CN100413837C - Process for separating methylisobutanone synthesized from acetone - Google Patents
Process for separating methylisobutanone synthesized from acetone Download PDFInfo
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- CN100413837C CN100413837C CNB2005100474598A CN200510047459A CN100413837C CN 100413837 C CN100413837 C CN 100413837C CN B2005100474598 A CNB2005100474598 A CN B2005100474598A CN 200510047459 A CN200510047459 A CN 200510047459A CN 100413837 C CN100413837 C CN 100413837C
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Abstract
The invention discloses a separating method of methyl isobutyl ketone synthesized by acetone, which is characterized by the following: increasing acetone extracting and recycling step based on four-tower flow path; recycling acetone in the 2-methyl pantane/acetone azeotropic material; reducing the consumption of acetone and manufacturing cost; improving product competitive power and economic benefit.
Description
Technical field
The present invention relates to a kind of separation method by acetone (AC) synthesize methyl-isobutyl ketone (MIBK), this method has characteristics such as acetone rate of recovery height, raw material consumption be low.
Background technology
Methyl iso-butyl ketone (MIBK) (english abbreviation MIBK) is a kind of fine solvent of mid-boiling point, and it is the important derivatives of acetone, and is very extensive in aspect purposes such as oil refining, chemical industry.
The production method that MIBK is traditional is the acetone three-step approach.Be the first step, two molecule acetone generate a part Pyranton (DAA) under the basic catalyst effect; In second step, a part DAA dewaters under an acidic catalyst effect and generates mesityl oxide (MO); In the 3rd step, MO generates MIBK under the selective hydrogenation catalyst effect.Concrete reaction formula is as follows:
The first step: 2CH
3COCH
3→ (CH
3)
2COHCH
2COCH
3(1)
Second step: (CH
3)
2COHCH
2COCH
3→ (CH
3)
2C=CHCOCH
3+ H
2O (2)
The 3rd step: (CH
3)
2C=CHCOCH
3+ H
2→ (CH
3)
2CHCH
2COCH
3(3)
The synthetic MIBK technology of acetone single stage method is that nineteen sixty-eight is industrialized, sixties end, Germany Texaco lnc. develops a kind of new catalyst, this catalyzer has the condensation dehydration, hydrogenation is difunctional, make finish above-mentioned one step of three-step reaction, before this two molecule acetone condensation and dehydration generation MO on the acid site of catalyzer; Then, MO rapid in the heart hydrogenation in the hydrogenation of catalyzer generates MIBK.Reaction process can be represented by the formula:
Because dual-function catalyst has the condensation dehydration, hydrogenation is difunctional, therefore, also there is a spot of side reaction to take place simultaneously in the generation main reaction, main side reaction is specific as follows:
3CH
3COCH
3-→C
6H
3(CH
3)
3+3H
2O (5)
Sym-trimethylbenzene
(1,3,5-trimethyl benzene is called for short TMB)
CH
3COCH
3+H
2+(CH
3)
2CHCH
2COCH
3-→(CH
3)
2CHCH
2COCH
2CH(CH
3)
2 (6)
Diisobutyl ketone
(diisobutyl ketone is called for short DIBK)
H
2+(CH
3)
2CHCH
2COCH
3-→(CH
3)
2CHCH
2CH
2CH
3+H
2O (7)
The 2-methylpentane
(2-methyl penane is called for short 2-MPA)
Document 1 (Nanjing petrochemical complex, 25) and 2 (Nanjing petrochemical compleies 1,997 1987 (5):, 3:14) West Germany Hibernia company production technique and day Bender mountain Cao Da company production technique have been introduced, separation process in these two company's production technique is basic identical, all be to adopt three-column process flow, be that first tower is the acetone recovery tower, the acetone recycling use that reaction is excessive; Second tower is the MIBK dehydration tower, and water and MIBK azeotropic that reaction generates are removed water with the azeotrope form; The 3rd tower is the product tower, and cat head goes out product, and the tower still goes out heavy component.
