CN101555197B - Comprehensive use method of mixed C-4 - Google Patents
Comprehensive use method of mixed C-4 Download PDFInfo
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- CN101555197B CN101555197B CN2008100432508A CN200810043250A CN101555197B CN 101555197 B CN101555197 B CN 101555197B CN 2008100432508 A CN2008100432508 A CN 2008100432508A CN 200810043250 A CN200810043250 A CN 200810043250A CN 101555197 B CN101555197 B CN 101555197B
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Abstract
The invention relates to a comprehensive use method of mixed C-4, which mainly aims at solving the problem that the comprehensive utilization ratio of mixed C-4 by-products generated by a steam cracking device and an FCC device is low in the prior art. The method comprises the following steps: (1) adopting an extract technology to obtain butadiene through separation; (2) adopting an etherificationtechnology to synthesize MTBE by using isobutene remained in the C-4 undergoing the extraction in the first step; (3) separating water, ether and alcohol in the C-4 undergoing the etherification in t he second step by adopting a refining and separating technology; (4) producing propylene through the disproportionating reaction between the mixed C-4 which is purified in the third step and ethylene by adopting an olefine disproportionation technology; and (5) cyclically taking the mixed C-4 which is left after the reaction in the fourth step as the raw material of a cracking furnace. Such a technical scheme better solves the problem and can be used in the industrial production for increasing the propylene production and the comprehensive value of the mixed C-4.
Description
Technical field
The present invention relates to a kind of method of comprehensive utilization of mixed c 4.
Background technology
The present invention relates to the by-product C that a kind of mixed c 4 means steam cracking device
4The by-product C of cut and catalytic cracking unit
4Cut, the mixed c 4 of steam cracking device by-product generally utilizes iso-butylene through extracting divinyl, MTBE device at present, although last remaining mixed c 4 contains a large amount of butene-1s and butene-2, most of as the liquefied gas use at present, part is produced house can the separating-purifying butene-1.And the mixed C of catalytic cracking unit by-product
4Basically use as liquefied gas.Therefore, most mixed c 4 does not all take full advantage of their chemical industry added value, and comprehensive utilization ratio is extremely low.In recent years, how to fully utilize the research of mixed c 4 very many.
To obtain divinyl be present more common one of method of utilizing to extracting and separating from mixed c 4, adopts extraction agent the butadiene extraction in the mixed c 4 out, the butane that extraction tower (1) cat head distillates, butene mixture recycling after washing.And still liquid is divinyl, a small amount of alkynes and acetonitrile solution at the bottom of the extraction tower tower, separates by a rectifying tower (2).Rectifying tower (2) cat head obtains divinyl and alkynes, separates alkynes by another one rectifying tower (3), and obtains product butadiene.Still liquid is acetonitrile at the bottom of rectifying tower (2) tower, enters extraction tower (1) and recycle after cooling.
The method of utilizing that another one is commonly used is the synthetic MTBE of iso-butylene that utilizes in the mixed c 4, and C 4 mixture and methyl alcohol are mixed in proportion, and enter methyltertiarvbutyl ether reactor and react.Reaction product is separated by a rectifying tower, and cat head obtains unreacted carbon four and methyl alcohol, obtains the MTBE product at the bottom of the tower.The unreacted carbon four that cat head obtains obtains respectively unreacted carbon four and methyl alcohol with the azeotrope of methyl alcohol behind eparating methanol tower and methanol distillation column, unreacted carbon four recyclings, and methanol loop is sent to reactor.
Utilizing mixed c 4 to produce propylene is to have one of solution than hi-tech economy.Propylene is one of important basic organic chemical industry raw material.Propylene is mainly for the production of all multi-products such as polypropylene, isopropyl benzene, propylene oxide, vinyl cyanide, vinylformic acid.As important light olefin, propylene year demand in continuous growth.But the general overview of the technique of producing propylene is byproduct technique and proprietary technique.Byproduct technique mainly refers to the propylene that obtains by steam cracking and catalytic cracking ethylene unit processed.Proprietary technique refers to the technique of special Development and Production propylene, mainly contains at present the Technologies such as dehydrogenating propane.Utilize mixed c 4 to produce propylene, not only improved mixed c 4 chemical industry added value, also satisfied to a certain extent the demand of market to propylene.
