CN101289368A - Technological process for continuously producing sec-butyl alcohol by direct hydration of n-butene - Google Patents
Technological process for continuously producing sec-butyl alcohol by direct hydration of n-butene Download PDFInfo
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- CN101289368A CN101289368A CNA2008100164951A CN200810016495A CN101289368A CN 101289368 A CN101289368 A CN 101289368A CN A2008100164951 A CNA2008100164951 A CN A2008100164951A CN 200810016495 A CN200810016495 A CN 200810016495A CN 101289368 A CN101289368 A CN 101289368A
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Abstract
The invention relates to a technique method of the continuous production of 2-butanol by the direct hydration of n-butene, belonging to the technical field of petrochemical industry. The invention comprises the steps that under the existence of the catalyst of strong acid ion exchange resin, fresh raw material of the n-butene and a cycling n-butene are mixed up and enter a hydration reactor for a hydration reaction, and then enter a separation unit of crude products for separation; a refining unit of the n-butene is additionally arranged; one part of the unreacted n-butene which is separated from the separation unit of crude products is used as the cycling n-butene and is returned to the hydration reactor for further hydration reaction and the other part is sent to the refining unit of the n-butene for the rectification and n-butene is recycled after the removal of butane to be used as the fresh raw material of the n-butene continually. The method has the advantages of improving recycling, improving the volumetric efficiency of the hydration reactor, improving the yield of 2-butanol greatly, reducing ineffective circulation and reducing the consumption of energy, thus realizing the zero discharge of the n-butene with high yield and low energy consumption.
Description
Technical field
The present invention relates to a kind of processing method of continuously producing sec-butyl alcohol by direct hydration of n-butene, belong to the petrochemical technology field.
Background technology
The novel process of the n-butene direct hydration system sec-butyl alcohol that is catalyzer was succeeded in developing with the strong-acid ion exchange resin in preceding Germany in 1984, and build up 60kt/a direct hydration method full scale plant, its temperature of reaction is 150-170 ℃, reaction pressure is 5-7MPa, the mol ratio of water/n-butene is 15: 1～20: 1, and the sec-butyl alcohol overwhelming majority that reaction is generated is dissolved in C
4In the hydrocarbon.Resultant of reaction divides at the liquid-liquid separator that water-yielding stratum is laggard goes into to take off C
4Tower, the tower still is water-free crude secbutyl alcohol, goes the back operation refining.A cat head distilled unreacted n-butene part loops back the hydration reactor, and small portion gives off the battery limit (BL), so as not to the normal butane accumulation, per pass conversion 4-6%.
Produce in the process of industrialization of sec-butyl alcohol at the n-butene direct hydration, many patents occurred.English Patent 1,374,368,1,386,195, in this technology, the mol ratio of water/n-butene is up to 100-173: 1, and the raw material n-butene once passes through, though per pass conversion, produces a large amount of enol water up to 70%, sec-butyl alcohol can't reclaim, and raw material also is not fully utilized.United States Patent (USP) 4,476,333,4,831,197 adopts little water/n-butene mol ratio hydrocarbon circulation technology, and unreacted n-butene major part is looped back the hydration reactor with the hydration of fresh n-butene raw material, and small portion is discharged the battery limit (BL).This technology has been compared obvious superiority with the technology of big flood/n-butene mol ratio, is adopted by industrial production.But owing to discharged part unreacted n-butene, significant loss is bigger, and the total transformation efficiency of n-butene is not high.Japan bright dipping emerging product company is that the n-butene direct hydration of catalyzer is produced in the technological process of sec-butyl alcohol with the heteropolyacid in exploitation, and the researchist finds n-butene (n-butene critical temperature T under super critical condition
C145 ℃, emergent pressure P
CBe 3951.87KP
a), the weight concentration of sec-butyl alcohol in the n-butene gas phase is up to 50%, in technological process, n-butene is a reactant, simultaneously the reaction product sec-butyl alcohol is played a part supercritical extraction again, the sec-butyl alcohol that reaction is produced almost all is dissolved in the organic phase of n-butene formation, and aqueous phase contains sec-butyl alcohol seldom, need not reclaim directly recycle.In this technology, unreacted n-butene also is most of circulation, and small portion row battery limit (BL) prevents the accumulation of butane.
