WO2003076372A1 - Transalkylation du benzene et d'hydrocarbures aromatiques c9+ - Google Patents
Transalkylation du benzene et d'hydrocarbures aromatiques c9+ Download PDFInfo
- Publication number
- WO2003076372A1 WO2003076372A1 PCT/CN2003/000146 CN0300146W WO03076372A1 WO 2003076372 A1 WO2003076372 A1 WO 2003076372A1 CN 0300146 W CN0300146 W CN 0300146W WO 03076372 A1 WO03076372 A1 WO 03076372A1
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- WIPO (PCT)
- Prior art keywords
- zeolite
- benzene
- carbon
- aromatic hydrocarbons
- catalyst
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
- C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
Definitions
- the present invention relates to a method for the transalkylation of benzene with carbon nine and above.
- toluene (Tol) and carbon octaaromatics (C 8 A) are generated by the transalkylation reaction of benzene (Ben) and carbon nine and above aromatics (C 9 + A), and the toluene selective disproportionation unit and C 8 A isomerization unit, used to increase the production of p-xylene.
- Paraxylene is one of the main basic organic raw materials in the petrochemical industry, and has a wide range of uses in many chemical production fields such as chemical fiber, synthetic resins, pesticides, medicine, and plastics.
- the typical production method of p-xylene (pX) is from thermodynamically balanced ethylbenzene containing xylene, i.e., octaaromatic hydrocarbons, produced by catalytic reforming of naphtha by multi-stage cryogenic crystallization separation or molecular bed sieve simulated moving bed adsorption separation
- the cylinder is called adsorption separation) technology, which separates para-xylene from a mixture of isomers with a boiling point close to it.
- C 8 A isomerization (referred to as isomerization) technology is often adopted to isomerize it into para-xylene.
- isomerization For the treatment of ortho- and meta-xylene, C 8 A isomerization (referred to as isomerization) technology is often adopted to isomerize it into para-xylene.
- C 9 + A toluene disproportionation or the disproportionation of toluene with carbon nine and above aromatics
- transalkylation to generate benzene and C 8 A
- Yue benzene industrialized selective disproportionation process - MSTDP mesoporous ZSM- 5 type zeolite catalyst treated feedstock processing toluene, p-xylene to obtain a high concentration (85 to 90% by weight, in addition to outside specified The same below) of C 8 A and nitrated benzene.
- Industrial applications has not been reported PX-plus process, the process criteria is Yue benzene conversion rate of 30% under the conditions of two benzene Yue pX selectivity 90%, molar ratio of benzene to 7 pX 1.3.
- high para-selectivity is accompanied by rigorous selection of raw materials.
- This type of process can only use toluene as the raw material, and C 9 + A is useless in this process, at least it cannot be directly used.
- this process also produces a large amount of benzene by-product, resulting in a low yield of p-dioxobenzene, which is a fatal shortcoming of the selective disproportionation process.
- Tatoray typical process reactor feed aromatic hydrocarbon is toluene and nine carbon (C 9 A) as the starting material, C ie + hydrocarbon content (aromatics of C10 and above) must be strictly controlled.
- Documents based on the Tatoray process include USP4341914, Chinese Patent 98110859.8, USP2795629, USP3551510. Chinese Patent 97106719.8, etc.
- people have conducted further research and optimization of the Tatoray process, focusing on the development of its core technology, a catalyst, and improving the overall performance indicators of the catalyst, such as increasing weight space velocity, Extend the catalyst operating cycle and increase the average molecular weight of the aromatics reaction feed.
- the increase of the average molecular weight is conducive to the increase of C 8 A, but when the content of heavy aromatics is too high, in order to maintain a certain conversion rate, that is, to maintain the catalyst activity, the side reactions, especially the hydrodealkylation reaction, will inevitably be intensified, and the reaction There are too many benzene products in the product, which causes the product C 8 A / Ben to be low, the aromatics loss is large, and the same raw materials are processed, and the C 8 A is small and the Ben amount is high.
- the toluene disproportionation unit is indispensable because it can provide the role of C 8 A.
- An increase in the amount of Ben and a decrease in the amount of C 8 A are obviously not conducive to the entire aromatics complex.
- Hydrodealkylation process can obtain benzene, toluene, xylene from C 9 + A, but side reactions such as condensation of aromatics to form polycyclic or fused ring compounds are prone to occur.
- Japanese patent JP10158201 describes a process whose purpose is to produce polyalkylbenzenes by transalkylation of benzene or toluene with polyalkylaromatic compounds.
- the catalyst used in this patent is a hydrogen-type DGA zeolite that has not been metal-modified, and there is no report on the metal modification and catalyst stability of this zeolite.
