CN105367519B - The method for producing propylene oxide using carbon four is mixed - Google Patents
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Abstract
The present invention relates to a kind of method for producing propylene oxide using carbon four is mixed, mainly solve the problems, such as to mix that four utilization rate of carbon is not high and added value is low in the prior art.The present invention is by using following steps：(a) using selective hydrogenation technology, it is monoolefine to make the butadiene hydrogenation in mixing carbon four；(b) using reaction rectification technique, the butylene 1 in mixing carbon four is made to be isomerized to butylene 2；(b) using olefin(e) disproportionation technology, butylene 2 is made to generate propylene with ethylene reaction；(c) using iso-butane cooxidation technology, the iso-butane in mixing C_4 hydrocarbon is made to react generation tert-butyl hydroperoxide with oxygen, the technical solution of generation propylene oxide is reacted with propylene later, it preferably solves the problems, such as this, available for production propylene oxide, improves in the commercial Application for mixing four chemical comprehensive utilization rate of carbon.
Description
Technical field
The present invention relates to a kind of methods for producing propylene oxide using carbon four is mixed.
Background technology
Propylene oxide (PO) is a kind of important basic organic chemical industry raw material, is the third-largest in addition to polypropylene, acrylonitrile
Acryloyl derivative, mainly for the production of polyether polyol, propylene glycol and all kinds of nonionic surfactants.At present, propylene oxide
Production technology mainly have chlorohydrination, conjugated oxidation and hydrogen peroxide direct oxidation method.Chlorohydrination is due to seriously polluted, high energy consumption
The features such as, it will gradually be eliminated.Conjugated oxidation is called indirect oxidation method, and being divided into ethylbenzene conjugated oxidation, (coproduction styrene is total to
Oxidizing process, abbreviation PO/SM methods), iso-butane conjugated oxidation (conjugated oxidation of the coproduction tert-butyl alcohol, abbreviation PO/TBA methods) and isopropylbenzene
Conjugated oxidation (abbreviation CHP methods).Conjugated oxidation overcomes the shortcomings that chlorohydrination, but long flow path, investment are greatly.The direct oxygen of hydrogen peroxide
Change method (HPPO methods) is simple for process, product yield is high, but the cost of catalyst and hydrogen peroxide is higher.Production of propylene oxide skill at present
The developments of art exploitation are concentrated mainly on environmentally protective new process research and development and improvement of traditional production technique etc..
C_4 hydrocarbon is one of Main By product of steam cracking device and catalytic cracking unit, wherein containing in varying numbers
Iso-butane, isobutene, butadiene, butene-1, butene-2 etc., these components are widely used industrial chemicals.Mixing carbon at present
Four generally by Butadiene Extraction, isobutene etherificate after, remaining carbon four mostly as liquefied gas as fuel use, added value compared with
It is low.With the continuous growth of four yield of carbon, the comprehensive utilization of C_4 hydrocarbon has become the strong approach of enterprise's cost efficiency, especially
The separation utilization of C 4 olefin each component is the key point that C_4 hydrocarbon appreciation utilizes.
US6743958B2 describes a kind of method using C_4 hydrocarbon as raw material selectively production propylene, which first passes through choosing
The butadiene hydrogenation mixed in carbon four for monoolefine and is removed alkynes by selecting property hydrogenation reactor, and hydrogenation reaction product is passed into
Isomerization reactor makes butene-1 be isomerized to butene-2, and isomerization reaction product enters stabilizer, and tower top removes hydrogen and first
Alkane, four component of tower reactor carbon enter rectifying column, and tower bottom of rectifying tower enters disproportionation reactor, reaction generation third rich in butene-2 distillate
Alkene.CN101279879B describes a kind of method for comprehensively utilizing mixing carbon four and producing propylene, which first passes through olefin catalytic and split
Solution technology makes the olefins by catalytic cracking in mixing carbon four be propylene, ethylene, then will react remaining using isomerization of butene technology
Butene-1 in mixing carbon four is isomerized to butene-2, butene-2 is made to be given birth to ethylene disproportionated reaction finally by olefin(e) disproportionation technology
Into propylene.Above all methods are all to utilize the method for four resource of carbon production propylene, and the alkene being only utilized in four raw material of carbon.It is right
Have no that related patents are reported in the method for comprehensive utilization C_4 hydrocarbon production propylene oxide.
