CN101391937A - Method for catalyzed synthesis of 2,6-dimethylnaphthalene by using ion liquid - Google Patents
Method for catalyzed synthesis of 2,6-dimethylnaphthalene by using ion liquid Download PDFInfo
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- CN101391937A CN101391937A CNA2008101374783A CN200810137478A CN101391937A CN 101391937 A CN101391937 A CN 101391937A CN A2008101374783 A CNA2008101374783 A CN A2008101374783A CN 200810137478 A CN200810137478 A CN 200810137478A CN 101391937 A CN101391937 A CN 101391937A
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- dimethylnaphthalene
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Abstract
The invention discloses a method for preparing 2, 6-dimethylnaphthalene by ionic liquid catalysis, relating to a method for preparing dimethylnaphthalene by ionic liquid catalysis. The invention solves the problems in the existing method for preparing 2, 6-dimethylnaphthalene that: the process is complex, byproducts are numerous, the selectivity of the 2, 6-dimethylnaphthalene is poor and separating the 2, 6-dimethylnaphthalene from products is difficult. The method comprises the following steps: methylnaphthalene, an alkyl transfer agent and a solvent are mixed; then, the ionic liquid catalyst occupying 10 to 75 percent of the total weight of the mixed solution is added in the mixed solution; reaction is carried out under the protection of inert gas at the temperature of 10 to 50 DEG C for 0.5 to 8h; after that, the mixed solution is cooled to room temperature; and the 2, 6-dimethylnaphthalene is obtained through separation after the decantation of an upper layer of the reaction solution in layered reaction solution. The selectivity of the 2, 6-dimethylnaphthalene obtained by adopting the method is 66.4 to 100 percent; no multi-methylnaphthalene byproducts such as trimethyl-naphthalene and the like are generated; and the method for preparing 2, 6-dimethylnaphthalene has simple process and low production cost.
Description
Technical field
The present invention relates to a kind of ionic liquid-catalyzed method for preparing dimethylnaphthalene.
Background technology
2, the 6-dimethylnaphthalene (2,6-DMN) by oxidation obtain 2, the 6-naphthalic acid is a critical materials of producing new polyester macromolecular material PEN (PEN).The PEN high comprehensive performance, it not only has the characteristic of polyethylene terephthalate (PET), and nearly all performance all is better than PET.Being widely used in industries such as process industry, building slab, fiber, insulating material, film, disk, beverage bottle, food packing film, space flight and aviation and nuclear power material, is one of macromolecular material that Application and Development was the fastest in nearly 10 years.
U.S. BP Amoco company realizes 2 at present in the world the earliest, the enterprise of 6-DMN large-scale production, be with dimethylbenzene be raw material through the four-step reaction Synthetic 2,6-DMN (Kyuko Y.et al., US 5396007; L.D.Lillwitz, Appl.Catal.A:Gen., 2001,221:337-358), but owing to complex technical process, production cost height, its throughput far can not satisfy the demand to PEN that increases day by day in the world wide.
With naphthalene or methylnaphthalene is that raw material is through alkylated reaction one-step synthesis 2, the method of 6-DMN has advantages such as raw material sources are abundant, operational path is short, it is the route that has industrial prospect, but the alkylation of naphthalene or methylnaphthalene or transfering alkylation are the reaction systems of a complexity, also have side reactions such as many alkylations, isomerization, disproportionation, cracking to take place simultaneously, reaction product is mixture normally, therefore, the key that realizes this operational path is that exploitation has suitable reactive behavior and to 2,6-DMN has the catalytic material of highly selective.People such as G.P.Hagen (US5670704) are with AlCl
3Be catalyzer, multi-methyl benzenes such as durol are the transfering alkylation agent, and halohydrocarbon is a solvent, carry out the transfering alkylation reaction of beta-methylnaphthalene under 40 ℃.Experimental result shows, 2, and the yield of 6-DMN can reach 28.74%, but only dimethylnaphthalene just has ten kinds of isomer in alkylation or transfering alkylation product, particularly 2, and 6-DMN and 2, the molecular dynamics size of 7-DMN is close, is 0.72nm, all is again thermodynamically stable isomer, and the boiling point between these isomer is close, 2, and 6-DMN and 2, the boiling point of 7-DMN only differs 0.3 ℃, and product separates very difficult, and 2,6-DMN/2, the overall selectivity of 7-DMN is more than 60%.Although this reaction conditions relaxes, because AlCl
3Catalyzer can not be reused, and catalyzer and product separation difficulty also can produce acid-bearing wastewater simultaneously, and equipment is produced corrosion.Therefore research and develop a kind of under mild conditions the highly selective Synthetic 2, the catalyst system of 6-DMN is very important.
