CN101190868B - Separation utilization method for preparing ethene by-product C9+ fractioning by cracking - Google Patents
Separation utilization method for preparing ethene by-product C9+ fractioning by cracking Download PDFInfo
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Abstract
The invention relates to a method of separating and utilizing ethylene by product C9<+> distillate produced by cracking, and consists of the procedures: the C9<+> distillate is separated into ethylene distillate with rich benzene and distillate at the bottom of a rectifying tower by rectifying under reduced pressure; the distillate at the bottom of the rectifying tower is heated to 180 - 380DEG Cand rectified under normal pressure; cyclopentadiene distillate, methyl cyclopentadiene distillate, distillate with rich dicyclopentadiene, distillate with high content of indene and heavy end distillate are separated from the top of the rectifying tower to the bottom of the rectifying tower in turn. With the method, not only high quality petroleum resin is available, but cyclopentadiene and methyl cyclopentadiene can also be obtained at the same time.
Description
Technical field
The present invention is a kind of cracking ethylene preparation by product C
9 +Fraction separation is utilized method, specifically, is a kind of from described C
9 +Separation of produced petroleum resin raw material in the cut extracts the method for cyclopentadiene and methyl cyclopentadiene simultaneously.
Background technology
The C of cracking ethylene preparation device by-product
9 +Cut (is called for short cracking C
9 +Or cracking C
9) be to isolate C through extracting by petroleum naphtha or solar oil split product
5Cut, C
6～C
8Residue cut behind the cut (producing BTX through hydrogenation) accounts for 10%～20% of ethene ultimate production.Along with the raising year by year of China's ethylene production capacity, fully effectively utilize the by product cracking C in the ethylene production
9 +, comprehensively excavate their potential utility values, will become the important topic that the refining of petroleum industry faces.
Cracking C
9 +Form complexity, 150 various ingredients are arranged approximately, wherein unsaturated component is more.The difficulty that technologies such as present industrial employing distillation are separated these components is bigger, and treatment process commonly used is directly to produce the aromatic hydrocarbons petroleum resin with it.But cracking C
9 +In dicyclopentadiene and two methyl cyclopentadiene content higher, easily cause in the preparation process resin form and aspect to worsen and generate gelatinous mass.Therefore, with dicyclopentadiene and two methyl cyclopentadiene content greater than 2% cracking C
9 +The resin quality that direct polymerization is produced is relatively poor, can't satisfy customer requirements.
Dicyclopentadiene DCPD (C
10H
12) be the dimer of cyclopentadiene (CPD), depolymerization reaction at high temperature can take place generate cyclopentadiene.Its depolymerization reaction equation is as follows:
Above-mentioned reaction is reversible thermo-negative reaction, and the DCPD depolymerization generates CPD under high temperature (greater than 180 ℃), and the CPD dimerization generates DCPD under low temperature (less than 130 ℃).
Dicyclopentadiene and two methyl cyclopentadiene contain a plurality of unsaturated double-bonds, and chemical property is very active, can react with multiple compound, have wide industrial to use.Can be used for the production of ethylene-propylene rubber(EPR), unsaturated polyester, synthesizing petroleum resin, synthetic paint resin, resin glue, papermaking weighting agent resin, medicine and fuel, synthetic materials, synthetic perfume, organic chemistry intermediate.Cyclopentadiene and methyl cyclopentadiene that dicyclopentadiene and two methyl cyclopentadiene depolymerization generate also are the intermediates of synthetic resins, agricultural chemicals, medicine, spices etc.For cyclopentadiene and methyl cyclopentadiene and dimer thereof, particularly highly purified cyclopentadiene and methyl cyclopentadiene not only market demand are very big, and cost an arm and a leg at present.If from cracking C
9 +In isolate highly purified cyclopentadiene and methyl cyclopentadiene, not only can solve and produce high quality C
9 +The raw materials quality problem of petroleum resin, but also can improve cracking C
9 +Utility value.Cracking C
9 +Mid-boiling point and cyclopentadiene and methyl cyclopentadiene are approaching and the active active ingredient of chemical property is a lot, therefore utilize cracking C
9 +Produce high-purity cyclopentadiene and methyl cyclopentadiene and dimeric report thereof seldom.
