CN107840781B - Method for preparing isopentenol from 2-methyl-3-buten-2 alcohol - Google Patents
Method for preparing isopentenol from 2-methyl-3-buten-2 alcohol Download PDFInfo
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- CN107840781B CN107840781B CN201710944129.1A CN201710944129A CN107840781B CN 107840781 B CN107840781 B CN 107840781B CN 201710944129 A CN201710944129 A CN 201710944129A CN 107840781 B CN107840781 B CN 107840781B
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- 238000000034 method Methods 0.000 title claims abstract description 23
- QVDTXNVYSHVCGW-ONEGZZNKSA-N isopentenol Chemical compound CC(C)\C=C\O QVDTXNVYSHVCGW-ONEGZZNKSA-N 0.000 title claims abstract description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 8
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 claims abstract description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- BZAZNULYLRVMSW-UHFFFAOYSA-N 2-Methyl-2-buten-3-ol Natural products CC(C)=C(C)O BZAZNULYLRVMSW-UHFFFAOYSA-N 0.000 claims abstract description 25
- 230000002378 acidificating effect Effects 0.000 claims abstract description 21
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 15
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 29
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 claims description 16
- -1 isoamylene alcohol Chemical compound 0.000 claims description 14
- 239000012043 crude product Substances 0.000 claims description 12
- 238000007670 refining Methods 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000003729 cation exchange resin Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- 239000002994 raw material Substances 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 4
- 238000010924 continuous production Methods 0.000 abstract description 3
- 230000007547 defect Effects 0.000 abstract description 3
- 239000012752 auxiliary agent Substances 0.000 abstract description 2
- 238000009835 boiling Methods 0.000 abstract description 2
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 6
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 3
- MXVSJNLRVLKAOG-UHFFFAOYSA-N 1-chloro-3-methylbut-1-ene Chemical compound CC(C)C=CCl MXVSJNLRVLKAOG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- NSPPRYXGGYQMPY-UHFFFAOYSA-N 3-Methylbuten-2-ol-1 Natural products CC(C)C(O)=C NSPPRYXGGYQMPY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XPVUBPISXXCAGT-UHFFFAOYSA-N formaldehyde 2-methylprop-1-ene Chemical compound O=C.CC(C)=C XPVUBPISXXCAGT-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing isopentenol from 2-methyl-3-buten-2-ol, which does not introduce an organic solvent and reduces the separation difficulty, wherein the 2-methyl-3-buten-2-ol is partially converted into the isopentenol under the action of solid acidic ion exchange resin and water serving as an auxiliary agent, reaction materials are easy to separate from a catalyst, the separated materials are rectified to remove the isopentenol with higher boiling point, the unconverted 2-methyl-3-buten-2-ol and the auxiliary water can be input into a reaction system again for continuous isomerization reaction, the process flow is simpler, and the continuous production is easy to realize; the catalyst acid ion exchange resin is low in price and easy to obtain, and has popularization value; in addition, the reaction can inhibit the dehydration reaction of the raw materials and the products to a certain extent in the presence of water, improve the reaction selectivity and overcome the defect that other processes have strict requirements on the water content of the raw materials.
Description
The technical field is as follows:
the invention relates to a method for preparing isopentenol from 2-methyl-3-buten-2 alcohol.
Background art:
the chemical name of the prenol is 3-methyl-2-buten-1-ol, is colorless and transparent liquid with concentrated ester fragrance, is an important intermediate for synthesizing products such as spices, medicines, pesticides and the like, and is also an important raw material for synthesizing rubber. At present, the main process routes for industrially synthesizing the prenol comprise: chlorinated isoamylene hydrolysis process (esterification hydrolysis and direct hydrolysis) and isobutene-formaldehyde condensation process.
Although the isopentenol can be directly obtained by the esterification and hydrolysis processes of the chloroisopentene, the production cost is high and the environmental pollution is serious. The direct hydrolysis method of the chloroisopentene can obtain a mixture of 2-methyl-3-butene-2-alcohol and isopentenol, but the 2-methyl-3-butene-2-alcohol also needs to be isomerized to obtain the isopentenol.
In addition, patent document CN102391073B describes a production method for converting 2-methyl-3-buten-2-ol into isopentenol under the action of phosphoric acid, which is operated intermittently, the conversion rate is only about 20%, and the defects of severe corrosion of equipment, neutralization treatment of the catalyst, more generation of three wastes and the like exist. Patent document CN101381283A provides a method for producing isopentenol from 2-methyl-3-buten-2-ol without solvent under the action of rhenium, tungsten and vanadium catalysts, and the continuous process has high requirements for raw material moisture, high reaction temperature and pressure, and the catalysts are expensive and large in one-time investment. Patent document US4028424 proposes a process in which isobutene is condensed with formaldehyde to give 3-methyl-3-buten-1-ol, which is converted to isopentenol under the action of a palladium-containing catalyst in a hydrogen atmosphere. The process comprehensively utilizes the isobutene component in the C4 fraction, but the method obtains the intermediate 3-methyl-3-butylene-1-alcohol under the conditions of high temperature and high pressure, the reaction conditions are severe, and the equipment investment is large. Isobutene condenses with formaldehyde to form mainly 3-methyl-3-buten-1-ol, and additionally 3-methyl-3-buten-1-ol must be isomerized to give prenol.