- the method for the transalkylation of nine or more aromatic hydrocarbons does not involve the problem that carbon ten or more heavy aromatics can be converted into useful toluene and carbon eight aromatic hydrocarbons.
- Toluene is produced in parallel to produce a small amount of octaaromatic hydrocarbons, so that toluene can be supplied to the selective disproportionation unit, and octaaromatic hydrocarbons can be supplied to the aromatic isomerization unit.
- octaaromatic hydrocarbons can be supplied to the aromatic isomerization unit.
- pX para-xylene
- the benzene, carbon nine and above aromatics transalkylation method provided by the present invention has the characteristics of being applicable to a wide range of process conditions, high catalyst activity, good stability, and high selectivity of target products.
- the technical scheme adopted by the present invention is as follows: A method for the transalkylation of benzene with carbon nine and above aromatic hydrocarbons, using benzene and carbon nine and above aromatic hydrocarbons as the raw materials for the transalkylation reaction to generate toluene and Carbaocene, the reaction conditions are:
- the catalyst used is based on parts by weight, 10-90 parts of hydrogen-containing zeolite.
- the molar ratio of Si0 2 / Al 2 0 3 is 3 to 500, 0.01 to 20 parts of metal or / and oxide of molybdenum is supported on the zeolite, and 10 to 90 parts of alumina is the binder in the catalyst.
- the molar ratio of Si0 2 / Al 2 0 3 of the hydrogen-type zeolite is preferably 15 to 100, and more preferably 15 to 50.
- a preferred zeolite scheme is selected from at least one of ZSM-5 zeolite, Y zeolite, mordenite, P zeolite, MCM-22 zeolite, MCM-49 zeolite or MCM-56 zeolite, and a more preferred scheme is selected from mordenite or / and P Zeolite.
- the constraint index of zeolite is 0.1 to 15.
- the amount of the metal or / and oxide of molybdenum in parts by weight is preferably in the range of 0.1 to 10.0, and more preferably in the range of 0.1 to 4,0 parts.
- At least one metal or / and oxide selected from the group consisting of iron, cobalt, nickel, chromium, tungsten, bismuth, lanthanum, zirconium, or silver is supported on the zeolite in parts by weight, and the amount thereof ranges from 0.01 to 20 parts.
- the preferred range is 0.1-5 parts.
- a preferred embodiment of the metal or oxide supported on the zeolite is at least one selected from the group consisting of cobalt, chromium or bismuth.
- Hydrogen-type zeolite can be directly synthesized, or it can be natural or dealuminated.
- the constraint index and its measuring method are described in detail in US Pat. No. 4,016,218.
- the preferred solution of carbon nine or more aromatics in the raw material is at least one selected from the group consisting of trimethylbenzene, methyl ethylbenzene, cumene, indane, carbon ten or more heavy aromatics, and the preferred solution of carbon eight aromatics is xylene, Ethylbenzene or a mixture thereof.
- the catalyst used in the present invention is metal-modified on a hydrogen-type zeolite, the catalyst's ability to resist the moisture content of the raw material is greatly increased, and it can maintain high activity and stability, that is, a raw material containing 500 ppm of water can be used, that is, Used under relatively severe reaction conditions, for industrial installations, the drying and dehydration operations of the raw materials Ben and C 9 + A can be eliminated.
- the hydrogen-type zeolite may be a dealuminated zeolite obtained by acid treatment of a low-silicon-alumina ratio zeolite, or may be a natural-type zeolite or a sodium-type high-silica zeolite obtained by direct crystallization through inorganic ammonium ion exchange, drying, and roasting Zeolite should have a sodium content of less than 0.2 weight. /.
- High silica zeolites synthesized by direct crystallization are the most suitable.
- the excellent performance of the catalyst of the present invention is the result of the combined action of the catalytic action of the hydrogen-type high-silica zeolite and the catalytic action of the metal and / or metal oxide supported on the zeolite.
- the preparation method of the Ben and C 9 + A transalkylation catalyst used in the present invention is prepared by a general solution impregnation support method, and then the catalyst is obtained by drying and baking. It has the characteristics of mature technology, simple equipment, convenient operation, and easy industrialization.
- the present invention is used for the transalkylation method of benzene, carbon nine and above aromatic hydrocarbons, the selectivity of toluene plus carbon eight aromatic hydrocarbons is up to 94.1%, and the conversion rate of benzene plus carbon nine and above aromatic hydrocarbons is highest
- Sodium mordenite, sodium P zeolite, and sodium ZSM-5 zeolite were prepared according to ZL89106793.0, USP3308069, and USP4441991, respectively.