When producing, find two large problems: 1, lack 2-methylpentane (2-MPA) tower by above-mentioned separation process tissue.Under the normal reaction situation, have in the reaction solution＜2-MPA of 1.0wt%, press the three-column process flow that document introduces and separate, no 2-methylpentane tower, the 2-methylpentane can not be told from system, can only be entrained in the acetone in system circulation and accumulates.At the production initial stage, during 2-MPA in the cycle stock＜1.0wt%, production is not constituted the influence of stopping work, along with continuous production time lengthening, when 2-MPA in the recycle stock＞1.0wt%, 2-MPA and acetone form azeotrope, steam from cat head, and this moment, tower top temperature no longer are 56 ℃ of original acetone boiling points, but 47 ℃ of the two azeotropic temperatures, so far change the original design operational condition and the purposes of tower fully, and then caused acetone to residue in a large number in the tower still, caused separation system to stop work at last.2, product (MIBK) purity low (about 98.5wt%～99.3wt%), use range is restricted.DAA about 1.0wt% is arranged in the product, and its boiling point is 168 ℃, but its feature is easily to decompose down at 95 ℃.Its operational condition of She Ji dehydration tower is 88 ℃ of cats head routinely, it is water-MIBK azeotropic temperature, at the bottom of the tower be 120 ℃, DAA in the reaction solution has only part to resolve into acetone like this, steams from the dehydration cat head, and some undecomposed DAA is brought in the MIBK product tower, and resolve into acetone therein, along with MIBK steams from cat head, cause the purity of product MIBK between 98.5wt%～99.3wt%, to fluctuate like this, purity is difficult to reach more than the 99.5wt%.Because product purity is restricted, its use range also is subjected to great influence.
Document 2 (Nanjing petrochemical complex 1997,3:14) introduced a kind ofly by the synthetic MIBK production technique of acetone single stage method, it is separated into four-column process flow, has increased a 2-MPA tower, this separation process has solved first problem in the problems referred to above preferably, but second problem still exists.
Document 3 (CN 1331070A) improves the MIBK dehydration tower at existing second problem in document 1 flow process, solves existing second problem in document 1 flow process preferably.
In the period of 1985～2000, domestic acetone price is many to be moved between 3000～5000 yuan/t, and the acetone price is more cheap, and this moment, the MIBK market demand was 1000～2000t/a, domestic have only two cover acetone single stage method to synthesize the MIBK production equipment, and scale is 1000t/a.Organized production by the separation process of document 3 at that time, 2-methylpentane/acetone azeotrope absolute yield is few, and it is taked to sell as fuel outside (1); (2) outer two kinds of processing modes of selling as usual vehicle, its flow process is also comparatively reasonable.But, after 2000, Chemical market alters a great deal, especially after 2002, the acetone price rises to 9500～10800 yuan/t, the domestic MIBK market requirement has also risen to 4.0 ten thousand t/a simultaneously, at this moment the economic scale of MIBK production equipment is 1.0 ten thousand tons of/year MIBK, pressing the separation process tissue of document 3 this moment again produces, its flow process just exposes a new shortcoming: the not recycling use of acetone in 2-methylpentane/acetone azeotrope, cause raw material acetone unit consumption height, products production cost height, competitive power of product is poor.
Summary of the invention
The objective of the invention is to, do not recycle at the acetone in 2-methylpentane/acetone azeotrope in the prior art, cause raw material acetone to consume high problem, a kind of improved products separation method is provided, with the consumption of reduction acetone, thereby reduce production cost of products.
