CN1095818C - Process for separating p-xylene with hydrophobic silicic zeolite by selective adsorption - Google Patents
Process for separating p-xylene with hydrophobic silicic zeolite by selective adsorption Download PDFInfo
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Abstract
The present invention discloses a method for selecting, adsorbing and separating paraxylene. The present invention uses an MFI-type molecular sieve adsorbing agent of hydrophobic silicalite-1 and a desorbent of which the desorbing strength coefficient is between 1.00 and the adsorbing and separating coefficient of the ethyl benzene of paraxylene. When the method of the present invention is used for selecting, adsorbing and separating C-8 aromatics isomers, particularly the paraxylene in the C-8 aromatics isomers containing the ethyl benzene under a liquid phase condition, the high-purity paraxylene can be directly obtained by adsorption and desorption. The adsorbing agent used by the present invention does not have to control the water content and can be regenerated.
Description
The present invention relates to a kind of method of from contain p-Xylol and at least a other C8 aronmatic mixture of isomers, selecting the fractionation by adsorption p-Xylol, particularly a kind of method of selecting the fractionation by adsorption p-Xylol with hydrophobic silicalite.
Dimethylbenzene and isomer thereof all are important chemical material, and wherein p-Xylol is used to produce vibrin.Along with the development of polyester industrial, demand constantly increases.When p-Xylol was used as polyester raw material, very high to its purity requirement, particularly the content of ethylbenzene impurity was low as far as possible, because the oxidation products of ethylbenzene is a phenylformic acid, and phenylformic acid is the chain terminator in the production of polyester polymerization process.Therefore, people are making great efforts the purer p-Xylol of preparation always.The method of separating paraxylene mainly contains cryogenic crystallization method, Separation by Complexation method and adsorption method of separation from xylol.At present, the method that the whole world extensively adopts is the adsorption method of separation of UOP (UOP), and as US 5,849,981, the used sorbent material of this patent is BaX or KBaX molecular sieve, belongs to faujusite (FAU) type.This sorbent material is the hydrophilic sorbent material, must dewater (before the full scale plant driving through the activation of strictness before use, generally to dewater) with about one month time activation, with the water content that guarantees sorbent material between 3%-6.5%, and, in use also must be constantly to the system water filling to keep the optimum moisture content of sorbent material, could guarantee the optimal adsorption separating effect of sorbent material like this.Crossing low, too high water content all can influence the separation performance of sorbent material.Find also that in industrial application suction is excessive if careless manipulation causes sorbent material, sorbent material is inactivation thoroughly.Because this sorbent material can not be regenerated, in case inactivation, the sorbent material that can only more renew.
The another kind of sorbent material that is used for the p-Xylol fractionation by adsorption is ZSM-5 molecular sieve or the ZSM-5 molecular sieve that has exchanged metallic cation, all belongs to MFI type molecular sieve.US 4,453, and 029 discloses and a kind ofly makes the method that sorbent material is selected fractionation by adsorption aromatic hydrocarbons with Cs-ZSM-5, can be with C with this sorbent material
8The arene isomer mixture is divided into two groups: one group is p-Xylol and ethylbenzene; Another group is o-Xylol and m-xylene, and the shortcoming of this patent is not relate to p-Xylol and ethylbenzene separation method.US 4,705,909 disclose a kind of silica alumina ratio one greater than 50 MFI type ZSM-5 adsorbent of molecular sieve, this sorbent material is with after excessive p-Xylol contacts, water or the water that contains low quantity of surfactant are made strippant with the p-Xylol desorption, be characterized in using water as strippant, its shortcoming is the separation that does not also relate to ethylbenzene in the p-Xylol.It is strippant with ZSM-5 type hydrophobic silicalite (being MFI type hydrophobic silicalite or Silicalite-1) for sorbent material, with the water vapor that Chinese patent CN1136549A (patent No. is ZL95112773.X) discloses a kind of, the fractionation by adsorption xylol can make m-xylene under gas phase condition, and the disclosed technological process of this patent application has realized industrialization.
