CN108187731A - It is a kind of to be used to produce catalyst of alkylbenzene and preparation method thereof - Google Patents
It is a kind of to be used to produce catalyst of alkylbenzene and preparation method thereof Download PDFInfo
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- CN108187731A CN108187731A CN201711478774.5A CN201711478774A CN108187731A CN 108187731 A CN108187731 A CN 108187731A CN 201711478774 A CN201711478774 A CN 201711478774A CN 108187731 A CN108187731 A CN 108187731A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7007—Zeolite Beta
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7038—MWW-type, e.g. MCM-22, ERB-1, ITQ-1, PSH-3 or SSZ-25
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/36—Steaming
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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
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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
- Y02P20/584—Recycling of catalysts
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- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of catalyst for being used to produce alkylbenzene in the catalyst technical field of production alkylbenzene, are made of following components：A) silica alumina ratio is 2~300 zeolite；B) weight percent is 5 ~ 85% binding agent, and the binding agent is aluminium oxide or silica.Preparation method for producing the catalyst of alkylbenzene includes the following steps：A) zeolite that silica alumina ratio is 3~80 with ammonium salt is exchanged, makes content of the metal sodium ion in zeolitic frameworks in 0.05% (weight) hereinafter, then drying；b）Compound of silicate class steam treatment zeolite is used under the conditions of 190 DEG C 350 DEG C.The catalyst, which has, to be prepared reproducible, and reaction temperature is low, benzene hydrocarbon is than the characteristics of low, catalyst regeneration cycle is long, and preparation process advantages of simple.
Description
Technical field
The present invention relates to be related to producing the catalyst of alkylbenzene and the preparation method of the catalyst.
Background technology
Alkylbenzene is important basic organic chemical industry raw material, including isopropylbenzene, ethylbenzene, butylbenzene and long-chain alkyl benzene etc..Its
Middle isopropylbenzene is the important intermediate raw material for producing phenol, acetone and α-methylstyrene.At present in the world more than 90% benzene
Phenol is produced using cumene method.The conventional method of industrial production alkylbenzene has the solid of UOP (UOP)
Phosphoric acid method (SPA methods) and the improvement AlCl of Monsanto/Lummus Crest companies3Method.SPA methods operating condition is harsh, miscellaneous
Matter is more, it is impossible to the yield of alkylbenzene is improved by reverse alkylation.And AlCl3Although method has the reaction condition relatively mitigated, and can lead to
The yield that reverse alkylation improves alkylbenzene is crossed, but the catalytic erosion is strong, pollution is heavy and post-processes numerous and diverse.
Isopropylbenzene, ethylbenzene production technology be mainly based upon the alkylated reaction principle of Friedel-Carfts, and with three
Aluminium chloride, solid phosphoric acid and acid zeolite etc. are used as catalyst.At present, the production of ethylbenzene mainly has vapor phase method and liquid phase method skill
Art.It is using zeolite ZSM-5 as catalyst using Mobil/Badger technologies as the gas phase law technology of representative.Due in vapor phase method
Catalyst regeneration cycle is short, high energy consumption, and xylene content is high in product, therefore is gradually replaced by molecular sieve liquid phase method.Point
Sub- sieve method mainly uses acid zeolite as catalyst, such as Y zeolites, β zeolites, MCM-22 zeolites.Molecular sieve liquid phase method produces ethylbenzene
Technique, catalyst regeneration cycle is long, xylene content is low in product, the production of corrosion-free and problem of environmental pollution isopropylbenzene is current
Most devices use Liquid-Phase Molecular Sieve alkylation process.
Molecular sieve liquid-phase alkylation method is due to reaction condition mitigation, high conversion rate, selectivity is good, impurity is few, pollution-free, nothing
Corrosion, Main By product polyisopropylbenzene, more ethylbenzene can be changed into isopropylbenzene and ethylbenzene via reverse alkylation, produce isopropylbenzene and ethylbenzene
Rate is up to more than 99%, is major institute of industrial group company common concern in recent years, and a competitively technology elder generation of developmental research
Into, " cleaning procedure " technology significant to environmental protection.
The alkylbenzene molecule sieve catalyst of heavy industrialization has Y type molecular sieve, beta-molecular sieve and MCM- at present
22 zeolites.
CN1096470 provides the alkylation catalyst of a kind of halogen-containing β zeolites and gama-alumina, is mainly used for height
Benzene and ethylene alkylation under temperature；CN1113649 provides a kind of water vapour that part dealuminzation is carried out to zeolite catalyst
Processing method；CN1125641 provide it is a kind of prepare high activity, the method for highly selective isopropylbenzene zeolite catalyst, mainly
It is reacted for bubbling bed, CN1227770 then prepares alkylation catalyst using mineral acid treatment β zeolites.All above-mentioned catalyst
Common drawback be catalyst preparation poor repeatability, it is difficult to commercial Application.