Document WO 03078364 has been introduced the method that a kind of mixed c 4 or carbon five are converted into propylene.This technique is divided into two large steps, and step 1 is first oligomeric mixed olefins, then oligopolymer is carried out cracking and generates propylene.This method side reaction is many, and the product of generation is complicated, and the selectivity of propylene is not high, and the purification difficulty is large.Simultaneously, this technique is not mentioned the utilization of the higher composition of added value in the mixed c 4 such as divinyl, iso-butylene.
Document CA2297301 has introduced a kind of method that improves carbon four and carbon four above mixtures value.This method is feedstock conversion low-carbon alkene directly by adopting zeolite molecular sieve, and separation obtains propylene, ethene.But this technique subsequent separation process contains two catalytic pyrolysis unit, a selective hydrogenation unit, an etherificate unit, and flow process is complicated, and the propylene and ethylene yield is not high, and Technical Economy is relatively poor.
The described technique of above-mentioned document all is to the utilization of mixed c 4 or carbon five, relates to olefin cracking, produces propylene and ethylene.But all the higher composition of added value in the mixed c 4 such as divinyl, iso-butylene are not carried out extraction and application, the residue butane does not have further chemical utilization, and the comprehensive economy of mixed c 4 does not find full expression.
Summary of the invention
Technical problem to be solved by this invention is steam cracking device by-product mixed c 4 and the not high problem of FCC apparatus by-product mixed c 4 comprehensive utilization ratio in the conventional art, and a kind of new mixed c 4 method of comprehensive utilization is provided.The method has and adopts extractive distillation technology, etherification technology, isomerization of butene technology, olefin metathesis technology that mixed c 4 is fully utilized, and separates the advantage that obtains divinyl, iso-butylene, pyrolyzer raw material and generate propylene.
In order to solve the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of method of comprehensive utilization of mixed c 4 may further comprise the steps:
(1) the liquid phase feed mixed c 4 enters extraction tower, and by the extraction agent extractive distillation, the extraction tower cat head obtains containing the mixture stream passes 1 of butylene, butane, enters the etherificate unit; The extraction tower tower reactor obtains containing the mixture stream passes 2 of divinyl, extraction agent, obtains butadiene stream 3 through further separating;
(2) in the etherificate unit, MTBE is produced in the iso-butylene in the logistics 1 and methyl alcohol reaction; The etherification reaction product is isolated to MTBE product and residue mixed c 4 logistics 4;
(3) by refining isolation technique, isolate water, ether and alcohol in the logistics 4, the mixed c 4 logistics 5 after purifying enters the butylene disproportionation unit;
(4) in the disproportionation unit, the butene-2 in the logistics 5 and ethene carry out disproportionation reaction, generate propylene; The disproportionation reaction product is isolated to propylene product, unreacting ethylene and unreacted mixed c 4 logistics 6.
In the technique scheme, liquid-phase mixing carbon four preferred versions are the middle part that enters extraction tower, and the extraction agent preferred version is the top that enters extraction tower; The extraction agent preferred version is acetonitrile or dimethyl formamide; The extraction tower preferred version is sieve-tray tower, valve tray column or packing tower, and cat head working pressure preferable range is 0.38～0.65MPa; The catalyzer preferred version that etherification reaction adopts is large hole cation exchanger resin, and the temperature of reaction preferable range is 25～80 ℃, and the reaction pressure preferable range is 0.8～2.0MPa, and the reaction velocity preferable range is 1～30 hour
-1Disproportionation reactor preferable range in the disproportionation unit is for dividing two sections, and the epimere preferred version is the filling isomerization catalyst, and the hypomere preferred version is the filling disproportionation catalyst; Lower section catalyst is 1～10: 1 with the epimere catalyst weight than preferable range; Butene-1 preferred version in the logistics 5 turns to butene-2 for first isomery in disproportionation reactor; The unreacting ethylene preferred version enters disproportionation reactor for circulation; Disproportionation reactor epimere catalyzer preferred version is metal oxide or strongly-acid molecular sieve, and the lower section catalyst preferred version is metal oxide; Disproportionation reaction temperature preferable range is 260～330 ℃, and the reaction pressure preferable range is 2.0～3.5MPa, and the reaction velocity preferable range is 5～20 hours
-1Logistics 6 circulations enter steam cracking device as the cracking stock of pyrolyzer.
