CN102351653A - Method for purifying 2, 4-di-(1-phenylisopropyl) phenol with secondary recrystallization - Google Patents
Method for purifying 2, 4-di-(1-phenylisopropyl) phenol with secondary recrystallization Download PDFInfo
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- CN102351653A CN102351653A CN201110211905XA CN201110211905A CN102351653A CN 102351653 A CN102351653 A CN 102351653A CN 201110211905X A CN201110211905X A CN 201110211905XA CN 201110211905 A CN201110211905 A CN 201110211905A CN 102351653 A CN102351653 A CN 102351653A
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Abstract
The invention relates a method for purifying 2, 4-di-(1-phenylisopropyl) phenol, solving the problems of complicate process, low yield, and bad purity of purification method of 2, 4-di-(1-phenylisopropyl) phenol existing in the prior art. The method comprises the following steps: dissolving a crude product of 2, 4-di-(1-phenylisopropyl) phenol to be purified in petroleum ether, cooling and then dissolving crystals out, drying the crystals to obtain first crystallized crystals; dissolving the first crystallized crystals in a mixed solvent of methanol and water, cooling and then dissolving crystals out, drying the crystals to obtain the pure 2, 4-di-(1-phenylisopropyl) phenol, wherein, the purity of the pure 2, 4-di-(1-phenylisopropyl) phenol is larger than 99 %, and the extraction rate of the product is 70-85 %. The purification method is simple and is suitable for industrial production.
Description
Technical field
The present invention relates to 2, the method for purification of 4-di-(1-phenylisopropyl) phenol.
Background technology
2, the 4-di-(1-phenylisopropyl) phenol is a kind of important fine chemical material, and the UV light absorber, tensio-active agent, agricultural emulsifier, the sterilant that can be used as polycarbonate article are used for the production of fine chemicals.But because 2, the 4-di-(1-phenylisopropyl) phenol all contains 2-cumylphenol, 4-cumylphenol, 2,4 inevitably in the reaction system in building-up process, and the oligomer of 6-three cumylphenols and alpha-methyl styrene makes 2, and the purity of 4-di-(1-phenylisopropyl) phenol only is 60%～80%.Existing 2, the method for purification of 4-di-(1-phenylisopropyl) phenol be after the underpressure distillation with a kind of solvent recrystallization repeatedly, promptly through underpressure distillation collection main distillate fraction, the purity that obtains crude product is 85%～90%, adopt then a kind of solvent warp repeatedly the method for recrystallization come refined product.This method of purification complex process and be difficult to remove complicated and diversified by product in the product, yield only are 30%～60%, product purity is lower than 97%.
Summary of the invention
The objective of the invention is in order to solve existingly 2,4-di-(1-phenylisopropyl) phenol method of purification complex process, yield are low, the problem of purity difference, provide and utilize secondary recrystallization to purify 2, the method for 4-di-(1-phenylisopropyl) phenol.
The present invention utilizes secondary recrystallization to purify 2; The method of 4-di-(1-phenylisopropyl) phenol is carried out according to the following steps: one; Sherwood oil recrystallization: by to be purified 2; The ratio of 4-di-(1-phenylisopropyl) phenol crude product and sherwood oil is that 1g: 1.2mL～3mL takes by weighing to be purified 2; 4-di-(1-phenylisopropyl) phenol crude product and sherwood oil; With to be purified 2; 4-di-(1-phenylisopropyl) phenol crude product joins in the sherwood oil; After the stirring and dissolving; To be cooled to temperature be 0 ℃～10 ℃ and keep 8h～12h; Filter, obtain sherwood oil mother liquor and solid formation, solid formation sherwood oil drip washing; Being placed on vacuum tightness then is 0.085MPa～0.095MPa; Temperature is vacuum-drying 4h～6h under 40 ℃～60 ℃ the condition, obtains the primary crystallization crystal; Two; The methanol-water recrystallization: by the volume ratio of methyl alcohol and water is to measure first alcohol and water and mix at 6～9: 1; Obtain the methanol-water mixed solvent; Ratio by primary crystallization crystal and methanol-water mixed solvent is that 1g: 1mL～3mL takes by weighing primary crystallization crystal and the methanol-water mixed solvent that step 1 obtains again; After the stirring and dissolving; To be cooled to temperature be 0 ℃～10 ℃ and keep 8h～12h; Filter; Obtain methanol-water mixed solvent mother liquor and solid formation; With solid formation with the drip washing of methanol-water mixed solvent; Being placed on vacuum tightness then is 0.085MPa～0.095MPa; Temperature is vacuum-drying 4h～8h under 40 ℃～60 ℃ the condition; Obtain 2, the pure article of 4-di-(1-phenylisopropyl) phenol.
