CN1565738A - Method for reactivating carbon contained molecular sieve catalyzer in liquid-phase alkylating reaction of benzene and ethene - Google Patents

Method for reactivating carbon contained molecular sieve catalyzer in liquid-phase alkylating reaction of benzene and ethene Download PDF

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Publication number
CN1565738A
CN1565738A CNA031479987A CN03147998A CN1565738A CN 1565738 A CN1565738 A CN 1565738A CN A031479987 A CNA031479987 A CN A031479987A CN 03147998 A CN03147998 A CN 03147998A CN 1565738 A CN1565738 A CN 1565738A
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benzene
carbon
molecular sieve
sieve catalyst
agent
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CN1276793C (en
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陈玉玲
张凤美
舒兴田
王卫东
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Abstract

The invention discloses a regeneration method for carbon molecular sieve catalyst used for liquid phase alkylation of benzene and ethylene. The process includes the following steps: after carbon containing molecular sieve catalyst is added into ammonium salt solution in a ratio of 1/(1-10) by volume and is treated for 1 to 10 hours in air and/or oxygen atmosphere or gas mixture with ammonia atmosphere. The method can reduce residual carbon content on carbon containing molecular sieve catalyst to 0.1% by weight and produced regenerant has high structure-reserving property.

Description

The renovation process of carbon-containing molecules sieve catalyst in benzene and the ethene liquid phase alkylation reaction
Technical field
The invention relates to the renovation process of catalyzer, more specifically say so about the renovation process of carbon-containing molecules sieve catalyst in benzene and the ethene liquid phase alkylation reaction.
Background technology
Vinylbenzene is to produce polystyrene, styrene-butadiene rubber(SBR), the raw material of ABS resin.The first step of production of styrene is benzene and ethylene alkylation synthesizing ethyl benzene.
The production technique of ethylbenzene is gone through following several stages, and in the sixties, adopting with the aluminum chloride is the liquid phase alkylation reaction of catalyzer; The seventies, adopt the vapor phase alkylation on mesopore ZSM-5 molecular sieve catalyst; The eighties, developed the liquid-phase alkylation method under the acidic zeolite catalyzer.
Said benzene and the ethene liquid phase alkylation reaction under acidic zeolite catalyzer condition is a succession of reaction: promptly benzene and ethene generation alkylated reaction generate ethylbenzene, and ethylbenzene and ethene continue to take place alkylated reaction and generates many ethylbenzene such as diethylbenzene, triethyl-benzene; In order to improve the yield of ethylbenzene product, again isolated diethylbenzene, triethyl-benzene etc. are carried out transalkylation reaction regeneration ethylbenzene with benzene.Therefore, need two kinds of catalyzer in the liquid phase alkylation reaction of benzene and ethene, one is a beta-zeolite molecular sieve catalyst, is used for catalysis benzene and ethylene alkylation, and it two is the y-type zeolite molecular sieve catalyst, is used for the transalkylation reaction of benzene and many ethylbenzene.
We know that in the hydro carbons course of processing, the common cause of catalyst deactivation is to form coke.For benzene and ethene liquid-phase alkylation catalyzer, also there is this problem.Poly aromatic hydrocarbons and poly naphthenic hydrocarbon (the previous thing of coke) can cause the reduction of acid site and duct utilization ratio, and solubility and insolubility bituminous matter make catalyst deactivation.
A kind of renovation process to alkylation and transalkylation zeolite catalyst is disclosed in EP1068898A2 and JP10202116, this method is to adopt the low temperature aromatic hydrocarbon reflux, promptly be to pick up hour or after hundreds of hours at benzene and ethylene reaction running number, when ethylbenzene yield is reduced to certain index, stop the alkyl agent (as ethene, propylene etc.) charging, continue to add benzene, under 150～300 ℃, keep some hrs, dissolve away the previous thing of solubility coke, and make the previous thing degraded of insoluble coke, and be degraded to the product of solubility, make the part loss of activity or completely lose active catalyzer to obtain regeneration.Yet when acidic zeolite catalyst runs thousands of hours, when soluble bituminous matter rolled up coke, low temperature aromatic hydrocarbon reflux method of reproduction can not make spent catalyst obtain holomorphosis.
