KR20050044918A - 시클로헥산 산화 방법 - Google Patents
시클로헥산 산화 방법 Download PDFInfo
- Publication number
- KR20050044918A KR20050044918A KR1020057004213A KR20057004213A KR20050044918A KR 20050044918 A KR20050044918 A KR 20050044918A KR 1020057004213 A KR1020057004213 A KR 1020057004213A KR 20057004213 A KR20057004213 A KR 20057004213A KR 20050044918 A KR20050044918 A KR 20050044918A
- Authority
- KR
- South Korea
- Prior art keywords
- cyclohexanol
- residue
- cyclohexanone
- phase
- decomposition
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 230000003647 oxidation Effects 0.000 title claims abstract description 10
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 24
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical group OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 claims abstract description 22
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 239000011651 chromium Substances 0.000 claims description 27
- 229910052804 chromium Inorganic materials 0.000 claims description 18
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 17
- 239000012071 phase Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 239000008151 electrolyte solution Substances 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 238000003421 catalytic decomposition reaction Methods 0.000 claims description 4
- 239000003518 caustics Substances 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 230000000593 degrading effect Effects 0.000 claims description 2
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-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
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- RPBPCPJJHKASGQ-UHFFFAOYSA-K chromium(3+);octanoate Chemical compound [Cr+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O RPBPCPJJHKASGQ-UHFFFAOYSA-K 0.000 description 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- -1 phosphoric acid organic esters Chemical class 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005406 washing Methods 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/14—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom belonging to a ring other than a six-membered aromatic ring
-
- 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
-
- 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
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
-
- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/242,544 US6703529B1 (en) | 2002-09-12 | 2002-09-12 | Process for oxidation of cyclohexane |
| US10/242,544 | 2002-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050044918A true KR20050044918A (ko) | 2005-05-13 |
Family
ID=31887781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057004213A Ceased KR20050044918A (ko) | 2002-09-12 | 2003-09-09 | 시클로헥산 산화 방법 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6703529B1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1539665B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2005539066A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20050044918A (cg-RX-API-DMAC7.html) |
| CN (1) | CN1319924C (cg-RX-API-DMAC7.html) |
| AU (1) | AU2003267072A1 (cg-RX-API-DMAC7.html) |
| TW (1) | TW200410924A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2004024657A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6814867B2 (en) * | 2002-09-12 | 2004-11-09 | Inuista North America S.à.r.l. | Process for reducing chromium in nonvolatile residue resulting from air oxidation of cyclohexane |
| FR2878847B1 (fr) | 2004-12-07 | 2007-01-05 | Rhodia Chimie Sa | Procede de preparation de cyclohexanone |
| CN100460374C (zh) * | 2006-01-06 | 2009-02-11 | 中国石油天然气股份有限公司 | 一种延长醇酮装置碱洗周期的方法 |
| JP5350244B2 (ja) * | 2006-08-18 | 2013-11-27 | インヴィスタ テクノロジーズ エスアエルエル | イオン性液体を用いた抽出方法 |
