CN101730673B - Process for xylene production - Google Patents
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- CN101730673B CN101730673B CN2007800536765A CN200780053676A CN101730673B CN 101730673 B CN101730673 B CN 101730673B CN 2007800536765 A CN2007800536765 A CN 2007800536765A CN 200780053676 A CN200780053676 A CN 200780053676A CN 101730673 B CN101730673 B CN 101730673B
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- 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
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Abstract
A process for the conversion of a hydrocarbon feedstock to produce xylene compounds. The feedstock is selectively hydrocracked and introduced into a transalkylation zone with a hydrocarbonaceous stream rich in benzene, toluene and C9+ plus hydrocarbons.
Description
Background of invention
The present invention relates to for the convert hydrocarbons raw material to produce the method for xylene compounds.More specifically, the present invention relates to the selective aromatics hydrocracking that will comprise in the hydrocarbon feed and immediately with the hydrocracking zone effluent and be rich in benzene and the hydrocarbon stream transalkylation of toluene to produce dimethylbenzene.
Be used for multiple important chemicals by oil scale operation xylene isomer as raw material.Most important xylene isomer is the p-Xylol for the polyester main raw material, and it is owing to primary demand continues to enjoy greatly high growth rate.O-Xylol is for the production of Tetra hydro Phthalic anhydride, and this Tetra hydro Phthalic anhydride has heavy body but ripe market.M-xylene is used for product lower such as the such capacity of softening agent, azoic dyestuff and wood preservative but that increasing.Ethylbenzene generally is present in the xylene mixture and sometimes and is recovered for the production of vinylbenzene, but usually is considered to C
8The composition of more not expecting of aromatic substance.
In aromatic hydrocarbon, as the raw material that is used for chemicals, the whole importance of dimethylbenzene is comparable to benzene.Dimethylbenzene and benzene not by oil by the capacity petroleum naphtha is reformed to produce to satisfy the demands, and need to make other hydrocarbon transform to increase the yield of dimethylbenzene and benzene.The most at large, with toluene dealkylation with produce benzene or with toluene disproportionation with obtain benzene and from wherein reclaim the C of independent xylene isomer
8Aromatic substance.Recently, selective disproportionation toluene has been proposed with the method for the p-Xylol that obtains to be higher than Equilibrium yield.
The current purpose of many aromatic substance mixtures is to increase the yield of dimethylbenzene and reduce the importance that benzene is produced.The demand growth of the demand comparison benzene derivative of p-Xylol derivative is faster.In industrialized country, transforming refinery effectively to reduce the content of Benzene In Gasoline, this supply that will increase benzene is to satisfy the demands.To such an extent as to the benzene of being produced by disproportionation process is pure not shortage market competitiveness usually.
Summary of the invention
The present invention is the method for the production of dimethylbenzene, the hydrocarbon-containing feedstock that wherein will comprise aromatic substance is preferably introduced denitrogenation and desulfurization zone to produce effluent, described effluent is introduced heat steam-product liquid separator with transalkylation reaction zone effluent hereinafter described comprise hydrogen, hydrogen sulfide, ammonia and C with production
8The steam flow of-aromatic hydrocarbon and comprise C
9 +The first hydrocarbonaceous liquid stream of hydrocarbon.The steam flow partial condensation to reclaim hydrogen, is got rid of hydrogen sulfide and ammonia, and the fractionation of gained liquid hydrocarbon is comprised the material stream of benzene and toluene and comprises C with production
8 +The second liquid stream of hydrocarbon.To comprise C
9 +The first hydrocarbonaceous liquid stream hydrocracking of hydrocarbon comprises the hydrocracking zone effluent of xylene compounds with production.To comprise the hydrocracking zone effluent of dimethylbenzene, at least part of C of comprising
9 +The material stream that comprises benzene and toluene of the second hydrocarbonaceous liquid stream of hydrocarbon and at least part of previous production is introduced transalkylation reaction zone with production transalkylation reaction zone effluent, is introduced into subsequently heat steam-liquid trap mentioned above.
