CN108610273A - A kind of method of purification of peroxidized t-butyl perbenzoate - Google Patents
A kind of method of purification of peroxidized t-butyl perbenzoate Download PDFInfo
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- CN108610273A CN108610273A CN201810607657.2A CN201810607657A CN108610273A CN 108610273 A CN108610273 A CN 108610273A CN 201810607657 A CN201810607657 A CN 201810607657A CN 108610273 A CN108610273 A CN 108610273A
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- peroxidized
- butyl perbenzoate
- butyl
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- redox reaction
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
Abstract
The present invention provides a kind of methods of purification of peroxidized t-butyl perbenzoate, and peroxidized t-butyl perbenzoate crude product is mixed with sodium sulfide solution, carry out redox reaction, obtain peroxidized t-butyl perbenzoate；The peroxidized t-butyl perbenzoate crude product includes peroxidized t-butyl perbenzoate and tert-butyl hydroperoxide.The residual quantity of tert-butyl hydroperoxide is only 0.05~0.1% in the peroxidized t-butyl perbenzoate that the method for purification of the present invention obtains, washing methods relative to existing peroxidized t-butyl perbenzoate (residual quantity of tert-butyl hydroperoxide is 1~2%), the method of purification of peroxidized t-butyl perbenzoate provided by the invention significantly reduces the residual quantity of tert-butyl hydroperoxide, improves the purity of peroxidized t-butyl perbenzoate.
Description
Technical field
The present invention relates to peroxide post-processing technology field more particularly to a kind of purifications of peroxidized t-butyl perbenzoate
Method.
Background technology
Peroxidized t-butyl perbenzoate (abbreviation TBPB or CP-02) is a kind of colourless to yellowish liquid, slightly aroma
Taste, it is not soluble in water, organic solvent can be dissolved in.In ethylene, styrene, propylene, vinyl acetate, diallyl phthalate and different
In the polymerization processes such as butylene, peroxidized t-butyl perbenzoate is widely used as initiator；During curable unsaturated polyester, quilt
Such as SMC, BMC, DMC is widely used in draw in agent moulding process；It is also possible to higher such as MEPK, BPO with some activity
Or TBPO etc. forms bi-component curing system application.
Currently, with sulfuric acid or other acid for catalyst, using hydrogen peroxide as oxidant, catalytic oxidation of tert-butanol prepares tertiary butyl
Hydrogen peroxide, then reacted with hydroxide (the common sodium hydroxide or potassium hydroxide) aqueous solution and chlorobenzoyl chloride of alkali metal
Peroxidized t-butyl perbenzoate is synthesized, is most common process route.Chinese patent CN 1763001A disclose a kind of peroxidating
The production technology of t-butyl perbenzoate, wherein to the post-processing of TBPB crude products washed with liquid caustic soda, it is therein miscellaneous to remove
Matter-tert-butyl hydroperoxide (TBHP).Chinese patent CN 105175303A disclose a kind of peroxidized t-butyl perbenzoate initiation
The preparation process of agent, wherein the washing to TBPB crude products is after being washed with 10% sodium carbonate liquor again with 3% sodium hydroxide and water
It washs respectively.However, both the above is in the method for liquid caustic soda washing TBPB crude products, it is miscellaneous in the TBPB crude products after practice finds washing
The residual quantity of matter tert-butyl hydroperoxide is still 1-2% (mass fraction), has seriously affected peroxidized t-butyl perbenzoate product
Purity.
Therefore, a kind of method of purification of novel peroxidized t-butyl perbenzoate is developed, is had for production application
Important meaning.
Invention content
The purpose of the present invention is to provide a kind of methods of purification of peroxidized t-butyl perbenzoate, reduce perbenzoic acid
The residual quantity of impurity tert-butyl hydroperoxide in tert-butyl ester.
