CN106588552A - Method for selective hydrogenation of C5 fraction to remove pentone - Google Patents
Method for selective hydrogenation of C5 fraction to remove pentone Download PDFInfo
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Abstract
Belonging to the technical field of organic chemical industry, the invention in particular relates to a method for selective hydrogenation of C5 fraction to remove pentone. The method specifically includes the steps of: (1) nitrogen removal: subjecting C5 fraction to nitrogen removal treatment by a fixed bed loaded with sulfonic cation exchange resin and water; and (2) selective hydrogenation: subjecting the nitrogen removed C5 fraction to selective hydrogenation through a bubbling bed reactor loaded with a Pd/MgO catalyst so as to convert pentone into isoprene. The method provided by the invention has the advantages of simple process, no wastewater discharge, high nitrogen removal precision and no material loss, and can effectively prevent polymerization side reaction.
Description
Technical field
The invention belongs to field of chemical technology, and in particular to a kind of side of C 5 fraction selective hydrogenation and removing pentone
Method.
Background technology
The a considerable amount of C 5 fractions of by-product during naphtha steam cracking ethylene, C 5 fraction can be with by separation
Production pentadiene, isoprene and dicyclopentadiene product, these three diolefins are due to its special molecular structure, chemistry
Property is active, and a series of higher chemical products of extra prices can be converted into after Downstream processing.
During the segregation apparatuss of carbon five production isoprene, generally adopt with DMF (hereinafter referred to as
DMF) for the extraction rectification technique twice of extractant, to carry out, isoprene is refined, and the effect of extractant is to change C 5 fraction
The relative volatility of each component, realizes the separation of each component.The major function of the first extracting rectifying is by the way that the raw material of carbon five is entered
Row extracting rectifying, from removed overhead alkane therein and monoolefine, the isoprene and a small amount of alkynes and DMF contained by tower reactor is again
Jing desorbers make hydro carbons separate with DMF, then the hydro carbons obtained from tower top is carried out into rectification, the most pentadiene of removing, ring
Pentadiene, cyclopentenes, Pentamethylene., from tower top the chemical grade isoprene product of content more than 98% is obtained.Second extraction essence
The major function for evaporating is with chemical grade isoprene as raw material, after appropriate DMF is added, by extraction in extractive distillation column
Taking rectification makes isoprene separate with cyclopentadiene and pentone, and the thick isoprene that tower top is obtained sends into lightness-removing column and carries out essence
System, tower bottoms then sends into stripper makes hydro carbons separate with DMF.From the C 5 fraction of lightness-removing column overhead extraction, side take-off contains
Polymerization grade isoprene product of the amount more than 99.5%, tower reactor is then heavy component.The produced quantity of C 5 fraction is about polymer grade
The 49% of isoprene product quality, in C 5 fraction, generally 1～5%, remaining is mainly isoamyl to pentone content
Diene and micro dimethylamine.At present in the segregation apparatuss of carbon five, be C 5 fraction is mixed with the raw material of the device of carbon five after, weigh
New work is that raw material enters the segregation apparatuss of carbon five, or is separated C 5 fraction as by-product from device.Due to polymer grade isoamyl
Main impurity is three kinds of valerylene, pentone and cyclopentadiene in diene, and recycled C 5 fraction will improve raw material
In pentone content, such as to meet the requirement of pentone content≤5mg/kg in polymerization grade isoprene product, certainly will
Operating severity is improved, increases energy consumption；And such as separate C 5 fraction as by-product from device, isoamyl can be significantly reduced
The yield of diene.Additionally, during isoprene extracting rectifying, due to the presence for having trace water, a small amount of DMF can send out
Raw hydrolysis are converted into formic acid and dimethylamine, therefore the C 5 fraction for producing can introduce a small amount of dimethylamine and present compared with highly basic
Property.
The content of the invention
In order to overcome problems of the prior art, it is an object of the invention to provide a kind of C 5 fraction choosing of process is simple
The method of selecting property hydrogenation and removing pentone.C 5 fraction is a kind of high-quality for producing polymerization grade isoprene after present invention hydrogenation
Raw material.