The contriver is surprised to find that: with the disclosed ZSM-5 type hydrophobic Silicone Zeolite Molecular Sieve of Chinese patent CN1105906A (patent No. is ZL94112035.X) (being MFI type hydrophobic silicalite or Silicalite-1) sorbent material, the absorption to p-Xylol under liquid-phase condition is very strong; A little less than the absorption to ethylbenzene; Absorption to o-Xylol is very weak; M-xylene is adsorbed hardly.The contriver also finds: when making sorbent material, strippant can be selected within a large range with ZSM-5 type hydrophobic silicalite (Silicalite-1), and, by selecting suitable strippant, ethylbenzene is separated with p-Xylol.
The object of the invention is to provide a kind of and makes the method that sorbent material liquid phase from mixed C 8 aromatics is selected the fractionation by adsorption p-Xylol with ZSM-5 type hydrophobic Silicone Zeolite Molecular Sieve (Silicalite-1).This method is sorbent used need not controlled water-content and can regenerate.
It is a kind of from containing the C of ethylbenzene and p-Xylol at least that another object of the present invention is to provide
8Select the method for fractionation by adsorption p-Xylol in the aromatic hydrocarbons mixture, can ethylbenzene be separated with p-Xylol by desorption, thereby avoided fractionation by adsorption ethylbenzene and p-Xylol rectifying separation step afterwards with this method.
To achieve the above object of the invention, the present invention adopts following technical scheme: the process of fractionation by adsorption p-Xylol comprises the steps: from contain p-Xylol and at least a other C8 aronmatic mixture of isomers
(1) under the liquid phase adsorption condition, stock liquid contacts with ZSM-5 type hydrophobic Silicone Zeolite Molecular Sieve sorbent material, and p-Xylol is adsorbed agent and preferentially selects absorption;
(2) according to the desorption specific strength of strippant 1.00 and p-Xylol to the principle between the ethylbenzene fractionation by adsorption coefficient, from following strippant: benzene, single substituted alkyl benzene, to two substituted alkyl benzene, contain the single-substituted of O, S, P, halogen heteroatom group and contain O, S, P, halogen heteroatom group to choosing one or more the disubstituted benzenes, sorbent material with strippant fed after stock liquid contacts adsorbent bed or feeds adsorbent bed with the stock liquid that will contain strippant before stock liquid contacts at sorbent material;
(3) from the molecular sieve bed, be rich in behind the desorption in the liquid stream of p-Xylol and reclaim p-Xylol.
The ZSM-5 type hydrophobic silicalite (Silicalite-1) that the present invention adopts belongs to MFI type (MFI type zeolite molecular sieve comprises ZSM-5 and ZSM-5 hydrophobic type silicon zeolite), be that the sorbent material effect is better with binderless MFI type hydrophobic silicalite (binder free Silicalite-1) especially wherein, feature of this sorbent material and preparation method thereof is seen Chinese patent CN1105906A.This sorbent material has very high water, thermostability, anti-strong acid and weakly alkaline chemical etching.Because be substantially free of aluminium in the framework of molecular sieve, hydrophobicity is high, water regain is very little, and the surface that the moisture content that sucks is distributed in molecular sieve do not enter in the micropore of molecular sieve, thereby does not influence its absorption usefulness, need not control the water-content of sorbent material before the use.In addition, if because careless manipulation makes the adsorbent of molecular sieve poisoning and deactivation, only need simple calcination activation can make sorbent material recover active fully, the activating and regenerating condition was: at 300-800 ℃ of following roasting 1-5 hour.Simultaneously, because the main aperture road of this sorbent molecule sieve is ten oxygen annulus, its duct size is selected the shape separate effect to m-xylene and o-Xylol, to o-Xylol absorption seldom, m-xylene is hardly by the silicon zeolite adsorption, the p-Xylol that can enter in the molecular sieve hole then can be realized separating by selecting suitable strippant with the affinity interaction power of molecular sieve with ethylbenzene according to them.The strong and weak order of their absorption is decided by the size of fractionation by adsorption factor beta value.Separated component p-Xylol is to other each component (C
8) the fractionation by adsorption coefficient be defined as follows:
The β value shows between two components and can separate greater than 1, shows that separating effect is good more between two components greatly more.On the contrary, if the β value is too little,, show that then two components can not separate as less than 1.