In order to achieve the above-mentioned object of the invention, the present invention provides following technical scheme：
The present invention provides a kind of methods of purification of peroxidized t-butyl perbenzoate, include the following steps：
Peroxidized t-butyl perbenzoate crude product is mixed with sodium sulfide solution, redox reaction is carried out, obtains peroxide
Change t-butyl perbenzoate；The peroxidized t-butyl perbenzoate crude product includes peroxidized t-butyl perbenzoate and t-butyl peroxy
Change hydrogen.
Preferably, the mass fraction of the sodium sulfide solution is 1.0~3.0%.
Preferably, the mass ratio of the peroxidized t-butyl perbenzoate crude product and sodium sulfide solution is 1~2:1.
Preferably, the temperature of the redox reaction is 10~30 DEG C.
Preferably, the time of the redox reaction is 0.5~2h.
Preferably, the redox reaction carries out under conditions of pH value is 8~11.
Preferably, it is acetic acid, sulfuric acid or hydrochloric acid to adjust reagent used by the pH value.
Preferably, the peroxidized t-butyl perbenzoate crude product is using preceding carry out carrying out washing treatment；The carrying out washing treatment institute
The washing reagent used is sodium hydroxide solution.
Preferably, further include after the redox reaction：
Gained system is layered, gained organic phase is isolated, obtains peroxidized t-butyl perbenzoate.
The present invention provides a kind of method of purification of peroxidized t-butyl perbenzoate, the present invention utilizes tert-butyl hydroperoxide
Redox reaction occurs with vulcanized sodium, tert-butyl hydroperoxide is removed from peroxidized t-butyl perbenzoate.The present invention's
The residual quantity of tert-butyl hydroperoxide is only 0.05~0.1% in the peroxidized t-butyl perbenzoate that method of purification obtains, relatively
In the washing methods (residual quantity of tert-butyl hydroperoxide is 1~2%) of existing peroxidized t-butyl perbenzoate, the present invention carries
The method of purification of the peroxidized t-butyl perbenzoate of confession significantly reduces the residual quantity of tert-butyl hydroperoxide, improves peroxidating
The purity of t-butyl perbenzoate.
Specific implementation mode
The present invention provides a kind of methods of purification of peroxidized t-butyl perbenzoate, include the following steps：
Peroxidized t-butyl perbenzoate crude product is mixed with sodium sulfide solution, redox reaction is carried out, obtains peroxide
Change t-butyl perbenzoate；The peroxidized t-butyl perbenzoate crude product includes peroxidized t-butyl perbenzoate and t-butyl peroxy
Change hydrogen.
The present invention does not have special restriction for the source of the peroxidized t-butyl perbenzoate crude product, using this field skill
Source known to art personnel；In an embodiment of the present invention, specifically with sulfuric acid or other acid for catalyst, with hydrogen peroxide
For oxidant, catalytic oxidation of tert-butanol prepares tert-butyl hydroperoxide, then with the hydroxide of alkali metal (common sodium hydroxide or
Potassium hydroxide) aqueous solution and chlorobenzoyl chloride reacted, obtained peroxidized t-butyl perbenzoate crude product.
In the present invention, the peroxidized t-butyl perbenzoate crude product is using preceding preferred carry out carrying out washing treatment；It is described to wash
It is sodium hydroxide solution to wash washing reagent used by processing；The mass concentration of the sodium hydroxide solution is preferably 4.0~
7.0%, more preferably 5.0~6.0%.In the present invention, after washing gained peroxidized t-butyl perbenzoate crude product in tertiary butyl
The mass content of hydrogen peroxide is preferably 1~2%.Present invention preferably employs Shimadzu gas chromatographs to pass through the tertiary fourth of external standard method
The content of base hydrogen peroxide.
In the present invention, the mass fraction of the sodium sulfide solution is preferably 1.0~3.0%, more preferably 1.5~
2.5%.In the present invention, the mass ratio of the peroxidized t-butyl perbenzoate crude product and sodium sulfide solution is preferably 1~2:
1, more preferably 1.2~1.8:1.Using vulcanized sodium and tert-butyl hydroperoxide redox reaction occurs for the present invention, by tertiary fourth
Base hydrogen peroxide is removed from peroxidized t-butyl perbenzoate.The present invention does not have the mode of the mixing special limitation, choosing
It is mixed with mode well known to those skilled in the art, enables to peroxidized t-butyl perbenzoate crude product and vulcanized sodium water-soluble
Liquid uniformly mixes.
