CN102826976B - Method for adjusting ratio of butyraldehyde to isobutyraldehyde in propylene catalytic preparation - Google Patents
Method for adjusting ratio of butyraldehyde to isobutyraldehyde in propylene catalytic preparation Download PDFInfo
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims abstract description 52
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 42
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 title claims abstract description 25
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title abstract 2
- 230000003197 catalytic effect Effects 0.000 title description 4
- 239000010948 rhodium Substances 0.000 claims abstract description 18
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 16
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 4
- 239000000047 product Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 19
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 11
- 238000006555 catalytic reaction Methods 0.000 claims description 7
- 230000008859 change Effects 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- RHKGZYVYKXVQSD-MECAPONASA-N [Rh].[O+]#[C-].C\C(O)=C\C(C)=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical group [Rh].[O+]#[C-].C\C(O)=C\C(C)=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RHKGZYVYKXVQSD-MECAPONASA-N 0.000 claims description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims description 3
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 claims 1
- 239000007789 gas Substances 0.000 abstract description 18
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- 0 *c1ccccc1-c1c(*)cccc1 Chemical compound *c1ccccc1-c1c(*)cccc1 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- SZKMTZNASRXXCE-UHFFFAOYSA-N [2-[2-(diphenylphosphanylmethyl)phenyl]phenyl]methyl-diphenylphosphane Chemical compound C=1C=CC=C(C=2C(=CC=CC=2)CP(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 SZKMTZNASRXXCE-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- -1 phosphorous acid ester Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- CMIHWILCIPLTFO-UHFFFAOYSA-N [1-[2-(diphenylphosphanylmethyl)naphthalen-1-yl]naphthalen-2-yl]methyl-diphenylphosphane Chemical compound C=1C=C2C=CC=CC2=C(C=2C3=CC=CC=C3C=CC=2CP(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 CMIHWILCIPLTFO-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000010523 cascade reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical class PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for adjusting the ratio of butyraldehyde to isobutyraldehyde in propylene catalystic preparation. The method comprises the steps of adjusting feed ratio of synthesis gases to propylene and changing excessive ratio of CO to the corresponding propylene to control the ratio of butyraldehyde to isobutyraldehyde in the product. Through the method provided by the invention, technical staffs in the field can control the ratio of butyraldehyde to isobutyraldehyde in the product to 5-12 during the hydroformylation of propylene conveniently; changes of a rhodium catalyst system in the production plant can be avoided so as to ensure the plant operation for a long period, so that the product composition can be adjusted timely according to the market demand when the long-period operation scheme in the plant is adopted.
Description
Technical field
The present invention relates to field of chemical technology, specifically, relate to one and utilize rhodium/triphenyl phosphine catalyst, propene hydroformylation reaction prepares the control method of the just different ratio of product of butyraldehyde.
Background technology
The hydroformylation reaction of alkene has important industrial significance; the product utilizing this reaction to produce and derived product reach millions of tons every year; the aldehydes wherein produced by olefine in low carbon number and derived product thereof account for the overwhelming majority; especially the so-called oil soluble system adopting rhodium/triphenylphosphine to be catalyzer is adopted by most of device, and therefore this production technology is subject to great attention.
" homogeneous catalysis " technology of industrial employing rhodium/phosphine complex catalysis system is also called low pressure oxo process technology, and the principal character of this kind of technology is by above-mentioned catalyst dissolution in a solvent, makes raw material olefin and synthetic gas (H
2/ CO) pass into catalyst solution continuously, control condition makes hydroformylation reaction carry out in liquid phase main body, is separated after reaction, subsequently unreacted raw material and catalyst solution is looped back reactor, product is sent into follow-up purification unit simultaneously.Obviously, hydroformylation reaction carries out in liquid phase main body, and as CO and H of raw material
2and the alkene of low carbon number is gaseous state at reaction conditions, therefore for ensureing that unstripped gas has enough concentration in the liquid phase, need CO, H of making in gas phase
2enough pressure is maintained with alkene.The impact of concentration on reaction result of different material is different on the other hand, needs the composition determining these compositions accordingly.
Existing many documents have carried out good summary and commentary to various technical scheme of the prior art.Representational document edits " RhodiumCatalyzed Hydroformylation " book jointly by P.W.N.M.Van Leeuwen and C.Claver.