To be purified 2 in the step 1 of the present invention, 4-di-(1-phenylisopropyl) phenol crude product comprises 2,4-di-(1-phenylisopropyl) phenol, 2-cumylphenol, 4-cumylphenol, 2,4, and the polymer of 6-three cumylphenols and alpha-methyl styrene, content of impurities is lower than 20%.Utilize in the crystal of gained behind the sherwood oil recrystallization and contain 2,4-di-(1-phenylisopropyl) phenol, 2-cumylphenol and 4-cumylphenol are white needle-like crystals; Carry out recrystallization with the methanol-water mixed solvent, remove 2-cumylphenol and 4-cumylphenol, obtain white needle-like crystals 2, the pure article of 4-di-(1-phenylisopropyl) phenol.Through twice recrystallization of step 1 and step 2, can obtain with the liquid chromatographic detection quality purity greater than 99% 2, the pure article of 4-di-(1-phenylisopropyl) phenol; Through behind twice recrystallization 2, the extraction rate of 4-di-(1-phenylisopropyl) phenol is 70%～85% (mass percent).Utilize twice recrystallization purifying process obviously to simplify, be applicable to suitability for industrialized production.
Embodiment
Embodiment one: this embodiment utilizes secondary recrystallization to purify 2; The method of 4-di-(1-phenylisopropyl) phenol is carried out according to the following steps: one; Sherwood oil recrystallization: by to be purified 2; The ratio of 4-di-(1-phenylisopropyl) phenol crude product and sherwood oil is that 1g: 1.2mL～3mL takes by weighing to be purified 2; 4-di-(1-phenylisopropyl) phenol crude product and sherwood oil; With to be purified 2; 4-di-(1-phenylisopropyl) phenol crude product joins in the sherwood oil; After the stirring and dissolving; To be cooled to temperature be 0 ℃～10 ℃ and keep 8h～12h; Filter; Obtain sherwood oil mother liquor and solid formation; With solid formation sherwood oil drip washing; Being placed on vacuum tightness then is 0.085MPa～0.095MPa; Temperature is vacuum-drying 4h～6h under 40 ℃～60 ℃ the condition, obtains the primary crystallization crystal; Two; The methanol-water recrystallization: by the volume ratio of methyl alcohol and water is to measure first alcohol and water and mix at 6～9: 1; Obtain the methanol-water mixed solvent; Ratio by primary crystallization crystal and methanol-water mixed solvent is that 1g: 1mL～3mL takes by weighing primary crystallization crystal and the methanol-water mixed solvent that step 1 obtains again; After the stirring and dissolving; To be cooled to temperature be 0 ℃～10 ℃ and keep 8h～12h; Filter; Obtain methanol-water mixed solvent mother liquor and solid formation; With solid formation with the drip washing of methanol-water mixed solvent; Being placed on vacuum tightness then is 0.085MPa～0.095MPa; Temperature is vacuum-drying 4h～8h under 40 ℃～60 ℃ the condition; Obtain 2, the pure article of 4-di-(1-phenylisopropyl) phenol.
In the step 1 is that impurity with the solid formation surface attachment rinses out with sherwood oil with solid formation with the purpose of sherwood oil drip washing;
In the step 2 is that impurity with the solid formation surface attachment rinses out with the methanol-water mixed solvent with solid formation with methanol-water mixed solvent drip washing purpose.
To be purified 2 in the step 1 of this embodiment, 4-di-(1-phenylisopropyl) phenol crude product comprises 2,4-di-(1-phenylisopropyl) phenol, 2-cumylphenol, 4-cumylphenol, 2,4, and the polymer of 6-three cumylphenols and alpha-methyl styrene, content of impurities is lower than 20%.Utilize in the crystal of gained behind the sherwood oil recrystallization and contain 2,4-di-(1-phenylisopropyl) phenol, 2-cumylphenol and 4-cumylphenol are white needle-like crystals; Carry out recrystallization with the methanol-water mixed solvent, remove 2-cumylphenol and 4-cumylphenol, obtain white needle-like crystals 2, the pure article of 4-di-(1-phenylisopropyl) phenol.Through twice recrystallization of step 1 and step 2, can obtain with the liquid chromatographic detection quality purity greater than 99% 2, the pure article of 4-di-(1-phenylisopropyl) phenol; Through behind twice recrystallization 2, the extraction rate of 4-di-(1-phenylisopropyl) phenol is 70%～85% (mass percent).Utilize twice recrystallization purifying process obviously to simplify, be applicable to suitability for industrialized production.
