CN1530358A - 催化氧化环己烷工艺 - Google Patents
催化氧化环己烷工艺 Download PDFInfo
- Publication number
- CN1530358A CN1530358A CNA2003101104584A CN200310110458A CN1530358A CN 1530358 A CN1530358 A CN 1530358A CN A2003101104584 A CNA2003101104584 A CN A2003101104584A CN 200310110458 A CN200310110458 A CN 200310110458A CN 1530358 A CN1530358 A CN 1530358A
- Authority
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- Prior art keywords
- oxidation
- pimelinketone
- hexalin
- cyclohexane
- hexanaphthene
- 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.)
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 81
- 230000003647 oxidation Effects 0.000 title claims abstract description 68
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims abstract description 34
- 230000008569 process Effects 0.000 title claims abstract description 16
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 15
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 65
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 238000005516 engineering process Methods 0.000 claims abstract description 21
- 238000004821 distillation Methods 0.000 claims abstract description 8
- 239000007791 liquid phase Substances 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 13
- 238000006555 catalytic reaction Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 150000007524 organic acids Chemical class 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 10
- FYLJKQFMQFOLSZ-UHFFFAOYSA-N cyclohexylperoxycyclohexane Chemical compound C1CCCCC1OOC1CCCCC1 FYLJKQFMQFOLSZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 150000001868 cobalt Chemical class 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 230000005587 bubbling Effects 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000010907 mechanical stirring Methods 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 238000003809 water extraction Methods 0.000 claims description 5
- 238000005119 centrifugation Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000012065 filter cake Substances 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 22
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 8
- -1 transition metal salt Chemical class 0.000 abstract description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract description 6
- 230000008901 benefit Effects 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 229910052723 transition metal Inorganic materials 0.000 abstract description 4
- 235000011037 adipic acid Nutrition 0.000 abstract description 3
- 239000001361 adipic acid Substances 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000005265 energy consumption Methods 0.000 abstract 1
- CVKFXBUVLBFHGO-UHFFFAOYSA-N cobalt 5,10,15,20-tetraphenyl-21,23-dihydroporphyrin Chemical compound [Co].c1cc2nc1c(-c1ccccc1)c1ccc([nH]1)c(-c1ccccc1)c1ccc(n1)c(-c1ccccc1)c1ccc([nH]1)c2-c1ccccc1 CVKFXBUVLBFHGO-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 8
- 230000009471 action Effects 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- ODVRHJKVXOGKEJ-UHFFFAOYSA-N iron 5,10,15,20-tetraphenyl-21,23-dihydroporphyrin Chemical compound [Fe].c1cc2nc1c(-c1ccccc1)c1ccc([nH]1)c(-c1ccccc1)c1ccc(n1)c(-c1ccccc1)c1ccc([nH]1)c2-c1ccccc1 ODVRHJKVXOGKEJ-UHFFFAOYSA-N 0.000 description 4
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 3
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 239000003426 co-catalyst Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000006213 oxygenation reaction Methods 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 230000009466 transformation Effects 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 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical class [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- LHEFLUZWISWYSQ-CVBJKYQLSA-L cobalt(2+);(z)-octadec-9-enoate Chemical compound [Co+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LHEFLUZWISWYSQ-CVBJKYQLSA-L 0.000 description 1
- AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 230000002498 deadly effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000640 hydroxylating effect Effects 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 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 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Images
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
序号 | 催化剂 | 催化剂浓度ppm | 反应温度℃ | 转化率% | 环己醇和环己酮选择性% |
1 | 四苯基卟啉钴 | 2.5 | 145~148 | 7.2 | 90 |
2 | 四苯基卟啉钴 | 3 | 146~150 | 10 | 88.50 |
3 | 四苯基卟啉铁 | 4 | 146~150 | 9.5 | 90 |
4 | 四苯基卟啉铁 | 3.5 | 146~148 | 8 | 91 |
序号 | 催化剂 | 催化剂浓度ppm | 反应温度℃ | 转化率% | 环己醇和环己酮和过选择性% |
1 | 四苯基卟啉钴 | 2.5 | 145~148 | 7.6 | 90 |
2 | 四苯基卟啉钴 | 3 | 147~151 | 9.8 | 88.60 |
3 | 四苯基卟啉铁 | 4 | 148~151 | 9.3 | 90.2 |
4 | 四苯基卟啉铁 | 3.5 | 148~150 | 7.5 | 91.5 |
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200310110458 CN1247501C (zh) | 2003-01-24 | 2003-10-29 | 催化氧化环已烷工艺 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN03118044.2 | 2003-01-24 | ||
CN03118044 | 2003-01-24 | ||
CN 200310110458 CN1247501C (zh) | 2003-01-24 | 2003-10-29 | 催化氧化环已烷工艺 |
Publications (2)
Publication Number | Publication Date |
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CN1530358A true CN1530358A (zh) | 2004-09-22 |
CN1247501C CN1247501C (zh) | 2006-03-29 |
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CN 200310110458 Expired - Lifetime CN1247501C (zh) | 2003-01-24 | 2003-10-29 | 催化氧化环已烷工艺 |
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CN (1) | CN1247501C (zh) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007134521A1 (fr) * | 2006-05-22 | 2007-11-29 | Hunan University | Appareil et procédé permettant la préparation de décyclohexanol, de cyclohexanone et d'acide adipique par oxydation à l'air de cyclohexane |
CN101838189A (zh) * | 2007-07-06 | 2010-09-22 | 南京理工大学 | 金属次卟啉化合物的制备及其应用方法 |
CN101293810B (zh) * | 2007-04-28 | 2011-11-30 | 中国石油化工股份有限公司 | 一种环己烷的液相氧化方法 |
CN101085714B (zh) * | 2006-06-06 | 2011-12-07 | 中国石油化工集团公司 | 一种环己烷氧化制备环己酮、环己醇的方法 |
CN102343281A (zh) * | 2011-08-05 | 2012-02-08 | 红河学院 | 液相催化氧化环己烷到环己酮的催化剂 |
CN103755521A (zh) * | 2014-01-26 | 2014-04-30 | 沅江华龙催化科技有限公司 | 基于气液固多相反应分离同步反应器利用空气氧化环己烷生产ka油的方法 |
CN104402694A (zh) * | 2014-10-17 | 2015-03-11 | 衢州巨化锦纶有限责任公司 | 一种环己烷液相氧化法制备环己酮的方法 |
CN106831521A (zh) * | 2017-03-07 | 2017-06-13 | 湖北科林博伦新材料有限公司 | 一种甲苯液相空气氧化法制备苄基过氧化物的方法 |
CN107778133A (zh) * | 2016-08-25 | 2018-03-09 | 中国石油化工股份有限公司 | 一种制备环己醇和环己酮的方法 |
CN108503517A (zh) * | 2017-02-28 | 2018-09-07 | 天津市天地创智科技发展有限公司 | 一种绿色节能的环己烷氧化制备环己酮的***及方法 |
CN110590504A (zh) * | 2019-08-30 | 2019-12-20 | 浙江工业大学 | 一种双金属钴(ii)盐/铜(ii)盐协同催化氧化环烷烃制备环烷醇和环烷酮的方法 |
-
2003
- 2003-10-29 CN CN 200310110458 patent/CN1247501C/zh not_active Expired - Lifetime
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007134521A1 (fr) * | 2006-05-22 | 2007-11-29 | Hunan University | Appareil et procédé permettant la préparation de décyclohexanol, de cyclohexanone et d'acide adipique par oxydation à l'air de cyclohexane |
CN100393680C (zh) * | 2006-05-22 | 2008-06-11 | 湖南大学 | 环己烷空气氧化制备环己醇、环己酮和己二酸的工艺及设备 |
CN101085714B (zh) * | 2006-06-06 | 2011-12-07 | 中国石油化工集团公司 | 一种环己烷氧化制备环己酮、环己醇的方法 |
CN101293810B (zh) * | 2007-04-28 | 2011-11-30 | 中国石油化工股份有限公司 | 一种环己烷的液相氧化方法 |
CN101838189A (zh) * | 2007-07-06 | 2010-09-22 | 南京理工大学 | 金属次卟啉化合物的制备及其应用方法 |
CN102343281A (zh) * | 2011-08-05 | 2012-02-08 | 红河学院 | 液相催化氧化环己烷到环己酮的催化剂 |
CN103755521A (zh) * | 2014-01-26 | 2014-04-30 | 沅江华龙催化科技有限公司 | 基于气液固多相反应分离同步反应器利用空气氧化环己烷生产ka油的方法 |
CN103755521B (zh) * | 2014-01-26 | 2015-02-18 | 沅江华龙催化科技有限公司 | 基于气液固多相反应分离同步反应器利用空气氧化环己烷生产ka油的方法 |
CN104402694A (zh) * | 2014-10-17 | 2015-03-11 | 衢州巨化锦纶有限责任公司 | 一种环己烷液相氧化法制备环己酮的方法 |
CN104402694B (zh) * | 2014-10-17 | 2015-11-25 | 衢州巨化锦纶有限责任公司 | 一种环己烷液相氧化法制备环己酮的方法 |
CN107778133A (zh) * | 2016-08-25 | 2018-03-09 | 中国石油化工股份有限公司 | 一种制备环己醇和环己酮的方法 |
CN108503517A (zh) * | 2017-02-28 | 2018-09-07 | 天津市天地创智科技发展有限公司 | 一种绿色节能的环己烷氧化制备环己酮的***及方法 |
CN106831521A (zh) * | 2017-03-07 | 2017-06-13 | 湖北科林博伦新材料有限公司 | 一种甲苯液相空气氧化法制备苄基过氧化物的方法 |
CN106831521B (zh) * | 2017-03-07 | 2018-08-21 | 湖北科林博伦新材料有限公司 | 一种甲苯液相空气氧化法制备苄基过氧化物的方法 |
CN110590504A (zh) * | 2019-08-30 | 2019-12-20 | 浙江工业大学 | 一种双金属钴(ii)盐/铜(ii)盐协同催化氧化环烷烃制备环烷醇和环烷酮的方法 |
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