The just different ratio of hydroformylation reaction product, namely the ratio of n-alkanal and isomery aldehyde is an important index in actual production, receives much concern.Although in general, the purposes of n-alkanal is more extensive, and along with the technical progress of petrochemical complex, the Application Areas of isomery aldehyde is also in expansion.Therefore change according to the market requirement, the product proportion of the positive isomery aldehyde of adjustment is very important flexibly.And at present along with the development of petrochemical technology, the maximization of device and the long-term operation of device are all the focuses paid close attention to, general device run continuously more than 5 years very common.By to changing part thus the method for the just different ratio of adjustment, will have a huge impact whole process, being complexity and uneconomic way.
If a kind of method that can control just different ratio in continuous hydroformylation process can be provided, play material impact by the kind of product, increase economic efficiency further.In the prior art, much describe about the influence factor affecting the just different ratio of pressure hydrogen formylation reaction is existing.
Wherein, for the hydroformylation reaction using catalyzer, the impact of catalyst structure on the just different ratio of product is most important, such as:
A series of biphosphine ligand NAPHOS is reported, BISBI, PHENAP in US Patent No. 4694109.Be applied in oneself rare hydroformylation reaction of 1-, these parts show suitable activity and high regioselectivity, and wherein BISBI is in very low phosphine/rhodium ratio (4 ~ 8: 1) situation, and just different ratio can reach 96: 4.
Chinese patent CN200610147735.2 discloses a kind of method, bis-phosphite is with the addition of in triaryl phosphine/rhodium catalytic system, the just different ratio of butyraldehyde in the activity of triaryl phosphine/rhodium catalyst and product can be significantly improved, and the life-span of significant prolongation bis-phosphite.
Chinese patent CN200810036777.8 discloses a kind of single phosphorous acid ester, bis-phosphite/rhodium catalytic system, the method compares the catalyst system being used alone a kind of phosphite ester ligand, in stability and selectivity, there is advantage, and can realize by regulating bis-phosphite to make just different ratio adjustable in certain limit with the ratio of single phosphorous acid ester.
In addition; a kind of technique of hydroformylation reaction is disclosed in US Patent No. 3527809; think that reaction stagnation pressure and CO dividing potential drop have a significant impact reaction; need to control reaction by control reaction stagnation pressure and CO dividing potential drop; the document thinks that reaction pressure should between 14.7psi ~ 450psi; preferably between 14.7 ~ 350psi, most preferably 14.7 ~ 250psi.Embodiment gives pressure when becoming 280 ~ 300psi from 80 ~ 100psi, and the just different ratio of product is reduced to 4.0 from 6.0, and document points out that CO dividing potential drop has great importance, when CO dividing potential drop reaches stagnation pressure (CO+H to the just different ratio of product simultaneously
2dividing potential drop and) 75% time, the just different ratio of product obviously reduces, and H
2dividing potential drop should between 25 ~ 90% of stagnation pressure, preferably between 45 ~ 75%.
Give in US Patent No. 4400548 at 130 DEG C, partial pressure of propylene aligns the impact of different ratio and speed of response, partial pressure of propylene is increased to 58.7psi from 55.30psi, and generate the speed of aldehyde between 1.67 ~ 1.88mol/hr*L, the just different ratio of product is between 9.9 ~ 10.2.
Obviously, although prior art has paid close attention to the impact of reaction conditions on the just different ratio of product, clearly do not proposed crucial influence factor, the impact of key factor has not been quantitatively described yet.
For above-mentioned defect, the object of this invention is to provide a kind of method by regulating the ratio of reactant to control positive isobutyric aldehyde ratio in the propylene producing butyladehyde process of rhodium/triphenyl phosphine catalyst.
Summary of the invention
For the proportion adjustment problem of isobutyric aldehyde positive in prior art, especially for the control by isobutyric aldehyde ratio positive in propylene producing butyladehyde process, the object of this invention is to provide the simple method that a kind of method by adjusting reactant ratio regulates the just different ratio of product, thus make production process more flexible.
The present inventor have extensively studied the reaction process utilizing propylene to prepare butyraldehyde, proposes the charge ratio by adjustment synthetic gas and propylene, changes CO and the excessive percentage of corresponding propylene, butyraldehyde-n in reaction product is controlled in required scope with the ratio of isobutyric aldehyde.
In detail, method of the present invention comprises the following steps:
1) according to the just different ratio of required butyraldehyde product, following model prediction CO and corresponding propylene excess is utilized;
N＝B
1R
3+B
2R
2+B
3R+B
4
In formula, N is molar excess percentage, and R is the required just different ratio of butyraldehyde product, and Bn is constant, wherein:
B
1＝-8.151×10
-5B
2＝2.570×10
-3B
3＝-2.843×10
-2B
4＝0.1218
2) inlet amount of CO is calculated according to following formula:
Described corresponding propylene refers to and reacts with CO and the propylene consumed;
3) according to step 2) excess that calculates, to calculate, adjustment synthetic gas inlet amount, the butyraldehyde product that obtained just different ratio is consistent with required just different ratio.
