CN108017500A - The removal methods of pentone in C5 fraction - Google Patents

The removal methods of pentone in C5 fraction Download PDF

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Publication number
CN108017500A
CN108017500A CN201610963467.5A CN201610963467A CN108017500A CN 108017500 A CN108017500 A CN 108017500A CN 201610963467 A CN201610963467 A CN 201610963467A CN 108017500 A CN108017500 A CN 108017500A
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fraction
pentone
isoprene
removal methods
methods according
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Inventor
常慧
陆鑫
曹强
叶军明
夏蓉晖
孙骏
瞿卫国
方玲
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China Petroleum and Chemical Corp
Sinopec Shanghai Petrochemical Co Ltd
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China Petroleum and Chemical Corp
Sinopec Shanghai Petrochemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/005—Processes comprising at least two steps in series
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
    • C07C7/167—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation for removal of compounds containing a triple carbon-to-carbon bond

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention belongs to field of chemical technology, the removal methods of pentone specially in a kind of C 5 fraction.This method comprises the following steps that：(1) C 5 fraction is subjected to denitrogenation processing by the fixed bed equipped with sulfonic group cation exchange resin and water；(2) the isoprene material after denitrogenation is hydrogenated with by the making choice property of bubbling bed reactor of the Pb series catalysts handled equipped with partial vulcanization, pentone is converted into isoprene；Effect of the invention is that：Technological operation is simple, denitrogenation precision is high, pentone high conversion rate, and isoprene loss is few, can effectively improve the product quality of isoprene.

