop stirring, heat preservation stands 0.5h and separates moisture until system layering is clear
37.0g starts stirring again, under agitation, diethylene glycol 54.0g, product stabilizer 0.004g is added to system, continues
Stirring 10 minutes, until stabilizer is completely dissolved, obtains product 172.3g, active o content 9.82%.
Embodiment 4
Be equipped with stirring, thermometer, dropping funel 250ml four-hole bottle in, be added sequentially 15.0g's 99.5%
Repefral, the butanone of 50.5g (0.700mol), finishes, and starts stirring, under agitation, 0.5g is added
99% trichloroacetic acid controls temperature of reaction system at 20-22 DEG C then by external water bath with thermostatic control, then passes through dropping funel,
50% hydrogen peroxide of 90g (1.323mol) is slowly added dropwise into system, time for adding maintains 2.0h or so, after being added dropwise, in
This temperature continues to be stirred to react 1.0h, then stops stirring, and heat preservation stands 0.5h, separates moisture content 27.0g, start stirring again,
Under agitation, diethylene glycol 49.0g, product stabilizer 0.004g is added to system, continues stirring 10 minutes, until stabilizer
It is completely dissolved, obtains product 177.5g, active o content 9.80%.
Embodiment 5
Be equipped with stirring, thermometer, dropping funel 250ml four-hole bottle in, be added sequentially into 90g (1.323mol)
50% hydrogen peroxide, the repefral of 15.0g 99.5%, finishes, and starts stirring, under agitation, passes through outside
Temperature of reaction system is controlled at 20-22 DEG C, then by dropping funel, 50.5g is slowly added dropwise into system by water bath with thermostatic control
The butanone of (0.700mol), time for adding maintain 2.0h or so, after being added dropwise, continue to be stirred to react 1.0h in this temperature,
After completion of the reaction, under agitation, solvent ethylene glycol 45g, product stabilizer 0.004g is added to system, continues 10 points of stirring
Clock, until stabilizer is completely dissolved, discharging obtains product 200g, active o content 9.82%.
Embodiment 6
Be equipped with stirring, thermometer, dropping funel 250ml four-hole bottle in, be added sequentially into 90g (1.323mol)
50% hydrogen peroxide, the repefral of 15.0g 99.5%, finishes, and starts stirring, under agitation, passes through outside
Temperature of reaction system is controlled at 20-22 DEG C, then by dropping funel, 50.5g is slowly added dropwise into system by water bath with thermostatic control
The butanone of (0.700mol), time for adding maintain 2.0h or so, after being added dropwise, continue to be stirred to react 1.0h in this temperature,
After completion of the reaction, under agitation, glycerine 45g, product stabilizer 0.004g is added to system, continues stirring 10 minutes, until
Stabilizer is completely dissolved, product 200g, active o content 9.81%.
Embodiment 7
Be equipped with stirring, thermometer, dropping funel 250ml four-hole bottle in, be added sequentially into 90g (1.323mol)
50% hydrogen peroxide, the repefral of 15.0g 99.5%, finishes, and starts stirring, under agitation, passes through outside
Ice-water bath is cooling, and temperature of reaction system is reduced to 0-5 DEG C, and then by dropping funel, 50.5g is slowly added dropwise into system
The butanone of (0.700mol), time for adding maintain 2.0h or so, and during which temperature is maintained not higher than 5 DEG C, after being added dropwise, remove
Fall water bath with thermostatic control, reaction system is gradually warmed up to 30 DEG C, and it is anti-that system temperature is then maintained 33-35 DEG C of heat preservation with water bath with thermostatic control
1.0h is answered, after completion of the reaction, under agitation, diethylene glycol 45g, product stabilizer 0.004g is added to system, it is continuous to stir
It mixes 10 minutes, until stabilizer is completely dissolved, product 200g is obtained, active o content 9.81% is tested.