In Chinese application number is 971164061 patent, for solution causes significant loss and the low problem of total conversion rate because of discharge unit unreacted n-butene, increased an auxiliary reactor, under reaction conditions than big flood/n-butene mol ratio, the n-butene of discharge unit is further reacted by auxiliary reactor, give off the battery limit (BL) then.The sec-butyl alcohol that generates is dissolved in aqueous phase, and this water loops back main reactor as the process water of main reactor, wishes to increase the output of sec-butyl alcohol.But the sec-butyl alcohol that loops back main reactor can influence the chemical equilibrium of hydration reaction, reduces the per pass conversion of main reactor n-butene, and effect is unsatisfactory.
Above technology has advantage separately, all there is the low and big shortcoming of significant loss of total conversion rate, this part raw material that is discharged, detrimental impurity such as the iso-butylene of the inside and diolefine all are eliminated in the hydration reaction process totally, belong to the high quality raw material that only contain butane and n-butene, it is very unfortunate having lost.Loss for fear of raw material is excessive, and it is generally all on the low side that the n-butene material content of reactor is closed in water inlet in the above-mentioned technology.Approximately be controlled at weight concentration about 80%, the volumetric efficiency of hydration reactor is low, has influenced the output of sec-butyl alcohol.A large amount of butane by repeatedly intensification, cooling, evaporation, condensation, has therefore caused product energy consumption higher in working cycle in the reaction mass.
Summary of the invention
The object of the present invention is to provide a kind of processing method of improved continuously producing sec-butyl alcohol by direct hydration of n-butene, increase yield, improved the volumetric efficiency of hydration reactor, significantly improved the output of sec-butyl alcohol, reduced invalid circulation, reduce energy consumption, accomplished the zero release of high yield and low cost n-butene.
The processing method of continuously producing sec-butyl alcohol by direct hydration of n-butene of the present invention, in the presence of the strong acid ion exchange resin catalyzer, fresh n-butene raw material and circulation n-butene are mixed into hydration reactor and carry out hydration reaction, entering the crude product separating unit then separates, set up the n-butene refined unit, by the isolated unreacted n-butene of crude product separating unit, a part is back to hydration reactor as the circulation n-butene and continues to participate in hydration reaction, another part is sent to the n-butene refined unit and is made with extra care, remove butane, reclaim n-butene, continue to use as fresh n-butene raw material.
By in former flow process, increasing n-butene feed purification unit,, hydration reactor, liquid-liquid separator refining and take off C by n-butene
4Tower is formed a whole set of machinery, forms two circulation routes in the flow process.One is from taking off C
4The unreacted n-butene part that tower comes out loops back the hydration reactor, is mixed into hydration reactor with fresh n-butene raw material and produces sec-butyl alcohol; Another is from taking off C
4Unreacted n-butene another part that tower comes out goes the n-butene refined unit to remove the butane component, prevents that butane from accumulating in system.Improve the flow that removes the n-butene refined unit, the amount that increase enters the fresh n-butene raw material of hydration reactor is guaranteeing under the constant prerequisite of total feed, has improved to enter hydration reactor n-butene concentration, has improved the volumetric efficiency of hydration reactor.Increase the output of sec-butyl alcohol, reduced invalid circulation, saved energy.Compare with technology in the past, the present invention has increased the n-butene refined unit, makes the unreacted n-butene that discharges in technology in the past, can return the n-butene refined unit, deviates from the butane component, reclaims n-butene.And can improve the amount of returning, the n-butene concentration that enters hydration reactor is brought up to a reasonable levels.
The flow of n-butene refined unit is sent in adjusting, and it is 90～98% suitable making the weight concentration that enters hydration reactor mixing n-butene, and numerical value can be adjusted with the height of fresh n-butene concentration.
Fresh n-butene raw material with take off C
4After the circulation n-butene that cat head is separated mixes, be preheated to 140-180 ℃ and enter hydration reactor, the mol ratio 1-10 of water and n-butene: 1, pressure 4.0-8.0MPa, reaction mass passes through beds from bottom to top, divide water-yielding stratum in the liquid-liquid separator after, the organic phase that contains sec-butyl alcohol enters takes off C
4Tower, the unreacted n-butene steams from cat head, and a part loops back the hydration reactor, and another part returns the n-butene refined unit.N-butene in hydration reactor and liquid-liquid separator is a supercritical state.