Invention content
The object of the present invention is to provide a kind of for producing catalyst of alkylbenzene and preparation method thereof, which has
Prepare reproducible, reaction temperature is low, benzene hydrocarbon is than the characteristics of low, catalyst regeneration cycle is long, and preparation process advantages of simple.
The object of the present invention is achieved like this：A kind of catalyst for being used to produce alkylbenzene, is made of following components：
A) silica alumina ratio is 2~300 zeolite；
B) weight percent is 5 ~ 85% binding agent, and the binding agent is aluminium oxide or silica；
The silica alumina ratio of the zeolite is 3~80；
The zeolite is Y zeolites, β zeolites, modenite, MCM-22 zeolites, ZSM-5 zeolite or MWW type zeolites；
The binding agent is preferably the gama-alumina of content 30~60%.
Preparation method for producing the catalyst of alkylbenzene is：
It comprises the following specific steps that：A) zeolite that silica alumina ratio is 3~80 with ammonium salt is exchanged, makes metal sodium ion in zeolite bone
Content in frame 0.05% weight ratio hereinafter, then drying；b）Silicate class chemical combination is used under the conditions of 190 DEG C -350 DEG C
Object steam treatment zeolite；
The temperature of the compound of silicate class steam treatment is preferably 240 DEG C to 320 DEG C；
The compound of silicate class is preferably isopropyl silicate, the one of which of silicic acid N-butyl or its mixture；
The ammonium salt of the processing zeolite is preferably ammonium chloride, ammonium nitrate or ammonium phosphate.
Compared with prior art, the beneficial effects of the present invention are：By using isopropyl silicate and silicic acid N-butyl steam
After handling zeolite, the strong acidic activity center of zeolite surface is restrained effectively, the aperture of catalyst is increased, so as to reduce alkene
Hydrocarbon is in the oligomerisation reaction of catalyst surface so that reaction product is quickly spread out from catalyst duct, restrained effectively
The carbon distribution that reaction mass is generated in catalyst surface dehydrocyclization, so as to improve the reaction stability of catalyst so that catalysis
Agent can react under compared with low reaction temperatures, relatively low benzene hydrocarbon ratio.
Description of the drawings
Fig. 1, the 2 TEM photos for molecular sieve before and after the processing.
Fig. 3,4 are SEM photograph before and after the processing.
Specific embodiment
The present invention will be further described below by way of examples：
Embodiment 1
Take 200 grams（Butt）Silica alumina ratio is 20 zeolite beta original powder, is exchanged with 1N ammonium chlorides, makes the Na in zeolite+Ion
Content is less than 0.05% (weight).The above-mentioned nitrogen atmosphere at 250 DEG C of 150 grams of the zeolite by exchange is steamed with isopropyl silicate
Vapour cycle is dried after handling 12 hours.The TEM photos of molecular sieve before and after the processing, will be through above-mentioned processing as shown in attached drawing 1,2
Zeolite is mixed with 100 grams of gama-aluminas, add in 200 milliliters of 1N nitric acid mediate shape that extruded mouldings are 1.6 × 2 millimeters of φ,
120 DEG C of drying.By above-mentioned extrusion product 550 DEG C roasting 5 hours finished catalyst it is spare.
Embodiment 2
Take 200 grams（Butt）Silica alumina ratio is 30 MCM-22 type zeolite powders, is exchanged with 1N ammonium chlorides, makes the Na in zeolite+Ion concentration is less than 0.05% (weight).By nitrogen atmosphere isopropyl silicate at above-mentioned 150 grams 250 DEG C of the zeolite by exchange
Steam circulation handle 12 hours after dry, SEM photograph before and after the processing as shown in attached drawing 3,4, by the zeolite through above-mentioned processing with
100 grams of gama-alumina mixing, it is the shape of 1.6 × 2 millimeters of φ, 120 DEG C of bakings to add in 200 milliliters of 1N nitric acid and mediate extruded moulding
It is dry.By above-mentioned extrusion product 550 DEG C roasting 5 hours finished catalyst it is spare..
Embodiment 3
Take 200 grams（Butt）Silica alumina ratio is 25 zeolite beta original powder, is exchanged with 1N ammonium nitrate, makes the Na in zeolite+Ion
Content is less than 0.05% (weight).By nitrogen atmosphere silicic acid N-butyl steam at above-mentioned 150 grams 270 DEG C of the zeolite by exchange
Circular treatment is dried after 12 hours, and the zeolite through above-mentioned processing is mixed with 100 grams of gama-aluminas, adds in 200 milli of 1N nitric acid
It is the shape of 1.6 × 2 millimeters of φ, 120 DEG C of drying to rise and mediate extruded moulding.Above-mentioned extrusion product is obtained for 5 hours in 550 DEG C of roastings
Finished catalyst is spare..
