CN102001907A - Method for synthetizing 2,6-dimethylnaphthalene with methanol, C10 arene and 2-methylnaphthalene through alkylation - Google Patents
Method for synthetizing 2,6-dimethylnaphthalene with methanol, C10 arene and 2-methylnaphthalene through alkylation Download PDFInfo
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- CN102001907A CN102001907A CN 201010503925 CN201010503925A CN102001907A CN 102001907 A CN102001907 A CN 102001907A CN 201010503925 CN201010503925 CN 201010503925 CN 201010503925 A CN201010503925 A CN 201010503925A CN 102001907 A CN102001907 A CN 102001907A
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- methylnaphthalene
- dimethylnaphthalene
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- aromatic hydrocarbons
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 78
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 title claims abstract description 52
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000005804 alkylation reaction Methods 0.000 title claims abstract description 16
- 230000029936 alkylation Effects 0.000 title claims abstract description 14
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims abstract 11
- 230000003407 synthetizing effect Effects 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 239000002808 molecular sieve Substances 0.000 claims abstract description 18
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract 14
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000012159 carrier gas Substances 0.000 claims description 13
- 229910021536 Zeolite Inorganic materials 0.000 claims description 10
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 10
- 239000010457 zeolite Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims 2
- -1 alkyl aromatic hydrocarbons Chemical class 0.000 claims 1
- 238000005516 engineering process Methods 0.000 abstract description 5
- 239000000376 reactant Substances 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000006555 catalytic reaction Methods 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical group CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010555 transalkylation reaction Methods 0.000 description 2
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical class C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000006208 butylation Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及一种甲醇、碳十芳烃与2-甲基萘烷基化合成2，6-二甲基萘的方法，它是以2-甲基萘、甲醇和碳十芳烃(以四甲苯为主的一种碳原子数为10的芳烃混合物，为芳烃装置副产物)的混合物为原料，通过分子筛催化烷基化反应来制备2，6-二甲基萘的方法。它是以甲醇为原料a，以碳十芳烃为原料b，以2-甲基萘为原料c，按照a∶c＝1～3∶1(mol/mol)和b∶c＝1～6∶1(mol/mol)配成混合物原料，在380～500℃的反应温度、0～6.0MPa的反应压力、反应空速为0.1～2h-1下，通过分子筛催化剂实现烷基化来合成2，6-二甲基萘的方法技术。本发明在利用副产低值的碳十芳烃资源的同时，反应物中引入价廉、来源丰富的甲醇，能有效提高反应活性、选择性和反应稳定性。The present invention relates to a kind of method that methanol, carbon ten aromatic hydrocarbons and 2-methylnaphthalene are alkylated to synthesize 2,6-dimethylnaphthalene, and it is based on 2-methylnaphthalene, methyl alcohol and carbon ten aromatic hydrocarbons (taking tetramethylbenzene as The main one is a mixture of aromatics with 10 carbon atoms, which is a by-product of aromatics plant) as a raw material, and a method for preparing 2,6-dimethylnaphthalene through molecular sieve catalyzed alkylation reaction. It takes methanol as raw material a, carbon ten aromatics as raw material b, and 2-methylnaphthalene as raw material c, according to a:c=1～3:1 (mol/mol) and b:c=1～6: 1 (mol/mol) is made into a mixture raw material, and at a reaction temperature of 380-500°C, a reaction pressure of 0-6.0MPa, and a reaction space velocity of 0.1-2h -1 , 2 is synthesized by alkylation through a molecular sieve catalyst, Process technology for 6-dimethylnaphthalene. The invention utilizes low-value C10 aromatic hydrocarbon resources as by-products, and introduces cheap and abundant methanol into the reactants, which can effectively improve the reaction activity, selectivity and reaction stability.
Description
Technical field
The present invention relates to a kind of methyl alcohol, C10 aromartic and 2-methylnaphthalene alkylation Synthetic 2, the method for 6-dimethylnaphthalene.
