CN103483135B - 一种高纯度乙叉降冰片烯的制备方法 - Google Patents
一种高纯度乙叉降冰片烯的制备方法 Download PDFInfo
- Publication number
- CN103483135B CN103483135B CN201310393790.XA CN201310393790A CN103483135B CN 103483135 B CN103483135 B CN 103483135B CN 201310393790 A CN201310393790 A CN 201310393790A CN 103483135 B CN103483135 B CN 103483135B
- Authority
- CN
- China
- Prior art keywords
- tower
- tower top
- obtains
- service temperature
- enb
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 title claims abstract description 122
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 67
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000002904 solvent Substances 0.000 claims abstract description 31
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 19
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 72
- 238000010992 reflux Methods 0.000 claims description 58
- 238000006116 polymerization reaction Methods 0.000 claims description 44
- 239000000463 material Substances 0.000 claims description 39
- 239000000470 constituent Substances 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 21
- 238000005336 cracking Methods 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 18
- 229920005989 resin Polymers 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 238000001035 drying Methods 0.000 claims description 14
- 239000002808 molecular sieve Substances 0.000 claims description 14
- 239000003208 petroleum Substances 0.000 claims description 14
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 14
- 238000000605 extraction Methods 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 13
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000007710 freezing Methods 0.000 claims description 12
- 230000008014 freezing Effects 0.000 claims description 12
- 239000002994 raw material Substances 0.000 claims description 10
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- -1 naphthyl alcohol Chemical compound 0.000 claims description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
- UFERIGCCDYCZLN-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-1h-indene Chemical compound C1C=CCC2CC=CC21 UFERIGCCDYCZLN-UHFFFAOYSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 238000009413 insulation Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 2
- UHZLTTPUIQXNPO-UHFFFAOYSA-N 2,6-ditert-butyl-3-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1C(C)(C)C UHZLTTPUIQXNPO-UHFFFAOYSA-N 0.000 claims description 2
- PBBJQDKWYWWATI-UHFFFAOYSA-N cyclohexene ethene Chemical compound C1=CCCCC1.C=C PBBJQDKWYWWATI-UHFFFAOYSA-N 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 230000008901 benefit Effects 0.000 abstract description 7
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 3
- 238000007670 refining Methods 0.000 abstract description 3
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 25
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 12
- 238000005755 formation reaction Methods 0.000 description 10
- 238000004817 gas chromatography Methods 0.000 description 10
- 238000011068 loading method Methods 0.000 description 10
- 238000010606 normalization Methods 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 7
- 238000006471 dimerization reaction Methods 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 4
