CN100393676C - Method for producing high-purity cyclopentadiene and cyclopentane by coarse piperyene - Google Patents
Method for producing high-purity cyclopentadiene and cyclopentane by coarse piperyene Download PDFInfo
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- CN100393676C CN100393676C CNB2005101311615A CN200510131161A CN100393676C CN 100393676 C CN100393676 C CN 100393676C CN B2005101311615 A CNB2005101311615 A CN B2005101311615A CN 200510131161 A CN200510131161 A CN 200510131161A CN 100393676 C CN100393676 C CN 100393676C
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- pentamethylene
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- pentadiene
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title claims abstract description 63
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 11
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title description 8
- 238000000605 extraction Methods 0.000 claims abstract description 39
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims abstract description 37
- 239000000463 material Substances 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 18
- 241000282326 Felis catus Species 0.000 claims description 28
- 150000001941 cyclopentenes Chemical class 0.000 claims description 26
- 238000010992 reflux Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 15
- 239000002994 raw material Substances 0.000 claims description 8
- 238000011084 recovery Methods 0.000 claims description 5
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 abstract description 24
- 239000000047 product Substances 0.000 abstract description 20
- 239000003795 chemical substances by application Substances 0.000 abstract description 17
- 238000000926 separation method Methods 0.000 abstract description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 4
- 239000005977 Ethylene Substances 0.000 abstract description 3
- 238000005120 petroleum cracking Methods 0.000 abstract description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 abstract 3
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 abstract 3
- 238000000895 extractive distillation Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical group CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- SRABLLAQEZEQOK-UHFFFAOYSA-N C=CC(C)=C.C(=O)N(C)C Chemical compound C=CC(C)=C.C(=O)N(C)C SRABLLAQEZEQOK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- KUZSQUMLOPXIHS-UHFFFAOYSA-N cyclopenta-1,3-diene Chemical compound C1C=CC=C1.C1C=CC=C1.C1C=CC=C1 KUZSQUMLOPXIHS-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- -1 isoprene containing Chemical class 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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Abstract
The present invention discloses a method for preparing high-purity cyclopentene and high-purity pentamethylene by using coarse 1, 3-pentadiene got from the separation of ethylene by-product C5 prepared by petroleum cracking, which comprises the following steps: feeding the coarse 1, 3-pentadiene into an extraction tower under the existence of a polymerization inhibitor, getting the mixing material of cyclopentene and pentamethylene from the top of the extraction tower, and an extraction agent and the 1, 3-pentadiene being in a tower still; feeding the mixing material got from the top of the extraction tower into a first rectifying tower, eliminating a light component at the top of the first rectifying tower, and getting the mixing material of the cyclopentene and the pentamethylene in the tower still; feeding the mixing material got from the first rectifying tower into a second rectifying tower, getting a cyclopentene product above 99% at the top of the second rectifying tower, and getting a pentamethylene mixing material in the tower still; feeding the mixing material got from the second rectifying tower into a third rectifying tower, eliminating a heavy component in the tower still, and getting a pentamethylene product at the top of the third rectifying tower. The method uses an extractive distillation method, and has the advantages of high extraction accuracy, stable product quality and easy industrial production.
Description
(1) technical field under
The present invention relates to the method for a kind of production separation of high-purity Cyclopentene, pentamethylene, particularly a kind of petroleum cracking system ethylene by-product product carbon five that utilizes separates the coarse piperyene production separation of high-purity Cyclopentene that obtains, the method for pentamethylene.
(2) background technology
In the petroleum cracking process of producing ethylene, byproduct carbon five accounts for 12%-14%, and China's ethene working ability in 2005 reaches 7,500,000 tons, produces more than 100 ten thousand tons of carbon five byproducts.Because diolefins such as isoprene containing, cyclopentadiene, m-pentadiene in the C5 fraction, these diolefin chemical are active, are important chemical material very.External and domestic to these three kinds of diolefins development and use early, particularly isoprene, cyclopentadiene (dicyclopentadiene) are widely used, because m-pentadiene purity is usually about 65%, and contain 15%-17% cyclopentenes, 7%-9% pentamethylene component (3% right and left rings amylene, 1% right and left rings pentane all concentrate in the coarse piperyene in the material of carbon Wuyuan), usually can only be used for making m-pentadiene petro-resin, comprehensive utilization value is single.Along with the particularly development of Speciality Petrochemicals of petrochemical complex, also be that important industrial chemicals cyclopentenes, pentamethylene adopt dicyclopentadiene cracking back end hydrogenation to produce usually.Because cyclopentenes, m-pentadiene boiling point are identical, the conventional rectification method can't realize cyclopentenes, m-pentadiene are separated.