Embodiment 8
Be equipped with stirring, thermometer, dropping funel 250ml four-hole bottle in, be added sequentially into 90g (1.323mol)
50% hydrogen peroxide, the repefral of 15.0g 99.5%, finishes, and starts stirring, under agitation, passes through outside
Temperature of reaction system is controlled at 30-32 DEG C, then by dropping funel, 50.5g is slowly added dropwise into system by water bath with thermostatic control
The butanone of (0.700mol), time for adding maintain 2.0h or so, and during which temperature maintains between 30-35 DEG C, after being added dropwise,
With water bath with thermostatic control, system temperature is maintained 33-35 DEG C, and in this insulation reaction 1.0h, after completion of the reaction, in stirring condition
Under, diethylene glycol 45g, product stabilizer 0.004g is added to system, continues stirring 10 minutes, until stabilizer is completely dissolved, stops
It only stirs, discharges, obtain product 200g, test product active o content 9.80%.
Embodiment 9
Be equipped with stirring, thermometer, dropping funel 250ml four-hole bottle in, be added sequentially 100g (1.471mol)
50% hydrogen peroxide, the repefral of 15.0g 99.5%, finishes, and starts stirring, under agitation, passes through outside
Temperature of reaction system is controlled at 20-22 DEG C, then by dropping funel, 50.5g is slowly added dropwise into system by water bath with thermostatic control
The butanone of (0.700mol), time for adding maintain 2.0h or so, and after being added dropwise, with water bath with thermostatic control, system temperature is maintained
Insulation reaction 1.0h is kept the temperature at 20-22 DEG C, and in this, after completion of the reaction, under agitation, diethylene glycol is added to system
35g, product stabilizer 0.004g continue stirring 10 minutes, until stabilizer is completely dissolved, obtain product 200g, active o content
11.01%.
Embodiment 10
Be equipped with stirring, thermometer, dropping funel 250ml four-hole bottle in, be added sequentially 80g (1.176mol)
50% hydrogen peroxide, the repefral of 15.0g 99.5%, finishes, and starts stirring, under agitation, passes through outside
Temperature of reaction system is controlled at 20-22 DEG C, then by dropping funel, 50.5g is slowly added dropwise into system by water bath with thermostatic control
The butanone of (0.700mol), time for adding maintain 2.0h or so, and after being added dropwise, with water bath with thermostatic control, system temperature is maintained
Insulation reaction 1.0h is kept the temperature at 20-22 DEG C, and in this, after completion of the reaction, under agitation, diethylene glycol is added to system
55g, product stabilizer 0.004g continue stirring 10 minutes, until stabilizer is completely dissolved, obtain product 200g, active o content
9.103%.
Embodiment 11
The present embodiment is used to investigate waste water yield, product stability and the properties of product of above embodiments 1~10.
The waste water yield of product per ton under the different catalytic conditions of table 1
The stability of product is produced under the conditions of table 2 is each
The performance indicator of each embodiment products obtained therefrom is detected below by way of experimental method: resin used in testing is Shandong
196 resins of Hong Xin Chemical Co., Ltd. production, promotor use the high rush 1 that the applicant produces, moisture recorder
The R1001 type moisture recorder for using Hangzhou Mei Kong Autotek S. r. l. to produce, 25 DEG C of environment temperature.Experiment knot
Fruit is as shown in the following Table 3.
3 product performance index of table
By the above experimental data it can be found that three-waste free discharge may be implemented in the technique, achieve the purpose that purification production.And
And sintetics is reacted under hydrogen peroxide itself acidic catalyst, because introducing without other ions, the stability of product can reach
To ideal result.Meanwhile the product of hydrogen peroxide self-catalysis synthesis, when causing 196 resin, thermal discharge, which is apparently higher than, to be made
Cause thermal discharge with other acidic catalyst sinteticses.
The embodiments of the present invention have been described in detail above, but content is only the preferred embodiment of the present invention,
It is not intended to limit the invention.All any modifications, equivalent replacements, and improvements etc. done in application range of the invention, should all
It is included within protection scope of the present invention.