Background technology
2,6-dialkyl group naphthalene (2, be to produce the important precursor of novel high-performance polyester material 6-DANs), wherein 2,6-DMN is considered to have most a chemical of application prospect, it can be oxidized into 2, the 6-naphthalic acid, and the latter is a raw material of producing high performance material PEN (PEN).The selling at exorbitant prices of PEN has at present restricted it and has come into the market on a large scale, and the principal element that influences the PEN price is 2, and the 6-dimethylnaphthalene has complex manufacturing now, and production cost is higher.Traditional BP-Amoco complex technical process, step be many, yield poorly, and by product environmental pollution serious (Asian ChemicalNews, Nov.16,1998; Chemical Market Reporter, Aug.2,1999).US Patent 6121501 (M.Motoyuki, K.Yamamoto, shortcomings such as A.V.Sapre et al.) selective conversion by the dimethylnaphthalene isomer mixture prepares 2 with separating, and the 6-dimethylnaphthalene is also various owing to its processing step, overall yield is low are not applied.Ethylization (the G.Takeuchi of report by naphthalene also arranged, Y.Shimoura, T.Hara, Catal.Lett.41 (1996) 195.), propylated (J.Wang, J.N.Park, Y.K.Park et al.Catal.Today 97 (2004) 283.) and butylation (R.P.Marathe, S.Mayadevi, S.A.Pardhy et al.J.Mol.Catal.A 181 (2002) 201.) product comes Synthetic 2, the 6-naphthalic acid.But Comparatively speaking, direct Synthetic 2, the 6-dimethylnaphthalene has more potential value, because there is not the variation of carbonatoms in the oxidising process of subsequent production PEN, and the easier oxidation of methyl.Naphthalene or methylnaphthalene alkylated reaction on zeolite molecular sieve is considered to a kind of efficient, simple 2,6-dimethylnaphthalene synthetic route, especially the direct Synthetic 2 of methylnaphthalene alkylation, the 6-dimethylnaphthalene, utilized the shape selectivity catalysis of molecular sieve, its technology is simple, and is considered to have very high potential using value.Kobe Steel and (the M Motoyuki of ExxonMobil company, K Yamamoto, S Vishwanath, et al.US, Patent.6011190 (2000) .) reported a kind of alkylation by methylnaphthalene on the MCM-22 zeolite catalyst and methyl alcohol, naphthalene and methylnaphthalene transalkylation or isomerization in another reactor subsequently, you come Synthetic 2 with circulation at separating for several times, the technology of 6-dimethylnaphthalene, but because its processing step is many, material consumption is big, and production cost is also very high.WO02060581 reports that (L.D.Lillwita is C.Song) at process FeF
3And NH
4HF
2Carry out the direct Synthetic 2 of alkylated reaction of methylnaphthalene and methyl alcohol on the HZSM-5 molecular sieve of modifying, the 6-dimethylnaphthalene, can obtain 60% 2,6-dimethylnaphthalene selectivity and 1.8～2.2 2,6-/2, the ratio of 7-dimethylnaphthalene isomer, but 2, the synthesis yield of 6-dimethylnaphthalene is still lower.In addition, report (C.Zhang is arranged recently, X.W.Guo, C.S.Song et al.Catalysis Today 149 (2010) 196-201.) claim on HZSM-5 molecular sieve, to have obtained respectively through tetraethoxy modification and steam treatment 5.3% and 7.6% 2,6-dimethylnaphthalene yield, and think and improving 2,6-/2, on the ratio of 7-dimethylnaphthalene isomer, the acidity of zeolite molecular sieve is regulated more more favourable than the control of duct size, but the side reaction of following is more serious, and catalyst deactivation is fast.
At present, though methylnaphthalene and methyl alcohol is the alkylated reaction Synthetic 2 on molecular sieve, the selectivity of product of 6-dimethylnaphthalene can be improved by the modification of acidic zeolite and structure, but 2, the yield of 6-dimethylnaphthalene product is on the low side, and catalyst stability is not good, has influenced the industrial application of this technology.
Summary of the invention
The object of the present invention is to provide a kind of processing step easy, the methyl alcohol that production cost is low, yield is high, C10 aromartic and 2-methylnaphthalene alkylation Synthetic 2, the method for 6-dimethylnaphthalene.