The invention content is as follows:
the invention aims to solve the problems in the prior art and provides a method for partially isomerizing 2-methyl-3-butene-2-ol to generate isopentenol under the action of water and acidic ion exchange resin.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a process for the preparation of prenol from 2-methyl-3-buten-2 alcohol comprising the steps of: preheating a mixture of 2-methyl-3-buten-2-ol and water, feeding the mixture into a fixed bed reactor filled with acidic ion exchange resin as a catalyst, carrying out isomerization reaction to obtain a mixture of 2-methyl-3-buten-2-ol, isoamylene alcohol and water, separating the mixture by using a rectifying tower, obtaining a reusable mixture of 2-methyl-3-buten-2-ol and water at the tower top, obtaining a crude product of isoamylene alcohol at the tower bottom, and refining the crude product of the isoamylene alcohol by using a refining tower to obtain a finished product of the isoamylene alcohol.
Further, the acidic ion exchange resin is a strongly acidic resin, a weakly acidic resin or a combination of the strongly acidic resin and the weakly acidic resin.
Further, the acidic ion exchange resin is macroporous strong-acid styrene type cation exchange resin, and the mass space velocity in the fixed bed reactor is 0.5-5 h < -1 >.
Further, the temperature of the fixed bed reactor is 40-90 ℃, and the pressure is normal pressure.
Further, the temperature of the fixed bed reactor is 55-70 ℃.
Further, the mass ratio of the 2-methyl-3-buten-2-ol to the water in the mixture fed to the fixed bed reactor is as follows: 0.5-10: 1.
further, the mass ratio of the 2-methyl-3-buten-2-ol to the water in the mixture fed into the fixed bed reactor is 1-3: 1.
further, the mixture of 2-methyl-3-butene-2-ol, isoamylene alcohol and water obtained by isomerization reaction is separated by a rectifying tower with 20 theoretical plates in a stripping section and a rectifying section respectively, the reflux ratio of the tower top is controlled to be 1:1, and the mixture of the 2-methyl-3-butene-2-ol and the water is obtained and is input into a fixed bed reactor for reutilization.
Further, the tower kettle obtains a crude product of the prenol, and the crude product is sent into a refining tower with 15 theoretical plates in a stripping section and a rectifying section respectively for refining, so that a finished product of the prenol with the content of more than 98.5% is obtained.
The invention has the beneficial effects that: the method for preparing the isopentenol from the 2-methyl-3-buten-2 alcohol does not introduce an organic solvent, reduces the separation difficulty, partially converts the 2-methyl-3-buten-2 alcohol into the isopentenol under the action of solid acidic ion exchange resin and water as an auxiliary agent, easily separates reaction materials from a catalyst, rectifies the separated materials to remove the isopentenol with higher boiling point, and can input the unconverted 2-methyl-3-buten-2 alcohol and the auxiliary water into a reaction system again to continue the isomerization reaction, so that the process flow is simple and the continuous production is easy to realize; the catalyst acid ion exchange resin is low in price and easy to obtain, and has popularization value; in addition, the reaction can inhibit the dehydration reaction of the raw materials and the products to a certain extent in the presence of water, improve the reaction selectivity and overcome the defect that other processes have strict requirements on the water content of the raw materials.
Description of the drawings:
FIG. 1 is a schematic view showing the structure of a reaction and separation apparatus used in the present invention.
The specific implementation mode is as follows:
the following detailed description of embodiments of the invention refers to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
The process for preparing prenol from 2-methyl-3-buten-2-ol according to the present invention as shown in FIG. 1 consists of two major steps of reaction and separation, comprising the steps of: preheating a mixture of 2-methyl-3-buten-2-ol and water, feeding the mixture into a fixed bed reactor 2 filled with acidic ion exchange resin as a catalyst, carrying out isomerization reaction to obtain a mixture of 2-methyl-3-buten-2-ol, isoamylene alcohol and water, separating the mixture by using a rectifying tower 3, obtaining a mixture of 2-methyl-3-buten-2-ol and water which can be reused at the tower top, obtaining a crude product of isoamylene alcohol at the tower bottom, and refining the crude product of the isoamylene alcohol by using a refining tower 4 to obtain a finished product of the isoamylene alcohol.
