CN104250193B - A kind of propylene and the preparation method of butadiene - Google Patents
A kind of propylene and the preparation method of butadiene Download PDFInfo
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- propylene
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Abstract
The invention discloses the preparation method of a kind of propylene and butadiene, the method comprises the following steps: (1) isolates normal butane and n-butene from liquefied petroleum gas；(2) step (1) isolated normal butane and n-butene are carried out steam cracking reaction respectively, or the mixture of described normal butane and n-butene is carried out steam cracking reaction.The method using the present invention to provide is obtained in that higher propylene and butadiene yield.
Description
Technical field
The present invention relates to the preparation method of a kind of propylene and butadiene.
Background technology
Propylene is the important Organic Chemicals being only second to ethylene, multiple important organic for producing
Industrial chemicals, synthetic resin, synthetic rubber and multiple fine chemicals etc., mainly include poly-third
Alkene, acrylonitrile, acrylic acid, isopropyl alkene, acetone, expoxy propane etc., be widely used in national economy each
Individual field.At present, the main mode of production of propylene has three kinds: steam cracking process, refinery catalytic cracking
Technique and dehydrogenating propane technique.Wherein, propylene is mainly derived from steam cracking process, and its yield reaches
To more than the 65% of propylene total output, it is secondly refinery catalytic cracking technique, and dehydrogenating propane technique
Commercial Application less.In recent years, due to the fast development of propylene downstream product, it is greatly promoted
The China's quick growth to propylene demand.Anticipated 2015, the production capacity of China's propylene can reach
To 24,000,000 tons, yield reaches 21,600,000 tons, the demand gap dependence on import solution of about 6,400,000 tons
Certainly.Therefore, China's propylene develops and has broad prospects.
Butadiene is often referred to 1,3-butadiene (also known as ethylene vinyl), for being only second to ethylene and propylene
Important basic petrochemical raw material.Butadiene is mainly used in synthetic rubber and resin, such as polybutadiene rubber
(BR), butadiene-styrene rubber (SBR), nitrile rubber (NBR), styrene-butadiene polymer latex, styrene heat
Thermoplastic elastic (SBC) and acrylonitrile-butadiene-styrene (ABS) (ABS) resin etc..Additionally, fourth
Diene can be additionally used in the Organic chemical products such as production adiponitrile, hexamethylene diamine, nylon-66, BDO,
It is widely used in numerous areas.
The industrial process of butadiene successively experienced by alcohol dehydrogenase method, butylene catalytic dehydrogenation methods, butane
Catalytic dehydrogenation methods, butylene oxidation-dehydrogenation method, ethylene by-product C 4 fraction partition method.At present, butadiene is former
The source of material mainly has two kinds, the mixing C 4 fraction of ethylene cracker by-product and oil plant C 4 fraction.
In the butadiene production in the whole world, 92% comes from ethylene by-product C 4 fraction partition method, and 8% comes from positive fourth
Alkane and the dehydrogenating technology of n-butene.
At present, on butadiene Downstream Market, the demand of rubber and ABS resin is continuing to increase, butadiene
Consumption figure with average annual about 10% speed increment, and production capacity expansion rate of increase less than 8%, butadiene
Produce still in the state that supply falls short of demand.In traditional butadiene preparation technology, steam-cracking process
Traditional raw material mainly based on lighter hydrocarbons, Petroleum, hydrogenation tail oil, but, the fourth two of lighter hydrocarbons steam cracking
Alkene yield is less than 3%, and the butadiene yield of naphtha steam cracking is 3-6%, and hydrogenation tail oil steam splits
The butadiene yield solved is 4-7%.Therefore, the approach with traditional raw material volume increase butadiene is very limited
's.So, constantly expand butadiene production approach, exploitation new raw material and variation route, for ethylene unit
Necessary with butadiene industry.
