CN101012155A - Method for synthesizing p-tert-bulylcatechol - Google Patents
Method for synthesizing p-tert-bulylcatechol Download PDFInfo
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- CN101012155A CN101012155A CN 200710034461 CN200710034461A CN101012155A CN 101012155 A CN101012155 A CN 101012155A CN 200710034461 CN200710034461 CN 200710034461 CN 200710034461 A CN200710034461 A CN 200710034461A CN 101012155 A CN101012155 A CN 101012155A
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Abstract
The invention discloses a synthesizing method of o-tert-butyl catechol (4-TBC), which is characterized by the following: reducing the quantity of catalyst without washing and neutralizing; rectifying to separate the rough product directly without wastewater.
Description
Technical field
The present invention relates to the method for p-ten.-butylcatechol (4-TBC).
Background technology
P-ten.-butylcatechol (4-TBC) is white or pale yellow crystals, be the high-efficiency polymerization inhibitor of monoolefine in distillation and storage and transport process, especially be applied to monomer best results such as vinylbenzene, divinyl, vinylchlorid, vinyl pyridine, vinylformic acid, methacrylic acid and ester class thereof, see that in the time of 60 ℃ polymerization inhibition effect comparison biphenol is high 25 times, be appointed as general stoppers such as vinylbenzene by U.S. ASTM, be the common employing in various countries.Herein, 4-TBC also can be used for polymkeric substance and oils such as polyethylene, polyhutadiene, nylon and synthetic rubber, lubricating oil, hexanolactam, the oxidation inhibitor of multiple compound such as maleic anhydride and metallic soap, also can be used as simultaneously the passivator of urethane catalyst, the stablizer of various organic compound, soil, agricultural chemicals.
The clear 49-127932 of Ri Tekai, the day special permission discloses the method that flat 2-152939 discloses pyrocatechol and iso-butylene prepared in reaction 4-TBC in the presence of oleum respectively, it promptly is catalyzer with the oleum, control sulfuric acid, iso-butylene and pyrocatechol amount ratio, reaction at a certain temperature, reacted with sodium hydroxide solution and neutralized, or add organic solvent extraction such as toluene, rectifying gets product, and above-mentioned synthetic method is only made catalyst with oleum, and reaction is fierce, be difficult to control, impurity is many, need neutralize simultaneously, the washing catalyzer brings problems such as acid-bearing wastewater processing and the loss of the adjacent benzene diester of raw material.
It is raw material that Chinese patent CN1303843A has reported with pyrocatechol, iso-butylene, it is synthetic to tert-butyl o base diphenol to adopt single solid acid or resin cation (R.C.) to make catalyzer, promptly also add pyrocatechol, iso-butylene in proportion in reaction, catalyst activated, 135 ± 5 ℃ of reactions, after the catalyst separating, rectifying gets product, above-mentioned synthetic method need be more with catalytic amount, having reacted catalyzer must separate effectively, and it is poor to select simultaneously, by product 3-TBC, 3.5-DTBC more, influence quality product and synthesis yield.
Having not yet to see with HL-8 is the processing method of the synthetic 4-TBC of catalyzer.
Summary of the invention
Technical characterictic of the present invention is to be catalyzer with HL-8, is raw material with pyrocatechol, iso-butylene, stirs down logical N after the pyrocatechol heat fused
2Catching up with air, is 1～6 hour in 100～150 ℃ of temperature of reaction, reaction times, and the insulation reaction time is 2 hours, and the control reaction pressure is that negative pressure is synthesized 4-TBC to the processing condition of pressure-fired.Catalyzer HL-8 of the present invention is the vitriol oil and mixture to methylsulphonic acid, and the HL-8 catalyst consumption is 0.05～1% of an adjacent basic diphenol weight.Pyrocatechol and iso-butylene mole proportioning are 1: 0.4～0.8.The pyrocatechol that reclaims can directly carry out sintetics again.
