CN109248699B - 环己烷氧化制ka油的方法 - Google Patents
环己烷氧化制ka油的方法 Download PDFInfo
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- CN109248699B CN109248699B CN201710576341.7A CN201710576341A CN109248699B CN 109248699 B CN109248699 B CN 109248699B CN 201710576341 A CN201710576341 A CN 201710576341A CN 109248699 B CN109248699 B CN 109248699B
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- cyclohexane
- phosphorus oxide
- vanadium phosphorus
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 31
- 230000003647 oxidation Effects 0.000 title claims abstract description 18
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 87
- 238000006243 chemical reaction Methods 0.000 claims abstract description 61
- LJYCJDQBTIMDPJ-UHFFFAOYSA-N [P]=O.[V] Chemical compound [P]=O.[V] LJYCJDQBTIMDPJ-UHFFFAOYSA-N 0.000 claims abstract description 47
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims abstract description 34
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000012153 distilled water Substances 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012018 catalyst precursor Substances 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims abstract description 9
- 150000001621 bismuth Chemical class 0.000 claims abstract description 7
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims description 24
- 239000000843 powder Substances 0.000 claims description 22
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 16
- 238000001035 drying Methods 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 15
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 11
- 230000004913 activation Effects 0.000 claims description 10
- 239000012298 atmosphere Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- QYIGOGBGVKONDY-UHFFFAOYSA-N 1-(2-bromo-5-chlorophenyl)-3-methylpyrazole Chemical compound N1=C(C)C=CN1C1=CC(Cl)=CC=C1Br QYIGOGBGVKONDY-UHFFFAOYSA-N 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 claims description 4
- 229910000380 bismuth sulfate Inorganic materials 0.000 claims description 4
- BEQZMQXCOWIHRY-UHFFFAOYSA-H dibismuth;trisulfate Chemical compound [Bi+3].[Bi+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BEQZMQXCOWIHRY-UHFFFAOYSA-H 0.000 claims description 4
- 238000007599 discharging Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 2
- VDQDGCAHVVNVDM-UHFFFAOYSA-K bismuth;triperchlorate Chemical compound [Bi+3].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O VDQDGCAHVVNVDM-UHFFFAOYSA-K 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 claims 1
- LEABNKXSQUTCOW-UHFFFAOYSA-N [O].[P].[V] Chemical compound [O].[P].[V] LEABNKXSQUTCOW-UHFFFAOYSA-N 0.000 abstract description 6
- 230000003213 activating effect Effects 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 5
- 229910052797 bismuth Inorganic materials 0.000 abstract description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 abstract description 2
- 238000012546 transfer Methods 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 101100410779 Homo sapiens PXDN gene Proteins 0.000 description 7
- 102100034601 Peroxidasin homolog Human genes 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000010931 gold Substances 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- PWTGXYFKQRZBEV-UHFFFAOYSA-N cyclohexane;hydrogen peroxide Chemical compound OO.C1CCCCC1 PWTGXYFKQRZBEV-UHFFFAOYSA-N 0.000 description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 229940005657 pyrophosphoric acid Drugs 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 229910020599 Co 3 O 4 Inorganic materials 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- CXDRDJZLSQTUAA-UHFFFAOYSA-K [Si+2]=O.P(=O)([O-])([O-])[O-].[Al+3] Chemical compound [Si+2]=O.P(=O)([O-])([O-])[O-].[Al+3] CXDRDJZLSQTUAA-UHFFFAOYSA-K 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004032 porphyrins Chemical group 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
