CN102311317B - Method for preparing cyclopentanol through hydration of cyclopentene - Google Patents
Method for preparing cyclopentanol through hydration of cyclopentene Download PDFInfo
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- CN102311317B CN102311317B CN201010221007.8A CN201010221007A CN102311317B CN 102311317 B CN102311317 B CN 102311317B CN 201010221007 A CN201010221007 A CN 201010221007A CN 102311317 B CN102311317 B CN 102311317B
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- reaction
- cyclopentenes
- cyclopentene
- hydration
- water
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- 238000000034 method Methods 0.000 title claims abstract description 39
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000006703 hydration reaction Methods 0.000 title claims abstract description 24
- 230000036571 hydration Effects 0.000 title claims abstract description 15
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title claims abstract description 14
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 title abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 15
- 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 10
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001941 cyclopentenes Chemical class 0.000 claims description 39
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 abstract description 6
- 229910052799 carbon Inorganic materials 0.000 abstract description 5
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract description 2
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 12
- 230000008569 process Effects 0.000 description 11
- 230000009466 transformation Effects 0.000 description 7
- 229920005989 resin Polymers 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 230000000887 hydrating effect Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- -1 carbonium ion Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NDTCXABJQNJPCF-UHFFFAOYSA-N chlorocyclopentane Chemical compound ClC1CCCC1 NDTCXABJQNJPCF-UHFFFAOYSA-N 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000005120 petroleum cracking Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing cyclopentanol through hydration of cyclopentene. The method comprises a step of continuously performing hydration reaction on the cyclopentene and water through a fixed-bed reactor which holds a strongly acidic cation exchange resin catalyst, wherein the liquid hourly space velocity of the cyclopentene is 0.5h <-1> to 20h <-1>; the molar ratio of the cyclopentene to the water is 0.5-10:1; a reaction solvent is C1-C4 low-carbon alcohol; the amount of the added reaction solvent is 0.05-10 percent of the amount of the cyclopentene; the reaction temperature is 100-200 DEG C; and the reaction pressure is 1.0-6.0MPa. Compared with the prior art, the method has the advantages of single material in a reaction system, high conversion efficiency, high selectivity, fewer byproducts, high convenience in product separation, low energy consumption and the like.
Description
Technical field
The invention discloses a kind of method of Preparation of Cyclopantanol by Hydration of Cyclopentene, particularly under storng-acid cation exchange resin exists, by the method for Preparation of Cyclopantanol by Hydration of Cyclopentene.
Background technology
Cyclopentanol is a kind of important fine chemical product intermediate, mainly for the preparation of bromocyclopentane, chlorocyclopentane etc., and can be used for manufacturing the medicines such as antibiotic, antianaphylaxis.Cyclopentanol can make cyclopentanone through the high temperature depickling by hexanodioic acid, then by obtaining after hydrogenation reaction, but owing to producing a large amount of pollutents and the restriction that is subject to raw material sources, this preparation method is eliminated gradually.In addition, with the C of petroleum cracking ethylene by-product processed
5in cut, through separating the cyclopentenes obtained, be raw material, through hydration reaction, also can produce cyclopentanol.Hydration process mainly contains two kinds of techniques, the one, indirect hydrating process, the 2nd, direct hydration technique.Although hydrating process has the advantage that transformation efficiency is high, selectivity is good indirectly, owing to using sulfuric acid in technological process, high to the equipment material requirement, waste is difficult to process, and environmental pollution is comparatively serious.And there are not the problems referred to above in indirect hydration in direct hydration technique, be therefore eco-friendly technological line, the documents and materials of report all adopt this operational path in recent years.As proposing to adopt