CN102079686A - Method for preparing 1,3,4,6-hexamethyl-1,2,4-tetrahydronaphthalene by continuous reaction under catalysis of ionic liquid - Google Patents
Method for preparing 1,3,4,6-hexamethyl-1,2,4-tetrahydronaphthalene by continuous reaction under catalysis of ionic liquid Download PDFInfo
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- CN102079686A CN102079686A CN2011100285695A CN201110028569A CN102079686A CN 102079686 A CN102079686 A CN 102079686A CN 2011100285695 A CN2011100285695 A CN 2011100285695A CN 201110028569 A CN201110028569 A CN 201110028569A CN 102079686 A CN102079686 A CN 102079686A
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Abstract
The invention discloses a method for preparing 1,3,4,6-hexamethyl-1,2,4-tetrahydronaphthalene by continuous reaction under catalysis of ionic liquid, which comprises the steps of: with acid room-temperature ionic liquid as a catalyst, cyclic hydrocarbon as a solvent, and cymene and olefin as raw materials, conducting alkylation reaction in the existence of a hydrogen transfer reagent, wherein the acid room-temperature ionic liquid catalyst is prepared by reaction of metal halide and alkyl-containing pyridine halogenated amine, alkyl-containing hydrogen halide of amine or alkyl-containing halogenated amine of imidazole. The method for preparing 1,3,4,6-hexamethyl-1,2,4-tetrahydronaphthalene has simple technical process, higher product selectivity and relatively considerable yield; the ionic liquid catalyst adopted in reaction can be separated from the reacting liquid easily and can be recycled; and the three industrial wastes are not generated in the technical process, thus the method for preparing 1,3,4,6-hexamethyl-1,2,4-tetrahydronaphthalene is a green and environment-friendly technique.
Description
Technical field
The invention belongs to the spices technical field, be specifically related to the method that a kind of ionic liquid-catalyzed successive reaction down prepares the hexamethyl tetralin.
Background technology
The hexamethyl tetralin is 1,1,3,4,4,6-vegolysen, 2,3, the 4-tetraline is called for short HMT, is the important intermediate of synthesizing musk tonalide spices, and tonalide is a kind of of musk odorant, have the intensive musky odor, its lasting is lasting, and the fragrance diffusibility is strong, its acid-and base-resisting in addition, good light stability, non-stimulated to human skin, good with other spices harmonicities, be the synthetic musk product that a kind of ideal has development potentiality very much, be widely used in perfume, makeup and the washing class perfume formulation.
Since research did not contain the tetralin class Moschus of nitro, people utilized different methods to successfully synthesize intermediate hexamethyl tetralin.(1) the eighties of last century sixties, in patent US 2851501 and US 3278621, disclose a kind of respectively by U.S. Polak spices company with the method that is the raw material synthesizing musk tonalide to different propylene toluene; (2) to disclose a kind of be the method for raw material synthesizing musk tonalide with the isopropyltoluene to U.S. Pat 2759022; (3) people such as Frank (Bull.Chem.Soc.Jpn.1993,66,125-129) with 3,3-dimethyl-1-butylene is a raw material, synthesizing musk tonalide under aluminum chloride-catalyzed; (4) Japanese Patent JP 6340559 discloses a kind ofly with isopropyltoluene and 2, and 3-dimethyl-1-butylene is a raw material, under solid-state Lewis acid (as iron(ic) chloride, aluminum chloride, zinc chloride etc.) catalysis, resets the method that makes tonalide by carbonium ion.
There is deficiency in force in above-mentioned synthetic method, is the synthetic method Grignard reagent of raw material with toluene, and cost is higher, and synthetic route is long, causes overall yield lower, is progressively replaced by additive method; In the method for many HMT of preparation, use the vitriol oil to make catalyzer, corrosive equipment, spent acid is difficult, and can cause the macromole by product to produce, and is unfavorable for industrial production; Present with 3,3-dimethyl-1-butylene or 2,3-dimethyl-1-butylene is that main raw material is by also existing severe reaction conditions in the synthetic method under the solid-state lewis acid catalyst catalysis of acidity, reaction preference is poor, reaction yield and productive rate are relatively low, the reaction level of automation is low, shortcomings such as reaction raw materials cost height.