The isolating purpose product of desire p-Xylol is to the desorption specific strength β of strippant
P-x/ D is defined as follows:
β
P-x/ D has characterized the intensity of molecular sieve adsorption p-Xylol and the ratio of adsorption-desorption agent intensity.β
P-x/ D is too small, as less than 1, shows that the adsorptive power of strippant on molecular sieve is stronger than separated component p-Xylol, like this after feeding strippant with under purpose product p-Xylol and the while desorb of other component; On the contrary, if β
P-x/ D is too big, as greater than 10, then will get off separated component desorb, need expend a large amount of strippants, is very uneconomic in actual applications.
A good strippant should possess following condition, and strippant does not react with stock liquid, under the adsorption desorption condition, and stable in properties; The each component boiling-point difference should be greater than 5 ℃ in its boiling point and the stock liquid; And the isolating purpose product of desire of the present invention p-Xylol is to the desorption specific strength β of strippant
P-x/ D value size should 1.00 with p-Xylol to inferior strong adsorbent component (ethylbenzene) fractionation by adsorption factor beta
P-xBetween/the eb, can guarantee like this desorption stage at first with the ethylbenzene desorption, desorption p-Xylol more afterwards, thus directly realize separating of ethylbenzene and p-Xylol by absorption, desorption process, avoid the rectifying separation of ethylbenzene and p-Xylol behind the desorption, saved investment and production cost.
The used strippant of the present invention comprises following four compounds: benzene, single substituted alkyl benzene, to two substituted alkyl benzene and heteroatoms substituted benzene.
In the present invention, benzene is a good strippant.The substituting group carbochain of single substituted alkyl benzene can be 1-12 carbon atom (not comprising ethylbenzene).Be methylbenzene, n-propylbenzene, n-butylbenzene, n-amylbenzene, n-heptylphenyl, n-nonyl benzene and dodecylbenzene preferably.Take all factors into consideration, toluene is most preferred sorbent material.Simultaneously, the mixture of two or more formations in the above-claimed cpd also can be used as strippant and uses, and according to practical situation, strippant also can be with the dilution of inertia component, as 1.
Another kind of strippant is contraposition two substituted alkyl benzene, two substituting group carbochain length of contraposition can be any, but be advisable with short carbochain, as carbonatoms is 2-5, preferable contraposition two substituted alkyl benzene are p-diethylbenzenes and to methyl-propyl benzene, best contraposition two substituted alkyl benzene are p-diethylbenzenes, equally, the mixture that is made of this class strippant compound or also can be used as strippant with mixture that single substituted alkyl benzene class strippant constitutes, strippant also can dilute with the inertia component.
In the present invention, contain and be halogeno-benzene in the single-substituted strippant of O, S, P, halogen heteroatom group preferably, best strippant is a mono chloro benzene; Contain O, S, P, halogen heteroatom group in the disubstituted benzenes strippant preferably for to phenyl-dihalide, best strippant is a santochlor.
The present invention requires not harsh to absorption, desorption conditions, as long as guarantee that absorption and desorption process are liquid phase.Adsorption temp is generally 20-300 ℃, and pressure is enough to make it to maintain liquid phase to get final product, generally change in about 30 atmospheric scopes at normal pressure.Desorption temperature is the same with adsorption temp and pressure range with pressure range.
