BE555380A - - Google Patents

Info

Publication number

BE555380A

BE555380A BE555380DA BE555380A BE 555380 A BE555380 A BE 555380A BE 555380D A BE555380D A BE 555380DA BE 555380 A BE555380 A BE 555380A

Authority

BE

Belgium

Prior art keywords

oxime

ketone

reaction

cycloaliphatic

hydroxylamine

Prior art date

Links

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• 150000002923 oximes Chemical class 0.000 claims description 30
• 238000000034 method Methods 0.000 claims description 6
• 150000002576 ketones Chemical class 0.000 description 22
• 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 16
• ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 15
• 238000006243 chemical reaction Methods 0.000 description 15
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 14
• 239000007788 liquid Substances 0.000 description 10
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
• 239000000908 ammonium hydroxide Substances 0.000 description 8
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 7
• 238000000605 extraction Methods 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
• 238000000926 separation method Methods 0.000 description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
• 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
• 235000011130 ammonium sulphate Nutrition 0.000 description 3
• 238000004519 manufacturing process Methods 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 229910017912 NH2OH Inorganic materials 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 239000006227 byproduct Substances 0.000 description 2
• VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
• BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
• 150000003951 lactams Chemical class 0.000 description 2
• 238000006386 neutralization reaction Methods 0.000 description 2
• 229910052757 nitrogen Inorganic materials 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 238000005057 refrigeration Methods 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• 230000009466 transformation Effects 0.000 description 2
• VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 125000000217 alkyl group Chemical group 0.000 description 1
• 239000012295 chemical reaction liquid Substances 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 238000010924 continuous production Methods 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000003337 fertilizer Substances 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 239000012265 solid product Substances 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 238000011282 treatment Methods 0.000 description 1