US6258989 and US6737557 have introduced the method about the pyrolysis gasoline comprehensive treating process, and at first the pyrolysis gasoline heating being made cyclopentadiene dimerization wherein is dicyclopentadiene, adopts the method for rectifying that this material is cut into C then
5～C
9And C
10 +The cut section, C
5～C
9Cut is produced benzene, toluene and dimethylbenzene products such as (BTX), C through hydrogenation
10 +The further rectifying separation of cut section goes out dicyclopentadiene and oil fuel.This method extracts the cut that is rich in dicyclopentadiene from pyrolysis gasoline, the content of dicyclopentadiene is about 83wt% in the example greater than 70wt% in this cut.
Liu Gongzhao etc. (Shenyang Institute of Chemical Technology journal, 2000,12:266～268) report adopts vapor-phase thermal cracking-rectification process from C
9 +By product in the petroleum resin production process gently dodges and separates the method for removing dicyclopentadiene in the oil.This method will gently be dodged oil and be heated to 180～340 ℃ in pyrolyzer, make the dicyclopentadiene cracking under comparatively suitable air speed.Then it is sent into rectifying tower, cat head is isolated the light constituent cyclopentadiene, and purity can reach more than 98%.Obtain removing the light sudden strain of a muscle oil that meets the solvent service requirements after the dicyclopentadiene at the bottom of the tower.Unsaturated active component content significantly reduces in the light sudden strain of a muscle oil, adopts aforesaid method can obtain result preferably.If directly with cracking C
9 +Be raw material, adopt aforesaid method separating ring pentadiene, a lot of with the approaching active ingredient of DCPD boiling point in the raw material, the reaction of polymerization and green coke can aggravation under the temperature of heating pyrolyze DCPD, will cause from cracking C
9 +Middle failure of extracting DCPD.
Summary of the invention
The purpose of this invention is to provide a kind of ethylene unit by product C
9 +Fraction separation is utilized method, and this method is when obtaining high-quality petroleum resin raw material, but higher cyclopentadiene and the methyl cyclopentadiene product of also production purity.
Cracking ethylene preparation by product C provided by the invention
9 +The method of the utilization of cut comprises the steps:
(1) with C
9 +Cut is divided into rich in styrene cut and tower bottom distillate with rectification under vacuum;
(2) after (1) step, described tower bottom distillate was heated to 180～380 ℃, carry out atmospheric distillation, at the bottom of tower, isolate cyclopentadiene cut, methyl cyclopentadiene cut, the cut that is rich in dicyclopentadiene, higher cut and the heavy ends of indenes content successively by the atmospheric distillation cat head.
The present invention adopts rectification under vacuum-atmospheric distillation bonded method, from cracking C
9 +Isolate the high-purity cyclopentadiene and the methyl cyclopentadiene of high-quality petroleum resin raw material and high added value in the cut, further vacuum fractionation also can obtain aromatic solvent and tar.Thereby can make full use of cracking C
9 +The value of each component in the cut.
Description of drawings
Fig. 1 is the schematic flow sheet of the inventive method.
Embodiment
The present invention adopts rectification under vacuum separating and cracking C
9 +Vinylbenzene cut in the cut makes in its light constituent that concentrates on rectification under vacuum, and heavy constituent then contain more dicyclopentadiene and two methyl cyclopentadiene at the bottom of the tower.Component is heated to the decomposition temperature of dicyclopentadiene and two methyl cyclopentadienes and delivers to the atmospheric distillation tower after above at the bottom of the tower, cyclopentadiene that decomposites in the component at the bottom of the tower and methyl cyclopentadiene boiling point are lower, tell successively at top of tower and top side line, other higher component of boiling point is told from the middle and lower part side line of tower successively, heavy constituent at the bottom of the atmospheric tower also can further be carried out rectification under vacuum, isolate aromatic solvent and tar.Such scheme by rectification under vacuum with cracking C
9 +Vinylbenzene component in the cut is effectively separated with two methyl cyclopentadiene components with dicyclopentadiene, obtains high-quality petroleum resin raw material, obtains highly purified cyclopentadiene and methyl cyclopentadiene by atmospheric distillation, thereby makes cracking C
9 +Various valuable constituents in the cut obtain fully effectively utilizing.