| PL2384344T3 (pl) * | 2009-01-30 | 2020-04-30 | Invista Textiles (U.K.) Limited | Aromatyczne poliestropoliole, pianki poliuretanowe modyfikowane izocyjanuratem i sposoby ich wytwarzania |
| RU2402520C1 (ru) * | 2009-05-28 | 2010-10-27 | Институт Катализа Им. Г.К. Борескова Сибирского Отделения Российской Академии Наук | Способ получения смеси циклогексанола и циклогексанона |
| RU2409548C1 (ru) * | 2009-05-28 | 2011-01-20 | Институт Катализа Им. Г.К. Борескова Сибирского Отделения Российской Академии Наук | Способ получения смеси циклогексанола и циклогексанона |
| RU2458903C1 (ru) * | 2010-12-23 | 2012-08-20 | Открытое акционерное общество "Щекиноазот" | Способ получения циклогексанона и циклогексанола и установка для его осуществления |
| WO2012173938A1 (en) | 2011-06-13 | 2012-12-20 | Invista Technologies S.A.R.L. | Aliphatic polyester polyols from cyclohexane oxidation byproduct streams as precursors for polyurethane and polyisocyanurate polymers |
| JP6058650B2 (ja) | 2011-06-17 | 2017-01-11 | インビスタ テクノロジーズ エス．アー．エール．エル． | 廃棄流中のモノマー含有量を増大させるためのヒドロラーゼの使用 |
| CN104011216A (zh) | 2011-06-30 | 2014-08-27 | 英威达技术有限责任公司 | 用于生产尼龙-7、尼龙-7,7和聚酯的生物转化工艺 |
| US9102960B2 (en) | 2011-12-16 | 2015-08-11 | Invista North America S.á.r.l. | Methods of producing 6-carbon chemicals via CoA-dependent carbon chain elongation associated with carbon storage |
| US9102958B2 (en) | 2011-12-16 | 2015-08-11 | Invista North America S.á.r.l. | Methods of producing 6-carbon chemicals via CoA-dependent carbon chain elongation associated with carbon storage |
| KR20150036439A (ko) | 2012-07-19 | 2015-04-07 | 인비스타 테크놀러지스 에스.에이 알.엘. | 사이클로헥산의 산화를 위한 공정 |
| CN104583163A (zh) * | 2012-07-19 | 2015-04-29 | 因温斯特技术公司 | 氧化环己烷的方法 |
| CN104583164A (zh) | 2012-07-19 | 2015-04-29 | 因温斯特技术公司 | 用于纯化环己烷空气氧化产物流的方法 |
| KR20150036632A (ko) | 2012-07-19 | 2015-04-07 | 인비스타 테크놀러지스 에스.에이 알.엘. | 수소화 촉매의 재생 |
| WO2014093847A2 (en) | 2012-12-14 | 2014-06-19 | Invista North America S.A.R.L. | METHODS OF PRODUCING 7-CARBON CHEMICALS VIA CoA-DEPENDENT CARBON CHAIN ELONGATION ASSOCIATED WITH CARBON STORAGE |
| EP2935109A1 (en) | 2012-12-18 | 2015-10-28 | Invista Technologies S.à.r.l. | Process for producing hydrogen cyanide and recovering hydrogen |
| US9617572B2 (en) | 2012-12-31 | 2017-04-11 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals via aromatic compounds |
| WO2014105790A2 (en) | 2012-12-31 | 2014-07-03 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals via c1 carbon chain elongation associated with coenzyme b synthesis |
| EP2938732A1 (en) | 2012-12-31 | 2015-11-04 | Invista Technologies S.à.r.l. | Methods of producing 7-carbon chemicals from long chain fatty acids via oxidative cleavage |
| US9580733B2 (en) | 2012-12-31 | 2017-02-28 | Invista North America S.A.R.L. | Methods of producing 6-carbon chemicals via methyl-ester shielded carbon chain elongation |
| EP2938731A2 (en) | 2012-12-31 | 2015-11-04 | Invista Technologies S.A R.L. | Methods of producing 7-carbon chemicals via carbon chain elongation associated with cyclohexane carboxylate synthesis |
| WO2014105794A2 (en) | 2012-12-31 | 2014-07-03 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals via methyl-ester shielded carbon chain elongation |
| WO2014105797A2 (en) | 2012-12-31 | 2014-07-03 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals via pyruvate and succinate semialdehyde aldol condensation |
| CN104557497A (zh) * | 2013-10-09 | 2015-04-29 | 中国石油化工股份有限公司 | 一种提高环己基过氧化氢分解酮醇比的方法 |
| WO2015176026A1 (en) | 2014-05-15 | 2015-11-19 | Invista North America S.á.r.l. | Methods of producing 6-carbon chemicals using 2,6-diaminopimelate as precursor to 2-aminopimelate |
| CN106795534A (zh) | 2014-06-16 | 2017-05-31 | 英威达技术有限责任公司 | 用于生物合成化合物的方法、试剂和细胞 |
