WO2012070706A1 - 방향족 화합물을 포함하는 유분으로부터 고부가 방향족 제품 및 올레핀 제품을 생산하는 방법 - Google Patents
방향족 화합물을 포함하는 유분으로부터 고부가 방향족 제품 및 올레핀 제품을 생산하는 방법 Download PDFInfo
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- WO2012070706A1 WO2012070706A1 PCT/KR2010/008418 KR2010008418W WO2012070706A1 WO 2012070706 A1 WO2012070706 A1 WO 2012070706A1 KR 2010008418 W KR2010008418 W KR 2010008418W WO 2012070706 A1 WO2012070706 A1 WO 2012070706A1
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- aromatic
- oil
- products
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- xylene
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- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 36
- 150000001336 alkenes Chemical class 0.000 claims description 36
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- -1 ethylene, propylene Chemical group 0.000 claims description 9
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- 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
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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
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/30—Aromatics
-
- 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
Definitions
- the present invention relates to a process for producing aromatic products (benzene / toluene / xylene) and olefins from fractions comprising aromatic compounds.
- fluidized catalytic cracking is a representative conversion process for producing gasoline from heavy oil, and the recent expansion of FCC expansion has exploded.
- Products produced through the FCC process include, for example, propylene, MTBE, Alkylate, Light Cracked Naphtha (LCN), Heavy Cracked Naphtha (HCN), Light Cycle Oil (LCO), and Slurry Oil (SLO), These are used as raw materials of synthetic resins, gasoline-containing oxygen fractions, gasoline high octane fractions, gasoline main blending agents, light oil / heavy oil blends, heavy oil blends, and heavy oil blends.
- LCN Light Cracked Naphtha
- SLO Light Cycle Oil
- U.S. Patent No. 4,585,545 discloses a process for producing gasoline containing a large amount of aromatic components from light cycle oil of a fluidized bed catalytic cracking process to produce gasoline with a high octane number.
- the added value improvement is not large because the aromatic components are contained in a large amount.
- the issue of environmental regulation is greater than raising the octane number, so it is not effective as a fuel improvement technology.
- U. S. Patent No. 6,565, 739 also discloses a process for producing naphtha and light olefins using light cycle oil in a fluidized bed catalytic cracking process.
- the produced naphtha contains very few aromatic components because it completely saturates the aromatic components in an intermediate hydrogenation process. Therefore, it is not suitable as a solution to the problems presented above.
- the present inventors need to extract aromatic components of benzene, toluene or xylene, which are increasing in demand from various oils containing aromatic compounds such as LCO, and together with these needs, high availability
- the present invention has been devised in order to meet the market demand for a process where the separation of high value olefins is also possible.
- An object of the present invention is to replace naphtha, which is a raw material for the production of aromatic products, a variety of oils, including light cycle oil (FCC light cycle oil) of fluidized bed catalytic cracking process containing a large amount of aromatic components It is to provide a new method to enable the production of high concentration of high value aromatic product therefrom.
- FCC light cycle oil light cycle oil
- the present invention comprises the steps of: (a) hydrotreating an oil comprising an aromatic compound including a light cycle oil in the presence of a catalyst; (b) decomposing the partially saturated component in step (a) under a catalytic cracking catalyst; (c) separating the component decomposed in step (b) into (i) benzene, toluene, an aromatic component having 9 or more carbon atoms, (ii) an olefin component, and (iii) residual oil; And (d) transalkylating the benzene, toluene, and a component having 9 or more carbon atoms separated in the step (c).
- the method provides a method for preparing a high value-added aromatic product and an olefin product from an oil containing an aromatic compound. .
- the catalyst of step (a) comprises at least one carrier of alumina or silica, characterized in that it comprises at least one metal selected from Group 6, Group 9, and Group 10 metal components do.
- the metal is characterized in that at least one of cobalt, molybdenum, nickel and tungsten.
- the oil containing the aromatic compound is characterized in that it comprises at least 5% by weight aromatic.
- the catalytic cracking catalyst of step (b) is an amorphous solid acid containing silica and alumina or a crystal having a Si / Al molar ratio of 300 or less, pore size of 4 to 10 A (Angstrom) It is characterized in that the spherical molding catalyst containing a zeolite molecular sieve.