In the method for the invention, (1) goes on foot cracking C
9 +The cut of rich in styrene is told in cut rectification under vacuum, cat head, distillates with vinylbenzene with cyclopentadiene other light constituent close with the methyl cyclopentadiene boiling point simultaneously, obtains containing the heavy constituent of dicyclopentadiene at the bottom of the tower.For dicyclopentadiene and other component in the cut are reacted, require rectification temperature to be no more than the decomposition temperature of dicyclopentadiene, suitable rectification temperature is 50～130 ℃, preferred 60～110 ℃.Tower top temperature is 50～70 ℃ during rectification under vacuum, and preferred 60～70 ℃, column bottom temperature is 80～130 ℃, preferred 90～110 ℃.Preferred 0.005～the 0.03MPa of the pressure of rectification under vacuum.(1) cut of the rich in styrene that obtains of step rectification under vacuum is fine petroleum resin raw materials, easy polymeric vinylbenzene isoreactivity component, the component concentration close with methyl cyclopentadiene with cyclopentadiene significantly reduce in the heavy constituent, have created condition for further extracting high-purity cyclopentadiene and methyl cyclopentadiene.
The inventive method (2) step is for extracting high-purity cyclopentadiene and methyl cyclopentadiene and holding concurrently and produce the sepn process of other product.At first described tower bottom distillate of (1) step is heated to 180～380 ℃, preferred 180～340 ℃, dicyclopentadiene and two methyl cyclopentadiene are decomposed, again it is sent into the atmospheric distillation tower, separate each component successively by the boiling point height.Tell the minimum cyclopentadiene cut of boiling point by the atmospheric distillation column overhead, tell the methyl cyclopentadiene cut, tell the cut that is rich in dicyclopentadiene, tell the higher cut of indenes content by the middle and lower part side line of tower by the middle part side line of tower by the top side line of tower.Described (1) step tower bottom distillate Heating temperature is also unsuitable too high, to avoid active ingredient generation heat polymerization.Be 5～60 minutes heat-up time, and preferred 5～45 minutes, the best was 5～30 minutes.
Described atmospheric distillation column overhead temperature preferably is controlled to be 35～45 ℃, and the cyclopentadiene cut that cat head is told is all discharged, also can be after condenser condenses, and a part is back to cat head, and a part is discharged, and reflux ratio is 10～1: 1～10, preferred 5～1: 1～10.
The temperature of being isolated the methyl cyclopentadiene cut by atmospheric distillation tower top side line preferably is controlled to be 65～75 ℃, and the methyl cyclopentadiene cut of telling is all discharged, also can be after condensation, a part refluxes, a part is discharged, and reflux ratio is 10～1: 1～10, and preferred 5～1: 1～10.
The temperature of being told the cut that is rich in dicyclopentadiene by atmospheric distillation tower middle part side line preferably is controlled to be 150～180 ℃.The cut that is rich in dicyclopentadiene that preferably will tell is through condensation, and a part is back to the bottom of methyl cyclopentadiene extraction side line, and a part is discharged.Reflux ratio is 10～1: 1～5, preferred 5～1: 1.Can guarantee the thermally equilibrated while of rectifying tower like this, make undecomposed dicyclopentadiene and two methyl cyclopentadiene that scission reaction further take place, thereby improve the output of cyclopentadiene and methyl cyclopentadiene.
The temperature of being told the higher cut of indenes content by atmospheric distillation tower middle and lower part side line preferably is controlled to be 170～204 ℃.The cut that the indenes content of telling is higher is through condensation, and a part is back to the bottom of being rich in dicyclopentadiene cut extraction side line, and a part is discharged, and reflux ratio is 10～1: 1～5, and preferred 5～1: 1.
