CN117776985A - Preparation method of 4-hydroxy-4' -isopropoxy diphenyl sulfone - Google Patents
Preparation method of 4-hydroxy-4' -isopropoxy diphenyl sulfone Download PDFInfo
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- CN117776985A CN117776985A CN202311797217.5A CN202311797217A CN117776985A CN 117776985 A CN117776985 A CN 117776985A CN 202311797217 A CN202311797217 A CN 202311797217A CN 117776985 A CN117776985 A CN 117776985A
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- Prior art keywords
- hydroxy
- diphenyl sulfone
- toluene
- isopropoxy diphenyl
- added
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- ZTILAOCGFRDHBH-UHFFFAOYSA-N 4-(4-propan-2-yloxyphenyl)sulfonylphenol Chemical compound C1=CC(OC(C)C)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 ZTILAOCGFRDHBH-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 165
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000001914 filtration Methods 0.000 claims abstract description 23
- 239000011343 solid material Substances 0.000 claims abstract description 21
- 238000004321 preservation Methods 0.000 claims abstract description 15
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 claims abstract description 13
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims abstract description 13
- 239000001110 calcium chloride Substances 0.000 claims abstract description 13
- 229910001628 calcium chloride Inorganic materials 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 12
- 238000001035 drying Methods 0.000 claims abstract description 12
- 238000001256 steam distillation Methods 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 239000007864 aqueous solution Substances 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 11
- 238000004090 dissolution Methods 0.000 claims description 9
- 230000001105 regulatory effect Effects 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000005086 pumping Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000036571 hydration Effects 0.000 abstract description 7
- 238000006703 hydration reaction Methods 0.000 abstract description 7
- 238000000967 suction filtration Methods 0.000 abstract 1
- 239000002245 particle Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 239000013078 crystal Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- 238000003801 milling Methods 0.000 description 3
- 238000001238 wet grinding Methods 0.000 description 3
- -1 adopts 4 Chemical compound 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002591 computed tomography Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229950000188 halopropane Drugs 0.000 description 1
- 238000002595 magnetic resonance imaging Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of 4-hydroxy-4 '-isopropoxy diphenyl sulfone, bisphenol S is added into liquid alkali, calcium chloride accounting for 0.1-0.5% of the weight of the liquid alkali is added, the temperature is raised, 2-bromopropane is dropwise added for 2 hours, the heat preservation reaction is continued for 8-20 hours, toluene is added, the temperature is raised to 70-80 ℃, the pH value of the system is adjusted to 8-9 by acid, stirring is carried out for 1 hour, standing and layering are carried out, 4-hydroxy-4' -isopropoxy diphenyl sulfone is added into a toluene layer, unreacted bisphenol S is remained in water, water is added into the toluene layer, the pH value of the system is adjusted to 5-7, a water layer is removed, the toluene layer is cooled, the temperature is kept for 1 hour at 20 ℃, the solid material is obtained through suction filtration, and the toluene remained in the solid material is distilled out by a steam distillation method; filtering and drying to obtain the finished product 4-hydroxy-4 ' -isopropoxy diphenyl sulfone, wherein the content of the 4-hydroxy-3-isopropyl-4 ' -isopropoxy diphenyl sulfone is more than or equal to 99 percent, the content of the 4-hydroxy-3-isopropyl-4 ' -isopropoxy diphenyl sulfone is between 0.1 and 0.6 percent, and the yield is more than 90 percent. The invention can prevent hydration.
Description
Technical Field
The invention belongs to the technical field of chemical industry, and particularly relates to a preparation method of 4-hydroxy-4' -isopropoxy diphenyl sulfone.
Background
The thermosensitive recording material has the advantages of flexible printing format, high image quality, high speed, low price, simple recording equipment, more maintenance, no noise in the recording process and the like, and can be used as the output recording material of fax machines, POS machines, label printers, CR, DR and other X-ray image diagnosis, magnetic Resonance Imaging (MRI), X-ray Computed Tomography (CT) and other medical equipment, and simultaneously, the defects that noble metal silver is necessary to be used as a raw material and the preparation and use processes are complex in the traditional silver salt film technology are avoided.