Ionic liquid is fully by organic cation and inorganic or organic anion constitutes, be the salt of liquid state under near temperature room temperature or the room temperature, by regulating positively charged ion and anionic ratio or introduce the acidic ion liquid that the acidic-group that contains reactive hydrogen can obtain having catalysis in ionic liquid.Existing method adopts Triethylammonium chloride chloroaluminate ionic liquid catalysis 2-methylnaphthalene and durol transfering alkylation prepared in reaction 2,6-DMN, after at room temperature reacting 8 hours, the transformation efficiency of 2-methylnaphthalene reaches at 23.4% o'clock, and 2, the selectivity of 6-DMN reaches 66.0%, 2.6-/2, the 7-DMN ratio is higher than 3.6, is ionic liquid-catalyzed selection Synthetic 2, and 6-DMN provides may.Chloroaluminate ionic liquid can obtain super acids by the HCl modification, makes its acid enhancing, helps improving ion liquid catalytic activity.
Summary of the invention
The objective of the invention is in order to solve existing preparation 2, complex process, the by product that 6-dimethylnaphthalene method exists be many, 2, the poor selectivity of 6-dimethylnaphthalene, from product, separate 2, the problem of 6-dimethylnaphthalene difficulty, provide a kind of ionic liquid-catalyzed highly-selective preparation 2, the method for 6-dimethylnaphthalene.
The ionic liquid-catalyzed preparation 2 of the present invention, the method of 6-dimethylnaphthalene is as follows: with methylnaphthalene, transfering alkylation agent and solvent, in mixed solution, add the ionic-liquid catalyst that accounts for mixed solution gross weight 10%～75% then, it in protection of inert gas, temperature reaction 0.5 hour～8 hours under 10 ℃～50 ℃ the condition, cool to room temperature then, again with the upper strata reaction solution decant in the stratified reaction solution after separate and to obtain 2, the 6-dimethylnaphthalene; The mol ratio of wherein said methylnaphthalene and transfering alkylation agent is 1:0.5～3, and the mol ratio of methylnaphthalene and solvent is 1:5～30; Described transfering alkylation agent is a 1; Described solvent is hexanaphthene, normal hexane or perhydronaphthalene.
Among the present invention under the refrigerative condition reaction solution natural layering, wherein ionic-liquid catalyst is in lower floor.
Methylnaphthalene described in the inventive method is 2-methylnaphthalene or mixed methylnaphthalene, wherein the mixture be made up of according to the mol ratio of 2～4:1 beta-methylnaphthalene and alpha-methyl-naphthalene of mixed methylnaphthalene; Described rare gas element is nitrogen or argon gas.
The preparation method of the ionic-liquid catalyst described in the present invention is as follows: is transparent liquid with metal halide and nitrogen-containing organic compound according to mixed in molar ratio to the mixed solution of 1～3:1, temperature with mixed solution rises to 60 ℃～150 ℃ then, isothermal reaction 1～5 hour, and then in mixed solution, fed hydrogenchloride 10 minutes～1 hour, promptly get ionic-liquid catalyst; Described nitrogen-containing organic compound is alkyl imidazole, alkyl pyridine, salt triethylenetetraminehexaacetic acid ammonium or hydrochloric acid TMA (TriMethylAmine); Wherein said alkyl imidazole is that alkyl chain length is C
1～C
8Halogenation 1,3-alkyl imidazole salt; Described alkyl pyridine is that alkyl chain length is C
1～C
8The halogenated alkyl pyridine; Described metal halide be aluminum trichloride (anhydrous), anhydrous zinc dichloride, FERRIC CHLORIDE ANHYDROUS, anhydrous chlorides of rase cuprous in one or more mixture.
Reaction conditions gentleness of the present invention, simple to operate, reaction times short (only being 0.5 hour～8 hours), product and ionic-liquid catalyst AUTOMATIC ZONING that reaction obtains, be easy to separate, adopt the inventive method to obtain 2, the selectivity of 6-dimethylnaphthalene is 66.4%～100%, far above Synthetic 2 under other catalyst action, the result of 6-dimethylnaphthalene. the inventive method is to 2, the selectivity ratios 2 of 6-dimethylnaphthalene, the selectivity height of 7-dimethylnaphthalene.The inventive method does not have multi-methylnaphthalene by product generations such as trimethyl-naphthalene, adopts the inventive method to produce 2, and the technology of 6-dimethylnaphthalene is simple, production cost is low, has good industrial prospect.