Along with the maximization of petroleum chemical enterprise's process units scale, the disposal ability of China's single set oil refining apparatus is
Through more than 10,000,000 tons/year, and the ethylene production capacity of matched ethylene unit also reaches
80-120 ten thousand tons/year.The yield of the liquefied petroleum gas (be called for short LPG) that oil refining and ethylene unit produce by
Year improves.At present, the annual production of China's liquefied petroleum gas alreadys more than 10,000,000 tons.Petrochemical industry enterprise of China
The liquefied petroleum gas of industry by-product is mainly used in the production of civil LPG, only has a small amount of for alkylation
Producing gasoline and aromatic hydrocarbons with aromatisation, comprehensive utilization ratio is less than 15%, well below U.S., Japanese and western
Europe more than 50% utilize level, the economic value added causing liquefied petroleum gas resource is low.And along with cleaning
The natural gas consumption of domestic fuel is continuously increased, the dim future that liquefied petroleum gas uses as fuel.Cause
This, make full use of liquefied petroleum gas resource, improves its comprehensive utilization ratio and economic value added becomes raising refining
Change one of important channel of economic benefit of enterprise.
Summary of the invention
The invention aims to overcome the liquefied petroleum gas utilization rate of prior art and economic extra price
Being worth low defect, and provide a kind of method using liquefied petroleum gas to prepare propylene and butadiene, using should
Method is obtained in that higher propylene and butadiene yield.
The invention provides the preparation method of a kind of propylene and butadiene, the method comprises the following steps:
(1) from liquefied petroleum gas, normal butane and n-butene are isolated；
(2) step (1) isolated normal butane and n-butene are carried out steam cracking reaction respectively, or
The mixture of described normal butane Yu n-butene is carried out steam cracking reaction by person.
From the result of embodiment it can be seen that use the yield of propylene that the method for the present invention enables to
Reaching more than 19.74%, the yield of butadiene reaches more than 7.2%, and the total recovery of propylene and butadiene reaches
To more than 28.65%.As can be seen here, use the present invention provide method be obtained in that higher propylene and
Butadiene yield, thus improve utilization rate and the Economic Value Added of liquefied petroleum gas.
Other features and advantages of the present invention will be described in detail in detailed description of the invention part subsequently.
Detailed description of the invention
Hereinafter the detailed description of the invention of the present invention is described in detail.It should be appreciated that this place is retouched
The detailed description of the invention stated is merely to illustrate and explains the present invention, is not limited to the present invention.
Propylene and the preparation method of butadiene that the present invention provides comprise the following steps:
(1) from liquefied petroleum gas, normal butane and n-butene are isolated；
(2) step (1) isolated normal butane and n-butene are carried out steam cracking reaction respectively, or
The mixture of described normal butane Yu n-butene is carried out steam cracking reaction by person.
The component of described liquefied petroleum gas is known to the skilled person, as a rule, and described liquefaction stone
Oil gas mainly contains C4 component, it is also possible to containing a small amount of C3 following components and/or more than C5 component.
Wherein, C3 following components mainly contains propane, additionally may containing a small amount of hydrogen, methane and
C2 component.C4 component mainly contains normal butane, iso-butane, n-butene, additionally may be containing a small amount of
Isobutene. and the butadiene of trace.Wherein, n-butene includes 1-butylene and 2-butylene, and 2-butylene includes
Maleic and anti-butylene.More than C5 component is mainly pentane.According to the difference in source, liquefied petroleum gas
The content of said components there may be bigger difference.
It is particularly well-suited in the described liquefied petroleum gas of the present invention containing iso-butane, normal butane and n-butene；
And on the basis of the total content of described liquefied petroleum gas, the content of described iso-butane can be 5-70mol%,
The content of described normal butane can be 5-70mol%, and the content of described n-butene can be 10-70mol%；
Preferably, on the basis of the total content of described liquefied petroleum gas, the content of described iso-butane is
5-30mol%, the content of described normal butane is 25-60mol%, and the content of described n-butene is
10-60mol%.Additionally, the liquefied petroleum gas used by the present invention is also possible to containing C3 following components, C5
Above component, a small amount of isobutene. and the 1,3-butadiene of trace, with the total content of described liquefied petroleum gas
On the basis of, the content of described C3 following components can be 5-20mol%, containing of described more than C5 component
Amount can be 0.3-3mol%, and the content of isobutene. can be 0.1-0.2mol%, described 1,3-butadiene
Content can be 0.01-0.1mol%.