The inventive method is by C 5 fraction by being equipped with the fixed bed of sulfonic group cation exchange resin/water composition to remove diformazan
Amine, then carrying out selective hydrogenation by the bubbling bed reactor equipped with Pd/MgO catalyst makes pentone be converted into isoamyl two
Alkene, the following is specific technical scheme of the invention.
A kind of method of C 5 fraction selective hydrogenation and removing pentone, comprises the following steps that：
(1) denitrogenation
C 5 fraction is carried out into denitrogenation processing by loading the fixed bed of sulfonic group cation exchange resin and water；Wherein denitrogenation temperature
Spend for 5～50 DEG C, mass space velocity is 3～15hr-1, system pressure is the mass ratio of 0.1～0.6MPa, water and C 5 fraction
For 0.01:1～0.01:2；
(2) selective hydrogenation
C 5 fraction after denitrogenation is carried out into selective hydrogenation by the bubbling bed reactor equipped with Pd/MgO catalyst makes iso-amylene
Alkynes is converted into isoprene；Wherein：The LHSV of reaction is 10～40hr-1, system pressure is 0.3～1.5MPa, is reacted
Temperature is 30～70 DEG C, and C 5 fraction pentone is 1: 1～1 with the mol ratio of hydrogen:4.0；With the quality of carrier MgO
Meter, the mass fraction of Pd is 0.1～0.4% in Pd/MgO catalyst.
In above-mentioned steps (1), described denitrification temperature is 20～40 DEG C；Mass space velocity is 6～9hr-1；System pressure is
0.3～0.5MPa；Deionized water is 0.01 with the mass ratio of C 5 fraction:1.1～0.01:1.5.
In above-mentioned steps (2), LHSV is 20～30hr-1, system pressure be 0.8～1.3MPa, reaction temperature be 40～
60 DEG C, pentone and the mol ratio of hydrogen are 1: 1～1 in C 5 fraction:3.0.
In above-mentioned steps (2), Pd/MgO catalyst is loaded to the active component nitrate solution of catalyst by infusion process
On carrier MgO, prepare after dry, roasting.Preferably, baking temperature be 80～200 DEG C, sintering temperature be 300～
550℃。
In above-mentioned steps (2), it is preferred that in terms of the quality of carrier MgO, the mass fraction of Pd is in Pd/MgO catalyst
0.2～0.35%.
In above-mentioned steps (2), in Pd/MgO catalyst, carrier MgO is spherical.
In above-mentioned steps (2), in Pd/MgO catalyst, the particle diameter of carrier MgO is 3～5mm, and specific surface area is 100～300m2/g,
Pore volume is 0.1～0.6ml/g.It is further preferred that in Pd/MgO catalyst, the specific surface area of carrier MgO is 150～
250m2/ g, pore volume is 0.2～0.5ml/g.
In the present invention, the fixed bed reactors that C 5 fraction is consisted of sulfonic group cation exchange resin/water realize two
Methylamine removes the dual-use function with wastewater treatment, and effectively prevents the oligomerisation of unsaturated hydrocarbons contained in C 5 fraction anti-
Should, at the same the C 5 fraction after denitrogenation by equipped with Pd/MgO catalyst bubbling bed reactor carry out selective hydrogenation make it is different
Amylene alkynes is converted into isoprene, and C 5 fraction is a kind of quality raw materials for producing isoprene after hydrogenation.