Invention content
The present invention relates to a kind of methods for producing propylene oxide using carbon four is mixed.The technical problems to be solved by the invention
It is the problem of C_4 hydrocarbon utilization rate is not high, added value is low in the prior art.It provides and a kind of new epoxy third is produced by C_4 hydrocarbon
The method of alkane.This method for mix carbon four produce propylene oxide when, have mixing four comprehensive utilization ratio of carbon it is high, it is environmentally protective,
The characteristics of propylene oxide high income.
In order to solve the above-mentioned technical problem, the technical solution adopted by the present invention is as follows：One kind prepares epoxy third from hydrocarbon mixture
The method of alkane, includes the following steps：(a) four raw material of carbon and hydrogen are mixed and enters selective hydrogenation reactor, the fourth two in raw material
Alkene is hydrogenated to monoolefine, and hydrogenation reaction product enters reactive distillation column；(b) butene-1 is isomerized to fourth in reactive distillation column
Alkene -2, for tower top light component after segregator, gas phase discharge hydrogen, liquid phase iso-butane part extraction partly returns to tower as reflux
Interior, tower reactor must be rich in the distillate of butene-2；(c) enter the progress of peroxidization device instead after the iso-butane of extraction and oxygen mix
Should, unreacting oxygen is discharged from reactor head, and peroxidation reaction product enters first rectifying column, and tower reactor obtains tert-butyl hydroperoxide
Hydrogen distillate, distillate of the tower top containing iso-butane are recycled back into peroxidization device；(d) reactive distillation tower reactor is rich in butene-2
Distillate enters disproportionation reactor with ethylene, and disproportionated reaction product enters Second distillation column, side take-off propylene；(e) it is above-mentioned to adopt
The propylene gone out enters epoxidation reactor, reaction generation epoxy after being mixed with first rectifying column kettle tert-butyl hydroperoxide distillate
Propane.
In the above-mentioned technical solutions, mixing four raw material of carbon mainly contains butadiene, iso-butane, butene-1, butene-2, positive fourth
The components such as alkane mix carbon four and hydrogen and enter selective hydrogenation reactor, wherein butadiene be selectively hydrogenated to butene-1 and/
Or butene-2, used catalyst are at least one of load including selected from nickel, zinc or palladium on the alumina support.Choosing
30~100 DEG C, 0.6~4.0MPaG of reaction pressure, 1~30hr of reaction velocity of selecting property hydrogenation reactor inlet temperature-1, hydrogen with
Butadiene molar ratio 1~1.2.
Selective hydrogenation product enters reactive distillation column, and reactive distillation column is followed successively by rectifying section, reaction from top to bottom
Section, stripping section, conversion zone are not limited to a catalyst bed, and conversion zone is located at the top of tower, to ensure that isomerization is in advantageous
In in the area of generation butene-2, catalyst be load on the alumina support comprising being selected from least one of nickel, zinc or palladium.
Rest part is common fractional distillation filling-material in addition to catalyst in tower.Butene-1 is isomerized to butene-2 in reactive distillation column, selection
The a small amount of butadiene that may contain in property hydrogenation reaction product is further hydrogenated to monoolefine.
Reactive distillation tower top light component is after segregator, and gas phase discharge hydrogen, liquid phase iso-butane part is returned as reflux
In tower, rest part extraction, and reacted with after oxygen mix into peroxidization device.110~150 DEG C of reaction temperature,
2.0~6.0MPaG of reaction pressure.Unreacting oxygen is discharged from reactor head.Peroxidation reaction product enters first rectifying column
It is detached, distillate of the tower top containing iso-butane and the tert-butyl alcohol is recycled back into peroxidization device, tower reactor extraction t-butyl peroxy
Change hydrogen.
Distillate of the reactive distillation tower reactor rich in butene-2 enters disproportionation reactor, reaction generation propylene with ethylene.Reaction
The total number of theoretical plate 40~100 of rectifying column, theoretical number of plates of rectifying section 3~10, conversion zone are highly equivalent to 5~15 pieces of theoretical plates, tower
Push up operating pressure 0.3MPaG~1.0MPaG, preferably 0.4MPaG~0.8MPaG, reflux ratio 5~50.