- the catalytic cracking catalyst is 10 to 95% by weight of at least one zeolite molecular sieve selected from the group consisting of FAU, MOR, and BEA, and 5 to 90% by weight of an inorganic binder selected from alumina or clay Mixing and spray-dried to a particle size of 10 ⁇ 300 micron is characterized in that the molded.
- the residual fraction in step (c) is i) a 2-ring or more aromatic component, ii) a 1-ring aromatic component to which a hydrocarbon group having two or more carbons is attached, and iii) a Naphtheinc ring. It is characterized by including the attached 1-ring aromatic component.
- the method is characterized in that it further comprises the step of recycling the residual fraction separated in step (c) to the step (a).
- the step (d) is 10 to 95% by weight of mordenite or beta zeolite with a molar ratio of silica / alumina in the range of 20 to 200 and gamma alumina, silica, silica alumina, bentonite , 0.001 to 0.5 parts by weight of platinum, tin, indium and the like as a hydrogenated metal to a carrier consisting of 5 to 90% by weight of one or more inorganic binders selected from the group consisting of kaolin, clinoptilolite and montmorillonite
- a catalyst is used which is characterized in that a mixed metal with one metal selected from the group consisting of lead is supported.
- the method is characterized in that it further comprises the step of recycling the aromatic component of at least 11 carbon atoms in the product of step (d) to the step (b).
- the method is characterized in that it further comprises the step of separating and purifying the ethylene, propylene, butylene in the olefin component, respectively.
- the step of the trans alkylation characterized in that it further comprises the step of separating the para-xylene from the mixed xylene produced in the trans alkylation.
- the product produced in the step of isomerizing the mixed xylene isomerized mixed xylene, and isomerizing the mixed xylene, which has undergone the step of separating the para-xylene It is characterized in that it further comprises the step of recycling to the transalkylation step.
- the aromatic product and olefin product is characterized in that it comprises ethylene, propylene, butylene, naphthalenes, benzene, and xylene.
- the present invention by replacing naphtha, which is a raw material of the existing aromatic products, it is possible to produce a high concentration of aromatic products such as benzene, toluene, and xylene from an oil containing an aromatic compound such as a light cycle oil in a fluidized bed catalytic cracking process. It provides an innovative way to push the limits of aromatics production.
- xylene which is a high value-added product
- propylene which is a high value-added product
- FIG. 1 is a schematic diagram showing a schematic flow of one embodiment according to the present invention.
- FIG. 2 is a schematic diagram showing a schematic flow of one embodiment according to the invention with the addition of a recycling step.
- FIG. 3 is a schematic diagram showing a schematic flow of one embodiment according to the invention with the addition of a recycling step.
- Figure 4 is a schematic diagram showing a schematic flow of one embodiment according to the present invention with the separation and purification of ethylene, propylene, butylene, separation of para xylene, and xylene isomerization step.
- the present invention comprises the steps of: (a) hydrotreating an oil comprising an aromatic compound including a light cycle oil in the presence of a catalyst; (b) decomposing the partially saturated component in step (a) under a catalytic cracking catalyst; (c) separating the component decomposed in step (b) into (i) benzene, toluene, an aromatic component having 9 or more carbon atoms, (ii) an olefin component, and (iii) residual oil; And (d) transalkylating the benzene, toluene, and a component having 9 or more carbon atoms separated in the step (c).
- the method provides a method for producing an aromatic product and an olefin product from an oil containing an aromatic compound.
- the light cycle oil 1 used as a raw material mainly uses, but is not limited to, light cycle oils generated in a fluidized bed catalytic cracking process, and any oil-containing oil may be used in the refinery / petrochemical process.
- the oil fraction containing aromatics is an oil containing 5% by weight or more of aromatic components, and more preferably 15% by weight or more of aromatic components.
- raw pyrolysis gasoline RPG
- heavy raw pyrolysis gasoline heavy RPG
- treated pyrolysis gasoline TPG
- reformate Heavy aromatics, kerosene, jet oil, atmospheric gas oil, FCC gasoline, light cracked naphtha, heavy cracked naphtha, FCC decanted oil , Vacuum gas oil, coker gas oil, coker diesel, coker naphtha, heavy and reduced petroleum crude oil, petroleum atmospheric pressure Petroleum atmospheric distillation bottom, petroleum vacuum distillation bottom, pitch, asphalt, bitumen, tar sand oil, shale oil shale oil), liquor derived from coal liquefaction Product (liquid products derived from coal liquefaction processes), hydrocarbon residues (heavy hydrocarbon residues) of, and it is also possible to use any selected would in any combination thereof.