(2) tell more preferably 40～42 ℃ of the temperature of cyclopentadiene cut described in the step by the atmospheric distillation column overhead, tell more preferably 70～72 ℃ of the temperature of methyl cyclopentadiene cut by the top side line, tell more preferably 160～170 ℃ of the temperature of the cut that is rich in dicyclopentadiene by tower middle part side line; The temperature of being told the higher cut of indenes content by tower middle and lower part side line is more preferably 170～190 ℃.
(2) isolated heavy ends at the bottom of the atmospheric distillation tower preferably carries out rectification under vacuum again the step, isolates aromatic solvent and tar.Preferred 0.03～the 0.003MPa of the pressure of described rectification under vacuum, tower top temperature is controlled to be 120～180 ℃, and preferred 135～175 ℃, column bottom temperature is controlled to be 150～220 ℃, preferred 165～205 ℃.
The inventive method is applicable to dicyclopentadiene and two higher cracking ethylene preparation by product C of methyl cyclopentadiene content
9 +Fraction separation is utilized.Described C
9 +Cut is that boiling range is 120～300 ℃ a cut in solar oil or the naphtha cracking system ethylene process, and wherein styrene content is 1～10 quality %, and the content of dicyclopentadiene and methyl bicycle pentadiene is greater than 15 quality %.
Below in conjunction with Fig. 1 the present invention is described.Among Fig. 1, cracking by-product C
9 +Cut enters rectification under vacuum tower E-3 by pipeline P-1, and the cut of rich in styrene is discharged by pipeline P-2, and tower bottom distillate is discharged by pipeline P-3, sends into atmospheric distillation tower E-1 after being heated to 180～380 ℃ by interchanger E-2.The cyclopentadiene that boiling point is minimum distillates through pipeline P-5 from cat head, discharges from pipeline P-14 after overhead condenser E-4 condensation, also partial reflux can be arranged, and cat head distilled cyclopentadiene cut purity surpasses 96.0 quality %.The first side line P-11 distillates methyl cyclopentadiene from tower top, discharges from pipeline P-13 after condenser E-6 condensation, also partial reflux can be arranged, and distilled methyl cyclopentadiene cut purity surpasses 96.0 quality %.The dicyclopentadiene cut that is rich in that boiling point is higher distillates from atmospheric distillation tower middle part second side line, after condenser heat exchange condensation, part refills from the lower pipelines P-12 that methyl cyclopentadiene distillates mouth, and reflux ratio preferably is controlled to be 10: 1～1: 10, and part is discharged by pipeline P-6.The indenes cut that boiling point is higher distillates from rectifying tower middle and lower part the 3rd side line, after condenser heat exchange condensation, part refills from the lower pipelines P-15 that dicyclopentadiene cut section distillates mouth, and control of reflux ratio is 10: 1～1: 10, part is discharged by pipeline P-7, also can not reflux.The higher heavy ends of tower bed coke oil-contg distillates from tower bottom, can directly send into second rectification under vacuum tower E-5 through pipeline P-8 and further separate, and aromatic solvent is discharged from overhead line P-9, and tar is discharged from tower bottom tube line P-10.
Further specify the present invention below by example, but the present invention is not limited to this.
Example 1
Press the flow process of Fig. 1, with the cracking C that is heated to 90 ℃ to form shown in the table 1
9 +Cut is delivered to rectification under vacuum tower E-3 with the speed of 50g/h, and control tower pressure is 0.01MPa, and tower top temperature is 60～70 ℃, and column bottom temperature is 95～105 ℃.The vinylbenzene cut that cat head obtains distillates with the speed of 8g/h, and its main ingredient content sees Table 2.Tower bottom distillate is discharged the rectification under vacuum tower with the speed of 42g/h, and the main ingredient content of tower bottom distillate sees Table 3.