- OHBTULDTCSOWOY-UHFFFAOYSA-N [C].C=C Chemical compound [C].C=C OHBTULDTCSOWOY-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- QVYYOKWPCQYKEY-UHFFFAOYSA-N [Fe].[Co] Chemical compound [Fe].[Co] QVYYOKWPCQYKEY-UHFFFAOYSA-N 0.000 description 2
- 238000004737 colorimetric analysis Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000004886 process control Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000001020 rhythmical effect Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical class C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- RCQKOGBSRYPVJF-UHFFFAOYSA-N 4-ethenylbicyclo[2.2.1]hept-1-ene Chemical group C1CC2=CCC1(C=C)C2 RCQKOGBSRYPVJF-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000012691 depolymerization reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
项目 | 单位 | 指标 |
纯度 | wt% | 99.42 |
水 | wt%ppm | 50 |
未端乙烯基类化合物 | wt% | 0.12 |
Vinyl norbornene(VNB) | wt% | 0.13 |
轻组分C8/C9 | wt% | 0.08 |
重组分 | wt% | 0.15 |
色度(APHA) | wt ppm | 100 |
外观 | 无颗粒或悬浮颗粒 |
名称 | CPD收率(%) | CPD转换率(%) | VNB选择率(%) | VNB收率(%) |
实施例1 | 95.12 | 92.53 | 66.01 | 61.08 |
实施例2 | 94.83 | 91.91 | 65.32 | 60.04 |
实施例3 | 95.14 | 92.28 | 66.32 | 61.20 |
实施例4 | 95.35 | 91.21 | 65.85 | 60.06 |
实施例5 | 95.54 | 92.31 | 66.45 | 61.34 |
实施例6 | 95.49 | 91.36 | 66.12 | 60.41 |
实施例7 | 95.12 | 92.13 | 66.41 | 61.18 |
实施例8 | 95.31 | 91.24 | 65.82 | 60.05 |
实施例9 | 95.22 | 91.58 | 65.95 | 60.40 |
实施例10 | 95.35 | 91.42 | 65.92 | 60.26 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310393790.XA CN103483135B (zh) | 2013-09-02 | 2013-09-02 | 一种高纯度乙叉降冰片烯的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310393790.XA CN103483135B (zh) | 2013-09-02 | 2013-09-02 | 一种高纯度乙叉降冰片烯的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103483135A CN103483135A (zh) | 2014-01-01 |
CN103483135B true CN103483135B (zh) | 2015-05-06 |
Family
ID=49823798
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201310393790.XA Active CN103483135B (zh) | 2013-09-02 | 2013-09-02 | 一种高纯度乙叉降冰片烯的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN103483135B (zh) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104098422A (zh) * | 2014-07-25 | 2014-10-15 | 中石化上海工程有限公司 | 5-乙烯基-2-降冰片烯异构化生产5-亚乙基-2-降冰片烯的方法 |
CN104098423B (zh) * | 2014-07-25 | 2016-08-17 | 中石化上海工程有限公司 | 5-亚乙基-2-降冰片烯enb的生产方法 |
CN105585413B (zh) * | 2014-10-20 | 2019-08-13 | 中国石油化工股份有限公司 | 一种乙烯基降冰片烯的合成方法 |
CN105585397B (zh) * | 2014-10-20 | 2019-07-16 | 中国石油化工股份有限公司 | 一种通过多侧线进料管式反应器合成乙烯基降冰片烯的方法 |
CN104692994B (zh) * | 2015-02-13 | 2017-01-04 | 浙江大学 | 通过微通道反应器合成乙叉降冰片烯的方法 |
CN105254808A (zh) * | 2015-09-30 | 2016-01-20 | 宁波职业技术学院 | 一种改性石油树脂的制备方法 |
CN105175634A (zh) * | 2015-09-30 | 2015-12-23 | 宁波职业技术学院 | 一种改性碳五石油树脂的制备方法 |
CN105461505B (zh) * | 2015-12-07 | 2017-12-19 | 上海派尔科化工材料股份有限公司 | 一种乙叉降冰片烯的生产方法 |
CN107325228A (zh) * | 2017-08-03 | 2017-11-07 | 恒河材料科技股份有限公司 | 一种四氢茚改性碳九石油树脂的制备方法 |
CN118255644A (zh) * | 2022-12-26 | 2024-06-28 | 中国石油天然气股份有限公司 | 降冰片烯的生产工艺 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4939255B2 (zh) * | 1971-08-07 | 1974-10-24 | ||
FI102473B1 (fi) * | 1996-03-13 | 1998-12-15 | Optatech Oy | Menetelmä norborneenin ja substituoitujen norborneenijohdannaisten valmistamiseksi |