storng-acid cation exchange resin, Japanese Patent JP2003212803 carries out the method for Preparation of Cyclopantanol by Hydration of Cyclopentene, this patent is under the condition of the molar ratio 1.2～3.0 of cyclopentenes and water, the cyclopentenes per pass conversion is 3.50% left and right, selectivity 98% left and right.The weak point of the method is that reaction conversion ratio is relatively low, and raw material cyclopentenes internal circulating load is large.Chinese patent CN1676504A has proposed a kind of method by Preparation of Cyclopantanol by Hydration of Cyclopentene, the method is to take the fixed-bed reactor that material that cyclopentenes, water, solvent phenol and promotor trialkylamine formed is Primary Catalysts by storng-acid cation exchange resin continuously, carry out hydration reaction, volume space velocity is 2～15h
-1, the mol ratio 0.8～5.0 of cyclopentenes and water, in raw material, cocatalyst concentration is 0.01%～0.2%, 130 ℃～180 ℃ of temperature of reaction, reaction pressure 1.0MPa～3.0MPa, under these conditions, the transformation efficiency of cyclopentenes is 27% left and right, selectivity 99% left and right of cyclopentanol.Although the method has improved the transformation efficiency of cyclopentenes, added C in reactive system
2～C
5trialkylamine, due to trialkylamine be alkalescence, neutralized the sulfonic acid group in the storng-acid cation exchange resin, make the activity decreased of storng-acid cation exchange resin.Also added a large amount of phenol (weight ratio of phenol and cyclopentenes is 0.5～1) in system, made non-reaction soln occupy larger proportion in reaction system, it is complicated that technological process becomes, and follow-up separating difficulty strengthens, and energy consumption is relatively high.
Summary of the invention
For the deficiencies in the prior art, the invention provides a kind of method of Preparation of Cyclopantanol by Hydration of Cyclopentene.The inventive method, under the selective conditions of the transformation efficiency that keeps higher cyclopentenes and cyclopentanol, makes subsequent product separate and is more prone to, and energy consumption is lower.
The method of Preparation of Cyclopantanol by Hydration of Cyclopentene of the present invention comprises: cyclopentenes, reaction solvent and water carry out hydration reaction by the reactor that strong acid cation exchange resin catalyst is housed, and during the liquid of cyclopentenes, volume space velocity is 0.5h
-1～20h
-1, the mol ratio of water and cyclopentenes is 0.5: 1～10: 1,100 ℃～200 ℃ of temperature of reaction, and reaction pressure is 1.0MPa～6.0MPa, reaction solvent is C
1～C
4one or more of alcohol, the reaction solvent add-on is 0.05%～10% of cyclopentenes quality.
In above-mentioned reaction process, reaction conditions is preferably: during the liquid of cyclopentenes, volume space velocity is preferably 0.5h
-1～15h
-1; The mol ratio of water and cyclopentenes is preferably 1: 1～and 8: 1, the reaction solvent add-on is preferably 0.5%～5% of cyclopentenes quality, and temperature of reaction is preferably 100 ℃～150 ℃, and reaction pressure is preferably 2.0MPa～5.0MPa.And the reaction conditions that override is selected is: volume space velocity 1.0h during the liquid of cyclopentenes
-1～5.0h
-1; The mol ratio of water and cyclopentenes is 2: 1～5: 1, and the reaction solvent add-on is 1.0%～3.0% of cyclopentenes quality, 120 ℃～150 ℃ of temperature of reaction, reaction pressure 2.0MPa～3.0MPa.And catalyzer is preferably storng-acid cation exchange resin, can use commercial goods, also can be by existing method preparation, the DNW-II type high-temperature cation-exchange resin catalyzer of specifically producing as Dandong Mingzhu Special Type Resin Co., Ltd..Reaction solvent is preferentially selected C
3or C
4one or more of alcohol, add-on is 1%～3% of cyclopentenes quality.
Compared with prior art, the present invention has added C in reactive system
1～C
4low-carbon alcohol, under the hydration reaction condition, existence due to a small amount of low-carbon alcohol, improved the mutual solubility of cyclopentenes and water, make catalyst surface seldom form the water molecules liquid film or make the moisture thinning of liquid film formed, thereby having reduced the resistance of cyclopentenes to the catalyst surface diffusion, having increased the formation of carbonium ion, improve the speed of hydration reaction, thereby improved the speed of response of cyclopentenes.The substance classes that the inventive method is used is few, and low-carbon alcohol consumption in reaction system seldom, and is easy to separate, and the sepn process energy consumption is low.