(3) summary of the invention
The present invention provides a kind of method of utilizing coarse piperyene production separation of high-purity Cyclopentene, pentamethylene that is easy to suitability for industrialized production, constant product quality in order to remedy the deficiencies in the prior art.
The present invention is achieved through the following technical solutions:
A kind of method of utilizing coarse piperyene production separation of high-purity Cyclopentene, pentamethylene, its special character is: comprise the steps:
(1) the coarse piperyene raw material enters extraction tower in the presence of stopper, the extraction tower working pressure is: 0.14-0.17Mpa, temperature 52-135 ℃, reflux ratio 2-9, extraction agent and material quantity volume ratio are 4: 1-10: 1, obtain cyclopentenes, pentamethylene mixture from cat head, the tower still is extraction agent and m-pentadiene;
(2) step (1) cat head material is entered first rectifying tower, working pressure: be 0.18-0.25Mpa, temperature 55-75 ℃, reflux ratio 25-30, the light component of removed overhead, tower still obtain cyclopentenes, pentamethylene mixture;
(3) step (2) tower still material is entered second rectifying tower, working pressure: be 0.11-0.2Mpa, temperature 55-70 ℃, reflux ratio 10-15, cat head obtain 99% above cyclopentenes product, and the tower still obtains the pentamethylene mixture;
(4) step (3) tower still material is entered the 3rd rectifying tower, working pressure is: 0.1-0.15Mpa, and temperature 50-70 ℃, reflux ratio 5-10, the tower still removes heavy component, and cat head obtains cyclopentane product.
The method of utilizing coarse piperyene production separation of high-purity Cyclopentene, pentamethylene of the present invention, in step (1): tower still material removes extraction agent through Analytic Tower and obtains the high purity m-pentadiene, and the extraction agent recovery is returned extraction tower and is recycled.
The method of utilizing coarse piperyene production separation of high-purity Cyclopentene, pentamethylene of the present invention, in step (1): extraction agent is in the cat head charging, feeding temperature 70-95 ℃.
The method of utilizing coarse piperyene production separation of high-purity Cyclopentene, pentamethylene of the present invention, in step (1): described extraction agent is a dimethyl formamide; Stopper is SP-731.
One, raw material is formed:
1, raw material of the present invention (volume) composed as follows:
Isoprene: 2.2455%; 2-amylene: 0.4379%; 2-methyl-2-butene: 0.7051%; M-pentadiene: 68.4548%; Cyclopentadiene: 0.3456%; Cyclopentenes: 15.9485%; Pentamethylene: 8.3947%; C
6Heavy constituent: 0.5%.
2, the relative volatility of m-pentadiene component in the presence of solvent:
| Form | Boiling point | Solvent-free | Dimethyl formamide |
| Isoprene | 34.07 | 1 | 1 |
| The 2-amylene | 36.35 | 0.930 | 1.605 |
| The 2-methyl-2-butene | 18.57 | 0.867 | 1.396 |
| Anti--1,3 pentadiene | 42.03 | 0.775 | 0.763 |
| Suitable-1,3 pentadiene | 44.07 | 0.725 | 0.706 |
| Cyclopentadiene | 42.50 | 0.811 | 0.623 |
| Cyclopentenes | 44.24 | 0.719 | 0.914 |
| Pentamethylene | 49.26 | 0.610 | 1.166 |
Two, product is formed (volume):
1. cyclopentenes＞99%
Pentamethylene+C
6Alkene≤0.6%; Other impurity≤0.4%; Moisture content≤300PPm; Colourity (apha)≤25.
2. pentamethylene 〉=98%.
3. smart m-pentadiene: content 〉=95%.The fine chemical product that is used for high additive value, colourless, transparent liquid.
Light component: be used for blended gasoline or do fuel use (colourless transparent liquid);
Heavy component: be used for blended gasoline or do fuel use (colourless transparent liquid).
In sum, the present invention adopts the method for extracting rectifying, from raw material, remove m-pentadiene (purity is more than 95%) through extraction process, in the presence of extraction agent, change the relative volatility of each component of coarse piperyene, reach the segregative effect of m-pentadiene each component, and then obtain satisfactory cyclopentenes, cyclopentane product, have purification precision height, constant product quality, be easy to the advantage of suitability for industrialized production through two tower rectifying.
(4) description of drawings
The present invention is further illustrated below in conjunction with accompanying drawing.
Accompanying drawing is a process flow diagram of the present invention.