Description

The removal methods of pentone in C5 fraction
Technical field
The invention belongs to field of chemical technology, and in particular to the removal methods of pentone in a kind of C5 fraction.
Background technology
The a considerable amount of C 5 fractions of by-product during naphtha steam cracking ethene, C 5 fraction pass through separation Pentadiene, isoprene and dicyclopentadiene product can be produced, these three diolefins are changed due to its special molecular structure It is active to learn property, a series of higher chemical products of extra prices can be converted into after Downstream processing.
During light dydrocarbon separator produces isoprene, generally use is with n,N-Dimethylformamide (following letter DMF) it is referred to as that the extraction rectification technique twice of extractant refines to carry out isoprene, 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 first extracting rectifying be by by light dydrocarbon raw material into Row extracting rectifying, from removed overhead alkane therein and monoolefine, isoprene and a small amount of alkynes and DMF contained by tower reactor pass through again Desorber makes hydro carbons be separated with DMF, then the hydro carbons obtained from tower top is carried out rectifying, removes most pentadiene, ring penta 2 Alkene, cyclopentene, pentamethylene, the chemical grade isoprene product of content more than 98% is obtained from tower top.The master of second extracting rectifying It is using chemical grade isoprene as raw material to want function, after suitable DMF is added, is made in extractive distillation column by extracting rectifying Isoprene is separated with cyclopentadiene and pentone, and the thick isoprene that tower top obtains is sent into lightness-removing column and is refined, tower reactor Liquid, which is then sent into stripper, makes hydro carbons be separated with DMF.From the C 5 fraction of lightness-removing column overhead extraction, side take-off content is 99.5% Polymerization grade isoprene product above, tower reactor is then heavy component.The produced quantity of C 5 fraction is about polymerization grade isoprene production The 49% of quality, in C 5 fraction, for pentone content usually 1~5%, remaining is mainly isoprene and micro two Methylamine.At present in light dydrocarbon separator, it is after C 5 fraction is mixed with the raw material of light dydrocarbon device, is re-used as raw material entrance Light dydrocarbon separator, or separated using C 5 fraction as accessory substance from device.Due to main miscellaneous in polymerization grade isoprene Matter is three kinds of 2- butine, pentone and cyclopentadiene, and the pentone that recycled C 5 fraction will be improved in raw material contains Amount, will such as meet the requirement of pentone content≤15mg/kg in polymerization grade isoprene product, and it is harsh certainly will to improve operation Degree, increases energy consumption；And such as separated using C 5 fraction as accessory substance from device, the yield of isoprene can be significantly reduced.In addition, During isoprene extracting rectifying, due to there is the presence of trace water, a small amount of DMF can occur hydrolysis and be converted into formic acid And dimethylamine, therefore the C 5 fraction produced can introduce a small amount of dimethylamine and present compared with strong basicity.
The content of the invention
In order to overcome problems of the prior art, the present invention carries out light dydrocarbon using one kind by selective hydrogenation reaction The method that pentone removes in cut.C 5 fraction is a kind of high-quality original for producing polymerization grade isoprene after present invention hydrogenation Material.
The present invention is by C 5 fraction by the fixed bed formed equipped with sulfonic group cation exchange resin/water to remove diformazan Amine, the partial vulcanization of Pd series catalysts is poisoned, and reduces its activity, material is passed through the Pd series catalysts bubblings equipped with sulfurization Bed reactor, making choice hydrogenation reaction makes pentone be converted into isoprene, is the specific technical solution of the present invention below.
The present invention provides a kind of removal methods of pentone in C 5 fraction, after C5 fraction is carried out denitrogenation processing, Hydrogenation is selected under the action of the Pd series catalysts QSH-06 of partial vulcanization again, realizes the removing of pentone in C5 fraction.
In the present invention, C5 fraction is taken off by the fixed bed formed equipped with sulfonic group cation exchange resin/water Nitrogen processing.Preferably, denitrification temperature is 10~55 DEG C, and mass space velocity is 5~20hr-1, system pressure is 0.1~0.6MPa, water Mass ratio with C 5 fraction is 0.01:1~0.01:2.
In the present invention, the Pd series catalysts QSH-06 of partial vulcanization is reacted by Pd series catalysts QSH-06 and sulfur-containing compound Obtain, wherein：System pressure is 0.1~0.5MPa, and for reaction temperature between room temperature~100 DEG C, the reaction time is small for 1~48 When, mass space velocity is 5~50hr-1.Preferably, sulfur-containing compound is selected from H2S, in methyl sulfide, ethyl sulfide, methyl mercaptan or ethyl mercaptan Any one.
In the present invention, selection hydrogenation carries out in bubbling bed reactor.Preferably, select hydrogenation technique for：LHSV is 10 ~25hr-1, system pressure is 0.8~1.5MPa, and reaction temperature is 40~60 DEG C, and pentone and hydrogen rubs in C 5 fraction You are than being 1: 1~1：3.0.
In the present invention, the fixed bed reactors by C 5 fraction by sulfonic group cation exchange resin/water composition, are realized The dual-use function of diformazan amine removal and wastewater treatment, and effectively prevent the oligomerisation of unsaturated hydrocarbons contained in C 5 fraction Reaction, the poisoning of QSH-06 catalyst members is handled, although pentone and isoprene can occur in catalyst surface Chemisorbed, since catalyst activity position is reduced, the adsorption capacity of catalyst surface has declined, since pentone is being catalyzed Agent adsorption ability is strong, can be higher than isoprene in the concentration of catalyst surface, therefore with isoamyl in selective hydrogenation reaction Based on the hydrogenation reaction of eneyne.
C 5 fraction after denitrogenation is selected by the QSH-06 catalyst bubbling bed reactors handled equipped with sulfurization Selecting property hydrogenation reaction makes pentone be converted into isoprene, and C 5 fraction is a kind of to produce polymerization grade isoprene after hydrogenation Quality raw materials.
Inventor has found that the dissolubility based on dimethylamine in water, and the soda acid that reaction rate is exceedingly fast are anti-by studying Should, on the basis of many experiments, realize C 5 fraction and take off dimethylamine and wastewater treatment in a reactor while complete Imagination.Speculate from point of theory, it is believed that the dimethylamine in C 5 fraction is first dissolved in the water, and is dissolved in the dimethylamine of water in sulphur Acidic group cation exchange resin adsorption, and dimethylamine is solidificated in resin surface to be taken off by quick neutralization reaction Remove, while water quality is purified, without discharge.Usual unsaturated hydrocarbons easily occurs on sulfonic group cation exchange resin surface Oligomerisation reaction, but when resin surface soaks in water, since water is filled with the duct of resin so that unsaturation not soluble in water Hydrocarbon can not be adsorbed in resin surface, and water plays the buffer action between resin and reactant, prevents oligomerisation reaction Occur.Furthermore, while C 5 fraction has certain solubility in water, but since no discharge of wastewater, material do not lose.