The pattern of selection fractionation by adsorption p-Xylol of the present invention can be intermittently also can be successive, its process is achieved like this, with sorbent material with contain the mixed C of p-Xylol
8The aromatic hydrocarbons contact, wherein p-Xylol and ethylbenzene (if any) are preferred absorption; Meanwhile or subsequently (if periodical operation), strippant feeds adsorbent bed, ethylbenzene (if any) desorb that at first will be enriched on the molecular sieve is got off, and the p-Xylol desorb is got off afterwards again, and reclaim p-Xylol from the liquid stream that is rich in p-Xylol.For example, sorbent material can be contained in the fixed bed and the C that contains p-Xylol
8The aromatic hydrocarbons contact contacts with strippant subsequently again, perhaps sorbent material is contained in the moving-bed, and it is contacted in a continuous manner with the stock liquid that contains strippant.It also can be mimic really that moving-bed can adopt, liquid stream with in the same way or reverse mode contact.In fixed adsorption bed, the feeding of strippant can be semi-continuous, for example, can operate in the mode of Pulse Chromatographic, sorbent material also can be contained in one or more adsorption beds, and when stock liquid contacted with an adsorption bed, strippant was by other each adsorption bed desorb.Under certain conditions, before strippant being fed sorbent material desorb target product p-Xylol, can be with a kind of inertia component (it is very weak not to be adsorbed agent absorption or absorption) with C
8The most weak component of absorption purges out in the aromatic hydrocarbons mixture.Because therefore moving-bed or simulation moving-bedly have a very high separating effect is a kind of preferred clastotype.
Under the liquid phase adsorption condition, the used sorbent material of the present invention is bigger to the absorption and the ethylbenzene adsorption strength difference of p-Xylol, its relative fractionation by adsorption coefficient difference is bigger, when selecting strippant by method of the present invention, strippant can be selected within a large range, this to later industrial applications process choose effective, be easy to get, strippant particularly advantageous that price is low.And, select fractionation by adsorption C8 aronmatic isomer particularly to contain p-Xylol in the C8 aronmatic isomer of ethylbenzene with method of the present invention, can directly obtain the high purity p-Xylol by absorption, desorption.The used sorbent material of the present invention need not controlled water-content and can regenerate.
Further specify the present invention below in conjunction with embodiment, but do not limit to its scope.
Embodiment 1
This test is sorbent used to be the Industrial products that do not have stick hydrophobic silicalite (Silicalite-1) by the ZSM-5 type that patented technology (CN1105906A) is produced.Sieve is got 10-20 purpose particle during use, 550 ℃ of activation two hours, after absorption feed liquid (solvent and solute weight ratio is 1.2) is mixed, transfer in the closed reaction kettle, and 25 ℃ of following absorption reactions two hours, vibration a little in case of necessity.With the composition of feed liquid before and after the gas chromatographic analysis reaction, with 1,3, the 5-trimethylbenzene is interior mark, and the variable quantity according to each component before and after the absorption calculates the fractionation by adsorption coefficient.Experimental result sees Table 1.
Table 1
| Adsorption liquid is formed (weight ratio) | The fractionation by adsorption coefficient | |||
| β p-x/eb | β p-x/p-x | β p-x/m-x | β p-x/o-x | |
| p-x+eb(1∶1) | 9.26 | 1.00 | - | - |
| p-x+eb+o-x(1∶1∶2) | 8.83 | 1.00 | - | 15.23 |
| p-x+eb+m-x+o-x(1∶1∶1∶1) | 7.23 | 1.00 | Do not adsorb | 17.80 |
Embodiment 2
This test is sorbent used to be the Industrial products that do not have stick hydrophobic silicalite (Silicalite-1) by the ZSM-5 type that patented technology (CN1105906A) is produced, sieve is got 10-20 purpose particle during use, 550 ℃ of activation two hours, after the absorption feed liquid that contains strippant (abbreviating D as) (solvent and solute weight ratio is 1.3) is mixed, transfer in the closed reaction kettle, 25 ℃ of following absorption reactions two hours, vibration a little in case of necessity.With the composition of feed liquid before and after the gas chromatographic analysis reaction, with 1,3, the 5-trimethylbenzene is interior mark, and the variable quantity according to each component before and after the absorption calculates the fractionation by adsorption coefficient.Experimental result sees Table 2.
Table 2
| Strippant | The absorption feed liquid is formed (weight ratio) | The fractionation by adsorption coefficient | The desorption specific strength | ||
| β p-x/eb | β p-x/p-x | β p-x/o-x | β p-x/D | ||
| Benzene | p-x+eb+D(1∶1∶1) | 9.53 | 1.00 | - | 3.10 |
| Benzene | p-x+eb+o-x+D(1∶1∶1∶1) | 11.49 | 1.00 | 28.80 | 3.25 |
Embodiment 3
Experiment condition is the used strippant and the composition difference of absorption feed liquid with embodiment 2, experimental result such as table 3.