Inventor passes through to study discovery, the dissolubility based on dimethylamine in water, and the acid-base reaction that reaction rate is exceedingly fast,
On the basis of many experiments, the de- dimethylamine of C 5 fraction and wastewater treatment are realized in a reactor while what is completed sets
Think.Speculate from point of theory, it is believed that the dimethylamine in C 5 fraction is first dissolved in the water, be dissolved in the dimethylamine of water in sulfonic acid
Base cation exchange resin surface adsorption, and make dimethylamine be solidificated in resin surface by quick neutralization reaction and taken off
Remove, while water quality is purified, without the need for discharge.Generally unsaturated hydrocarbons are easily sent out on sulfonic group cation exchange resin surface
Raw oligomerisation reaction, but when resin surface is immersed in water, because water is filled with the duct of resin so that it is water-fast not
Saturated hydrocarbons cannot adsorb in resin surface, and water serves the buffer action between resin and reactant, prevents oligomerisation anti-
The generation answered.Furthermore, while C 5 fraction has certain dissolubility in water, but because without discharge of wastewater, material is not damaged
Lose.
For C 5 fraction selective hydrogenation and removing pentone process, inventor is had found, can be obtained using Pd/MgO catalyst
Obtain preferable hydrogenation selectivity it is critical only that adsorptive selectivity of the catalyst to alkynes.Theoretically speculating, isoprene
All chemisorbed can occur in catalyst surface with pentone, and then the hydrogen atom with absorption in catalyst surface carries out addition
Reaction, although therefore have a small amount of isoprene to be hydrogenated with, due to pentone, in catalyst table, absorbability is higher, isoamyl
Eneyne catalyst surface concentration be much larger than isoprene so that hydrogenation reaction with pentone be hydrogenated with based on, so as to realize
Remove via selective hydrogenation the purpose of alkynes.Hydrogenation is preferably carried out using bubbling bed reactor, and its hydrogenation selectivity is compared with three
Phase trickle bed is advantageously.
After selective hydrogenation is carried out, in the C 5 fraction of hydrogenation, the content of pentone is typically reduced to below 15mg/kg,
Isoprene content is about 97%, is a kind of quality raw materials for producing isoprene, it is former with the fresh carbon five of the device of carbon five
After material mixing, the content of isoprene in raw material can be improved, reduce the operating severity of process units, reduce energy consumption,
And the pentone content further reduced in polymerization grade isoprene product is possibly realized, improve product matter beneficial to continuation
Amount.
Compared with prior art, the beneficial effects of the present invention is：
(1) by the way that C 5 fraction is carried out into removing diformazan by the fixed bed constituted equipped with sulfonic group cation exchange resin/water
Amine, then selective hydrogenation is carried out by the bubbling bed reactor equipped with Pd/MgO catalyst, C 5 fraction is a kind of after hydrogenation
The quality raw materials of production isoprene；
(2) process is simple, non-wastewater discharge, denitrogenation high precision, material free of losses, can effectively prevent polymerization side reactions；
(3) after the C 5 fraction after hydrogenation is mixed with the fresh raw material of carbon five of the device of carbon five, isoamyl two in raw material can be improved
The content of alkene, reduces the operating severity of process units, reduces energy consumption, and makes further to reduce polymerization grade isoprene
Pentone content in product is possibly realized, beneficial to continuation improve product quality.
Specific embodiment
The details of the present invention is further described below by embodiment.
【Embodiment 1～10】
First, C 5 fraction raw material
The C 5 fraction that embodiment 1～10 is used derives from the segregation apparatuss of carbon five when isoprene is produced, a part for extraction
Material.The component of C 5 fraction is shown in Table 1.
Table 1.
| Component | C 5 fraction |
| Total carbon four, % | 0.04 |
| 3- methyl butene -1, % | 0.00 |
| 1.4- pentadienes, % | 0.00 |
| 2-butyne, % | 0.02 |
| Pentone, % | 1.91 |
| 2- methyl butene -1, % | 0.00 |
| Isoprene, % | 97.15 |
| 2- methyl butene -2, % | 0.05 |
| Cyclopentadiene, % | 0.26 |
| Cyclopentenes, % | 0.48 |
| Other carbon five, % | 0.08 |
| Dimethylamine, % | 0.01 |
| pH | 9 |
2nd, the de- dimethylamine of C 5 fraction
The de- dimethylamine of C 5 fraction is carried out in water scrubber size is for the stainless steel tube of φ 25mm × 1500mm, is loaded in pipe
Particle diameter is 100 grams of composition resin beds of spherical sulfonic group cation exchange resin catalyst of 0.40～1.25mm, resin
Mass exchange capacity is 5.0mmol/g, and resin is produced by Shandong Qilu Keli Chemical Research Institute Co., Ltd., model
QRE-01.Reaction feed amount is returned the back pressure valve regulation of material storage tank by being installed on after washing by feed pump control, system pressure.
