CN1228291C - Process for synthesizing 1-phenyl-1-dimethyl phenyl ethane - Google Patents
Process for synthesizing 1-phenyl-1-dimethyl phenyl ethane Download PDFInfo
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- CN1228291C CN1228291C CN 02135257 CN02135257A CN1228291C CN 1228291 C CN1228291 C CN 1228291C CN 02135257 CN02135257 CN 02135257 CN 02135257 A CN02135257 A CN 02135257A CN 1228291 C CN1228291 C CN 1228291C
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- phenyl
- dimethyl benzene
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Abstract
The present invention relates to a synthetic method for 1-phenyl-1-dimethyl phenyl ethane which is a product obtained from the reaction of dimethyl benzene and styrene used as raw materials. The synthetic method is characterized in that solid superstrong acid is used as a catalyst, and after reaction, the catalyst is removed by filtration; a filter liquid obtained from the filtration is distilled under ordinary pressure to make excessive dimethyl benzene removed; distillation by pressure reduction is carried out after cooling, and a product is distilled off. In the present invention, a catalyst has high activity and few dosages, and the catalyst can be repeatedly used and can be recovered to original activity by activation after being repeatedly used for many times without environmental pollution; in addition, the catalyst can be easily separated from a product, the catalytic principle is different from that of protonic acid, the catalyst has no corrosion to devices and is convenient and safe to operate, and a yield is above 95%.
Description
(1) invention field: the present invention relates to the synthetic method of a kind of 1-phenyl-1-3,5-dimethylphenyl ethane, especially a kind of is the synthetic method of the 1-phenyl-1-3,5-dimethylphenyl ethane of catalyzer with the solid super-strong acid.
(2) background technology: at present, Nippon Petrochemicals Company, Limited and domestic manufacturer all adopt the vitriol oil to make the synthetic 1-phenyl of catalyzer-1-3,5-dimethylphenyl ethane.Its method is to add dimethyl benzene in reactor, and electronic stirring is cooled off 0～5 ℃, then the drip styrene and the vitriol oil in the frozen water.The vinylbenzene and the vitriol oil drip simultaneously, and rate of addition is controlled at vinylbenzene: vitriol oil ≈ 2: 1, keep whole temperature at 0～5 ℃.Drip off the back temperature and reduced naturally by constant, reaction is finished.Reaction mixture is changeed in people's separating funnel, divide and remove the vitriol oil, use alkali cleaning then, be washed till neutrality, wash with water, be dried to clarification with Calcium Chloride Powder Anhydrous, then, boil off dimethyl benzene earlier, product is collected in underpressure distillation again.Productive rate is up to 85%.Shortcoming is that stirring is inhomogeneous, causes charing.Though the vitriol oil has advantages of high catalytic activity, cheap, severe corrosion equipment, the loaded down with trivial details serious three wastes of post-reaction treatment operation, side reaction is many, and product separates difficult, and color and luster is bad.And vitriol oil consumption is big, can not reuse, and both wastes, again contaminate environment.
(3) summary of the invention: the objective of the invention is to overcome the deficiency of above-mentioned prior art and provide a kind of is catalyzer with the solid super-strong acid, catalyst levels is few, can reuse, and catalyzer and product are easily separated the synthetic method of the 1-phenyl that output is high-1-3,5-dimethylphenyl ethane.
Purpose of the present invention can reach by following measure: the synthetic method of 1-phenyl-1-3,5-dimethylphenyl ethane, be to make the raw material reaction products therefrom with dimethyl benzene and vinylbenzene, it is characterized in that with solid super-strong acid as catalyzer, after reaction finishes, remove by filter catalyzer, filtration gained filtrate is distilled under normal pressure remove excessive dimethyl benzene.After the cooling, carry out underpressure distillation, steam product.The volume ratio of dimethyl benzene and vinylbenzene reaction is 5～15: 1, and temperature of reaction is a reflux temperature, 3～4 hours reaction times.The volume ratio of dimethyl benzene and vinylbenzene reaction is 7.5～10: 1.Solid super acid catalyst is SO
4 2-/ M
xO
y(X is 1 or 2, and Y is 2 or 3) or SO
4 2-/ M
xO
y-N
X 'O
Y 'The solid super-strong acid of (X ' be 1 or 2, Y ' is 2 or 3) type.
Compared with the prior art the present invention has following positively effect: owing to use super acids as catalyzer, super acids is stronger than strong protonic acid (as sulfuric acid) acidity, and its acid maximum can reach 100%H
2SO
4More than 10,000 times, the catalytic activity height, consumption is few, and can reuse, and repeats repeatedly that the back is activated can recover original activity again, there is not environmental pollution, and catalyzer and product are easily separated, and Catalysis Principles is different with protonic acid, and equipment is not corroded, easy and safe to operate, output is up to more than 95%.
