CN103121896A - Method for converting polycyclic aromatic hydrocarbons into monocyclic aromatic hydrocarbons - Google Patents
Method for converting polycyclic aromatic hydrocarbons into monocyclic aromatic hydrocarbons Download PDFInfo
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- CN103121896A CN103121896A CN2011103694716A CN201110369471A CN103121896A CN 103121896 A CN103121896 A CN 103121896A CN 2011103694716 A CN2011103694716 A CN 2011103694716A CN 201110369471 A CN201110369471 A CN 201110369471A CN 103121896 A CN103121896 A CN 103121896A
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Abstract
The invention relates to a method for converting polycyclic aromatic hydrocarbons into monocyclic aromatic hydrocarbons, mainly solving the problems in the prior art that the conversion level of polycyclic aromatic hydrocarbons is low, the monocyclic aromatic hydrocarbon yield and selectivity are low and the catalyst deactivation rate is high. The problems are better solved by adopting the technical scheme that polycyclic aromatic hydrocarbon mixtures and hydrogen are taken as the raw materials and are contacted with a catalyst in a fixed bend reactor to react under the conditions that the reaction temperature is 335-440 DEG C, the pressure is 4-7MPa, the weight hourly space velocity is 1-3hr<-1> and the hydrogen/hydrocarbon mole ratio is 4.0-8.0 to generate monocyclic aromatic hydrocarbon mixtures. The method can be used in the industrial production of converting heavy polycyclic aromatic hydrocarbons into monocyclic aromatic hydrocarbons.
Description
Technical field
The present invention relates to a kind of method that polycyclic aromatic hydrocarbons is converted into mononuclear aromatics.
Background technology
In recent years, continuous intensification along with oil product degree of heaviness in world petroleum resource, how under the prerequisite that satisfies the high standard environmental requirement, effectively utilize these heavy oil resources and satisfy and improve the daily life needs and become an important research topic.In heavy oil product, the annual production of heavy aromatics increases year by year, and except seldom a part is as organic solvent, major part is mixed in fuel and used, and no matter from environmental protection or economic angle, Heavy Aromatic Hydrocarbons is not all fully utilized effectively.The source of heavy aromatics mainly is present in the cracking process of catalytic reforming and hydrocarbon, can reach 70% as the content of the condensed ring naphthalene series aromatics of heavy in catalytic cracking light cycle oil (LCO).Utilize the industrial foundation organic raw material of these heavy aromatics exploitation high added values, as good selections beyond doubt such as benzene,toluene,xylenes (BTX).At present, domestic triphen production mainly utilizes straight-run spirit, petroleum naphtha to obtain through noble metal platinum reforming process and preparing ethylene by steam cracking technique, and because of starving, the output of benzene and its derivative is restricted to a great extent.China's light and textile industries' development in recent years is very fast, the annual downstream derivative product that needs a large amount of import benzene, and also the import volume growth is very fast, seeks the aromatic hydrocarbons yield-increasing technology very urgent.
Nippon Oil(Nippon Mitsubishi Oil) report on January 21st, 2010 will be developed the technical matters of producing aromatic hydrocarbon product with solar oil (LCO).Compare with the traditional technology of a large amount of consumption hydrogen, this new technology can be cut down production cost, is expected to realize commercially producing.
USP4,341,622 disclose a kind of method of utilizing the heavy reformate to produce BTX.The zeolite that the method adopts that restricted index is 1～12, silica/alumina molar ratio (silica alumina ratio) is 12 or more, hang down acid activity is catalyzer, reformate is reacted under the condition of 427～540 ℃, then the resultant fractionation by distillation is obtained benzene, toluene and dimethylbenzene.Described catalyzer contains the VIII family precious metal of hydro-dealkylation function, preferred platinum, and the silica alumina ratio of zeolite used is preferably greater than 200, and more preferably greater than 500, preferred zeolite is ZSM-5.Select the zeolite of high silica alumina ratio for reducing zeolite acidity, keep as far as possible dimethylbenzene and be not converted in reaction.