The information disclosure content
US 4,097,543 (Haag etc.) instructed use the silica/alumina ratio be at least 12 and restricted index (constraint index) as the zeolite of 1-12 toluene disproportionation is produced p-Xylol with selectivity, its mesolite has carried out controlled precoking (controlled precoking).Can with zeolite with carry out ion-exchange from the multiple element of IB family-group VIII, and with multiple clay and other porous matrix Material cladding.
US 4,276,437 (Chu) instructed the use zeolite with Alkylaromatics transalkylation and disproportionation with main acquisition Isosorbide-5-Nitrae-alkyl aromatic isomer, described zeolite is by the modification with the compound treatment of IIIB family element.Catalyzer randomly comprises phosphorus, and expects that IIIB family metal exists with oxidation state.
US 4,922, and 055 (Chu) instructed the use zeolite with toluene disproportionation, and described zeolite is preferably the ZSM-5 that comprises the skeleton gallium, and this skeleton gallium demonstrates and is better than non-skeleton gallium.
US 4,127, and 471 (Suggitt etc.) disclose the method that is used for relaxing subsequently alkyl transmission of hydrocracking charging under the cracking conditions, and described alkyl transmission is generally transalkylation or disproportionation or isomerization.
The accompanying drawing summary
Accompanying drawing is the simplification of flowsheet figure of the preferred embodiment of the invention.Accompanying drawing is intended to schematically illustrate the present invention, and is not to be limitation of the present invention.
Detailed Description Of The Invention
Method of the present invention is used in particular for producing dimethylbenzene by hydrocarbon feed.Suitable hydrocarbon feed boiling point is 149 ℃ (300 °F)-399 ℃ (750 °F), and preferably comprises at least 50 volume % aromatic substance.Particularly preferred raw material comprises at least part of light cycle oil (LCO), and it is the by product of fluid catalystic cracking (FCC) technique.LCO is economical and raw material easily, does not comprise a large amount of sulphur, nitrogen and polynuclear aromatic compound because do not expect LCO as final product and its.Therefore, the present invention can turn to valuable dimethylbenzene hydrocarbon compound with the LCO circulation of low value.
In a preferred embodiment of the invention, at first under the hydrotreatment reaction conditions, selected raw material is introduced denitrogenation and desulfurization reaction zone with hydrogen.Preferred denitrogenation and desulphurization reaction conditioned disjunction hydrotreatment reaction conditions comprise that temperature is 204 ℃ (400 °F)-482 ℃ (900 °F), pressure is 3.5MPA (500psig)-17.3MPa (2500psig), and the liquid hourly space velocity of fresh hydrocarbon-containing feedstock is 0.1hr
-1-10hr
-1, have the combination of hydrotreating catalyst or hydrotreating catalyst.
As used herein term " hydrotreatment " refers to such method: wherein mainly to remove heteroatoms such as sulphur and the activated suitable catalyzer of nitrogen tool in the presence of use hydrogen treat gas rates.The suitable hydrotreating catalyst that uses among the present invention is any known conventional hydrotreating catalyst, and be included in those that comprise following metal on the high surface area support material preferential oxidation aluminium: at least a group VIII metal, preferred iron, cobalt and nickel, more preferably cobalt and/or nickel, and at least a VI family metal, preferred molybdenum and tungsten.In same reaction vessel, use more than a kind of hydrotreating catalyst within the scope of the invention.The group VIII metal is usually with 2 % by weight-20 % by weight, and the amount of preferred 4 % by weight-12 % by weight exists.VI family metal is usually with 1 % by weight-25 % by weight, and the amount of preferred 2 % by weight-25 % by weight exists.Typical hydrotreatment temperature is 204 ℃ (400 °F)-482 ℃ (900 °F), and pressure is 3.5MPa (500psig)-17.3MPa (2500psig), is preferably 3.5MPa (500psig)-13.9MPa (2000psig).