Technical scheme of the present invention is as follows:
Reaction raw materials acetone reacts under the condition of hydrogen-containing gas and catalyzer existence, reactant is told hydrogen-containing gas through gas-liquid separator, remaining liquid is again through after cooling, at first enter 2-methylpentane tower, 2-methylpentane and acetone steam (its theoretical azeotrope consists of the 2-methylpentane of 56wt% and the acetone of 44wt% under the normal pressure) with the form of azeotrope from cat head, and still liquid enters the acetone recovery tower.In the acetone recovery tower, the acetone that reacts excessive reclaims cat head from acetone and steams, and is circulated to reactive system; Still liquid enters in first phase separator, tells water and oil phase, and water goes out device, and oil phase enters in the MIBK dehydration tower.In described MIBK dehydration tower, (azeotrope consists of the methyl iso-butyl ketone (MIBK) of 75wt% under its normal pressure with azeotrope for water and methyl iso-butyl ketone (MIBK), the water of 25wt%) form is after cat head steams, enter in second phase separator, after phase-splitting, oil phase is as the backflow of described MIBK dehydration tower, and water flows out carrying device by second phase separator bottom.Described MIBK dehydration tower bottoms enters in the methyl iso-butyl ketone (MIBK) tower, and methyl iso-butyl ketone (MIBK) steams from cat head, and the reorganization fractionation is in still liquid.
Described reorganization is divided into the mixture of diisobutyl ketone (DIBK) and sym-trimethylbenzene (TMB).
The invention is characterized in, on the basis of existing method, increase extraction recycling step to acetone, the azeotrope (2-methylpentane/acetone) that the 2-MPA column overhead is come out separates to reclaim acetone, the process that described acetone extract reclaims is: the azeotrope that the 2-MPA cat head comes out at first enters the extraction plant water and extracts, in phase separator, the extraction mixed solution is carried out phase-splitting then, the oil phase of telling (2-methylpentane) directly goes out device, and the water of telling (mixture of water and acetone) is waited until further processing.
The above-mentioned water of telling can further take following method to handle: can direct cycle to acetone recovery tower opening for feed, after the next mixing of materials of 2-methylpentane tower bottom, enter the acetone recovery tower; The water of perhaps telling is introduced into thick dehydration tower and dewaters, and the acetone after the dehydration is circulated to (containing acetone 95wt%, water 5wt%) opening for feed of acetone recovery tower, after the next mixing of materials of 2-methylpentane tower bottom, enters the acetone recovery tower; Isolated water also can be introduced into smart dehydration tower and dewater, and the acetone after the dehydration (moisture less than 0.5wt%) direct cycles to the opening for feed of reactive system.
Extraction recited above is to utilize the character that acetone and water can arbitrary proportion dissolve each other to carry out, and employed extraction plant can be conventional extraction tower, also can be stirring tank, and the weight ratio of described feed solution and water is 1: 1～1: 0.2.The used acetone extract agent of the present invention can be a water, can also be other can dissolve each other with acetone and with the insoluble solvent of 2-MPA.
Compared with prior art, advantage of the present invention is:
Only need increase less investment and can realize purpose of the present invention, and this separation process belongs to low consumption, saving type system.This separation process is when guaranteeing quality product, acetone separation in 2-methylpentane/acetone azeotrope is come out and recycled, reduce the consumption of reaction raw materials acetone, thereby reduced production cost of products, improved competitiveness of product and economic benefit of enterprises.
Description of drawings
Fig. 1 is the principle flow chart of separation method of the present invention.
Embodiment
Further describe technical scheme of the present invention below in conjunction with accompanying drawing and specific embodiment:
Embodiment 1
The flow process that embodiment taked is the flow process that scheme two is introduced.
1, the raw materials used situation of embodiment
The raw material that table 1 is delivered to separation system by reactive system is formed.