Embodiment
Technical solution of the present invention is not limited to following cited embodiment, also comprises the arbitrary combination between each embodiment.
Embodiment one: in the present embodiment 2, the method of 6-dimethylnaphthalene is as follows: with methylnaphthalene, transfering alkylation agent and solvent, in mixed solution, add the ionic-liquid catalyst that accounts for mixed solution gross weight 10%～75% then, it in protection of inert gas, temperature reaction 0.5 hour～8 hours under 10 ℃～50 ℃ the condition, cool to room temperature then, again with the upper strata reaction solution decant in the stratified reaction solution after separate and to obtain 2, the 6-dimethylnaphthalene; The mol ratio of wherein said methylnaphthalene and transfering alkylation agent is 1:0.5～3, and the mol ratio of methylnaphthalene and solvent is 1:5～30; Described transfering alkylation agent is a 1; Described solvent is hexanaphthene, normal hexane or perhydronaphthalene.
Reaction solution natural layering under the refrigerative condition in the present embodiment, wherein ionic-liquid catalyst is in lower floor.
Embodiment two: what present embodiment and embodiment one were different is that described methylnaphthalene is the 2-methylnaphthalene.Other is identical with embodiment one.
Embodiment three: what present embodiment and embodiment two were different is that described methylnaphthalene is a mixed methylnaphthalene, wherein the mixture be made up of according to the mol ratio of 2～4:1 beta-methylnaphthalene and alpha-methyl-naphthalene of mixed methylnaphthalene.Other is identical with embodiment two.
Embodiment four: what present embodiment and embodiment one were different is that described rare gas element is a nitrogen.Other is identical with embodiment one.
Embodiment five: what present embodiment and embodiment one were different is that described rare gas element is an argon gas.Other is identical with embodiment one.
Embodiment six: the preparation method of present embodiment intermediate ion liquid catalyst is as follows: is transparent liquid with metal halide and nitrogen-containing organic compound according to mixed in molar ratio to the mixed solution of 1～3:1, temperature with mixed solution rises to 60 ℃～150 ℃ then, isothermal reaction 1～5 hour, and then in mixed solution, fed hydrogenchloride 10 minutes～1 hour, promptly get ionic-liquid catalyst.
Embodiment seven: present embodiment and embodiment six are different is that to feed the hydrogenchloride time be 10 minutes.Other is identical with embodiment six.
The ionic-liquid catalyst that adopts the present embodiment method to obtain is used to prepare 2, the 6-dimethylnaphthalene, 2, the transformation efficiency of 6-dimethylnaphthalene is 7.5%, utilizes gas-chromatography that the upper strata reaction solution is analyzed, obtain in the alkylate 2, the selectivity 79.3%, 2 of 6-dimethylnaphthalene, the selectivity of 7-dimethylnaphthalene are 13.1%, as seen present method is to 2, and the selectivity of 6-dimethylnaphthalene is higher.
Embodiment eight: what present embodiment and embodiment six were different is that described nitrogen-containing organic compound is alkyl imidazole, alkyl pyridine, salt triethylenetetraminehexaacetic acid ammonium or hydrochloric acid TMA (TriMethylAmine).Other is identical with embodiment six.
Embodiment nine: what present embodiment and embodiment seven were different is that described alkyl imidazole is that alkyl chain length is C
1～C
8Halogenation 1,3-alkyl imidazole salt.Other is identical with embodiment seven.
Embodiment ten: present embodiment and embodiment six are different be described metal halide be aluminum trichloride (anhydrous), anhydrous zinc dichloride, FERRIC CHLORIDE ANHYDROUS, anhydrous chlorides of rase cuprous in one or more mixture.Other is identical with embodiment six.
When metal halide is mixture in the present embodiment, press between each composition arbitrarily than mixing.
Embodiment 11: what present embodiment and embodiment one were different is that temperature of reaction is 15 ℃.Other is identical with embodiment one.
The transformation efficiency of gained 2-methylnaphthalene is 7.4% in the present embodiment, utilizes gas-chromatography that the upper strata reaction solution is analyzed, and obtains in the alkylate 2, and the selectivity of 6-dimethylnaphthalene is 100%.
Embodiment 12: what present embodiment and embodiment one were different is that temperature of reaction is 10 ℃.Other is identical with embodiment one.
The transformation efficiency of gained 2-methylnaphthalene is 4.7% in the present embodiment, utilizes gas-chromatography that the upper strata reaction solution is analyzed, and obtains in the alkylate 2, and the selectivity of 6-dimethylnaphthalene is 100%.