According to the preferred embodiments of the invention, will introduce heat steam-liquid trap with transalkylation reaction zone effluent hereinafter described from the effluent of denitrogenation and desulfurization zone and comprise hydrogen, hydrogen sulfide, ammonia and C with production
8The steam flow of-aromatic hydrocarbon and comprise C
9 +The first hydrocarbonaceous liquid stream of hydrocarbon.Preferably under the pressure of the temperature of 149 ℃ of (300 °F)-288 ℃ (550 °F) and 3.5MPa (500psig)-17.3MPa (2500psig), operate heat steam-liquid trap.
Then with at least part of C that comprises
9 +The first hydrocarbonaceous liquid stream of hydrocarbon is introduced hydrocracking zone.Hydrocracking zone can comprise one or more identical or different catalyst beds.In one embodiment, preferred hydrocracking catalyst a small amount of (low-level) zeolite base thing of utilizing unformed basic thing or being combined with one or more group VIIIs or group vib metal hydrogenation component.In another embodiment, hydrocracking zone comprises catalyzer, and described catalyzer comprises any crystalline zeolite cracking basis thing that deposits a small amount of group VIII metal hydrogenation component on it usually.Other hydrogenation component can be selected from group vib and be used for merging with the zeolite base thing.Zeolite as cracking basis thing is called as molecular sieve in the art sometimes, and usually is comprised of silicon-dioxide, aluminum oxide and one or more exchangeable cation such as sodium, magnesium, calcium, rare earth metal etc.Their feature also is 4 dusts-14 dust (10
-10Rice) relatively uniformly geode diameter.The zeolite of the mol ratio of higher silica/aluminum oxide of preferred employing 3-12.Suitable natural zeolite comprises for example mordenite, stillbite, heulandite, ferrierite, dachiardite, chabazite, erionite and faujusite.Suitable synthetic zeolite comprises for example β, X, Y and L crystal formation, for example synthetic faujasites and mordenite.Preferred zeolite is that the geode diameter is 8 dusts-12 dust (10
-10Rice) those, wherein the mol ratio of silica/alumina is 4-6.The preferred example that drops on the zeolite in the preferable range is synthetic Y molecular sieve.
Naturally occurring zeolite is na form, alkaline earth metal form or mixed form normally.Synthetic zeolite almost always at first is made into na form.Under any circumstance, for being used as cracking basis thing, preferably with most of or all original zeolite monovalent metal and polyvalent metal and/or with ammonium salt ion-exchange, with post-heating so that the ammonium ion of being combined with zeolite decompose, stay hydrogen ion and/or exchange site in its position, in fact it make its decationize by further dewatering.The Y zeolite of this hydrogen or " decationize " more specifically is described in US 3,130, in 006.
Polyvalent metal-the hydrogen zeolite that mixes can by at first with ammonium salt ion-exchange, then again part and polyvalent metal salt anticommuting calcined and prepared.In some cases, as in the situation that synthesizing flokite, can be by alkali metal zeolites being carried out direct acid treatment with the preparation hydrogen form.Preferred cracking basis thing is based on initial ion exchange capacity at least 10%, those of preferred at least 20% metallic cation vacancy.The zeolite classification with stable of special expectation be wherein at least 20% loading capacity occupied by hydrogen ion those.
The reactive metal that is used as hydrogenation component in preferred hydrocracking catalyst of the present invention is those of group VIII, i.e. iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium and platinum.Except these metals, other promotor also can use with them, comprises the group vib metal, for example molybdenum and tungsten.The amount of hydrogenation metal in catalyzer can change at wide region.Put it briefly, can use any amount between 0.05 % by weight-30 % by weight.In the situation that precious metal, general preferred use 0.05 % by weight-2 % by weight.The preferred method that is used in conjunction with hydrogenation metal is that zeolite base thing material is contacted with the aqueous solution of the suitable compound of desired metal, and wherein metal exists with cationic form.Add after the selected hydrogenation metal, then the gained catalyst fines is filtered, dry, if expectation can with the lubricant that adds, tackiness agent etc. and granulation, and under the temperature of for example 371 ℃-648 ℃ (700 °F-1200 °F), in air, calcining, so that catalyst activation and ammonium ion is decomposed.Perhaps, can at first with the zeolite component granulation, add subsequently hydrogenation component, and activate by calcining.Aforesaid catalyzer can use with the form that is not diluted, perhaps can be with other activity of powdered zeolite catalyst and 5 % by weight-90 % by weight lower catalyzer, thinner or tackiness agent,, activated clay etc. cogelled such as aluminum oxide, silica gel, silica-alumina mixes and granulation.These thinners can directly use, and perhaps they can comprise the hydrogenation metal of a small amount of adding, for example VIB and/or group VIII metal.