Embodiment
Below by specific embodiment, the present invention will be further described.Cyclopentenes transformation efficiency and cyclopentanol selectivity in embodiment and comparative example are calculated by following formula.
Embodiment 1～32
Hydration reaction is to carry out in the stainless steel reactor of Φ 18mm * 1200mm, the DNW-II type heatproof resin catalyst that 30ml Dandong Mingzhu Special Type Resin Co., Ltd. produces of packing in reactor, reactor head and bottom, be respectively charged into the quartz sand that diameter is Φ 0.5mm～1.2mm, after reactor installs, with nitrogen replacement three times, and tightness test is qualified, by cyclopentenes, water and C
1～C
4low-carbon alcohol send into preheater with volume pump according to the ratio of defined, material is preheating to 100 ℃～200 ℃.Material after preheating enters hydration reactor and carries out hydration reaction, and controlling temperature of reaction is 100 ℃～200 ℃, and reaction pressure is 1.0MPa～6.0MPa.For the contrast reaction effect, each embodiment and comparative example all carry out under 130 ℃ and 2MPa.Unreacted cyclopentenes recycles.
Comparative example 1～2
According to the method for embodiment 1, add promotor three alkanamines and reaction solvent phenol in charging.
Comparative example 3～4
According to the method for embodiment 1, do not add any promotor and solvent in charging.
Above used DNW-II type heatproof resin catalyst physico-chemical property is in Table 1, and the reaction conditions of each embodiment and comparative example is in Table 2, and reaction result is in Table 3.
Table 1 has been listed test DNW-II type heatproof resin catalyst character used
| Sequence number | Physical property | Index |
| 1 | Rate of small round spheres/% after mill | 94.0 |
| 2 | Exchange capacity/molL -1 | 0.99 |
| 3 | Water content/quality % | 59.94 |
| 4 | Wet volume density/gmL -1 | 0.81 |
| 5 | Wet true density/gmL -1 | 1.182 |
The reaction conditions of each embodiment of table 2 and comparative example
The reaction result of each embodiment of table 3 and comparative example
| Project | The cyclopentenes per pass conversion, % | The cyclopentanol selectivity, % |
| Embodiment 1 | 12.5 | 98.6 |
| Embodiment 2 | 14.0 | 98.2 |
| Embodiment 3 | 11.4 | 99.1 |
| Embodiment 4 | 15.6 | 98.2 |
| Embodiment 5 | 14.8 | 98.4 |
| Embodiment 6 | 14.5 | 99.3 |
| Embodiment 7 | 12.6 | 98.1 |
| Embodiment 8 | 27.5 | 99.6 |
| Embodiment 9 | 25.6 | 96.8 |
| Embodiment 10 | 29.7 | 95.2 |
| Embodiment 11 | 24.7 | 99.2 |
| Embodiment 12 | 28.9 | 98.5 |
| Embodiment 13 | 24.5 | 97.6 |
| Embodiment 14 | 18.6 | 95.6 |
| Embodiment 15 | 20.1 | 96.4 |
| Embodiment 16 | 18.6 | 98.6 |
| Embodiment 17 | 17.5 | 97.5 |
| Embodiment 18 | 18.6 | 98.4 |
| Embodiment 18 | 16.7 | 99.3 |
| Embodiment 20 | 27.2 | 98.2 |
| Embodiment 21 | 14.3 | 98.6 |
| Embodiment 22 | 15.7 | 97.5 |
| Embodiment 23 | 13.2 | 98.2 |
| Comparative example 1 | 27.2 | 99.1 |
| Comparative example 2 | 27.5 | 98.9 |
| Comparative example 3 | 2.3 | 98.3 |
| Comparative example 4 | 3.5 | 98.0 |
From above embodiment and comparative example data, can find out, the inventive method is compared with the hydrating process that does not make used additives, and transformation efficiency obviously improves.The inventive method and a large amount of solvents of existing use make the hydrating process of used additives compare simultaneously, and transformation efficiency and selectivity under the typical process condition are suitable, but the quantity of solvent of using obviously reduces, do not need to use promotor yet, make the sepn process of reaction product simplify, Energy Intensity Reduction.