Synthetic method of the present invention has following advantage, with pyrocatechol and iso-butylene is raw material, synthesize butyl-catechol under catalyzer HL-8 catalysis, significantly reducing under the catalyst levels, reaction solution can directly carry out rectifying fractionation product, select high, by product 3-TBC, 3,5-DTBC is seldom, good product quality, the total recovery height has only a small amount of stillage residue burning disposal, has saved neutralization, the operating process of washing, the problem of environmental pollution that does not have phenolic wastewater to bring, also need not carry out catalytic separation and filter, technological operation is simple, the reaction conditions gentleness, production cost is low, is easy to industrial production.
Specific embodiments
Now the invention will be further described in conjunction with the embodiments:
Embodiment 1:
In having the 500ml device mouth flask of mechanical stirring, thermometer, airway and air set pipe, add 200g (1.8mol) pyrocatechol, after the heat fused, stir down logical N
2Caught up with air 10 minutes, add HL-8 catalyzer 0.2g then, begin to feed isobutene gas, simultaneously the prolong outlet is put the balloon sealing, and by the variation of pressure tap Monitoring systems reaction pressure, regulate iso-butylene ventilation speed, the control reaction pressure is that negative pressure is to pressure-fired, in 2 hours feeding 60g (1.05mol) left and right sides iso-butylenes, 120 ℃ of control reaction temperature, ventilation finishes, and insulation reaction 2 hours is converted into 63%, the direct rectifying of material promptly gets the p-ten.-butylcatechol product of content 〉=99%, yield 95%.
Reaction mixture gas chromatographic analysis (%) composed as follows:
Pyrocatechol 35.6
4-TBC 62.9
3.5-DTBC 0.4
Embodiment 2:
In having the 500ml device mouth flask of mechanical stirring, thermometer, airway and air set pipe, add 200g (1.8mol) pyrocatechol, after the heat fused, stir down logical N
2Caught up with air 10 minutes, add HL-8 catalyzer 0.1g then, begin to feed isobutene gas, simultaneously the prolong outlet is put the balloon sealing, and by the variation of pressure tap Monitoring systems reaction pressure, regulate iso-butylene ventilation speed, the control reaction pressure is that negative pressure is to pressure-fired, in 2 hours feeding 60g (1.05mol) left and right sides iso-butylenes, 120 ℃ of control reaction temperature, ventilation finishes, and insulation reaction 2 hours is converted into 58%, the direct rectifying of material promptly gets the p-ten.-butylcatechol product of content 〉=99%, yield 96%.
Reaction mixture gas chromatographic analysis (%) composed as follows:
Pyrocatechol 41.2
4-TBC 57.9
3.5-DTBC 0.8
Embodiment 3:
In having the 500ml device mouth flask of mechanical stirring, thermometer, airway and air set pipe, add 200g (1.8mol) pyrocatechol, after the heat fused, stir down logical N
2Caught up with air 10 minutes, add HL-8 catalyzer 2g then, begin to feed isobutene gas, simultaneously the prolong outlet is put the balloon sealing, and by the variation of pressure tap Monitoring systems reaction pressure, regulate iso-butylene ventilation speed, the control reaction pressure is that negative pressure is to pressure-fired, in 2 hours feeding 60g (1.05mol) left and right sides iso-butylenes, 120 ℃ of control reaction temperature, ventilation finishes, and insulation reaction 2 hours is converted into 79%, the direct rectifying of material promptly gets the p-ten.-butylcatechol product of content 〉=99%, yield 85%.
Reaction mixture gas chromatographic analysis (%) composed as follows:
Pyrocatechol 14.2
4-TBC 76.9
3.5-DTBC 8.8
Embodiment 4:
In having the 500ml device mouth flask of mechanical stirring, thermometer, airway and air set pipe, add 200g (1.8mol) pyrocatechol, after the heat fused, stir down logical N
2Caught up with air 10 minutes, add HL-8 catalyzer 0.2g then, begin to feed isobutene gas, simultaneously the prolong outlet is put the balloon sealing, and by the variation of pressure tap Monitoring systems reaction pressure, regulate iso-butylene ventilation speed, the control reaction pressure is that negative pressure is to pressure-fired, in 2 hours feeding 110g (1.9mol) left and right sides iso-butylenes, 120 ℃ of control reaction temperature, ventilation finishes, and insulation reaction 2 hours is converted into 98%, the direct rectifying of material promptly gets the p-ten.-butylcatechol product of content 〉=99%, yield 85%.