The temperature of reaction of hydration reaction is preferably in 150-170 ℃, and reaction pressure is preferably in 6.0-8.0MPa, and the mol ratio of water and n-butene is preferably in 1-5: 1.Enter preferably (gas-liquid criticality) reaction under supercritical state of reaction mass of hydration reactor, reacted material is preferably in and carries out the liquid-liquid separation under the supercritical state.
Fresh n-butene weight concentration is preferably 95-99.8%.
The key difference of the present invention and prior art is: the present invention has increased n-butene feed purification unit in former flow process,, hydration reactor, liquid-liquid separator refining by n-butene, takes off C
4Tower is formed a whole set of machinery, form two circulation routes in the flow process, the unreacted n-butene that discharges in the prior art is all returned the n-butene refined unit, increase yield, total conversion rate 100%, realized the zero release of n-butene, and return the flow of n-butene refined unit by raising, improve the n-butene concentration that enters hydration reactor, improved the volumetric efficiency of hydration reactor, improved the output of sec-butyl alcohol, production capacity improves more than 15%, owing to improved the concentration of reaction mass, reduced invalid circulation, reduced energy consumption.
Description of drawings
Fig. 1, process flow diagram of the present invention.
Fig. 2, prior art processes schematic flow sheet.
1,2,3,4, line of pipes among the figure:.
Embodiment
The invention will be further described below in conjunction with embodiment.
As shown in Figure 1, fresh n-butene raw material mixes the laggard hydration reactor of going into by pipeline 1 with the circulation n-butene of pipeline 3, from bottom to top by the resin catalyst bed, carry out hydration reaction, reaction mass enters the liquid-liquid separator by the top discharge and isolates water, and water-free organic phase enters takes off C
4Tower is isolated product sec-butyl alcohol and the by product trimethyl carbinol, secondary butyl ether etc., and unreacted n-butene is sent by overhead line 2, major part is returned hydration reactor by circulation line 3, small portion returns the n-butene refined unit by recovery line 4, removes butane, reclaims n-butene.
Enter the mixing n-butene 50t/h (ton/hour) of hydration reactor, weight concentration is 80%, and fresh n-butene weight concentration is 98%, 150 ℃ of temperature, and pressure 8.0MPa, the mol ratio of water and n-butene is 3: 1, one way turnover ratio 6%.Sec-butyl alcohol output 3.17t/h, circulation n-butene 47.34t/h, weight concentration 78.99% is returned the exquisite unit n-butene 0.26t/h of n-butene, and weight concentration 78.99% is replenished fresh n-butene 2.66t/h.N-butene total conversion rate 100%.
Identical with embodiment 1 technical process, temperature, pressure, water are identical with the mol ratio of n-butene, and per pass conversion is identical.Enter the mixing n-butene 50t/h of hydration reactor, weight concentration 85%, fresh n-butene weight concentration 98%.The output 3.37t/h of sec-butyl alcohol, circulation n-butene 47.05t/h, weight concentration 84.19% is returned the n-butene 0.40t/h of n-butene refined unit, and weight concentration 84.19% is replenished fresh divinyl 2.95t/h.N-butene total conversion rate 100%.
Identical with embodiment 1 technical process, temperature, pressure, water are identical with the mol ratio of n-butene, and per pass conversion is identical.Enter the mixing n-butene 50t/h of hydration reactor, weight concentration 90%, the weight concentration 98% of fresh n-butene.The output 3.57t/h of sec-butyl alcohol, circulation n-butene 46.68t/h, weight concentration is returned the n-butene 0.62t/h of n-butene refined unit 89.43%, and weight concentration 89.43% is replenished fresh divinyl 3.32t/h.N-butene total conversion rate 100%.
Identical with embodiment 1 technical process, temperature, pressure, water are identical with the mol ratio of n-butene, and per pass conversion is identical.Enter the mixing n-butene 50t/h of hydration reactor, weight concentration 95%, fresh n-butene weight concentration 98%.The output 3.77t/h of sec-butyl alcohol, circulation n-butene 45.4t/h, weight concentration is returned the n-butene 1.75t/h of n-butene refined unit 94.7%, and weight concentration 94.7% is replenished fresh divinyl 4.6t/h.N-butene total conversion rate 100%.