Table 3
| Strippant | The absorption feed liquid is formed (weight ratio) | The fractionation by adsorption coefficient | The desorption specific strength | ||
| β p-x/eb | β p-x/p-x | β p-x/o-x | β p-x/D | ||
| Toluene | p-x+eb+D(3∶3∶2) | 9.97 | 1.00 | - | 7.51 |
| Toluene | p-x+eb+ox+D(1∶1∶1∶1) | 11.21 | 1.00 | 30.87 | 7.41 |
| N-butyl benzene | p-x+eb+D(3.5∶3.5∶1) | 5.23 | 1.00 | - | 1.80 |
Embodiment 4
Experiment condition is with embodiment 2, and strippant is a p-diethylbenzene, and it is p-x that the absorption feed liquid is formed: eb: ox: D=1: 1: 1: 1, p-Xylol to the separation factor of strippant and other each component was: β
P-x/eb=9.46, β
P-x/D=3.51, β
P-x/o-x=25.30.
Embodiment 5
Experiment condition is with embodiment 2, and it is different with the composition of p-Diethylbenzene, absorption feed liquid that just desorb is respectively mono chloro benzene, and experimental result is listed in table 4.
Table 4
| Strippant | The absorption feed liquid is formed (weight ratio) | The fractionation by adsorption coefficient | The desorption specific strength | ||
| β p-x/eb | β p-x/p-x | β p-x/o-x | β p-x/D | ||
| Mono chloro benzene | p-x+eb+D(1∶1∶2) | 20.84 | 1.00 | - | 3.74 |
| Santochlor | p-x+eb+ox+D(1∶1∶1∶1) | 9.86 | 1.00 | 73.85 | 2.40 |
| Santochlor | p-x+eb+D(1∶1∶1) | 6.73 | 1.00 | - | 2.23 |
Embodiment 6
Used sorbent material is the Industrial products that do not have stick hydrophobic silicalite (Silicalite-1) by the ZSM-5 type that patented technology (CN1105906A) is produced, the water content difference of sorbent material, and other condition is with embodiment 1, and test-results sees Table 5.
Table 5
| Water content (weight %) | The composition (weight ratio) of absorption feed liquid | The fractionation by adsorption coefficient | ||
| β p-x/eb | β p-x/p-x | β p-x/o-x | ||
| 1.21 | p-x+eb(1∶1) | 9.36 | 1.00 | - |
| 2.08 | p-x+eb(1∶1) | 8.54 | 1.00 | - |
| 3.65 | p-x+eb+ox(1∶1∶2) | 9.56 | 1.00 | 16.34 |
Embodiment 7
The used sorbent material of this test all passes through activating and regenerating, is the number of times difference of activating and regenerating, and other condition is with embodiment 1.The activating and regenerating condition was: 550 ℃ of following roastings 2 hours.Test-results such as table 6.
Table 6
| Sorbent material activation number of times | The composition (weight ratio) of absorption feed liquid | The fractionation by adsorption coefficient | ||
| β p-x/eb | β p-x/p-x | β p-x/o-x | ||
| 5 | p-x+eb(1∶1) | 8.58 | 1.00 | - |
| 30 | p-x+eb+ox(1∶1∶2) | 8.78 | 1.00 | 17.23 |
| 100 | p-x+eb+ox(1∶1∶2) | 9.44 | 1.00 | 17.66 |
Claims (13)
1. the method for fractionation by adsorption p-Xylol comprises the steps: from contain p-Xylol and at least a other C8 aronmatic mixture of isomers
(1) under the liquid phase adsorption condition, stock liquid is that the Silicalite-1 sorbent material contacts with MFI type hydrophobic Silicone Zeolite Molecular Sieve, and p-Xylol is adsorbed agent and preferentially selects absorption;
(2) according to the desorption specific strength of strippant 1.00 and p-Xylol to the principle between the ethylbenzene fractionation by adsorption coefficient, from following strippant: benzene, single substituted alkyl benzene, to two substituted alkyl benzene, contain the single-substituted of O, S, P, halogen heteroatom group and contain O, S, P, halogen heteroatom group to choosing one or more the disubstituted benzenes, sorbent material with strippant fed after stock liquid contacts adsorbent bed or feeds adsorbent bed with the stock liquid that will contain strippant before stock liquid contacts at sorbent material;
(3) from the molecular sieve bed, be rich in behind the desorption in the liquid stream of p-Xylol and reclaim p-Xylol.
