CN116640472A - Production process of cyclohexanone peroxide transparent liquid with stable 50% content - Google Patents
Production process of cyclohexanone peroxide transparent liquid with stable 50% content Download PDFInfo
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- CN116640472A CN116640472A CN202310513600.7A CN202310513600A CN116640472A CN 116640472 A CN116640472 A CN 116640472A CN 202310513600 A CN202310513600 A CN 202310513600A CN 116640472 A CN116640472 A CN 116640472A
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- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 title claims abstract description 107
- 239000007788 liquid Substances 0.000 title claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 239000000243 solution Substances 0.000 claims abstract description 142
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 56
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 40
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 35
- 238000003756 stirring Methods 0.000 claims abstract description 22
- 239000011259 mixed solution Substances 0.000 claims abstract description 21
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims abstract description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 9
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 9
- -1 phthalic acid ester Chemical class 0.000 claims abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 48
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 34
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 18
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 16
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 claims description 16
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims description 12
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 claims description 8
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 claims description 8
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 8
- 238000007599 discharging Methods 0.000 claims description 8
- 238000012544 monitoring process Methods 0.000 claims description 8
- 230000001105 regulatory effect Effects 0.000 claims description 8
- 239000002351 wastewater Substances 0.000 claims description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 7
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 claims description 6
- 229960001826 dimethylphthalate Drugs 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- 230000018044 dehydration Effects 0.000 abstract description 3
- 238000006297 dehydration reaction Methods 0.000 abstract description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract description 3
- 238000005185 salting out Methods 0.000 abstract description 3
- 230000001276 controlling effect Effects 0.000 description 25
- QOSATHPSBFQAML-UHFFFAOYSA-N hydrogen peroxide;hydrate Chemical compound O.OO QOSATHPSBFQAML-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 238000010276 construction Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920006337 unsaturated polyester resin Polymers 0.000 description 3
- 238000000889 atomisation Methods 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
- C07C407/006—Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/34—Filling pastes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a production process of a transparent liquid of cyclohexanone peroxide with stable content of 50%, belonging to the technical field of cyclohexanone peroxide production. Dissolving hydrogen peroxide in sulfuric acid solution to obtain solution A, dissolving cyclohexanone in phthalic acid ester to obtain solution B, dropwise adding the solution B into the solution A, controlling the temperature, stirring and reacting to obtain cyclohexanone peroxide mixed solution, adding anhydrous sodium sulfate or anhydrous magnesium chloride, stirring and dissolving, standing, heating and preserving heat, removing lower-layer liquid to obtain cyclohexanone peroxide solution, adding stabilizing liquid, and obtaining the cyclohexanone peroxide transparent liquid with 50% content stability. According to the invention, the heating and salting-out dehydration steps are added in the preparation process of the cyclohexanone peroxide, and meanwhile, the stabilizing solution is added in the cyclohexanone peroxide solution, so that the solution is more transparent, has higher stability, is not crystallized at-24 ℃ for 90 days, is not crystallized at-15 ℃ for 120 days, is not crystallized at 0 ℃ for 180 days, and the stable transparent cyclohexanone peroxide liquid with 50% content is obtained.
Description
Technical Field
The invention belongs to the technical field of cyclohexanone peroxide production, and relates to a production process of a transparent liquid of cyclohexanone peroxide with stable 50% content.
Background
Putty, also called unsaturated polyester resin putty, is a filling material which has developed faster in the world for more than 20 years, and makes the automobile sheet metal repair industry which is behind once realize a leap of times. The putty for the automobile sheet metal generally comprises a component A and a component B, wherein the component A is colloid prepared by taking unsaturated polyester resin as main resin, the component B is curing agent for initiating the colloid of the component A to be cured, such as cyclohexanone peroxide, is a typical putty curing agent, most of putty at present depends on manual knife coating, has high requirements on construction techniques and experience of operators, has high labor intensity of workers, long construction period, greatly influences construction efficiency, damages the health of the workers and has high construction cost; the track traffic industry is gradually moving to intelligent manufacturing transformation and upgrading, and the development of the track traffic industry is limited by the traditional manual operation procedure.