- FIG. 1 A schematic flow diagram for the method is shown in FIG. Referring to FIG. 1, the process of the present invention is described, wherein the light cycle oil 1 is introduced into a hydrotreatment step 2.
- a gas oil having a boiling point of 480 to 565 ° C., and an oil having a boiling point of 565 ° C. or more may be used.
- Light cycle oils here are hydrocarbon compounds which typically have an aromatic component of 70 to 80% and a boiling point of 170 to 360 ° C. The more aromatic the cycle oil has, the more advantageous it is to make high value aromatic products.
- the light cycle oil is hydrotreated in the presence of a catalyst.
- the hydrotreating reaction partially saturates the mixed aromatic component comprising two or more aromatic rings.
- an aromatic component having one aromatic ring should not be saturated, since the aromatic component having one aromatic ring may be a high added aromatic component or may be converted into a high added aromatic component in a transalkylation process described later. to be.
- the aromatic components including two or more aromatic rings are preferably saturated, leaving only one aromatic ring. This is because it is not easy to decompose unnecessary aromatic rings in the subsequent decomposition process.
- the catalyst used in the hydrotreating step is characterized in that it comprises a carrier of at least one of alumina or silica. And at least one metal selected from Group 6, Group 9, and Group 10 metal components.
- the metal is selected from one or more of cobalt, molybdenum, nickel and tungsten.
- the feed, ie light cycle oil, introduced into the hydrotreating step contains about 45 to 65 percent by weight of at least two rings of aromatics. Also about 60 to 75% by weight of the at least two-ring aromatics are converted to other components, ie mostly high value aromatic components, or one-ring aromatic components.
- the partially saturated feed 3 is introduced into the catalytic cracking process 4.
- a solid molding catalyst including at least one porous solid acid may be used as the catalytic cracking catalyst.
- the solid acid may be an amorphous solid acid represented by silica, alumina or silica-alumina, or a crystalline zeolite molecular sieve having a Si / Al molar ratio of 300 or less and a pore size of 4 to 10 A (Angstrom) or more.
- the crystalline zeolite molecular sieve is one zeolite molecular sieve selected from FAU, MOR, and BEA represented by large-diameter zeolite molecular sieves having a pore size of 6.5 A or more so that aromatic components can react in pores, and pores.
- a medium diameter zeolite molecular sieve having a size of 5 to 6.5 A can be used in combination with one zeolite selected from MFI, MEL, FER.
- the ratio of the large diameter zeolite molecular sieve to the medium diameter zeolite molecular sieve here is 5/95 to 95/5 by weight, preferably 50/50 to 95/5.
- the catalytic cracking catalyst is 10 to 300 micron by mixing 10 to 95% by weight of at least one zeolite molecular sieve selected from the group consisting of FAU, MOR, and BEA, and 5 to 90% by weight of an inorganic binder selected from alumina or clay. It may be prepared by spray drying at a particle size.
- the decomposition step in the presence of the catalytic cracking catalyst serves to break a long branch or naphthenic ring with two or more carbons attached to the 1-ring aromatic.
- one aromatic ring is left in the aromatic component having two or more aromatic rings, and the other aromatic rings are partially saturated.
- the partially saturated Naphthenic ring is broken to make a high added aromatic component, or It is made to be a raw material of aromatic components.
- the decomposition capacity should be properly adjusted by setting the Cat / Oil ratio of 3 to 15 in the reaction temperature range of 349 ° C to 749 ° C so as not to decompose to the unwanted part.
- 1-ring aromatics having 10 or more carbon atoms are about 15.7% by weight of the feed introduced via the hydrotreating step. About 66.6% of the weight is decomposed in step (b) and converted into other components. Most of the amount to be converted becomes a high value aromatic component, or a component that can be converted to a high value aromatic.
- the feed (5) subjected to the decomposition step using the catalytic cracking catalyst comprises (i) benzene, toluene, and a separation step (6) for separating an aromatic component having at least 9 carbon atoms, (ii) an olefin component, and (iii) residual oil.
- naphthalenes include methyl naphthalene, dimethyl naphthalene, and the like.
- naphthalenes may be recycled to the hydrotreating step together with the residual fraction as described below, or may be separately separated and used for other purposes.