Before experiment starts, will be disengaged from sub- water and be filled with water scrubber, until the liquid level of water reach be higher by resin bed height 20～
30mm.Start water-circulating pump, deionized water from top to bottom flows through resin bed, after stable, start and return material charging
Pump, oil phase returns material and countercurrently enters resin bed from the bottom to top.Oil phase flows out Jing after sedimentation point water from water scrubber top.Depart from
Sub- water is 0.01 with the mass ratio for returning material:1.1～0.01:1.5, mass space velocity is 3～15hr-1；Reaction temperature is 5～50
℃；Reaction pressure is 0.2～0.6MPa.The content of dimethylamine can be obtained by the measure of basicity before and after washing, basicity
Measure using dimethylamine algoscopy in SH/T0162-1992 oil products.The condition of enforcement is shown in Table 2, the results are shown in Table 3.
Table 2.
Table 3.
| Diformazan amine content (%) | pH | |
| Embodiment 1 | ≤0.00005 | 7.0 |
| Embodiment 2 | ≤0.00005 | 7.0 |
| Embodiment 3 | ≤0.00005 | 7.0 |
| Embodiment 4 | ≤0.00005 | 7.0 |
| Embodiment 5 | ≤0.00005 | 7.0 |
| Embodiment 6 | ≤0.00005 | 7.0 |
| Embodiment 7 | ≤0.00005 | 7.0 |
| Embodiment 8 | ≤0.00005 | 7.0 |
| Embodiment 9 | ≤0.00005 | 7.0 |
| Embodiment 10 | ≤0.00005 | 7.0 |
3rd, after denitrogenation C 5 fraction selective hydrogenation
The selective hydrogenation of C 5 fraction is in the rustless steel tubular type bubbling bed reactor that size is φ 25mm × 1500mm after denitrogenation
In carry out.Load 100 grams of composition beds of spherical Pd/MgO catalyst that particle diameter is 3～5mm in pipe.Catalyst Pd's
Mass fraction is 0.1～0.4%, and the specific surface area of carrier MgO is 100～300m2/ g, pore volume is 0.1～0.6ml/g.LHSV
For 10～40hr-1, system pressure is 0.8～1.5MPa, and reaction temperature is 30～70 DEG C, C 5 fraction pentone and hydrogen
The mol ratio of gas is 1: 1～1：4.0.Before charging, first with nitrogen displacement, the oxygen in hydrogenation reactor is driven out of, then
Temperature is risen to into 100 DEG C, catalyst is activated 5～15 hours under conditions of Hydrogen Vapor Pressure is 1.0MPa, carried out after cooling anti-
Should., by feed pump control, system pressure is by the back pressure valve regulation for being installed on high score tank for reaction feed amount.
Hydrogenation reactor is sent into by top with the speed for setting with pump after C 5 fraction is preheated after denitrogenation, hydrogen is by gas point
Cloth device is entered in reactor, and C 5 fraction material carries out hydrogenation reaction after mixing with hydrogen into beds.Hydrogenation material
One gas-liquid separator is entered by hydrogenation reactor bottom, liquid phase material enters product storage tank.By gas-liquid separator separate it is not anti-
Answer to be entered after the adjusted valve decompression of hydrogen and empty after wet-test meter metering, or Returning reacting system after compression.Hydrogenated products pass through
Gas chromatogram is analyzed.The reaction condition and hydrogenation of each embodiment the results are shown in Table 4.
Table 4.