In addition, for carbon-containing molecules sieve catalyst in the liquid phase alkylation reaction of above-mentioned said benzene and ethene, if adopting the mode of passing through roasting that it is generally acknowledged burns carbon deposit and the regenerated method, its result is unsatisfactory, micropore specific area and pore volume all have bigger loss in the catalyst microstructure, do not reach the purpose of effective regeneration.
Do not see the report of carbon-containing molecules sieve catalyst effective regeneration method in benzene and the ethene liquid phase alkylation reaction up to now.
Summary of the invention
The objective of the invention is at the deficiencies in the prior art, provide one carbon-containing molecules sieve catalyst effective regeneration in benzene and the ethene liquid phase alkylation reaction particularly can be able to be had the renovation process of efficient recovery microstructured article parameter.
The inventor finds, with the carbon-containing molecules sieve catalyst regeneration effect that roasting can obtain unexpectedly, be satisfied with under gas atmosphere after ammonium salt aqueous solution is handled.
Therefore, in benzene provided by the invention and the ethene liquid phase alkylation reaction renovation process of carbon-containing molecules sieve catalyst be with carbon-containing molecules sieve catalyst and ammonium salt aqueous solution with 1: the volume ratio of (1～10) contacts the back and handles under 300～700 ℃ of temperature and a kind of atmospheric condition, said atmosphere is selected from air and/or oxygen, or the gas mixture of air and/or oxygen and ammonia
In the renovation process provided by the invention, preferred condition be with carbon-containing molecules sieve catalyst and ammonium salt aqueous solution with 1: the volume ratio of (2～5) contacts then to be handled in 450～650 ℃ of atmosphere.
Said ammonium salt is selected from NH 4NO 3, NH 4CI, (NH 4) 2SO 4, (NH 4) 2C 2O 4(NH 4) 2CO 3In a kind of or their mixture.Said ammonium salt aqueous solution preferred concentration is that 0.05～10 heavy %, temperature are room temperature～100 ℃, and more preferably concentration is that 0.2～5 heavy %, temperature are 30～70 ℃.
In the method provided by the invention, said atmosphere volumetric flow rate be 1～800 gas/agent/hour, preferred 100～650 gas/agent/hour.When adopting the mixed atmosphere of air and ammonia, in mixed atmosphere, the volume ratio of air and ammonia preferred 1: (0.01～0.5), more preferably 1: (0.05～0.1).
Method provided by the invention is by ammonium salt processing and gas phase heat treatment process the carbon-contained catalyst of benzene and ethene liquid-phase alkylation to be regenerated.This method has the following advantages:
1, can make the coke volatilization fully basically that rolls up owing to the insolubility bituminous matter on the carbon-containing molecules sieve catalyst, its remaining carbon drops to below the 0.1 heavy %;
2, regenerator has high structure reservation degree, particularly adopts the renovation process of roasting to compare with prior art, and the micropore specific area and the loss of pore volume of catalyzer are little.
Embodiment
The invention will be further described below by example, but not thereby limiting the invention.
Comparative Examples 1
This Comparative Examples is to adopt the process of benzene backflow carrying out carbon containing beta-molecular sieve catalyst regeneration with reference to the principle of EP1068898A2.
Carbon containing beta-molecular sieve catalyst A (carbon content is 2.4 heavy %, down together) 200ml places in the vertical tube furnace, with 0.5 ℃/minute speed, makes beds be heated to 250 ℃, reaches after 250 ℃, during with WHSV11.5 -1Speed add benzene, and kept 24 hours, stop to heat and cutting off the charging of benzene, feed nitrogen, be cooled to room temperature and unload agent, remember and make DB-1.