- the high added aromatic component such as benzene and xylene and the toluene which is a raw material of the high added aromatic component and the component having 9 to 10 carbon atoms are sent to the transalkylation step to be described later and converted to the high added aromatic component.
- Residual oil is separated from the components separately.
- the residual oil is an unintentional component, i) a 2-ring or more aromatic component, ii) a 1-ring aromatic, but a hydrocarbon group having two or more carbons, which is not a raw material for a high value-added aromatic product, iii) 1-ring Aromatic, but having a Naphtheinc ring, which is not a high value added aromatic product and is not a raw material of a high value added aromatic product, and iv) other components that are not a high value added aromatic product and are not a raw material of a high value added aromatic product.
- the disproportionation reaction between toluene, the transalkylation reaction of toluene and C9 aromatic compound, the dealkylation reaction of C9 or more alkylaromatic compound and the transalkylation reaction between benzene and C9 or more aromatic compound on the catalyst It happens at the same time.
- This dealkylation reaction is an important reaction to produce toluene which is required for heterogeneous / transalkylation reactions.
- the transalkylation reaction between benzene and C9 or more aromatic compounds is also an important reaction to produce toluene and mixed xylene.
- olefins such as ethylene and propylene produced by the dealkylation reaction. If these olefins are not rapidly hydrogenated, they can be realkylated back to aromatics, ultimately reducing the conversion of C9 or more aromatics, and the olefins themselves may cause polymerization or the like to deactivate the catalyst. Results in promoting production.
- the catalyst used in the transalkylation step is not limited, but it is preferable to use the catalyst mentioned in the US Patent No. 6,867,340.
- the transalkylation step is 10 to 95% by weight of mordenite or beta zeolite with a molar ratio of silica / alumina in the range of 20 to 200 and gamma alumina, silica, silica alumina, bentonite, kaolin, clinoptilo
- One or more inorganic binders selected from the group consisting of light and montmorillonite, which are selected from the group consisting of 0.001 to 0.5 parts by weight of platinum, tin, indium, and lead with respect to the amount of the carrier as a metal hydride in a carrier consisting of 5 to 90% by weight of an inorganic binder.
- a catalyst characterized in that a mixed metal with a metal is supported. For other features of the catalysts, see the literature.
- the high value aromatic component, benzene / xylene, produced in this step is recovered and commercialized.
- the residual oil i.e., i) 2-ring or more aromatic components, ii) 1-ring aromatic but with two or more carbon groups attached to the hydrocarbon group having a high value of aromatic products
- a schematic flow chart of the method further comprises the step of recycling the poor component and the recycling of the aromatic component having at least 11 carbon atoms which is not a raw material of the high added aromatic component after the transalkylation step (7).
- the light cycle oil 1 is introduced into the hydrotreatment step 2.
- the light cycle oil (3) partially saturated in the hydrotreating step (2) is subjected to catalytic cracking step (4), comprising (i) benzene, toluene, and a component having at least 9 carbon atoms, (ii) an olefin component, and (iii) It is introduced into separation step 5 for separation into residual fraction.
- Residual fraction (6) separated in the separation step is recycled to be mixed with the light cycle oil (1) and introduced into the hydrotreatment step (2).
- the 2-ring or more aromatic components can be decomposed into 1-ring aromatic components through a hydrotreating and catalytic cracking step, and the hydrocarbon group or Naphthenic ring having two or more carbons is also decomposed to decompose the high-added aromatic component. Or it can be converted to a raw material of the high value aromatic component.
- the introduction of the recycling step to maximize the production of the aromatic product by the method according to the present invention it is preferable to carry out by adding this step, but the present invention is not limited thereto.
- Figure 3 schematically shows one embodiment of the invention including another recycle step of the residual fraction.
- the residual fraction 6 is mixed with the partially saturated feed 3 introduced into the catalytic cracking step 4 and recycled to the catalytic cracking step 4.
- the residual oil 6 is decomposed in the catalytic cracking step, and the Naphthenic ring of the 1-ring aromatic component or the hydrocarbon group having two or more carbons attached to the Naphthenic ring or the hydrocarbon group having two or more carbons is decomposed to thereby add high aromatics. It can be converted into a raw material of a component or a high value aromatic component.