Claims (4)
1. the method for a Preparation of Cyclopantanol by Hydration of Cyclopentene, comprising: cyclopentenes, reaction solvent and water carry out hydration reaction by the reactor that strong acid cation exchange resin catalyst is housed, and during the liquid of cyclopentenes, volume space velocity is 0.5h
-1～20h
-1, the mol ratio of water and cyclopentenes is 0.5: 1～10: 1,100 ℃～200 ℃ of temperature of reaction, and reaction pressure is 1.0MPa～6.0MPa, it is characterized in that: reaction solvent is C
3～C
4one or more of alcohol, the reaction solvent add-on is 0.05%～5% of cyclopentenes quality.
2. in accordance with the method for claim 1, it is characterized in that reaction conditions is: during the liquid of cyclopentenes, volume space velocity is 0.5h
-1～15h
-1, the mol ratio of water and cyclopentenes is 1: 1～8: 1, and the reaction solvent add-on is 0.5%～5% of cyclopentenes quality, and temperature of reaction is 100 ℃～150 ℃, and reaction pressure is 2.0MPa～5.0MPa.
3. in accordance with the method for claim 1, it is characterized in that reaction conditions is: during the liquid of cyclopentenes, volume space velocity is 1.0h
-1～5.0h
-1, the mol ratio of water and cyclopentenes is 2: 1～5: 1, the reaction solvent add-on is 1.0%～3.0% of cyclopentenes quality, 120 ℃～150 ℃ of temperature of reaction, reaction pressure 2.0MPa～3.0MPa.
4. it is characterized in that in accordance with the method for claim 1: the reaction solvent add-on is 1%～3% of cyclopentenes quality.
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|---|---|---|---|
| CN201010221007.8A CN102311317B (en) | 2010-07-07 | 2010-07-07 | Method for preparing cyclopentanol through hydration of cyclopentene |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010221007.8A CN102311317B (en) | 2010-07-07 | 2010-07-07 | Method for preparing cyclopentanol through hydration of cyclopentene |
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| CN102311317B true CN102311317B (en) | 2014-01-01 |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102603486A (en) * | 2012-02-26 | 2012-07-25 | 上海派尔科化工材料有限公司 | Method for preparing cyclopentanol from cyclopentene |
| CN103785330B (en) * | 2012-11-01 | 2016-01-20 | 中国石油化工股份有限公司 | A kind of application of olefin hydration reactor |
| CN105585468B (en) * | 2014-10-22 | 2019-02-15 | 中国石油化工股份有限公司 | A method of cyclopentanone is prepared by raw material of cyclopentene |
| CN105523893A (en) * | 2014-10-22 | 2016-04-27 | 中国石油化工股份有限公司 | Method for preparing cyclopentanol |
| CN105585451B (en) * | 2014-10-22 | 2019-07-16 | 中国石油化工股份有限公司 | A kind of method that cyclopentene direct hydration prepares cyclopentanol |
| CN110683935A (en) * | 2019-11-06 | 2020-01-14 | 中国天辰工程有限公司 | Preparation method of cyclododecanol |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1233609A (en) * | 1998-04-24 | 1999-11-03 | 中国石油化工总公司 | Method for preparing tertiary amyl alcohol |
| CN1676505A (en) * | 2004-04-02 | 2005-10-05 | 中国石化上海石油化工股份有限公司 | Method for preparing cyclopentanol by hydration of cyclopentene |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60115542A (en) * | 1983-11-25 | 1985-06-22 | Nippon Zeon Co Ltd | Production of cycloalkanol |
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2010
- 2010-07-07 CN CN201010221007.8A patent/CN102311317B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1233609A (en) * | 1998-04-24 | 1999-11-03 | 中国石油化工总公司 | Method for preparing tertiary amyl alcohol |
| CN1676505A (en) * | 2004-04-02 | 2005-10-05 | 中国石化上海石油化工股份有限公司 | Method for preparing cyclopentanol by hydration of cyclopentene |
Non-Patent Citations (1)
| Title |
|---|
| JP昭60-115542A 1985.06.22 |
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