Tower bottom distillate is heated to 220 ℃ by interchanger E-2, and be 20 minutes heat-up time, sends into atmospheric distillation tower E-1 then.Atmospheric distillation column overhead temperature is controlled to be 40～42 ℃, the minimum cyclopentadiene of boiling point is distillated from cat head.Methyl cyclopentadiene distillates from the first side line P-11 on tower top, and recovered temperature is controlled to be 70～72 ℃.Rectifying tower middle part second side line distillate boiling point higher be rich in the dicyclopentadiene cut, the second side line recovered temperature is controlled to be 160～167 ℃, this cut refills rectifying tower through condenser heat exchange condensation rear section from pipeline P-12, and the control reflux ratio is 1: 2, and remainder is discharged by pipeline P-6.Rectifying tower middle and lower part the 3rd side line distillates the higher indenes cut of boiling point, and recovered temperature is 180～185 ℃.The higher heavy ends of residue tar content distillates after pipeline P-8 sends into second rectification under vacuum tower E-5 at the bottom of tower at the bottom of the tower, and pressure-controlling is 0.005MPa, and tower top temperature is controlled to be 135～155 ℃, and column bottom temperature is controlled to be 165～185 ℃.The aromatic solvent that cat head obtains is discharged by pipeline P-9, and the tar that obtains at the bottom of the tower is discharged by pipeline P-10.See Table 4 through normal pressure rectifying and each cut content that rectification under vacuum for the second time obtains, each cut essential substance content sees Table 5.
Example 2
Press the method separating and cracking C of example 1
9 +Cut, different is to send into atmospheric distillation tower E-1 after rectification under vacuum tower E-3 tower bottom distillate is heated to 260 ℃, and the reflux ratio of control atmospheric distillation tower second side line is 2: 1.See Table 4 through normal pressure rectifying and each cut content that rectification under vacuum for the second time obtains, each cut essential substance content sees Table 5.
Example 3
Press the method separating and cracking C of example 1
9 +Each component of cut, different is that atmospheric distillation tower the 3rd side line distilled indenes cut is refluxed through the condensation rear section, and reflux ratio is 2: 1, and part is discharged by pipeline P-7.See Table 4 through normal pressure rectifying and each cut content that rectification under vacuum for the second time obtains, each cut essential substance content sees Table 5.
Table 1
| The component title | Content, quality % |
| Cyclopentadiene | 0.52 |
| The component title | Content, quality % |
| Methyl cyclopentadiene | 0.19 |
| Benzene | 0.10 |
| Toluene | - |
| Ethylbenzene | - |
| To, m-xylene | - |
| Vinylbenzene | 7.79 |
| O-Xylol | 2.45 |
| Propenylbenzene | - |
| N-propylbenzene | - |
| Ethyl methyl benzene | 1.73 |
| C 9Aromatic hydrocarbons | 1.90 |
| C 9Unsaturated aromatic hydrocarbon | 18.32 |
| C 10Aromatic hydrocarbons | 0.98 |
| Dicyclopentadiene | 20.33 |
| Indenes | 8.57 |
| Two methyl cyclopentadienes | 7.55 |
| The methyl indenes | 2.49 |
| Naphthalene | 7.50 |
| Methylnaphthalene | 0.43 |
| Other | 19.15 |
Table 2
| The component title | Content, quality % |
| Vinylbenzene | 47.3 |
| Dicyclopentadiene | 4.1 |
| Vinyl toluene | 3.6 |
| Indenes | ＜1 |
| The methyl indenes | - |
Table 3
| The component title | Content, quality % |
| Vinylbenzene | 0.41 |
| C 9 +Aromatic hydrocarbons | 3.2 |
| C 9 +Unsaturated aromatic hydrocarbon | 19.82 |
| Dicyclopentadiene | 29.20 |
| Indenes | 11.17 |
| Two methyl cyclopentadienes | 10.55 |
| The methyl indenes | 4.62 |
| Naphthalene | 9.33 |
| Other | 11.7 |
Table 4
Table 5
Claims (10)
1. cracking ethylene preparation by product C
9 +Fraction separation is utilized method, comprises the steps:
(1) with C
9 +Cut is divided into rich in styrene cut and tower bottom distillate with rectification under vacuum, and the pressure that carries out rectification under vacuum is 0.005～0.03MPa, and tower top temperature is 50～70 ℃ during rectification under vacuum, and column bottom temperature is 80～130 ℃;
(2) after (1) step, described tower bottom distillate was heated to 180～380 ℃, carry out atmospheric distillation, at the bottom of tower, isolate cyclopentadiene cut, methyl cyclopentadiene cut, the cut that is rich in dicyclopentadiene, higher cut and the heavy ends of indenes content by the atmospheric distillation cat head successively
Described C
9 +Cut is that boiling range is 120～300 ℃ a cut in solar oil or the naphtha cracking system ethylene process, and wherein styrene content is 1～10 quality %, and the content of dicyclopentadiene and two methyl cyclopentadienes is greater than 15 quality %.