- benzene, toluene, and a component having 9 or more carbon atoms in the components separated in the separation step (4) are introduced into the transalkylation step (5).
- aromatic components having 11 or more carbon atoms which are not a raw material of the high added aromatic component, may be recovered and introduced into the decomposition process (3) using the catalytic catalyst. That is, the aromatic component having 11 or more carbon atoms is mixed with the partially saturated light cycle oil which has been subjected to the hydrotreating step and introduced into the decomposition process 3 using the catalytic catalyst.
- Components which are not produced in the transalkylation step or which are introduced as part of the transalkylation step in the separation step i.e. i) 2-ring or more aromatic components, ii) 1-ring aromatics but not more than two Iii) a component that is not a raw material for high value-added aromatic products due to a hydrocarbon group having carbon, iii) a component that is not a high value-added aromatic product because it has a 1-ring aromatic or a naphtheinc ring, and iv) a high value-added aromatic product.
- Components that are not aromatic products and that are not the raw material of the high value added aromatic product need to be re-decomposed to be the source of the high value added aromatic ingredient.
- the component in order to re-decompose the component, the component can be recycled to the decomposition step using the catalytic catalyst.
- the recirculation step it is possible to prevent unnecessary components from accumulating in the transalkylation step and to convert a component that is not a raw material of the high added aromatic component into a high added aromatic, thereby increasing the yield of the high added aromatic.
- the effect of this recycling is shown in more detail in the examples described below.
- this recycling increases the yield of the high value aromatics benzene and xylene.
- the method of the present invention may further include a separation step 4, that is, a step 8 of separating and purifying ethylene, propylene, and butylene, respectively, at the rear of the main column to produce a product.
- a separation step 4 that is, a step 8 of separating and purifying ethylene, propylene, and butylene, respectively, at the rear of the main column to produce a product.
- the transalkylation step (5) may further comprise the step (9) of separating only para-xylene from the mixed xylene produced in the trans alkylation step (5).
- suitable techniques such as adsorption and crystallization may be used.
- para-xylene has a high added value compared to ortho-xylene or meta-xylene, it is advantageous to obtain only para-xylene separately.
- Ortho-xylene and mixed xylenes may be sent to the xylene isomerization step 10.
- Para-xylene, meta-xylene, and oxo-xylene of the mixed xylene produced in the transalkylation step (5) are in equilibrium relationship, and only the para-xylene is separated in the separation step.
- This process produces benzene and toluene, which can be recycled back to the transalkylation step (11).
- the benzene and toluene may be converted to xylene.
- all fractions from the xylene isomerization step can be recycled to the transalkylation step to obtain additional para-xylene.
- mixed xylene was produced when the para-xylene separation step and the xylene isomerization step were not added, but by adding the above steps, no meta-xylene and olso-xylene were produced and para-xylene having high added value. Xylene only can achieve the effect that can be obtained.
- light cycle oils used in the process of the present invention light cycle oils having a boiling point in the fluidized bed catalytic cracking fraction in the range of 170 to 360 ° C. were prepared.
- the light cycle oil used in this embodiment used the cracked fraction of the fluidized bed catalytic cracking process, and the difference in the physical properties, composition, and yield of the fluidized bed catalytic cracked fraction produced according to the type of fluidized bed catalytic cracking process raw material and process operating conditions. There may be.
- the raw material was introduced into a hydrotreating process.
- the hydrotreating process was carried out in a fixed bed reactor using a nickel-molybdenum combination catalyst.
- the reaction conditions of the hydrotreating process are shown in Table 2 below.
- the hydrogen consumption in the hydrotreating process was 1.186 based on the feed weight 100.
- composition before and after the hydrotreating process is shown in Table 3 below.
- the 1-ring aromatic component with Naphthenic ring is either a high value added aromatic component or a direct source of high value aromatic component by breaking Naphthenic ring in the subsequent fluidized bed catalytic cracking reaction.
- the feed produced in the hydrotreating process was introduced into a fluidized bed catalytic cracking reactor.
- the catalyst here is a silica alumina catalyst (composed of 49% alumina, 33% silica, 2% rare earth and other inorganic binders) containing commercially available Y-type zeolites.
- the reaction temperature was 549 ° C.
- the reaction pressure was 25.3 psig
- the Cat / Oil ratio was 8
- the WHSV was 27.2 hr ⁇ 1 .