In the present invention, from liquefied petroleum gas, isolated n-butene includes 1-butylene and 2-butylene.?
In actual production process, the mixture of 1-butylene and 2-butylene can be isolated from liquefied petroleum gas, and
The mixture of this 1-butylene and 2-butylene is carried out steam cracking；Can also first respectively be isolated by 1-butylene and
2-butylene, then carries out steam cracking reaction respectively by 1-butylene and 2-butylene.
The present invention is to isolating the method for normal butane and n-butene from described liquefied petroleum gas the most especially
Ground limits, it is for instance possible to use in conventional distillation, extracting rectifying, adsorbing separation and Chemical Decomposition method
Any one or more separate.
According to a kind of detailed description of the invention of the present invention, when described liquefied petroleum gas contains below C3 group
Point, iso-butane, normal butane, 1-butylene, isobutene., 2-butylene and during more than C5 component, first pass through
Conventional distillation separates C3 following components and more than C4 Component seperation, and more than the C4 component that will obtain
Carry out conventional distillation separation, obtain iso-butane and 1-butylene and the mixture of isobutene. and normal butane with
2-butylene and the mixture of more than C5 component, then the mixture of iso-butane with 1-butylene and isobutene. is entered
The mixture of row conventional distillation isolated 1-butylene and isobutene. and iso-butane；By normal butane and 2-butylene
Conventional distillation isolated normal butane and the mixture of 2-butylene and C5 is carried out with more than C5 component mixture
Above component.Owing to 1-butylene is close with the boiling point of isobutene., normal butane is close with the boiling point of 2-butylene,
Use conventional distillation to separate to be difficult to separate them, in addition it is also necessary to use C 4 fraction fractionation further
And/or extraction fractional distillation separates.
Described C 4 fraction fractionation can be under the conditions of etherification reaction, by 1-butylene and isobutene.
Mixture react with methanol so that isobutene conversion therein is methyl tertiary butyl ether(MTBE) (MTBE), so
After again etherification product is carried out conventional distillation separation, obtain 1-butylene.
Extraction fractional distillation is to utilize the alkene of C4 and alkane relative volatility in extractant to differ greatly
Principle and realize the separation of alkane and alkene.Solvent used in the process of extraction essence is typically
In morpholine, N-Methyl pyrrolidone (NMP) and dimethylformamide (DMF) any one or
Multiple.At present, extraction fractional distillation can be such as Japanese auspicious father-in-law's extraction fractional distillation or Germany Krupp-storehouse
Po Erfa (sees DE3532289A1).
Specifically, Japanese auspicious father-in-law's extraction fractional distillation can use DMF and/or NMP as solvent, adopts
Extracting system generally include two extracting rectifying devices and two rectifying columns, and each extracting rectifying dress
Put and be made up of an extractive distillation column and a solvent recovery tower.C4 component passes through first extracting rectifying
Device removes alkane, and at the first rectifying column, the product obtained is isolated 2-butylene, at Second distillation column
Isolate 1-butylene.Additionally, the second extracting rectifying device is to isolate 1,3-butadiene.Therefore,
If not containing 1,3-butadiene in C4 component to be separated, then the second extracting rectifying device can omit.
The technological parameter of the most each extracting rectifying device and rectifying column is set to as well known to those skilled in the art, at this
Will not be described in great detail.
Your method of Germany Krupp-cooper with n-butene as target product, raw material be etherified after C4 component
Or etherified and precise distillation isolates the C4 component after 1-butylene and iso-butane, the solvent used is
Anhydrous morpholine.Specifically, C4 component is introduced in the extraction solvent distillation column filling solvent, C4 component
In alkane from extraction solvent overhead flow out, and containing alkene extract from extraction solvent distill
Flow out at the bottom of tower tower, and the described extract containing alkene is obtained alkene in solvent recovery tower after recycling design
Hydrocarbon component.The technological parameter of above extraction solvent distillation column and solvent recovery tower is set to people in the art
Member is known, will not be described in great detail at this.