Disproportionated reaction product enters Second distillation column and is detached, and the unreacted ethylene of tower top and tower reactor part are unreacted
Mixing carbon four is recycled back into disproportionation reactor, side take-off propylene product.Catalyst employed in disproportionation reactor is load
Including selected from least one of tungsten oxide, molybdenum oxide or rheium oxide on silica support.250~500 DEG C of reaction temperature,
0~5.0MPaG of reaction pressure.
Second distillation column side line propylene enters epoxidation reactor after being mixed with first rectifying column kettle tert-butyl hydroperoxide,
Reaction generation propylene oxide, the catalyst used is catalyst with base of molybdenum.80~150 DEG C of reaction temperature, reaction pressure 2.0~
7.0MPaG, epoxidation reaction product obtain propylene oxide after separation.
In above-mentioned technical proposal, by weight percentage, mix in four raw material of carbon and contain 2~40% butadiene；It is preferred that
To contain 5~35% butadiene；More preferably containing 5~20% butadiene；
In above-mentioned technical proposal, by weight percentage, mix in four raw material of carbon and contain 10~90% iso-butane；It is preferred that
To contain 15~80% iso-butane；More preferably containing 30~80% iso-butane；
In above-mentioned technical proposal, by weight percentage, mix and contain 2~20% butene-1s in four raw material of carbon；Preferably
Contain 5~20% butene-1s；More preferably contain 5~15% butene-1s；
In above-mentioned technical proposal, by weight percentage, mix and contain 2~35% butene-2s in four raw material of carbon；Preferably
Contain 5~30% butene-2s；More preferably contain 5~20% butene-2s；
In above-mentioned technical proposal, by weight percentage, mix and contain 0.5~20% normal butane in four raw material of carbon；It is preferred that
To contain 1~15% normal butane；More preferably contain 2~8% normal butanes.
It, can containing according to iso-butane in four raw material of carbon and alkene using mixing during carbon four produces propylene oxide
Amount, flexibly supplements fresh iso-butane, butadiene and n-butene.On the one hand, it when the iso-butane content height in four raw material of carbon, utilizes
It, can be by supplementing fresh fourth two when the propylene obtained by olefin(e) disproportionation in raw material cannot meet iso-butane to the needs of propylene
Alkene or n-butene or propylene make iso-butane fully react.On the other hand, when the iso-butane content in four raw material of carbon is low, in raw material
Propylene obtained by olefin(e) disproportionation still has residue after meeting iso-butane to the needs of propylene, then can be by supplementing fresh isobutyl
Alkane makes propylene fully react or directly produce remaining propylene.
The present invention by using selective hydrogenation technology, reaction rectification technique, disproportionation technology and iso-butane cooxidation technology,
C_4 hydrocarbon is made full use of to produce propylene oxide, improves the comprehensive utilization ratio and added value of mixing carbon four, environmentally protective, epoxy third
Alkane high income achieves preferable technique effect.
Description of the drawings
Fig. 1, which is that the present invention is a kind of, utilizes the method process flow diagram for mixing the production propylene oxide of carbon four.
1 is raw material mixing carbon four in Fig. 1, and 2 be hydrogen, and 3 be selective hydrogenation reactor, and 4 produce for selective hydrogenation
Object, 5 be reactive distillation column, and 6 be segregator, and 7 be reactive distillation tower top fixed gas, and 8 evaporate for reactive distillation tower top liquid phase iso-butane
Go out object, 9 be oxygen, and 10 be peroxidization device, and 11 be unreacting oxygen, and 12 be first rectifying column, 13 for recycle isobutane with
Tert-butyl alcohol distillate, 14 be tert-butyl hydroperoxide distillate, and 15 be ethylene, and 16 be disproportionation reactor, and 17 be Second distillation column,
18 be cyclic ethylene, and 19 be cyclic carbon four, and 20 be unreacted carbon four, and 21 be side line propylene, and 22 be epoxidation reactor, and 23 be ring
Oxidation reaction product separative element, 24 be propylene, and 25 be propylene oxide, and 26 be heavy constituent.