Embodiment 13: what present embodiment and embodiment one were different is that temperature of reaction is 25 ℃.Other is identical with embodiment one.
The transformation efficiency of gained 2-methylnaphthalene is 22.7% in the present embodiment, utilize gas-chromatography that the upper strata reaction solution is analyzed, obtain in the alkylate 2, the selectivity of 6-dimethylnaphthalene is 69.0%, 2, the selectivity of 7-dimethylnaphthalene is 15.7%, this shows to adopt the inventive method to 2, the selectivity ratios 2 of 6-dimethylnaphthalene, the selectivity height of 7-dimethylnaphthalene.
Embodiment 14: what present embodiment and embodiment one were different is to be 1 hour in the reaction times.Other is identical with embodiment one.
The transformation efficiency of gained 2-methylnaphthalene is 6.1% in the present embodiment, utilizes gas-chromatography that the upper strata reaction solution is analyzed, and obtains in the alkylate 2, and the selectivity of 6-dimethylnaphthalene is 100%.
Embodiment 15: what present embodiment and embodiment one were different is to be 2 hours in the reaction times.Other is identical with embodiment one.
The transformation efficiency of gained 2-methylnaphthalene is 10.2% in the present embodiment, utilizes gas-chromatography that the upper strata reaction solution is analyzed, and obtains in the alkylate 2, and the selectivity of 6-dimethylnaphthalene is 100%.
Embodiment 16: what present embodiment and embodiment one were different is to be 4 hours in the reaction times.Other is identical with embodiment one.
The transformation efficiency of gained 2-methylnaphthalene is 28.6% in the present embodiment, utilize gas-chromatography that the upper strata reaction solution is analyzed, obtain in the alkylate 2, the selectivity of 6-dimethylnaphthalene is 66.4%, 2, the selectivity of 7-dimethylnaphthalene is 11.5%, this shows to adopt the inventive method to 2, the selectivity ratios 2 of 6-dimethylnaphthalene, the selectivity height of 7-dimethylnaphthalene.
Embodiment 17: present embodiment and embodiment one are different is that the consumption of ionic-liquid catalyst is 22%.Other is identical with embodiment one.
The transformation efficiency of gained 2-methylnaphthalene is 10.7% in the present embodiment, utilizes gas-chromatography that the upper strata reaction solution is analyzed, and obtains in the alkylate 2, the selectivity 100% of 6-dimethylnaphthalene.
Embodiment 18: present embodiment and embodiment one are different is that the consumption of ionic-liquid catalyst is 27%.Other is identical with embodiment one.
The transformation efficiency of gained 2-methylnaphthalene is 11.9% in the present embodiment, utilizes gas-chromatography that the upper strata reaction solution is analyzed, and obtains in the alkylate 2, the selectivity 100% of 6-dimethylnaphthalene.
Embodiment 19: present embodiment and embodiment one are different is that the consumption of ionic-liquid catalyst is 32%.Other is identical with embodiment one.
The transformation efficiency of gained 2-methylnaphthalene is 12.5% in the present embodiment, utilizes gas-chromatography that the upper strata reaction solution is analyzed, and obtains in the alkylate 2, the selectivity 100% of 6-dimethylnaphthalene.
Claims (9)
1, a kind of ionic liquid-catalyzed preparation 2, the method of 6-dimethylnaphthalene, it is characterized in that ionic liquid-catalyzed preparation 2, the method of 6-dimethylnaphthalene is as follows: with methylnaphthalene, transfering alkylation agent and solvent, in mixed solution, add the ionic-liquid catalyst that accounts for mixed solution gross weight 10%～75% then, it in protection of inert gas, temperature reaction 0.5 hour～8 hours under 10 ℃～50 ℃ the condition, cool to room temperature then, again with the upper strata reaction solution decant in the stratified reaction solution after separate and to obtain 2, the 6-dimethylnaphthalene; The mol ratio of wherein said methylnaphthalene and transfering alkylation agent is 1:0.5～3, and the mol ratio of methylnaphthalene and solvent is 1:5～30; Described transfering alkylation agent is a 1; Described solvent is hexanaphthene, normal hexane or perhydronaphthalene.
2, ionic liquid-catalyzed preparation 2 according to claim 1, the method for 6-dimethylnaphthalene is characterized in that described methylnaphthalene is 2-methylnaphthalene or mixed methylnaphthalene.
3, ionic liquid-catalyzed preparation 2 according to claim 2, the method for 6-dimethylnaphthalene is characterized in that described mixed methylnaphthalene is made up of according to the mol ratio of 2～4:1 beta-methylnaphthalene and alpha-methyl-naphthalene.