JP2002284716A (ja) * | 2001-03-28 | 2002-10-03 | Sumitomo Chem Co Ltd | 精ジシクロペンタジエン及び5−エチリデン−2−ノルボルネンの製造方法 |
CN102010285B (zh) * | 2010-11-02 | 2013-10-02 | 宁波职业技术学院 | 一种从乙烯裂解碳九重馏分提取甲基环戊二烯方法 |
CN102516010B (zh) * | 2011-11-25 | 2013-10-09 | 大庆华科股份有限公司 | 用于分离石油裂解乙烯副产碳五馏分中的双烯烃组分的方法及设备 |
-
2013
- 2013-09-02 CN CN201310393790.XA patent/CN103483135B/zh active Active
Also Published As
Publication number | Publication date |
---|---|
CN103483135A (zh) | 2014-01-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN103483135B (zh) | 一种高纯度乙叉降冰片烯的制备方法 | |
CN102010285B (zh) | 一种从乙烯裂解碳九重馏分提取甲基环戊二烯方法 | |
CN102304009B (zh) | Mtp反应混合气分离方法及系统 | |
CN105399590A (zh) | 一种碳九原料经气-液相解聚制备双环戊二烯的方法 | |
CN202081036U (zh) | Mtp反应混合气分离系统 | |
CN104177214A (zh) | 一种催化裂化富气和甲醇制烯烃反应产物混合分离方法 | |
CN103172487B (zh) | 一种高纯度异烯烃(叔烯烃)的生产工艺 | |
CN101880346A (zh) | 高含量顺-1,4-聚异戊二烯的合成方法 | |
CN104370678B (zh) | 一种费托合成轻质馏分油中烯烃综合利用方法 | |
CN103193581A (zh) | 一种以dmto副产煤基混合碳四为原料联产1,3-丁二烯和乙基叔丁基醚的装置和方法 | |
CN103664470A (zh) | 一种制备降冰片烯的方法 | |
CN102050690A (zh) | 一种异烯烃生产方法 | |
CN102584518B (zh) | 一种异丁烯的工业化生产方法及生产装置 | |
CN106588557A (zh) | 一种炼厂干气制备乙苯的方法 | |
CN104250204B (zh) | 一种混合醚化工艺 | |
CN103121905B (zh) | 富含炔烃的烃类燃料气的回收方法 | |
CN104672046A (zh) | 一种将碳四烯烃分离后回炼在催化裂化或裂解过程中增产乙烯和丙烯的方法 | |
CN107879884A (zh) | 一种混合碳四生产异丁烷的方法和装置 | |
CN104250192B (zh) | 一种丙烯和丁二烯的制备方法 | |
CN103965007B (zh) | 混合碳四增产丁二烯的方法 | |
CN103058815A (zh) | 一种由焦化粗苯连续提取双环戊二烯的方法 | |
CN104449808B (zh) | 一种降低乙烯装置急冷油黏度的系统及方法 | |
CN102267854A (zh) | 一种硫酸萃取法制备异丁烯的方法 | |
CN109265306A (zh) | 一种碳四加氢的生产装置及碳四加氢方法 | |
CN105541529A (zh) | 一种乙烯基降冰片烯的生产方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C56 | Change in the name or address of the patentee | ||
CP01 | Change in the name or title of a patent holder |
Address after: Tang Lu, Zhenhai District, Town Creek Yuejin 315200 Zhejiang city of Ningbo province No. 3511 Patentee after: HENGHE MATERIALS & SCIENCE TECHNOLOGY Co.,Ltd. Patentee after: Ningbo Polytechnic Address before: Tang Lu, Zhenhai District, Town Creek Yuejin 315200 Zhejiang city of Ningbo province No. 3511 Patentee before: Zhejiang Henghe Petrochemical Co.,Ltd. Patentee before: Ningbo Polytechnic |
|
TR01 | Transfer of patent right |
Effective date of registration: 20211210 Address after: 315200 no.3511, yuejintang Road, Shupu Town, Zhenhai District, Ningbo City, Zhejiang Province Patentee after: HENGHE MATERIALS & SCIENCE TECHNOLOGY Co.,Ltd. Address before: 315200 no.3511, yuejintang Road, Shupu Town, Zhenhai District, Ningbo City, Zhejiang Province Patentee before: HENGHE MATERIALS & SCIENCE TECHNOLOGY Co.,Ltd. Patentee before: Ningbo Polytechnic |
|
TR01 | Transfer of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A kind of preparation method of high-purity ethylidene norbornene Effective date of registration: 20220729 Granted publication date: 20150506 Pledgee: Bank of China Limited by Share Ltd. Zhenhai Branch Pledgor: HENGHE MATERIALS & SCIENCE TECHNOLOGY Co.,Ltd. Registration number: Y2022330001553 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20230713 Granted publication date: 20150506 Pledgee: Bank of China Limited by Share Ltd. Zhenhai Branch Pledgor: HENGHE MATERIALS & SCIENCE TECHNOLOGY Co.,Ltd. Registration number: Y2022330001553 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right |