It should be noted that in actual production process, in order to save the cost of separation further, from liquid
In liquefied oil gas, normal butane and the n-butene of isolated can contain a small amount of impurity, if the target of making
Separate the content of product more than 95 weight %.Such as, in example 2, butylene materials at bottom of tower
The flow of middle 1-butylene is 25.46kg/h, accounts for 98.87 weight % of butylene materials at bottom of tower, at this point it is possible to
This material is directly carried out as the raw material containing 1-butylene steam cracking, and without dividing further
From.
The method that the present invention provides also includes isolating propylene and butadiene from steam cracking reaction product.
It should be noted that when described normal butane and n-butene are carried out steam cracking reaction by the present invention respectively,
Obtain two kinds of pyrolysis products, at this point it is possible to again from the mixture obtained after first two kinds of pyrolysis products being mixed
In isolate propylene and butadiene, it is also possible to both pyrolysis products are separated respectively.
According to the present invention, the separation of described steam cracking reaction and pyrolysis product is carried out in cracker.
Described cracker includes pyrolysis furnace and segregation apparatus.Described pyrolysis furnace can be commonly used in the art
Steam cracking propylene and the pyrolysis furnace of butadiene.Described pyrolysis furnace mainly includes convection section, radiation
Section, quenching boiler and gas burning system.In described pyrolysis furnace, respectively by cracking stock be steam heated to
There is steam cracking reaction, generate containing propylene and the cracking gas of butadiene.In the preferred case, described
Pyrolysis furnace is preferably tube cracking furnace.Described tube cracking furnace includes convection section, radiant section, quenching boiler
And gas burning system, cracking stock enters radiant section in convection section；In radiant section, cracking stock and steaming
Vapour is heated to steam cracking reaction, generates containing propylene and the cracking gas of butadiene；Cracking gas is from spoke
The section of penetrating enters quenching boiler the most afterwards, and in quenching boiler, cracking gas is cooled to 300-600 DEG C, with
Make cracking gas that cracking reaction not occur, reclaim heat simultaneously；Fuel system is for steam cracking reaction mistake
Journey puies forward heating load.Described segregation apparatus for being separated into the hydrocarbon of different carbon number by cracking gas.As a rule,
Described segregation apparatus specifically includes that oil scrubber, water scrubber, ice chest, compressor, domethanizing column, de-second
Alkane tower, ethylene rectifying column, depropanizing tower, propylene rectification tower, debutanizing tower, C2 and C3 hydrogenation plant,
C2 and C3 rectifying column, methanation device and BEU.The implementation of described segregation apparatus
The most known to those skilled in the art, do not repeat them here.
According to the present invention, in the case of described steam cracking reaction is carried out in pyrolysis furnace, in described steaming
During vapour cracking reaction, the coil outlet temperature of described pyrolysis furnace is preferably 760-839 DEG C, more preferably
For 780-839 DEG C；Water weight of oil than preferably 0.3-1, more preferably 0.35-0.65.Additionally, described
During steam cracking reaction, other Parameter Conditions of described pyrolysis furnace can be according to conventional process conditions
Implement, be not particularly limited in the present invention.
Hereinafter will be described the present invention by embodiment.
In the following Examples and Comparative Examples, the yield of propylene and butadiene calculates according to below equation:
The weight ÷ steam cracking reaction of propylene in propene yield (weight %)=steam cracking reaction product
Gross weight × 100% of product；
The weight ÷ steam cracking of butadiene in butadiene yield (weight %)=steam cracking reaction product
Gross weight × 100% of product；
Total recovery (the weight %)=propene yield+butadiene yield of propylene and butadiene.
In following example and comparative example, the composition of the liquefied petroleum gas LPG used is as shown in table 1:
Table 1
Embodiment 1
This embodiment is used for propylene and the preparation method of isobutene. that the present invention provides is described.
(1) separate:
By liquefied petroleum gas LPG-1 with the inlet amount of 100kg/h, the feeding temperature of 40 DEG C, 11atm
Feed pressure introduces in the middle part of C4 tower described C4 tower and carries out rectification.The parameter of C4 tower is arranged by table 2,
The separating resulting of gained is as shown in table 3.Wherein, the material obtained at the bottom of C4 tower tower is normal butane and 2-fourth
The mixture of alkene, the mass content of normal butane is 86.00%, and the mass content of 2-butylene is 13.96%.