US2007062848A1 disclose a kind of first will carry out again after the polycyclic aromatic hydrocarbons fractional saturation selective opening and take off the method that alkyl obtains light aromatics.The method can satisfy in feed stream polycyclic aromatic hydrocarbon content more than 20wt%, and the saturation stage temperature is at 300～500 ℃, pressure 2～10MPa; The open loop phase temperature is at 200～600 ℃, pressure 1～12MPa.Because the two-stage catalytic agent is contained in same reactor, thus require logistics need to guarantee that certain residence time could obtain transformation efficiency preferably, so air speed is lower.
CN1117404A discloses a kind of from containing C
9 +The hydrocarbon feed of aromatic hydrocarbons is produced the catalyzer of benzene, toluene and dimethylbenzene, and this catalyzer is in the γ of the ZSM-5 zeolite of 30～70 % by weight (take carrier as benchmark) and 30～70 heavy %-or η-Al
2O
3Be carrier, the palladium of the rhenium of load 0.1～0.5 heavy %, the tin of 0.1～0.5 heavy %, 0.05～0.3 heavy % platinum or 0.2～0.8 heavy % forms.At 350～450 ℃, 0.5～3.5MPa, weight space velocity 1～5 o'clock
-1, hydrogen/hydrocarbon (volume ratio) 500～1200 operational condition under, this catalyzer has higher catalytic activity and stability, and lower hydrogen consumption.
CN1472181A discloses a kind of heavy aromatics lightening catalyst, comprise VIII family's metal and the complex carrier of 0.01～2.0 heavy %, described complex carrier comprises the ZSM-5 zeolite of 30～70 heavy %, the mordenite of 5～20 heavy % and the aluminum oxide of 10～65 % by weight.This catalyzer is used for heavy aromatic hydrocarbon light, can improve C
9 +The productive rate of aromatics conversion rate and benzene and dimethylbenzene, and reduce carbon distribution.
Summary of the invention
Technical problem to be solved by this invention is that to be converted into mononuclear aromatics when reaction polycyclic aromatic hydrocarbons depth of conversion low in order to overcome the heavy polycyclic aromatic hydrocarbons that exists in prior art, the mononuclear aromatics yield is low and selectivity is low, the problem that catalyst deactivation rate is fast provides a kind of new polycyclic aromatic hydrocarbons to be converted into the method for mononuclear aromatics.It is high that the method has a polycyclic aromatic hydrocarbons depth of conversion, and the mononuclear aromatics yield is high and selectivity is high, the advantage that catalyst deactivation rate is slow.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of polycyclic aromatic hydrocarbons is converted into list
The method of Polycyclic aromatic hydrocarbons is passed through fixed-bed reactor take Polycyclic Aromatic Hydrocarbon Mixture and hydrogen as raw material, at 335～440 ℃ of temperature of reaction, reaction pressure 4～7MPa, weight hourly space velocity degree 1～3hr
-1, hydrogen hydrocarbon mol ratio 4.0～8.0 condition under generate the mononuclear aromatics mixture with the catalyzer contact reacts, wherein catalyzer used comprises following component by weight percentage:
A) 34.5～60%FAU type zeolite and the mixture that is selected from least a molecular sieve in MOR, BEA, MFI or MCM-22;
B) 39.5～65% be selected from least a for binding agent in gama-alumina, η-aluminum oxide or pseudo-boehmite;
C) 0.05～0.9% at least a metal or its oxide compound that is selected from Pt, Pd or Ir.
In technique scheme, Polycyclic Aromatic Hydrocarbon Mixture is mainly naphthalene series compound; The mononuclear aromatics mixture comprises benzene, toluene, ethylbenzene, dimethylbenzene, C9 aromatic and C10 aromartic.
In technique scheme, FAU type zeolite and be selected from least a molecular sieve in MOR, BEA, MFI or MCM-22 and be the sodium weight content lower than 2% Hydrogen or ammonium type zeolite during used catalyst forms; In mixture by weight percentage the amount preferable range of FAU type zeolite be 50～90%, the amount preferable range that is selected from least a molecular sieve in MOR, BEA, MFI or MCM-22 is 10～50%.