The hydrocracking catalyst of other metal promoted catalysis also can be used for method of the present invention, and described catalyzer comprises for example aluminophosphate molecular sieve, crystalline state chromosilicates (chromosilicate) and other crystalline silicon hydrochlorate.The crystalline state chromosilicates is described in US 4,363 more comprehensively, among 718 (Klotz).
In the presence of hydrogen and preferably under following hydrocracking reactor condition hydrocarbon-containing feedstock contacted with hydrocracking catalyst and carry out hydrocracking: temperature is 232 ℃ (450 °F)-468 ℃ (875 °F), pressure is 3.5MPa (500psig)-20.8MPa (3000psig), and liquid hourly space velocity (LHSV) is 0.1hr
-1-30hr
-1, the hydrogen cycle rate is 337 standard m
3/ m
3(2000 standard cubic feet per barrel)-4200 standard m
3/ m
3(25000 standard cubic feet per barrel).According to the present invention, so that the production maximum of xylene compounds turns to purpose selective hydrocracking condition on the basis of raw material.
To and comprise C from the effluent of hydrocracking zone and the flow containing hydrocarbons that comprises benzene and toluene hereinafter described
9 +The hydrocarbonaceous liquid stream of hydrocarbon is introduced transalkylation reaction zone together to increase the production of xylene compounds.To generally include temperature be that 200 ℃ (392 °F)-525 ℃ (977 °F) and liquid hourly space velocity are 0.2hr to the preferred condition that adopts in the transalkylation reaction zone
-1-10hr
-1
Can use any suitable transalkylation catalyst in transalkylation reaction zone.Preferred transalkylation catalyst comprises molecular sieve, refractory inorganic oxide and the weak metal of the non-skeleton of reduction.The specific examples of operable zeolite is MOR, MTW, MCM-22, MFI, MEL, EUO, FER, MFS, MTT, MTW, TON, MOR and FAU type zeolite.
Usually prepare zeolite by the crystalline mixture that will comprise alumina source, silica source, alkali metal source, water and tetraalkyl ammonium compound or its precursor.The amount that is present in the zeolite in the catalyzer can noticeable change, but usually exists with 30 quality %-90 quality % of catalyzer and the amount of preferred 50 quality %-70 quality %.
Preferably utilize fire resistant adhesive or matrix to promote the manufacturing of transalkylation catalyst, intensity is provided and reduces manufacturing cost.Tackiness agent should be even in composition and relative method in the condition infusibility that uses.Suitable binder comprises inorganic oxide, for example one or more in aluminum oxide, magnesium oxide, zirconium white, chromic oxide, titanium oxide, boron oxide, Thorotrast, zinc oxide and the silicon-dioxide.Aluminum oxide and/or silicon-dioxide are preferred tackiness agents.