Summary of the invention
Technical problem to be solved by this invention is at above-mentioned the deficiencies in the prior art, provides a kind of technological process simple, and the ionic liquid-catalyzed successive reaction down with high product selectivity and comparatively considerable yield prepares the method for hexamethyl tetralin.
For solving the problems of the technologies described above, the technical solution used in the present invention is: a kind of ionic liquid-catalyzed successive reaction down prepares the method for hexamethyl tetralin, it is characterized in that, this method is: with acid ionic liquid at room temperature is catalyzer, cyclic hydrocarbon is a solvent, cymene and alkene are raw material, carry out alkylated reaction in the presence of hydrogen transference reagent; Described acid ionic liquid at room temperature is a metal halide and the pyridine halogeno-amine that contains alkyl, the hydrohalogen of amine that contains alkyl or the imidazoles halogeno-amine prepared in reaction that contains alkyl form; The temperature of reaction of described alkylated reaction is-30 ℃～70 ℃, and reaction pressure is 1.0 * 10
3Pa～1.0 * 10
6Pa; The mass ratio of described isopropyl toluene and alkene is 1～100: 1, and the mass ratio of described isopropyl toluene and cyclic hydrocarbon is 1: 1～10, and described hydrogen transference reagent is tertiary butyl halogenide, and the mass ratio of hydrogen transference reagent and alkene is 0.5～5: 1.
Above-mentioned a kind of ionic liquid-catalyzed successive reaction down prepares the method for hexamethyl tetralin, the described pyridine halogeno-amine that contains alkyl, contain alkyl amine hydrohalogen or to contain the nitrogen-atoms of imidazoles halogeno-amine of alkyl saturated by four substituting groups, and at least one hydrogen atom and at least one alkyl substituent are arranged wherein; Described metal halide is the muriate of iron, copper, aluminium or zinc, perhaps is the bromide of iron, copper, aluminium or zinc.
Above-mentioned a kind of ionic liquid-catalyzed successive reaction down prepares the method for hexamethyl tetralin, and described alkyl substituent is methyl or ethyl.
Above-mentioned a kind of ionic liquid-catalyzed successive reaction down prepares the method for hexamethyl tetralin, and described muriate is iron trichloride, aluminum chloride or zinc chloride, and described bromide is iron bromide or cupric bromide.
Above-mentioned a kind of ionic liquid-catalyzed successive reaction down prepares the method for hexamethyl tetralin, and described tertiary butyl halogenide is tertiary butyl chloride or tert.-butyl bromide.
Above-mentioned a kind of ionic liquid-catalyzed successive reaction down prepares the method for hexamethyl tetralin, and described alkene is 3,3-dimethyl-1-butylene or 2,3-dimethyl-1-butylene.
Above-mentioned a kind of ionic liquid-catalyzed successive reaction down prepares the method for hexamethyl tetralin, and described cyclic hydrocarbon is hexanaphthene or suberane.
Above-mentioned a kind of ionic liquid-catalyzed successive reaction down prepares the method for hexamethyl tetralin, it is characterized in that, in the alkylation process, feeds nitrogen or exsiccant air in reaction system.
Above-mentioned a kind of ionic liquid-catalyzed successive reaction down prepares the method for hexamethyl tetralin, and the quality purity of described nitrogen is not less than 99.9%.
Above-mentioned a kind of ionic liquid-catalyzed successive reaction down prepares the method for hexamethyl tetralin, and described alkylated reaction mode is: with single kettle type or many stills formula successive reaction system, utilize nothing intermittently the continous way mode of production of static mixer for reactor.
The present invention compared with prior art has the following advantages:
1, technological process of the present invention is simple, have high product selectivity and comparatively considerable yield, prepared hexamethyl tetralin yield can reach 140%～260% of relative alkene quality, after simple rectifying, the quality purity of hexamethyl tetralin can reach more than 95%.
2, the ionic-liquid catalyst of the present invention's employing is easy to separate with reaction solution, reusable edible, and technological process does not produce three industrial wastes, is a kind of technology of environmental protection.
3, after the used ionic-liquid catalyst of the present invention was reused 10 times, the productive rate of hexamethyl tetralin and the selectivity of olefin isomerization did not descend, ion liquid regenerability excellence.