Embodiment 4
Take 200 grams（Butt）Silica alumina ratio is 30 MCM-22 type zeolite powders, is exchanged with 1N ammonium nitrate, makes the Na in zeolite+Ion concentration is less than 0.05% (weight).By nitrogen atmosphere silicic acid N-butyl at above-mentioned 150 grams 270 DEG C of the zeolite by exchange
Steam circulation is dried after handling 12 hours, and the zeolite through above-mentioned processing is mixed with 100 grams of gama-aluminas, adds in 1N nitric acid
It is the shape of 1.6 × 2 millimeters of φ, 120 DEG C of drying that 200 milliliters, which are mediated extruded moulding,.Above-mentioned extrusion product is roasted 5 at 550 DEG C
It is spare that hour obtains finished catalyst..
Embodiment 5
4 grams of the catalyst of Example 1 is placed in fixed bed reactors, under the conditions of 150 DEG C, 2.5MPa, leads to benzene and propylene
It crosses catalyst bed to be reacted, wherein benzene input is 50 Grams Per Hours, and propylene feed amount is 10 Grams Per Hours, is calculated with propylene
Weight liquid air speed is 2.5 hours-1.The reaction was investigated through 1000 hours, and propylene, the work of catalyst is not detected in reaction product
Property, selectivity do not decline.Selectivity is 99.5% (being calculated with propyl).
Embodiment 6
4 grams of the catalyst of Example 2 is placed in fixed bed reactors, under the conditions of 250 DEG C, 3.5MPa, leads to benzene and ethylene
It crosses catalyst bed to be reacted, wherein benzene input is 150 Grams Per Hours, and ethylene feed amount is 12 Grams Per Hours, in terms of ethylene
It is 3.0 hours to calculate weight liquid air speed-1.The reaction was investigated through 2500 hours, and ethylene is not detected in reaction product, catalyst
Activity, selectivity do not decline.Selectivity is 99.0% (being calculated with ethyl).
Comparative example 1
Take 200 grams（Butt）Silica alumina ratio is 25 zeolite beta original powder, is exchanged with 1N ammonium nitrate, makes the Na in zeolite+Ion
Content is less than 0.05% (weight).150 grams of the zeolite through above-mentioned exchange with 100 grams of gama-aluminas is mixed, adds in 1N nitric acid
It is the shape of 1.6 × 2 millimeters of φ, 120 DEG C of drying that 200 milliliters, which are mediated extruded moulding, is then roasted 5 hours for 550 DEG C.
Comparative example 2
Take 200 grams（Butt）Silica alumina ratio is 30 MCM-22 type zeolite powders, is exchanged with 1N ammonium nitrate, makes the Na in zeolite+Ion concentration is less than 0.05% (weight).150 grams of the zeolite through above-mentioned processing with 100 grams of gama-aluminas is mixed, adds in 1N
It is the shape of 1.6 × 2 millimeters of φ, 120 DEG C of drying that 200 milliliters of nitric acid, which mediates extruded moulding,.By above-mentioned 550 DEG C of roastings of extrusion product
5 hours.
Comparative example 3
4 grams of the catalyst of comparative example 1 is taken to be placed in fixed bed reactors, under the conditions of 165 DEG C, 2.6MPa, leads to benzene and propylene
It crosses catalyst bed to be reacted, wherein benzene input is 50 Grams Per Hours, and propylene feed amount is 10 Grams Per Hours, is calculated with propylene
Weight liquid air speed is 2.5 hours-1.The reaction was investigated through 100 hours, and propylene conversion is reduced to 50%, and propyl is selectively
98.0%。
Comparative example 4
4 grams of the catalyst of comparative example 2 is taken to be placed in fixed bed reactors, under the conditions of 250 DEG C, 3.5MPa, leads to benzene and ethylene
It crosses catalyst bed to be reacted, wherein benzene input is 150 Grams Per Hours, and ethylene feed amount is 12 Grams Per Hours, in terms of ethylene
It is 3.0 hours to calculate weight liquid air speed-1.The reaction was investigated through 100 hours, and conversion of ethylene is reduced to 48%, the selection of catalyst
Property be 96.0% (being calculated with ethyl).
The invention is not limited in above-described embodiments, on the basis of technical solution disclosed by the invention, the skill of this field
For art personnel according to disclosed technology contents, one can be made to some of which technical characteristic by not needing to performing creative labour
A little to replace and deform, these are replaced and deformation is within the scope of the present invention.
Claims (8)
1. it is a kind of for producing the catalyst of alkylbenzene, it is made of following components：
A) silica alumina ratio is 2~300 zeolite；
B) weight percent is 5 ~ 85% binding agent, and the binding agent is aluminium oxide or silica.