Embodiment 5
Identical with embodiment 1 technical process, temperature, pressure, water and n-butene are than identical, and per pass conversion is identical.Enter the mixing n-butene 50t/h of hydration reactor, weight concentration 97%, fresh n-butene weight concentration 98%.The output 3.85t/h of sec-butyl alcohol, circulation n-butene 41.8t/h, weight concentration is returned the n-butene 5.29t/h of n-butene refined unit 96.81%, and weight concentration 96.81% is replenished fresh divinyl 8.20t/h.N-butene total conversion rate 100%.
Comparative example:
As shown in Figure 2, fresh n-butene raw material mixes the laggard hydration reactor of going into by pipeline 1 with the circulation n-butene of pipeline 3, from bottom to top by the resin catalyst bed, carry out hydration reaction, reaction mass enters the liquid-liquid separator by the top discharge and isolates water, and water-free organic phase enters takes off C
4Tower is isolated product sec-butyl alcohol and the by product trimethyl carbinol, secondary butyl ether etc., and unreacted n-butene is sent by overhead line 2, and major part loops back the hydration reactor by circulation line 3, and small portion is discharged battery limit (BL)s by pipeline 4, avoids butane to accumulate in system.
Comparative example 1
Enter the mixing n-butene 50t/h of hydration reactor, weight concentration 80%, the weight concentration 98% of fresh n-butene, 150 ℃ of temperature, pressure 8.0MPa, the mol ratio of water and n-butene 3: 1, per pass conversion 6%.Sec-butyl alcohol output 3.17t/h, circulation n-butene 47.34t/h, weight concentration 78.99% is replenished fresh n-butene 2.66t/h, discharges n-butene 0.26t/h, weight concentration 78.99%.Loss n-butene 0.21t/h, total conversion rate 91.15%.
Comparative example 2
Identical with comparative example 1 technical process, temperature, pressure, water and n-butene are than identical, and per pass conversion is identical.Enter the mixing n-butene 50t/h of hydration reactor, weight concentration 90%, fresh n-butene weight concentration 98%.The output 3.57t/h of sec-butyl alcohol, circulation n-butene 46.68t/h, weight concentration is replenished fresh divinyl 3.32t/h 89.43%, discharges n-butene 0.62t/h, weight concentration 89.43%, loss n-butene 0.55t/h, total conversion rate 83.08%.
Comparative example 3
Identical with comparative example 1 technical process, temperature, pressure, water and n-butene are than identical, and per pass conversion is identical.Enter the mixing n-butene 50t/h of hydration reactor, weight concentration 95%, fresh n-butene weight concentration 98%.The output 3.77t/h of sec-butyl alcohol, circulation n-butene 45.4t/h, weight concentration is replenished fresh divinyl 4.6t/h 94.7%, discharges n-butene 1.75t/h, weight concentration 94.7%, loss n-butene 1.66t/h, total conversion rate 63.19%.
The present invention selects for use following parameters to experimentize respectively with embodiment 1 basis, all obtains good result.
The mol ratio of water and n-butene is 2: 1 in the hydration reaction, and 160 ℃ of temperature of reaction, reaction pressure are 7.0MPa.
The mol ratio of water and n-butene is 5: 1 in the hydration reaction, and 150 ℃ of temperature of reaction, reaction pressure are 6.0MPa.
The mol ratio of water and n-butene is 4: 1 in the hydration reaction, and 165 ℃ of temperature of reaction, reaction pressure are 6.5MPa.
The mol ratio of water and n-butene is 3: 1 in the hydration reaction, and 155 ℃ of temperature of reaction, reaction pressure are 7.5MPa.
The mol ratio of water and n-butene is 3.5: 1 in the hydration reaction, and 160 ℃ of temperature of reaction, reaction pressure are 8.0MPa.
The mol ratio of water and n-butene is 2.5: 1 in the hydration reaction, and 170 ℃ of temperature of reaction, reaction pressure are 7.0MPa.
The mol ratio of water and n-butene is 4: 1 in the hydration reaction, and 155 ℃ of temperature of reaction, reaction pressure are 6.5MPa.