By the material obtained at the bottom of C4 tower tower, by Germany Krupp-cooper, you separate by extraction fractional distillation, respectively
Obtain normal butane and 2-butylene.
Table 2
| Numbering | C4 tower |
| Number of theoretical plate | 99.0 |
| Tower top temperature, DEG C | 34.1 |
| Column bottom temperature, DEG C | 57.7 |
| Tower top pressure, atm | 4.5 |
| Tower bottom pressure, atm | 6.0 |
| Reflux ratio | 20.0 |
Table 3
(2) steam cracking reaction:
Normal butane step (1) obtained and 2-butylene introduce CBL-III type pyrolysis furnace respectively and (are purchased from
China PetroChemical Corporation, lower with) in carry out steam cracking reaction, obtain two kinds of steam crackings and produce
Thing.Then isolate propylene and butadiene after being mixed by two kinds of steam cracking products, and calculate
Propylene and the yield of butadiene, wherein, the condition of steam cracking reaction is as shown in table 6 below, result such as table
Shown in 7.
Embodiment 2
This embodiment is used for propylene and the preparation method of isobutene. that the present invention provides is described.
(1) separate:
The piece-rate system used includes C3 tower, C4 tower, C5 tower and butylene tower, by liquefied petroleum gas LPG-2
Draw from the middle part of C3 tower with the inlet amount of 100kg/h, the feeding temperature of 40 DEG C, the feed pressure of 11atm
Enter and C3 tower carries out rectification, and the product obtained at the bottom of C3 tower tower is introduced from the middle part of C4 tower C4 tower
In carry out rectification, then product C4 column overhead obtained introduces butylene tower from the middle part of butylene tower and carries out
Rectification, introduces the product obtained at the bottom of C4 tower tower C5 tower in the middle part of C5 tower simultaneously and carries out rectification, will
The material obtained at the bottom of butylene tower tower is as cracking stock 1.Wherein, each tower parameter is arranged by table 4, gained
Separating resulting as shown in table 5.The material of C5 column overhead and the material of butylene column overhead are passed through respectively
Germany Krupp-cooper that extraction fractional distillation separates, and obtains normal butane, 1-butylene and 2-butylene.
Table 4
| Numbering | C3 tower | C4 tower | C5 tower | Butylene tower |
| Number of theoretical plate | 35.0 | 99.0 | 30.0 | 150.0 |
| Tower top temperature, DEG C | 26.8 | 38.2 | 50.8 | 31.99 |
| Column bottom temperature, DEG C | 76.0 | 58.1 | 93.6 | 39.31 |
| Tower top pressure, atm | 10.0 | 4.5 | 5.0 | 4.0 |
| Tower bottom pressure, atm | 10.1 | 6.0 | 5.1 | 4.5 |
| Reflux ratio | 20.0 | 20.0 | 3.0 | 20.0 |
Table 5
(2) steam cracking reaction:
The normal butane, 2-butylene, 1-butylene and the cracking stock 1 that step (1) are obtained introduce respectively
CBL-III type pyrolysis furnace carries out steam cracking reaction, then several steam cracking products obtained is mixed
Isolate propylene and butadiene after being combined, and calculate the yield of propylene and butadiene.Wherein, steam
The condition of vapour cracking reaction is as shown in table 6 below, and result is as shown in table 7.
Embodiment 3
This embodiment is used for propylene and the preparation method of isobutene. that the present invention provides is described.
Propylene and isobutene. is prepared, except for the difference that, in steam cracking reaction mistake according to the method for embodiment 2
Cheng Zhong, introduces CBL-III type by the mixture of normal butane, 2-butylene, 1-butylene and cracking stock 1
Pyrolysis furnace carries out steam cracking reaction.Wherein, the condition of steam cracking reaction is as shown in table 6, result
As shown in table 7.
Comparative example 1
This comparative example is for illustrating the reference preparation method of propylene and butadiene.
Liquefied petroleum gas LPG-1 is sent directly in CBL-R type pyrolysis furnace and carries out steam cracking reaction,
Obtain steam cracking product, from steam cracking product, then isolate propylene and butadiene, and calculate
Propylene and the yield of butadiene.Wherein, the condition of steam cracking reaction is as shown in table 6 below, result such as table
Shown in 7.
