WO2004037951A1 - 炭化水素の接触分解によるオレフィンの製造方法 - Google Patents
炭化水素の接触分解によるオレフィンの製造方法 Download PDFInfo
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- WO2004037951A1 WO2004037951A1 PCT/JP2003/013425 JP0313425W WO2004037951A1 WO 2004037951 A1 WO2004037951 A1 WO 2004037951A1 JP 0313425 W JP0313425 W JP 0313425W WO 2004037951 A1 WO2004037951 A1 WO 2004037951A1
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- catalyst
- zeolite
- producing
- zirconium
- rare earth
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G11/00—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
- C10G11/02—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils characterised by the catalyst used
- C10G11/04—Oxides
- C10G11/05—Crystalline alumino-silicates, e.g. molecular sieves
-
- 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
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
- B01J29/48—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively containing arsenic, antimony, bismuth, vanadium, niobium tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- 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
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
-
- 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
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
- B01J29/405—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/02—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by cracking a single hydrocarbon or a mixture of individually defined hydrocarbons or a normally gaseous hydrocarbon fraction
- C07C4/06—Catalytic processes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
- C07C2529/48—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11 containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/20—C2-C4 olefins
Definitions
- the present invention relates to a method for producing an olefin by catalytic cracking of a hydrocarbon, and more particularly, to a method for producing a light olefin, mainly light ethylene and propylene, by catalytically cracking a hydrocarbon raw material using a specific catalyst.
- a method for producing an olefin by catalytic cracking of a hydrocarbon and more particularly, to a method for producing a light olefin, mainly light ethylene and propylene, by catalytically cracking a hydrocarbon raw material using a specific catalyst.
- Light-weight olefins such as ethylene and propylene are used as basic materials for various chemicals.
- gaseous hydrocarbons such as ethane, propane, and butane or liquid hydrocarbons such as naphtha are used as raw materials and thermally decomposed in a steam atmosphere in an externally heated tubular furnace.
- the method is widely practiced.
- this method has the disadvantage of requiring a high temperature of 800 ° C or higher in order to increase the yield of the olefins, and that requires the use of expensive equipment materials. .
- a catalytic cracking method using a ZSM-5 type catalyst (see, for example, Japanese Patent Application Laid-Open Nos. 2-14314 and 2-184638) is disclosed, and a ZSM-5 type catalyst containing a rare earth element is also disclosed.
- a ZSM-5 type catalyst containing a rare earth element is also disclosed.
- a catalytic cracking method is disclosed in Japanese Patent Application Laid-Open Publication No. H11-157572.
- these zeolite catalysts The reaction used has the problem that carbon (coke) generated by hydrocarbon over-cracking or hydrogen transfer reaction adheres to the catalyst and degrades its activity.
- the hydrothermal stability of zeolite generally improves with increasing crystallinity or increasing the SiO 2 / A 12 O 3 ratio.
- S I_ ⁇ 2 / A 1 2 O 3 molar ratio of 1 0 or more high-silica-type Zeoraito is to be excellent in heat resistance
- ZSM_5 type zeolite containing transition metals such as Fe, Cu, Co, Ni, Cr, and Mn and cerium or cesium for example, Japanese Patent Application Laid-Open No. 4-15015
- Japanese Patent Application Laid-Open Nos. Hei 4-55,510, Hei 4-78443, Hei 4-78444 have low acid strength because they contain an alkali metal such as potassium-cesium, and are used as catalytic cracking catalysts. Cannot be used.
- Mn-containing ZSM-5 type catalyst improves hydrothermal resistance. The catalytic performance in force catalytic cracking is unknown (“Studies in Sulface. Science and Catalysis”, 1996) Year, 2005, p. 1549).
- a fluid catalytic cracking method using a catalyst composed of zeolite and Mn dispersed in an inorganic matrix is disclosed, but is intended for gasoline production, and contains zeolite containing Mn. This is not preferable because the octane number of gasoline is lowered when the gasoline is subjected to the heat treatment (see Japanese Patent Application Laid-Open No. Hei 7-332229 and Japanese Patent Application Laid-Open No. 11-310210). It is also disclosed that catalytic cracking using a large pore diameter (Y-type) zeolite modified with Mn and rare earth elements can produce gasoline with a high octane number, but almost no ethylene or propylene is obtained. Further, there is no description regarding durability (see US Pat. No. 4,965,075).