Putty coating breaks through the limitation of conventional blade coating construction and realizes spraying operation, which is a good development direction of intelligent manufacturing. At present, on one hand, the realization of putty spraying needs to be improved and upgraded on the existing coating equipment, and further, the robot spraying can be realized. On the other hand, new putty products are needed to accommodate the requirements of the spray coating process. The existing putty cannot realize spraying atomization due to high resin viscosity and poor fluidity, and the system limitation of adopting a pasty curing agent is not suitable for spraying. Therefore, it is desirable to develop a curing agent in a liquid state to accommodate the spray atomization requirements.
The cyclohexanone peroxide is white or pale yellow needle-like crystalline powder in appearance, and is usually diluted into paste by phthalate due to unstable property, namely cyclohexanone peroxide paste. In the prior art, for the cyclohexanone peroxide curing agent, only a method for preparing cyclohexanone peroxide paste can be realized, and the transparent liquid curing agent for cyclohexanone peroxide is still freshly reported.
The cyclohexanone peroxide is 50% of the content of the current commercial cyclohexanone peroxide in China, most of the cyclohexanone peroxide is 20 kg per barrel, basically is crystal, is self-stirred before use (the cyclohexanone peroxide is easy to solidify), and is added into a system of unsaturated polyester resin for solidification after stirring, so that the operation is inconvenient, and the solidification is uneven and incomplete.
Patent application number CN201810114038 discloses a method for preparing cyclohexanone peroxide for putty, which comprises mixing cyclohexanone and phthalate to obtain solution a, and mixing hydrogen peroxide and inorganic acid to obtain solution B; dropwise adding the solution A into the solution B, stirring to react, and layering to obtain white floccules; and (3) taking the lower layer, washing with water to be neutral, then adding phthalate and a stabilizer, and uniformly mixing to obtain the cyclohexanone peroxide for the putty. However, the preparation method still only can obtain pasty cyclohexanone peroxide.
Disclosure of Invention
The invention aims to provide a production process of cyclohexanone peroxide transparent liquid with stable 50% content, and belongs to the technical field of cyclohexanone peroxide production. Dissolving hydrogen peroxide in sulfuric acid solution to obtain solution A, dissolving cyclohexanone in phthalic acid ester to obtain solution B, dropwise adding the solution B into the solution A, controlling the temperature, stirring and reacting to obtain cyclohexanone peroxide mixed solution, adding anhydrous sodium sulfate or anhydrous magnesium chloride, stirring and dissolving, standing, heating and preserving heat, removing lower-layer liquid to obtain cyclohexanone peroxide solution, adding stabilizing liquid, and obtaining the cyclohexanone peroxide transparent liquid with 50% content stability. According to the invention, the heating and salting-out dehydration steps are added in the preparation process of the cyclohexanone peroxide, and meanwhile, the stabilizing solution is added in the cyclohexanone peroxide solution, so that the solution is more transparent, has higher stability, is not crystallized at-24 ℃ for 90 days, is not crystallized at-15 ℃ for 120 days, is not crystallized at 0 ℃ for 180 days, and the stable transparent cyclohexanone peroxide liquid with 50% content is obtained.
The aim of the invention can be achieved by the following technical scheme:
a process for producing a cyclohexanone peroxide transparent liquid with a stable content of 50%, which comprises the following steps:
(1) Dissolving hydrogen peroxide in sulfuric acid solution to obtain solution A;
(2) Dissolving cyclohexanone in phthalate to obtain a solution B;
(3) Dropping the solution B into the solution A at a controlled speed, and stirring for reaction at a controlled temperature to obtain a mixed solution of cyclohexanone peroxide;
(4) Adding anhydrous sodium sulfate or anhydrous magnesium chloride into the mixed solution, stirring and dissolving, standing, heating to 50 ℃, preserving heat for 2 hours, and discharging lower-layer wastewater to obtain cyclohexanone peroxide solution;
(5) And adding a stabilizing solution when the temperature of the cyclohexanone peroxide solution is 50 ℃ to obtain a cyclohexanone peroxide transparent liquid with 50% stable content.