The 4-hydroxy-4' -isopropoxy diphenyl sulfone is a widely applied thermo-sensitive color developing agent, and has the advantages that the prepared thermo-sensitive material has high sensitivity and good image preservation performance, and is particularly suitable for being used as the thermo-sensitive color developing agent of high-grade thermo-sensitive paper and medical films.
In general, components of thermosensitive recording materials, such as leuco dyes, color developers and sensitizers (sensitizers), must be granulated by wet milling before use.
In recent years, as demand for higher sensitivity of thermosensitive recording materials has increased, micronization of these particles has been pursued. However, micronization of 4-hydroxy-4' -isopropoxy diphenyl sulfone sometimes causes crystal growth during wet milling of the micronization or during storage of the prepared dispersion. In particular, when 4-hydroxy-4' -isopropoxydiphenyl sulfone is pulverized into fine particles of 1 μm or less, crystal growth is liable to occur. This crystal growth is attributed to the hydration of 4-hydroxy-4' -isopropoxy diphenyl sulfone, and the grown crystals are hydrates, and thermosensitive recording materials produced using a dispersion containing such hydrates often suffer from fogging, causing the surface of the paper sheet of the recording paper to be not clean, and also causing the skin to be severely contaminated.
In order to prevent 4-hydroxy-4' -isopropoxy diphenyl sulfone from generating hydrate during the micronization, many approaches have been taken.
In chinese patent CN1052194, a derivative of diphenyl sulfone is used as a means to prevent hydration of 4-hydroxy-4 '-isopropoxy diphenyl sulfone, the addition amount is 0.05-5% (calculated as 4-hydroxy-4' -isopropoxy diphenyl sulfone).
The existing synthesis process of 4-hydroxy-4 '-isopropoxy diphenyl sulfone mainly adopts 4,4' -dihydroxyl diphenyl sulfone (bisphenol S) and 2-halopropane to prepare 4-hydroxy-4 '-isopropoxy diphenyl sulfone through nucleophilic substitution reaction, by-products such as 4,4' -diisopropyloxy diphenyl sulfone are generated in the synthesis process, and unreacted raw material bisphenol S is also present in the system.
In the method for preparing diphenyl sulfone compound by Chinese patent CN1273447, bisphenol S and 2-bromopropane are subjected to nucleophilic substitution reaction to obtain 4-hydroxy-4 ' -isopropoxy diphenyl sulfone, and the pH value of the system is adjusted for 2 times to separate 4-hydroxy-4 ' -isopropoxy diphenyl sulfone and bisphenol S, so that 4-hydroxy-4 ' -isopropoxy diphenyl sulfone with the content of more than 99 percent is obtained.
At present, the method has a plurality of problems, and the 4-hydroxy-3-isopropyl-4 '-isopropoxy diphenyl sulfone disclosed in Chinese patent CN1052194 can be used as a good hydration inhibitor, but enough 4-hydroxy-3-isopropyl-4' -isopropoxy diphenyl sulfone cannot be synthesized in the existing synthesis method of the 4-hydroxy-4 '-isopropoxy diphenyl sulfone, and the 4-hydroxy-3-isopropyl-4' -isopropoxy diphenyl sulfone needs to be additionally added in preparing a thermosensitive color development system dispersion liquid, so that the use difficulty of a downstream user is increased.
Disclosure of Invention
The invention aims to: the invention aims to overcome the defects in the prior art and provide a preparation method of 4-hydroxy-4' -isopropoxy diphenyl sulfone capable of preventing hydration.