- the present invention uses gaseous or liquid hydrocarbons as raw materials to perform catalytic cracking at lower temperatures than conventional methods, suppresses by-products such as aromatic hydrocarbons and heavy substances, and reduces light-weight olefins such as ethylene and propylene.
- An object of the present invention is to provide a method for producing olefins by catalytic cracking of hydrocarbons, which can be selectively produced at a high yield and stably for a long period of time.
- the inventors of the present invention have conducted intensive studies to solve the above-mentioned problems.
- the pentasil-type zeolite containing a rare earth element and containing manganese and / or zirconium has remarkably improved hydrothermal resistance and hydrocarbon contact.
- the present inventors have found that olefins can be stably obtained in a decomposition reaction for a long time in a high yield, and the present invention has been completed.
- the S i O 2 / A 1 2 O 3 molar ratio in Zeorai bets in said catalyst is from 25 to 800 (1) method for producing a Orefin described, and
- hydrocarbon raw material used in the present invention gaseous or liquid hydrocarbons can be used at normal temperature and normal pressure.
- a paraffin having 2 to 30, preferably 2 to 20 carbon atoms or a hydrocarbon raw material containing this as a main component (10% by mass or more) is used.
- hydrocarbon raw materials include paraffins such as ethane, propane, butane, pentane, and hexane, and light hydrocarbon fractions such as naphtha and light oil.
- the raw material components are not limited to saturated hydrocarbons, and those containing components having unsaturated bonds can also be used.
- the catalyst of the present invention contains a pentasil-type zeolite containing a rare earth element and containing manganese and / or zirconium as a main component.
- zeolite ZSM_5 and Z or ZSM-11 are particularly preferable.
- Zeolite generally has a SiO 2 / A 12 O 3 molar ratio of 25 to 800, preferably 40 to 600, and more preferably 80 to 300 ′. 3 013425
- Any rare earth element can be used, but preferred examples include lanthanum, cerium, praseodymium, neodymium, samarium, gadolinium, and disposable shim.
- the rare earth elements may be used alone or in combination of two or more.
- Rare earth modification of the catalyst can be performed using various salts such as acetates, nitrates, halides, sulfates, carbonates, alkoxides, acetylacetonato, etc., by ion exchange, impregnation, or impregnation. Hydrothermal synthesis and other methods can be used.
- the catalyst contains one or both of manganese and zirconium in addition to the rare earth elements.
- the introduction of manganese Z or zirconium into zeolite can be carried out by ion exchange, impregnation, hydrothermal synthesis, or other methods using the various compounds.
- the order of modification of rare earth, manganese, and zirconium to zeolite is not particularly limited, but it is more preferable to perform modification with rare earth elements after performing modification with manganese and / or zirconium.
- the rare earth element, manganese and / or zirconium in this catalyst be supported or contained on zeolite, and the zeolite and the rare earth, manganese and / or zirconium compounds (oxides, etc.) are physically
- the content of the rare earth element is usually from 0.4 to 20, preferably from 0.6 to 5, more preferably from 1 to 3, in atomic ratio to aluminum in zeolite, If the content is less than these values, heavy coke and aromatics as by-products increase, and if the content is too large, the catalytic activity decreases and the yield of olefin decreases.
- the total content of manganese and Z or zirconium is usually 0.1 to 20, preferably 0.5 to 10, more preferably 1 to 10, based on the number of moles of aluminum in zeolite. 5 If the content is lower than these values, the hydrothermal stability will be low, and if the content is too high, the catalytic activity will be low.
- the shape of the catalyst of the present invention is not particularly limited, and may be any shape such as a powder or a molded product.
- These catalysts also contain zeolites, rare earth elements, manganese and other components other than Z or zirconium, such as alkali elements, alkaline earth elements, transition metals, precious metals, halogens, phosphorus, binders, etc. Is also good. It can also be used by mixing with fillers such as silica, alumina, magnesia or quartz sand.
- the mode of the catalytic cracking reaction of the present invention is not particularly limited, by using a reactor having a fixed bed, a moving bed, a fluidized bed or the like, and supplying the hydrocarbon raw material to the catalyst layer packed with the above catalyst ′, Done.
- the hydrocarbon raw material may be diluted with nitrogen, hydrogen, helium, steam, or the like.
- the reaction temperature is usually in the range of 350 to 780 ° C, preferably in the range of 500 to 750 ° C, and more preferably in the range of 600 to 700 ° C. It can be performed at temperatures above 780 ° C, but methane and coke production will increase sharply. On the other hand, if the temperature is lower than 350 ° C, sufficient activity cannot be obtained, so that the yield of olefins per single pass is reduced.
- the reaction pressure can be carried out at normal pressure, reduced pressure or increased pressure, but usually from normal pressure to slightly increased pressure is employed.
- the hydrocarbon raw material can be efficiently decomposed at a low temperature, and light olefins such as ethylene and propylene can be produced in high yield.
- the water was evaporated over time to give a white powder.
- the obtained powder was dried in air at 120 ° C. for 8 hours, then heated in a Matsufuru furnace to 600 ° C. over 4 hours, and calcined at 600 ° C. for 5 hours.
- the obtained solid was pulverized, and further impregnated with an aqueous solution containing 0.4 g of lanthanum (0.99 g of lanthanum acetate 1.5 hydrate dissolved in 6 Om1 of deionized water). Dry-calcination was carried out in the same manner as when manganese was supported, to obtain an off-white solid.
- the mixture was crushed in a mortar and passed through a 150-inch sieve to obtain a La-Mn / HZSM-5 catalyst.
- the contents of La and Mn were 1.1 and 1.0, respectively, in atomic ratio to aluminum in zeolite.
- the La—Mn / HZ SM-5 catalyst prepared in Example 1 was compressed, pulverized, and sieved to form a granular catalyst of about ⁇ .
- This catalyst lg was packed in a fixed-bed tube reactor, and subjected to high-temperature steam treatment at 700 ° C for 24 hours by flowing nitrogen and steam (steam partial pressure: 40 kPa). After completion of the high-temperature steam treatment, the reactor was purged with nitrogen, and the temperature of the catalyst bed was set at 500 ° C to perform a pulse decomposition reaction of n-xane. Nitrogen was passed as carrier gas at 75 cm 3 min, and a pulse of n-hexane (introduced liquid amount 11) was injected to measure the conversion of n-hexane at the outlet. Table 1 shows the results.
- Table 1 also shows the results of evaluation of unmodified HZSM-5 after performing the same treatment.
- Om HZSM-5 catalyst (La—Zr / HZSM-5 catalyst) modified with lanthanum and zirconium was prepared in the same manner as in Example 1 except that the above-mentioned solution was used.
- the contents of La and Zr were 1.1 and 1.0, respectively, in atomic ratio to aluminum in zeolite.
- Table 1 shows the results of pulse decomposition of n-hexane after high-temperature steam treatment of this catalyst.
- aqueous solution prepared by dissolving Okishi zirconyl nitrate of 0.65 mmol and 95 mmol of manganese sulfate (of 0. 47 Mn S_ ⁇ 4 - 5H 2 ⁇ and 0. 174 g of Z r O (N_ ⁇ 3) 2 - 2H 2 0 and which is dissolved in deionized water 60 m 1) but using is a similar way as in example 1 was modified lanthanum, manganese and zirconium catalyst ( La—Mn—Zr / HZSM-5 catalyst) was prepared. The contents of La and (Mn + Zr) were 1.1 and 1.0 (Mn + Zr), respectively, in atomic ratio to aluminum in zeolite.
- Table 1 shows the results of pulse decomposition of n-hexane after high-temperature steam treatment of this catalyst.
- the obtained solid was pulverized in a mortar and passed through a sieve of 15 ⁇ to obtain a P—La_Mn / HZ SM-5 catalyst.
- the contents of La, Mn and P were 1.1, 1.0 and 1.1, respectively, in atomic ratio to aluminum in zeolite.
- Table 1 shows the results of pulse decomposition of n-hexane after high-temperature steam treatment of this catalyst.