4, in the reaction process of the present invention, excellent selectivity under ionic liquid-catalyzed, with ion liquid relative slightly acidic effectively the inhibited reaction raw material olefin be not easy also to cause that owing to the steric hindrance of having living space causes increasing of addition reaction process by product the alkyl on the aromatic ring is reset and the transalkylation side reaction; The flowability of ionic-liquid catalyst makes the reaction can serialization production, when increasing substantially production efficiency, makes also that level of automation improves in the reaction process, and quality product is more stable.
Below by embodiment, technical scheme of the present invention is described in further detail.
Embodiment
1, the preparation of ionic-liquid catalyst
Embodiment 1
Under nitrogen protection, the N-Methylimidazole of 175.5kg n-propylcarbinyl chloride and 147.6kg is mixed to join in the autoclave, refluxed 48 hours cooling, standing demix down in 85 ℃～105 ℃; Topple over and remove the unreacted n-propylcarbinyl chloride in upper strata, use 500L ethyl acetate extraction 3 times; Add the isopyknic acetonitrile of 100L-ethyl acetate mixed solution then, shake up, in-20 ℃ freezing 12 hours down, obtain white crystals thing (thick product) after toppling over supernatant liquid, again with thick product in 90 ℃ of vacuum-dryings 6 hours, obtain 298.9kg chloro-1-alkyl-3-Methylimidazole ([C
4H
9Min] Cl).
Under nitrogen protection,, slowly join chloro-1-alkyl-3-Methylimidazole ([C of 117.7kg with the aluminum trichloride (anhydrous) 179.8kg that accurately measures
4H
9Min] Cl) in, and stir, a large amount of heat is emitted in reaction, and is too high for preventing temperature of reaction system, need carry out in the refrigerant cooling reactor is arranged in the preparation process, treat two kinds of materials mix all with extremely transparent after promptly obtain the ionic-liquid catalyst that uses among the present invention.
Embodiment 2
Under nitrogen protection, the 185kg bromination of n-butane mixed with the N-Methylimidazole of 147.6kg add in the reactor, sealing behind the nitrogen replacement three times kept 30 hours down in 85 ℃～105 ℃, obtained colourless alkyl bromide after the cooling; Precipitate recrystallization, suction filtration with ethyl acetate, with the ethyl acetate washing, vacuum-drying obtains 287kg bromo-1-alkyl-3-Methylimidazole ([C again
4H
9Min] Br).
Under nitrogen protection,, slowly join bromo-1-alkyl-3-Methylimidazole ([C of 120.5kg with the FERRIC CHLORIDE ANHYDROUS 183kg that accurately measures
4H
9Min] Br) in, and stir, a large amount of heat is emitted in reaction, and is too high for preventing temperature of reaction system, need carry out in the refrigerant cooling reactor is arranged in the preparation process, treat two kinds of materials mix all with extremely transparent after promptly obtain the ionic-liquid catalyst that uses among the present invention.
2, the preparation of hexamethyl tetralin
Embodiment 3
Ionic liquid with embodiment 1 preparation is a catalyzer, and hexanaphthene is a solvent, and cymene and 3,3-dimethyl-1-butylene are raw material, carry out alkylated reaction in the presence of hydrogen transference reagent tert.-butyl bromide; The temperature of reaction of described alkylated reaction is-30 ℃, and reaction pressure is 1.0 * 10
3Pa, isopropyl toluene and 3, the mass ratio of 3-dimethyl-1-butylene are 1: 1, and the mass ratio of isopropyl toluene and hexanaphthene is 1: 1, and hydrogen transference reagent tert.-butyl bromide and 3, the mass ratio of 3-dimethyl-1-butylene are 0.5: 1.