- the three sodium-type zeolites were ion-exchanged with ammonium chloride or ammonium nitrate aqueous solution at 90-98TC for 1 to 8 hours.
- the mother liquor was filtered, the ion-exchange was repeated several times, and then washed and dried to obtain ammonium-type zeolite.
- the Si0 2 / Al 2 0 3 of the three ammonium zeolites are 25, 25, and 500, respectively.
- the three ammonium zeolites were mixed with quasi-boehmite ( ⁇ - ⁇ 1 2 0 3 ⁇ H 2 0), diluted with nitric acid, ammonium molybdate and water, kneaded uniformly, squeezed, 110 dried, pelletized, 550
- the catalysts Al, A2, A3 were obtained by calcination, and the molybdenum content of the three catalysts was 4.0% by weight.
- Catalyst A4 was prepared by ion exchange, kneading, molding, and baking, and the metal molybdenum content of the catalyst A4 was 4.0% by weight.
- Sodium MCM-22 zeolite, sodium MCM-49 zeolite and sodium MCM-56 zeolite were prepared according to USP4956514, USP5264643 and USP5453554, respectively.
- the three sodium zeolites were ion-exchanged with ammonium chloride or ammonium nitrate aqueous solution at 90-98 C for 1 to 8 hours.
- the mother liquor was filtered, the ion exchange was repeated several times, then washed, and dried at 110TC to obtain ammonium zeolites.
- the Si0 2 / Al 2 0 3 of the three ammonium zeolites are 30, 138, and 18, respectively.
- a molybdenum-added alumina-deficient mordenite catalyst is prepared.
- the above operation was repeated several times to obtain aluminum-deficient mordenite with Si0 2 / Al 2 0 3 of 20.4 and 26.7, respectively.
- alumina deficient mordenite The three types of alumina deficient mordenite are mixed with commercially available pseudoboehmite at 50/50 (weight ratio), diluted with nitric acid, ammonium molybdate, and water, kneaded and evenly squeezed, squeezed, dried, and pelletized, 550
- the catalysts Cl, C2, and C3 were obtained by calcination, and the contents of the three catalysts were all 4.0% by weight. [Examples 17 to 19]
- ammonium-type mordenite in the examples (1 to 3), and mix it with a commercially available pseudo-boehmite (0- ⁇ 1 2 0 3 ⁇ H 2 0) in different proportions, add dilute nitric acid and water, and knead them. Squeezed, dried at 110 1C, pelletized, and roasted at 400TC to obtain a cylindrical object. This cylindrical object was immersed in an aqueous solution of ammonium molybdate overnight, then dried at 110TC, and then calcined at 540 "to obtain catalysts El, E2, E3, and E4 containing 0.05%, 1.0, 3.0, 8.0, and 16.0% by weight of metal molybdenum, respectively. , E5.
- an HM zeolite catalyst Fl with a metal molybdenum content of 0.0% by weight was obtained.
- Example (1-22) and Comparative Example 1-2 the transalkylation activity of the catalyst was evaluated on a pressurized fluidized fixed-bed reaction evaluation device.
- the airspeed WHSV is 2.5 hours- 1 , and the results are shown in Table 1. The results show that the hydrogen-type zeolite-supported molybdenum catalyst prepared by the present invention has good transalkylation reaction activity.
- ammonium mordenite in the examples (1 to 3) was mixed with pseudoboehmite at a weight ratio of 70/30, dilute nitric acid and water were added, kneaded and evenly squeezed, squeezed, dried, pelletized, and impregnated.
- Molybdenum An ammonium acid aqueous solution and a cobalt nitrate aqueous solution were flooded at 110TC and calcined at 5501C to obtain a catalyst G1 having a metal molybdenum and a metal cobalt content of 4.0% by weight and 0.6% by weight, respectively.
- Catalysts G2 to G8 containing molybdenum and at least one metal or a compound selected from the group consisting of cobalt, nickel, chromium, tungsten, bismuth, lanthanum, zirconium, and silver are prepared in a similar manner.
- the catalysts G1 to G8 obtained in Examples (24 to 28) were used, and the activity evaluation device and conditions of Example 23 were used to investigate the transalkylation activity of the catalyst.
- the results are shown in Table 2.
- the results show that the catalyst containing molybdenum and at least one metal selected from the group consisting of iron, cobalt, nickel, chromium, tungsten, bismuth, lanthanum, zirconium, and silver, or a compound thereof has good transalkylation reaction activity.
- the catalyst G3 obtained in Examples (24 to 28) was used, and the activity evaluation device and conditions of Example 23 were used.