As a preferable technical scheme of the invention, the volume ratio of the hydrogen peroxide to the sulfuric acid solution in the step (1) is 3-5:1, the hydrogen peroxide is 25-30 wt% concentration hydrogen peroxide water solution, and the concentration of the sulfuric acid solution is 8-15mol/L.
As a preferable technical scheme of the invention, the phthalic acid ester in the step (2) is at least one of dioctyl phthalate, dimethyl phthalate and dibutyl phthalate.
As a preferable technical scheme of the invention, the volume ratio of the cyclohexanone to the phthalate in the step (2) is 1:2-4.
As a preferable technical scheme of the invention, in the step (3), the molar ratio of cyclohexanone in the solution B to hydrogen peroxide in the solution A is 1:1.1-1.3.
As a preferable technical scheme of the invention, the temperature control in the step (3) means that the temperature is controlled to be 25-38 ℃.
As a preferable technical scheme of the invention, the speed-control dropwise adding solution B in the step (3) is realized by the following method: and preparing an overtemperature explosion-proof PLC control system, monitoring the temperature of the reaction system, and when the temperature is higher than 38 ℃, regulating the temperature of the reaction system by the overtemperature explosion-proof PLC control system by reducing the dropping speed of the solution B, so that the reaction system is always kept between 25 and 38 ℃.
As a preferable technical scheme of the invention, the addition of the anhydrous sodium sulfate or the anhydrous magnesium chloride in the step (4) accounts for 8-20% of the mass of the mixed solution, and the standing time is 1-3h.
As a preferred embodiment of the present invention, the stabilizing solution in step (5) comprises ethylene glycol, diethylene glycol, cyclohexanediol, N-methylpyrrolidone and diacetone alcohol.
As a preferable technical scheme of the invention, the volume ratio of the cyclohexanone peroxide solution in the step (5) to the ethylene glycol, the diethylene glycol, the cyclohexanediol, the N-methylpyrrolidone and the diacetone alcohol is 100:15-25:8-15:10-15:12-18:9-16.
The invention has the beneficial effects that:
(1) According to the invention, a heating step and a salting-out dehydration step are added in the preparation process of cyclohexanone peroxide, the temperature is firstly increased to 50 ℃, anhydrous sodium sulfate or anhydrous magnesium chloride is added after the heat preservation is carried out for 2 hours, meanwhile, a stabilizing solution is added into the cyclohexanone peroxide solution, so that the solution is more transparent, the stability is higher, the cyclohexanone peroxide solution is not crystallized at-24 ℃ for 90 days, is not crystallized at-15 ℃ for 120 days, and is not crystallized at 0 ℃ for 180 days, and a stable transparent cyclohexanone peroxide liquid with 50% content is obtained;
(2) In the preparation process of cyclohexanone peroxide, an overtemperature explosion-proof PLC control system is adopted to adjust the dropping speed of cyclohexanone according to the temperature change of a reaction system, so that the temperature of the reaction system is maintained in a certain safety range, and the whole production process is safe and efficient.
Detailed Description
In order to further describe the technical means and effects adopted by the present invention for achieving the intended purpose, the following detailed description is given below with reference to the embodiments, structures, features and effects according to the present invention.
Example 1
A process for producing a cyclohexanone peroxide transparent liquid with a stable content of 50%, which comprises the following steps:
(1) Dissolving 25wt% of hydrogen peroxide water solution into 10mol/L sulfuric acid solution, and controlling the volume ratio of the hydrogen peroxide water solution to the sulfuric acid solution to be 3:1 to obtain solution A;
(2) Dissolving cyclohexanone in dioctyl phthalate, and controlling the volume ratio of the cyclohexanone to the dioctyl phthalate to be 1:3 to obtain a solution B;
(3) The method comprises the steps of (1) dropwise adding a solution B into a solution A at a controlled speed, controlling the molar ratio of cyclohexanone in the solution B to hydrogen peroxide in the solution A to be 1:1.1, stirring for reaction, monitoring the temperature of a reaction system by an overtemperature explosion-proof PLC control system, and when the temperature is higher than 38 ℃, regulating the temperature of the reaction system by the overtemperature explosion-proof PLC control system by reducing the dropping speed of the solution B, so that the reaction system is always kept between 25 ℃ and 38 ℃ to obtain a mixed solution of cyclohexanone peroxide;
(4) Adding anhydrous sodium sulfate accounting for 12% of the mass of the mixed solution into the mixed solution, stirring and dissolving, standing for 1.8h, heating to 50 ℃ and preserving heat for 2h, and discharging lower-layer wastewater to obtain cyclohexanone peroxide solution;
(5) And when the temperature of the cyclohexanone peroxide solution is 50 ℃, adding ethylene glycol, diethylene glycol, cyclohexanediol, N-methyl pyrrolidone and diacetone alcohol, and controlling the volume ratio of the cyclohexanone peroxide solution to the ethylene glycol, diethylene glycol, cyclohexanediol, N-methyl pyrrolidone and diacetone alcohol to be 100:19:11:13:13:15, so as to obtain the cyclohexanone peroxide transparent liquid with stable 50 percent content.
The yield of cyclohexanone peroxide in this example was 98.87%, and the 50% content of cyclohexanone peroxide transparent liquid was not crystallized at-24℃for 90 days, -15℃for 120 days, and at 0℃for 180 days.
Example 2
A process for producing a cyclohexanone peroxide transparent liquid with a stable content of 50%, which comprises the following steps:
(1) Dissolving 27wt% of hydrogen peroxide water solution in 8mol/L sulfuric acid solution, and controlling the volume ratio of the hydrogen peroxide water solution to the sulfuric acid solution to be 5:1 to obtain solution A;
(2) Dissolving cyclohexanone in dibutyl phthalate, and controlling the volume ratio of the cyclohexanone to the dibutyl phthalate to be 1:3 to obtain a solution B;
(3) The method comprises the steps of (1) dropwise adding a solution B into a solution A at a controlled speed, controlling the molar ratio of cyclohexanone in the solution B to hydrogen peroxide in the solution A to be 1:1.2, stirring for reaction, monitoring the temperature of a reaction system by an overtemperature explosion-proof PLC control system, and when the temperature is higher than 38 ℃, regulating the temperature of the reaction system by the overtemperature explosion-proof PLC control system by reducing the dropping speed of the solution B, so that the reaction system is always kept between 25 ℃ and 38 ℃ to obtain a mixed solution of cyclohexanone peroxide;
(4) Adding anhydrous magnesium chloride accounting for 15% of the mass of the mixed solution, stirring and dissolving, standing for 2 hours, heating to 50 ℃ and preserving heat for 2 hours, and discharging lower-layer wastewater to obtain cyclohexanone peroxide solution;
(5) And when the temperature of the cyclohexanone peroxide solution is 50 ℃, adding ethylene glycol, diethylene glycol, cyclohexanediol, N-methyl pyrrolidone and diacetone alcohol, and controlling the volume ratio of the cyclohexanone peroxide solution to the ethylene glycol, diethylene glycol, cyclohexanediol, N-methyl pyrrolidone and diacetone alcohol to be 100:21:9:13:17:10, so as to obtain the cyclohexanone peroxide transparent liquid with stable 50 percent content.
The yield of cyclohexanone peroxide in this example was 99.08%, and the 50% content of cyclohexanone peroxide transparent liquid was not crystallized at-24℃for 90 days, -15℃for 120 days, and at 0℃for 180 days.