The preparation method of used catalyst in the inventive method comprises the following steps:
1. with the FAU type zeolite of aequum and be selected from the mixture of at least a molecular sieve in MOR, BEA, MFI or MCM-22 and being selected from least a binding agent in gama-alumina, η-aluminum oxide, pseudo-boehmite and carrying out kneading, moulding, drying of aequum after, obtain support of the catalyst at 450～650 ℃ of roasting 0.5～24h;
2. the precursor solution that is selected from least a metal in Pt, Pd or Ir or its oxide compound of aequum is impregnated into 0.5～24h on support of the catalyst in 30～50 ℃, obtains finished catalyst at 300～450 ℃ of roasting 0.5～24h after drying.
In technique scheme, preferred version can add the extrusion aid that calculates 2～5% weight by the carrier butt, for example sesbania powder in the support of the catalyst preparation process; Can add at least a and water volume ratio acid solution of 1: 1～1: 5 that is selected from hydrochloric acid, nitric acid, acetic acid, tartrate, citric acid or oxalic acid by carrier butt calculating 3～6% weight is gelatinizing agent.
In technique scheme, the precursor solution preferred version of Pt metal used is Platinic chloride; The precursor solution preferred version of metal Pd is at least a in Palladous nitrate or Palladous chloride; The precursor solution preferred version of metal Ir is chloro-iridic acid.
Method provided by the invention is a kind of method that is converted into mononuclear aromatics for the heavy polycyclic aromatic hydrocarbons, and the method can be used for producing benzene, toluene and dimethylbenzene.
In the present invention due to type zeolite such as the FAU that has selected three-dimensional macropore, BEA as the catalyst acid center, be conducive to the acid site that the heavy arene macromole enters in the duct and carry out ring-opening reaction, product molecule after conversion can the passing hole channel rapid diffusion, thereby has delayed the deactivation rate of catalyzer; The precious metal element that has hydrogenating function by load is controlled its charge capacity at a zone of reasonableness, can effectively improve the degree of unsaturation of Polycyclic Aromatic Hydrocarbon Mixture raw material, helps the deep conversion polycyclic aromatic hydrocarbons; The rational proportion of catalyst acid center and metallic element takes off alkyl, transalkylation and light aromatic hydrocarbons aromatization generation with part during will making the hydrogenation open loop simultaneously, these reactions will keep original mononuclear aromatics component in feedstream as far as possible, so that the yield of mononuclear aromatics and selectivity maximize, obtained technique effect preferably.
The present invention uses overcritical fixed-bed reactor to carry out the reactivity worth investigation that polycyclic aromatic hydrocarbons is converted into mononuclear aromatics, 12 millimeters of reactor inside diameter Ф, 800 millimeters of length, stainless steel.Adopt electrically heated, temperature is controlled automatically.It is upholder that reactor bottom is filled 2～3 millimeters granulated glass spherees of Ф, catalyst filling 5 grams in reactor, and 2～3 millimeters granulated glass spherees of Ф are filled on top, are made for the use of raw material preheating and vaporization.The raw material Polycyclic Aromatic Hydrocarbon Mixture mixes with hydrogen, by beds, makes polycyclic aromatic hydrocarbons be converted into the mononuclear aromatics such as benzene,toluene,xylene from top to bottom.
Polycyclic Aromatic Hydrocarbon Mixture is the autogamy raw material, and experimental data is calculated as follows.
The present invention is further elaborated below by embodiment.
Embodiment
[embodiment 1]
Be 30g FAU type zeolite (being purchased Hydrogen), 10g BEA type zeolite (being purchased Hydrogen) and 60g γ-Al with butt
2O
3(industrial goods) add mixing tank to evenly, then add 3g sesbania powder, 1: 1 HNO of 5g volume ratio in mixture
3Solution and 40g deionized water grind and evenly make the dough that is suitable for extruding.It is extruded by mould, and shape is elongated cylindrical (diameter 1.7mm), after 120 ℃ of oven dry in 550 ℃ of roasting 4h, then it is cut into consistent size carrier granule (1.7 * 4.0mm), be designated as Z1.