Comparative example 2
This comparative example is for illustrating the reference preparation method of propylene and butadiene.
Liquefied petroleum gas LPG-2 is sent directly in CBL-R type pyrolysis furnace and carries out steam cracking reaction,
Obtain steam cracking product, from steam cracking product, then isolate propylene and butadiene, and calculate
Propylene and the yield of butadiene.Wherein, the condition of steam cracking reaction is as shown in table 6 below, result such as table
Shown in 7.
Table 6
Table 7
By the data of table 7 it can be seen that use the method for the present invention can significantly improve propylene and butadiene
Yield.Specifically, in embodiment 1-3 use the normal butane that steam crack material is isolated and
N-butene, and the steam crack material used in comparative example 1-2 is respectively LPG-1 and LPG-2, result
Embodiment 1-3 obtains significantly higher propylene and butadiene yield, thus solves existing liquefaction stone
Oil gas utilization rate and the low problem of Economic Value Added.
The preferred embodiment of the present invention described in detail above, but, the present invention is not limited to above-mentioned reality
Execute the detail in mode, in the technology concept of the present invention, can be to the technical side of the present invention
Case carries out multiple simple variant, and these simple variant belong to protection scope of the present invention.
It is further to note that each the concrete technology described in above-mentioned detailed description of the invention is special
Levy, in the case of reconcilable, can be combined by any suitable means.In order to avoid need not
The repetition wanted, various possible compound modes are illustrated by the present invention the most separately.
Additionally, combination in any can also be carried out between the various different embodiment of the present invention, as long as its
Without prejudice to the thought of the present invention, it should be considered as content disclosed in this invention equally.
Claims (5)
1. propylene and a preparation method for butadiene, the method comprises the following steps:
(1) from liquefied petroleum gas, normal butane and n-butene are isolated；
(2) mixture of step (1) isolated normal butane Yu n-butene is carried out steam cracking reaction；
Wherein, containing iso-butane, normal butane and n-butene in described liquefied petroleum gas；And with described liquefaction
On the basis of the total content of oil gas, the content of described iso-butane is 5-70mol%, containing of described normal butane
Amount is 5-70mol%, and the content of described n-butene is 10-70mol%；
Described steam cracking reaction is carried out in pyrolysis furnace, and during described steam cracking reaction, institute
The coil outlet temperature stating pyrolysis furnace is 760-839 DEG C, and water weight of oil is than for 0.3-1.
Method the most according to claim 1, wherein, with the total content of described liquefied petroleum gas be
Benchmark, the content of described iso-butane is 5-30mol%, and the content of described normal butane is 25-60mol%,
The content of described n-butene is 10-60mol%.
Method the most according to claim 1, wherein, during described steam cracking reaction,
The coil outlet temperature of described pyrolysis furnace is 780-839 DEG C, and water weight of oil is than for 0.35-0.65.
Method the most according to claim 1, wherein, described pyrolysis furnace is tube cracking furnace.
Method the most according to claim 1 and 2, wherein, the method also includes from steam cracking
Product is isolated propylene and butadiene.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1668556A (en) * | 2002-07-12 | 2005-09-14 | 巴斯福股份公司 | Method for the production of butadiene from n-butane |
| CN101734990A (en) * | 2008-11-25 | 2010-06-16 | 中国石油天然气股份有限公司 | Method for preparing ethylene by steam cracking in pipe type cracking furnace |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2873301A (en) * | 1956-04-09 | 1959-02-10 | Sinclair Refining Co | Thermal process for preparing butadiene from butene-2 |
| KR100440479B1 (en) * | 2002-04-23 | 2004-07-14 | 주식회사 엘지화학 | Hydrocarbon pyrolysis process |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1668556A (en) * | 2002-07-12 | 2005-09-14 | 巴斯福股份公司 | Method for the production of butadiene from n-butane |
| CN101734990A (en) * | 2008-11-25 | 2010-06-16 | 中国石油天然气股份有限公司 | Method for preparing ethylene by steam cracking in pipe type cracking furnace |
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