- reaction experiments were carried out using a catalyst circulating fluidized bed reactor capable of continuously reacting catalysts and deactivating catalysts.
- Table 4 shows a comparison of the feed components before and after the liquid-bed catalytic cracking reaction.
- the light olefin was recovered from the components produced in the fluidized bed catalytic cracking reaction and the remaining components were introduced into the transalkylation step.
- the feed through the transalkylation step was 285.5% higher in xylene, and 178.5% more in xylene, compared to the feed just before transalkylation.
- the sum of the benzene and xylene components increased about 189.1% compared to before the transalkylation.
- the transalkylation was not a cracking process so there was no increase in additional olefin production.
- Example 2 was repeated using the same raw materials and reaction conditions as in Example 1 above.
- Example 1 among the components generated in the fluidized bed catalytic cracking step after the hydrotreating step, i) a 2-ring or more aromatic component, and ii) a 1-ring aromatic but hydrocarbon group having two or more carbons is attached thereto.
- a component that is not a raw material of an aromatic product iii) a component that is not a high-value aromatic product because it has a 1-ring aromatic or a naphtheinc ring, and iv) a material that is not a raw material of a high value-added aromatic product, and iv) Components that could not be used as raw materials were recycled to mix with light cycle oils introduced into the hydrotreating step.
- Table 6 below shows the components of the light cycle oil, Examples 1 and 2, used as raw materials.
- the recycling step has the advantage of obtaining higher valued aromatics and olefins in higher yields.
- Example 3 was repeated using the same raw materials and reaction conditions as in Example 1 above.
- Example 1 i) a 2-ring or more aromatic component and ii) a 1-ring aromatic but hydrocarbon group having two or more carbons, among the components generated in the fluidized bed catalytic cracking step after the hydrotreating step, have high added value.
- Table 7 below shows the components of the light cycle oil, Example 1, Example 2, and Example 3 used as raw materials.
- Example 7 As can be seen in Table 7, by further including two recycle steps in Example 3, 61.5% ethylene, 57.3% propylene, 20.3% more than in Example 1, respectively.
- benzene and xylene which are highly added aromatics, also showed a large increase of about 159% and about 150%, respectively.
- Example 2 The same feed as in Example 1 was used and the feed was subjected to a hydrotreating step, fluid bed catalytic cracking step, and separation step.
- Example 3 which includes two recycling stages, almost no aromatic components including two-ring or more were present, and the yields of the high value olefin and the high value aromatic were significantly higher than those of Comparative Examples 1 and 2. Able to know.
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Abstract
Description
Claims (18)
- (a) 방향족 화합물이 포함된 유분을 촉매의 존재 하에서 수소처리 반응시키는 단계;(b) 상기 (a)단계에서 부분 포화된 성분을, 접촉 분해 촉매 하에서 접촉 분해시키는 단계;(c) 상기 (b) 단계에서 분해된 성분을 (i) 벤젠, 톨루엔, 및 탄소수 9 이상인 방향족 성분, (ii) 올레핀 성분, 및 (iii) 잔류 유분으로 분리시키는 단계; 및(d) 상기 (c) 단계에서 분리된 벤젠, 톨루엔, 및 탄소수 9 이상인 방향족 성분을 트랜스알킬화시키는 단계;를 포함하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 제조하는 방법.
- 청구항 1에 있어서, 상기 (a) 단계의 촉매는 알루미나 또는 실리카 중 하나 이상의 담체를 포함하고, 6족, 9족, 및 10족 금속 성분 중에서 선택되는 하나 이상의 금속을 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 제조하는 방법.
- 청구항 2에 있어서, 상기 금속은 코발트, 몰리브덴, 니켈 및 텅스텐 중 하나 이상인 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 제조하는 방법.
- 청구항 1에 있어서, 상기 방향족 화합물이 포함된 유분은 방향족을 5 중량% 이상 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 제조하는 방법.
