CN101391937B - 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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- CN101391937B CN101391937B CN2008101374783A CN200810137478A CN101391937B CN 101391937 B CN101391937 B CN 101391937B CN 2008101374783 A CN2008101374783 A CN 2008101374783A CN 200810137478 A CN200810137478 A CN 200810137478A CN 101391937 B CN101391937 B CN 101391937B
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- dimethylnaphthalene
- methylnaphthalene
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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) through 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 superior to PET.Being widely used in industries such as process industry, building slab, fiber, insulating material, film, disk, carafe, 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 YLENE 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; Be the route that has industrial prospect, but the alkylation of naphthalene or methylnaphthalene or transfering alkylation are the reaction systems of a complicacy, also have side reactions such as many alkylations, isomerizing, 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, under 40 ℃, carry out the transfering alkylation reaction of beta-methylnaphthalene.Experimental result shows, 2, the yield of 6-DMN can reach 28.74%, but in alkylation or transfering alkylation product only dimethylnaphthalene ten kinds of isomer are just arranged, particularly 2; 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 differ 0.3 ℃; Product separates very difficulty, 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, under near temperature room temperature or the room temperature, be the salt of liquid state, through regulating positively charged ion and anionic ratio or in ionic liquid, introducing the acidic ion liquid that the acidic-group that contains reactive hydrogen can obtain having catalysis.Existing method adopts Triethylammonium chloride chloroaluminate ionic liquid catalysis 2-methylnaphthalene and durol transfering alkylation prepared in reaction 2,6-DMN, at room temperature react 8 hours after; 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 maybe.Chloroaluminate ionic liquid can obtain super acids through 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 separates 2 from product, the problem of 6-dimethylnaphthalene difficulty; A kind of ionic liquid-catalyzed highly-selective preparation 2 is provided, the method for 6-dimethylnaphthalene.
The ionic liquid-catalyzed preparation 2 of the present invention; The method of 6-dimethylnaphthalene is following: with methylnaphthalene, transfering alkylation agent and solvent; In mixed solution, adding the ionic-liquid catalyst account for mixed solution gross weight 10%～75% then, is reaction 0.5 hour～8 hours under 10 ℃～50 ℃ the condition, cool to room temperature then in protection of inert gas, temperature; 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 following: 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 of the present invention is gentle, simple to operate, the reaction times short (being merely 0.5 hour～8 hours), and product and ionic-liquid catalyst AUTOMATIC ZONING that reaction obtains are 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 of 7-dimethylnaphthalene is high.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 the good industrial prospect.
Embodiment
Technical scheme of the present invention is not limited to following cited embodiment, also comprises the arbitrary combination between each embodiment.
Embodiment one: in this embodiment 2; The method of 6-dimethylnaphthalene is following: with methylnaphthalene, transfering alkylation agent and solvent; In mixed solution, adding the ionic-liquid catalyst account for mixed solution gross weight 10%～75% then, is reaction 0.5 hour～8 hours under 10 ℃～50 ℃ the condition, cool to room temperature then in protection of inert gas, temperature; 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 this embodiment, wherein ionic-liquid catalyst is in lower floor.
Embodiment two: what this embodiment and embodiment one were different is that described methylnaphthalene is the 2-methylnaphthalene.Other is identical with embodiment one.
Embodiment three: what this 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 this embodiment and embodiment one were different is that described rare gas element is a nitrogen.Other is identical with embodiment one.
Embodiment five: what this 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 this embodiment intermediate ion liquid catalyst is following: 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: this embodiment and embodiment six are different is that to feed the hydrogenchloride time be 10 minutes.Other and embodiment six phase are together.
The ionic-liquid catalyst that adopts this embodiment method to obtain is used to prepare 2,6-dimethylnaphthalene, 2; The transformation efficiency of 6-dimethylnaphthalene is 7.5%, utilizes gc that the upper strata reaction solution is analyzed, and obtains in the alkylate 2; The selectivity 79.3%, 2 of 6-dimethylnaphthalene, the selectivity of 7-dimethylnaphthalene are 13.1%; It is thus clear that present method is to 2, the selectivity of 6-dimethylnaphthalene is higher.