- the reaction transalkylation activity of the catalyst was selected using reaction raw materials of different compositions. The results are shown in Table 3. The results show that the catalyst prepared by the present invention has good transalkylation reaction activity, selectivity, and adaptability to raw materials of different compositions under the conditions of having different raw materials of reaction.
- the catalyst G3 obtained in Examples (24 to 28) was used, and the activity evaluation device of Example 23 was used, and different process conditions were used to investigate the catalyst transalkylation activity.
- the results are shown in Table 4. The results show that the catalyst prepared by the present invention has good transalkylation reaction activity, selectivity, and adaptability to different process conditions over a wide range of process conditions.
- the catalysts Al, B1 and Comparative Examples Fl and F2 prepared in Examples (1 to 13) were used to further evaluate the transalkylation reaction activity of the catalysts in order to investigate their stability.
- the reaction conditions were basically the same as those in Example 23, but The initial reaction temperature of catalysts A1 and B1 was 380 V, and the initial reaction temperature of catalysts F1 and F2 was 4101C.
- the conversion rates of the catalysts Al and B1 are controlled at about 61 to 63% by weight, and a method of gradually increasing the reaction temperature is adopted to maintain the conversion rate at about 61 to 63% by weight. Controlling the catalyst Fl, F2 conversion rate of about 48 to 51 wt%, reaction temperature is increased stepwise approach taken to maintain the conversion rate of 48--51 About weight%.
- the test results are shown in Table 5. It can be seen that the catalyst A1 of the present invention reacts for 1000 hours, the reaction temperature is always stable at 380 TC, and the average conversion rate is 62.2 weight. /. , Average (Tol + C 8 A) selectivity 93.0 weight. /. ; Comparative catalyst F1 was reacted for 500 hours, maintaining an average conversion of 48.0% by weight and an average (Tol + C 8 A) selectivity of 84.5% by weight. /. The reaction temperature increased from 4101C to 445 ° F at the end.
- the catalyst B1 of the present invention reacted for 1000 hours, the reaction temperature was increased from 380 to 392 at the end, the average conversion rate was 63.2% by weight, and the average (Tol + C 8 A) selectivity was 90.4% by weight; compared to the catalyst F2, the reaction was performed for 500 hours to maintain average conversion
- the yield was 50.3% by weight, the average (Tol + C 8 A) selectivity was 82.9% by weight, and the reaction temperature was increased from 410 to 4381C at the end.
- the catalyst stability test results show that the catalyst of the invention has high activity, high selectivity and good stability.
- mordenites with Si0 2 / Al 2 0 3 of 10, 20 and 40 were prepared according to ZL89106793.0. After ammonium exchange and drying, the mordenite was exchanged with commercially available pseudo-boehmite ( ⁇ - ⁇ 1 2 0 3 ⁇ H 2 0) Mix at 50/50 (weight ratio), add dilute nitric acid and water, knead evenly, squeeze the sliver, dry at 1 10 1C, pelletize, and roast at 400 TC to obtain a cylindrical object.
- pseudo-boehmite ⁇ - ⁇ 1 2 0 3 ⁇ H 2 0
- This cylindrical object was immersed in an aqueous solution of ammonium molybdate overnight, then dried at 1 101C, and then calcined at 540 to obtain 4.0% by weight of catalysts W1, W2, and W3 containing molybdenum metal.
- the catalysts W1 to W3 obtained in Examples (33 to 35) were used to examine the transalkylation activity of the catalyst using the activity evaluation device and conditions of Example 23. The results are shown in Table 1. The results show that the molybdenum-containing mordenite catalysts of different silicon-aluminum ratios prepared by the present invention have good transalkylation reaction activity.