Methyl alcohol, C10 aromartic and 2-methylnaphthalene alkylation Synthetic 2 that the present invention proposes, the method for 6-dimethylnaphthalene, concrete steps are as follows:
With methyl alcohol, C10 aromartic and 2-methylnaphthalene is raw material, is made into mixture material, feeds carrier gas, and under 380～500 ℃ temperature of reaction, keeping reaction velocity under the reaction pressure of 0～6.0MPa is 0.1～2h
-1, in fixed bed catalytic reactor, realize alkylated reaction, Synthetic 2,6-dimethylnaphthalene by Zeolite molecular sieve catalysis; Wherein: the mol ratio of methyl alcohol and C10 aromartic is 1: 1～3: 1, and the mol ratio of C10 aromartic and 2-methylnaphthalene is 1: 1～6: 1.
Among the present invention, preferable temperature of reaction is 400～480 ℃, and reaction pressure is 0.5～4.0MPa, and reaction velocity is 0.5～1h
-1
Among the present invention, described carrier gas is a hydrogen.
Among the present invention, the mol ratio of C10 aromartic and 2-methylnaphthalene is 2: 1～6: 1.
Among the present invention, this method be with methyl alcohol and C10 aromartic as methylating reagent, effectively realize alkylated reaction with methylnaphthalene by acidic zeolite catalysis; Described C10 aromartic is that carbonatoms is 10 alkylaromatic hydrocarbon mixture, and its major ingredient is a durene.
Among the present invention, described zeolite catalyst is an one to multiple kind in ZSM-5, MCM-22, USY, Beta or the MOR molecular sieve, and it is the highest by 2, and 6-dimethylnaphthalene product yield can reach more than 15%.
The transformation efficiency of 2-methylnaphthalene, 2 among the present invention, the selectivity of 6-dimethylnaphthalene and 2, the method for calculation of the yield of 6-dimethylnaphthalene are as follows:
2,6-dimethylnaphthalene yield (%)=2-methylnaphthalene transformation efficiency (%) * 2,6-dimethylnaphthalene selectivity (%)
The present invention introduces methyl alcohol inexpensive, that the source is abundant in the reactant when utilizing the C10 aromartic resource of by-product low value, can effectively improve reactive behavior, selectivity, product yield and reaction stability.
Embodiment
Further specify the present invention below by embodiment.
Embodiment 1: an amount of granulated glass sphere of packing in the reaction tubes bed bottom of the small fixed catalyticreactor of internal diameter 1.5cm earlier, shop skim silica wool on granulated glass sphere, be 24 the Beta molecular sieve catalyst reaction tubes of packing into again with the cylindric silica alumina ratio of 5.0g, the upper strata an amount of granulated glass sphere that recharges, feed carrier gas hydrogen then, guarantee that air-flow evenly flows through beds; Reaction pressure is 2.0MPa, through temperature programming in 100 minutes to design temperature, consist of a (methyl alcohol): c (2-methylnaphthalene)=1: 1 (mol/mol), the reaction raw materials of b (C10 aromartic): c (2-methylnaphthalene)=4: 1 (mol/mol), mass space velocity WHSV=1.2h with the volume pump feeding
-1, investigate catalyzed reaction effect under the differing temps by low temperature to high temperature, sample calculates the transformation efficiency and 2 of the 2-methylnaphthalene of reaction, the selectivity of 6-dimethylnaphthalene, yield through gas chromatographic analysis.
Embodiment 2: it is that 5 USY molecular sieve is catalyzer that the present embodiment difference from Example 1 is to use silica alumina ratio, feeds carrier gas hydrogen, and carrier gas/reactant ratio is 4: 1 (mol/mol); Other concrete reaction conditions sees Table 1.
Embodiment 3: it is that 48 ZSM-5 molecular sieve is catalyzer that the present embodiment difference from Example 1 is to use silica alumina ratio, feeds carrier gas nitrogen, and carrier gas/reactant ratio is 1.8: 1 (mol/mol); Other concrete reaction conditions sees Table 1.
Embodiment 4: it is that 22 MCM-22 molecular sieve is catalyzer that the present embodiment difference from Example 1 is to use silica alumina ratio, does not feed carrier gas; Other concrete reaction conditions sees Table 1.
Embodiment 5: it is that 18 MOR molecular sieve is catalyzer that the present embodiment difference from Example 1 is to use silica alumina ratio, does not feed carrier gas; Other concrete reaction conditions sees Table 1.