For C 5 fraction selective hydrogenation and removing pentone process, inventor has found, is handled using sulfurization QSH-06 catalyst can obtain preferable hydrogenation selectivity, and key is adsorptive selectivity of the catalyst to alkynes, theoretically To speculate, all in catalyst surface chemisorbed can occur for isoprene and pentone, and then with adsorbing in catalyst surface Hydrogen atom carry out addition reaction, although therefore there is a small amount of isoprene to be hydrogenated with, since pentone is inhaled in catalyst table Attached ability is stronger, and pentone is much larger than isoprene in the concentration of catalyst surface so that hydrogenation reaction is added with pentone Based on hydrogen, it is achieved thereby that removing the purpose of alkynes via selective hydrogenation.Hydrogenation preferably uses bubbling bed reactor to carry out, its Hydrogenation selectivity is compared with three phase trickle flow bed advantageously.
After making choice property hydrogenation, in the C 5 fraction of hydrogenation, the content of pentone be typically reduced to 15mg/kg with Under, isoprene content is about 97%, is a kind of quality raw materials for producing polymerization grade isoprene, it is new with light dydrocarbon device After fresh light dydrocarbon raw material mixing, the content of isoprene in raw material can be improved, the operating severity of process units is reduced, reduces Energy consumption, and can further reduce the pentone content in isoprene product, be conducive to continue to improve polymer grade isoamyl two The product quality of alkene.
Compared with prior art, the beneficial effects of the present invention are：
(1) C 5 fraction is subjected to removing diformazan by the fixed bed formed equipped with sulfonic group cation exchange resin/water Amine, selective hydrogenation catalyst sulfurization is handled, and the C5 fraction after denitrogenation passes through equipped with Pd/Al2O3The bubbling bed of catalyst Reactor making choice property hydrogenation reaction, C 5 fraction is a kind of quality raw materials for producing isoprene after hydrogenation；
(2) QSH-06 selective hydrogenation catalysts sulfurization is handled, is conducive to improve the hydrogenation selectivity of pentone, Reduce the loss of isoprene；
(2) present invention process is easy to operate, non-wastewater discharge, denitrogenation precision are high, can effectively prevent polymerization side reactions, and Hydrogenation selectivity is high, and isoprene loss is less；
(3) after the C 5 fraction after hydrogenation is mixed with the fresh light dydrocarbon raw material of light dydrocarbon device, isoamyl in raw material can be improved The content of diene, reduces the operating severity of process units, reduces energy consumption, and can further reduce in isoprene product Pentone content, be conducive to continue to improve polymerization grade isoprene product quality.
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 uses derives from light dydrocarbon separator when producing isoprene, and the one of extraction Partial material.The component of C 5 fraction is shown in Table 1.
1. C5 fraction of table forms
Component C 5 fraction
Total carbon four, % 0.02
3- methyl butenes -1, % 0.01
1.4- pentadienes, % 0.02
2- butine, % 0.17
Pentone, % 2.25
2- methyl butenes -1, % 0.02
Isoprene, % 96.56
2- methyl butenes -2, % 0.06
Cyclopentadiene, % 0.00
Cyclopentene, % 0.00
Other light dydrocarbons, % 0.00
Dimethylamine, % 0.35
pH 10
2nd, C 5 fraction takes off dimethylamine
C 5 fraction takes off dimethylamineStainless steel tube in carry out, filled in pipe Enter 100 grams of composition resin beds of spherical sulfonic group cation exchange resin catalyst that particle diameter is 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 controlled by feed pump, and system pressure returns to the back pressure valve regulation of material storage tank by being installed on after washing.Testing Before beginning, it will be disengaged from sub- water and be filled with water scrubber, until the liquid level of water reaches the 20~30mm for being higher by resin bed height.Start Water-circulating pump, deionized water from top to bottom flow through resin bed, after stablizing, start and return to material feed pump, oil phase returns Adverse current enters resin bed to material from the bottom to top.Oil phase flows out after sedimentation divides water at the top of water scrubber.Deionized water is expected with returning Mass ratio be 0.01:1.1~0.01:1.5, mass space velocity is 5~20hr-1；Reaction temperature is 10~55 DEG C；Reaction pressure is 0.2~0.6MPa.The content of dimethylamine can be obtained by the measure of basicity before and after washing, and the measure of basicity uses SH/ Dimethylamine determination method in T0162-1992 oil products.The condition of implementation 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, catalyst member poisoning and denitrogenation after C 5 fraction selective hydrogenation
Pb series catalysts sulfurization carries out within the hydrogenation reaction phase, and stainless steel tubular type reactor size is Load the spherical Pd/Al that particle diameter is 3~5mm in pipe2O3100 grams of composition catalyst beds of catalyst.Catalyst Pd's Mass fraction is 0.28~0.3%, and the specific surface area of alumina catalyst support is 100~300m2/ g, pore volume are 0.1~0.6ml/ g.Vulcanizing treatment carries out under inert media, adds at least one sulfur-containing compound, and condition is controlled in 0.1~0.5MPa pressure Under, for temperature in room temperature~100 DEG C, mass space velocity is 5~50hr-1, when vulcanization time is 1~48 small, partial vulcanization poisoning is made The selective hydrogenation catalyst of processing.
The selective hydrogenation of C 5 fraction carries out in bubbling bed after denitrogenation.C 5 fraction pentone and hydrogen Molar ratio is 1: 1~1：4.0.LHSV is 10~40hr-1, system pressure is 0.8~1.5MPa, and reaction temperature is 30~70 DEG C, Reaction feed amount is controlled by feed pump, and system pressure is by being installed on the back pressure valve regulation of high score tank.
Hydrogenation reactor is sent into by top with the speed set with pump after C 5 fraction is preheated after denitrogenation, hydrogen passes through gas Body distributor enters in reactor, and C 5 fraction material enters catalyst bed after being mixed with hydrogen and carries out hydrogenation reaction.Hydrogenation Material enters a gas-liquid separator by hydrogenation reactor bottom, and liquid phase material enters product storage tank.Separated by gas-liquid separator Emptied after entering wet-test meter metering after the adjusted valve decompression of unreacting hydrogen, or Returning reacting system after compression.Hydrogenated products Analyzed by gas-chromatography.The reaction condition and hydrogenation of each embodiment the results are shown in Table 4.
Table 4.

