CN105396612A - Preparation method of modified Beta molecular sieve catalyst and application thereof - Google Patents
Preparation method of modified Beta molecular sieve catalyst and application thereof Download PDFInfo
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- CN105396612A CN105396612A CN201510752022.8A CN201510752022A CN105396612A CN 105396612 A CN105396612 A CN 105396612A CN 201510752022 A CN201510752022 A CN 201510752022A CN 105396612 A CN105396612 A CN 105396612A
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- molecular sieve
- beta molecular
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- 239000003054 catalyst Substances 0.000 title claims abstract description 57
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 239000002808 molecular sieve Substances 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims abstract description 60
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 15
- 238000001291 vacuum drying Methods 0.000 claims abstract description 10
- 238000012986 modification Methods 0.000 claims description 31
- 230000004048 modification Effects 0.000 claims description 31
- DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 claims description 17
- 229910000348 titanium sulfate Inorganic materials 0.000 claims description 17
- 230000004913 activation Effects 0.000 claims description 7
- 238000001354 calcination Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002309 gasification Methods 0.000 claims description 3
- 238000007598 dipping method Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000012159 carrier gas Substances 0.000 claims 1
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 abstract description 20
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 abstract description 20
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract description 20
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 238000007323 disproportionation reaction Methods 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 3
- SOBXOQKKUVQETK-UHFFFAOYSA-H titanium(3+);trisulfate Chemical compound [Ti+3].[Ti+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O SOBXOQKKUVQETK-UHFFFAOYSA-H 0.000 abstract 3
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000002791 soaking Methods 0.000 abstract 1
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 description 16
- 229910010413 TiO 2 Inorganic materials 0.000 description 9
- 239000002994 raw material Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 238000004939 coking Methods 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920000106 Liquid crystal polymer Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 1
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- -1 ammonium radical ion Chemical class 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005120 petroleum cracking Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- HFDCVHDLKUZMDI-UHFFFAOYSA-N sulfuric acid titanium Chemical compound [Ti].OS(O)(=O)=O HFDCVHDLKUZMDI-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a preparation method of a titanous sulfate modified Beta molecular sieve catalyst and application thereof. The method comprises the following steps: (1) putting a roasted and activated Beta molecular sieve into a hydrothermal kettle; (2) preparing a titanous sulfate solution with the mole concentration of 0.1-0.3mol/l; (3) soaking the Beta molecular sieve completely in the titanous sulfate solution at constant temperature and constant pressure, carrying out vacuum drying, and roasting so as to prepare the modified Beta molecular sieve catalyst. The catalyst disclosed by the invention is applied to isomerization and disproportionation of 1-methylnaphthalene; the conversion rate of 1-methylnaphthalene is about 60%, and the selectivity of active products (2-methylnaphthalene, naphthalene and dimethylnaphthalene) is not less than 98%; the modified Beta molecular sieve catalyst can be synthesized by a one-step process; the technology is simple, and the preparation method is suitable for large-scale industrial production; the prepared catalyst can be used for multiple times repeatedly, is high in catalytic activity and selectivity, is long in service life, and is low in cost.
Description
Technical field
The present invention relates to a kind of Beta molecular sieve catalyst, particularly relate to a kind of preparation method of modification Beta molecular sieve catalyst, and by prepared catalyst application in the isomerization/disproportionated reaction of 1-methyl naphthalene.
Background technology
2,6-dimethylnaphthalene (2,6-DMN), it is a kind of very important polycyclic aromatic hydrocarbon compounds, is the intermediate preparing high-performance polyester, and it obtains 2 through oxidation, 6-naphthalene dihydroxy acid (2,6-NDA), continue oxidation, multiple high performance plastics and thermotropic liquid crystal polymer (LCP) can be obtained further.And 1-methyl naphthalene transforms (isomerization/disproportionation) for effective product (2-methyl naphthalene, naphthalene, dimethylnaphthalene) and is the important raw material of synthesis 2,6-dimethylnaphthalene.
The conventional method of preparation 2,6-dimethylnaphthalene is, extracting directly from coal tar and petroleum cracking product, but this method productive rate is lower, adopts chemical synthesis industrial more.As with naphthalene and 2-methyl naphthalene for raw material, carry out alkylated reaction, optionally can prepare 2,6-DMN; To mix dimethylnaphthalene for raw material, 2,6-DMN is prepared in selective isomerization; In addition also having with toluene is raw material, take dimethylbenzene as raw material, or prepares the methods such as 2,6-dimethylnaphthalene with 4-toluene bromide and 3-methyl-3-butene-1-alcohol for raw material.Visible 1-methyl naphthalene transforms the raw material that the effective product (2-methyl naphthalene, naphthalene, dimethylnaphthalene) prepared all can become preparation 2,6-dimethylnaphthalene.