In the present invention, the temperature of the redox reaction is preferably 10~30 DEG C, more preferably 15~25 DEG C；It is described
The time of redox reaction is preferably 0.5~2h, more preferably 1.0~1.5h.The present invention is by controlling redox reaction
Temperature and time tert-butyl hydroperoxide can be made fully to be reacted with vulcanized sodium, to reduce tert-butyl hydroperoxide impurity
Content.
In the present invention, the redox reaction preferably carries out under conditions of pH value is 8~11, more preferably 9~
10.The present invention adjusts the acid-base value of solution by control ph.
In the present invention, it is preferably acetic acid, sulfuric acid or hydrochloric acid to adjust reagent used by the pH value.The present invention is using acid
The pH value of class adjustment strong alkali solution can achieve the effect that best.
In the present invention, the redox reaction preferably carries out under agitation, and the speed of the stirring is preferably
50~150rpm, more preferably 80~120rpm.
In the present invention, further include after the redox reaction：
Gained system is layered, gained organic phase is isolated, obtains peroxidized t-butyl perbenzoate.
The present invention does not have the mode of the layering special limitation, and mode well known to those skilled in the art is selected to carry out
Layering is specifically as follows stratification in an embodiment of the present invention.The present invention is not special to the mode of the separation
Limitation, select mode well known to those skilled in the art to be detached, organic phase can be isolated.
The method of purification of peroxidized t-butyl perbenzoate provided by the invention is carried out specifically with reference to embodiment
It is bright, but they cannot be interpreted as limiting the scope of the present invention.
Embodiment 1
200g peroxidized t-butyl perbenzoate crude products are weighed, use mass concentration to be washed for 5.5% sodium hydroxide, control
Temperature is 25 DEG C, and 100g 2.0% (mass fraction) sodium sulfide solution is added, and it is 8.0 that salt acid for adjusting pH value, which is added, is being stirred
Under the conditions of (rotating speed 100rpm) carry out redox reaction 1.5h, stratification isolates organic phase, and gained organic phase is taken to survey
The content of fixed wherein tert-butyl hydroperoxide, the content for measuring t-butyl hydroperoxide are 0.050% (mass fraction).
Embodiment 2
200g peroxidized t-butyl perbenzoate crude products are weighed, use mass concentration to be washed for 5.5% sodium hydroxide, control
Temperature is 25 DEG C, and 100g 2.0% (mass fraction) sodium sulfide solution is added, and it is 9.0 that sulphur acid for adjusting pH value, which is added, is being stirred
Under the conditions of (rotating speed 100rpm) carry out redox reaction 1.5h, stratification isolates organic phase, and gained organic phase is taken to survey
The content of fixed wherein tert-butyl hydroperoxide, the content for measuring t-butyl hydroperoxide are 0.067% (mass fraction).
Embodiment 3
200g peroxidized t-butyl perbenzoate crude products are weighed, use mass concentration to be washed for 5.5% sodium hydroxide, control
Temperature is 25 DEG C, and 100g 2.0% (mass fraction) sodium sulfide solution is added, and it is 10.0 that sulphur acid for adjusting pH, which is added, in stirring bar
(rotating speed 100rpm) carries out redox reaction 1.5h under part, and stratification isolates organic phase, and gained organic phase is taken to measure
The wherein content of tert-butyl hydroperoxide, the content for measuring t-butyl hydroperoxide are 0.080% (mass fraction).
Embodiment 4
200g peroxidized t-butyl perbenzoate crude products are weighed, use mass concentration to be washed for 5.5% sodium hydroxide, control
Temperature is 25 DEG C, and 100g 2.0% (mass fraction) sodium sulfide solution is added, and it is 11.0 that second acid for adjusting pH, which is added, in stirring bar
(rotating speed 100rpm) carries out redox reaction 1.5h under part, and stratification isolates organic phase, and gained organic phase is taken to measure
The wherein content of tert-butyl hydroperoxide, the content for measuring t-butyl hydroperoxide are 0.10% (mass fraction).