2. the method for fractionation by adsorption p-Xylol according to claim 1 is characterized in that described sorbent material is that binderless MFI type hydrophobic Silicone Zeolite Molecular Sieve is a binder free Silicalite-1 sorbent material.
3. the method for fractionation by adsorption p-Xylol according to claim 1 is characterized in that described stock liquid is for containing the C8 aronmatic mixture of isomers of p-Xylol and ethylbenzene at least.
4. the method for fractionation by adsorption p-Xylol according to claim 1 is characterized in that described stock liquid is the C8 aronmatic mixture of isomers that is substantially free of ethylbenzene
5. according to the method for each described fractionation by adsorption p-Xylol of claim 1～4, it is characterized in that described strippant is a benzene.
6. according to the method for each described fractionation by adsorption p-Xylol of claim 1～4, it is characterized in that described strippant is single C of replacement
1～C
12Alkylbenzene does not wherein comprise ethylbenzene.
7. the method for fractionation by adsorption p-Xylol according to claim 6 is characterized in that described strippant is a toluene.
8. according to the method for each described fractionation by adsorption p-Xylol of claim 1～4, it is characterized in that described strippant is for replacing C to two
2～C
5Alkylbenzene.
9. the method for fractionation by adsorption p-Xylol according to claim 8 is characterized in that described strippant is a p-diethylbenzene.
10. according to the method for each described fractionation by adsorption p-Xylol of claim 1～4, it is characterized in that described strippant is contain O, S, P, halogen heteroatom group single-substituted.
11. the method for fractionation by adsorption p-Xylol according to claim 10 is characterized in that described strippant is a chlorobenzene.
12. according to the method for each described fractionation by adsorption p-Xylol of claim 1～4, it is characterized in that described strippant be contain O, S, P, halogen heteroatom group to disubstituted benzenes.
13. the method for fractionation by adsorption p-Xylol according to claim 12 is characterized in that described strippant is a santochlor.
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| CN1095818C true CN1095818C (en) | 2002-12-11 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1319912C (en) * | 2005-08-18 | 2007-06-06 | 复旦大学 | Complex phase adsorption separating method on hydrophobic silicon zeolite for benzene di-substituted isomer |
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| CN106237652B (en) * | 2015-06-11 | 2019-09-20 | 上海复榆新材料科技有限公司 | Method is selectively adsorbing and separating using molecular sieve as adsorbent |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4705909A (en) * | 1986-02-27 | 1987-11-10 | Mobil Oil Corporation | Process for the separation of para-xylene |
| CN1124241A (en) * | 1993-08-23 | 1996-06-12 | 环球油品公司 | Improved adsorptive separation of metalxylene from aromatic hydrocarbons |
| CN1136549A (en) * | 1994-12-29 | 1996-11-27 | 中国石化金陵石油化工公司 | Method for separating m-xylene and ortho-xylene from mixed xylene and ethyl benzene |
-
1999
- 1999-07-17 CN CN99108761A patent/CN1095818C/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4705909A (en) * | 1986-02-27 | 1987-11-10 | Mobil Oil Corporation | Process for the separation of para-xylene |
| CN1124241A (en) * | 1993-08-23 | 1996-06-12 | 环球油品公司 | Improved adsorptive separation of metalxylene from aromatic hydrocarbons |
| CN1136549A (en) * | 1994-12-29 | 1996-11-27 | 中国石化金陵石油化工公司 | Method for separating m-xylene and ortho-xylene from mixed xylene and ethyl benzene |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1319912C (en) * | 2005-08-18 | 2007-06-06 | 复旦大学 | Complex phase adsorption separating method on hydrophobic silicon zeolite for benzene di-substituted isomer |
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