The catalyst of the isomerization of 1-methyl naphthalene and disproportionation is mainly molecular sieve, ammonium radical ion is adopted to exchange modified molecular sieve in prior art, there is a certain amount of strong acid center in outer surface, easily makes cracking and coking reaction occur in course of reaction, reduces the yield of the effective product of reaction.
Summary of the invention
Main purpose of the present invention is, overcome existing catalyst cracking accessory substance in 1-methyl naphthalene conversion process many, the defect that target product proportion is little, a kind of preparation method of modification Beta molecular sieve catalyst is provided, the catalyst of described method one-step synthesis high selectivity, high conversion, high yield, be applied in 1-methyl naphthalene conversion process, produce cracking and coking accessory substance hardly, the conversion ratio about 60% of 1-methyl naphthalene, the selective of effective product (2-methyl naphthalene, naphthalene, dimethylnaphthalene) is promoted to more than 98%.
Another object of the present invention is to provide the application of a kind of described catalyst in the isomerization/disproportionated reaction of 1-methyl naphthalene.
For realizing object of the present invention, by the following technical solutions: a kind of preparation method of modification Beta molecular sieve catalyst proposed according to the present invention, comprise the steps: that the Beta molecular sieve of calcination activation is placed in water heating kettle by (1); (2) configuring molar concentration is the titanium sulfate solution of 0.1-0.3mol/l; (3) under constant temperature and pressure, Beta molecular sieve be impregnated in titanium sulfate solution, vacuum drying, roasting, obtained described modification Beta molecular sieve catalyst.
The present invention adopts SO
4 2-/ TiO
2solid acid, carries out modification to molecular sieve surface, produces selective high acid site, improves target product selectivity.
The aforesaid method preparing modification Beta molecular sieve catalyst, mass ratio=5 ~ 15% of Ti:Beta molecular sieve described in step (3).
The aforesaid method preparing modification Beta molecular sieve catalyst, described dipping refers to stirring 4 ~ 6h at 25 DEG C, and vacuum drying is 110 DEG C of vacuum drying 10 ~ 12h preferably.
The aforesaid method preparing modification Beta molecular sieve catalyst, described roasting is preferably at 550 DEG C of roasting 5 ~ 8h.
The invention still further relates to the application of described catalyst in the isomerization/disproportionated reaction of 1-methyl naphthalene, namely with described modification Beta molecular sieve for catalyst, carry out the isomerization/disproportionated reaction of 1-methyl naphthalene in the gas phase.
With described modification Beta molecular sieve for catalyst, by the 1-methyl naphthalene after gasification by beds, the air speed of 1-methyl naphthalene is 0.5 ~ 1.5h
-1, reaction temperature is 300 ~ 450 DEG C, and reaction pressure is normal pressure.
By technique scheme, the preparation method of modification Beta molecular sieve catalyst of the present invention at least has following advantages:
Adopt wet impregnation method, the condition of regulation and control titanium sulfate modification Beta molecular sieve catalyst, utilizes titanium sulfate to produce SO
4 2-/ TiO
2type acid site, uniform load is on Beta surface; Regulation and control SO
4 2-/ TiO
2amount, ensure the high-specific surface area of catalyst, improve the conversion ratio of 1-methyl naphthalene; Regulation and control sintering temperature, makes titanium sulfate better produce selective high SO
4 2-/ TiO
2acid site, improves the selective of target product, thus improves the productive rate of target product; Obtained catalyst is renewable to be recycled.This kind of new catalyst preparation process is simple, can be used for industrialization large-scale production.
Above-mentioned explanation is only the general introduction of technical solution of the present invention, in order to better understand technological means of the present invention, and can be implemented according to the content of description, be described in detail as follows below with preferred embodiment of the present invention.
Accompanying drawing explanation
1-methyl naphthalene isomerization/disproportionated reaction schematic flow sheet in Fig. 1 continuous tubular reactor.
Detailed description of the invention
For further setting forth the present invention for the technological means reaching predetermined goal of the invention and take and effect, to its detailed description of the invention of method preparing titanium sulfate modification Beta molecular sieve catalyst proposed according to the present invention, feature and effect thereof, be described in detail as follows.
The preparation method of modification Beta molecular sieve catalyst of the present invention is: the Beta molecular sieve of calcination activation is placed in water heating kettle by (1); (2) configuring molar concentration is the titanium sulfate solution of 0.1-0.3mol/l; (3), under constant temperature and pressure, Beta molecular sieve thorough impregnation is in titanium sulfate solution 5h, and vacuum drying 12h, 550 DEG C of roasting 7h, finally obtain described titanium sulfate modification Beta molecular sieve catalyst.