(4) embodiment: in reactor, add dimethyl benzene and catalyzer, heating makes the dimethyl benzene boiling, slowly splash into the vinylbenzene of certain volume, dimethyl benzene and cinnamic volume ratio are 5-15: 1, catalyst levels is the 1%-3% of the volume that always feeds intake, reacted 3-4 hour, and removed by filter catalyzer.The filtrate of filtering gained distilled under normal pressure remove excessive dimethyl benzene.After the cooling, carry out underpressure distillation, under the temperature of the pressure of 380-450 handkerchief and 135-170 ℃, collect fraction, be 1-phenyl-1-3,5-dimethylphenyl ethane.Reaction formula is:
Embodiment 1, adds dimethyl benzene and catalyst Fe in reactor
2O
3-SO
4 2-, heating makes the dimethyl benzene boiling, slowly splashes into the vinylbenzene of certain volume in 2 hours, and dimethyl benzene and cinnamic volume ratio are 5: 1, and catalyst levels reacted 1 hour for 1% of the volume that always feeds intake, and removed by filter catalyzer.The filtrate of filtering gained distilled under normal pressure remove excessive dimethyl benzene.After the cooling, carry out underpressure distillation, under the temperature of the pressure of 380 handkerchiefs and 135-150 ℃, collect fraction, be 1-phenyl-1-3,5-dimethylphenyl ethane.
Embodiment 2, add dimethyl benzene and catalyzer ZrO in reactor
2/ SO
4 2-, heating makes the dimethyl benzene boiling, slowly splashes into the vinylbenzene of certain volume in 2 hours, and dimethyl benzene and cinnamic volume ratio are 15: 1, and catalyst levels reacted 2 hours for 3% of the volume that always feeds intake, and removed by filter catalyzer.The filtrate of filtering gained distilled under normal pressure remove excessive dimethyl benzene.After the cooling, carry out underpressure distillation, under the temperature of the pressure of 450 handkerchiefs and 135-170 ℃, collect fraction, be 1-phenyl-1-3,5-dimethylphenyl ethane.
Embodiment 3, add dimethyl benzene and catalyzer TiO in reactor
2/ SO
4 2-, heating makes the dimethyl benzene boiling, slowly splashes into the vinylbenzene of certain volume in 1.5 hours, and dimethyl benzene and cinnamic volume ratio are 10: 1, and catalyst levels reacted 1.5 hours for 2% of the volume that always feeds intake, and removed by filter catalyzer.The filtrate of filtering gained distilled under normal pressure remove excessive dimethyl benzene.After the cooling, carry out underpressure distillation, under the temperature of the pressure of 400 handkerchiefs and 135-170 ℃, collect fraction, be 1-phenyl-1-3,5-dimethylphenyl ethane.
Embodiment 4, add dimethyl benzene and catalyst S O in reactor
4 2-/ TiO
2-Fe
2O
3, heating makes the dimethyl benzene boiling, slowly splashes into the vinylbenzene of certain volume in 1.5 hours, and dimethyl benzene and cinnamic volume ratio are 7.5: 1, and catalyst levels reacted 2 hours for 1% of the volume that always feeds intake, and removed by filter catalyzer.The filtrate of filtering gained distilled under normal pressure remove excessive dimethyl benzene.After the cooling, carry out underpressure distillation, under the temperature of the pressure of 400 handkerchiefs and 135-170 ℃, collect fraction, be 1-phenyl-1-3,5-dimethylphenyl ethane.
Claims (3)
1, the synthetic method of 1-phenyl-1-3,5-dimethylphenyl ethane is to make the raw material reaction products therefrom with dimethyl benzene and vinylbenzene, it is characterized in that using solid super-strong acid SO
4 2-/ M
xO
yOr SO
4 2-/ M
xO
Y-N
X 'O
Y ', wherein M is zirconium, titanium or iron, and N is an iron, and X is 1 or 2, and Y is 2 or 3, X ' is 1 or 2, and Y ' is 2 or 3, as catalyzer, after reaction finishes, removes by filter catalyzer, the filtrate of filtering gained distilled under normal pressure remove excessive dimethyl benzene, after the cooling, carry out underpressure distillation, steam product.
2, according to the synthetic method of the described 1-phenyl of claim 1-1-3,5-dimethylphenyl ethane, it is characterized in that the volume ratio of dimethyl benzene and vinylbenzene reaction is 5～15: 1, temperature of reaction is a reflux temperature, 3～4 hours reaction times.
3,, it is characterized in that the volume ratio of dimethyl benzene and vinylbenzene reaction is 7.5～10: 1 according to the synthetic method of claim 1 or 2 described 1-phenyl-1-3,5-dimethylphenyl ethane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 02135257 CN1228291C (en) | 2002-07-07 | 2002-07-07 | Process for synthesizing 1-phenyl-1-dimethyl phenyl ethane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 02135257 CN1228291C (en) | 2002-07-07 | 2002-07-07 | Process for synthesizing 1-phenyl-1-dimethyl phenyl ethane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1511812A CN1511812A (en) | 2004-07-14 |
| CN1228291C true CN1228291C (en) | 2005-11-23 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 02135257 Expired - Fee Related CN1228291C (en) | 2002-07-07 | 2002-07-07 | Process for synthesizing 1-phenyl-1-dimethyl phenyl ethane |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101648841A (en) * | 2008-08-14 | 2010-02-17 | 新疆大学 | Method for catalytic synthesis of diaryl ethane |
| CN101898931A (en) * | 2009-05-25 | 2010-12-01 | 新疆大学 | Method for catalyzing and synthesizing diphenylethane with molecular sieves Al-MCM-41 |
| CN102603451A (en) * | 2012-02-28 | 2012-07-25 | 南开大学 | Method for preparing diphenylethane catalyzed by mixed liquid of concentrated sulfuric acid and ion liquid |
-
2002
- 2002-07-07 CN CN 02135257 patent/CN1228291C/en not_active Expired - Fee Related
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