- Example 4 P—La— in the same manner as in Example 4 except that the La—Zr / HZSM—5 catalyst prepared by the method of Example 2 was used instead of the La—Mn / HZSM—5 catalyst.
- Zr ZHZ SM-5 catalyst was prepared.
- the contents of La, Zr and P were 1.1, 1.0 and 1.1, respectively, in atomic ratio to aluminum in zeolite.
- Table 1 shows the results of pulse decomposition of n-hexane after high-temperature steam treatment of this catalyst.
- Table 2 shows the results of pulse decomposition of n-hexane after high-temperature steam treatment of this catalyst.
- Phosphorus was supported in the same manner as in Example 4 except that 4 g of the La / HZSM-5 catalyst obtained in the same manner as in Comparative Example 1 was used, and a P-LaZHZSM-5 catalyst was prepared. Made. The content of La and P 'with respect to aluminum in zeolite was 1.1 in both atomic ratios.
- Table 2 shows the results of pulse decomposition of n-hexane after high-temperature steam treatment of this catalyst.
- the obtained powder was dried in air at 120 ° C for 8 hours, then heated in a Matsufuru furnace to 600 ° C over 4 hours, and calcined at 600 ° C for 5 hours.
- the resulting solid is crushed in a mortar and passed through a 150 / in sieve. This was used as MnZHZ SM-5 catalyst.
- the atomic ratio of Mn to aluminum in zeolite was 1.0.
- Table 2 shows the results of the pulse decomposition reaction of n-hexane of this catalyst after high-temperature steam treatment.
- Om 1 HZSM-5 catalyst modified with zirconium (Zr / HZSM-5 catalyst) was prepared in the same manner as in Comparative Example 3 except that the above-mentioned solution was used.
- the Zr content with respect to aluminum in zeolite was
- Table 2 shows the results of pulse decomposition of n-hexane after high-temperature steam treatment of this catalyst.
- Phosphorus was supported in the same manner as in Example 4 except that 4 g of the MnZHZ SM-5 catalyst obtained in the same manner as in Comparative Example 3 was used, to prepare a P-MnZHZ SM-5 catalyst.
- the contents of Mn and P were 1.0 and 1.1, respectively, in atomic ratio to aluminum in zeolite.
- Table 2 shows the results of pulse decomposition of n'-hexane after high-temperature steam treatment of this catalyst.
- the La—MnZHZ SM-5 catalyst prepared in Example 1 was compressed, pulverized, and sieved to form a granular catalyst of about 1 ⁇ .
- the catalyst lg was packed in a stainless steel reaction tube having an inner diameter of 10 mm (with an inner diameter of 3 mm for a thermocouple).
- the length of the catalyst layer was about 30 mm. Quartz sand was filled above and below the catalyst layer.
- n-butane is supplied as a raw material at a flow rate of 3.O cm 3 / min, nitrogen and steam at 3 O cm 3 / min, and 0.5 gZh, respectively. Then, a catalytic cracking reaction of n-butane was performed under high-temperature hydrothermal conditions. .
- reaction product was analyzed by gas chromatography, and the product yield and raw material conversion were calculated by the following equations.
- Example 6 Same as Example 6 except that La—Zi ′ / HZSM-5 prepared in Example 2 or P—La—Mn / HZSM-5 prepared in Example 4 was used as a catalyst. Thus, the catalytic decomposition reaction of n-butane was performed. Table 3 shows the reaction results.
- Example 6 Example 7
- Example 8 Catalyst La-Mn "La-Zr / P-La-Mn /
- HZSM-5 HZSM-5 Raw material n-butane n-butane ''
- gaseous or liquid hydrocarbons are used as raw materials, aromatic hydrocarbons and by-products such as heavy substances are suppressed, and light olefins such as ethylene and propylene can be stably removed for 50% over a long period of time. It can be produced in the above high yield.
- the production of Orefin can be carried out under economically advantageous conditions of 100 ° C. or more lower than the conventional catalytic cracking method.