Comparative Examples 2
The effect of regeneration carbon containing beta-molecular sieve catalyzer is burnt carbon deposit by the mode of oxygen-containing gas roasting in the explanation of this Comparative Examples individually.
Get A200ml and place in the vertical tube furnace, begin to heat up, be warming up to 550 ℃ after 5 hours from 25 ℃ of room temperatures, at 550 ℃, air flow quantity be 425 gas/agent/hour air atmosphere under roasting 2 hours, stop heating after, naturally cooling unloads agent after the cooling, note is made DB-2.
The regenerative process of example 1～7 explanation carbon containing beta-molecular sieve catalyzer.
Example 1
Get 200ml A, in 400ml 2.5 heavy %NH 4NO 3After soaking little shaking 30 minutes in the aqueous solution, solid-liquid separation places molecular sieve catalyst in the vertical tube furnace, begins to heat up from 26 ℃ of room temperatures, be warming up to 550 ℃ after 5 hours, 550 ℃ and volumetric flow rate be 425 gas/agent/hour air atmosphere under roasting 2 hours, stop heating after, naturally cooling, unload agent after the cooling, note is made A1, does carbon content and materialization structural analysis, the results are shown in table 1.
Example 2
Get 200ml A, in 600ml 2.5 heavy %NH 4NO 3After soaking little shaking 30 minutes in the aqueous solution, solid-liquid separation places molecular sieve catalyst in the vertical tube furnace, begins to heat up from 26 ℃ of room temperatures, be warming up to 650 ℃ after 5 hours, 650 ℃ and volumetric flow rate be 200 gas/agent/hour oxygen atmosphere under roasting 4 hours, stop heating after, naturally cooling, unload agent after the cooling, note is made A2, does carbon content and materialization structural analysis, the results are shown in table 1.
Example 3
Get 200ml A, in 800ml 2.5 heavy %NH 4After soaking little shaking 30 minutes in the Cl aqueous solution, solid-liquid separation places molecular sieve catalyst in the vertical tube furnace, begins to heat up from 26 ℃ of room temperatures, be warming up to 650 ℃ after 5 hours, 650 ℃ and volumetric flow rate be 525 gas/agent/hour air atmosphere under roasting 4 hours, stop heating after, naturally cooling, unload agent after the cooling, note is made A3, does carbon content and materialization structural analysis, the results are shown in table 1.
Example 4
Get 200ml A, in 1000ml 2.5 heavy %NH 4After soaking little shaking 30 minutes in the Cl aqueous solution, solid-liquid separation places molecular sieve catalyst in the vertical tube furnace, begins to heat up from 26 ℃ of room temperatures, be warming up to 650 ℃ after 5 hours, 650 ℃ and volumetric flow rate be 300 gas/agent/hour the volume ratio of air and ammonia be roasting 4 hours under 1: 0.05 the mixed atmosphere, after stopping to heat, naturally cooling, unload agent after the cooling, note is made A4, does carbon content and materialization structural analysis, the results are shown in table 1.
Example 5
Get 200ml A, in 1000ml 2.5 heavy %NH 4After soaking little shaking 30 minutes in the Cl aqueous solution, solid-liquid separation places molecular sieve catalyst in the vertical tube furnace, begins to heat up from 26 ℃ of room temperatures, be warming up to 650 ℃ after 5 hours, 650 ℃ and volumetric flow rate be 300 gas/agent/hour air atmosphere under roasting 4 hours, stop heating after, naturally cooling, unload agent after the cooling, note is made A5, does carbon content and materialization structural analysis, the results are shown in table 1.