Embodiment two: what this embodiment and embodiment one were different is: to be purified 2 in the step 1,4-di-(1-phenylisopropyl) phenol crude product is 1g: 1.5mL～2.8mL with the ratio of sherwood oil.Other is identical with embodiment one.
Embodiment three: what this embodiment and embodiment one were different is: to be purified 2 in the step 1,4-di-(1-phenylisopropyl) phenol crude product is 1g: 2.0mL with the ratio of sherwood oil.Other is identical with embodiment one.
Embodiment four: what this embodiment was different with one of embodiment one to three is: cooling temperature is that 2 ℃～8 ℃, cooling time are 8.5h～11.5h in the step 1.Other is identical with one of embodiment one to three.
Embodiment five: what this embodiment was different with one of embodiment one to three is: cooling temperature is that 5 ℃, cooling time are 10h in the step 1.Other is identical with one of embodiment one to three.
Embodiment six: what this embodiment was different with one of embodiment one to five is: in the step 1 vacuum drying vacuum tightness be 0.087MPa～0.093MPa, temperature be 43 ℃～57 ℃, be 4.5h～5.5h time of drying.Other is identical with one of embodiment one to five.
Embodiment seven: what this embodiment was different with one of embodiment one to five is: in the step 1 vacuum drying vacuum tightness be 0.090MPa, temperature be 50 ℃, be 5h time of drying.Other is identical with one of embodiment one to five.
Embodiment eight: what this embodiment was different with one of embodiment one to seven is: be to measure first alcohol and water and mix at 6.3～8.7: 1 by the volume ratio of methyl alcohol and water in the step 2, obtain the methanol-water mixed solvent.Other is identical with one of embodiment one to seven.
Embodiment nine: what this embodiment was different with one of embodiment one to seven is: be to measure first alcohol and water at 7.5: 1 and mix by the volume ratio of methyl alcohol and water in the step 2, obtain the methanol-water mixed solvent.Other is identical with one of embodiment one to seven.
Embodiment ten: what this embodiment was different with one of embodiment one to nine is: the primary crystallization crystal is 1g: 1.5mL～2.5mL with the ratio of methanol-water mixed solvent in the step 2.Other is identical with one of embodiment one to nine.
Embodiment 11: what this embodiment was different with one of embodiment one to nine is: the primary crystallization crystal is 1g: 2.0mL with the ratio of methanol-water mixed solvent in the step 2.Other is identical with one of embodiment one to nine.
Embodiment 12: what this embodiment was different with one of embodiment one to 11 is: cooling temperature is that 2 ℃～8 ℃, cooling time are 8.5h～11.5h in the step 2.Other is identical with one of embodiment one to 11.
Embodiment 13: what this embodiment was different with one of embodiment one to 11 is: cooling temperature is that 5 ℃, cooling time are 10h in the step 2.Other is identical with one of embodiment one to 11.
Embodiment 14: what this embodiment was different with one of embodiment one to 13 is: vacuum drying vacuum tightness is that 0.087MPa～0.093MPa, temperature are that 42 ℃～58 ℃, time of drying are 4.2h～7.5h in the step 2.Other is identical with one of embodiment one to 13.
Embodiment 15: what this embodiment was different with one of embodiment one to 13 is: vacuum drying vacuum tightness is that 0.090MPa, temperature are that 50 ℃, time of drying are 6h in the step 2.Other is identical with one of embodiment one to 13.