A suitable example of tackiness agent or matrix components is phosphorus-containing alumina (hereinafter being called as aluminum phosphate) component.But can phosphorus and aluminum oxide be merged by any accepting method known in the art.Prepare a kind of preferred method of this aluminum phosphate at US 4,629, describe in 717.The technology of describing in ' 717 patents relates to the alumina hydrosol gelation of using well-known oil drop method will comprise phosphorus compound.Usually this technology relates under 80 ℃-105 ℃ reflux temperature and prepares the water-sol by clear up aluminium in aqueous hydrochloric acid.Aluminium in the colloidal sol is 0.7 with muriatic ratio: 1-1.5: 1 mass ratio.In colloidal sol, add phosphorus compound now.Preferred phosphorus compound is phosphoric acid, phosphorous acid and ammonium phosphate.The phosphorus that represents take mol ratio based on element and the relative quantity of aluminium are as 1: 1-1: 100.Then gained aluminum phosphate water-sol mixture is carried out gelling.A kind of method of this mixture of gelling relates to jelling agent is combined with mixture and then the gained binding mixture is dispersed in oil bath or the tower, and described oil bath or tower have been heated to the temperature of rising so that gelation occurs along with the formation of spheroidal particle.Spendable jelling agent is vulkacit H, urea or its mixture in present method.Jelling agent discharges ammonia at elevated temperatures, and this makes hydrogel spheres may be cured as hydrogel sphere or hydrogel spheres may is converted into hydrogel sphere.Then ball being taken out from oil bath continuously also makes it specifically wear out with drying treatment with the further physical properties of improving them in oil and ammonia solution usually.Then wash wearing out and the particle of gelling and dry under 100 ℃-150 ℃ relative low temperature of gained, and under 450 ℃-700 ℃ temperature, carry out 1 hour-20 hours calcination processing.The amount that has (as oxide compound) phosphorus-containing alumina component in catalyzer can be 10 quality %-70 quality % and preferred 30 quality %-50 quality %.
Zeolite and phosphate aluminium adhesive are mixed and form particle by mode well-known in the art, described method example gel, piling, sintering, pill (marumerizing), spraying drying, extrude or the arbitrary combination of these technology.The preferred method of preparation zeolite/aluminum phosphate carrier relates to zeolite is added in alumina sol or the phosphorus compound, forms the mixture of alumina sol/zeolite/phosphorus compound, now by adopting above-mentioned oil drop method that it is formed particle.Calcine as mentioned above described particle to be provided for the carrier of metal component.
Another component of preferred alkyl transfer catalyst is weak non-skeleton metal.Master metal will be present in the final catalyzer to be reduced state, namely surpasses 50% metal, preferred at least 75% and more preferably at least 90% metal be lower than+3 oxidation state is present in the catalyzer.Preferably, metal is selected from platinum, palladium, nickel, tungsten, gallium, rhenium and bismuth, more preferably basically is comprised of gallium or bismuth, and most preferably basically is comprised of gallium.
In the preparation of suitable catalyzer, can in any appropriate manner gallium or bismuth component be deposited on the carrier to realize the disclosed characteristic of catalyzer.By the salt impregnated carrier with gallium metal the gallium component suitably is deposited on the carrier.With being selected from following gallium salt impregnated granules: gallium nitrate, gallium chloride, gallium bromide, gallium hydroxide, acetic acid gallium etc.Suitable bismuth salt comprises for example Bismuth trinitrate, bismuth acetate, Trichlorobismuthine, bismuth tribromide and Bismuth Trioxide.The amount that is deposited on gallium on the carrier and/or bismuth is expressed as 0.1 quality %-5 quality % of final catalyzer with metal element.
By any technology well-known in the art gallium and/or bismuth component are immersed on the carrier granule, described technology for example catalyzer is immersed in the solution of metallic compound or with solution spray on carrier.A kind of preferred preparation method relates to the rotatory drier that uses the carrying vapour chuck.Carrier granule is immersed in the dipping solution that comprises in the moisture eliminator, and by rotatablely moving of moisture eliminator carrier granule is overturn therein.Promote evaporation with the solution that contacts of upset carrier by steam being applied to the moisture eliminator chuck.After particle is completely dried, they were heated 1 hour-15 hours in nitrogen atmosphere under 500 ℃-700 ℃ temperature.Although preferably reduction and dispersed metal in pure hydrogen atmosphere can be used nitrogen dilution hydrogen.The particle that then heating is processed through hydrogen under 400 ℃-700 ℃ temperature in air and steam 1 hour-10 hours.The amount of the steam that exists in the air is 1%-40%.