2. in accordance with the method for claim 1, it is characterized in that in (2) step described tower bottom distillate of (1) step being heated to 200～340 ℃.
3. in accordance with the method for claim 1, it is characterized in that telling the cyclopentadiene cut by the atmospheric distillation column overhead in (2) step, top side line by tower is told the methyl cyclopentadiene cut, middle part side line by tower is told the cut that is rich in dicyclopentadiene, tells the higher cut of indenes content by tower middle and lower part side line.
4. in accordance with the method for claim 3, it is characterized in that described atmospheric distillation column overhead temperature is controlled to be 35～45 ℃, the cyclopentadiene cut that cat head is told is after condenser condenses, and a part is back to cat head, and a part is discharged.
5. in accordance with the method for claim 3, it is characterized in that the described temperature of isolating the methyl cyclopentadiene cut by atmospheric distillation tower top side line is controlled to be 65～75 ℃, the methyl cyclopentadiene cut of telling is through condensation, and a part refluxes, and a part is discharged.
6. in accordance with the method for claim 3, it is characterized in that the described temperature of telling the cut that is rich in dicyclopentadiene by atmospheric distillation tower middle part side line is controlled to be 150～180 ℃, the cut of telling that is rich in dicyclopentadiene is through condensation, a part is back to the bottom of methyl cyclopentadiene extraction side line, and a part is discharged.
7. in accordance with the method for claim 3, it is characterized in that the described temperature of telling the higher cut of indenes content by atmospheric distillation tower middle and lower part side line is controlled to be 170～204 ℃, the higher cut of the indenes content of telling is through condensation, a part is back to the bottom of being rich in dicyclopentadiene cut extraction side line, and a part is discharged.
8. in accordance with the method for claim 3, it is characterized in that the temperature of telling the cyclopentadiene cut by the atmospheric distillation column overhead described in (2) step is 40～42 ℃, the temperature of being told the methyl cyclopentadiene cut by the top side line is 70～72 ℃, the temperature of being told the cut that is rich in dicyclopentadiene by tower middle part side line is 160～170 ℃, and the temperature of being told the higher cut of indenes content by tower middle and lower part side line is 170～190 ℃.
9. in accordance with the method for claim 1, it is characterized in that (2) step isolated heavy ends at the bottom of the atmospheric distillation tower isolates aromatic solvent and tar through rectification under vacuum.
10. in accordance with the method for claim 9, the pressure that it is characterized in that described rectification under vacuum aromatics separation solvent and tar is 0.03～0.003MPa.
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| CN101619121B (en) * | 2009-07-29 | 2014-01-01 | 宁波职业技术学院 | Method for preparing cracked C5 modified DCPD petroleum resin |
| CN102675030B (en) * | 2012-04-18 | 2015-01-07 | 天津大学 | Process method for directly separating petroleum resin raw materials from cracking C9 fraction |
| CN104276914B (en) * | 2013-07-12 | 2018-11-20 | 中国石油化工股份有限公司 | Utilize the method for rectifying column separation petroleum cracking Crude products.deep process C9~C10 fraction |
| CN104276915B (en) * | 2013-07-12 | 2018-03-06 | 中国石油化工股份有限公司 | A kind of separation method of C9~C10 cuts |
| CN105111036A (en) * | 2015-09-22 | 2015-12-02 | 天津天大天海化工新技术有限公司 | Novel method for separating cyclopentadiene and methyl cyclopentadiene from ethylene by-product C9 |
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