Example 6
Get 200ml A, in 1000ml 0.1 heavy %NH 4After soaking little shaking 30 minutes in the Cl aqueous solution, solid-liquid separation places molecular sieve catalyst in the vertical tube furnace, begins to heat up from 26 ℃ of room temperatures, be warming up to 650 ℃ after 5 hours, 650 ℃ and volumetric flow rate be 300 gas/agent/hour air and the volume ratio of ammonia be 1: 0.1 mixed atmosphere under roasting 4 hours, stop heating after, naturally cooling, unload agent after the cooling, note is made A6, does carbon content and materialization structural analysis, the results are shown in table 1.
Example 7
Get 200ml A, in 1000ml 2 heavy % (NH 4) 2C 2O 4After soaking little shaking 30 minutes in the aqueous solution, solid-liquid separation places molecular sieve catalyst in the vertical tube furnace, begins to heat up from 26 ℃ of room temperatures, be warming up to 650 ℃ after 5 hours, 650 ℃ and volumetric flow rate be 100 gas/agent/hour air atmosphere under roasting 4 hours, stop heating after, naturally cooling, unload agent after the cooling, note is made A7, does carbon content and materialization structural analysis, the results are shown in table 1.
Table 1
Example number Regenerator Carbon content (heavy %) Physico-chemical parameter
Degree of crystallinity (%) Specific surface (m 2/g) Pore volume (ml/g)
??SBET ??SZ ??SM ??VMKRO ??VPORE
Fresh dose 100 ??437 ??258 ??179 ??0.121 ??0.420
1 A 1 ??0.078 99 ??400 ??250 ??150 ??0.118 ??0.434
2 A 2 ??0.068 99 ??412 ??249 ??163 ??0.120 ??0.435
3 A 3 ??0.060 100 ??415 ??258 ??157 ??0.120 ??0.432
4 A 4 ??0.051 98 ??413 ??252 ??161 ??0.117 ??0.433
5 A 5 ??0.065 99 ??415 ??255 ??160 ??0.118 ??0.433
6 A 6 ??0.055 99 ??422 ??257 ??165 ??0.118 ??0.434
7 A 7 ??0.062 99 ??427 ??256 ??171 ??0.121 ??0.434
Comparative Examples 1 DB-1 ??0.90 100 ??426 ??256 ??170 ??0.112 ??0.420
Comparative Examples 2 DB-2 ??0.079 97 ??373 ??228 ??145 ??0.107 ??0.432
As can be seen from Table 1, the regenerator that obtains according to the inventive method not only carbon content can be reduced to below the 0.1 heavy %, and its physico-chemical parameter is recovered substantially simultaneously.
Comparative Examples 3
Comparative Examples is to adopt benzene to reflux to regenerate the process of Y zeolite catalyzer with reference to the principle of EP1068898A2.
With 0.5 ℃/minute speed, making carbon content is that 5.6 Y zeolite catalyst B (down together) beds that weigh % are heated to 250 ℃, reaches after 250 ℃, during with WHSV11.5 -1Speed add benzene, and kept 24 hours, stop to heat and cutting off the charging of benzene, feed nitrogen, be cooled to room temperature and unload agent, remember and make DB-3.Carbon content and materialization results of structural analysis are listed in table 2.
Comparative Examples 4
The regeneration Y zeolite catalyst effect that the explanation of this Comparative Examples is burnt carbon deposit by the mode of oxygen-containing gas roasting individually.
Get B200ml and place in the vertical tube furnace, begin to heat up, be warming up to 500 ℃ after 5 hours from 21 ℃ of room temperatures, at 500 ℃, air flow quantity be 425 gas/agent/hour air atmosphere under roasting 4 hours, stop heating after, naturally cooling unloads agent after the cooling, note is made DB-4.Carbon content and materialization results of structural analysis are listed in table 2.
The regenerative process of example 8～13 explanation carbon containing Y zeolite catalyzer.
Embodiment 8
Get B200ml in 400mlNH 4NO 3In the aqueous solution 60 ℃ soak little shaking 60 minutes after, solid-liquid separation places solid catalyst in the vertical tube furnace, begin to heat up from 20 ℃ of room temperatures, be warming up to 500 ℃ after 5 hours, at 500 ℃, air flow quantity be 625 gas/agent/hour air atmosphere under roasting 4 hours, after stopping heating, naturally cooling unloads agent after the cooling, note is made B1, do the materialization structural analysis, the results are shown in table 2.