The Platinic chloride wiring solution-forming is flooded carrier granule under 40 ℃, and the amount that contains Pt in steeping fluid is 0.1% of carrier butt weight, and dipping 8h at 450 ℃ of roasting 3h, makes finished catalyst A also after drying.
[embodiment 2～6]
Preparation method and process according to embodiment 1 provides in the process to Z1 carrier granule dipping, have prepared a series of finished catalysts by the kind that changes metal precursor in steeping fluid, see Table 1.
Table 1
| The catalyzer numbering | Carrier forms | Metal precursor | The metal impregnation amount |
| B | Z1 | Palladous nitrate | 0.1wt％Pd |
| C | Z1 | Chloro-iridic acid | 0.1wt％Ir |
| D | Z1 | Platinic chloride, Palladous nitrate | 0.032wt％Pt、0.068wt％Pd |
| E | Z1 | Platinic chloride, chloro-iridic acid | 0.05wt％Pt、0.05wt％Ir |
| F | Z1 | Palladous nitrate, chloro-iridic acid | 0.032wt％Ir、0.068wt％Pd |
[embodiment 7～12]
Preparation method and process according to embodiment 1 provides in the process to Z1 carrier granule dipping, have prepared a series of finished catalysts by the pickup that changes metal, see Table 2.
Table 2
| The catalyzer numbering | Carrier forms | Metal precursor | The metal impregnation amount |
| G | Z1 | Platinic chloride | 0.2wt％Pt |
| H | Z1 | Chloro-iridic acid | 0.2wt％Ir |
| I | Z1 | Palladous nitrate | 0.2wt％Pd |
| J | Z1 | Platinic chloride, Palladous nitrate | 0.09wt％Pt、0.06wt％Pd |
| K | Z1 | Palladous nitrate, chloro-iridic acid | 0.09wt％Ir、0.06wt％Pd |
| L | Z1 | Platinic chloride, chloro-iridic acid | 0.07wt％Pt、0.07wt％Ir |
[embodiment 13～20]
Preparation method and process according to embodiment 1 provides by changing the contamination of metal precursor in carrier composition and steeping fluid, have prepared a series of finished catalysts, see Table 3.
Table 3
Catalyst A～the T that makes with embodiment 1～20 (highest response pressure 10MPa, use temperature are room temperature～600 ℃) on overcritical fixed-bed reactor investigates and Polycyclic Aromatic Hydrocarbon Mixture is converted into BTX (wherein B is benzene, T is toluene, and X is dimethylbenzene) etc. the ability of mononuclear aromatics.Table 4 forms for the Polycyclic Aromatic Hydrocarbon Mixture raw material.Catalyst loading 5g is at 370 ℃ of temperature of reaction, reaction pressure 6MPa, weight hourly space velocity degree 2.0hr
-1, contact with catalyzer under hydrogen/hydrocarbon mol ratio 5.0 conditions, product is reclaimed and component detects, conversion results is shown in Table 5.
