BE579518A - - Google Patents

Info

Publication number

BE579518A

BE579518A BE579518DA BE579518A BE 579518 A BE579518 A BE 579518A BE 579518D A BE579518D A BE 579518DA BE 579518 A BE579518 A BE 579518A

Authority

BE

Belgium

Prior art keywords

aldehyde

oxidation

oxygen

peracid

mixture

Prior art date

Links

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• 150000001299 aldehydes Chemical class 0.000 claims description 70
• 238000007254 oxidation reaction Methods 0.000 claims description 39
• 150000004965 peroxy acids Chemical class 0.000 claims description 39
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 38
• 230000003647 oxidation Effects 0.000 claims description 38
• 239000001301 oxygen Substances 0.000 claims description 38
• 229910052760 oxygen Inorganic materials 0.000 claims description 38
• 239000000203 mixture Substances 0.000 claims description 23
• 238000000034 method Methods 0.000 claims description 15
• 238000006243 chemical reaction Methods 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 12
• 239000007789 gas Substances 0.000 claims description 10
• 239000003054 catalyst Substances 0.000 claims description 9
• 238000001816 cooling Methods 0.000 claims description 8
• 159000000014 iron salts Chemical class 0.000 claims description 4
• 239000003507 refrigerant Substances 0.000 claims description 4
• 239000002904 solvent Substances 0.000 claims description 4
• 238000003756 stirring Methods 0.000 claims description 3
• 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
• 150000002148 esters Chemical class 0.000 claims description 2
• 229930195733 hydrocarbon Natural products 0.000 claims description 2
• 150000002430 hydrocarbons Chemical class 0.000 claims description 2
• 150000002576 ketones Chemical class 0.000 claims description 2
• 108090000623 proteins and genes Proteins 0.000 claims description 2
• 101150108928 CCC1 gene Proteins 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 20
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 14
• 239000000047 product Substances 0.000 description 12
• 239000002253 acid Substances 0.000 description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 229910001385 heavy metal Inorganic materials 0.000 description 6
• 238000007086 side reaction Methods 0.000 description 5
• GOKIPOOTKLLKDI-UHFFFAOYSA-N acetic acid;iron Chemical compound [Fe].CC(O)=O.CC(O)=O.CC(O)=O GOKIPOOTKLLKDI-UHFFFAOYSA-N 0.000 description 4
• 238000010521 absorption reaction Methods 0.000 description 3
• IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 3
• 230000004913 activation Effects 0.000 description 3
• 150000008064 anhydrides Chemical class 0.000 description 3
• 150000001875 compounds Chemical class 0.000 description 3
• 229910052742 iron Inorganic materials 0.000 description 3
• 229910052751 metal Inorganic materials 0.000 description 3
• 239000002184 metal Substances 0.000 description 3
• 238000002360 preparation method Methods 0.000 description 3
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 2
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
• 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 2
• NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
• 229940011182 cobalt acetate Drugs 0.000 description 2
• GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
• QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 2
• 238000004821 distillation Methods 0.000 description 2
• -1 drunk Chemical compound 0.000 description 2
• 238000002474 experimental method Methods 0.000 description 2
• 238000004880 explosion Methods 0.000 description 2
• DGWNGWVWFZCEGL-UHFFFAOYSA-L iron(2+);4-oxopentanoate Chemical compound [Fe+2].CC(=O)CCC([O-])=O.CC(=O)CCC([O-])=O DGWNGWVWFZCEGL-UHFFFAOYSA-L 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 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 2
• 230000001105 regulatory effect Effects 0.000 description 2
• 101150084750 1 gene Proteins 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
• DWRXEIKFVUSVAW-UHFFFAOYSA-N C(C(=O)C)CC(C)=O.[Fe] Chemical compound C(C(=O)C)CC(C)=O.[Fe] DWRXEIKFVUSVAW-UHFFFAOYSA-N 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
• 101100065704 Enterococcus faecium entP gene Proteins 0.000 description 1
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
• WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
• 150000003934 aromatic aldehydes Chemical class 0.000 description 1
• 238000010923 batch production Methods 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• YTCZZXIRLARSET-VJRSQJMHSA-M beraprost sodium Chemical compound [Na+].O([C@H]1C[C@@H](O)[C@@H]([C@@H]21)/C=C/[C@@H](O)C(C)CC#CC)C1=C2C=CC=C1CCCC([O-])=O YTCZZXIRLARSET-VJRSQJMHSA-M 0.000 description 1
• LBAYFEDWGHXMSM-UHFFFAOYSA-N butaneperoxoic acid Chemical compound CCCC(=O)OO LBAYFEDWGHXMSM-UHFFFAOYSA-N 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 238000006555 catalytic reaction Methods 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 239000002826 coolant Substances 0.000 description 1
• 239000000498 cooling water Substances 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 230000002939 deleterious effect Effects 0.000 description 1
• 230000001066 destructive effect Effects 0.000 description 1
• 230000001627 detrimental effect Effects 0.000 description 1
• 238000010586 diagram Methods 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• 229910001882 dioxygen Inorganic materials 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• FXNJQPDKIOMNLN-UHFFFAOYSA-N iron;2-oxopropyl acetate Chemical compound [Fe].CC(=O)COC(C)=O FXNJQPDKIOMNLN-UHFFFAOYSA-N 0.000 description 1
• 150000002739 metals Chemical class 0.000 description 1
• 229910052759 nickel Inorganic materials 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• 238000006213 oxygenation reaction Methods 0.000 description 1
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 229910052720 vanadium Inorganic materials 0.000 description 1
• GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1