Embodiment 16: this embodiment utilizes recrystallization to purify 2; The method of 4-di-(1-phenylisopropyl) phenol is carried out according to the following steps: one; The sherwood oil recrystallization: take by weighing the 300g quality purity and be 86% to be purified 2; 4-di-(1-phenylisopropyl) phenol crude product and 450mL sherwood oil; With to be purified 2; 4-di-(1-phenylisopropyl) phenol crude product joins in the sherwood oil; After the stirring and dissolving; To be cooled to temperature be 3 ℃ and keep 10h; Filter; Obtain sherwood oil mother liquor and solid formation; Solid formation is leached the back with sherwood oil drip washing 2 times, and being placed on vacuum tightness again is 0.090MPa; Temperature is in 45 ℃ the vacuum drying oven dry 4 hours, obtains primary crystallization crystal 2 20g; Two, methanol-water recrystallization: measure 250mL methyl alcohol and 40mL distilled water; Obtain the methanol-water mixed solvent after mixing; The 220g primary crystallization crystal that step 1 is obtained adds in the methanol-water mixed solvent; Stirring and dissolving postcooling to temperature is 3 ℃ and keeps 10h; Filter; Obtain methanol-water mixed solvent mother liquor and solid formation; It is 7: 1 mixed solvent drip washing 2 times that solid formation is used the volume ratio of methyl alcohol and water; Be placed on vacuum tightness then and be 0.090MPa, temperature and be in 50 ℃ the vacuum drying oven dry 5 hours; Obtain 2, the pure article 206g of 4-di-(1-phenylisopropyl) phenol.
In this embodiment in the step 1 primary crystallization crystal detect with high performance liquid chromatography, wherein 2, the mass content of 4-di-(1-phenylisopropyl) phenol is 95.2%; Step 2 obtain 2, the pure article of 4-di-(1-phenylisopropyl) phenol detect with high performance liquid chromatography, its quality purity is 99.20%, step 2 obtain 2, it is to be purified 2 that the pure article of 4-di-(1-phenylisopropyl) phenol account for, 79.8% of 4-di-(1-phenylisopropyl) phenol crude product quality.
Embodiment 17: this embodiment utilizes recrystallization to purify 2; The method of 4-di-(1-phenylisopropyl) phenol is carried out according to the following steps: one; Sherwood oil recrystallization: take by weighing 300g purity and be to be purified 2 of 91% (quality); 4-di-(1-phenylisopropyl) phenol crude product and 400mL sherwood oil; With to be purified 2; 4-di-(1-phenylisopropyl) phenol crude product joins in the sherwood oil; After the stirring and dissolving; To be cooled to temperature be 2 ℃ and keep 10h; Filter; Obtain sherwood oil mother liquor and solid formation; With sherwood oil drip washing 2 times, being placed in vacuum tightness again is 0.090MPa with solid formation; Temperature is in 45 ℃ the vacuum drying oven dry 5 hours, obtains primary crystallization crystal 2 51g; Two, methanol-water recrystallization: measure 300mL methyl alcohol and 40mL distilled water; After mixing; The 251g primary crystallization crystal that step 1 is obtained joins in the mixed solvent of methanol-water; Stirring and dissolving postcooling to temperature is 2 ℃ and keeps 10h; Filter; Obtain methanol-water solvent mother liquor and solid formation; Solid formation is leached the back, and to use the volume ratio of 50mL methyl alcohol and water be 7: 1 mixed solvent drip washing 2 times; Be placed on vacuum tightness then and be 0.090MPa, temperature and be in 50 ℃ the vacuum drying oven dry 5 hours; Obtain 2, the pure article 215g of 4-di-(1-phenylisopropyl) phenol.
In this embodiment in the step 1 primary crystallization crystal detect with high performance liquid chromatography, wherein 2, the mass content of 4-di-(1-phenylisopropyl) phenol is 96.3%; Step 2 obtain 2, the pure article of 4-di-(1-phenylisopropyl) phenol detect with high performance liquid chromatography, its quality purity is 99.4%, step 2 obtain 2, it is to be purified 2 that the pure article of 4-di-(1-phenylisopropyl) phenol account for, 78.8% of 4-di-(1-phenylisopropyl) phenol crude product quality.