Detailed process is: use volume pump, in static mixer, squeeze into cymene, hexanaphthene, 3 in proportion respectively, the ionic-liquid catalyst of 3-dimethyl-1-butylene, tert.-butyl bromide and embodiment 1 preparation, wherein, the total length of static mixer is 3000mm, internal diameter 60mm, in adorn 50 unitary Kenics type flights and (divide left and right revolving alternately, twist 180 °), the length of every double helix sheet is 100mm, it is long, the footpath than add and approximate 1.88.Static mixer one side has 30 equally distributed side line arms, can be respectively applied for thermometric, sampling or side line turnover feed liquid.Regulate certain flow velocity and allow five thorough mixing and reactions in static mixer, temperature of reaction is-30 ℃, reacted material, enter in the sedimentation still, through ionic liquid after the sedimentation and the feed liquid layering of having reacted, ionic liquid is returned storage tank and is continued to participate in reaction, the feed liquid of having reacted is through the washing of washing still, after the rectifying, can obtain the hexamethyl tetralin of quality purity 99%, its quality is 150%～260% of a relative alkene quality.
Embodiment 4
Present embodiment is identical with the preparation method of embodiment 3, and wherein difference is: the temperature of reaction of described alkylated reaction is 20 ℃, and reaction pressure is 1.0 * 10
6Pa, isopropyl toluene and 3, the mass ratio of 3-dimethyl-1-butylene are 50: 1, the mass ratio of isopropyl toluene and hexanaphthene is 1: 5, hydrogen transference reagent tert.-butyl bromide and 3, the mass ratio of 3-dimethyl-1-butylene is 5: 1, feeds the exsiccant air in the reaction process in reaction system.
The quality purity of the hexamethyl tetralin of present embodiment preparation is 99%, and its quality is add 160%～260% of alkene quality.
Embodiment 5
Present embodiment is identical with the preparation method of embodiment 3, and wherein difference is: the temperature of reaction of described alkylated reaction is 70 ℃, and reaction pressure is 5.0 * 10
5Pa, isopropyl toluene and 3, the mass ratio of 3-dimethyl-1-butylene are 100: 1, and the mass ratio of isopropyl toluene and hexanaphthene is 1: 10, and hydrogen transference reagent tert.-butyl bromide and 3, the mass ratio of 3-dimethyl-1-butylene are 3: 1.
The quality purity of the hexamethyl tetralin of present embodiment preparation is 99%, and its quality is add 160%～260% of alkene quality.
Embodiment 6
Ionic liquid with embodiment 1 preparation is a catalyzer, and suberane is a solvent, and with cymene and 2,3-dimethyl-1-butylene is a raw material, carries out alkylated reaction in the presence of hydrogen transference reagent tertiary butyl chloride; The temperature of reaction of described alkylated reaction is 70 ℃, and reaction pressure is 1.0 * 10
6Pa, isopropyl toluene and 2, the mass ratio of 3-dimethyl-1-butylene are 50: 1, and the mass ratio of isopropyl toluene and suberane is 1: 10, and hydrogen transference reagent tertiary butyl chloride and 2, the mass ratio of 3-dimethyl-1-butylene are 5: 1.
Detailed process is: use volume pump, in venturi mixer, squeeze into isopropyl toluene in proportion respectively, 2,3-dimethyl-1-butylene, tertiary butyl chloride, the ionic liquid of suberane and embodiment 1 preparation, dispersion-mixing therein-reaction, enter in the static mixer again, reacted material, enter in the sedimentation still, through ionic liquid after the sedimentation and the feed liquid layering of having reacted, ionic liquid is returned storage tank and is continued to participate in reaction, and the feed liquid of having reacted is through the washing of washing still, after the rectifying, can obtain the hexamethyl tetralin of quality purity 99%, its quality is add 160%～260% of alkene quality.
Embodiment 7
Present embodiment is identical with the preparation method of embodiment 6, and wherein difference is: the temperature of reaction of described alkylated reaction is 20 ℃, and reaction pressure is 1.0 * 10
3Pa, isopropyl toluene and 2, the mass ratio of 3-dimethyl-1-butylene is 100: 1, the mass ratio of isopropyl toluene and suberane is 1: 1, hydrogen transference reagent tertiary butyl chloride and 2, the mass ratio of 3-dimethyl-1-butylene is 0.5: 1, and feeding quality purity to reaction system in the reaction process is 99.9% nitrogen.
The quality purity of the hexamethyl tetralin of present embodiment preparation is 99%, and its quality is add 160%～260% of alkene quality.