The inventive method adopts comprehensive utilization extractive distillation technology, etherification technology, isomerization of butene technology and butylene disproportionation technology, take full advantage of the higher component of added value in the mixed c 4, not only directly obtain higher divinyl, the reaction of chemical industry added value and generated MTBE, propylene, also obtained preferably pyrolyzer cracking stock.Utilize the inventive method, above above iso-butylene, the acquisition 25% (weight of divinyl, 92% (weight) of 95% (weight) in the recyclable mixed c 4, for the raw material mixed c 4) above propylene and the pyrolyzer cracking stock that obtains 10～30% (weight is for the raw material mixed c 4s).Therefore, the inventive method has greatly improved the value of mixed c 4, has obtained preferably technique effect.
Description of drawings
Fig. 1 is the inventive method process flow diagram.
Fig. 2 is document CA2297301 process flow diagram.
Fig. 3 is document WO 03078364 process flow diagram.
Fig. 1, A is methyl alcohol among Fig. 2 or Fig. 3, and B is light boiling point polar material, and C is the high boiling point polar material, D is refining separating unit, and 1 is the raw material mixed c 4, and 2 is extraction agent, 3 is MTBE, and 4 is divinyl, extractant mixture, 5 is fresh ethylene, 6 is cyclic ethylene, and 7 is disproportionation reactor, and 8 is the disproportionation products separating unit, 9 is propylene, 10 is the unreacted mixed c 4, and 11 are the circulation mixed c 4, and 12 is the extractive distillation tower, 13 is the etherificate unit, 14 is the first catalytic cracking reaction device, and 15 is the second catalytic cracking reaction device, and 16 is the first rectifying tower, 17 is the selective hydrogenation device, 18 is methyltertiarvbutyl ether reactor, and 19 is Second distillation column, and 20 is light constituent (CH
4Deng), 21 is the ethene cut, and 22 is the propylene cut, and 23 is C 4 mixture, 24 components of attaching most importance to, 25 is methyl alcohol, and 30 is oligomerization reactor, and 31 is oligomerization product, and 32 is the catalytic pyrolysis product, 33 is C
3Following cut, 34 is rectifying tower, 35 is C
5Above cut, 36 are the circulation mixed c 4.
Among Fig. 1, through the extraction agent extracting and separating out, tower 12 tops distillate butylene, butane mixture to mixed c 41, enter etherificate unit 13 in extractive distillation tower 12; The bottom is divinyl, extractant mixture.Through the etherificate unit, iso-butylene and methyl alcohol reaction generate MTBE; Residual carbon four after the etherificate enters refining separating unit D, and isolates light boiling point polar material B and high boiling point polar material C; Through the mixed c 4 behind the refining separating-purifying with enter disproportionation reactor 7 after ethene (5+6) mixes and carry out isomerization reaction and disproportionation reaction, product obtains by separating unit 8 separation: unreacting ethylene 6, propylene 9, unreacted mixed c 4 10, circulation mixed c 4 11.Unreacting ethylene 6 circulations are as reaction raw materials, and unreacted mixed c 4 10 is delivered to steam cracking device as cracking stock.
Embodiment
[comparative example 1]
By shown in Figure 2, mixed c 4 forms (% by weight) and is: divinyl: 40.0%, and iso-butylene: 12.0%, butene-1: 18.0%, butene-2: 18.2%, butane: 11.8%.Adopt document CA2297301 technical process, catalytic cracking catalyst employing silica alumina ratio is 300 Si-Al molecular sieve, and the temperature of reaction of the first catalytic cracking reaction device and the second catalytic cracking reaction device is 500 ℃, and reaction pressure is 0.3MPa; The first rectifying tower 16 is valve tray column, and stage number is 110, and tower top pressure is 0.8MPa; Selective hydrogenation catalyst is the palladium metal series catalysts, and temperature of reaction is 110, and reaction pressure is 3.0MPa; Catalyst for etherification is ion exchange resin, and temperature of reaction is 30 ℃, and reaction pressure is 1.5MPa; Second distillation column 19 is sieve-tray tower, and stage number is 60, and tower top pressure is 0.4MPa.Experimental results show that acquisition propylene and ethene are respectively 13% and 3% (weight is for raw material mixed c 4 1).