Flow as shown in Figure 1 mixes carbon 41 and hydrogen 2 and enters selective hydrogenation reactor 3, by selective hydrogenation,
Butadiene is hydrogenated to monoolefine.Selective hydrogenation product 4 enters reactive distillation column 5, the butadiene in reactive distillation column 5
Monoolefine is further hydrogenated to, butene-1 is isomerized to butene-2, and tower top light component passes through 6 partial condensation of segregator, fixed gas 7
It is discharged from top, Partial Liquid Phase iso-butane is returned as reflux in tower, after remaining fluid phase iso-butane distillate 8 and the mixing of oxygen 9
It is reacted into peroxidization device 10, unreacting oxygen 11 is discharged from reactor head.Peroxidation reaction product enters the
One rectifying column 12 is detached, and tower top iso-butane is recycled back into peroxidization device with tert-butyl alcohol distillate 13.Reactive distillation column
Mixture and ethylene 15 of the kettle rich in butene-2 are reacted after mixing into disproportionation reactor 16.Disproportionated reaction product passes through
Two rectifying columns 17 are detached, and tower top unreacting ethylene 18 is recycled back into disproportionation reactor, and tower reactor is unreacted mixing carbon four, portion
Divide 19 as disproportionation reactor is recycled back into, part 20 is discharged.The propylene 21 of side take-off and first rectifying column kettle tertiary butyl mistake
Hydrogen oxide distillate 14 is reacted jointly into epoxidation reactor 22, and reaction product obtains propylene after separative element 23
24th, propylene oxide 25 and heavy constituent 26.
Below by specific embodiment, the present invention is further illustrated, and still, the scope of the present invention is not only limited in
The range that embodiment is covered.
Specific embodiment
【Embodiment 1】
As shown in Figure 1, four feed composition (weight %) of carbon is：Butadiene 5.0%, iso-butane：80.0%, butene-1：
5.2%, butene-2：8.0%, normal butane：1.8%.Selective hydrogenation catalyst is Ni/Al2O3, reactor inlet temperature
30 DEG C, reaction pressure 1.5MPaG, reaction velocity 4hr-1, hydrogen and butadiene molar ratio 1.1；The total number of theoretical plate of reactive distillation column
55 (counting from top to bottom, the same below), theoretical number of plates of rectifying section 5, conversion zone are equivalent to 8 pieces of height equivalent to a theoretical plate, and conversion zone filling is urged
Agent is Ni/Al2O3, rest part filling stainless steel triangle helical packing, tower top operating pressure 0.6MPaG；Disproportionated reaction is catalyzed
Agent is WO3/SiO2, 280 DEG C, reaction pressure 2.5MPaG of reaction temperature, unreacted carbon 4 90% (weight) is recycled back to disproportionated reaction
Device；138 DEG C of peroxidization device reaction temperature, reaction pressure 3.2MPaG；Epoxidation catalysts are ammonium heptamolybdate, reaction
110 DEG C, reaction pressure 3.5MPaG of temperature, can obtain propylene oxide 35.6% (weight, for iso-butane content in material carbon 41,
The propylene oxide of 35.6kg can be obtained by the reaction in iso-butane i.e. per 100kg).【Embodiment 2】
As shown in Figure 1, four feed composition (weight %) of carbon is：Butadiene 10.0%, iso-butane：65.0%, butene-1：
7.2%, butene-2：12.0%, normal butane：5.8%.Selective hydrogenation catalyst is Ni/Al2O3, reactor inlet temperature
40 DEG C, reaction pressure 2.0MPaG, reaction velocity 5hr-1, hydrogen and butadiene molar ratio 1.1；The total number of theoretical plate of reactive distillation column
60 (counting from top to bottom, the same below), theoretical number of plates of rectifying section 5, conversion zone are equivalent to 8 pieces of height equivalent to a theoretical plate, and conversion zone filling is urged
Agent is Ni/Al2O3, rest part filling stainless steel triangle helical packing, tower top operating pressure 0.6MPaG；Disproportionated reaction is catalyzed
Agent is WO3/SiO2, 280 DEG C, reaction pressure 2.5MPaG of reaction temperature, unreacted carbon 4 90% (weight) is recycled back to disproportionated reaction
Device；138 DEG C of peroxidization device reaction temperature, reaction pressure 3.2MPaG；Epoxidation catalysts are ammonium heptamolybdate, reaction
110 DEG C, reaction pressure 3.5MPaG of temperature can obtain propylene oxide 36.2% (weight, for iso-butane content in material carbon 4 1).