Table 4 raw material forms
| Raw material forms | Non-aromatic | Benzene | Toluene | Ethylbenzene | Dimethylbenzene | Perhydronaphthalene | Naphthane | Naphthalene |
| Content (wt%) | 0.02 | 24.54 | 24.61 | 5 | 0.02 | 14.81 | 15.25 | 15.75 |
Table 5 polycyclic aromatic hydrocarbons conversion results
| The catalyzer numbering | Total conversion rate (wt%) | Mononuclear aromatics selectivity (wt%) | BTX selectivity (wt%) |
| A | 70.5 | 61.2 | 39.6 |
| B | 73.1 | 65.3 | 43.8 |
| C | 68.2 | 63.5 | 38.9 |
| D | 71.8 | 64.0 | 42.2 |
| E | 69.4 | 61.6 | 40.8 |
| F | 71.0 | 64.2 | 43.0 |
| G | 78.3 | 66.1 | 44.2 |
| H | 76.5 | 65.6 | 43.9 |
| I | 80.3 | 65.9 | 45.0 |
| J | 79.4 | 66.3 | 44.8 |
| K | 77.3 | 65.2 | 43.5 |
| L | 76.1 | 64.8 | 42.4 |
| M | 71.0 | 60.3 | 37.2 |
| N | 67.4 | 59.8 | 38.3 |
| O | 65.5 | 58.1 | 33.4 |
| P | 72.3 | 64.9 | 43.0 |
| Q | 67.2 | 59.1 | 36.6 |
| R | 78.9 | 66.3 | 43.2 |
| S | 80.3 | 65.4 | 42.8 |
| T | 72.1 | 60.2 | 39.5 |
[embodiment 21～26]
Catalyst A～the F that makes with embodiment 1～6 investigates the ability of the mononuclear aromatics such as BTX that Polycyclic Aromatic Hydrocarbon Mixture is converted on overcritical fixed-bed reactor.Catalyst loading 5g is at 400 ℃ of temperature of reaction, reaction pressure 6MPa, weight hourly space velocity degree 2.0hr
-1, contact with catalyzer under hydrogen/hydrocarbon mol ratio 5.0 conditions, product is reclaimed and component detects, conversion results is shown in Table 6.
Table 6 polycyclic aromatic hydrocarbons conversion results
| The catalyzer numbering | Total conversion rate (wt%) | Mononuclear aromatics selectivity (wt%) | BTX selectivity (wt%) |
| A | 79.7 | 70.6 | 46.5 |
| B | 80.1 | 73.0 | 51.6 |
| C | 75.6 | 72.6 | 46.3 |
| D | 77.6 | 71.3 | 50.2 |
| E | 77.3 | 69.2 | 47.1 |
| F | 80.7 | 72.5 | 50.0 |
[embodiment 27～32]
Catalyst A～the F that makes with embodiment 1～6 investigates the ability of the mononuclear aromatics such as BTX that Polycyclic Aromatic Hydrocarbon Mixture is converted on overcritical fixed-bed reactor.Catalyst loading 5g is at 370 ℃ of temperature of reaction, reaction pressure 5MPa, weight hourly space velocity degree 2.0hr
-1, contact with catalyzer under hydrogen/hydrocarbon mol ratio 5.0 conditions, product is reclaimed and component detects, conversion results is shown in Table 7.
Table 7 polycyclic aromatic hydrocarbons conversion results
| The catalyzer numbering | Total conversion rate (wt%) | Mononuclear aromatics selectivity (wt%) | BTX selectivity (wt%) |
| A | 68.3 | 60.5 | 38.3 |
| B | 71.0 | 64.4 | 42.2 |
| C | 66.1 | 62.1 | 37.5 |
| D | 69.3 | 63.7 | 41.6 |
| E | 67.0 | 62.3 | 39.4 |
| F | 69.4 | 63.0 | 42.2 |
[embodiment 33～38]
Catalyst A～the F that makes with embodiment 1～6 investigates the ability of the mononuclear aromatics such as BTX that Polycyclic Aromatic Hydrocarbon Mixture is converted on overcritical fixed-bed reactor.Catalyst loading 5g is at 370 ℃ of temperature of reaction, reaction pressure 6MPa, weight hourly space velocity degree 3.0hr
-1, contact with catalyzer under hydrogen/hydrocarbon mol ratio 5.0 conditions, product is reclaimed and component detects, conversion results is shown in Table 8.
Table 8 polycyclic aromatic hydrocarbons conversion results
| The catalyzer numbering | Total conversion rate (wt%) | Mononuclear aromatics selectivity (wt%) | BTX selectivity (wt%) |
| A | 67.1 | 62.9 | 40.2 |
| B | 70.0 | 66.8 | 44.6 |
| C | 65.2 | 64.5 | 39.4 |
| D | 68.2 | 65.7 | 43.1 |
| E | 66.3 | 64.2 | 41.5 |
| F | 68.1 | 65.7 | 44.0 |
[embodiment 39～44]
Catalyst A～the F that makes with embodiment 1～6 investigates the ability of the mononuclear aromatics such as BTX that Polycyclic Aromatic Hydrocarbon Mixture is converted on overcritical fixed-bed reactor.Catalyst loading 5g is at 370 ℃ of temperature of reaction, reaction pressure 6MPa, weight hourly space velocity degree 2.0hr
-1, contact with catalyzer under hydrogen/hydrocarbon mol ratio 7.0 conditions, product is reclaimed and component detects, conversion results is shown in Table 9.