Embodiment 9
Get B200ml in 400ml 1 heavy %NH 4NO 3In the aqueous solution 60 ℃ soak little shaking 60 minutes after, solid-liquid separation places in the vertical tube furnace, begin to heat up from 20 ℃ of room temperatures, be warming up to 500 ℃ after 5 hours, at 500 ℃, air flow quantity be 300 gas/agent/hour, ammonia flow be 15 gas/agent/hour gas mixture atmosphere under roasting 4 hours, stop heating after, naturally cooling, unload agent after the cooling, note is made B2, does the materialization structural analysis, the results are shown in table 2.
Embodiment 10
Get B200ml in 600ml (NH 4) 2C 2O 4In the aqueous solution 60 ℃ soak little shaking 60 minutes after, solid-liquid separation places in the vertical tube furnace, begin to heat up from 20 ℃ of room temperatures, be warming up to 500 ℃ after 5 hours, at 500 ℃, air flow quantity be 500 gas/agent/hour, ammonia flow be 100 gas/agent/hour gas mixture atmosphere under roasting 4 hours, stop heating after, naturally cooling, unload agent after the cooling, note is made B3, does the materialization structural analysis, the results are shown in table 2.
Embodiment 11
Get B200ml in 400ml 1 heavy %NH 4NO 3In the aqueous solution 60 ℃ soak little shaking 60 minutes after, solid-liquid separation places in the vertical tube furnace, begin to heat up from 20 ℃ of room temperatures, be warming up to 500 ℃ after 5 hours, at 500 ℃, air flow quantity be 400 gas/agent/hour, ammonia flow be 40 gas/agent/hour gas mixture atmosphere under roasting 4 hours, stop heating after, naturally cooling, unload agent after the cooling, note is made B4, does the materialization structural analysis, the results are shown in table 2.
Embodiment 12
Get B200ml in 400ml 1 heavy %NH 4NO 3In the aqueous solution 60 ℃ soak little shaking 30 minutes after, solid-liquid separation places in the vertical tube furnace, begin to heat up from 20 ℃ of room temperatures, be warming up to 500 ℃ after 5 hours, at 500 ℃, air flow quantity be 325 gas/agent/hour atmosphere under roasting 4 hours, after stopping heating, naturally cooling unloads agent after the cooling, note is made B5, do the materialization structural analysis, the results are shown in table 2.
Embodiment 13
Get B200ml in 800ml 1 heavy %NH 4NO 3In the aqueous solution 60 ℃ soak little shaking 60 minutes after, solid-liquid separation places in the vertical tube furnace, begins to heat up from 20 ℃ of room temperatures, be warming up to 500 ℃ after 5 hours, at 500 ℃, oxygen flow be 200 gas/agent/hour atmosphere under roasting 4 hours, stop heating after, naturally cooling, unload agent after the cooling, note is made B6, the results are shown in table 2.
