GB1561494A - Process and apparatus for oxidizing cycloalkanes - Google Patents
Process and apparatus for oxidizing cycloalkanes Download PDFInfo
- Publication number
- GB1561494A GB1561494A GB47723/76A GB4772376A GB1561494A GB 1561494 A GB1561494 A GB 1561494A GB 47723/76 A GB47723/76 A GB 47723/76A GB 4772376 A GB4772376 A GB 4772376A GB 1561494 A GB1561494 A GB 1561494A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohexane
- oxidation
- cycloalkane
- water
- reactor
- 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.)
- Expired
Links
- 150000001924 cycloalkanes Chemical class 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 30
- 230000001590 oxidative effect Effects 0.000 title claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 60
- 230000003647 oxidation Effects 0.000 claims abstract description 55
- 239000007789 gas Substances 0.000 claims abstract description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 239000007791 liquid phase Substances 0.000 claims abstract description 13
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 11
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 50
- 239000007788 liquid Substances 0.000 claims description 17
- 238000004821 distillation Methods 0.000 claims description 12
- 239000008346 aqueous phase Substances 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000004140 cleaning Methods 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 230000000052 comparative effect Effects 0.000 claims description 2
- 150000001934 cyclohexanes Chemical class 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 238000002474 experimental method Methods 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 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 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 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
- BCEIUDAMUFAQMG-UHFFFAOYSA-M CC(C)(C)O[Cr](O)(=O)=O Chemical compound CC(C)(C)O[Cr](O)(=O)=O BCEIUDAMUFAQMG-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229960002645 boric acid Drugs 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- XEHUIDSUOAGHBW-UHFFFAOYSA-N chromium;pentane-2,4-dione Chemical compound [Cr].CC(=O)CC(C)=O.CC(=O)CC(C)=O.CC(=O)CC(C)=O XEHUIDSUOAGHBW-UHFFFAOYSA-N 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- IFSWBZCGMGEHLE-UHFFFAOYSA-L cobalt(2+);naphthalene-2-carboxylate Chemical compound [Co+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 IFSWBZCGMGEHLE-UHFFFAOYSA-L 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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)
- 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 |
|---|---|---|---|
| NL7513664A NL7513664A (nl) | 1975-11-22 | 1975-11-22 | Werkwijze en inrichting voor het oxideren van cy- cloalkanen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1561494A true GB1561494A (en) | 1980-02-20 |
Family
ID=19824904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47723/76A Expired GB1561494A (en) | 1975-11-22 | 1976-11-16 | Process and apparatus for oxidizing cycloalkanes |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5265249A (enExample) |
| AR (1) | AR211401Q (enExample) |
| BE (1) | BE848408A (enExample) |
| BR (1) | BR7607811A (enExample) |
| CA (1) | CA1080255A (enExample) |
| CH (1) | CH627427A5 (enExample) |
| DD (1) | DD127649A5 (enExample) |
| DE (1) | DE2652691C2 (enExample) |
| ES (1) | ES453518A1 (enExample) |
| FR (1) | FR2332255A1 (enExample) |
| GB (1) | GB1561494A (enExample) |
| IN (1) | IN143447B (enExample) |
| IT (1) | IT1069818B (enExample) |
| MX (1) | MX146065A (enExample) |
| NL (1) | NL7513664A (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1892232A1 (en) * | 2006-08-21 | 2008-02-27 | Desmet Ballestra Oleo s.p.a. | Production of esters of fatty acids and lower alcohols |
| US7615241B2 (en) | 2004-09-15 | 2009-11-10 | De Smet Engineering N.V. | Vapor scrubbing process and apparatus |