[comparative example 2]
By shown in Figure 3, mixed c 4 forms (% by weight) and is: divinyl: 40.0%, and iso-butylene: 12.0%, butene-1: 18.0%, butene-2: 18.2%, butane: 11.8%.Adopt document WO 03078364 technical process, olefin oligomerization catalyst adopts solid phosphoric acid, and temperature of reaction is 180 ℃, and reaction pressure is 5.0MPa; Catalytic cracking catalyst adopts the small-bore zeolite molecular sieve, and temperature of reaction is 550 ℃, and reaction pressure is 0.15MPa; Rectifying tower 34 is valve tray column, and stage number is 80, and tower top pressure is 0.5MPa.Experimental results show that and to obtain propylene and ethene is respectively 8.1% and 1.8% (weight is for raw material mixed c 4 1).
[embodiment 1]
By shown in Figure 1, mixed c 4 forms (% by weight) and is: divinyl: 40.0%, and iso-butylene: 12.0%, butene-1: 18.0%, butene-2: 18.2%, butane: 11.8%.Adopt technical process of the present invention, extraction agent 2 adopts acetonitrile; Introduce such as background technology, the extractive distillation butadiene unit comprises extraction tower, water wash column, rectifying tower (2) and rectifying tower (3).Extraction tower is valve tray column, and stage number is 60, and the cat head working pressure is 0.45MPa; Water wash column is valve tray column, and stage number is 50, and the cat head working pressure is 0.6MPa; Rectifying tower (2) is valve tray column, and stage number is 40, and the cat head working pressure is 0.5MPa; Rectifying tower (3) is valve tray column, and stage number is 60, and the cat head working pressure is 0.8MPa.The etherificate unit comprises methyltertiarvbutyl ether reactor, rectifying tower, eparating methanol tower and a methanol distillation column.The catalyzer of methyltertiarvbutyl ether reactor filling is macropore H ion exchange resin, and temperature of reaction is 60 ℃, and reaction pressure is 1.3MPa, and reaction velocity is 8 hours
-1Rectifying tower is valve tray column, and stage number is 40, and the cat head working pressure is 0.5MPa; Eparating methanol tower is sieve-tray tower, and stage number is 30, and the cat head working pressure is 0.2MPa; Methanol distillation column is valve tray column, and stage number is 30, and the cat head working pressure is 0.2MPa.Disproportionation reactor 7 epimere catalyst loading magnesium oxide, lower section catalyst filling Tungsten oxide 99.999; Lower section catalyst is 6: 1 with epimere catalyst weight ratio; Temperature of reaction is 280 ℃, and reaction pressure is 3.2MPa, and reaction velocity is 8 hours
-1Experimental installation proves recyclable 98% divinyl, 95% iso-butylene, and obtaining simultaneously propylene is the pyrolyzer cracking stock of 27.3% (weight is for raw material mixed c 4 1) and 15% (weight is for raw material mixed c 4 1).
[embodiment 2]
By shown in Figure 1, mixed c 4 forms (% by weight) and is: divinyl: 30.0%, and iso-butylene: 12.0%, butylene--1:18.0%, butene-2: 18.2%, butane: 21.8%.Adopt technical process of the present invention, extraction agent 2 adopts dimethyl formamide; Introduce such as background technology, the extractive distillation butadiene unit comprises extraction tower, water wash column, rectifying tower (2) and rectifying tower (3).Extraction tower is sieve-tray tower, and stage number is 80, and the cat head working pressure is 0.65MPa; Water wash column is sieve-tray tower, and stage number is 60, and the cat head working pressure is 0.4MPa; Rectifying tower (2) is sieve-tray tower, and stage number is 50, and the cat head working pressure is 0.6MPa; Rectifying tower (3) is sieve-tray tower, and stage number is 80, and the cat head working pressure is 0.6MPa.The etherificate unit comprises methyltertiarvbutyl ether reactor, rectifying tower, eparating methanol tower and a methanol distillation column.The catalyzer of methyltertiarvbutyl ether reactor filling is macropore P ion exchange resin, and temperature of reaction is 40 ℃, and reaction pressure is 1.1MPa, and reaction velocity is 10 hours
-1Rectifying tower is sieve-tray tower, and stage number is 50, and the cat head working pressure is 0.6MPa; Eparating methanol tower is valve tray column, and stage number is 25, and the cat head working pressure is 0.3MPa; Methanol distillation column is valve tray column, and stage number is 30, and the cat head working pressure is 0.2MPa.Disproportionation reactor 7 epimere catalyst loading silicon sol, lower section catalyst filling Tungsten oxide 99.999; Lower section catalyst is 2: 1 with epimere catalyst weight ratio; Temperature of reaction is 300 ℃, and reaction pressure is 2.8MPa, and reaction velocity is 5 hours
-1Experimental installation proves recyclable 99% divinyl, 92% iso-butylene, and obtaining simultaneously propylene is the pyrolyzer cracking stock of 30.5% (weight is for raw material mixed c 4 1) and 22% (weight is for raw material mixed c 4 1).
