JPH01102035A - シクロヘキサン酸化生成物の選択率改善法 - Google Patents
シクロヘキサン酸化生成物の選択率改善法Info
- Publication number
- JPH01102035A JPH01102035A JP25816487A JP25816487A JPH01102035A JP H01102035 A JPH01102035 A JP H01102035A JP 25816487 A JP25816487 A JP 25816487A JP 25816487 A JP25816487 A JP 25816487A JP H01102035 A JPH01102035 A JP H01102035A
- Authority
- JP
- Japan
- Prior art keywords
- conversion rate
- mol
- reaction
- approximately
- cyclohexane
- 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.)
- Pending
Links
- 230000006872 improvement Effects 0.000 title description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 260
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 141
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 141
- 239000001301 oxygen Substances 0.000 claims abstract description 141
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 75
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000007791 liquid phase Substances 0.000 claims abstract description 60
- 230000003647 oxidation Effects 0.000 claims abstract description 60
- 239000007789 gas Substances 0.000 claims abstract description 45
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 10
- 239000002184 metal Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 95
- 230000008569 process Effects 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical group O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 18
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract description 15
- 239000012071 phase Substances 0.000 description 31
- 239000006227 byproduct Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 230000000694 effects Effects 0.000 description 17
- 238000013461 design Methods 0.000 description 14
- 229930195733 hydrocarbon Natural products 0.000 description 14
- 150000002430 hydrocarbons Chemical class 0.000 description 14
- 238000012546 transfer Methods 0.000 description 13
- 239000000376 reactant Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 description 6
- 230000037361 pathway Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 4
- 230000006798 recombination Effects 0.000 description 4
- 238000005215 recombination Methods 0.000 description 4
- 229920002292 Nylon 6 Polymers 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- RQXXCWHCUOJQGR-UHFFFAOYSA-N 1,1-dichlorohexane Chemical compound CCCCCC(Cl)Cl RQXXCWHCUOJQGR-UHFFFAOYSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000003889 chemical engineering Methods 0.000 description 2
- 238000001311 chemical methods and process Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- -1 estrides Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 238000003541 multi-stage reaction Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000036284 oxygen consumption Effects 0.000 description 2
- 230000005501 phase interface Effects 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 239000011265 semifinished product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 1
- 101100323029 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) alc-1 gene Proteins 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 206010042255 Struck by lightning Diseases 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001553 barium compounds Chemical class 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL26142786A PL149206B1 (en) | 1986-09-16 | 1986-09-16 | Procedure for oxidation of cyclohexane in liquid phase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01102035A true JPH01102035A (ja) | 1989-04-19 |
Family
ID=20032670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25816487A Pending JPH01102035A (ja) | 1986-09-16 | 1987-10-13 | シクロヘキサン酸化生成物の選択率改善法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPH01102035A (de) |
| CN (1) | CN1020591C (de) |
| DD (1) | DD263977A5 (de) |
| IN (1) | IN171637B (de) |
| PL (1) | PL149206B1 (de) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6479705B2 (en) | 1999-12-14 | 2002-11-12 | Sumitomo Chemical Company, Limited | Process for preparing ketone, alcohol and hydroperoxide |
| JP2011184380A (ja) * | 2010-03-10 | 2011-09-22 | Kao Corp | エーテルカルボキシレートの製造方法 |
| JP2011184379A (ja) * | 2010-03-10 | 2011-09-22 | Kao Corp | エーテルカルボキシレートの製造方法 |
| US8940933B2 (en) | 2009-12-28 | 2015-01-27 | Kao Corporation | Method for producing polyoxyalkylene alkyl ether carboxylic acid and salt thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9221737B2 (en) * | 2012-07-19 | 2015-12-29 | Invista North America S.A.R.L. | Process for the oxidation of cyclohexane |
-
1986
- 1986-09-16 PL PL26142786A patent/PL149206B1/pl unknown
-
1987
- 1987-09-16 DD DD30700687A patent/DD263977A5/de not_active IP Right Cessation
- 1987-09-18 IN IN825/DEL/87A patent/IN171637B/en unknown
- 1987-10-13 JP JP25816487A patent/JPH01102035A/ja active Pending
- 1987-10-19 CN CN 87106968 patent/CN1020591C/zh not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6479705B2 (en) | 1999-12-14 | 2002-11-12 | Sumitomo Chemical Company, Limited | Process for preparing ketone, alcohol and hydroperoxide |
| US8940933B2 (en) | 2009-12-28 | 2015-01-27 | Kao Corporation | Method for producing polyoxyalkylene alkyl ether carboxylic acid and salt thereof |
| JP2011184380A (ja) * | 2010-03-10 | 2011-09-22 | Kao Corp | エーテルカルボキシレートの製造方法 |
| JP2011184379A (ja) * | 2010-03-10 | 2011-09-22 | Kao Corp | エーテルカルボキシレートの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DD263977A5 (de) | 1989-01-18 |
| PL261427A1 (en) | 1988-06-09 |
| PL149206B1 (en) | 1990-01-31 |
| CN1032655A (zh) | 1989-05-03 |
| CN1020591C (zh) | 1993-05-12 |
| IN171637B (de) | 1992-11-28 |
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