| US7670634B2 (en) | 2003-08-06 | 2010-03-02 | De Smet Engineering N.V. | Method for vacuum stripping of oils and fats |
| US7696369B2 (en) | 2004-08-06 | 2010-04-13 | De Smet Engineering N.V. | Oil Recuperation process |
| US7892335B2 (en) | 2006-09-28 | 2011-02-22 | N.V. Desmet Ballestra Engineering S.A. | Phase transfer apparatus and process |
| US8142178B2 (en) | 2007-08-01 | 2012-03-27 | N.V. Desmet Ballestra Engineering S.A. | Device for desolventising under reduced pressure |
| US8203014B2 (en) | 2006-01-20 | 2012-06-19 | N.V. De Smet Engineering S.A. | Fractionation processes and devices for oils and fats |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1120445B (de) * | 1959-02-26 | 1961-12-28 | Chemstrand Corp | Verfahren zur Oxydation von Cyclohexan in fluessiger Phase |
| DE1150674B (de) * | 1961-06-05 | 1963-06-27 | Huels Chemische Werke Ag | Verfahren zur mehrstufigen Fluessigphasenoxydation von Cyclohexan |
| NL283634A (enExample) * | 1961-09-26 | |||
| GB1172655A (en) * | 1968-03-06 | 1969-12-03 | Toa Gosei Chem Ind | A process for Continuously Oxidising Cyclohexane |
| NL157587B (nl) * | 1968-03-23 | 1978-08-15 | Stamicarbon | Werkwijze voor het oxyderen van cyclohexaan. |
| PL71186B1 (enExample) * | 1969-04-15 | 1974-04-30 | ||
| BE790104A (fr) * | 1971-10-14 | 1973-04-13 | Stamicarbon | Procede continu d'obtention de cyclohexanone |
-
1975
- 1975-11-22 NL NL7513664A patent/NL7513664A/xx not_active Application Discontinuation
-
1976
- 1976-11-16 GB GB47723/76A patent/GB1561494A/en not_active Expired
- 1976-11-17 BE BE172415A patent/BE848408A/xx not_active IP Right Cessation
- 1976-11-17 IN IN2058/CAL/77A patent/IN143447B/en unknown
- 1976-11-18 AR AR265523A patent/AR211401Q/es unknown
- 1976-11-18 FR FR7634756A patent/FR2332255A1/fr active Granted
- 1976-11-18 CA CA266,006A patent/CA1080255A/en not_active Expired
- 1976-11-19 CH CH1461476A patent/CH627427A5/de not_active IP Right Cessation
- 1976-11-19 DE DE2652691A patent/DE2652691C2/de not_active Expired
- 1976-11-19 IT IT52285/76A patent/IT1069818B/it active
- 1976-11-20 ES ES453518A patent/ES453518A1/es not_active Expired
- 1976-11-22 JP JP51140640A patent/JPS5265249A/ja active Granted
- 1976-11-22 DD DD195889A patent/DD127649A5/xx unknown
- 1976-11-22 MX MX167112A patent/MX146065A/es unknown
- 1976-11-22 BR BR7607811A patent/BR7607811A/pt unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7670634B2 (en) | 2003-08-06 | 2010-03-02 | De Smet Engineering N.V. | Method for vacuum stripping of oils and fats |
| US7696369B2 (en) | 2004-08-06 | 2010-04-13 | De Smet Engineering N.V. | Oil Recuperation process |
| US7615241B2 (en) | 2004-09-15 | 2009-11-10 | De Smet Engineering N.V. | Vapor scrubbing process and apparatus |
| US8203014B2 (en) | 2006-01-20 | 2012-06-19 | N.V. De Smet Engineering S.A. | Fractionation processes and devices for oils and fats |
| EP1892232A1 (en) * | 2006-08-21 | 2008-02-27 | Desmet Ballestra Oleo s.p.a. | Production of esters of fatty acids and lower alcohols |
| US7892335B2 (en) | 2006-09-28 | 2011-02-22 | N.V. Desmet Ballestra Engineering S.A. | Phase transfer apparatus and process |
| US8142178B2 (en) | 2007-08-01 | 2012-03-27 | N.V. Desmet Ballestra Engineering S.A. | Device for desolventising under reduced pressure |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2332255A1 (fr) | 1977-06-17 |
| BE848408A (nl) | 1977-05-17 |
| AR211401Q (es) | 1977-12-15 |
| IT1069818B (it) | 1985-03-25 |
| JPS6115053B2 (enExample) | 1986-04-22 |
| IN143447B (enExample) | 1977-11-26 |
| CA1080255A (en) | 1980-06-24 |
| FR2332255B1 (enExample) | 1982-11-05 |
| DE2652691A1 (de) | 1977-06-02 |
| CH627427A5 (en) | 1982-01-15 |
| BR7607811A (pt) | 1977-10-11 |
| MX146065A (es) | 1982-05-11 |
| DE2652691C2 (de) | 1986-05-07 |
| DD127649A5 (enExample) | 1977-10-05 |
| JPS5265249A (en) | 1977-05-30 |
| ES453518A1 (es) | 1977-11-16 |
| NL7513664A (nl) | 1977-05-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |