CN1541989A - Catalytic synthesis method of 1,3,3-trimethyl-1-phenyl indan - Google Patents
Catalytic synthesis method of 1,3,3-trimethyl-1-phenyl indan Download PDFInfo
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- CN1541989A CN1541989A CNA2003101083605A CN200310108360A CN1541989A CN 1541989 A CN1541989 A CN 1541989A CN A2003101083605 A CNA2003101083605 A CN A2003101083605A CN 200310108360 A CN200310108360 A CN 200310108360A CN 1541989 A CN1541989 A CN 1541989A
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Abstract
The catalytic synthesis process of 1, 3, 3-trimethyl-1-phenyl indane belongs to the field of organic chemical synthesis. 1, 3, 3-trimethyl-1-phenyl indane is catalytically synthesized with alpha-methyl styrene as material and under the catalysis of heteropoly acid or supported heteropoly acid. The said catalytic synthesis process is one simple green process and has the advantages of short reaction time, no use of volatile organic solvent, material converting rate of 100 %, yield of 95-100 %, low production cost, etc.
Description
Technical field
The present invention relates to 1,3, the process for catalytic synthesis of 3-trimethylammonium-1-phenyl indan is definitely said, relate to AMS cyclic dimer 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1, the process for catalytic synthesis of 3-trimethylammonium-3-phenyl indan belongs to organic chemistry synthetic technical field.
Background technology
Oligomerization can take place in alpha-methyl styrene (AMS) under acidic conditions, generate the linear dimer 2 of AMS, 4-phenylbenzene-1-Methyl-1-pentene and 2,4-phenylbenzene-1-methyl-2-amylene, cyclic dimer 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan and tripolymer 2,4,6-triphenyl-4,6-dimethyl-1-heptene etc.In these several products, AMS cyclic dimer 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan can be widely used in the softening agent, modifier of intermediate, plastics and the rubber of molecular weight regulator in synthetic of the material, polymkeric substance of ucon oil, fire retardant FR 1808 etc.AMS cyclic dimer 1 is synthesized in background technology catalysis, 3,3-trimethylammonium-1-phenyl indan, promptly 1,1, during 3-trimethylammonium-3-phenyl indan is raw material with alpha-methyl styrene (AMS) mostly, adopts activated clay, toluene sulfonic acide, MCM-41 mesopore molecular sieve, Zeo-karb Nafion etc. to make catalyzer.The shortcoming of this technology is to grow that to use volatile solvent, reaction yield and selectivity such as chloroform, ether lower in (3～12 hours), the reaction reaction times.
Summary of the invention
The purpose of this invention is to provide 1,3, the process for catalytic synthesis of 3-trimethylammonium-1-phenyl indan, this method time that responds lacks, and does not use volatile organic solvent, the advantage that productive rate and selectivity are high.
Technical scheme of the present invention is to be raw material with the alpha-methyl styrene, and under the catalytic condition of heteropolyacid or carried heteropoly acid, catalysis synthesizes 1,3,3-trimethylammonium-1-phenyl indan.
Now describe technical scheme of the present invention in detail.1,3, the process for catalytic synthesis of 3-trimethylammonium-1-phenyl indan, with the alpha-methyl styrene is raw material, it is characterized in that, with heteropolyacid or carried heteropoly acid is catalyzer, heteropolyacid is a phospho-molybdic acid, phospho-wolframic acid, silicomolybdic acid, a kind of in the silicotungstic acid, carried heteropoly acid is made of carrier and active ingredient, carrier is Y, X, M, β, Hydrogen-ZSM-5, MCM-41, a kind of in the SBA15 molecular sieve, active ingredient is a phospho-molybdic acid, phospho-wolframic acid, silicomolybdic acid, a kind of in the silicotungstic acid inserts fixed-bed reactor with catalyzer, catalyzer packing course height is 0.1～2 centimetre, control catalyst and material temperature are at 30～100 ℃, and feedstream catalysis behind catalyst layer synthesizes product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, air speed, promptly the quality of the reactant by the unit mass catalyzer is 1000～10000g/gh in the unit time
-1, feed stock conversion is 100%, productive rate is 95～100%.
Compare with background technology, the present invention has following outstanding effect:
1. the reaction times lacks, and air speed is 1000～10000g/gh
-1
2. without volatile organic solvent, make the greenization of production process realization solvent and catalyzer, improved the economic benefit and the social benefit of production process.
3. technology is simple, processing ease, and conversion of raw material is 100%, productive rate is 95～100%.
4. raw material is easy to get, and production cost is low.
Embodiment
Embodiment one
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 1 centimetre, and catalyzer is a phospho-molybdic acid, and control catalyst and material temperature are at 50 ℃, and air speed is 3382g/gh
-1, feedstream behind catalyzer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 96.5%.
Embodiment two
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 0.2 centimetre, and catalyzer is the X molecular sieve of load silicotungstic acid, and control catalyst and material temperature are at 100 ℃, and air speed is 8455g/gh
-1, feedstream behind catalyzer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 97.4%.
Embodiment three
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 2 centimetres, and catalyzer is the M molecular sieve of load phospho-molybdic acid, and control catalyst and material temperature are at 30 ℃, and air speed is 1008g/gh
-1, feedstream behind catalyst layer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 95.2%.
Embodiment four
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 0.5 centimetre, and catalyzer is a phospho-wolframic acid, and control catalyst and material temperature are at 40 ℃, and air speed is 5413g/gh
-1, feedstream behind catalyzer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 98.3%.