Example 3
A process for producing a cyclohexanone peroxide transparent liquid with a stable content of 50%, which comprises the following steps:
(1) Dissolving 28wt% of hydrogen peroxide water solution in 12mol/L sulfuric acid solution, and controlling the volume ratio of the hydrogen peroxide water solution to the sulfuric acid solution to be 4:1 to obtain solution A;
(2) Dissolving cyclohexanone in dimethyl phthalate, and controlling the volume ratio of the cyclohexanone to the dimethyl phthalate to be 1:2 to obtain a solution B;
(3) The method comprises the steps of (1) dropwise adding a solution B into a solution A at a controlled speed, controlling the molar ratio of cyclohexanone in the solution B to hydrogen peroxide in the solution A to be 1:1.3, stirring for reaction, monitoring the temperature of a reaction system by an overtemperature explosion-proof PLC control system, and when the temperature is higher than 38 ℃, regulating the temperature of the reaction system by the overtemperature explosion-proof PLC control system by reducing the dropping speed of the solution B, so that the reaction system is always kept between 25 ℃ and 38 ℃ to obtain a mixed solution of cyclohexanone peroxide;
(4) Adding anhydrous magnesium chloride accounting for 17% of the mass of the mixed solution, stirring and dissolving, standing for 3h, heating to 50 ℃ and preserving heat for 2h, and discharging lower-layer wastewater to obtain cyclohexanone peroxide solution;
(5) And when the temperature of the cyclohexanone peroxide solution is 50 ℃, adding ethylene glycol, diethylene glycol, cyclohexanediol, N-methyl pyrrolidone and diacetone alcohol, and controlling the volume ratio of the cyclohexanone peroxide solution to the ethylene glycol, diethylene glycol, cyclohexanediol, N-methyl pyrrolidone and diacetone alcohol to be 100:19:9:14:15:13, so as to obtain the cyclohexanone peroxide transparent liquid with stable 50 percent content.
The yield of cyclohexanone peroxide in this example was 98.95%, and the 50% content of cyclohexanone peroxide transparent liquid was not crystallized at-24℃for 90 days, -15℃for 120 days, and at 0℃for 180 days.
Example 4
A process for producing a cyclohexanone peroxide transparent liquid with a stable content of 50%, which comprises the following steps:
(1) Dissolving 29wt% of hydrogen peroxide water solution in 14mol/L sulfuric acid solution, and controlling the volume ratio of the hydrogen peroxide water solution to the sulfuric acid solution to be 5:1 to obtain solution A;
(2) Dissolving cyclohexanone in dioctyl phthalate, and controlling the volume ratio of the cyclohexanone to the dioctyl phthalate to be 1:4 to obtain a solution B;
(3) The method comprises the steps of (1) dropwise adding a solution B into a solution A at a controlled speed, controlling the molar ratio of cyclohexanone in the solution B to hydrogen peroxide in the solution A to be 1:1.1, stirring for reaction, monitoring the temperature of a reaction system by an overtemperature explosion-proof PLC control system, and when the temperature is higher than 38 ℃, regulating the temperature of the reaction system by the overtemperature explosion-proof PLC control system by reducing the dropping speed of the solution B, so that the reaction system is always kept between 25 ℃ and 38 ℃ to obtain a mixed solution of cyclohexanone peroxide;
(4) Adding anhydrous sodium sulfate accounting for 18% of the mass of the mixed solution into the mixed solution, stirring and dissolving, standing for 2.2h, heating to 50 ℃ and preserving heat for 2h, and discharging lower-layer wastewater to obtain cyclohexanone peroxide solution;
(5) And when the temperature of the cyclohexanone peroxide solution is 50 ℃, adding ethylene glycol, diethylene glycol, cyclohexanediol, N-methyl pyrrolidone and diacetone alcohol, and controlling the volume ratio of the cyclohexanone peroxide solution to the ethylene glycol, diethylene glycol, cyclohexanediol, N-methyl pyrrolidone and diacetone alcohol to be 100:25:11:15:13:11, so as to obtain the cyclohexanone peroxide transparent liquid with stable 50 percent content.
The yield of cyclohexanone peroxide in this example was 99.12%, and the 50% content of cyclohexanone peroxide transparent liquid was not crystallized at-24℃for 90 days, -15℃for 120 days, and at 0℃for 180 days.