【Embodiment 3】
As shown in Figure 1, mixing carbon four forms (weight %) and is：Butadiene 15.0%, iso-butane：50.0%, butene-1：
10.2%, butene-2：17.0%, normal butane：7.8%.Selective hydrogenation catalyst is Pd/Al2O3, reactor inlet temperature
40 DEG C, reaction pressure 2.0MPaG, reaction velocity 8hr of degree-1, hydrogen and butadiene molar ratio 1.05；The total theoretical plate of reactive distillation column
Number 65 (counts, the same below) from top to bottom, theoretical number of plates of rectifying section 5, and conversion zone is equivalent to 12 pieces of height equivalent to a theoretical plate, conversion zone filling
Catalyst is Pd/Al2O3, rest part filling stainless steel triangle helical packing, tower top operating pressure 0.5MPaG；Disproportionated reaction is urged
Agent is WO3/SiO2, 300 DEG C, reaction pressure 2.8MPaG of reaction temperature, it is anti-that unreacted carbon 4 85% (weight) is recycled back to disproportionation
Answer device；135 DEG C of peroxidization device reaction temperature, reaction pressure 3.0MPaG；Epoxidation catalysts are ammonium heptamolybdate, instead
120 DEG C, reaction pressure 3.6MPaG of temperature is answered, can obtaining propylene oxide 36.6%, (weight contains for iso-butane in material carbon 41
Amount).
【Embodiment 4】
As shown in Figure 1, mixing carbon four forms (weight %) and is：Butadiene 20.0%, iso-butane：35.0%, butene-1：
12.2%, butene-2：20.0%, normal butane：12.8%.Selective hydrogenation catalyst is Pd/Al2O3, reactor inlet temperature
50 DEG C, reaction pressure 2.5MPaG, reaction velocity 9hr of degree-1, hydrogen and butadiene molar ratio 1.05；The total theoretical plate of reactive distillation column
Number 75 (counts, the same below) from top to bottom, theoretical number of plates of rectifying section 7, and conversion zone is equivalent to 15 pieces of height equivalent to a theoretical plate, conversion zone filling
Catalyst is Pd/Al2O3, rest part filling stainless steel triangle helical packing, tower top operating pressure 0.5MPaG；Disproportionated reaction is urged
Agent is MoO3/SiO2, 350 DEG C, reaction pressure 3.0MPaG of reaction temperature, it is anti-that unreacted carbon 4 85% (weight) is recycled back to disproportionation
Answer device；130 DEG C of peroxidization device reaction temperature, reaction pressure 2.2MPaG；Epoxidation catalysts are hexacarbonylmolybdenum, instead
130 DEG C, reaction pressure 4.0MPaG of temperature is answered, can obtaining propylene oxide 36.9%, (weight contains for iso-butane in material carbon 41
Amount).
【Embodiment 5】
As shown in Figure 1, mixing carbon four forms (weight %) and is：Butadiene 35.0%, iso-butane：15.0%, butene-1：
18.2%, butene-2：29.0%, normal butane：12.8%.Selective hydrogenation catalyst be Pd/Al2O3, reactor inlet
Temperature 60 C, reaction pressure 3.0MPaG, reaction velocity 9hr-1, hydrogen and butadiene molar ratio 1.05；Reactive distillation column premier
It (is counted from top to bottom, the same below) by plate number 80, theoretical number of plates of rectifying section 10, conversion zone is equivalent to 15 pieces of height equivalent to a theoretical plate, reaction
Section loading catalyst is Pd/Al2O3, rest part filling stainless steel triangle helical packing, tower top operating pressure 0.5MPaG；Disproportionation
Catalysts are MoO3/SiO2, 350 DEG C, reaction pressure 3.0MPaG of reaction temperature, unreacted carbon 4 85% (weight) is recycled back to
Disproportionation reactor；130 DEG C of peroxidization device reaction temperature, reaction pressure 2.2MPaG；Epoxidation catalysts are six carbonyls
Molybdenum, 130 DEG C, reaction pressure 4.0MPaG of reaction temperature can obtain (the weight, for isobutyl in material carbon 41 of propylene oxide 37.2%
Alkane content).