The large industrial manufacture process of a kind of continuous print due to what the present invention relates to, the influence factor of reaction result is various, and " unanimously " therefore described in present method refers to basically identical, but for a person skilled in the art, can reach the requirement of this area, realize object of the present invention.
Concerning specific technique and device, step 2) described in corresponding propylene be determine according to the reactivity of propylene, be the measured data of device; Therefore, before implementation method of the present invention, in fact in described step 1) before, the utilization ratio of the propylene of butyraldehyde technique is prepared in the propylene catalysis that described method also comprises mensuration rhodium/triphenyl phosphine catalyst, namely in the productive rate of the butyraldehyde of propylene.
In the raw materials used synthetic gas of above-mentioned reaction, CO and H
2mol ratio relatively fixing, generally its ratio is H
2/ CO=1.01 ~ 1.10, synthetic gas source has multiple, and use for laboratory is commercially available, technique be the method such as petroleum naphtha, water-gas conversion;
Wherein, described propylene producing butyladehyde process refers to propylene and synthetic gas (H
2/ CO) under rhodium/triphenylphosphine catalysis effect serialization carry out hydroformylation reaction and prepare the process of butyraldehyde.The formation of catalyzer is Rh (Acac) (CO) (PPh
3)/PPh
3wherein Acac is methyl ethyl diketone, is commercial reagent.
The reaction conditions of described propylene producing butyladehyde process is: temperature of reaction 353 ~ 393K, CO pressure component: 0.03 ~ 0.20MPa, H
2pressure component: 0.15 ~ 0.90MPa, partial pressure of propylene power: 0.08 ~ 0.80MPa, the concentration of catalyzer Rh is 100 ~ 300ppm, and triphenyl phosphorus concentration is 5.0 ~ 15.0wt%.
Step 1) in, described model, by testing above-mentioned tandem reaction sequence and carrying out mathematical regression to test data and obtain, is experimental formula.
Revision test repeatedly shows, adopts aforesaid method can obtain in following ranges desirable just different from result: excessive percentile variation range is 0.5% ~ 7%, preferably 0.5% ~ 4%; Then in described product, butyraldehyde-n is 3 ~ 15 with the ratio of isobutyric aldehyde, preferably 5 ~ 12.
By adopting method of the present invention, those skilled in the art can realize the regulation and control of just different ratio in 5 ~ 12 scopes of product in propene hydroformylation reaction process easily and flexibly; Avoid the change of rhodium catalytic system in production equipment, guarantee device long-term operation, therefore can adjust product composition timely according to the market requirement when device adopts long-term operation scheme.
Embodiment
Following examples for illustration of the present invention, but are not used for limiting the scope of the invention.As nothing specializes, the raw material adopted in embodiment is commercial.
Embodiment 1
Test in the reaction unit of the hydroformylation of propene producing butyladehyde of a set of continuous operation.The volume of reactor used is 2L, reactor is equipped with the opening for feed of propylene, synthetic gas and catalyzer and gas phase and liquid phase discharge port, turnover pipeline is equipped with measuring instrument and analytical sampling mouth.
Wherein propylene to be purity be 99.5% polymerization-grade propylene; The composition of synthetic gas is H
2/ CO=1.033mol ratio, the formation of catalyzer is Rh (Acac) (CO) (PPh
3)/PPh
3wherein Acac is methyl ethyl diketone, is commercial reagent.
Pass into synthetic gas and propylene continuously, its mol ratio can change with in the scope of the excessive percentage 0.5% ~ 7% of corresponding propylene at CO, and detect product, the yield stable of butyraldehyde is at 77.7% (in propylene);
Propylene and synthetic gas react generation butyraldehyde under rhodium/triphenyl phosphine catalyst effect and temperature 90 DEG C, pressure 1.9MPa condition in the reactor.Change synthetic gas charging proportioning and product analyzed, CO excess can be obtained as calculated just different as follows than data with product:
Carrying out mathematical regression according to as above experimental data, to obtain product just different as follows than predictive model:
N＝-8.151×10
-5R
3+2.570×10
-3R
2-2.843×10
-2R+0.1218
Embodiment 2
Test under the device identical with embodiment 1 and condition, for just different ratio is adjusted to 10: 1.Can calculate CO excess according to predictive model is 1.30%, then can calculate synthetic gas charging when propylene feed is 4.80mol/h according to analytical results and should be 7.64mol/h.Regulate charging proportioning accordingly, sampling analysis after system stability, obtaining the just different ratio of reality is 10.15.