Embodiment five
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 0.3 centimetre, and catalyzer is the Hydrogen-ZSM-5 molecular sieve of load silicomolybdic acid, and control catalyst and material temperature are at 90 ℃, and air speed is 7852g/gh
-1, feedstream behind catalyzer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 95%.
Embodiment six
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 0.1 centimetre, and catalyzer is the Hydrogen-ZSM-5 molecular sieve of load phosphotungstic acid, and control catalyst and material temperature are at 80 ℃, and air speed is 9985g/gh
-1, feedstream behind catalyzer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 96.1%.
Embodiment seven
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 1.5 centimetres, and catalyzer is a silicomolybdic acid, and control catalyst and material temperature are at 45 ℃, and air speed is 2548g/gh
-1, feedstream behind catalyzer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 97.8%.
Embodiment eight
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 0.9 centimetre, and catalyzer is the SBA15 molecular sieve of load phosphotungstic acid, and control catalyst and material temperature are at 50 ℃, and air speed is 3685g/gh
-1, feedstream behind catalyzer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 100%.
Embodiment nine
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 1.7 centimetres, and catalyzer is the beta-molecular sieve of load phospho-molybdic acid, and control catalyst and material temperature are at 55 ℃, and air speed is 1667g/gh
-1, feedstream behind catalyst layer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 98.8%.
Embodiment ten
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 0.4 centimetre, and catalyzer is the MCM41 molecular sieve of load phosphotungstic acid, and control catalyst and material temperature are at 75 ℃, and air speed is 6823g/gh
-1, feedstream behind catalyzer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 95.7%.
Embodiment 11
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 0.6 centimetre, and catalyzer is a silicotungstic acid, and control catalyst and material temperature are at 60 ℃, and air speed is 4869g/gh
-1, feedstream behind catalyzer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 97.6%.
Embodiment 12
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 1.3 centimetres, and catalyzer is the SBA15 molecular sieve of load phospho-molybdic acid, and control catalyst and material temperature are at 30 ℃, and air speed is 2754g/gh
-1, feedstream behind catalyzer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 99.5%.
Embodiment 13
Catalyzer is inserted fixed-bed reactor, and catalyzer packing course height is 0.5 centimetre, and catalyzer is the Y molecular sieve of load silicomolybdic acid, and control catalyst and material temperature are at 70 ℃, and air speed is 5726g/gh
-1, feedstream behind catalyzer product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, feed stock conversion are 100%, productive rate is 96.9%.
Claims (1)
1. one kind 1,3, the process for catalytic synthesis of 3-trimethylammonium-1-phenyl indan, with the alpha-methyl styrene is raw material, it is characterized in that, with heteropolyacid or carried heteropoly acid is catalyzer, heteropolyacid is a phospho-molybdic acid, phospho-wolframic acid, silicomolybdic acid, a kind of in the silicotungstic acid, carried heteropoly acid is made of carrier and active ingredient, carrier is Y, X, M, β, Hydrogen-ZSM-5, MCM-41, a kind of in the SBA15 molecular sieve, active ingredient is a phospho-molybdic acid, phospho-wolframic acid, silicomolybdic acid, a kind of in the silicotungstic acid inserts fixed-bed reactor with catalyzer, catalyzer packing course height is 0.1～2 centimetre, control catalyst and material temperature are at 30～100 ℃, and feedstream catalysis behind catalyst layer synthesizes product 1,3,3-trimethylammonium-1-phenyl indan, promptly 1,1,3-trimethylammonium-3-phenyl indan, air speed, promptly the quality of the reactant by the unit mass catalyzer is 1000～10000g/gh in the unit time
-1, feed stock conversion is 100%, productive rate is 95～100%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2003101083605A CN1541989A (en) | 2003-11-04 | 2003-11-04 | Catalytic synthesis method of 1,3,3-trimethyl-1-phenyl indan |
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| CNA2003101083605A CN1541989A (en) | 2003-11-04 | 2003-11-04 | Catalytic synthesis method of 1,3,3-trimethyl-1-phenyl indan |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104058922A (en) * | 2013-03-19 | 2014-09-24 | 北京英力科技发展有限公司 | Synthetic method of 1,1,3-trimethyl-3-phenyl indane |
| CN107879871A (en) * | 2017-11-28 | 2018-04-06 | 无锡市佳盛高新改性材料有限公司 | The preparation method of α-methylstyrene cyclodimerization body |
| CN115011043A (en) * | 2022-06-13 | 2022-09-06 | 东南大学 | Ethylene propylene rubber insulating composition and preparation method thereof |
-
2003
- 2003-11-04 CN CNA2003101083605A patent/CN1541989A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104058922A (en) * | 2013-03-19 | 2014-09-24 | 北京英力科技发展有限公司 | Synthetic method of 1,1,3-trimethyl-3-phenyl indane |
| CN104058922B (en) * | 2013-03-19 | 2016-01-06 | 北京英力科技发展有限公司 | A kind of synthetic method of 1,1,3-trimethylammonium-3-phenyl indan |
| CN107879871A (en) * | 2017-11-28 | 2018-04-06 | 无锡市佳盛高新改性材料有限公司 | The preparation method of α-methylstyrene cyclodimerization body |
| CN115011043A (en) * | 2022-06-13 | 2022-09-06 | 东南大学 | Ethylene propylene rubber insulating composition and preparation method thereof |
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