Claims (10)
1. the methyl ethyl ketone peroxide synthetic method that a kind of no three wastes generates, it is characterised in that the following steps are included: by formula ratio
Hydrogen peroxide and repefral are added to the container, and butanone is persistently added dropwise thereto under agitation, until having reacted
Finish.
2. the methyl ethyl ketone peroxide synthetic method that a kind of no three wastes according to claim 1 generates, it is characterised in that in institute
During stating dropwise addition, system temperature is 0~40 DEG C.
3. the methyl ethyl ketone peroxide synthetic method that a kind of no three wastes according to claim 2 generates, it is characterised in that in institute
During stating dropwise addition, system temperature is 20~40 DEG C.
4. the methyl ethyl ketone peroxide synthetic method that a kind of no three wastes according to claim 1 generates, it is characterised in that dioxygen
The molar ratio of water consumption and butanone dosage is 1.6~2.1:1.
5. the methyl ethyl ketone peroxide synthetic method that a kind of no three wastes according to claim 4 generates, it is characterised in that dioxygen
The molar ratio of water consumption and butanone dosage is 1.8~1.9:1.
6. the methyl ethyl ketone peroxide synthetic method that a kind of no three wastes according to claim 1 generates, it is characterised in that described
The duration of dropwise addition is 0.5~3h.
7. the methyl ethyl ketone peroxide synthetic method that a kind of no three wastes according to claim 6 generates, it is characterised in that described
The duration of dropwise addition is 1.5~2.5h.
8. the methyl ethyl ketone peroxide synthetic method that a kind of no three wastes according to claim 1 generates, which is characterized in that reaction
After, hydrophilic solvent is added to reaction system.
9. the methyl ethyl ketone peroxide synthetic method that a kind of no three wastes according to claim 1 generates, which is characterized in that reaction
After, hydrophilic solvent and product stabilizer, stirring is added to reaction system, until product stabilizer dissolves.
10. the methyl ethyl ketone peroxide synthetic method that a kind of no three wastes according to claim 8 or claim 9 generates, it is characterised in that
The hydrophilic solvent includes ethylene glycol, diethylene glycol or glycerine.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114560798A (en) * | 2022-03-16 | 2022-05-31 | 江门市加滢精细化工有限公司 | Preparation method of methyl ethyl ketone peroxide |
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| WO1996012698A1 (en) * | 1994-10-25 | 1996-05-02 | Peroxid-Chemie Gmbh | Production of salt-free and low-water-content methyl ethyl ketone peroxide |
| CN1800161A (en) * | 2006-01-16 | 2006-07-12 | 华东理工大学 | Method and microreaction device for continuous producing garox mek |
| CN105237453A (en) * | 2015-09-25 | 2016-01-13 | 西北师范大学 | Method used for preparing methylethyl ketone peroxide by taking acidic ion exchange resin as catalyst |
| CN107999011A (en) * | 2017-12-13 | 2018-05-08 | 方亨 | Methyl ethyl ketone peroxide production system and production technology |
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2019
- 2019-03-28 CN CN201910240189.4A patent/CN109796392B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996012698A1 (en) * | 1994-10-25 | 1996-05-02 | Peroxid-Chemie Gmbh | Production of salt-free and low-water-content methyl ethyl ketone peroxide |
| CN1800161A (en) * | 2006-01-16 | 2006-07-12 | 华东理工大学 | Method and microreaction device for continuous producing garox mek |
| CN105237453A (en) * | 2015-09-25 | 2016-01-13 | 西北师范大学 | Method used for preparing methylethyl ketone peroxide by taking acidic ion exchange resin as catalyst |
| CN107999011A (en) * | 2017-12-13 | 2018-05-08 | 方亨 | Methyl ethyl ketone peroxide production system and production technology |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114560798A (en) * | 2022-03-16 | 2022-05-31 | 江门市加滢精细化工有限公司 | Preparation method of methyl ethyl ketone peroxide |
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