- 청구항 1에 있어서, 상기 방향족 화합물이 포함된 유분은 미처리 열분해 가솔린(raw pyrolysis gasoline)(RPG), 중질 미처리 열분해 가솔린(heavy raw pyrolysis gasoline)(heavy RPG), 처리된 열분해 가솔린(treated pyrolysis gasoline)(TPG), 리포메이트(reformate), 중질 방향족(heavy aromatics), 등유, 제트유, 상압가스오일(atmospheric gas oil), FCC 가솔린, 경질 분해 납사(light cracked naphtha), 중질 분해 납사(heavy cracked naphtha), FCC 데칸티드 오일(FCC decanted oil), 감압경질유분(vacuum gas oil), 코커 가스 오일(coker gas oil), 코커 디젤(coker diesel), 코커 납사(coker naphtha), 중질 및 환원된 석유 원유(heavy and reduced petroleum crude oil), 석유 상압 증류 하부유(petroleum atmospheric distillation bottom), 석유 감압 증류 하부유(petroleum vacuum distillation bottom), 피치(pitch), 아스팔트(asphalt), 비투멘(bitumen), 타르샌드유(tar sand oil), 셰일유(shale oil), 석탄 액화 공정으로부터 유도된 액상 제품(liquid products derived from coal liquefaction processes), 중 탄화수소 잔사유(heavy hydrocarbon residues), 및 이들의 조합에서 선택된 어느 하나인 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 제조하는 방법.
- 청구항 1에 있어서, 상기 (b) 단계의 접촉 분해 촉매는 실리카와 알루미나를 포함하는 무정형 고체산 또는 Si/Al 몰 비 300 이하, 기공크기 4~10 A(Angstrom)의 특성을 갖는 결정성 제올라이트 분자체를 포함하는 구형 성형 촉매인 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
- 청구항 6에 있어서, 상기 접촉 분해 촉매는 FAU, MOR, 및 BEA로 구성된 군으로부터 선택된 1종 이상의 제올라이트 분자체 10~95 중량% 및, 알루미나 또는 클레이 중에서 선택되는 무기 바인더 5~90 중량%를 혼합하여 10~300 micron의 입도로 분무 건조하여 성형 시킨 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
- 청구항 1에 있어서, 상기 (c) 단계에서의 잔류 유분은 i) 2-ring 이상의 방향족 성분, ii) 두 개 이상의 탄소를 갖는 탄화수소기가 붙어 있는 1-ring 방향족 성분, 및 iii) Naphtheinc ring이 붙어 있는 1-ring 방향족 성분을 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
- 청구항 1에 있어서, 상기 방법은 상기 (c) 단계에서 분리된 잔류 유분을 상기 (a) 단계로 재순환 시키는 단계를 더 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
- 청구항 1 또는 9에 있어서, 상기 잔류 유분에서 나프탈렌류를 분리하는 단계를 더 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
- 청구항 1에 있어서, 상기 방법은 상기 (c) 단계에서 분리된 잔류 유분을 상기 (b) 단계로 재순환 시키는 단계를 더 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
- 청구항 1, 9, 및 11 중 어느 한 항에 있어서, 상기 방법은 상기 (d) 단계의 생성물 중 탄소수 11 이상의 방향족 성분을 상기 (b) 단계로 재순환시키는 단계를 더 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
- 청구항 1, 9, 및 11 중 어느 한 항에 있어서, 상기 방법은 상기 올레핀 성분에서 에틸렌, 프로필렌, 부틸렌을 각각 분리 정제하여 제품화하는 단계를 더 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
- 청구항 1, 9, 및 11 중 어느 한 항에 있어서, 상기 트랜스 알킬화 시키는 단계 이후에 상기 트랜스 알킬화에서 생성된 혼합 자일렌으로부터 파라-자일렌을 분리하는 단계를 더 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
- 청구항 13에 있어서, 상기 트랜스 알킬화 시키는 단계 이후에 상기 트랜스 알킬화에서 생성된 혼합 자일렌으로부터 파라-자일렌을 분리하는 단계를 더 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
- 청구항 14에 있어서, 상기 파라-자일렌을 분리하는 단계를 거친 혼합 자일렌을 혼합 자일렌(mixed xylene)을 이성화시키는 단계, 및 상기 혼합 자일렌을 이성화시키는 단계에서 생성된 생성물을 상기 트랜스알킬화 단계로 재순환 시키는 단계를 더 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
- 청구항 15에 있어서, 상기 파라-자일렌을 분리하는 단계를 거친 혼합 자일렌을 혼합 자일렌(mixed xylene)을 이성화시키는 단계, 및 상기 혼합 자일렌을 이성화시키는 단계에서 생성된 생성물을 상기 트랜스알킬화 단계로 재순환 시키는 단계를 더 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
- 청구항 1에 있어서, 상기 방향족 제품 및 올레핀 제품은 에틸렌, 프로필렌, 부틸렌, 나프탈렌류, 벤젠, 및 자일렌을 포함하는 것을 특징으로 하는 방향족 화합물이 포함된 유분으로부터 방향족 제품 및 올레핀 제품을 생산하는 방법.
