CN105237355A - 一种环戊烷氧化制备环戊醇和环戊酮的方法 - Google Patents
一种环戊烷氧化制备环戊醇和环戊酮的方法 Download PDFInfo
- Publication number
- CN105237355A CN105237355A CN201510712102.0A CN201510712102A CN105237355A CN 105237355 A CN105237355 A CN 105237355A CN 201510712102 A CN201510712102 A CN 201510712102A CN 105237355 A CN105237355 A CN 105237355A
- Authority
- CN
- China
- Prior art keywords
- cyclopentanol
- cyclopentanone
- pentamethylene
- oxidation
- general formula
- 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.)
- Granted
Links
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 title claims abstract description 194
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title claims abstract description 133
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 119
- 230000003647 oxidation Effects 0.000 title claims abstract description 116
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 title claims abstract description 100
- 238000002360 preparation method Methods 0.000 title abstract description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 title abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 34
- 239000007791 liquid phase Substances 0.000 claims abstract description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
- 239000001301 oxygen Substances 0.000 claims abstract description 25
- 239000007789 gas Substances 0.000 claims abstract description 16
- 238000000926 separation method Methods 0.000 claims abstract description 4
- 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 description 122
- 239000000126 substance Substances 0.000 claims description 29
- 229910052751 metal Inorganic materials 0.000 claims description 26
- 239000002184 metal Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- -1 transition metal salt Chemical class 0.000 claims description 13
- 229910052742 iron Inorganic materials 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 229910052804 chromium Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052748 manganese Inorganic materials 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 235000017166 Bambusa arundinacea Nutrition 0.000 claims description 5
- 235000017491 Bambusa tulda Nutrition 0.000 claims description 5
- 241001330002 Bambuseae Species 0.000 claims description 5
- 235000015334 Phyllostachys viridis Nutrition 0.000 claims description 5
- 239000011425 bamboo Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- MKACMVMZUIQKNY-UHFFFAOYSA-N 2-hydroxy-5-nitroisoindole-1,3-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(=O)C2=C1 MKACMVMZUIQKNY-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 8
- 230000007613 environmental effect Effects 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 1
- 230000014759 maintenance of location Effects 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 230000009466 transformation Effects 0.000 description 34
- 238000004458 analytical method Methods 0.000 description 26
- 238000012423 maintenance Methods 0.000 description 26
- 238000005070 sampling Methods 0.000 description 26
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 13
- 239000011572 manganese Substances 0.000 description 12
- 239000002994 raw material Substances 0.000 description 8
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 238000006703 hydration reaction Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 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 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- SZKXDURZBIICCF-UHFFFAOYSA-N cobalt;pentane-2,4-dione Chemical group [Co].CC(=O)CC(C)=O SZKXDURZBIICCF-UHFFFAOYSA-N 0.000 description 2
- 208000012839 conversion disease Diseases 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HYZQBNDRDQEWAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese(3+) Chemical group [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 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- DPSWNBLFKLUQTP-UHFFFAOYSA-N bismuth vanadium Chemical compound [V].[Bi] DPSWNBLFKLUQTP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001941 cyclopentenes Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
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CN201510712102.0A CN105237355B (zh) | 2015-10-28 | 2015-10-28 | 一种环戊烷氧化制备环戊醇和环戊酮的方法 |
Applications Claiming Priority (1)
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CN201510712102.0A CN105237355B (zh) | 2015-10-28 | 2015-10-28 | 一种环戊烷氧化制备环戊醇和环戊酮的方法 |
Publications (2)
Publication Number | Publication Date |
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CN105237355A true CN105237355A (zh) | 2016-01-13 |
CN105237355B CN105237355B (zh) | 2018-03-27 |
Family
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CN201510712102.0A Active CN105237355B (zh) | 2015-10-28 | 2015-10-28 | 一种环戊烷氧化制备环戊醇和环戊酮的方法 |
Country Status (1)
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CN (1) | CN105237355B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109232209A (zh) * | 2018-10-24 | 2019-01-18 | 浙江大学 | 一种环烷烃类化合物的氧化方法 |
CN109369326A (zh) * | 2018-12-03 | 2019-02-22 | 浙江工业大学 | 一种环戊烷无催化剂氧化新方法 |
CN109608314A (zh) * | 2018-12-03 | 2019-04-12 | 浙江工业大学 | 一种反应条件温和的环戊烷催化氧化新方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5980619A (ja) * | 1982-10-29 | 1984-05-10 | Nippon Zeon Co Ltd | シクロペンテンの酸化方法 |
CN1041937A (zh) * | 1988-10-21 | 1990-05-09 | 斯塔米卡本公司 | 制备环烷酮和/或环烷醇的方法 |
CN101137606A (zh) * | 2005-03-07 | 2008-03-05 | 大赛璐化学工业株式会社 | 有机化合物的氧化方法 |
CN101547881A (zh) * | 2006-12-05 | 2009-09-30 | 大赛璐化学工业株式会社 | 环烷烃氧化产物的制备方法 |
CN102941120A (zh) * | 2012-11-08 | 2013-02-27 | 衢州市科扬化工有限公司 | 一种用于环己烷液相催化氧化制备环己醇和环己酮的催化体系及其使用方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5980619B2 (ja) * | 2012-08-15 | 2016-08-31 | 東芝機械株式会社 | ボーリング用工具およびボーリング用工作機械 |
-
2015
- 2015-10-28 CN CN201510712102.0A patent/CN105237355B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5980619A (ja) * | 1982-10-29 | 1984-05-10 | Nippon Zeon Co Ltd | シクロペンテンの酸化方法 |
CN1041937A (zh) * | 1988-10-21 | 1990-05-09 | 斯塔米卡本公司 | 制备环烷酮和/或环烷醇的方法 |
CN101137606A (zh) * | 2005-03-07 | 2008-03-05 | 大赛璐化学工业株式会社 | 有机化合物的氧化方法 |
CN101547881A (zh) * | 2006-12-05 | 2009-09-30 | 大赛璐化学工业株式会社 | 环烷烃氧化产物的制备方法 |
CN102941120A (zh) * | 2012-11-08 | 2013-02-27 | 衢州市科扬化工有限公司 | 一种用于环己烷液相催化氧化制备环己醇和环己酮的催化体系及其使用方法 |
Non-Patent Citations (1)
Title |
---|
KATARZYNA PAMIN等: "Oxidation of cycloalkanes with molecular oxygen in the presence ofsalen metallocomplexes in thermomorphic conditions", 《CATALYSIS COMMUNICATIONS》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109232209A (zh) * | 2018-10-24 | 2019-01-18 | 浙江大学 | 一种环烷烃类化合物的氧化方法 |
CN109369326A (zh) * | 2018-12-03 | 2019-02-22 | 浙江工业大学 | 一种环戊烷无催化剂氧化新方法 |
CN109608314A (zh) * | 2018-12-03 | 2019-04-12 | 浙江工业大学 | 一种反应条件温和的环戊烷催化氧化新方法 |
Also Published As
Publication number | Publication date |
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CN105237355B (zh) | 2018-03-27 |
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