Embodiment 3
Test under the device identical with embodiment 1 and condition, for just different ratio is adjusted to 5: 1.Can calculate CO excess according to predictive model is 3.37%, then can calculate synthetic gas charging when propylene feed is 4.80mol/h according to analytical results and should be 7.80mol/h.Regulate charging proportioning accordingly, sampling analysis after system stability, obtaining the just different ratio of reality is 5.03.
Claims (4)
1. one kind regulates the method being prepared the just different ratio of butyraldehyde product of butyraldehyde technique by propylene of rhodium/triphenyl phosphine catalyst, it is characterized in that, by adjusting the charge ratio of synthetic gas and propylene, change the excessive percentage of CO and corresponding propylene in synthetic gas, control butyraldehyde-n and the ratio of isobutyric aldehyde in reaction product, comprise the steps:
1) according to the just different ratio of required butyraldehyde product, following model prediction CO and corresponding propylene excess is utilized;
N＝B
1R
3+B
2R
2+B
3R+B
4
In formula, N is molar excess percentage, and R is the required just different ratio of butyraldehyde product, and Bn is constant, wherein:
B
1＝-8.151×10
-5B
2＝2.570×10
-3B
3＝-2.843×10
-2B
4＝0.1218
2) inlet amount of CO is calculated according to following formula:
Described corresponding propylene refers to and reacts with CO and the propylene consumed, and is the measured data of device;
3) according to step 2) excess that calculates, to calculate, adjustment synthetic gas inlet amount, the butyraldehyde product that obtained just different ratio is consistent with required just different ratio;
The reaction conditions that butyraldehyde is prepared in propylene catalysis is: temperature of reaction 353 ~ 393K, CO pressure component: 0.03 ~ 0.20MPa, H
2pressure component: 0.15 ~ 0.90MPa, partial pressure of propylene power: 0.08 ~ 0.80MPa, the concentration of catalyzer Rh is 100 ~ 300ppm, TPP concentration is 5.0 ~ 15.0wt%;
Described excessive percentile variation range is 0.5% ~ 7%, then in described product, butyraldehyde-n is 15 ~ 3 with the ratio of isobutyric aldehyde.
2. method according to claim 1, is characterized in that, in described step 1) before, the utilization ratio of the propylene of butyraldehyde technique prepared by the propylene that described method also comprises mensuration rhodium/triphenyl phosphine catalyst.
3. the method according to claim 1 ~ 2 any one, is characterized in that, described propylene catalysis is prepared butyraldehyde and referred to that the serialization under rhodium/triphenylphosphine catalysis effect of propylene and synthetic gas is carried out hydroformylation reaction and prepares the process of butyraldehyde; Wherein the formation of catalyzer is Rh (Acac) (CO) (PPh
3)/PPh
3, Acac is methyl ethyl diketone.
4. method according to claim 1, is characterized in that, described excessive percentile variation range is 0.5% ~ 4%, then in described product, butyraldehyde-n is 12 ~ 5 with the ratio of isobutyric aldehyde.
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| CN109456154A (en) * | 2018-11-14 | 2019-03-12 | 成都欣华源科技有限责任公司 | A method of fatty aldehyde is prepared by hydroformylation reaction |
| CN111646883A (en) * | 2019-03-04 | 2020-09-11 | 内蒙古伊泰煤基新材料研究院有限公司 | Method for preparing aldehyde by hydroformylation of low-carbon olefin |
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|---|---|---|---|---|
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| US4287369A (en) * | 1979-03-21 | 1981-09-01 | Davy Mckee (Oil & Chemicals) Limited | Hydroformylation of alkenes to aldehydes |
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-
2011
- 2011-06-17 CN CN201110163717.4A patent/CN102826976B/en active Active
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| CN1400961A (en) * | 2000-02-14 | 2003-03-05 | 巴斯福股份公司 | Method for processing a liquid hydroformylation discharge |
| CN1863595A (en) * | 2004-06-12 | 2006-11-15 | Lg化学株式会社 | Phosphorus-containing catalyst composition and hydroformylation process using the same |
| CN101610843A (en) * | 2006-12-21 | 2009-12-23 | 伊士曼化工公司 | Phosphonite-containing catalysts for hydroformylation processes |
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|---|
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