To introduce heat steam-liquid trap mentioned above and effluent merging preferred and from denitrogenation and desulfurization zone from the effluent of transalkylation reaction zone.In an embodiment of the inventive method, can be with at least part of C of comprising that in heat steam-liquid trap, produces
9 +The first hydrocarbonaceous liquid stream of hydrocarbon is sent to diesel pool (diesel pool).
What produce in heat steam-liquid trap comprises hydrogen, hydrogen sulfide, ammonia and C
8The steam flow of-aromatic hydrocarbon contact with aqueous streams and partial condensation in the cold steam-liquid trap of the temperature that preferably is maintained at 38 ℃ of (100 °F)-71 ℃ (160 °F), to produce the aqueous streams comprise ammonia, to comprise the hydrogen rich stream of hydrogen sulfide and comprise C
8 +The liquid stream of aromatic hydrocarbon, benzene and toluene.The hydrogen rich stream that will comprise hydrogen sulfide is introduced the sour gas recovery zone, described sour gas recovery zone preferably with the temperature of the essentially identical pressure of hydrocracking zone and 38 ℃ of (100 °F)-71 ℃ (160 °F) under operate.To for example contact with absorbing hydrogen sulphide with hydrogen rich stream such as the lean solvent of amine aqueous solution.Preferred amine comprises monoethanolamine and diethanolamine.The rich solvent that will comprise the hydrogen sulfide of absorption reclaims.The preferred hydrogen rich stream of the hydrogen sulfide that comprises the concentration reduction that adopts is to provide denitrogenation and desulfurization zone and hydrocracking zone required at least part of hydrogen.Any suitable to the position can be with fresh supplemented hydrogen introducing technique easily.
Will be from the C that comprises of cold steam-liquid trap recovery
8 +The liquid stream of aromatic hydrocarbon, benzene and toluene is sent into the first fractionation zone and is comprised the flow containing hydrocarbons of benzene and toluene and comprise C with production
8 +The hydrocarbonaceous liquid stream of aromatic hydrocarbon.With at least part of C that comprises
8 +The hydrocarbonaceous liquid stream of aromatic hydrocarbon is sent into the after-fractionating district and is rich in the hydrocarbon product stream of dimethylbenzene and comprises C with production
9 +The second flow containing hydrocarbons of hydrocarbon.With at least part of C that comprises
9 +The second flow containing hydrocarbons of hydrocarbon and at least part of flow containing hydrocarbons that comprises benzene and toluene are introduced aforesaid transalkylation reaction zone.
Accompanying drawing describes in detail
In the accompanying drawings, by simplification of flowsheet figure method of the present invention is described, wherein deleted such as the details of pump, instrument, heat exchange and recovery of heat pipeline, compressor and similar hardware, because this is unimportant to understanding related technology.Use such various device it may occur to persons skilled in the art that.