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EP10859896.2A EP2644584B1 (en) | 2010-11-25 | 2010-11-25 | Method for producing high-added-value aromatic products and olefinic products from an aromatic-compound-containing oil fraction |
US13/989,161 US8975462B2 (en) | 2010-11-25 | 2010-11-25 | Method for producing high-added-value aromatic products and olefinic products from an aromatic-compound-containing oil fraction |
JP2013540874A JP5820890B2 (ja) | 2010-11-25 | 2010-11-25 | 芳香族化合物を含む留分から高付加価値の芳香族製品およびオレフィン製品を生産する方法 |
PCT/KR2010/008418 WO2012070706A1 (ko) | 2010-11-25 | 2010-11-25 | 방향족 화합물을 포함하는 유분으로부터 고부가 방향족 제품 및 올레핀 제품을 생산하는 방법 |
BR112013012925-5A BR112013012925B1 (pt) | 2010-11-25 | 2010-11-25 | Método de produção de produtos aromáticos e produtos olefínicos a partir de uma fração de petróleo contendo composto aromático |
CN201080071134.2A CN103328416B (zh) | 2010-11-25 | 2010-11-25 | 由含有芳族化合物的油馏分制备高附加值芳族产品和烯烃产品的方法 |
SG2013040506A SG190410A1 (en) | 2010-11-25 | 2010-11-25 | Method for producing high-added-value aromatic products and olefinic products from an aromatic-compound-containing oil fraction |
ES10859896.2T ES2692371T3 (es) | 2010-11-25 | 2010-11-25 | Procedimiento para producir productos aromáticos y productos olefínicos de alto valor añadido a partir de una fracción de petróleo que contiene compuestos aromáticos |
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CN103509588A (zh) * | 2012-06-25 | 2014-01-15 | 中国石油化工股份有限公司 | 一种针对多含环烷环的原料油多产低碳烯烃和轻芳烃的裂化方法 |
CN103509588B (zh) * | 2012-06-25 | 2015-10-28 | 中国石油化工股份有限公司 | 一种针对多含环烷环的原料油多产低碳烯烃和轻芳烃的裂化方法 |
WO2015013223A1 (en) * | 2013-07-23 | 2015-01-29 | Uop Llc | Processes and apparatuses for preparing aromatic compounds |
US9067853B2 (en) | 2013-11-19 | 2015-06-30 | Uop Llc | Process for selectively dealkylating aromatic compounds |
US9073805B2 (en) | 2013-11-19 | 2015-07-07 | Uop Llc | Hydrocracking process for a hydrocarbon stream |
US9162955B2 (en) | 2013-11-19 | 2015-10-20 | Uop Llc | Process for pyrolysis of a coal feed |
CN104447159A (zh) * | 2014-11-11 | 2015-03-25 | 中国海洋石油总公司 | 一种c10+重芳烃轻质化的组合工艺方法 |
US10689586B2 (en) | 2015-12-21 | 2020-06-23 | Sabic Global Technologies B.V. | Methods and systems for producing olefins and aromatics from coker naphtha |
CN107285976A (zh) * | 2017-06-19 | 2017-10-24 | 中国海洋石油总公司 | 一种由粗苯加氢副产非芳烃与重整c9+重芳烃生产混二甲苯的方法 |
Also Published As
Publication number | Publication date |
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CN103328416A (zh) | 2013-09-25 |
JP2014505669A (ja) | 2014-03-06 |
EP2644584A1 (en) | 2013-10-02 |
EP2644584B1 (en) | 2018-08-01 |
BR112013012925A2 (pt) | 2016-08-23 |
BR112013012925B1 (pt) | 2018-08-21 |
JP5820890B2 (ja) | 2015-11-24 |
US20130253242A1 (en) | 2013-09-26 |
US8975462B2 (en) | 2015-03-10 |
EP2644584A4 (en) | 2016-01-06 |
SG190410A1 (en) | 2013-06-28 |
ES2692371T3 (es) | 2018-12-03 |
CN103328416B (zh) | 2016-06-08 |
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