Embodiment 18: this embodiment utilizes recrystallization to purify 2; The method of 4-di-(1-phenylisopropyl) phenol is carried out according to the following steps: one; Sherwood oil recrystallization: take by weighing 500g purity and be to be purified 2 of 92% (quality); 4-di-(1-phenylisopropyl) phenol crude product and 650mL sherwood oil; With to be purified 2; 4-di-(1-phenylisopropyl) phenol crude product joins in the sherwood oil; After the stirring and dissolving; To be cooled to temperature be 2 ℃ and keep 10h; Filter; Obtain sherwood oil mother liquor and solid formation; With sherwood oil drip washing 2 times, being placed on vacuum tightness again is 0.090MPa with solid formation; Temperature is in 45 ℃ the vacuum drying oven dry 4 hours, obtains primary crystallization crystal 3 79g; Two, methanol-water recrystallization: the water of measuring 450mL methyl alcohol and 50mL; After mixing; The 379g primary crystallization crystal that step 1 is obtained joins in the mixed solvent of methanol-water; Stirring and dissolving postcooling to temperature is 2 ℃ and keeps 10h; Filter; Obtain methanol-water solvent mother liquor and solid formation; It is 7: 1 mixed solvent drip washing 2 times that solid formation is used the volume ratio of 100mL methyl alcohol and water; Be placed on vacuum tightness and be 0.090MPa, temperature and be in 50 ℃ of vacuum drying ovens dry 6 hours; Obtain 2, the pure article 340g of 4-di-(1-phenylisopropyl) phenol.
In this embodiment in the step 1 primary crystallization crystal detect with high performance liquid chromatography, wherein 2, the mass content of 4-di-(1-phenylisopropyl) phenol is 97.4%; Step 2 obtain 2, the pure article of 4-di-(1-phenylisopropyl) phenol detect with high performance liquid chromatography, its quality purity is 99.5%, step 2 obtain 2, it is to be purified 2 that the pure article of 4-di-(1-phenylisopropyl) phenol account for, 73.9% of 4-di-(1-phenylisopropyl) phenol crude product quality.
Embodiment 19: this embodiment utilizes recrystallization to purify 2; The method of 4-di-(1-phenylisopropyl) phenol is carried out according to the following steps: one; Sherwood oil recrystallization: take by weighing 300g purity and be to be purified 2 of 94% (quality); 4-di-(1-phenylisopropyl) phenol crude product and 360mL sherwood oil; With to be purified 2; 4-di-(1-phenylisopropyl) phenol crude product joins in the sherwood oil; After the stirring and dissolving; To be cooled to temperature be 1 ℃ and keep 10h; Filter; Obtain sherwood oil mother liquor and solid formation; With sherwood oil drip washing 2 times, being placed on vacuum tightness again is 0.090MPa with solid formation; Temperature is in 50 ℃ the vacuum drying oven dry 5 hours, obtains primary crystallization crystal 2 89g; Two, methanol-water recrystallization: the water of measuring 350mL methyl alcohol and 30mL; After mixing; The 289g primary crystallization crystal that step 1 is obtained joins in the mixed solvent of methanol-water; Stirring and dissolving postcooling to temperature is 1 ℃ and keeps 10h; Filter; Obtain methanol-water solvent mother liquor and solid formation; It is 7: 1 mixed solvent drip washing 2 times that solid formation is used the volume ratio of 100mL methyl alcohol and water; Be placed on vacuum tightness and be 0.090MPa, temperature and be in 50 ℃ of vacuum drying ovens dry 6 hours; Obtain 2, the pure article 237g of 4-di-(1-phenylisopropyl) phenol.
In this embodiment in the step 1 primary crystallization crystal detect with high performance liquid chromatography, wherein 2, the mass content of 4-di-(1-phenylisopropyl) phenol is 97.1%; Step 2 obtain 2, the pure article of 4-di-(1-phenylisopropyl) phenol detect with high performance liquid chromatography, its quality purity is 99.4%, step 2 obtain 2, it is to be purified 2 that the pure article of 4-di-(1-phenylisopropyl) phenol account for, 84.0% of 4-di-(1-phenylisopropyl) phenol crude product quality.