Claims (7)

  1. A kind of 1. removal methods of pentone in C 5 fraction, it is characterised in that after C5 fraction is carried out denitrogenation processing, then Hydrogenation is selected under the action of the Pd series catalysts QSH-06 of partial vulcanization, realizes the removing of pentone in C5 fraction.
  2. 2. removal methods according to claim 1, it is characterised in that by equipped with sulfonic group cation exchange resin/water The fixed bed of composition carries out denitrogenation processing to C5 fraction.
  3. 3. removal methods according to claim 2, it is characterised in that denitrification temperature is 10~55 DEG C, mass space velocity for 5~ 20hr-1, system pressure is 0.1~0.6MPa, and the mass ratio of water and C 5 fraction is 0.01:1~0.01:2.
  4. 4. the removal methods according to right wants 1, it is characterised in that the Pd series catalysts QSH-06 of partial vulcanization is urged by Pd systems Agent QSH-06 and sulfur-containing compound reaction obtain, wherein：System pressure is 0.1~0.5MPa, and reaction temperature is in room temperature~100 Between DEG C, when the reaction time is 1~48 small, mass space velocity is 5~50hr-1。
  5. 5. removal methods according to claim 4, it is characterised in that sulfur-containing compound is selected from H2S, methyl sulfide, ethyl sulfide, Any one in methyl mercaptan or ethyl mercaptan.
  6. 6. removal methods according to claim 1, it is characterised in that selection hydrogenation carries out in bubbling bed reactor.
  7. 7. removal methods according to claim 1, it is characterised in that selection hydrogenation technique for：LHSV is 10~25hr-1, System pressure is 0.8~1.5MPa, and reaction temperature is 40~60 DEG C, and the molar ratio of pentone and hydrogen is 1 in C 5 fraction: 1~1：3.0.
CN201610963467.5A 2016-10-28 2016-10-28 The removal methods of pentone in C5 fraction Pending CN108017500A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN111100242A (en) * 2018-10-25 2020-05-05 中国石油化工股份有限公司 Dicyclopentadiene hydrogenated petroleum resin and preparation method thereof
CN111100243A (en) * 2018-10-25 2020-05-05 中国石油化工股份有限公司 Modified carbon-acanthopanax hydrogen petroleum resin and preparation method thereof
CN111440045A (en) * 2020-04-20 2020-07-24 浙江大学衢州研究院 Separation method of carbon-pentaene mixture

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Publication number Priority date Publication date Assignee Title
CN1412165A (en) * 2001-10-12 2003-04-23 中国石油化工股份有限公司 Separation method of cracked C5 fraction
CN1472284A (en) * 2002-07-30 2004-02-04 中国石油化工股份有限公司 Method for separating and refining etherification material from catalytic cracking gasoline
CN103086822A (en) * 2011-11-02 2013-05-08 中国石油化工股份有限公司 Separation method of piperylene
CN104058915A (en) * 2013-03-20 2014-09-24 中国石油化工股份有限公司 Method for separating cracking C5 fraction through hydrogenation distillation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1412165A (en) * 2001-10-12 2003-04-23 中国石油化工股份有限公司 Separation method of cracked C5 fraction
CN1472284A (en) * 2002-07-30 2004-02-04 中国石油化工股份有限公司 Method for separating and refining etherification material from catalytic cracking gasoline
CN103086822A (en) * 2011-11-02 2013-05-08 中国石油化工股份有限公司 Separation method of piperylene
CN104058915A (en) * 2013-03-20 2014-09-24 中国石油化工股份有限公司 Method for separating cracking C5 fraction through hydrogenation distillation

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN111100242A (en) * 2018-10-25 2020-05-05 中国石油化工股份有限公司 Dicyclopentadiene hydrogenated petroleum resin and preparation method thereof
CN111100243A (en) * 2018-10-25 2020-05-05 中国石油化工股份有限公司 Modified carbon-acanthopanax hydrogen petroleum resin and preparation method thereof
CN111440045A (en) * 2020-04-20 2020-07-24 浙江大学衢州研究院 Separation method of carbon-pentaene mixture
CN111440045B (en) * 2020-04-20 2022-12-13 浙江大学衢州研究院 Separation method of carbon-pentaene mixture

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Application publication date: 20180511