Table 9 polycyclic aromatic hydrocarbons conversion results
| The catalyzer numbering | Total conversion rate (wt%) | Mononuclear aromatics selectivity (wt%) | BTX selectivity (wt%) |
| A | 70.9 | 61.8 | 39.9 |
| B | 74.0 | 65.7 | 44.5 |
| C | 68.9 | 63.9 | 39.2 |
| D | 72.3 | 64.7 | 42.7 |
| E | 69.9 | 62.0 | 41.4 |
| F | 71.5 | 65.5 | 44.0 |
[comparative example 1～6]
Catalyst A～the F that makes with embodiment 1～6 investigates the ability of the mononuclear aromatics such as BTX that Polycyclic Aromatic Hydrocarbon Mixture is converted on overcritical fixed-bed reactor.Catalyst loading 5g is at 370 ℃ of temperature of reaction, reaction pressure 5MPa, weight hourly space velocity degree 2.5hr
-1, contact with catalyzer under hydrogen/hydrocarbon mol ratio 6.0 conditions, product is reclaimed and component detects, conversion results is shown in Table 10.
Table 10 polycyclic aromatic hydrocarbons conversion results
| The catalyzer numbering | Total conversion rate (wt%) | Mononuclear aromatics selectivity (wt%) | BTX selectivity (wt%) |
| A | 69.3 | 63.1 | 40.8 |
| B | 70.4 | 66.0 | 45.2 |
| C | 65.9 | 65.1 | 40.2 |
| D | 67.1 | 64.8 | 44.1 |
| E | 67.7 | 62.6 | 41.3 |
| F | 70.0 | 65.9 | 44.4 |
Claims (5)
1. a polycyclic aromatic hydrocarbons is converted into the method for mononuclear aromatics, passes through fixed-bed reactor take Polycyclic Aromatic Hydrocarbon Mixture and hydrogen as raw material, at 335～440 ℃ of temperature of reaction, reaction pressure 4～7MPa, weight hourly space velocity degree 1～3hr
-1, hydrogen/hydrocarbon mol ratio 4.0～8.0 condition under generate the mononuclear aromatics mixture with the catalyzer contact reacts, wherein catalyzer used comprises following component by weight percentage:
A) 34.5～60%FAU type zeolite and the mixture that is selected from least a molecular sieve in MOR, BEA, MFI or MCM-22;
B) 39.5～65% be selected from least a for binding agent in gama-alumina, η-aluminum oxide or pseudo-boehmite;
C) 0.05～0.9% at least a metal or its oxide compound that is selected from Pt, Pd or Ir.
2. polycyclic aromatic hydrocarbons according to claim 1 is converted into the method for mononuclear aromatics, it is characterized in that described Polycyclic Aromatic Hydrocarbon Mixture is mainly naphthalene series compound.
3. polycyclic aromatic hydrocarbons according to claim 1 is converted into the method for mononuclear aromatics, it is characterized in that described mononuclear aromatics mixture comprises benzene, toluene, ethylbenzene, dimethylbenzene, C9 aromatic and C10 aromartic.
4. polycyclic aromatic hydrocarbons according to claim 1 is converted into the method for mononuclear aromatics, it is characterized in that FAU type zeolite and be selected from least a molecular sieve in MOR, BEA, MFI or MCM-22 being the sodium weight content lower than 2% Hydrogen or ammonium type zeolite.
5. polycyclic aromatic hydrocarbons according to claim 1 is converted into the method for mononuclear aromatics, it is characterized in that in mixture that the amount of FAU type zeolite is 50～90% by weight percentage, the amount that is selected from least a molecular sieve in MOR, BEA, MFI or MCM-22 is 10～50%.
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