- B01J27/198—Vanadium
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
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CN201710576341.7A CN109248699B (zh) | 2017-07-14 | 2017-07-14 | 环己烷氧化制ka油的方法 |
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CN201710576341.7A CN109248699B (zh) | 2017-07-14 | 2017-07-14 | 环己烷氧化制ka油的方法 |
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CN109248699A CN109248699A (zh) | 2019-01-22 |
CN109248699B true CN109248699B (zh) | 2022-08-12 |
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CN110801824A (zh) * | 2019-11-13 | 2020-02-18 | 江苏方时远略科技咨询有限公司 | 一种非金属光催化剂及其制备方法 |
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US4898989A (en) * | 1988-10-07 | 1990-02-06 | Sun Refining And Marketing Company | Alkane oxidation process |
WO2000048971A1 (en) * | 1999-02-22 | 2000-08-24 | Symyx Technologies, Inc. | Compositions comprising nickel and their use as catalyst in oxidative dehydrogenation of alkanes |
CN1623971A (zh) * | 2003-12-04 | 2005-06-08 | 中国科学院兰州化学物理研究所 | 环己烷选择氧化制备环己酮的方法 |
CN101157048A (zh) * | 2007-11-20 | 2008-04-09 | 吐哈石油勘探开发指挥部石油天然气化工厂 | 一种具有纳米结构的高性能钒磷氧催化剂及其制备方法 |
CN101773849A (zh) * | 2010-01-14 | 2010-07-14 | 华东理工大学 | 一种用于合成环己醇和环己酮的催化剂及制备方法 |
CN101992103A (zh) * | 2010-09-14 | 2011-03-30 | 浙江大学 | 一种用于环己烷氧化的负载型金催化剂及其制备方法 |
CN102211035A (zh) * | 2010-04-06 | 2011-10-12 | 北京化工大学 | 一种v-zsm-5分子筛的制备方法及其对环己烷氧化制备环己醇和环己酮的催化性能 |
CN104607219A (zh) * | 2013-11-05 | 2015-05-13 | 中国石油化工股份有限公司 | 一种丁烷氧化制顺酐的钒磷氧催化剂及其制备方法 |
CN104981462A (zh) * | 2013-02-08 | 2015-10-14 | 罗地亚经营管理公司 | 通过介观结构的vpo催化剂氧化醇化合物 |
CN105457665A (zh) * | 2014-09-09 | 2016-04-06 | 中国石油化工股份有限公司 | 高比表面积钒磷催化剂的制备方法 |
CN106732702A (zh) * | 2015-11-21 | 2017-05-31 | 中国石油化工股份有限公司 | 一种正丁烷氧化生产顺酐的催化剂级配方法 |
-
2017
- 2017-07-14 CN CN201710576341.7A patent/CN109248699B/zh active Active
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
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US4898989A (en) * | 1988-10-07 | 1990-02-06 | Sun Refining And Marketing Company | Alkane oxidation process |
WO2000048971A1 (en) * | 1999-02-22 | 2000-08-24 | Symyx Technologies, Inc. | Compositions comprising nickel and their use as catalyst in oxidative dehydrogenation of alkanes |
CN1623971A (zh) * | 2003-12-04 | 2005-06-08 | 中国科学院兰州化学物理研究所 | 环己烷选择氧化制备环己酮的方法 |
CN101157048A (zh) * | 2007-11-20 | 2008-04-09 | 吐哈石油勘探开发指挥部石油天然气化工厂 | 一种具有纳米结构的高性能钒磷氧催化剂及其制备方法 |
CN101773849A (zh) * | 2010-01-14 | 2010-07-14 | 华东理工大学 | 一种用于合成环己醇和环己酮的催化剂及制备方法 |
CN102211035A (zh) * | 2010-04-06 | 2011-10-12 | 北京化工大学 | 一种v-zsm-5分子筛的制备方法及其对环己烷氧化制备环己醇和环己酮的催化性能 |
CN101992103A (zh) * | 2010-09-14 | 2011-03-30 | 浙江大学 | 一种用于环己烷氧化的负载型金催化剂及其制备方法 |
CN104981462A (zh) * | 2013-02-08 | 2015-10-14 | 罗地亚经营管理公司 | 通过介观结构的vpo催化剂氧化醇化合物 |
CN104607219A (zh) * | 2013-11-05 | 2015-05-13 | 中国石油化工股份有限公司 | 一种丁烷氧化制顺酐的钒磷氧催化剂及其制备方法 |
CN105457665A (zh) * | 2014-09-09 | 2016-04-06 | 中国石油化工股份有限公司 | 高比表面积钒磷催化剂的制备方法 |
CN106732702A (zh) * | 2015-11-21 | 2017-05-31 | 中国石油化工股份有限公司 | 一种正丁烷氧化生产顺酐的催化剂级配方法 |
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"改性VPO催化剂及其环己烷液相氧化反应性能";仇念海 等;《化工进展》;20100815;第29卷(第8期);摘要、第1.2节、第1.4节 * |
仇念海 等."改性VPO催化剂及其环己烷液相氧化反应性能".《化工进展》.2010,第29卷(第8期),摘要、第1.2节、第1.4节. * |
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