Obtained modification Beta molecular sieve catalyst is filled in the single line continuous tubular reactor shown in Fig. 1, carry out the catalytic conversion reaction of 1-methyl naphthalene, in figure, 1 is gas bomb, 2 is filter, 3 is pressure maintaining valve, 4 is drier, 5 is mass flowmenter, 6 is check (non-return) valve, 7 is surge flask, 8 is preheater, 9 is preheater heating furnace, 10 is reactor heating furnace, 11 is reactor, 12 is condenser, 13 is gas-liquid separator, 14 is counterbalance valve, 15 is manual sampler, 16 is real-time flow meter, 17 is charge pump, V is stop valve, S is three-way change-over valve, TCI is temperature control, TI is thermometric, PI is pressure measurement.
In continuous tubular reactor, add catalyst, consumption 10 ~ 12g, adopt nitrogen to purge except surface physics adsorbent, purging temperature is 100 ~ 450 DEG C, start measuring pump, by catalyst filling post after the gasification of 1-methyl naphthalene, the air speed regulating 1-methyl naphthalene is 0.5 ~ 1.5h
-1, reaction temperature is 300 ~ 450 DEG C, and reaction pressure is normal pressure.
Isomerization/disproportionated reaction condition is as shown in table 1, through steps such as purging, constant temperature, reaction, sampling, test samples, obtains result shown in table 2.
Table 1 technological parameter
Table 2 continuous tubular reactor 1-methyl naphthalene isomerization experiments result
Embodiment 1
Titanium sulfate modification Beta sieve method is adopted to prepare ST-B-1 catalyst: concrete grammar is: the Beta molecular sieve of calcination activation is placed in water heating kettle by (1); (2) configuring molar concentration is the titanium sulfate solution of 0.2mol/l; (3), under constant temperature and pressure, Beta molecular sieve thorough impregnation is in titanium sulfate solution 5h, and wherein Ti/Beta molecular sieve mass ratio=1:10, vacuum drying 12h, 550 DEG C of roasting 7h, obtain modification Beta molecular sieve catalyst ST-B-1.
Continuous tubular reactor is adopted to carry out 1-methyl naphthalene isomerization/disproportionated reaction.Result shows, adopt ST-B-1 catalyst prepared by titanium sulfate modification Beta sieve method, conversion ratio >=61% of 1-methyl naphthalene, effective product (2-methyl naphthalene, naphthalene, dimethylnaphthalene) selective >=98%, yield >=59% of effective product (2-methyl naphthalene, naphthalene, dimethylnaphthalene), as compared to the catalytic conversion effect of comparative example 1 with the 1-methyl naphthalene of comparative example 2, the catalyst effect of embodiment 1, while guarantee higher conversion, produces cracking and coking accessory substance hardly.
Embodiment 2
Adopt calcination activation method, cyclicity experiment is carried out to the ST-B-1 catalyst in embodiment 1.Concrete grammar is: the ST-B-1 catalyst in embodiment 1 is after continuous tubular reactor uses 5 hours (TOS=5hr) continuously, taken out, adopt the screening of mesh sieve method, again calcination activation (vacuum drying 12h, 550 DEG C of roasting 7h), the obtained catalyst sample ST-B-2 catalyst recycled.Load in continuous tubular reactor and carry out repeating experiment, the conversion ratio 58% of 1-methyl naphthalene, selective 98% of effective product (2-methyl naphthalene, naphthalene, dimethylnaphthalene), the yield 56% of effective product (2-methyl naphthalene, naphthalene, dimethylnaphthalene).Compared with the catalytic conversion effect of embodiment 1, embodiment 2 is more or less the same, and in error range, shows that the standby ST-B-2 catalyst of calcination activation legal system is substantially identical with the effect of embodiment 1, has good cycle performance.
Comparative example 1
Ion-exchange is adopted to prepare H-Beta catalyst: concrete grammar is: take 1.06gNH
4cl solid, the NH of configuration 0.1mol/l
4cl solution; Take 20gBeta molecular sieve, both are carried out ion-exchange 3 times, each 24h, finally the catalyst of oven dry is carried out roasting.
Load above-mentioned H-Beta catalyst, according to the method identical with embodiment 1, carry out 1-methyl naphthalene isomerization/disproportionated reaction with continuous tubular reactor.Experiment shows that the H-Beta conversion molecular sieve rate adopting ion-exchange to prepare is high, but selective bad.
Comparative example 2
Adopt Ti (SO
4)
2produce SO
4 2-/ TiO
2type acid site legal system is for SO
4 2-/ TiO
2type catalyst, concrete grammar is: take moderate amount of sulfuric acid titanium solid, carry out baking after grinding to titanium sulfate.Then above-mentioned SO is loaded
4 2-/ TiO
2catalyst, according to the method identical with embodiment 1, carries out 1-methyl naphthalene isomerization/disproportionated reaction with continuous tubular reactor.Experiment shows to adopt Ti (SO
4)
2produce SO
4 2-/ TiO
2the SO that type acid site legal system is standby
4 2-/ TiO
2type catalyst can not meet higher conversion and optionally requirement.
