CN104926590A - Synthesis process of p-tart-butyltoluene - Google Patents
Synthesis process of p-tart-butyltoluene Download PDFInfo
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- CN104926590A CN104926590A CN201510282189.2A CN201510282189A CN104926590A CN 104926590 A CN104926590 A CN 104926590A CN 201510282189 A CN201510282189 A CN 201510282189A CN 104926590 A CN104926590 A CN 104926590A
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- butyltoluene
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- butylene
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Abstract
The invention discloses a synthesis process of p-tart-butyltoluene. The synthesis process is characterized in that the molar ratio of methylbenzene to isobutylene is 9:4, isobutene is introduced into a reaction tank to carry out alkylation reaction by three stages, the molar ratio of the isobutene introduced by three stages is 0.5:0.3:0.2 and the mass ratio of concentrated sulfuric acid to toluene sulfonic acid is 7-8:12. The synthesis process disclosed by the invention has the beneficial effects that novel protonic acid-p-toluene sulfonic acid is introduced as a catalyst, so that the alkylation reaction can be carried out under normal pressure, high-selectivity synthesis is realized, the conversion rate of methylbenzene is up to about 95%, the used amount of the concentrated sulfuric acid is reduced to one twelfth of the original amount, and the p-toluene sulfonic acid and concentrated sulfuric acid catalysts can be reused for multiple times which are 16 times or more than 16 times generally.
Description
Technical field
The present invention relates to a kind of synthesis technique of p-tert-butyltoluene.
Background technology
P-tert-butyltoluene is a kind of important chemical raw material and organic intermediate, its derivative p-t-Butylbenzaldehyde, p-tert-butyl benzoic acid, p-tert-butyl benzoic acid methyl esters, all there is purposes widely to tertiary butyl benzyl chlorine etc., can be widely used in poly-third nucleator, polychloroethylene heat stabilizer, machining of metals and lubrication oil additives, antioxidant, Synolac properties-correcting agent, soldering flux and fuel, sterilant and essence and flavoring agent and daily-use chemical industry industry.
According to the difference of raw material, p-tert-butyltoluene synthesis can be divided into following three routes: 1. toluene and iso-butylene alkylation process.The catalyzer that this method adopts has dense H2SO4, clay/unslaked lime etc., and reaction yield is more than 80%, and because iso-butylene raw material is rare and be difficult to transport, this method is only applicable to the enterprise that raw material iso-butylene is easy to get and produces; 2. toluene and trimethyl carbinol alkylation process, the catalyzer that this method adopts has urea/sulphur acid, TeCl4, BF3-polyphosphoric acid, HF/FSO3H etc., and reaction yield is between 44 ~ 85%; 3. toluene and tert-butyl chloride alkylation process, the catalyzer that this method uses has anhydrous AlCl3, Mo (CO) 6, (NaCl+AlCl3), and reaction yield is about 73%, because reaction has a large amount of HCl gas to produce, strict to equipment requirements.
The catalyzer major part adopted in above three kinds of synthetic methods belongs to liquid acid catalyst, there is etching apparatus serious, can not recycle, contaminate environment and the problems such as product selectivity difference.Because above various method exists above-mentioned different defect, limit the further application industrially of these methods and the renewal upgrading of production technology.
Summary of the invention
The technical problem to be solved in the present invention be overcome p-tert-butyltoluene in prior art synthesis technique to equipment corrosion, pollute large and need in high temperature reaction with pressure, the defect that dangerous hidden danger is large, provides a kind of synthesis technique of eco-friendly p-tert-butyltoluene.
In order to solve the problems of the technologies described above, the invention provides following technical scheme:
The synthesis technique of a kind of p-tert-butyltoluene of the present invention, comprises following configuration steps:
1), keep tank temperature 15 DEG C, in alkylated reaction tank, add toluene, the vitriol oil and toluene sulfonic acide;
2), control temperature at 20 ~ 22 DEG C, in retort, a point three phases passes into iso-butylene and carries out alkylated reaction, first stage 3 hours, second stage 5 hours, three phases 4 ~ 6 hours, obtained p-tert-butyltoluene.
Preferably, the mol ratio of toluene and iso-butylene is 9:4.
Further, the mol ratio entering iso-butylene passed into for three times is: 0.5:0.3:0.2.