The technical scheme is as follows: in order to solve the technical problems, the invention relates to a preparation method of 4-hydroxy-4' -isopropoxy diphenyl sulfone,
adding 1 mol of bisphenol S into 2-3 mol of 30% liquid alkali, adding calcium chloride accounting for 0.1-0.5% of the weight of the liquid alkali, heating to 50-56 ℃, dropwise adding 1 mol of 2-bromopropane for 2 hours, continuing to perform heat preservation reaction for 8-20 hours, adding 1400 g of toluene, heating to 70-80 ℃, adjusting the pH value of the system to 8-9 by acid, stirring for 1 hour, standing for layering, adding 300 g of water into the toluene layer, adjusting the pH value of the system to 5-7, removing the water layer, cooling the toluene layer, performing heat preservation for 1 hour at 20 ℃, pumping filtration, and distilling off the toluene remained in the solid material by a steam distillation method; filtering and drying to obtain the finished product 4-hydroxy-4 ' -isopropoxy diphenyl sulfone, wherein the content of the 4-hydroxy-3-isopropyl-4 ' -isopropoxy diphenyl sulfone is more than or equal to 99 percent, the content of the 4-hydroxy-3-isopropyl-4 ' -isopropoxy diphenyl sulfone is between 0.1 and 0.6 percent, and the yield is more than 90 percent.
Preferably, 200 g of 30% sodium hydroxide aqueous solution and 250 g of bisphenol S are added into a flask, 0.2 g of calcium chloride is added, the temperature is raised to 56 ℃ for dissolution, 123 g of 2-bromopropane is dropwise added at 50-56 ℃ for 2 hours, and the heat preservation reaction is continued for 8 hours; adding 1400 g of toluene, raising the temperature to 70-80, regulating the pH value of the system to 8-9 by using acid, stirring for 1 hour, standing for layering, adding 300 g of water into the toluene layer, regulating the pH value of the system to 5-7, removing the water layer, cooling the toluene layer, preserving the temperature for 1 hour at 20 ℃, filtering to obtain a solid material, and distilling off the residual toluene of the solid material by using steam distillation; filtration and drying to obtain 267.5 g of 4-hydroxy-4 '-isopropoxy diphenyl sulfone with the content of 99.85 percent, wherein the content of 4-hydroxy-3-isopropyl-4' -isopropoxy diphenyl sulfone is 0.10 percent and the content of bisphenol S is 0.01 percent.
Preferably, 400 g of 30% sodium hydroxide aqueous solution and 250 g of bisphenol S are added into a flask, 2 g of calcium chloride is added, the temperature is raised to 56 ℃ for dissolution, 123 g of 2-bromopropane is dropwise added at 50-56 ℃ for 1 hour, and the heat preservation reaction is continued for 8 hours; adding 1400 g of toluene, raising the temperature to 70-80, adjusting the pH value to 8-9 by using acid, stirring for 1 hour, standing for layering, adding a small amount of unreacted bisphenol S into the toluene layer, adding 300 g of water into the toluene layer, adjusting the pH value of the system to 5-7, separating a water layer, cooling the toluene layer, keeping the temperature at 20 ℃ for 1 hour, filtering to obtain a solid material, and distilling off the toluene remained in the solid material by using steam distillation; filtering and drying to obtain 269 g of 4-hydroxy-4 '-isopropoxy diphenyl sulfone with the content of 99.36%, the content of 4-hydroxy-3-isopropyl-4' -isopropoxy diphenyl sulfone is 0.60% and the content of bisphenol S is 0.01%.
The beneficial effects are that: compared with the prior art, the invention has the remarkable advantages that:
(1) If the product of the invention is used as a thermosensitive color developer, a hydration inhibitor is not needed to be added, so that the cost of a downstream user is saved.
(2) Calcium chloride is added into the reaction system to promote the generation of 4-hydroxy-3-isopropyl-4 ' -isopropoxy diphenyl sulfone, and 4-hydroxy-3-isopropyl-4 ' -isopropoxy is not needed to be additionally added into the dispersion system to inhibit the hydration of 4-hydroxy-4 ' -isopropoxy diphenyl sulfone when the dispersion system is used.
Detailed Description
The present invention will be further described with reference to examples and comparative examples.