2. a kind of catalyst for being used to produce alkylbenzene according to claim 1, it is characterised in that：The sial of the zeolite
Molar ratio is 3~80.
3. a kind of catalyst for being used to produce alkylbenzene according to claim 1, it is characterised in that：The zeolite is boiled for Y
Stone, β zeolites, modenite, MCM-22 zeolites, ZSM-5 zeolite or MWW type zeolites.
4. a kind of catalyst for being used to produce alkylbenzene according to claim 1, it is characterised in that：The binding agent is preferred
Gama-alumina for content 30~60%.
5. a kind of preparation method of the catalyst according to claim 1 for being used to produce alkylbenzene, it is characterised in that：Including
Following specific steps：A) zeolite that silica alumina ratio is 3~80 with ammonium salt is exchanged, makes metal sodium ion containing in zeolitic frameworks
The weight ratio 0.05% is measured hereinafter, then drying；b）Using at compound of silicate class steam under the conditions of 190 DEG C -350 DEG C
Manage zeolite.
6. the preparation method of the catalyst according to claim 5 for being used to produce alkylbenzene, it is characterised in that：The silicic acid
The temperature of ester type compound steam treatment is preferably 240 DEG C to 320 DEG C.
7. the preparation method of the catalyst according to claim 5 for being used to produce alkylbenzene, it is characterised in that：The silicic acid
Ester type compound is preferably isopropyl silicate, the one of which of silicic acid N-butyl or its mixture.
8. the preparation method of the catalyst according to claim 5 for being used to produce alkylbenzene, it is characterised in that：The processing
The ammonium salt of zeolite is preferably ammonium chloride, ammonium nitrate or ammonium phosphate.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201711478774.5A CN108187731A (en) | 2017-12-29 | 2017-12-29 | It is a kind of to be used to produce catalyst of alkylbenzene and preparation method thereof |
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| CN201711478774.5A CN108187731A (en) | 2017-12-29 | 2017-12-29 | It is a kind of to be used to produce catalyst of alkylbenzene and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021099526A1 (en) * | 2019-11-22 | 2021-05-27 | Total Se | Alkyl halides conversion into ethylene and propylene |
| CN115518672A (en) * | 2021-06-24 | 2022-12-27 | 中国石油化工股份有限公司 | Regenerated catalyst powder and alkaline substance treating agent containing same |
| CN115672383A (en) * | 2022-09-08 | 2023-02-03 | 宜昌苏鹏科技有限公司 | Preparation method and product of trimethylamine catalyst with high selectivity |
| RU2815789C1 (en) * | 2019-11-22 | 2024-03-21 | Тоталэнерджис Вантеч | Method of converting haloalkyls to ethylene and propylene |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104368379A (en) * | 2014-10-22 | 2015-02-25 | 江苏黄马化工有限公司 | Catalyst for producing alkylbenzene and preparation method and application of catalyst |
-
2017
- 2017-12-29 CN CN201711478774.5A patent/CN108187731A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104368379A (en) * | 2014-10-22 | 2015-02-25 | 江苏黄马化工有限公司 | Catalyst for producing alkylbenzene and preparation method and application of catalyst |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021099526A1 (en) * | 2019-11-22 | 2021-05-27 | Total Se | Alkyl halides conversion into ethylene and propylene |
| CN114981212A (en) * | 2019-11-22 | 2022-08-30 | 道达尔能源一技术 | Conversion of alkyl halides to ethylene and propylene |
| US11643371B2 (en) | 2019-11-22 | 2023-05-09 | Totalenergies Onetech | Alkyl halides conversion into ethylene and propylene |
| CN114981212B (en) * | 2019-11-22 | 2023-09-01 | 道达尔能源一技术 | Conversion of Alkyl Halides to Ethylene and Propylene |
| RU2815789C1 (en) * | 2019-11-22 | 2024-03-21 | Тоталэнерджис Вантеч | Method of converting haloalkyls to ethylene and propylene |
| RU2815836C1 (en) * | 2019-11-22 | 2024-03-22 | Тоталэнерджис Вантеч | Method of converting at least one methyl halogen to ethylene and propylene |
| CN115518672A (en) * | 2021-06-24 | 2022-12-27 | 中国石油化工股份有限公司 | Regenerated catalyst powder and alkaline substance treating agent containing same |
| CN115518672B (en) * | 2021-06-24 | 2024-01-30 | 中国石油化工股份有限公司 | Regenerated catalyst powder and alkaline substance treating agent containing same |
| CN115672383A (en) * | 2022-09-08 | 2023-02-03 | 宜昌苏鹏科技有限公司 | Preparation method and product of trimethylamine catalyst with high selectivity |
| CN115672383B (en) * | 2022-09-08 | 2024-01-26 | 宜昌苏鹏科技有限公司 | Preparation method and product of catalyst for synthesizing trimethylamine with high selectivity |
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