Embodiment 5
200g peroxidized t-butyl perbenzoate crude products are weighed, use mass concentration to be washed for 5.5% sodium hydroxide, control
Temperature is 20 DEG C, and 100g 2.0% (mass fraction) sodium sulfide solution is added, and it is 8.0 that salt acid for adjusting pH, which is added, in stirring bar
(rotating speed 100rpm) carries out redox reaction 1.5h under part, and stratification isolates organic phase, and gained organic phase is taken to measure
The wherein content of tert-butyl hydroperoxide, the content for measuring t-butyl hydroperoxide are 0.055% (mass fraction).
As seen from the above embodiment, the present invention provides a kind of method of purification of peroxidized t-butyl perbenzoate, purification sides
The residual quantity of tert-butyl hydroperoxide is only 0.05~0.1% in the peroxidized t-butyl perbenzoate that method obtains, relative to existing
Peroxidized t-butyl perbenzoate washing methods (residual quantity of tert-butyl hydroperoxide be 1~2%), mistake provided by the invention
The method of purification of oxidation t-butyl perbenzoate significantly reduces the residual quantity of tert-butyl hydroperoxide, improves perbenzoic acid
The purity of the tert-butyl ester.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (9)
1. a kind of method of purification of peroxidized t-butyl perbenzoate, includes the following steps：
Peroxidized t-butyl perbenzoate crude product is mixed with sodium sulfide solution, redox reaction is carried out, obtains benzoyl peroxide
T-butyl formate；The peroxidized t-butyl perbenzoate crude product includes peroxidized t-butyl perbenzoate and tert-butyl hydroperoxide
Hydrogen.
2. method of purification according to claim 1, which is characterized in that the mass fraction of the sodium sulfide solution is 1.0
~3.0%.
3. method of purification according to claim 2, which is characterized in that the peroxidized t-butyl perbenzoate crude product and vulcanization
The mass ratio of sodium water solution is 1~2:1.
4. method of purification according to claim 1, which is characterized in that the temperature of the redox reaction is 10~30
℃。
5. method of purification according to claim 1 or 4, which is characterized in that the time of the redox reaction be 0.5~
2h。
6. method of purification according to claim 1, which is characterized in that the redox reaction is 8~11 in pH value
Under the conditions of carry out.
7. method of purification according to claim 6, which is characterized in that adjust reagent used by the pH value be acetic acid,
Sulfuric acid or hydrochloric acid.
8. method of purification according to claim 1, which is characterized in that the peroxidized t-butyl perbenzoate crude product is using
Preceding carry out carrying out washing treatment；Washing reagent used by the carrying out washing treatment is sodium hydroxide solution.
9. method of purification according to claim 1, which is characterized in that further include after the redox reaction：
Gained system is layered, gained organic phase is isolated, obtains peroxidized t-butyl perbenzoate.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110146608A (en) * | 2019-05-06 | 2019-08-20 | 北京水木滨华科技有限公司 | The quantitative detecting method of each component in system containing water-soluble peroxide |
| CN115650891A (en) * | 2022-10-27 | 2023-01-31 | 常熟市滨江化工有限公司 | Method for purifying tert-butyl peroxybenzoate by using microchannel reactor |
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| CN101631772A (en) * | 2006-07-12 | 2010-01-20 | 联合引发剂有限责任两合公司 | Method for producing acyl peroxides |
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| CN115650891A (en) * | 2022-10-27 | 2023-01-31 | 常熟市滨江化工有限公司 | Method for purifying tert-butyl peroxybenzoate by using microchannel reactor |
| CN115650891B (en) * | 2022-10-27 | 2024-05-03 | 常熟市滨江化工有限公司 | Method for purifying tert-butyl peroxybenzoate by using microchannel reactor |
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