Claims (8)
1. utilize secondary recrystallization to purify 2; The method of 4-di-(1-phenylisopropyl) phenol; It is characterized in that utilizing secondary recrystallization to purify 2; The method of 4-di-(1-phenylisopropyl) phenol is carried out according to the following steps: one; Sherwood oil recrystallization: by to be purified 2; The ratio of 4-di-(1-phenylisopropyl) phenol crude product and sherwood oil is that 1g: 1.2mL～3mL takes by weighing to be purified 2; 4-di-(1-phenylisopropyl) phenol crude product and sherwood oil; With to be purified 2; 4-di-(1-phenylisopropyl) phenol crude product joins in the sherwood oil; After the stirring and dissolving; To be cooled to temperature be 0 ℃～10 ℃ and keep 8h～12h; Filter, obtain sherwood oil mother liquor and solid formation, solid formation sherwood oil drip washing; Being placed on vacuum tightness then is 0.085MPa～0.095MPa; Temperature is vacuum-drying 4h～6h under 40 ℃～60 ℃ the condition, obtains the primary crystallization crystal; Two; The methanol-water recrystallization: by the volume ratio of methyl alcohol and water is to measure first alcohol and water and mix at 6～9: 1; Obtain the methanol-water mixed solvent; Ratio by primary crystallization crystal and methanol-water mixed solvent is that 1g: 1mL～3mL takes by weighing primary crystallization crystal and the methanol-water mixed solvent that step 1 obtains again; After the stirring and dissolving; To be cooled to temperature be 0 ℃～10 ℃ and keep 8h～12h; Filter; Obtain methanol-water mixed solvent mother liquor and solid formation; With solid formation with the drip washing of methanol-water mixed solvent; Being placed on vacuum tightness then is 0.085MPa～0.095MPa; Temperature is vacuum-drying 4h～8h under 40 ℃～60 ℃ the condition; Obtain 2, the pure article of 4-di-(1-phenylisopropyl) phenol.
2. the secondary recrystallization that utilizes according to claim 1 purifies 2, and the method for 4-di-(1-phenylisopropyl) phenol is characterized in that in the step 1 to be purified 2, and 4-di-(1-phenylisopropyl) phenol crude product is 1g: 1.5mL～2.8mL with the ratio of sherwood oil.
3. the secondary recrystallization that utilizes according to claim 1 and 2 purifies 2, and the method for 4-di-(1-phenylisopropyl) phenol is characterized in that in the step 1 that cooling temperature is that 2 ℃～8 ℃, cooling time are 8.5h～11.5h.
4. the secondary recrystallization that utilizes according to claim 1 and 2 purifies 2, the method for 4-di-(1-phenylisopropyl) phenol, it is characterized in that vacuum drying vacuum tightness in the step 1 be 0.087MPa～0.093MPa, temperature be 43 ℃～57 ℃, be 4.5h～5.5h time of drying.
5. the secondary recrystallization that utilizes according to claim 1 and 2 purifies 2, and the method for 4-di-(1-phenylisopropyl) phenol is characterized in that in the step 2 that volume ratio by methyl alcohol and water is to measure first alcohol and water and mix at 6.3～8.7: 1, obtains the methanol-water mixed solvent.
6. the secondary recrystallization that utilizes according to claim 1 and 2 purifies 2, and the method for 4-di-(1-phenylisopropyl) phenol is characterized in that the ratio of primary crystallization crystal and methanol-water mixed solvent is 1g: 1.5mL～2.5mL in the step 2.
7. the secondary recrystallization that utilizes according to claim 1 and 2 purifies 2, and the method for 4-di-(1-phenylisopropyl) phenol is characterized in that in the step 2 that cooling temperature is that 2 ℃～8 ℃, cooling time are 8.5h～11.5h.
8. the secondary recrystallization that utilizes according to claim 1 and 2 purifies 2, and the method for 4-di-(1-phenylisopropyl) phenol is characterized in that in the step 2 that vacuum drying vacuum tightness is that 0.087MPa～0.093MPa, temperature are that 42 ℃～58 ℃, time of drying are 4.2h～7.5h.
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| CN102690174A (en) * | 2012-06-26 | 2012-09-26 | 丁彦春 | Method for producing 4-cumylphenol and 2.4-dicumylphenol by using phenolic tar |
| CN107602353A (en) * | 2017-11-14 | 2018-01-19 | 郑程 | A kind of preparation method of antioxidant 264 |
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| US2714120A (en) * | 1950-05-23 | 1955-07-26 | Goodrich Co B F | Method of preparing aralkylated phenolic compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102690174A (en) * | 2012-06-26 | 2012-09-26 | 丁彦春 | Method for producing 4-cumylphenol and 2.4-dicumylphenol by using phenolic tar |
| CN102690174B (en) * | 2012-06-26 | 2016-01-06 | 丁彦春 | The method of 4-cumyl phenol and 2,4-dicumyl phenol is produced with phenolic tar |
| CN107602353A (en) * | 2017-11-14 | 2018-01-19 | 郑程 | A kind of preparation method of antioxidant 264 |
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