Table 1 raw material is formed
| Title | Form wt% |
| H 2O | 5.76 |
| 2-MPA | 0.35 |
| AC | 63.04 |
| MIBK | 29.00 |
| DAA | 0.25 |
| DIBK | 1.10 |
| TMB | 0.50 |
2, flow process briefing
The material of coming from reactive system is introduced into 2-methylpentane tower 1, and 2-methylpentane and acetone azeotropic, 2-methylpentane steam from cat head with the azeotrope form that (the azeotrope theory under tower 1 normal pressure consists of the 2-methylpentane of 56wt% and the acetone of 44wt%; In experimental implementation, azeotrope consists of the 2-methylpentane of 25wt% and the acetone of 75wt%); Still liquid is delivered to acetone recovery tower 2.In the acetone recovery tower 2, the acetone that reacts excessive reclaims cat head from acetone and steams, and is circulated to reactive system; Still liquid enters in the phase separator 3, and after phase-splitting, (contain MIBK＜1.0wt%) send the waste water treatment plant to reclaim MIBK to water; Oil phase is delivered in the MIBK dehydration tower 4.In MIBK dehydration tower 4, water and methyl iso-butyl ketone (MIBK) steam from cat head with the form of azeotrope that (azeotrope consists of the methyl iso-butyl ketone (MIBK) of 75wt% under its normal pressure, the water of 25wt%), enter in the phase separator 5, after phase-splitting, oil phase is as the backflow of described MIBK dehydration tower 4, and water (contains MIBK＜1.0wt%) flowed out by second phase separator 5 bottom, send the waste water treatment plant to reclaim MIBK.MIBK dehydration tower bottoms enters in the methyl iso-butyl ketone (MIBK) tower 6, and methyl iso-butyl ketone (MIBK) steams from cat head, and heavy component stays in still liquid.
2-methylpentane/acetone the azeotropic mixture that steams from 2-methylpentane column overhead enters the acetone extract tower 7, and the extraction mixed solution is delivered in the phase separator 8 and separated, and the oil phase of telling (2-methylpentane) flows out from phase separator 8 tops, carrying device; The water of telling (mixture of water and acetone) is delivered in the acetone dehydration tower 9, and acetone is carried out thick processed.The acetone that steams from tower 9 tops (acetone 95wt%, water 5wt%) is delivered to the opening for feed of acetone recovery tower 2, and the mixing of materials with 2-methylpentane tower 1 bottom is come enters into acetone recovery tower 2 afterwards.
3, each tower operational condition
Each tower detail operations condition of separation system sees Table 2.
Each tower operational condition of table 2 separation system
4, separating resulting
4.1 2-methylpentane tower
This tower effect is to slough 2-MPA.Feed composition sees Table 1.
2-methylpentane and acetone azeotropic, azeotropic temperature are 47 ℃, and the 2-methylpentane steams from cat head with the azeotrope form, and azeotrope consists of 2-MPA 25wt%, acetone 75wt% (normal pressure).The still liquid of 2-MPA tower consists of: H
2O 5.84wt%, AC 62.87wt%, MIBK 29.41wt%, DIBK 1.12wt%, TMB 0.51wt%, DAA 0.25wt%.
4.2, the acetone recovery tower
This tower effect is with unreacted acetone recycling use.The still liquid of 2-methylpentane tower consists of the composition of this tower charging.
Remove 2-methylpentane material afterwards and be sent in the acetone recovery tower, in this tower, acetone steams from cat head, purity＞99.5wt%, and all the other are water; Still liquid does not contain acetone as far as possible, and AC＜0.5w% impacts later separation MIBK preventing, the water that reaction simultaneously generates residues in the tower still of this tower as far as possible.Still liquid is sent in the phase separator 3, and after phase-splitting, water is delivered to the waste water treatment plant, and wherein water only accounts for the 10wt%～15wt% of oil phase; Oil phase is delivered in the MIBK dehydration tower 4, and its oil phase consists of: H
2O 0.70wt%, acetone 0.23wt%, MIBK 93.08wt%, DAA 0.81wt%, heavy component: DIBK are 3.56wt%, TMB is 1.62wt%.
4.3, the MIBK dehydration tower
This tower effect is the H that sloughs in the charging
2O and DAA.It is exactly this tower feed composition that the oil phase of phase separator 3 extraction is formed.