(5) embodiment
Embodiment 1:
The coarse piperyene raw material enters extraction tower in the presence of stopper SP-731, the extraction agent dimethyl formamide that adds with cat head contacts, control extraction tower working pressure is: 0.14,52 ℃ of temperature, reflux ratio 2, dimethyl formamide and material quantity volume ratio are 4: 1,70 ℃ of feeding temperatures, obtain cyclopentenes, pentamethylene mixture from cat head, the tower still is extraction agent and m-pentadiene.Materials abstraction agent of tower still and m-pentadiene enter Analytic Tower, the working pressure normal pressure, and tower still temperature is 160 ℃, and tower bottoms returns extraction tower or the recovery system of desolvating, and cat head steams the smart m-pentadiene of high purity.The cat head material is entered first rectifying tower, working pressure: be 0.18pa, 55 ℃ of temperature, reflux ratio 25, the light component of removed overhead, tower still obtain cyclopentenes, pentamethylene mixture; The first rectifying Tata still material is entered second rectifying tower, working pressure: be 0.11Mpa, 55 ℃ of temperature, reflux ratio 10, cat head obtains 99% above cyclopentenes product, and the tower still obtains the pentamethylene mixture; The second rectifying Tata still material is entered the 3rd rectifying tower, and working pressure is: 0.1Mpa, and 50 ℃ of temperature, reflux ratio 5, the tower still removes heavy component, and cat head obtains 98% above cyclopentane product, and tower still heavy component is delivered to the finished product jar.
Embodiment 2:
The coarse piperyene raw material enters extraction tower in the presence of stopper SP-731, the extraction agent dimethyl formamide that adds with cat head contacts, control extraction tower working pressure is: 0.17M pa, 135 ℃ of temperature, reflux ratio 9, dimethyl formamide and material quantity volume ratio are 10: 1,95 ℃ of feeding temperatures, obtain cyclopentenes, pentamethylene mixture from cat head, the tower still is extraction agent and m-pentadiene.Materials abstraction agent of tower still and m-pentadiene enter Analytic Tower, the working pressure normal pressure, and tower still temperature is 100 ℃, and tower bottoms returns extraction tower or the recovery system of desolvating, and cat head steams the smart m-pentadiene of high purity.The cat head material is entered first rectifying tower, working pressure: be 0.25Mpa, 75 ℃ of temperature, reflux ratio 30, the light component of removed overhead, tower still obtain cyclopentenes, pentamethylene mixture; The first rectifying Tata still material is entered second rectifying tower, working pressure: be 0.2Mpa, 70 ℃ of temperature, reflux ratio 15, cat head obtains 99% above cyclopentenes product, and the tower still obtains the pentamethylene mixture; The second rectifying Tata still material is entered the 3rd rectifying tower, and working pressure is: 0.15Mpa, and 70 ℃ of temperature, reflux ratio 10, the tower still removes heavy component, and cat head obtains 98% above cyclopentane product, and tower still heavy component is delivered to the finished product jar.
Embodiment 3:
The coarse piperyene raw material enters extraction tower in the presence of stopper SP-731, the extraction agent dimethyl formamide that adds with cat head contacts, control extraction tower working pressure is: 0.16Mpa, 85 ℃ of temperature, reflux ratio 6, dimethyl formamide and material quantity volume ratio are 7: 1,80 ℃ of feeding temperatures, obtain cyclopentenes, pentamethylene mixture from cat head, the tower still is extraction agent and m-pentadiene.Materials abstraction agent of tower still and m-pentadiene enter Analytic Tower, the working pressure normal pressure, and tower still temperature is 80 ℃, and tower bottoms returns extraction tower or the recovery system of desolvating, and cat head steams the smart m-pentadiene of high purity.The cat head material is entered first rectifying tower, working pressure: be 0.23Mpa, 66 ℃ of temperature, reflux ratio 28, the light component of removed overhead, tower still obtain cyclopentenes, pentamethylene mixture; The first rectifying Tata still material is entered second rectifying tower, working pressure: be 0.15Mpa, 63 ℃ of temperature, reflux ratio 12, cat head obtains 99% above cyclopentenes product, and the tower still obtains the pentamethylene mixture; The second rectifying Tata still material is entered the 3rd rectifying tower, and working pressure is: 0.12Mpa, and 60 ℃ of temperature, reflux ratio 7, the tower still removes heavy component, and cat head obtains 98% above cyclopentane product, and tower still heavy component is delivered to the finished product jar.
Claims (3)
1. method of utilizing coarse piperyene to produce cyclopentenes, pentamethylene is characterized in that:
Comprise the steps:
(1) the coarse piperyene raw material enters extraction tower in the presence of stopper, the extraction tower working pressure is 0.14-0.17Mpa, temperature 52-135 ℃, reflux ratio 2-9, extraction agent and material quantity volume ratio are 4: 1-10: 1, obtain cyclopentenes, pentamethylene mixture from cat head, the tower still is extraction agent and m-pentadiene;
(2) step (1) cat head material is entered first rectifying tower, working pressure is 0.18-0.25Mpa, temperature 55-75 ℃, and reflux ratio 25-30, the light component of removed overhead, tower still obtain cyclopentenes, pentamethylene mixture;
(3) step (2) tower still material is entered second rectifying tower, working pressure is 0.11-0.2Mpa, and temperature 55-70 ℃, reflux ratio 10-15, cat head obtain 99% above cyclopentenes product, and the tower still obtains the pentamethylene mixture;
(4) step (3) tower still material is entered the 3rd rectifying tower, working pressure is 0.1-0.15Mpa, temperature 50-70 ℃, and reflux ratio 5-10, the tower still removes heavy component, and cat head obtains cyclopentane product.