Example 1
200 g of 30% sodium hydroxide aqueous solution and 250 g of bisphenol S are added into a flask, 0.2 g of calcium chloride is added, the temperature is raised to 56 ℃ for dissolution, 123 g of 2-bromopropane is dropwise added at 50-56 ℃ for 2 hours, and the heat preservation reaction is continued for 8 hours; adding 1400 g of toluene, raising the temperature to 70-80, regulating the pH value of the system to 8-9 by using acid, stirring for 1 hour, standing for layering, adding 300 g of water into the toluene layer, regulating the pH value of the system to 5-7, removing the water layer, cooling the toluene layer, preserving the temperature for 1 hour at 20 ℃, filtering to obtain a solid material, and distilling off the residual toluene of the solid material by using steam distillation; filtration and drying to obtain 267.5 g of 4-hydroxy-4 '-isopropoxy diphenyl sulfone with the content of 99.85 percent, wherein the content of 4-hydroxy-3-isopropyl-4' -isopropoxy diphenyl sulfone is 0.10 percent and the content of bisphenol S is 0.01 percent.
31.1 g of a 15% aqueous solution of polyvinyl alcohol, 30 g of pure water, 195 g of glass spheres (1.0-1.5 mm. Phi.) and 14 g of 4-hydroxy-4' -isopropoxy-diphenyl-sulfone prepared as described above were weighed and mixed, and then the mixture was wet-ground with a wet grinder at 25℃and, according to the observation by a microscope, no crystal formation was seen in the mixture after grinding for 10 hours, and the particle size in the ground mixture was 0.3. Mu.m, as measured by a laser diffraction particle size distribution analyzer (50% average particle size).
Example 2
400 g of 30% sodium hydroxide aqueous solution and 250 g of bisphenol S are added into a flask, 2 g of calcium chloride is added, the temperature is raised to 56 ℃ for dissolution, 123 g of 2-bromopropane is dropwise added at 50-56 ℃ for 1 hour, and the heat preservation reaction is continued for 14 hours; adding 1400 g of toluene, raising the temperature to 70-80, adjusting the pH value to 8-9 by using acid, stirring for 1 hour, standing for layering, adding a small amount of unreacted bisphenol S into the toluene layer, adding 300 g of water into the toluene layer, adjusting the pH value of the system to 5-7, separating a water layer, cooling the toluene layer, keeping the temperature at 20 ℃ for 1 hour, filtering to obtain a solid material, and distilling off the toluene remained in the solid material by using steam distillation; filtering and drying to obtain 269 g of 4-hydroxy-4 '-isopropoxy diphenyl sulfone with the content of 99.36%, the content of 4-hydroxy-3-isopropyl-4' -isopropoxy diphenyl sulfone is 0.60% and the content of bisphenol S is 0.01%.
31.1 g of a 15% aqueous solution of polyvinyl alcohol, 30 g of pure water, 195 g of glass spheres (1.0-1.5 mm. Phi.) and 14 g of 4-hydroxy-4' -isopropoxy-diphenyl sulfone prepared as described above were weighed and mixed. Then, the mixture was wet-milled with a wet mill at 25℃and, according to the observation by a microscope, the particle size in the milled mixture was 0.3. Mu.m, as measured by a laser diffraction particle size distribution analyzer (50% average particle size) for crystal formation was not seen in the mixture after milling for 10 hours.
Example 3
267 g of 30% sodium hydroxide aqueous solution and 250 g of bisphenol S are added into a flask, 0.8 g of calcium chloride is added, the temperature is raised to 56 ℃ for dissolution, 123 g of 2-bromopropane is dropwise added at 50-56 ℃ for 1 hour, and the heat preservation reaction is continued for 16 hours; adding 1400 g of toluene, raising the temperature to 70-80, adjusting the pH value to 8-9 by using acid, stirring for 1 hour, standing for layering, adding a small amount of unreacted bisphenol S into the toluene layer, adding 300 g of water into the toluene layer, adjusting the pH value of the system to 5-7, separating a water layer, cooling the toluene layer, keeping the temperature at 20 ℃ for 1 hour, filtering to obtain a solid material, and distilling off the toluene remained in the solid material by using steam distillation; filtering and drying to obtain 263.2 g of 4-hydroxy-4 '-isopropoxy diphenyl sulfone with the content of 99.60%, the content of 4-hydroxy-3-isopropyl-4' -isopropoxy diphenyl sulfone is 0.35%, and the content of bisphenol S is 0.01%.