4, ionic liquid-catalyzed preparation 2 according to claim 1, the method for 6-dimethylnaphthalene is characterized in that described rare gas element is nitrogen or argon gas.
5, ionic liquid-catalyzed preparation 2 according to claim 1, the method of 6-dimethylnaphthalene, the preparation method who it is characterized in that ionic-liquid catalyst is as follows: is transparent liquid with metal halide and nitrogen-containing organic compound according to mixed in molar ratio to the mixed solution of 1～3:1, temperature with mixed solution rises to 60 ℃～150 ℃ then, isothermal reaction 1～5 hour, and then in mixed solution, fed hydrogenchloride 10 minutes～1 hour, promptly get ionic-liquid catalyst.
6, the preparation method of ionic-liquid catalyst according to claim 5 is characterized in that described nitrogen-containing organic compound is alkyl imidazole, alkyl pyridine, salt triethylenetetraminehexaacetic acid ammonium or hydrochloric acid TMA (TriMethylAmine).
7, the preparation method of ionic-liquid catalyst according to claim 6 is characterized in that described alkyl imidazole is that alkyl chain length is C
1～C
8Halogenation 1,3-alkyl imidazole salt.
8, the preparation method of ionic-liquid catalyst according to claim 6 is characterized in that described alkyl pyridine is that alkyl chain length is C
1～C
8The halogenated alkyl pyridine.
9, the preparation method of ionic-liquid catalyst according to claim 5, it is characterized in that described metal halide be aluminum trichloride (anhydrous), anhydrous zinc dichloride, FERRIC CHLORIDE ANHYDROUS, anhydrous chlorides of rase cuprous in one or more mixture.
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| CN2008101374783A CN101391937B (en) | 2008-11-06 | 2008-11-06 | Method for catalyzed synthesis of 2,6-dimethylnaphthalene by using ion liquid |
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| CN101391937B CN101391937B (en) | 2012-06-13 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108341734A (en) * | 2018-03-25 | 2018-07-31 | 王强 | A method of catalysis prepares 2,6- dimethylnaphthalenes |
| CN109742397A (en) * | 2019-01-04 | 2019-05-10 | 广州大学 | A kind of polymer cathode materials for Li-ion battery, preparation method and application |
| CN114591135A (en) * | 2022-03-24 | 2022-06-07 | 中国科学院大连化学物理研究所 | Method for preparing 2, 6-diisopropyl naphthalene by naphthalene shape-selective alkylation |
| CN114736089A (en) * | 2022-03-24 | 2022-07-12 | 中国科学院大连化学物理研究所 | Method for producing 2, 6-diisopropyl naphthalene |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5670704A (en) * | 1990-06-26 | 1997-09-23 | Amoco Corporation | Selective production of 2,6-dimethylnaphthalene |
| CN1261395C (en) * | 2004-12-15 | 2006-06-28 | 黑龙江省石油化学研究院 | Method for preparing 2,6-dimethylnaphthalene through dismutation of beta methylnaphthalene under catalysis of ion liquid |
| CN101020619B (en) * | 2006-02-13 | 2011-09-14 | 黑龙江大学 | Ionic liquid catalyzed transalkylation process for preparing 2,6-dimethyl naphthalene |
-
2008
- 2008-11-06 CN CN2008101374783A patent/CN101391937B/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108341734A (en) * | 2018-03-25 | 2018-07-31 | 王强 | A method of catalysis prepares 2,6- dimethylnaphthalenes |
| CN108341734B (en) * | 2018-03-25 | 2021-07-20 | 广东和汇新材料有限公司 | Method for preparing 2, 6-dimethylnaphthalene by catalysis |
| CN109742397A (en) * | 2019-01-04 | 2019-05-10 | 广州大学 | A kind of polymer cathode materials for Li-ion battery, preparation method and application |
| CN114591135A (en) * | 2022-03-24 | 2022-06-07 | 中国科学院大连化学物理研究所 | Method for preparing 2, 6-diisopropyl naphthalene by naphthalene shape-selective alkylation |
| CN114736089A (en) * | 2022-03-24 | 2022-07-12 | 中国科学院大连化学物理研究所 | Method for producing 2, 6-diisopropyl naphthalene |
| CN114736089B (en) * | 2022-03-24 | 2023-08-08 | 中国科学院大连化学物理研究所 | Method for producing 2, 6-diisopropyl naphthalene |
| CN114591135B (en) * | 2022-03-24 | 2023-09-15 | 中国科学院大连化学物理研究所 | Method for preparing 2, 6-diisopropyl naphthalene by naphthalene shape-selective alkylation |
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