CN103055792B - 一种用于环己烷液相氧化的振荡管式反应器的使用方法 - Google Patents
一种用于环己烷液相氧化的振荡管式反应器的使用方法 Download PDFInfo
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- CN103055792B CN103055792B CN201310031981.1A CN201310031981A CN103055792B CN 103055792 B CN103055792 B CN 103055792B CN 201310031981 A CN201310031981 A CN 201310031981A CN 103055792 B CN103055792 B CN 103055792B
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- cyclohexane
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 239000007791 liquid phase Substances 0.000 title claims abstract description 57
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 48
- 230000003647 oxidation Effects 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 109
- 239000007789 gas Substances 0.000 claims abstract description 71
- 239000000376 reactant Substances 0.000 claims abstract description 37
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000000411 inducer Substances 0.000 claims abstract description 26
- 239000007792 gaseous phase Substances 0.000 claims abstract description 20
- 238000010276 construction Methods 0.000 claims abstract description 17
- 238000013016 damping Methods 0.000 claims abstract description 17
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012071 phase Substances 0.000 claims description 35
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 230000001186 cumulative effect Effects 0.000 claims description 16
- 238000007599 discharging Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 230000001105 regulatory effect Effects 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910001882 dioxygen Inorganic materials 0.000 claims description 6
- 230000000630 rising effect Effects 0.000 claims description 4
- 238000009827 uniform distribution Methods 0.000 claims description 4
- 239000000047 product Substances 0.000 description 39
- -1 acetylacetonate compound Chemical class 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 14
- 238000001816 cooling Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000005587 bubbling Effects 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 230000001590 oxidative effect Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 230000002349 favourable effect Effects 0.000 description 5
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- HYZQBNDRDQEWAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese(3+) Chemical compound [Mn+3].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O HYZQBNDRDQEWAN-LNTINUHCSA-N 0.000 description 2
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 2
- ZUSWZTDSZLAUEK-UHFFFAOYSA-N C1(=CC=CC=C1)[Co](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)[Co](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 ZUSWZTDSZLAUEK-UHFFFAOYSA-N 0.000 description 2
- JKEDNTZBGZGJSV-UHFFFAOYSA-N C12=CC=C(N1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2.C2(=CC=CC=C2)[Cu](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.[Cl] Chemical compound C12=CC=C(N1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2.C2(=CC=CC=C2)[Cu](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2.[Cl] JKEDNTZBGZGJSV-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940011182 cobalt acetate Drugs 0.000 description 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 238000002479 acid--base titration Methods 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103285783B (zh) * | 2013-06-14 | 2015-06-17 | 吴嘉 | 一种填充床振荡流反应器 |
CN106475020B (zh) * | 2016-10-20 | 2019-01-29 | 中国石油化工股份有限公司 | 一种用于异丙苯催化氧化制过氧化氢异丙苯的振荡流反应器及方法 |
CN106512871B (zh) * | 2016-12-16 | 2023-01-20 | 阳煤集团青岛恒源化工有限公司 | 一种管道反应器和利用管道反应器碳化丙二醇粗品的方法 |
CN108014733A (zh) * | 2018-01-23 | 2018-05-11 | 邱洪 | 超声波催化的连续流板式反应器 |
WO2021056272A1 (zh) * | 2019-09-25 | 2021-04-01 | 凯莱英生命科学技术(天津)有限公司 | 连续化气液反应装置及含有其的连续化气液反应*** |
CN112915933A (zh) * | 2021-01-29 | 2021-06-08 | 常州大学 | 一种大通量连续气液非均相反应器 |
CN113145022B (zh) * | 2021-05-26 | 2024-06-25 | 大连鼎燕医药化工有限公司 | 芳胺氟化氢重氮盐的连续化热解氟代工艺与设备 |
Citations (4)
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CN1556078A (zh) * | 2004-01-09 | 2004-12-22 | 北京石油化工学院 | 一种环己烷氧化反应器 |
CN1585672A (zh) * | 2001-10-12 | 2005-02-23 | 罗狄亚聚酰胺中间体公司 | 用于液体和气体的氧化反应的反应器 |
CN1834078A (zh) * | 2005-03-18 | 2006-09-20 | 中国石油化工股份有限公司 | 环己烷液相氧化工艺 |
CN101578136A (zh) * | 2006-10-20 | 2009-11-11 | 约翰森·马瑟公开有限公司 | 催化剂的制备方法 |
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GB0604199D0 (en) * | 2006-03-02 | 2006-04-12 | Nitech Solutions Ltd | Apparatus and method for applying oscillatory motion |
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CN1585672A (zh) * | 2001-10-12 | 2005-02-23 | 罗狄亚聚酰胺中间体公司 | 用于液体和气体的氧化反应的反应器 |
CN1556078A (zh) * | 2004-01-09 | 2004-12-22 | 北京石油化工学院 | 一种环己烷氧化反应器 |
CN1834078A (zh) * | 2005-03-18 | 2006-09-20 | 中国石油化工股份有限公司 | 环己烷液相氧化工艺 |
CN101578136A (zh) * | 2006-10-20 | 2009-11-11 | 约翰森·马瑟公开有限公司 | 催化剂的制备方法 |
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Denomination of invention: A Method of Using an Oscillating Tube Reactor for Liquid Phase Oxidation of Cyclohexane Effective date of registration: 20230627 Granted publication date: 20160420 Pledgee: Industrial Bank Co.,Ltd. Shanghai Hongkou sub branch Pledgor: Shanghai Record Pharmaceuticals Ltd.|SHANGHAI RECORDCHEM TECHNOLOGY CO.,LTD. Registration number: Y2023310000303 |