| US9777302B2 (en) | 2014-06-16 | 2017-10-03 | Invista North America S.A.R.L. | Methods, reagents and cells for biosynthesizing compounds |
| US20170152531A1 (en) | 2014-06-16 | 2017-06-01 | North America S.A.R.L. | Process for producing glutarate and glutaric acid methyl ester |
| WO2015195654A1 (en) | 2014-06-16 | 2015-12-23 | Invista Technologies S.A R.L. | Methods, reagents and cells for biosynthesizing compounds |
| CN104945213B (zh) * | 2014-07-07 | 2017-01-11 | 山东勇智化工有限公司 | 干燥塔负压干燥工艺 |
| RU2717342C1 (ru) | 2015-10-01 | 2020-03-23 | Эдвансикс Ресинс Энд Кемикалс Ллк | Катализаторы на основе наночастиц для превращения циклогексанола в циклогексанон |
| CN105315128B (zh) * | 2015-10-28 | 2017-04-12 | 江西科苑生物药业有限公司 | 一种环己烷氧化制备ka油的方法 |
| CN106995463B (zh) * | 2017-03-31 | 2019-11-08 | 中国石油化工股份有限公司 | 一种油溶性铬酸异辛酯催化体系 |
| RU2673541C1 (ru) * | 2017-10-13 | 2018-11-28 | Открытое акционерное общество "Щекиноазот" | Способ получения циклогексанона, циклогексанола и циклогексилгидропероксида, установка для его осуществления и устройство абсорбции реакционных газов и предварительного окисления циклогексана |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1590958A (en) * | 1976-12-31 | 1981-06-10 | Ici Ltd | Oxidation of cyclohexane |
| SU1323537A1 (ru) | 1982-01-22 | 1987-07-15 | Рубежанский филиал Ворошиловградского машиностроительного института | Способ очистки сточных вод от шестивалентного хрома |
| US4465861A (en) | 1983-04-11 | 1984-08-14 | E. I. Du Pont De Nemours And Company | Process for producing a mixture containing cyclohexanol and cyclohexanone |
| US4720592A (en) | 1986-09-05 | 1988-01-19 | E. I. Du Pont De Nemours And Company | Preparation of cyclohexanone and cyclohexanol |
| RU2023674C1 (ru) | 1991-07-15 | 1994-11-30 | Ляпкин Александр Александрович | Способ очистки сточных вод от соединений хрома |
| US5932109A (en) | 1994-06-02 | 1999-08-03 | Griffin Chemical Company | Plating rinse water treatment |
| JP3632233B2 (ja) * | 1995-03-10 | 2005-03-23 | 三菱化学株式会社 | α−オレフイン低重合体の製造方法 |
| JP3572811B2 (ja) * | 1996-06-17 | 2004-10-06 | 東ソー株式会社 | クロムを含有する廃触媒の処理方法 |
| US5780683A (en) * | 1996-09-11 | 1998-07-14 | Abb Lummus Global Inc. | Cyclohexane oxidation |
| JP2001058192A (ja) | 1999-08-23 | 2001-03-06 | Matsushita Sangyo Kk | 六価クロムの除去方法 |
| US6814867B2 (en) * | 2002-09-12 | 2004-11-09 | Inuista North America S.à.r.l. | Process for reducing chromium in nonvolatile residue resulting from air oxidation of cyclohexane |
-
2002
- 2002-09-12 US US10/242,544 patent/US6703529B1/en not_active Expired - Lifetime
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- 2003-07-03 TW TW092118221A patent/TW200410924A/zh unknown
- 2003-09-09 WO PCT/US2003/028261 patent/WO2004024657A2/en not_active Ceased
- 2003-09-09 AU AU2003267072A patent/AU2003267072A1/en not_active Abandoned
- 2003-09-09 EP EP03749547A patent/EP1539665B1/en not_active Expired - Lifetime
- 2003-09-09 JP JP2004536396A patent/JP2005539066A/ja active Pending
- 2003-09-09 KR KR1020057004213A patent/KR20050044918A/ko not_active Ceased
- 2003-09-09 CN CNB038215535A patent/CN1319924C/zh not_active Expired - Fee Related
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|---|---|
| CN1681759A (zh) | 2005-10-12 |
| US6703529B1 (en) | 2004-03-09 |
| JP2005539066A (ja) | 2005-12-22 |
| AU2003267072A1 (en) | 2004-04-30 |
| WO2004024657A2 (en) | 2004-03-25 |
| TW200410924A (en) | 2004-07-01 |
| US20040054235A1 (en) | 2004-03-18 |
| EP1539665A2 (en) | 2005-06-15 |
| AU2003267072A8 (en) | 2004-04-30 |
| CN1319924C (zh) | 2007-06-06 |
| WO2004024657A3 (en) | 2004-08-05 |
| EP1539665A4 (en) | 2006-07-26 |
| EP1539665B1 (en) | 2011-11-09 |
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