Embodiment 8
Present embodiment is identical with the preparation method of embodiment 6, and wherein difference is: the temperature of reaction of described alkylated reaction is-30 ℃, and reaction pressure is 5.0 * 10
5Pa, isopropyl toluene and 2, the mass ratio of 3-dimethyl-1-butylene are 1: 1, and the mass ratio of isopropyl toluene and suberane is 1: 5, and hydrogen transference reagent tertiary butyl chloride and 2, the mass ratio of 3-dimethyl-1-butylene are 3: 1.
The quality purity of the hexamethyl tetralin of present embodiment preparation is 99%, and its quality is add 160%～260% of alkene quality.
Embodiment 9
Ionic liquid with embodiment 2 preparations is a catalyzer, and hexanaphthene is a solvent, and with cymene and 2,3-dimethyl-1-butylene is a raw material, carries out alkylated reaction in the presence of hydrogen transference reagent tert.-butyl bromide; The temperature of reaction of described alkylated reaction is 20 ℃, and reaction pressure is 1.0 * 10
5Pa, isopropyl toluene and 2, the mass ratio of 3-dimethyl-1-butylene are 100: 1, and the mass ratio of isopropyl toluene and hexanaphthene is 1: 10, and hydrogen transference reagent tert.-butyl bromide and 2, the mass ratio of 3-dimethyl-1-butylene are 3: 1.
Detailed process is: use volume pump, in the reactor that band stirs, squeeze into isopropyl toluene, 2 respectively in proportion, the ionic liquid of 3-dimethyl-1-butylene, hexanaphthene, tert.-butyl bromide and embodiment 2 preparations, stirring reaction is opened on dnockout limit, limit, feed the circulating water cooling simultaneously in the reacting kettle jacketing, reaction process is to be undertaken by the material that constantly advances raw material and constantly go out to have reacted.The rectifying after washing and alkali cleaning of reacted material can obtain the hexamethyl tetralin of quality purity more than 95%, and its quality is add 140%～260% of alkene quality.
Embodiment 10
Present embodiment is identical with the preparation method of embodiment 9, and wherein difference is: the temperature of reaction of described alkylated reaction is 70 ℃, and reaction pressure is 1.0 * 10
3Pa, isopropyl toluene and 2, the mass ratio of 3-dimethyl-1-butylene is 50: 1, the mass ratio of isopropyl toluene and hexanaphthene is 1: 1, hydrogen transference reagent tert.-butyl bromide and 2, the mass ratio of 3-dimethyl-1-butylene is 0.5: 1, and feeding quality purity to reaction system in the reaction process is 99.99% nitrogen.
The quality purity of the hexamethyl tetralin of present embodiment preparation is more than 95%, and its quality is add 140%～260% of alkene quality.
Embodiment 11
Present embodiment is identical with the preparation method of embodiment 9, and wherein difference is: the temperature of reaction of described alkylated reaction is-30 ℃, and reaction pressure is 1.0 * 10
6Pa, isopropyl toluene and 2, the mass ratio of 3-dimethyl-1-butylene are 1: 1, and the mass ratio of isopropyl toluene and hexanaphthene is 1: 4, and hydrogen transference reagent tert.-butyl bromide and 2, the mass ratio of 3-dimethyl-1-butylene are 2: 1.
The quality purity of the hexamethyl tetralin of present embodiment preparation is more than 95%, and its quality is add 140%～260% of alkene quality.
The above; it only is preferred embodiment of the present invention; be not that the present invention is imposed any restrictions, everyly any simple modification that above embodiment did, change and equivalence changed, all still belong in the protection domain of technical solution of the present invention according to the technology of the present invention essence.
Claims (10)
1. an ionic liquid-catalyzed down successive reaction prepares the method for hexamethyl tetralin, it is characterized in that this method is: with acid ionic liquid at room temperature is catalyzer, and cyclic hydrocarbon is a solvent, cymene and alkene are raw material, carry out alkylated reaction in the presence of hydrogen transference reagent; Described acid ionic liquid at room temperature is a metal halide and the pyridine halogeno-amine that contains alkyl, the hydrohalogen of amine that contains alkyl or the imidazoles halogeno-amine prepared in reaction that contains alkyl form; The temperature of reaction of described alkylated reaction is-30 ℃～70 ℃, and reaction pressure is 1.0 * 10
3Pa～1.0 * 10
6Pa, the mass ratio of described isopropyl toluene and alkene are 1～100: 1, and the mass ratio of described isopropyl toluene and cyclic hydrocarbon is 1: 1～10, and described hydrogen transference reagent is tertiary butyl halogenide, and the mass ratio of hydrogen transference reagent and alkene is 0.5～5: 1.