Embodiment 6: the present embodiment difference from Example 1 be to use silica alumina ratio be 26 Beta molecular sieve as catalyzer, feed carrier gas hydrogen, carrier gas/reactant ratio is 8: 1 (mol/mol); Other reaction conditionss are identical with embodiment 5 with embodiment.
Table 1 is reaction conditions and the catalyzed reaction result of above 6 embodiment.
Table 1:
From last table catalyzed reaction data as seen: fixed bed catalytic reactor, with methyl alcohol a, C10 aromartic b and 2-methylnaphthalene c by a: c=1～3: 1 (mol/mol) with b: c=1～(kg/kg) was made into a kind of mixture material in 6: 1, at 380～500 ℃, 0～6.0MPa and 0.1～2h
-1Down, by ZSM-5, USY, MCM-22, Beta and MOR zeolite catalysis transalkylation reaction Synthetic 2, the 6-dimethylnaphthalene, selectivity of product and yield are higher, so exist higher industrial applications to be worth.
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010503925XA CN102001907B (en) | 2010-10-08 | 2010-10-08 | Method for synthetizing 2,6-dimethylnaphthalene with methanol, C10 arene and 2-methylnaphthalene through alkylation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010503925XA CN102001907B (en) | 2010-10-08 | 2010-10-08 | Method for synthetizing 2,6-dimethylnaphthalene with methanol, C10 arene and 2-methylnaphthalene through alkylation |
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| Publication Number | Publication Date |
|---|---|
| CN102001907A true CN102001907A (en) | 2011-04-06 |
| CN102001907B CN102001907B (en) | 2012-05-23 |
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| CN201010503925XA Expired - Fee Related CN102001907B (en) | 2010-10-08 | 2010-10-08 | Method for synthetizing 2,6-dimethylnaphthalene with methanol, C10 arene and 2-methylnaphthalene through alkylation |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102491868A (en) * | 2011-12-02 | 2012-06-13 | 黑龙江大学 | Method for catalyzing and preparing 2, 6-dimethylnaphalene by utilizing SAPO-31 molecular sieve |
| CN102746102A (en) * | 2012-07-26 | 2012-10-24 | 黑龙江大学 | Preparation method of 2,6-DiMethylnaphthalene (DMN) by using SAPO-11 molecular sieve |
| CN115678603A (en) * | 2021-07-30 | 2023-02-03 | 中国石油化工股份有限公司 | Method for producing triene, BTX and dimethylnaphthalene by using double fluidized bed reactor |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1362392A (en) * | 2001-12-31 | 2002-08-07 | 黑龙江省石油化学研究院 | Prepn of 2,6-dimethylnaphthalene |
-
2010
- 2010-10-08 CN CN201010503925XA patent/CN102001907B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1362392A (en) * | 2001-12-31 | 2002-08-07 | 黑龙江省石油化学研究院 | Prepn of 2,6-dimethylnaphthalene |
Non-Patent Citations (1)
| Title |
|---|
| 《化工新型材料》 20060331 吴伟等 HY型分子筛催化合成2,6-二甲基萘 54-57 1-6 第34卷, 第3期 2 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102491868A (en) * | 2011-12-02 | 2012-06-13 | 黑龙江大学 | Method for catalyzing and preparing 2, 6-dimethylnaphalene by utilizing SAPO-31 molecular sieve |
| CN102491868B (en) * | 2011-12-02 | 2014-06-11 | 黑龙江大学 | Method for catalyzing and preparing 2, 6-dimethylnaphalene by utilizing SAPO-31 molecular sieve |
| CN102746102A (en) * | 2012-07-26 | 2012-10-24 | 黑龙江大学 | Preparation method of 2,6-DiMethylnaphthalene (DMN) by using SAPO-11 molecular sieve |
| CN102746102B (en) * | 2012-07-26 | 2015-01-21 | 黑龙江大学 | Preparation method of 2,6-DiMethylnaphthalene (DMN) by using SAPO-11 molecular sieve |
| CN115678603A (en) * | 2021-07-30 | 2023-02-03 | 中国石油化工股份有限公司 | Method for producing triene, BTX and dimethylnaphthalene by using double fluidized bed reactor |
| CN115678603B (en) * | 2021-07-30 | 2024-02-09 | 中国石油化工股份有限公司 | Method for producing triene, BTX and dimethylnaphthalene by using double fluidized bed reactor |
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