Embodiment eight: what this 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 and embodiment six phase are together.
Embodiment nine: what this 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: this 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 and embodiment six phase are together.
When metal halide is mixture in this embodiment, press between each composition arbitrarily than mixing.
Embodiment 11: what this 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 this embodiment, utilizes gc 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 this 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 this embodiment, utilizes gc 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 this 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 this embodiment, utilizes gc that the upper strata reaction solution is analyzed, and obtains 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 of 7-dimethylnaphthalene is high.
Embodiment 14: what this 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 this embodiment, utilizes gc 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 this 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 this embodiment, utilizes gc 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 this 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 this embodiment, utilizes gc that the upper strata reaction solution is analyzed, and obtains 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 of 7-dimethylnaphthalene is high.
Embodiment 17: this 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 this embodiment, utilizes gc that the upper strata reaction solution is analyzed, and obtains in the alkylate 2, the selectivity 100% of 6-dimethylnaphthalene.
Embodiment 18: this 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 this embodiment, utilizes gc that the upper strata reaction solution is analyzed, and obtains in the alkylate 2, the selectivity 100% of 6-dimethylnaphthalene.
Embodiment 19: this 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 this embodiment, utilizes gc that the upper strata reaction solution is analyzed, and obtains in the alkylate 2, the selectivity 100% of 6-dimethylnaphthalene.
Claims (8)
1. ionic liquid-catalyzed preparation 2; The method of 6-dimethylnaphthalene; It is characterized in that ionic liquid-catalyzed preparation 2, the method for 6-dimethylnaphthalene is following: 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 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;
The preparation method of ionic-liquid catalyst is following: with metal halide and nitrogen-containing organic compound according to 1～3: 1 mixed in molar ratio to mixed solution is a transparent liquid; 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.
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, it is characterized in that described mixed methylnaphthalene by beta-methylnaphthalene and alpha-methyl-naphthalene according to 2～4: 1 mol ratio is formed.
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 for 6-dimethylnaphthalene is characterized in that described nitrogen-containing organic compound is alkyl imidazole, alkyl pyridine, salt triethylenetetraminehexaacetic acid ammonium or hydrochloric acid TMA(TriMethylAmine).
6. ionic liquid-catalyzed preparation 2 according to claim 5, the method for 6-dimethylnaphthalene is characterized in that described alkyl imidazole is that alkyl chain length is C
1～C
8Halogenation 1,3-alkyl imidazole salt.
7. ionic liquid-catalyzed preparation 2 according to claim 5, the method for 6-dimethylnaphthalene is characterized in that described alkyl pyridine is that alkyl chain length is C
1～C
8The halogenated alkyl pyridine.
8. ionic liquid-catalyzed preparation 2 according to claim 1; The method of 6-dimethylnaphthalene, 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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| 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 |
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2246788A (en) * | 1990-06-26 | 1992-02-12 | Amoco Corp | Selective production of 2,6-dimethylnaphthalene |
| CN1660726A (en) * | 2004-12-15 | 2005-08-31 | 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 |
| CN101020619A (en) * | 2006-02-13 | 2007-08-22 | 黑龙江大学 | Ionic liquid catalyzed transalkylation process for preparing 2,6-dimethyl naphthalene |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2246788A (en) * | 1990-06-26 | 1992-02-12 | Amoco Corp | Selective production of 2,6-dimethylnaphthalene |
| CN1660726A (en) * | 2004-12-15 | 2005-08-31 | 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 |
| CN101020619A (en) * | 2006-02-13 | 2007-08-22 | 黑龙江大学 | Ionic liquid catalyzed transalkylation process for preparing 2,6-dimethyl naphthalene |
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