Further, the mass ratio of the described vitriol oil and toluene sulfonic acide is 7 ~ 8:12.
Further, the consumption of the described vitriol oil and the mass ratio of described iso-butylene consumption are 3:80.
Preferably, the temperature of alkylated reaction controls at 21 ~ 22 DEG C.
The synthesis technique of p-tert-butyltoluene of the present invention, alkylated reaction can be carried out at normal pressure, realize the synthesis of highly selective, the transformation efficiency of toluene is up to about 85%, introducing novel protonic acid-p-methyl benzenesulfonic acid is catalyzer, being dropped to by the consumption of the vitriol oil is 1/12nd of former consumption, and p-methyl benzenesulfonic acid and concentrated sulfuric acid catalyst can repeatedly recycle, and generally can circulate more than 16 times.
Embodiment
Be described below in conjunction with to the preferred embodiments of the present invention, should be appreciated that preferred embodiment described herein is only for instruction and explanation of the present invention, is not intended to limit the present invention.
Embodiment 1
The synthesis technique of a kind of p-tert-butyltoluene of the present invention, comprises following configuration steps:
1), keep tank temperature 15 DEG C, in alkylated reaction tank, add toluene, the vitriol oil and toluene sulfonic acide; The mass ratio of the vitriol oil and toluene sulfonic acide is 7 ~ 8.
2), control temperature at 20 DEG C, in retort, point pass into iso-butylene for three times carry out alkylated reaction, the mol ratio of toluene and iso-butylene total amount is 9:4.
In retort, divide a three phases to pass into iso-butylene carry out alkylated reaction, first stage 3 hours, second stage 5 hours, three phases 4 hours, obtained p-tert-butyltoluene; The mol ratio entering iso-butylene passed into for three times is: 0.5:0.3:0.2.
The consumption of the described vitriol oil and the mass ratio of described iso-butylene consumption are 3:80.
The transformation efficiency of the present embodiment toluene is 80%.
Embodiment 2
The synthesis technique of a kind of p-tert-butyltoluene of the present invention, comprises following configuration steps:
1), keep tank temperature 15 DEG C, in alkylated reaction tank, add toluene, the vitriol oil and toluene sulfonic acide; The mass ratio of the vitriol oil and toluene sulfonic acide is 7 ~ 10.
2), control temperature at 22 DEG C, in retort, point pass into iso-butylene for three times carry out alkylated reaction, the mol ratio of toluene and iso-butylene total amount is 9:4.
In retort, divide a three phases to pass into iso-butylene carry out alkylated reaction, first stage 3 hours, second stage 5 hours, three phases 5 hours, obtained p-tert-butyltoluene; The mol ratio entering iso-butylene passed into for three times is: 0.5:0.3:0.2.
The consumption of the described vitriol oil and the mass ratio of described iso-butylene consumption are 3:80.
The transformation efficiency of the present embodiment toluene is 85%.
Embodiment 3
The synthesis technique of a kind of p-tert-butyltoluene of the present invention, comprises following configuration steps:
1), keep tank temperature 15 DEG C, in alkylated reaction tank, add toluene, the vitriol oil and toluene sulfonic acide; The mass ratio of the vitriol oil and toluene sulfonic acide is 7 ~ 12.
2), control temperature at 21 DEG C, in retort, point pass into iso-butylene for three times carry out alkylated reaction, the mol ratio of toluene and iso-butylene total amount is 9:4.
The in retort a point three phases pass into iso-butylene and carry out alkylated reaction, first stage 3 hours, second stage 5 hours, three phases 6 hours, obtained p-tert-butyltoluene; The mol ratio entering iso-butylene passed into for three times is: 0.5:0.3:0.2.
The consumption of the described vitriol oil and the mass ratio of described iso-butylene consumption are 3:80.
The transformation efficiency of the present embodiment toluene is 82.7%.
Last it is noted that the foregoing is only the preferred embodiments of the present invention, be not limited to the present invention, although with reference to previous embodiment to invention has been detailed description, for a person skilled in the art, it still can be modified to the technical scheme described in foregoing embodiments, or carries out equivalent replacement to wherein portion of techniques feature.Within the spirit and principles in the present invention all, any amendment done, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (6)
1. a synthesis technique for p-tert-butyltoluene, is characterized in that, comprises following configuration steps:
1), keep tank temperature 15 DEG C, in alkylated reaction tank, add toluene, the vitriol oil and toluene sulfonic acide;
2), control temperature at 20 ~ 22 DEG C, in retort, a point three phases passes into iso-butylene and carries out alkylated reaction, first stage 3 hours, second stage 5 hours, three phases 4 ~ 6 hours, obtained p-tert-butyltoluene.