Referring now to accompanying drawing,, the hydrocarbon-containing feedstock that will comprise light cycle oil is introduced in the technique through pipeline 1, and mixes with the hydrogen rich stream that provides through pipeline 18, and the gained mixture is transported and introduce denitrogenation and desulfurization zone 3 through pipeline 2.Shift out effluent stream and introduce heat steam-liquid trap 6 through pipeline 4 and pipeline 5 from denitrogenation and desulfurization zone 3.Shift out through pipeline 7 from heat steam-liquid trap 6 and to comprise hydrogen, hydrogen sulfide, ammonia and C
8The steam flow of-aromatic hydrocarbon also contacts it with the aqueous streams that provides through pipeline 8, and introduces cold steam-liquid trap 10 with the mixture cooling of gained and through pipeline 9.To comprise the aqueous streams that the water dissolvable compound comprises ammonia shifts out and reclaims from cold steam-liquid trap 10 through pipeline 11.Shift out the hydrogen rich stream that comprises hydrogen sulfide and be introduced into sour gas washer 13 through pipeline 12 from cold steam-liquid trap 10.Poor sour gas washing soln is introduced sour gas washing sections 13 through pipeline 14, and the rich sour gas washing soln that will comprise hydrogen sulfide shifts out and reclaims from sour gas washing section 13 through pipeline 15.Shift out the hydrogen rich stream that comprises the hydrogen sulfide that concentration reduces and it is flowed with the hydrogen make-up material that provides through pipeline 38 through pipeline 16 from sour gas washing section 13 and mix, and transport the gained mixture through pipeline 16.Transport and introduce reaction zone 30 through first part's hydrogen rich stream that pipeline 16 transports through pipeline 17 and 39, second section transports and introduces denitrogenation and desulfurization zone 3 through pipeline 18 and 2.Shift out through pipeline 34 from heat steam-liquid trap 6 and to comprise C
9 +The hydrocarbonaceous liquid stream of hydrocarbon, and reaction zone 30 is carried and introduced to part through pipeline 36 and 39.Comprise C
9 +Another part hydrocarbonaceous liquid of hydrocarbon pipeline 35 of flowing through shifts out from technique.Shift out through pipeline 19 from cold steam-liquid trap 10 and to comprise C
8The hydrocarbonaceous liquid stream of-aromatic hydrocarbon also is introduced into fractionation zone 20.Shift out the hydrocarbonaceous liquid stream that comprises benzene and toluene through pipeline 26 from fractionation zone 20, and its part shifts out from technique through pipeline 27, another part transports and introduces reaction zone 30 through pipeline 28 and 29.Shift out through pipeline 21 from fractionation zone 20 and to comprise C
8 +The hydrocarbonaceous liquid stream of hydrocarbon also is introduced into fractionation zone 22.Shift out hydrocarbon product stream and the recovery of being rich in dimethylbenzene through pipeline 37 from fractionation zone 22.Shift out C from fractionation zone 22 through pipeline 23
9 +Hydrocarbon stream, and first part shifts out from technique through pipeline 24, and second section transports and introduces reaction zone 30 through pipeline 25 and 29.The reactant that before had been described to enter reaction zone 30 flows into hydrocracking zones 31 and mixes with the aforesaid reactant flow of introducing through pipeline 29 through pipeline 39, and with gained mixture introducing transalkylation reaction zone 32.Transport the effluent in autoreaction district 30 and be introduced into heat steam-liquid trap 6 through pipeline 33 and 5 from reaction zone 30.
The advantage that the inventive method is included and the beneficial effect that adopts the method to obtain have been described to above stated specification and drawings clear.
Claims (10)
1. method for the production of dimethylbenzene, it comprises:
(a) make C
9 +Hydrocarbon comprises the hydrocracking zone effluent of dimethylbenzene with production in the hydrocracking catalyst reaction in hydrocracking zone;
(b) at least part of hydrocracking zone effluent is reacted with production transalkylation reaction zone effluent in transalkylation reaction zone at transalkylation catalyst;
(c) make the transalkylation reaction zone effluent enter the product separation device to produce product stream and to comprise C
9 +The first flow containing hydrocarbons of hydrocarbon;
(d) make at least part of C of comprising
9 +The first flow containing hydrocarbons of hydrocarbon enters hydrocracking zone; And
(e) reclaim dimethylbenzene from product stream.
2. method according to claim 1, it is further comprising the steps of:
(a) hydrocarbon-containing feedstock is introduced the product separation device, wherein said product stream comprises hydrogen, hydrogen sulfide, ammonia and C
8-aromatic hydrocarbon;
(b) making at least part of product stream enter the first fractionation zone comprises the flow containing hydrocarbons of benzene and toluene and comprises C with production
8 +The flow containing hydrocarbons of aromatic hydrocarbon;
(c) make at least part of C of comprising
8 +The flow containing hydrocarbons of aromatic hydrocarbon enters the after-fractionating district and is rich in the hydrocarbon stream of dimethylbenzene and comprises C with production
9 +The second flow containing hydrocarbons of hydrocarbon; And
(d) with at least part of C that comprises
9 +The second flow containing hydrocarbons of hydrocarbon and at least part of flow containing hydrocarbons that comprises benzene and toluene are introduced transalkylation reaction zone.