Table 2
Example number Regenerator Carbon content (%) Physico-chemical parameter
Lattice constant (nm) Degree of crystallinity (%) Specific surface area (m 2/g) Pore volume (ml/g)
?S BET ?S Z ?S M ?V MKRO ?V PORE
Fresh dose ??2.449 ??55 ?549 ?435 ?114 ?0.202 ?0.455
8 ?B1 ??0.081 ??2.448 ??53 ?545 ?433 ?112 ?0.202 ?0.457
9 ?B2 ??0.070 ??2.449 ??52 ?545 ?430 ?115 ?0.200 ?0.455
10 ?B3 ??0.069 ??2.448 ??53 ?547 ?436 ?111 ?0.202 ?0.449
11 ?B4 ??0.058 ??2.449 ??53 ?548 ?431 ?117 ?0.203 ?0.450
12 ?B5 ??0.078 ??2.447 ??52 ?549 ?437 ?112 ?0.199 ?0.450
13 ?B6 ??0.083 ??2.448 ??52 ?544 ?434 ?110 ?0.203 ?0.453
Comparative Examples 3 ?DB-3 ??0.850 ??2.447 ??53 ?519 ?392 ?127 ?0.183 ?0.423
Comparative Examples 4 ?DB-4 ??0.092 ??2.444 ??50 ?415 ?324 ?91 ?0.151 ?0.400
See from table 2, regenerator B1～B6 micropore specific area and micropore pore volume that method provided by the invention obtains all obtain holomorphosis, particularly structure cell almost no longer shrinks, carbon content drops to below the 0.1 heavy %, illustrates that method provided by the invention provides a good regenerability for the carbon-containing molecules sieve catalyst.

Claims (9)

1, the renovation process of carbon-containing molecules sieve catalyst in a kind of benzene and the ethene liquid phase alkylation reaction, it is characterized in that carbon-containing molecules sieve catalyst and ammonium salt aqueous solution with 1: the volume ratio of (1～10) contacts the back and handles under a kind of atmosphere of 300～700 ℃, said atmosphere is selected from air and/or oxygen, perhaps the mixed atmosphere of air and/or oxygen and ammonia.
2, according to the method for claim 1, it is characterized in that carbon-containing molecules sieve catalyst and ammonium salt aqueous solution with 1: the volume ratio of (2～5) contacts the back 450～650 ℃ of processing.
3, according to the process of claim 1 wherein said atmosphere volumetric flow rate be 1～800 gas/agent/hour.
4, according to the process of claim 1 wherein said atmosphere volumetric flow rate be 100～650 gas/agent/hour.
5, according to the process of claim 1 wherein that said ammonium salt is selected from NH 4NO 3, NH 4Cl, (NH 4) 2SO 4, (NH 4) 2C 2O 4Or (NH 4) 2CO 3Among a kind of or their mixture.
6, according to the method for claim 1 or 2, wherein the concentration of ammonium salt aqueous solution is that 0.05～10 heavy %, temperature are room temperature～100 ℃.
7, according to the method for claim 6, wherein the concentration of ammonium salt aqueous solution is that 0.2～5 heavy %, temperature are 30～70 ℃.
8, when the process of claim 1 wherein that said atmosphere is the mixed atmosphere of air and ammonia, the volume ratio of air and ammonia is 1: (0.01～0.5).
9, according to the said method of claim 8, wherein the volume ratio of air and ammonia is 1: (0.05～0.1).
CNB031479987A 2003-06-30 2003-06-30 Method for reactivating carbon contained molecular sieve catalyzer in liquid-phase alkylating reaction of benzene and ethene Expired - Lifetime CN1276793C (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101433859B (en) * 2007-11-15 2011-06-15 中国石油化工股份有限公司 Catalyst for alkylation reaction and preparation method thereof
CN102744103A (en) * 2011-04-20 2012-10-24 中国石油化工股份有限公司 Regeneration method of zeolite molecular sieve catalyst
CN114453019A (en) * 2020-11-09 2022-05-10 中国石油化工股份有限公司 Reactivation method of ethylbenzene catalyst

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101433859B (en) * 2007-11-15 2011-06-15 中国石油化工股份有限公司 Catalyst for alkylation reaction and preparation method thereof
CN102744103A (en) * 2011-04-20 2012-10-24 中国石油化工股份有限公司 Regeneration method of zeolite molecular sieve catalyst
CN114453019A (en) * 2020-11-09 2022-05-10 中国石油化工股份有限公司 Reactivation method of ethylbenzene catalyst
CN114453019B (en) * 2020-11-09 2023-07-11 中国石油化工股份有限公司 Reactivation method of ethylbenzene catalyst

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