Example 5
A process for producing a cyclohexanone peroxide transparent liquid with a stable content of 50%, which comprises the following steps:
(1) Dissolving 30wt% of hydrogen peroxide water solution in 12mol/L sulfuric acid solution, and controlling the volume ratio of the hydrogen peroxide water solution to the sulfuric acid solution to be 3:1 to obtain solution A;
(2) Dissolving cyclohexanone in dimethyl phthalate, and controlling the volume ratio of the cyclohexanone to the dimethyl phthalate to be 1:4 to obtain a solution B;
(3) The method comprises the steps of (1) dropwise adding a solution B into a solution A at a controlled speed, controlling the molar ratio of cyclohexanone in the solution B to hydrogen peroxide in the solution A to be 1:1.2, stirring for reaction, monitoring the temperature of a reaction system by an overtemperature explosion-proof PLC control system, and when the temperature is higher than 38 ℃, regulating the temperature of the reaction system by the overtemperature explosion-proof PLC control system by reducing the dropping speed of the solution B, so that the reaction system is always kept between 25 ℃ and 38 ℃ to obtain a mixed solution of cyclohexanone peroxide;
(4) Adding anhydrous magnesium chloride accounting for 20% of the mass of the mixed solution, stirring and dissolving, standing for 1h, heating to 50 ℃ and preserving heat for 2h, and discharging lower-layer wastewater to obtain cyclohexanone peroxide solution;
(5) And when the temperature of the cyclohexanone peroxide solution is 50 ℃, adding ethylene glycol, diethylene glycol, cyclohexanediol, N-methyl pyrrolidone and diacetone alcohol, and controlling the volume ratio of the cyclohexanone peroxide solution to the ethylene glycol, diethylene glycol, cyclohexanediol, N-methyl pyrrolidone and diacetone alcohol to be 100:16:8:15:17:15, so as to obtain the cyclohexanone peroxide transparent liquid with stable 50 percent content.
The yield of cyclohexanone peroxide in this example was 99.15%, and the 50% content of cyclohexanone peroxide transparent liquid was not crystallized at-24℃for 90 days, -15℃for 120 days, and at 0℃for 180 days.
Example 6
A process for producing a cyclohexanone peroxide transparent liquid with a stable content of 50%, which comprises the following steps:
(1) Dissolving 26wt% of hydrogen peroxide water solution in 15mol/L sulfuric acid solution, and controlling the volume ratio of the hydrogen peroxide water solution to the sulfuric acid solution to be 5:1 to obtain solution A;
(2) Dissolving cyclohexanone in dioctyl phthalate, and controlling the volume ratio of the cyclohexanone to the dioctyl phthalate to be 1:3 to obtain a solution B;
(3) The method comprises the steps of (1) dropwise adding a solution B into a solution A at a controlled speed, controlling the molar ratio of cyclohexanone in the solution B to hydrogen peroxide in the solution A to be 1:1.3, stirring for reaction, monitoring the temperature of a reaction system by an overtemperature explosion-proof PLC control system, and when the temperature is higher than 38 ℃, regulating the temperature of the reaction system by the overtemperature explosion-proof PLC control system by reducing the dropping speed of the solution B, so that the reaction system is always kept between 25 ℃ and 38 ℃ to obtain a mixed solution of cyclohexanone peroxide;
(4) Adding anhydrous magnesium chloride accounting for 15% of the mass of the mixed solution, stirring and dissolving, standing for 2 hours, heating to 50 ℃ and preserving heat for 2 hours, and discharging lower-layer wastewater to obtain cyclohexanone peroxide solution;
(5) And when the temperature of the cyclohexanone peroxide solution is 50 ℃, adding ethylene glycol, diethylene glycol, cyclohexanediol, N-methyl pyrrolidone and diacetone alcohol, and controlling the volume ratio of the cyclohexanone peroxide solution to the ethylene glycol, diethylene glycol, cyclohexanediol, N-methyl pyrrolidone and diacetone alcohol to be 100:21:9:13:17:10, so as to obtain the cyclohexanone peroxide transparent liquid with stable 50 percent content.