Claims (9)
1. a kind of method for producing propylene oxide using carbon four is mixed, includes the following steps successively：
(a) four raw material of carbon and hydrogen are mixed and enters selective hydrogenation reactor, the butadiene in raw material is hydrogenated to monoolefine, adds
Hydroformylation reaction product enters reactive distillation column；
(b) butene-1 is isomerized to butene-2 in reactive distillation column, and tower top light component is after segregator, gas phase discharge hydrogen, liquid
Phase iso-butane part produces, and is partly returned in tower as reflux, and tower reactor must be rich in the distillate of butene-2；
(c) it is reacted after the iso-butane of extraction and oxygen mix into peroxidization device, unreacting oxygen is from reactor top
Portion discharges, and peroxidation reaction product enters first rectifying column, and tower reactor obtains tert-butyl hydroperoxide distillate, and tower top is containing iso-butane
Distillate is recycled back into peroxidization device；
(d) distillate and ethylene of the reactive distillation tower reactor rich in butene-2 enter disproportionation reactor, and disproportionated reaction product enters the
Two rectifying columns, side take-off propylene；
(e) enter epoxidation reaction after the propylene of above-mentioned extraction is mixed with first rectifying column kettle tert-butyl hydroperoxide distillate
Device, reaction generation propylene oxide；
Wherein, step (b) reactive distillation column conversion zone load catalyst be load on the alumina support comprising be selected from nickel, zinc
Or at least one of palladium；The total number of theoretical plate 40~100 of reactive distillation column, theoretical number of plates of rectifying section 3~10, conversion zone height phase
When in 5~15 pieces of theoretical plates, tower top operating pressure 0.3MPaG~1.0MPaG, reflux ratio 5~50.
2. the method for producing propylene oxide using carbon four is mixed according to claim 1, it is characterised in that C_4 hydrocarbon contains fourth two
Alkene, iso-butane, butene-1, butene-2 and normal butane.
3. the method for producing propylene oxide using carbon four is mixed according to claim 1, it is characterised in that can be according to C_4 hydrocarbon
The content of iso-butane and alkene in raw material, flexibly supplements fresh iso-butane, butadiene and n-butene.
4. the method for producing propylene oxide using carbon four is mixed according to claim 1, it is characterised in that selective hydrogenation is anti-
Answer 30~100 DEG C, 0.6~4.0MPaG of reaction pressure, 1~30hr of reaction velocity of device inlet temperature-1, hydrogen and butadiene mole
Than 1~1.2.
5. the method for producing propylene oxide using carbon four is mixed according to claim 1, it is characterised in that disproportionated reaction generates
Propylene, the catalyst used is is supported on including in tungsten oxide, molybdenum oxide or rheium oxide at least on silica support
It is a kind of.
6. the method for producing propylene oxide using carbon four is mixed according to claim 1, it is characterised in that disproportionation reactor is anti-
250~500 DEG C, 0~5.0MPaG of reaction pressure of temperature is answered, disproportionated reaction product is after separation, and side take-off propylene, tower top is not
The unreacted mixing carbon four of the ethylene of reaction and tower reactor part is recycled back into disproportionation reactor.
7. the method for producing propylene oxide using carbon four is mixed according to claim 1, it is characterised in that peroxidization device
110~150 DEG C, 2.0~6.0MPaG of reaction pressure of reaction temperature, for peroxidation reaction product after separation, tower top is unreacted different
Butane is recycled back into peroxidization device.
8. the method for producing propylene oxide using carbon four is mixed according to claim 1, it is characterised in that epoxidation reaction is given birth to
Into propylene oxide, the catalyst used is catalyst with base of molybdenum.
9. the method for producing propylene oxide using carbon four is mixed according to claim 1, it is characterised in that epoxidation reactor
80~150 DEG C of reaction temperature, 2.0~7.0MPaG of reaction pressure.
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