[embodiment 3]
By shown in Figure 1, mixed c 4 forms (% by weight) and is: divinyl: 20.0%, and iso-butylene: 15.0%, butene-1: 18.0%, butene-2: 18.2%, butane: 28.8%.Adopt technical process of the present invention, extraction agent 2 adopts acetonitrile; Introduce such as background technology, the extractive distillation butadiene unit comprises extraction tower, water wash column, rectifying tower (2) and rectifying tower (3).Extraction tower is packing tower, and packed height is 30 meters, and the cat head working pressure is 0.55MPa; Water wash column is packing tower, and packed height is 20, and the cat head working pressure is 0.5MPa; Rectifying tower (2) is valve tray column, and stage number is 43, and the cat head working pressure is 0.55MPa; Rectifying tower (3) is packing tower, 22 meters of packed heights, and the cat head working pressure is 0.4MPa.The etherificate unit comprises methyltertiarvbutyl ether reactor, rectifying tower, eparating methanol tower and a methanol distillation column.The catalyzer of methyltertiarvbutyl ether reactor filling is macropore P ion exchange resin, and temperature of reaction is 80 ℃, and reaction pressure is 1.5MPa, and reaction velocity is 20 hours
-1Rectifying tower is valve tray column, and stage number is 40, and the cat head working pressure is 0.4MPa; Eparating methanol tower is packing tower, and packed height is 10 meters, and the cat head working pressure is 0.3MPa; Methanol distillation column is packing tower, and packed height is 12 meters, and the cat head working pressure is 0.1MPa.Disproportionation reactor 7 epimere catalyst loading magnesium oxide, lower section catalyst filling Tungsten oxide 99.999; Lower section catalyst is 8: 1 with epimere catalyst weight ratio; Temperature of reaction is 330 ℃, and reaction pressure is 3.5MPa, and reaction velocity is 15 hours
-1Experimental installation proves recyclable 95% divinyl, 96% iso-butylene, and obtaining simultaneously propylene is the pyrolyzer cracking stock of 25.1% (weight is for raw material mixed c 4 1) and 28% (weight is for raw material mixed c 4 1).
Claims (5)
1. the method for comprehensive utilization of a mixed c 4 may further comprise the steps:
(1) the liquid phase feed mixed c 4 enters extraction tower, and by the extraction agent extractive distillation, the extraction tower cat head obtains containing the mixture stream passes 1 of butylene, butane, enters the etherificate unit; The extraction tower tower reactor obtains containing the mixture stream passes 2 of divinyl, extraction agent, obtains butadiene stream 3 through further separating;
(2) in the etherificate unit, methyl tertiary butyl ether (MTBE) is produced in the iso-butylene in the logistics 1 and methyl alcohol reaction; The etherification reaction product is isolated to methyl tertiary butyl ether (MTBE) product and residue mixed c 4 logistics 4;
(3) by refining isolation technique, isolate water, ether and alcohol in the logistics 4, the mixed c 4 logistics 5 after purifying enters the butylene disproportionation unit;
(4) in the disproportionation unit, the butene-2 in the logistics 5 and ethene carry out disproportionation reaction, generate propylene; The disproportionation reaction product is isolated to propylene product, unreacting ethylene and unreacted mixed c 4 logistics 6; Disproportionation reactor in the disproportionation unit divides two sections, epimere filling isomerization catalyst, and hypomere filling disproportionation catalyst, lower section catalyst is 1～10: 1 with epimere catalyst weight ratio; Butene-1 in the logistics 5 first isomery in disproportionation reactor turns to butene-2;
Wherein, liquid-phase mixing carbon four enters the middle part of extraction tower, and extraction agent enters the top of extraction tower; Extraction agent is dimethyl formamide; Extraction tower is sieve-tray tower, valve tray column or packing tower, and the cat head working pressure is 0.38～0.65MPa; The catalyzer that etherification reaction adopts is large hole cation exchanger resin, and temperature of reaction is 25～80 ℃, and reaction pressure is 0.8～2.0MPa, and reaction velocity is 1～30 hour
-1
2. the method for comprehensive utilization of described mixed c 4 according to claim 1 is characterized in that the unreacting ethylene circulation enters the disproportionation reactor in the disproportionation unit.