3. method according to claim 2, it is further comprising the steps of: processed hydrocarbon-containing feedstock before hydrocarbon-containing feedstock is introduced the product separation device in denitrogenation and desulfurization zone.
4. according to claim 2 or 3 described methods, wherein said hydrocarbon-containing feedstock comprises light cycle oil.
5. according to claim 2 or 3 described methods, the boiling point of wherein said hydrocarbon-containing feedstock is 149 ℃-399 ℃ and comprises at least 50 volume % aromatic substance.
6. method according to claim 1, it also comprises makes the product stream fractionation comprise the 3rd flow containing hydrocarbons of benzene and toluene and comprise C obtaining
9 +The 4th flow containing hydrocarbons of hydrocarbon, wherein said the third and fourth flow containing hydrocarbons reacts in transalkylation reaction zone.
7. according to claim 1,2 or 3 described methods, wherein said product separation device is that 149 ℃-288 ℃ and gauge pressure are to operate under the 3.5MPa-17.3Mpa in temperature.
8. according to claim 1,2 or 3 described methods, wherein said transalkylation reaction zone operates comprising under the following condition: temperature is that 200 ℃-525 ℃ and liquid hourly space velocity are 0.2hr
-1-10hr
-1
9. according to claim 1,2 or 3 described methods, wherein said hydrocracking zone operates comprising under the following condition: temperature is 232 ℃-468 ℃, and gauge pressure is 3.5MPa-20.8MPa, and liquid hourly space velocity is 0.1hr
-1-30hr
-1, and the hydrogen cycle rate is 337 standard m
3/ m
3-4200 standard m
3/ m
3
10. method according to claim 3, wherein said denitrogenation and desulfurization zone operate comprising under the following condition: temperature is 204 ℃-482 ℃, and gauge pressure is that 3.5MPa-17.3MPa and liquid hourly space velocity are 0.1hr
-1-10hr
-1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2007/072955 WO2009008876A1 (en) | 2007-07-06 | 2007-07-06 | Process for xylene production |
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| Publication Number | Publication Date |
|---|---|
| CN101730673A CN101730673A (en) | 2010-06-09 |
| CN101730673B true CN101730673B (en) | 2013-05-01 |
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|---|---|
| JP (1) | JP5351152B2 (en) |
| KR (1) | KR101392097B1 (en) |
| CN (1) | CN101730673B (en) |
| WO (1) | WO2009008876A1 (en) |
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| EP2644584B1 (en) * | 2010-11-25 | 2018-08-01 | SK Innovation Co., Ltd. | Method for producing high-added-value aromatic products and olefinic products from an aromatic-compound-containing oil fraction |
| JP5759263B2 (en) * | 2011-05-24 | 2015-08-05 | Ｊｘ日鉱日石エネルギー株式会社 | Monocyclic aromatic hydrocarbon production method |
| JP5759262B2 (en) * | 2011-05-24 | 2015-08-05 | Ｊｘ日鉱日石エネルギー株式会社 | Method for producing xylene |
| KR101545073B1 (en) | 2011-05-24 | 2015-08-17 | 제이엑스 닛코닛세키에너지주식회사 | Method for producing monocyclic aromatic hydrocarbon and plant for producing monocyclic aromatic hydrocarbon |
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| US5763720A (en) * | 1995-02-10 | 1998-06-09 | Mobil Oil Corporation | Transalkylation process for producing aromatic product using a treated zeolite catalyst |
| US6294080B1 (en) * | 1999-10-21 | 2001-09-25 | Uop Llc | Hydrocracking process product recovery method |
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| KR20100040309A (en) | 2010-04-19 |
| JP5351152B2 (en) | 2013-11-27 |
| WO2009008876A1 (en) | 2009-01-15 |
| JP2010532752A (en) | 2010-10-14 |
| CN101730673A (en) | 2010-06-09 |
| KR101392097B1 (en) | 2014-05-07 |
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