Claims (9)
1. a kind of method of C 5 fraction selective hydrogenation and removing pentone, it is characterised in that comprise the following steps that：
(1) denitrogenation
C 5 fraction is carried out into denitrogenation processing by loading the fixed bed of sulfonic group cation exchange resin and water；Wherein denitrogenation temperature
Spend for 5～50 DEG C, mass space velocity is 3～15hr-1, system pressure is the mass ratio of 0.1～0.6MPa, water and C 5 fraction
For 0.01:1～0.01：2.0；
(2) selective hydrogenation
C 5 fraction after denitrogenation is carried out into selective hydrogenation by the bubbling bed reactor equipped with Pd/MgO catalyst makes iso-amylene
Alkynes is converted into isoprene；Wherein：The LHSV of reaction is 10～40hr-1, system pressure is 0.3～1.5MPa, is reacted
Temperature is 30～70 DEG C, and C 5 fraction pentone is 1: 1～1 with the mol ratio of hydrogen：4.0；With the matter of carrier MgO
Gauge, the mass fraction of Pd is 0.1～0.4% in catalyst.
2. method according to claim 1, it is characterised in that in step (1), described denitrification temperature is 20～40
℃；Mass space velocity is 6～9hr-1；System pressure is 0.3～0.5MPa；Water is 0.01 with the mass ratio of C 5 fraction:1.1～
0.01：1.5.
3. method according to claim 1, it is characterised in that：In step (2), LHSV is 20～30hr-1, system pressure
Power is 0.8～1.3MPa, and reaction temperature is 40～60 DEG C, in C 5 fraction the mol ratio of pentone and hydrogen be 1: 1～
1：3.0.
4. method according to claim 1, it is characterised in that in step (2), Pd/MgO catalyst will by infusion process
The active component nitrate solution of catalyst is loaded on carrier MgO, is prepared after dry, roasting.
5. method according to claim 4, it is characterised in that baking temperature is 80～200 DEG C, sintering temperature is 300～
550℃。
6. method according to claim 1, it is characterised in that in step (2), in terms of the quality of carrier MgO, Pd/MgO
The mass fraction of Pd is 0.2～0.35% in catalyst.
7. method according to claim 1, it is characterised in that in step (2), in Pd/MgO catalyst, carrier MgO
For spherical.
8. method according to claim 1, it is characterised in that in step (2), in Pd/MgO catalyst, carrier MgO
Particle diameter be 3～5mm, specific surface area be 100～300m2/ g, pore volume is 0.1～0.6ml/g.
9. method according to claim 8, it is characterised in that in step (2), in Pd/MgO catalyst, carrier MgO
Specific surface area be 150～250m2/ g, pore volume is 0.2～0.5ml/g.
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Cited By (7)
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| CN109721452A (en) * | 2017-10-27 | 2019-05-07 | 中国石油化工股份有限公司 | The removal methods of pentone in C5 fraction |
| CN109721460A (en) * | 2017-10-27 | 2019-05-07 | 中国石油化工股份有限公司 | Using the technique of pentone in the removing C5 fraction of metal-modified adsorbent |
| CN109721455A (en) * | 2017-10-27 | 2019-05-07 | 中国石油化工股份有限公司 | The method for preparing high-purity pentadiene |
| CN109721458A (en) * | 2017-10-27 | 2019-05-07 | 中国石油化工股份有限公司 | A kind of method of 2- butine and pentone in removing C5 fraction |
| CN111099951A (en) * | 2018-10-25 | 2020-05-05 | 中国石油化工股份有限公司 | Comprehensive utilization method of light carbon five |
| CN111100244A (en) * | 2018-10-25 | 2020-05-05 | 中国石油化工股份有限公司 | Modified pentadiene hydrogenated petroleum resin and preparation method thereof |
| CN113750993A (en) * | 2021-10-15 | 2021-12-07 | 中国科学院大连化学物理研究所 | Palladium monoatomic catalyst, preparation method thereof and application thereof in Suzuki coupling reaction |
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| CN113750993A (en) * | 2021-10-15 | 2021-12-07 | 中国科学院大连化学物理研究所 | Palladium monoatomic catalyst, preparation method thereof and application thereof in Suzuki coupling reaction |
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