Reaction mixture gas chromatographic analysis (%) composed as follows:
Pyrocatechol 1.2
4-TBC 80.9
3.5-DTBC 8.8。
Claims (3)
1, the synthetic method of p-ten.-butylcatechol (4-TBC) is characterized in that with pyrocatechol, iso-butylene be raw material, is catalyzer with HL-8, stirs down logical N after the pyrocatechol heat fused
2Catching up with air, is 1～6 hour in 100～150 ℃ of temperature of reaction, reaction times, and the insulation reaction time is 2 hours, and the control reaction pressure is that negative pressure is synthesized 4-TBC to the processing condition of pressure-fired, and pyrocatechol and iso-butylene mole proportioning are 1: 0.4～0.8.
2, p-ten.-butylcatechol according to claim 1 (4-TBC) synthetic method is characterized in that described catalyzer HL-8 is the vitriol oil and mixture to methylsulphonic acid, and the HL-8 catalyst consumption is 0.05～1% of a pyrocatechol weight.
3, p-ten.-butylcatechol according to claim 1 (4-TBC) synthetic method is characterized in that reclaiming pyrocatechol and can directly carry out sintetics again.
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| CN 200710034461 CN101012155A (en) | 2007-02-15 | 2007-02-15 | Method for synthesizing p-tert-bulylcatechol |
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| CN 200710034461 CN101012155A (en) | 2007-02-15 | 2007-02-15 | Method for synthesizing p-tert-bulylcatechol |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102464574A (en) * | 2010-11-18 | 2012-05-23 | 中国石油化工股份有限公司 | Preparation method of p-alkyl catechol |
| CN103333053A (en) * | 2013-07-09 | 2013-10-02 | 湖南海利株洲精细化工有限公司 | Recovery method of 4-tert-butylcatechol raffinate |
| US20160230089A1 (en) * | 2013-09-19 | 2016-08-11 | Rhodia Operations | Composition preventing the polymerization of ethylenically unsaturated monomers and the removal thereof before polymerization |
| CN109053396A (en) * | 2018-09-20 | 2018-12-21 | 上海应用技术大学 | A method of o-ethoxyphenol is directly produced using ethylene |
| CN110041170A (en) * | 2019-04-09 | 2019-07-23 | 江西兄弟医药有限公司 | A kind of synthetic method of p-tert-Butylcatechol |
-
2007
- 2007-02-15 CN CN 200710034461 patent/CN101012155A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102464574A (en) * | 2010-11-18 | 2012-05-23 | 中国石油化工股份有限公司 | Preparation method of p-alkyl catechol |
| CN102464574B (en) * | 2010-11-18 | 2015-02-25 | 中国石油化工股份有限公司 | Preparation method of p-alkyl catechol |
| CN103333053A (en) * | 2013-07-09 | 2013-10-02 | 湖南海利株洲精细化工有限公司 | Recovery method of 4-tert-butylcatechol raffinate |
| US20160230089A1 (en) * | 2013-09-19 | 2016-08-11 | Rhodia Operations | Composition preventing the polymerization of ethylenically unsaturated monomers and the removal thereof before polymerization |
| US9605203B2 (en) * | 2013-09-19 | 2017-03-28 | Rhodia Operations | Composition preventing the polymerization of ethylenically unsaturated monomers and the removal thereof before polymerization |
| CN109053396A (en) * | 2018-09-20 | 2018-12-21 | 上海应用技术大学 | A method of o-ethoxyphenol is directly produced using ethylene |
| CN109053396B (en) * | 2018-09-20 | 2021-09-24 | 上海应用技术大学 | Method for directly producing o-ethoxyphenol by using ethylene |
| CN110041170A (en) * | 2019-04-09 | 2019-07-23 | 江西兄弟医药有限公司 | A kind of synthetic method of p-tert-Butylcatechol |
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