31.1 g of a 15% aqueous solution of polyvinyl alcohol, 30 g of pure water, 195 g of glass spheres (1.0-1.5 mm. Phi.) and 13.9 g of 4-hydroxy-4' -isopropoxy diphenylsulfone prepared on were weighed and mixed. Then, the mixture was wet-milled with a wet mill at 25℃and, according to the observation by a microscope, no crystal formation was observed in the mixture after milling for 10 hours, and the particle size in the milled mixture was 0.3. Mu.m, as measured by a laser diffraction particle size distribution analyzer (50% average particle size).
Example 4
Adding 300 g of 30% sodium hydroxide aqueous solution and 250 g of bisphenol S into a flask, adding 0.6 g of calcium chloride, heating to 56 ℃ for dissolution, dropwise adding 123 g of 2-bromopropane at 50-56 ℃ for 2 hours, and continuing to perform heat preservation reaction for 20 hours; adding 1400 g of toluene, raising the temperature to 70-80, adjusting the pH value to 8-9 by using acid, stirring for 1 hour, standing for layering, adding a small amount of unreacted bisphenol S into the toluene layer, adding 300 g of water into the toluene layer, adjusting the pH value of the system to 5-7, separating a water layer, cooling the toluene layer, keeping the temperature at 20 ℃ for 1 hour, filtering to obtain a solid material, and distilling off the residual toluene of the material by using steam distillation; filtering and drying to obtain 270 g of 4-hydroxy-4 '-isopropoxy diphenyl sulfone with the content of 99.70 percent, wherein the content of 4-hydroxy-3-isopropyl-4' -isopropoxy diphenyl sulfone is 0.26 percent and the content of bisphenol S is 0.01 percent.
31.1 g of a 15% aqueous solution of polyvinyl alcohol, 30 g of pure water, 195 g of glass spheres (1.0-1.5 mm. Phi.) and 14 g of 4-hydroxy-4' -isopropoxy-diphenyl-sulfone prepared as described above were weighed and mixed. Then, the mixture was wet-milled with a wet mill at 25℃and, according to the observation by a microscope, no crystal formation was observed in the mixture after milling for 10 hours, and the particle size in the milled mixture was 0.3. Mu.m, as measured with a laser diffraction particle size distribution analyzer (50% average particle size).
Comparative example (same as example 1 except that calcium chloride was not added)
200 g of 30% sodium hydroxide aqueous solution and 250 g of bisphenol S are added into a flask, the temperature is raised to 56 ℃ for dissolution, 123 g of 2-bromopropane is dropwise added at the temperature of 50-56 ℃ for 2 hours, and the reaction is continued for 8 hours under heat preservation; adding 1400 g of toluene, raising the temperature to 70-80, adjusting the pH value to 8-9 by using acid, stirring for 1 hour, standing for layering, adding a small amount of unreacted bisphenol S into the toluene layer, adding 300 g of water into the toluene layer, adjusting the pH value of the system to 5-7, separating a water layer, cooling the toluene layer, keeping the temperature at 20 ℃ for 1 hour, filtering to obtain a solid material, and distilling off the toluene remained in the solid material by using steam distillation; filtration and drying give 267 g of 4-hydroxy-4 '-isopropoxy diphenyl sulfone with a content of 99.9%, the content of 4-hydroxy-3-isopropyl-4' -isopropoxy diphenyl sulfone was not detected, and the content of bisphenol S was 0.01%.
31.1 g of a 15% aqueous solution of polyvinyl alcohol, 30 g of pure water, 195 g of glass spheres (1.0-1.5 mm. Phi.) and 14 g of 4-hydroxy-4' -isopropoxy-diphenyl-sulfone prepared as described above were weighed and mixed, and then the mixture was wet-ground with a wet grinder at 25℃to make crystal formation clearly visible in the mixture after wet-grinding for 1 hour according to observation under a microscope, and the particle size in the mixture after grinding was 0.8. Mu.m, using a laser diffraction particle size distribution analyzer (50% average particle size).
The present invention provides a method and a thought, and a method for implementing the technical scheme are numerous, the above description is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, several improvements and modifications can be made, and these improvements and modifications should also be regarded as protection scope of the present invention, and each component that is not explicitly described in the present embodiment can be implemented by the prior art.