2., as the synthesis technique by a kind of p-tert-butyltoluene according to claim 1, it is characterized in that, the mol ratio of toluene and iso-butylene is 9:4.
3., as the synthesis technique by a kind of p-tert-butyltoluene according to claim 1, it is characterized in that, the mol ratio entering iso-butylene passed into for three times is: 0.5:0.3:0.2.
4., as the synthesis technique by a kind of p-tert-butyltoluene according to claim 1, it is characterized in that, the mass ratio of the described vitriol oil and toluene sulfonic acide is 7 ~ 8:12.
5., as the synthesis technique by a kind of p-tert-butyltoluene according to claim 1, it is characterized in that, the consumption of the described vitriol oil and the mass ratio of described iso-butylene consumption are 3:80.
6., as the synthesis technique by a kind of p-tert-butyltoluene according to claim 1, it is characterized in that, the temperature of alkylated reaction controls at 21 ~ 22 DEG C.
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| CN201510282189.2A CN104926590A (en) | 2015-05-28 | 2015-05-28 | Synthesis process of p-tart-butyltoluene |
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| CN201510282189.2A CN104926590A (en) | 2015-05-28 | 2015-05-28 | Synthesis process of p-tart-butyltoluene |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669342A (en) * | 2015-12-30 | 2016-06-15 | 中国石油大学(华东) | Method of synthesizing p-tert-butyl toluene with caprolactam ionic liquid as catalyst |
| CN115770610A (en) * | 2021-09-08 | 2023-03-10 | 中国石油化工股份有限公司 | Method for producing p-tert-butyl toluene by catalysis of solid acid catalyst |
| CN115838315A (en) * | 2022-12-23 | 2023-03-24 | 常州瑞华化工工程技术股份有限公司 | Process for producing tert-butyl ethylbenzene by low aromatic-to-olefin ratio and tert-butyl ethylbenzene |
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| JPS4924934A (en) * | 1972-06-30 | 1974-03-05 | ||
| CN101648866A (en) * | 2009-09-18 | 2010-02-17 | 刘忠春 | Preparation technology of p-tert-butyl benzoic acid |
| 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 |
| CN103304450A (en) * | 2013-06-14 | 2013-09-18 | 杨锌荣 | Alkyl naphthalene polysulfonate and preparation method thereof |
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2015
- 2015-05-28 CN CN201510282189.2A patent/CN104926590A/en active Pending
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| JPS4924934A (en) * | 1972-06-30 | 1974-03-05 | ||
| CN101648866A (en) * | 2009-09-18 | 2010-02-17 | 刘忠春 | Preparation technology of p-tert-butyl benzoic acid |
| 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 |
| CN103304450A (en) * | 2013-06-14 | 2013-09-18 | 杨锌荣 | Alkyl naphthalene polysulfonate and preparation method thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669342A (en) * | 2015-12-30 | 2016-06-15 | 中国石油大学(华东) | Method of synthesizing p-tert-butyl toluene with caprolactam ionic liquid as catalyst |
| CN115770610A (en) * | 2021-09-08 | 2023-03-10 | 中国石油化工股份有限公司 | Method for producing p-tert-butyl toluene by catalysis of solid acid catalyst |
| CN115770610B (en) * | 2021-09-08 | 2024-02-13 | 中国石油化工股份有限公司 | Method for producing p-tert-butyl toluene by catalysis of solid acid catalyst |
| CN115838315A (en) * | 2022-12-23 | 2023-03-24 | 常州瑞华化工工程技术股份有限公司 | Process for producing tert-butyl ethylbenzene by low aromatic-to-olefin ratio and tert-butyl ethylbenzene |
| CN115838315B (en) * | 2022-12-23 | 2023-11-17 | 常州瑞华化工工程技术股份有限公司 | Process for producing tert-butylethylbenzene by low aromatic alkene ratio and tert-butylethylbenzene |
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Application publication date: 20150923 |