2. the method for utilizing coarse piperyene to produce cyclopentenes, pentamethylene according to claim 1, it is characterized in that: in step (1): tower still material removes extraction agent through Analytic Tower and obtains the high purity m-pentadiene, and the extraction agent recovery is returned extraction tower and recycled.
3. the method for utilizing coarse piperyene to produce cyclopentenes, pentamethylene according to claim 1 is characterized in that: in step (1): extraction agent is in the cat head charging, feeding temperature 70-95 ℃.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005101311615A CN100393676C (en) | 2005-12-26 | 2005-12-26 | Method for producing high-purity cyclopentadiene and cyclopentane by coarse piperyene |
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| CNB2005101311615A CN100393676C (en) | 2005-12-26 | 2005-12-26 | Method for producing high-purity cyclopentadiene and cyclopentane by coarse piperyene |
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Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101544534B (en) * | 2009-04-16 | 2012-04-25 | 中国石油兰州石油化工公司 | Method for directly separating and purifying cyclopentene from C5 raw material adopting extraction and distillation technology |
| CN101671224B (en) * | 2009-10-14 | 2013-05-22 | 山东玉皇化工有限公司 | Preparation method of high purity dicyclopentadiene |
| CN102391063B (en) * | 2011-09-20 | 2013-12-11 | 中国石油天然气集团公司 | Process method and equipment for refining, extracting and distilling cyclopentane |
| CN103304361A (en) * | 2012-03-13 | 2013-09-18 | 上海博润石化科技发展有限公司 | Production method of high purity cyclopentene |
| CN103204759B (en) * | 2013-03-12 | 2015-01-14 | 上海派尔科化工材料有限公司 | Comprehensive pentadiene utilization method |
| CN103342624B (en) * | 2013-07-24 | 2014-12-17 | 上海派尔科化工材料有限公司 | Preparation method of high purity cyclopentene |
| CN105585412B (en) * | 2014-10-22 | 2019-04-12 | 中国石油化工股份有限公司 | A method of preparing polymer grade piperyene |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1232816A (en) * | 1998-03-05 | 1999-10-27 | Ec石油化工股份有限公司 | Process for isolating cyclopentane and/or cyclopentene |
| US6153804A (en) * | 1996-04-04 | 2000-11-28 | Basf Aktiengesellschaft | Production of cyclopentane and/or cyclopentene from partially hydrogenated pyrolysis gasoline |
| CN1445206A (en) * | 2002-03-19 | 2003-10-01 | 中国石化上海石油化工股份有限公司 | Method for purifying and refining piperyene |
-
2005
- 2005-12-26 CN CNB2005101311615A patent/CN100393676C/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6153804A (en) * | 1996-04-04 | 2000-11-28 | Basf Aktiengesellschaft | Production of cyclopentane and/or cyclopentene from partially hydrogenated pyrolysis gasoline |
| CN1232816A (en) * | 1998-03-05 | 1999-10-27 | Ec石油化工股份有限公司 | Process for isolating cyclopentane and/or cyclopentene |
| CN1445206A (en) * | 2002-03-19 | 2003-10-01 | 中国石化上海石油化工股份有限公司 | Method for purifying and refining piperyene |
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Change date: 20150713 Registration number: 2012990000387 Pledgor after: Jade Emperor flourishing age chemical inc, Shandong Pledgor before: Shandong Yuhuang Chemical Co., Ltd. |
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Date of cancellation: 20150721 Granted publication date: 20080611 Pledgee: Prudential Bank Ji'nan branch of Limited by Share Ltd Pledgor: Jade Emperor flourishing age chemical inc, Shandong Registration number: 2012990000387 |
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Denomination of invention: Method for producing high-purity cyclopentadiene and cyclopentane by coarse piperyene Effective date of registration: 20150910 Granted publication date: 20080611 Pledgee: China Minsheng Banking Corp Ji'nan branch Pledgor: Jade Emperor flourishing age chemical inc, Shandong Registration number: 2015370000047 |
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Date of cancellation: 20180704 Granted publication date: 20080611 Pledgee: China Minsheng Banking Corp Ji'nan branch Pledgor: Jade Emperor flourishing age chemical inc, Shandong Registration number: 2015370000047 |