3. the method for comprehensive utilization of described mixed c 4 according to claim 2 is characterized in that disproportionation reactor epimere catalyzer is metal oxide or strongly-acid molecular sieve, and lower section catalyst is metal oxide.
4. the method for comprehensive utilization of described mixed c 4 according to claim 1 is characterized in that the disproportionation reaction temperature is 260～330 ℃, and reaction pressure is 2.0～3.5MPa, and reaction velocity is 5～20 hours
-1
5. the method for comprehensive utilization of described mixed c 4 according to claim 1 is characterized in that unreacted mixed c 4 logistics 6 circulations enter steam cracking device as the cracking stock of pyrolyzer.
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| CN102285854B (en) * | 2010-06-18 | 2013-11-06 | 中国石油化工股份有限公司 | Method for increasing yields of propylene, ethylene and butadiene |
| CN102372608A (en) * | 2010-08-19 | 2012-03-14 | 中国石油化工股份有限公司 | Mixed C4 utilization method |
| US8822710B2 (en) * | 2011-10-17 | 2014-09-02 | Shell Oil Company | Process for preparing an epoxide from an oxygenate |
| CN104030872B (en) * | 2013-03-04 | 2016-01-13 | 中国石化工程建设有限公司 | A kind of method improving acetonitrile method 1,3-butadiene extraction plant raffinate product yield |
| US20140296587A1 (en) * | 2013-03-28 | 2014-10-02 | Uop Llc | Integrated Process for Increasing Butadiene Production |
| CN105859530B (en) * | 2015-01-23 | 2018-04-06 | 上海优华系统集成技术有限公司 | A kind of stabilizer and MTBE device catalytic rectifying tower combined cycle equipment |
| RU2017132466A (en) * | 2015-02-19 | 2019-03-19 | Сабик Глобал Текнолоджиз Б.В. | SYSTEMS AND METHODS RELATED TO THE PRODUCTION OF METHYL-THR-BUTYL ETHER |
| CN106365947B (en) * | 2015-07-22 | 2019-08-02 | 中国石油天然气股份有限公司 | A kind of plug oils lighter hydrocarbons method for transformation |
| CN106365941B (en) * | 2015-07-22 | 2019-09-03 | 中国石油天然气股份有限公司 | A kind of conversion process of lower carbon number hydrocarbons |
| CN106365942B (en) * | 2015-07-22 | 2020-02-14 | 中国石油天然气股份有限公司 | Mixed C4 conversion method |
| CN106866337B (en) * | 2015-12-14 | 2019-12-10 | 中国石油天然气股份有限公司 | Conversion and utilization process of mixed C4 |
| US11124470B2 (en) | 2017-04-03 | 2021-09-21 | Sabic Global Technologies B.V. | Systems and methods of producing methyl tertiary butyl ether and propylene |
| CN111132956B (en) | 2017-07-19 | 2023-04-25 | 沙特基础工业全球技术公司 | Use of MTBE raffinate in propylene production |
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| US5300718A (en) * | 1988-09-19 | 1994-04-05 | Lyondell Petrochemical Company | Olefin conversion process |
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| US5300718A (en) * | 1988-09-19 | 1994-04-05 | Lyondell Petrochemical Company | Olefin conversion process |
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