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- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
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Abstract
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Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US10/532,097 US7531706B2 (en) | 2002-10-28 | 2003-10-21 | Process for producing olefin by catalytic cracking of hydrocarbon |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2002-312539 | 2002-10-28 | ||
JP2002312539A JP4112943B2 (ja) | 2002-10-28 | 2002-10-28 | 炭化水素の接触分解によるオレフィンの製造方法 |
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WO2004037951A1 true WO2004037951A1 (ja) | 2004-05-06 |
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PCT/JP2003/013425 WO2004037951A1 (ja) | 2002-10-28 | 2003-10-21 | 炭化水素の接触分解によるオレフィンの製造方法 |
Country Status (5)
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US (1) | US7531706B2 (ja) |
JP (1) | JP4112943B2 (ja) |
KR (1) | KR100993452B1 (ja) |
CN (1) | CN1325608C (ja) |
WO (1) | WO2004037951A1 (ja) |
Cited By (3)
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WO2006043767A1 (en) * | 2004-10-18 | 2006-04-27 | Lg Chem, Ltd. | Hydrocarbon cracking catalyst using chemical liquid deposition and method for preparing the same |
US7601663B2 (en) | 2004-09-10 | 2009-10-13 | Sk Energy Co., Ltd. | Solid acid catalyst for producing light olefins and process using the same |
CN109364987A (zh) * | 2018-11-29 | 2019-02-22 | 北京惠尔三吉绿色化学科技有限公司 | 一种用于轻烃低温催化反应制丙烯并联产芳烃的催化剂的制备方法和应用 |
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BRPI0602678B1 (pt) * | 2006-07-14 | 2015-09-01 | Petroleo Brasileiro Sa | Aditivo para maximização de glp e propeno adequado a operação da unidade de craqueamento catalítico fluido em baixa severidade e processo de preparo do mesmo |
US7935654B2 (en) * | 2006-09-28 | 2011-05-03 | Lg Chem, Ltd. | Oxide catalyst and phosphoric oxide catalyst for hydrocarbon steam cracking, method for preparing the same and method for preparing olefin by using the same |
KR100948228B1 (ko) * | 2006-09-28 | 2010-03-18 | 주식회사 엘지화학 | 탄화수소 수증기 열분해용 인산화물 촉매, 이의 제조방법및 이를 이용한 경질 올레핀의 제조방법 |
US9669381B2 (en) * | 2007-06-27 | 2017-06-06 | Hrd Corporation | System and process for hydrocracking |
US8021539B2 (en) | 2007-06-27 | 2011-09-20 | H R D Corporation | System and process for hydrodesulfurization, hydrodenitrogenation, or hydrofinishing |
KR100904297B1 (ko) * | 2007-10-26 | 2009-06-25 | 한국화학연구원 | 연속적인 2단계 촉매 반응을 이용한 합성가스로부터 경질올레핀의 제조방법 |
KR100979580B1 (ko) | 2008-02-05 | 2010-09-01 | 에스케이에너지 주식회사 | 경질올레핀 생산용 탄화수소 접촉 분해 촉매 및 그제조방법 |
JP5094506B2 (ja) * | 2008-03-28 | 2012-12-12 | 出光興産株式会社 | 軽質オレフィンの製造方法 |
BRPI0805566B1 (pt) | 2008-12-18 | 2018-02-14 | Petróleo Brasileiro S/A - Petrobras | Processo integrado para a fabricação de olefinas e intermediários para a produção de amônia e uréia |
US20100331590A1 (en) * | 2009-06-25 | 2010-12-30 | Debarshi Majumder | Production of light olefins and aromatics |
WO2014024774A1 (ja) * | 2012-08-10 | 2014-02-13 | 住友化学株式会社 | 炭素原子数2~4のオレフィンの製造方法及びプロピレンの製造方法 |
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Also Published As
Publication number | Publication date |
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CN1708573A (zh) | 2005-12-14 |
KR20050083849A (ko) | 2005-08-26 |
JP4112943B2 (ja) | 2008-07-02 |
JP2004143373A (ja) | 2004-05-20 |
CN1325608C (zh) | 2007-07-11 |
US20060116544A1 (en) | 2006-06-01 |
US7531706B2 (en) | 2009-05-12 |
KR100993452B1 (ko) | 2010-11-09 |
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