2. a kind of ionic liquid-catalyzed successive reaction down according to claim 1 prepares the method for hexamethyl tetralin, it is characterized in that, the described pyridine halogeno-amine that contains alkyl, contain alkyl amine hydrohalogen or to contain the nitrogen-atoms of imidazoles halogeno-amine of alkyl saturated by four substituting groups, and at least one hydrogen atom and at least one alkyl substituent are arranged wherein; Described metal halide is the muriate of iron, copper, aluminium or zinc, perhaps is the bromide of iron, copper, aluminium or zinc.
3. a kind of ionic liquid-catalyzed successive reaction down according to claim 2 prepares the method for hexamethyl tetralin, it is characterized in that described alkyl substituent is methyl or ethyl.
4. a kind of ionic liquid-catalyzed successive reaction down according to claim 2 prepares the method for hexamethyl tetralin, it is characterized in that described muriate is iron trichloride, aluminum chloride or zinc chloride, and described bromide is iron bromide or cupric bromide.
5. a kind of ionic liquid-catalyzed successive reaction down according to claim 1 prepares the method for hexamethyl tetralin, it is characterized in that described tertiary butyl halogenide is tertiary butyl chloride or tert.-butyl bromide.
6. a kind of ionic liquid-catalyzed successive reaction down according to claim 1 prepares the method for hexamethyl tetralin, it is characterized in that described alkene is 3,3-dimethyl-1-butylene or 2,3-dimethyl-1-butylene.
7. a kind of ionic liquid-catalyzed successive reaction down according to claim 1 prepares the method for hexamethyl tetralin, it is characterized in that described cyclic hydrocarbon is hexanaphthene or suberane.
8. a kind of ionic liquid-catalyzed successive reaction down according to claim 1 prepares the method for hexamethyl tetralin, it is characterized in that, in the alkylation process, feeds nitrogen or exsiccant air in reaction system.
9. a kind of ionic liquid-catalyzed successive reaction down according to claim 8 prepares the method for hexamethyl tetralin, it is characterized in that the quality purity of described nitrogen is not less than 99.9%.
10. a kind of ionic liquid-catalyzed successive reaction down according to claim 1 prepares the method for hexamethyl tetralin, it is characterized in that, described alkylated reaction mode is: with single kettle type or many stills formula successive reaction system, utilize nothing intermittently the continous way mode of production of static mixer for reactor.
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| CN2011100285695A CN102079686A (en) | 2011-01-26 | 2011-01-26 | Method for preparing 1,3,4,6-hexamethyl-1,2,4-tetrahydronaphthalene by continuous reaction under catalysis of ionic liquid |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109369317A (en) * | 2018-12-18 | 2019-02-22 | 江西开源香料有限公司 | A kind of preparation method of tonalid intermediate HMT |
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| US3856875A (en) * | 1973-12-05 | 1974-12-24 | Givaudan Corp | Process for producing 1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronapthalene (hmt) |
| CN101003457A (en) * | 2006-01-19 | 2007-07-25 | 北京化工大学 | Method for preparing tri - isopropyl benzene by using catalyst of ion liquid |
-
2011
- 2011-01-26 CN CN2011100285695A patent/CN102079686A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3856875A (en) * | 1973-12-05 | 1974-12-24 | Givaudan Corp | Process for producing 1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronapthalene (hmt) |
| CN101003457A (en) * | 2006-01-19 | 2007-07-25 | 北京化工大学 | Method for preparing tri - isopropyl benzene by using catalyst of ion liquid |
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| 王春等: "六甲基萘满的合成优化", 《化学反应工程与工艺》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109369317A (en) * | 2018-12-18 | 2019-02-22 | 江西开源香料有限公司 | A kind of preparation method of tonalid intermediate HMT |
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Application publication date: 20110601 |