Claims (6)
1, a kind of processing method of continuously producing sec-butyl alcohol by direct hydration of n-butene, in the presence of the strong acid ion exchange resin catalyzer, fresh n-butene raw material and circulation n-butene are mixed into hydration reactor and carry out hydration reaction, entering the crude product separating unit then separates, it is characterized in that setting up the n-butene refined unit, by the isolated unreacted n-butene of crude product separating unit, a part is back to hydration reactor as the circulation n-butene and continues to participate in hydration reaction, another part is sent to the n-butene refined unit and is made with extra care, remove butane, reclaim n-butene, continue to use as fresh n-butene raw material.
2, the processing method of continuously producing sec-butyl alcohol by direct hydration of n-butene according to claim 1 is characterized in that regulating the flow of sending to the n-butene refined unit, and making the weight concentration that enters hydration reactor mixing n-butene is 90～98%.
3, the processing method of continuously producing sec-butyl alcohol by direct hydration of n-butene according to claim 1 and 2, the weight concentration that it is characterized in that fresh n-butene raw material is 95～99.8%.
4, the processing method of continuously producing sec-butyl alcohol by direct hydration of n-butene according to claim 3 is characterized in that the mol ratio of water and n-butene is controlled to be 1-5 in the hydration reaction: 1.
5, the processing method of continuously producing sec-butyl alcohol by direct hydration of n-butene according to claim 4, the temperature of reaction that it is characterized in that hydration reaction is 150-170 ℃, reaction pressure is 6.0～8.0MPa.
6, the processing method of continuously producing sec-butyl alcohol by direct hydration of n-butene according to claim 5 is characterized in that hydration reactor moves under supercritical state.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102659514A (en) * | 2012-04-26 | 2012-09-12 | 凯瑞化工股份有限公司 | Method for producing sec-butyl alcohol |
| US8558036B2 (en) | 2010-11-15 | 2013-10-15 | Saudi Arabian Oil Company | Dual phase catalysts system for mixed olefin hydrations |
| CN106669375A (en) * | 2015-11-09 | 2017-05-17 | 中国石油化工股份有限公司 | Process for treating tail gases of methyl ethyl ketone unit |
| CN107459442A (en) * | 2016-06-03 | 2017-12-12 | 中国石油化工股份有限公司 | A kind of sec-butyl alcohol process units and technique |
| CN108003018A (en) * | 2017-12-26 | 2018-05-08 | 浙江新和成股份有限公司 | A kind of method and its equipment for preparing cyclopentanol at supercritical conditions |
| CN113165996A (en) * | 2018-11-20 | 2021-07-23 | 沙特基础工业全球技术有限公司 | Method and system for producing ethylene and at least one of butanol and alkyl tertiary butyl ether |
-
2008
- 2008-06-07 CN CNA2008100164951A patent/CN101289368A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8558036B2 (en) | 2010-11-15 | 2013-10-15 | Saudi Arabian Oil Company | Dual phase catalysts system for mixed olefin hydrations |
| US8865951B2 (en) | 2010-11-15 | 2014-10-21 | Saudi Arabian Oil Company | Dual phase catalysts system for mixed olefin hydrations |
| US9056315B2 (en) | 2010-11-15 | 2015-06-16 | Saudi Arabian Oil Company | Dual phase catalysts system for mixed olefin hydrations |
| CN102659514A (en) * | 2012-04-26 | 2012-09-12 | 凯瑞化工股份有限公司 | Method for producing sec-butyl alcohol |
| CN106669375A (en) * | 2015-11-09 | 2017-05-17 | 中国石油化工股份有限公司 | Process for treating tail gases of methyl ethyl ketone unit |
| CN107459442A (en) * | 2016-06-03 | 2017-12-12 | 中国石油化工股份有限公司 | A kind of sec-butyl alcohol process units and technique |
| CN108003018A (en) * | 2017-12-26 | 2018-05-08 | 浙江新和成股份有限公司 | A kind of method and its equipment for preparing cyclopentanol at supercritical conditions |
| CN108003018B (en) * | 2017-12-26 | 2021-01-15 | 浙江新和成股份有限公司 | Method and equipment for preparing cyclopentanol under supercritical condition |
| CN113165996A (en) * | 2018-11-20 | 2021-07-23 | 沙特基础工业全球技术有限公司 | Method and system for producing ethylene and at least one of butanol and alkyl tertiary butyl ether |
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