The yield of cyclohexanone peroxide in this example was 98.99%, and the 50% content of cyclohexanone peroxide transparent liquid was not crystallized at-24℃for 90 days, -15℃for 120 days, and at 0℃for 180 days.
The present invention is not limited to the above embodiments, but is capable of modification and variation in detail, and other modifications and variations can be made by those skilled in the art without departing from the scope of the present invention.
Claims (10)
1. A process for producing a cyclohexanone peroxide transparent liquid with a stable content of 50%, which is characterized by comprising the following steps:
(1) Dissolving hydrogen peroxide in sulfuric acid solution to obtain solution A;
(2) Dissolving cyclohexanone in phthalate to obtain a solution B;
(3) Dropping the solution B into the solution A at a controlled speed, and stirring for reaction at a controlled temperature to obtain a mixed solution of cyclohexanone peroxide;
(4) Adding anhydrous sodium sulfate or anhydrous magnesium chloride into the mixed solution, stirring and dissolving, standing, heating to 50 ℃, preserving heat for 2 hours, and discharging lower-layer wastewater to obtain cyclohexanone peroxide solution;
(5) And adding a stabilizing solution when the temperature of the cyclohexanone peroxide solution is 50 ℃ to obtain a cyclohexanone peroxide transparent liquid with 50% stable content.
2. The process for producing the cyclohexanone peroxide transparent liquid with the stable 50% content, according to claim 1, is characterized in that the volume ratio of the hydrogen peroxide solution to the sulfuric acid solution in the step (1) is 3-5:1, the hydrogen peroxide is 25-30 wt% concentration hydrogen peroxide aqueous solution, and the concentration of the sulfuric acid solution is 8-15mol/L.
3. The process for producing a cyclohexanone peroxide transparent liquid with a stable content of 50% according to claim 1, wherein the phthalate ester in step (2) is at least one of dioctyl phthalate, dimethyl phthalate and dibutyl phthalate.
4. The process for producing a transparent liquid of cyclohexanone peroxide with a stable content of 50% according to claim 1, wherein the volume ratio of cyclohexanone to phthalate in step (2) is 1:2-4.
5. The process for producing a transparent liquid of cyclohexanone peroxide with a stable content of 50% according to claim 1, wherein the molar ratio of cyclohexanone in the solution B to hydrogen peroxide in the solution a in the step (3) is 1:1.1-1.3.
6. The process for producing a cyclohexanone peroxide transparent liquid with a stable content of 50% according to claim 1, wherein the temperature control in the step (3) is 25-38 ℃.
7. The process for producing the cyclohexanone peroxide transparent liquid with the stable content of 50 percent according to claim 5, wherein the speed-control dropwise adding of the solution B in the step (3) is realized by the following method: and preparing an overtemperature explosion-proof PLC control system, monitoring the temperature of the reaction system, and when the temperature is higher than 38 ℃, regulating the temperature of the reaction system by the overtemperature explosion-proof PLC control system by reducing the dropping speed of the solution B, so that the reaction system is always kept between 25 and 38 ℃.
8. The process for producing the cyclohexanone peroxide transparent liquid with the stable content of 50 percent according to claim 1, wherein the addition amount of the anhydrous sodium sulfate or the anhydrous magnesium chloride in the step (4) accounts for 8-20 percent of the mass of the mixed liquid, and the standing time is 1-3 hours.
9. A process for the production of a 50% stable cyclohexanone peroxide transparent liquid according to claim 1, wherein the stabilizing liquid in step (5) comprises ethylene glycol, diethylene glycol, cyclohexanediol, N-methylpyrrolidone and diacetone alcohol.
10. The process for producing a transparent liquid of cyclohexanone peroxide with a stable content of 50% according to claim 9, wherein the volume ratio of the cyclohexanone peroxide solution to ethylene glycol, diethylene glycol, cyclohexanediol, N-methylpyrrolidone and diacetone alcohol in step (5) is 100:15-25:8-15:10-15:12-18:9-16.
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