DE2124124B - - Google Patents

Info

Publication number

DE2124124B

DE2124124B DE2124124B DE 2124124 B DE2124124 B DE 2124124B DE 2124124 B DE2124124 B DE 2124124B

Authority

DE

Germany

Prior art keywords

cyclohexane

oxidation

mono

chromium

soluble

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

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• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 16
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
• 239000003054 catalyst Substances 0.000 claims description 9
• 230000003647 oxidation Effects 0.000 claims description 8
• 238000007254 oxidation reaction Methods 0.000 claims description 8
• 239000007788 liquid Substances 0.000 claims description 6
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 5
• 239000007791 liquid phase Substances 0.000 claims description 5
• 239000000203 mixture Substances 0.000 claims description 5
• 239000002253 acid Substances 0.000 claims description 4
• 238000009835 boiling Methods 0.000 claims description 4
• 238000000354 decomposition reaction Methods 0.000 claims description 4
• 239000007789 gas Substances 0.000 claims description 4
• 150000002978 peroxides Chemical class 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 150000002148 esters Chemical class 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 239000012071 phase Substances 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 238000004821 distillation Methods 0.000 claims description 2
• FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 claims description 2
• 239000011541 reaction mixture Substances 0.000 claims description 2
• 238000000034 method Methods 0.000 claims 10
• 125000004429 atom Chemical group 0.000 claims 7
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 6
• -1 alkyl radical Chemical group 0.000 claims 6
• 229910052804 chromium Inorganic materials 0.000 claims 5
• 239000011651 chromium Substances 0.000 claims 5
• VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 4
• 238000006243 chemical reaction Methods 0.000 claims 4
• 235000011007 phosphoric acid Nutrition 0.000 claims 4
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 3
• 125000004432 carbon atom Chemical group C* 0.000 claims 3
• 150000001844 chromium Chemical class 0.000 claims 3
• 238000010924 continuous production Methods 0.000 claims 3
• 150000001924 cycloalkanes Chemical class 0.000 claims 3
• 238000010438 heat treatment Methods 0.000 claims 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
• 229910052698 phosphorus Inorganic materials 0.000 claims 3
• 239000011574 phosphorus Substances 0.000 claims 3
• 150000003254 radicals Chemical class 0.000 claims 3
• 239000012429 reaction media Substances 0.000 claims 3
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
• 150000005690 diesters Chemical class 0.000 claims 2
• 229910001882 dioxygen Inorganic materials 0.000 claims 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
• 150000002432 hydroperoxides Chemical class 0.000 claims 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
• SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
• 239000001361 adipic acid Substances 0.000 claims 1
• 235000011037 adipic acid Nutrition 0.000 claims 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 229910017052 cobalt Inorganic materials 0.000 claims 1
• 239000010941 cobalt Substances 0.000 claims 1
• GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
• SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 claims 1
• JTXUVYOABGUBMX-UHFFFAOYSA-N didodecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCC JTXUVYOABGUBMX-UHFFFAOYSA-N 0.000 claims 1
• FRXGWNKDEMTFPL-UHFFFAOYSA-N dioctadecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCCCC FRXGWNKDEMTFPL-UHFFFAOYSA-N 0.000 claims 1
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• MDLWEBWGXACWGE-UHFFFAOYSA-N octadecane Chemical compound [CH2]CCCCCCCCCCCCCCCCC MDLWEBWGXACWGE-UHFFFAOYSA-N 0.000 claims 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 230000036647 reaction Effects 0.000 claims 1
• 239000000126 substance Substances 0.000 claims 1
• 238000011144 upstream manufacturing Methods 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• 239000008346 aqueous phase Substances 0.000 description 2
• 230000001590 oxidative effect Effects 0.000 description 2
• LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical compound CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-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
• 150000007513 acids Chemical class 0.000 description 1
• BJZJDEOGMBZSLE-UHFFFAOYSA-N cyclohexane;hydrate Chemical compound O.C1CCCCC1 BJZJDEOGMBZSLE-UHFFFAOYSA-N 0.000 description 1
• 238000005406 washing Methods 0.000 description 1

Cited By (1)