In this tower, water and MIBK azeotropic, azeotrope quantity seldom only accounts for charging 5.0wt%, consists of: MIBK＜5wt%, all the other are H
2O; DAA resolves into acetone in this tower simultaneously, and steams from cat head in the lump with azeotrope, after cooling, enter in the phase separator 5, and after phase-splitting, oil phase (MIBK 53wt%, AC 40wt%, H
2O 7.0wt%, normal pressure) as the backflow of this tower; Water (contains MIBK 1.0wt%, H
2O 98wt%, all the other are AC) send the waste water treatment plant to reclaim MIBK and AC.This tower bottoms is delivered to the product tower, and it consists of: H
2O0.11wt%, AC 0.01wt%, MIBK94.64wt%, heavy component: DIBK are 3.59wt%, TMB is 1.63wt%.
4.4, MIBK product tower
Take off H through MIBK
2The material that the O tower was handled enters into MIBK product tower 6, carries out atmospheric distillation.Cat head obtains the above product of purity 99.5wt%, and heavy component residues in the tower, and tower still component is: MIBK1.03wt%, DIBK 67.18wt%, TMB 31.79wt%.Tower still heavy component purposes has two, can be used as printing ink solvent first; Second can be used as boiler oil.
4.5, the acetone extract tower
This tower effect is a character of utilizing acetone and water can arbitrary proportion to dissolve each other, and water extracts acetone (2-MPA/AC) from azeotrope.The azeotrope that 2-methylpentane column overhead steams consists of: 2-MPA 25wt%, acetone 75wt% (normal pressure) for the charging of this tower.
Discharging consists of at the bottom of this Tata: 2-MPA 12.5wt%, AC 37.5wt%, water 50wt%.This material enters into phase separator 8, carries out oil/moisture phase, and wherein oil phase accounts for 12.5wt%, consists of: 2-MPA 99.5wt%, AC 0.50wt%; Water accounts for 87.5wt%, consists of: AC 42.8wt%, water 57.2wt%.
4.6, the acetone dehydration tower
The water that phase separator 8 is told is exactly the charging of this tower, and composition is: AC 42.8wt%, water 57.2wt%.The effect of this tower is: acetone is carried out thick processed, make the moisture reduction greatly of acetone, can reduce the production load of acetone recovery tower 2 and MIBK dehydration tower 4 like this; Also can reduce the fluctuation of acetone recovery tower and MIBK dehydration tower feed composition in addition, be beneficial to the steady running of a whole set of separation system.
The acetone purity that this column overhead steams is greater than 95w%, and all the other are water; Discharging is at the bottom of the tower: water is greater than 99.5w%, and all the other are acetone, and this material is delivered to the waste water treatment plant, reclaims acetone treatment.
By the introduction of above-mentioned flow process situation and separating resulting as can be known, this separation process has little, the energy efficient of investment, characteristics such as acetone rate of recovery height.In 10,000 tons of/year MIBK production equipments, if adopt separation process of the present invention, can reclaim 450 tons in acetone every year more, if, can be enterprise every year by present 10000 yuan/ton, acetone increases income 4,500,000 yuan.Therefore, use technical scheme of the present invention, can reduce the production cost of MIBK, product has more the market competitiveness.
Claims (6)
1. separation method by methylisobutanone synthesized from acetone, reaction raw materials acetone reacts under the condition of hydrogen-containing gas and catalyzer existence, reactant is told hydrogen-containing gas through gas-liquid separator, remaining liquid is again after the supercooler cooling, at first enter 2-methylpentane tower (1), 2-methylpentane and acetone steam from tower (1) top with the form of azeotrope, still liquid enters acetone recovery tower (2), the acetone that reacts excessive steams from tower (2) top, be circulated to reactive system, still liquid enters phase separator (3) to be separated, water is told by separator (3) bottom, oil phase enters in the methyl iso-butyl ketone (MIBK) dehydration tower (4), water and methyl iso-butyl ketone (MIBK) steam and enter the phase separator (5) from tower (4) top with the form of azeotrope, after phase-splitting, oil phase is as the backflow of methyl iso-butyl ketone (MIBK) dehydration tower (4), water is told by phase separator (5) bottom, methyl iso-butyl ketone (MIBK) dehydration tower (4) still liquid enters in the methyl iso-butyl ketone (MIBK) tower (6), methyl iso-butyl ketone (MIBK) steams from tower (6) top, and the reorganization fractionation is in still liquid; It is characterized in that 2-methylpentane tower (1) ejects the azeotrope that comes and at first enters extraction plant (7) and extract, in phase separator (8) the extraction mixed solution is carried out phase-splitting then, isolated oil phase goes out device, and isolated water is waited until further processing.