The above, titanium sulfate is used for transforming effective product (2-methyl naphthalene at 1-methyl naphthalene to Beta surface modification, naphthalene, dimethylnaphthalene) obtain higher conversion and selective be only preferred embodiment of the present invention, not any pro forma restriction is done to the present invention, although the present invention discloses as above with preferred embodiment, but and be not used to limit the present invention, any those skilled in the art, do not departing within the scope of technical solution of the present invention, make a little change when the technology contents of above-mentioned announcement can be utilized or be modified to the Equivalent embodiments of equivalent variations, in every case be the content not departing from technical solution of the present invention, according to any simple modification that technical spirit of the present invention is done above embodiment, equivalent variations and modification, all still belong in the scope of technical solution of the present invention.
Claims (7)
1. a modification Beta molecular sieve catalyst preparation method, is characterized in that, described method comprises the steps: that the Beta molecular sieve of calcination activation is placed in water heating kettle by (1); (2) configuring molar concentration is the titanium sulfate solution of 0.1-0.3mol/l; (3) under constant temperature and pressure, Beta molecular sieve impregnated in titanium sulfate solution, vacuum drying, roasting, obtained described modification Beta molecular sieve catalyst.
2. the preparation method of modification Beta molecular sieve catalyst according to claim 1, is characterized in that: mass ratio=5 ~ 15% of Ti:Beta molecular sieve.
3. the preparation method of modification Beta molecular sieve catalyst according to claim 1, is characterized in that: described dipping method is 25 DEG C and stirs 4 ~ 6h.
4. the preparation method of modification Beta molecular sieve catalyst according to claim 1, is characterized in that: described vacuum drying is at 110 DEG C of vacuum drying 10 ~ 12h.
5. the preparation method of modification Beta molecular sieve catalyst according to claim 1, is characterized in that: described roasting is at 550 DEG C of roasting 5 ~ 8h.
6. the application of modification Beta molecular sieve catalyst in 1-methyl naphthalene isomerization/disproportionated reaction that obtain of method according to claim 1.
7. application according to claim 6, is characterized in that, with described modification Beta molecular sieve for catalyst, under normal pressure, by beds after being mixed with carrier gas by the 1-methyl naphthalene after gasification, the air speed of 1-methyl naphthalene is 0.5 ~ 1.5h
-1, reaction temperature is 300 ~ 450 DEG C.
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Cited By (5)
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| CN108905920A (en) * | 2018-08-23 | 2018-11-30 | 浙江工业大学上虞研究院有限公司 | A kind of solid gas micro passage reaction |
| CN111348997A (en) * | 2020-04-21 | 2020-06-30 | 青岛科技大学 | Preparation method of 2-alkyl anthraquinone |
| CN111744546A (en) * | 2020-07-15 | 2020-10-09 | 陕西延长石油（集团）有限责任公司 | Copper-bismuth-titanium trimetal oxide catalyst for preparing N-ethylethylenediamine by liquid phase method ethanol, and preparation method and application thereof |
| CN115608332A (en) * | 2021-07-13 | 2023-01-17 | 神美科技有限公司 | Composite adsorbent for deep fluorine removal and preparation method thereof |
| CN116003262A (en) * | 2023-03-20 | 2023-04-25 | 南京师范大学 | Synthesis method of N, N-dimethylaniline |
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| CN111744546A (en) * | 2020-07-15 | 2020-10-09 | 陕西延长石油（集团）有限责任公司 | Copper-bismuth-titanium trimetal oxide catalyst for preparing N-ethylethylenediamine by liquid phase method ethanol, and preparation method and application thereof |
| CN111744546B (en) * | 2020-07-15 | 2022-09-20 | 陕西延长石油（集团）有限责任公司 | Copper-bismuth-titanium trimetal oxide catalyst for preparing N-ethylethylenediamine by liquid phase method ethanol, and preparation method and application thereof |
| CN115608332A (en) * | 2021-07-13 | 2023-01-17 | 神美科技有限公司 | Composite adsorbent for deep fluorine removal and preparation method thereof |
| CN115608332B (en) * | 2021-07-13 | 2024-03-12 | 神美科技有限公司 | Composite adsorbent for deep defluorination and preparation method thereof |
| CN116003262A (en) * | 2023-03-20 | 2023-04-25 | 南京师范大学 | Synthesis method of N, N-dimethylaniline |
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Application publication date: 20160316 |