Claims (3)
1. A preparation method of 4-hydroxy-4' -isopropoxy diphenyl sulfone is characterized in that:
adding 1 mol of bisphenol S into 2-3 mol of 30% liquid alkali, adding calcium chloride accounting for 0.1-0.5% of the weight of the liquid alkali, heating to 50-56 ℃, dropwise adding 1 mol of 2-bromopropane for 2 hours, continuing to perform heat preservation reaction for 8-20 hours, adding 1400 g of toluene, heating to 70-80 ℃, adjusting the pH value of the system to 8-9 by acid, stirring for 1 hour, standing for layering, adding 300 g of water into the toluene layer, adjusting the pH value of the system to 5-7, removing the water layer, cooling the toluene layer, performing heat preservation for 1 hour at 20 ℃, pumping filtration, and distilling off the toluene remained in the solid material by a steam distillation method; filtering and drying to obtain the finished product 4-hydroxy-4 ' -isopropoxy diphenyl sulfone, wherein the content of the 4-hydroxy-3-isopropyl-4 ' -isopropoxy diphenyl sulfone is more than or equal to 99 percent, the content of the 4-hydroxy-3-isopropyl-4 ' -isopropoxy diphenyl sulfone is between 0.1 and 0.6 percent, and the yield is more than 90 percent.
2. The method for producing 4-hydroxy-4' -isopropoxy diphenyl sulfone according to claim 1, characterized in that:
200 g of 30% sodium hydroxide aqueous solution and 250 g of bisphenol S are added into a flask, 0.2 g of calcium chloride is added, the temperature is raised to 56 ℃ for dissolution, 123 g of 2-bromopropane is dropwise added at 50-56 ℃ for 2 hours, and the heat preservation reaction is continued for 8 hours; adding 1400 g of toluene, raising the temperature to 70-80, regulating the pH value of the system to 8-9 by using acid, stirring for 1 hour, standing for layering, adding 300 g of water into the toluene layer, regulating the pH value of the system to 5-7, removing the water layer, cooling the toluene layer, preserving the temperature for 1 hour at 20 ℃, filtering to obtain a solid material, and distilling off the residual toluene of the solid material by using steam distillation; filtration and drying to obtain 267.5 g of 4-hydroxy-4 '-isopropoxy diphenyl sulfone with the content of 99.85 percent, wherein the content of 4-hydroxy-3-isopropyl-4' -isopropoxy diphenyl sulfone is 0.10 percent and the content of bisphenol S is 0.01 percent.
3. The method for producing 4-hydroxy-4' -isopropoxy diphenyl sulfone according to claim 1, characterized in that:
400 g of 30% sodium hydroxide aqueous solution and 250 g of bisphenol S are added into a flask, 2 g of calcium chloride is added, the temperature is raised to 56 ℃ for dissolution, 123 g of 2-bromopropane is dropwise added at 50-56 ℃ for 1 hour, and the heat preservation reaction is continued for 8 hours; adding 1400 g of toluene, raising the temperature to 70-80, adjusting the pH value to 8-9 by using acid, stirring for 1 hour, standing for layering, adding a small amount of unreacted bisphenol S into the toluene layer, adding 300 g of water into the toluene layer, adjusting the pH value of the system to 5-7, separating a water layer, cooling the toluene layer, keeping the temperature at 20 ℃ for 1 hour, filtering to obtain a solid material, and distilling off the toluene remained in the solid material by using steam distillation; filtering and drying to obtain 269 g of 4-hydroxy-4 '-isopropoxy diphenyl sulfone with the content of 99.36%, the content of 4-hydroxy-3-isopropyl-4' -isopropoxy diphenyl sulfone is 0.60% and the content of bisphenol S is 0.01%.
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| CN202311797217.5A CN117776985A (en) | 2023-12-26 | 2023-12-26 | Preparation method of 4-hydroxy-4' -isopropoxy diphenyl sulfone |
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| CN202311797217.5A CN117776985A (en) | 2023-12-26 | 2023-12-26 | Preparation method of 4-hydroxy-4' -isopropoxy diphenyl sulfone |
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