The fixed bed reactor 2 can be a metal tube with diameter of 50mm multiplied by 3000mm and a PTFE lining, acidic ion exchange resin is filled in the metal tube, the acidic ion exchange resin can be strong acid (such as sulfonic group) resin, weak acid (such as carboxyl group) resin or the combination of the strong acid resin and the weak acid resin, as a preferred scheme, D001 macroporous strong acid styrene type cation exchange resin with particle size of 3-5 mm can be filled, the cation exchange resin is activated by strong acid to form H type, and the total amount is 2000g after drying. The mixture of 2-methyl-3-buten-2-ol and water is preheated by a preheater 1 and continuously fed into a fixed bed reactor 2, and the reaction temperature is controlled by controlling the preheating temperature of the raw materials. The mass ratio of the 2-methyl-3-buten-2-ol to the water in the mixture fed into the fixed bed reactor 2 is as follows: 0.5-10: 1, preferably, the mass ratio of the 2-methyl-3-buten-2-ol to the water in the mixture fed to the fixed bed reactor 2 is: 1-3: 1. when the acidic ion exchange resin is macroporous strong-acid styrene type cation exchange resin, the mass airspeed in the fixed bed reactor 2 is preferably 0.5-5 h < -1 >. The temperature of the fixed bed reactor 2 is 40-90 ℃, the pressure is normal pressure, and preferably, the temperature of the fixed bed reactor 2 is 55-70 ℃.
After isomerization reaction, part of 2-methyl-3-butene-2-ol is converted into isopentenol to obtain a mixture of 2-methyl-3-butene-2-ol, isopentenol and water. Separating the mixture by using a rectifying tower 4 with about 20 theoretical plates in a stripping section and a rectifying section respectively, controlling the reflux ratio at the tower top to be about 1:1, inputting the mixture mainly containing 2-methyl 3-butene-2-alcohol and water into a fixed bed reactor 2 for reuse, obtaining a crude product of the isopentenol at the tower bottom, feeding the crude product into a refining tower 4 with about 15 theoretical plates in the stripping section and the rectifying section respectively for refining, and removing the weight to obtain an isopentenol finished product with the content of more than 98.5%.
The operation was stabilized under the above conditions, and the reaction conditions and results of the examples are shown in Table 1.
In the examples, the conversion and selectivity are defined as:
table 1.
Claims (6)
1. A method for preparing isopentenol from 2-methyl-3-buten-2 alcohol, which is characterized by comprising the following steps of: preheating a mixture of 2-methyl-3-butene-2-ol and water, and feeding the mixture into a fixed bed reactor filled with an acidic ion exchange resin as a catalyst, wherein the mass ratio of the 2-methyl-3-butene-2-ol to the water in the mixture fed into the fixed bed reactor is as follows: 0.5-10: 1, obtaining a mixture of 2-methyl-3-buten-2-ol, isoamylene alcohol and water through isomerization reaction, separating by using a rectifying tower, obtaining a mixture of reusable 2-methyl-3-buten-2-ol and water at the tower top, obtaining a crude product of isoamylene alcohol at the tower bottom, and refining the crude product of the isoamylene alcohol by using a refining tower to obtain a finished product of the isoamylene alcohol; the acidic ion exchange resin is strong acidic resin, weak acidic resin or a combination of the strong acidic resin and the weak acidic resin; the temperature of the fixed bed reactor is 40-90 ℃, and the pressure is normal pressure.
2. A process for the preparation of prenol from 2-methyl-3-buten-2-ol as claimed in claim 1, wherein: the acidic ion exchange resin is macroporous strong-acid styrene type cation exchange resin, and the mass airspeed in the fixed bed reactor is 0.5-5 h < -1 >.
3. A process for the preparation of prenol from 2-methyl-3-buten-2-ol as claimed in claim 1, wherein: the temperature of the fixed bed reactor is 55-70 ℃.
4. A process for the preparation of prenol from 2-methyl-3-buten-2-ol as claimed in claim 1, wherein: the mass ratio of the 2-methyl-3-buten-2-ol to the water in the mixture fed into the fixed bed reactor is 1-3: 1.
5. the process for preparing prenol from 2-methyl-3-buten-2 ol as claimed in claim 1, wherein: the mixture of the 2-methyl-3-butene-2-ol, the isoamylene alcohol and the water obtained by the isomerization reaction is separated by a rectifying tower with 20 theoretical plates in a stripping section and a rectifying section respectively, the reflux ratio of the tower top is controlled to be 1:1, and the mixture of the 2-methyl-3-butene-2-ol and the water is obtained and is input into a fixed bed reactor for reuse.
6. The process for preparing prenol from 2-methyl-3-buten-2 ol as claimed in claim 1, wherein: and (3) obtaining a crude product of the prenol in the tower kettle, and feeding the crude product into a refining tower with 15 theoretical plates in a stripping section and a rectifying section respectively for refining to obtain a finished product of the prenol with the content of more than 98.5%.
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| CN201710944129.1A CN107840781B (en) | 2017-09-30 | 2017-09-30 | Method for preparing isopentenol from 2-methyl-3-buten-2 alcohol |
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| CN101381283A (en) * | 2008-10-30 | 2009-03-11 | 浙江新和成股份有限公司 | Method for continuously preparing 3-methyl-2-butenol |
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| CN103360215A (en) * | 2013-06-27 | 2013-10-23 | 山东新和成药业有限公司 | Method for synthesizing isopentenol from 3-methyl-3-butene-1-ol through catalytic transposition in water-organic two-phase system |
| CN105967978A (en) * | 2016-07-15 | 2016-09-28 | 西南化工研究设计院有限公司 | Isomerization synthesis of 3-methyl-2-buten-1-ol using water-containing methyl butenol |
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