2. separation method according to claim 1 is characterized in that, the water that described phase separator (8) is told direct cycles to the opening for feed of acetone recovery tower (2).
3. separation method according to claim 1 is characterized in that, the water that described phase separator (8) is told enters thick dehydration tower (9) and dewaters, and the acetone recycle after the dehydration is to the opening for feed of acetone recovery tower (2).
4. separation method according to claim 1 is characterized in that, the water that described phase separator (8) is told enters smart dehydration tower (10) and dewaters, and the acetone recycle after the dehydration is returned the opening for feed of reactive system.
5. according to the arbitrary described separation method of claim 1-4, it is characterized in that described extraction plant is extraction tower or stirring tank.
6. according to the arbitrary described separation method of claim 1-4, it is characterized in that the condition of described extraction is: the weight ratio of feed solution and water is 1: 1～1: 0.2.
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Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101376623B (en) * | 2007-08-31 | 2011-04-20 | 中国石油天然气股份有限公司 | Separation method of methyl isobutyl ketone synthetic liquid |
| CN102050713B (en) * | 2009-10-27 | 2013-07-24 | 中国石油化工股份有限公司 | Device and method for producing methyl isobutyl ketone (MIBK) by using acetone (AC) |
| CN102249877B (en) * | 2011-06-13 | 2013-06-12 | 中国石油化工股份有限公司 | Method for producing 4-methyl-2-pentanone by using production waste and residual liquor |
| CN103301717B (en) * | 2013-05-03 | 2015-04-15 | 珠海醋酸纤维有限公司 | Double-tower integrated recovery device and method for micro-acetone-contained air |
| CN105130778B (en) * | 2015-08-31 | 2016-09-14 | 宁波镇洋化工发展有限公司 | A kind of production technology of methyl iso-butyl ketone (MIBK) |
| CN108084008B (en) * | 2016-11-19 | 2020-10-27 | 中国石油化工股份有限公司 | Start-up method for process for synthesizing methyl isobutyl ketone by acetone one-step method |
| CN110054556A (en) * | 2019-03-14 | 2019-07-26 | 镇江李长荣高性能材料有限公司 | A kind of novel hexone dewatering process |
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| CN1331070A (en) * | 2000-06-28 | 2002-01-16 | 中国石油化工集团公司 | Process for separating methylisobutanone synthesized from acetone |
| CN1488617A (en) * | 2002-10-10 | 2004-04-14 | 中国石油化工股份有限公司 | Method for synthesizing methyl isobutyl ketone/methyl isobutyl alcohol |
| CN1566059A (en) * | 2003-07-03 | 2005-01-19 | 中国科学院兰州化学物理研究所 | Technological process for one-step synthesizing methyl isobutyl ketone by catalyzing acetone |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1331070A (en) * | 2000-06-28 | 2002-01-16 | 中国石油化工集团公司 | Process for separating methylisobutanone synthesized from acetone |
| CN1488617A (en) * | 2002-10-10 | 2004-04-14 | 中国石油化工股份有限公司 | Method for synthesizing methyl isobutyl ketone/methyl isobutyl alcohol |
| CN1566059A (en) * | 2003-07-03 | 2005-01-19 | 中国科学院兰州化学物理研究所 | Technological process for one-step synthesizing methyl isobutyl ketone by catalyzing acetone |
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