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Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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AU2003211667A AU2003211667A1 (en) | 2002-03-13 | 2003-02-25 | The transalkylation method of benzene and c9+ aromatic hydrocarbons |
Applications Claiming Priority (4)
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CNB021110050A CN1199918C (zh) | 2002-03-13 | 2002-03-13 | 用于苯与碳九及其以上芳烃烷基转移的催化剂 |
CN02111004.2 | 2002-03-13 | ||
CN02111005.0 | 2002-03-13 | ||
CNB021110042A CN1193967C (zh) | 2002-03-13 | 2002-03-13 | 苯与碳九及其以上芳烃烷基转移方法 |
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WO2003076372A1 true WO2003076372A1 (fr) | 2003-09-18 |
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PCT/CN2003/000146 WO2003076372A1 (fr) | 2002-03-13 | 2003-02-25 | Transalkylation du benzene et d'hydrocarbures aromatiques c9+ |
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US (1) | US20030181774A1 (zh) |
AU (1) | AU2003211667A1 (zh) |
TW (1) | TW200502207A (zh) |
WO (1) | WO2003076372A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014092764A1 (en) * | 2012-12-12 | 2014-06-19 | Uop Llc | Aromatic transalkylation using uzm-39 aluminosilicate zeolite |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US20050197518A1 (en) * | 2004-03-04 | 2005-09-08 | Miller Jeffrey T. | Method of converting C9 aromatics-comprising mixtures to xylene isomers |
US20070049780A1 (en) * | 2005-08-30 | 2007-03-01 | Schwartz Hilary E | Methods of making xylene isomers |
US7626064B1 (en) | 2008-06-26 | 2009-12-01 | Uop Llc | Transalkylation process |
US8067658B2 (en) * | 2009-01-23 | 2011-11-29 | Conocophillips Company | Isomerization process |
JP6006492B2 (ja) * | 2009-03-27 | 2016-10-12 | クラリアント触媒株式会社 | 揮発性無機水素化物含有排ガス除害剤及び揮発性無機水素化物含有排ガス除害方法 |
Citations (3)
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JPH09187658A (ja) * | 1995-05-25 | 1997-07-22 | Nippon Oil Co Ltd | 芳香族炭化水素化合物の転化用触媒および転化方法 |
US5866742A (en) * | 1997-08-04 | 1999-02-02 | Phillips Petroleum Company | Transalkylation/hydrodealkylation of C9 + aromatic compounds with a zeolite |
CN1287884A (zh) * | 1999-06-24 | 2001-03-21 | 中国石油化工集团公司 | 甲苯与碳九及其以上重质芳烃歧化和烷基转移催化剂 |
Family Cites Families (9)
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US279562A (en) * | 1883-06-19 | Cylinder-cock for engines | ||
US3551510A (en) * | 1968-08-15 | 1970-12-29 | Universal Oil Prod Co | Alkylation-transalkylation process |
US4341914A (en) * | 1980-12-22 | 1982-07-27 | Uop Inc. | Transalkylation process with recycle of C10 hydrocarbons |
US4885426A (en) * | 1987-09-02 | 1989-12-05 | Mobil Oil Corporation | Transalkylation of polyaromatics |
US5243116A (en) * | 1987-11-23 | 1993-09-07 | The Dow Chemical Company | Alkylation of aromatic compounds |
US5406016A (en) * | 1993-06-07 | 1995-04-11 | Exxon Research And Engineering Company | Transalkylation of benzene with heavy catalytic naphtha |
US6060417A (en) * | 1996-06-28 | 2000-05-09 | Toray Industries, Inc. | Catalyst composition for transalkylation of alkylaromatic hydrocarbons and process for production of xylene |
US5817903A (en) * | 1997-04-04 | 1998-10-06 | Phillips Petroleum Company | Hydrotreating catalyst composition and processes therefor and therewith |
US5866741A (en) * | 1997-07-23 | 1999-02-02 | Phillips Petroleum Company | Transalkylation/hydrodealkylation of a C9 + aromatic compounds with a zeolite |
-
2003
- 2003-02-25 WO PCT/CN2003/000146 patent/WO2003076372A1/zh not_active Application Discontinuation
- 2003-02-25 AU AU2003211667A patent/AU2003211667A1/en not_active Abandoned
- 2003-03-03 TW TW092104390A patent/TW200502207A/zh unknown
- 2003-03-11 US US10/385,988 patent/US20030181774A1/en not_active Abandoned
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH09187658A (ja) * | 1995-05-25 | 1997-07-22 | Nippon Oil Co Ltd | 芳香族炭化水素化合物の転化用触媒および転化方法 |
US5866742A (en) * | 1997-08-04 | 1999-02-02 | Phillips Petroleum Company | Transalkylation/hydrodealkylation of C9 + aromatic compounds with a zeolite |
CN1287884A (zh) * | 1999-06-24 | 2001-03-21 | 中国石油化工集团公司 | 甲苯与碳九及其以上重质芳烃歧化和烷基转移催化剂 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014092764A1 (en) * | 2012-12-12 | 2014-06-19 | Uop Llc | Aromatic transalkylation using uzm-39 aluminosilicate zeolite |
KR101839195B1 (ko) | 2012-12-12 | 2018-03-15 | 유오피 엘엘씨 | Uzm-39 알루미노실리케이트 제올라이트를 사용하는 방향족 트랜스알킬화 |
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AU2003211667A1 (en) | 2003-09-22 |
TW200502207A (en) | 2005-01-16 |
US20030181774A1 (en) | 2003-09-25 |
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