CA2104068C - Chemical process - Google Patents
Chemical process Download PDFInfo
- Publication number
- CA2104068C CA2104068C CA002104068A CA2104068A CA2104068C CA 2104068 C CA2104068 C CA 2104068C CA 002104068 A CA002104068 A CA 002104068A CA 2104068 A CA2104068 A CA 2104068A CA 2104068 C CA2104068 C CA 2104068C
- Authority
- CA
- Canada
- Prior art keywords
- magnesium
- reaction
- mole
- group
- formaldehyde
- 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 - Lifetime
Links
- 238000001311 chemical methods and process Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 117
- 238000000034 method Methods 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 229910052751 metal Inorganic materials 0.000 claims abstract description 24
- 239000002184 metal Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 230000000737 periodic effect Effects 0.000 claims abstract description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 261
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 165
- 229910052749 magnesium Inorganic materials 0.000 claims description 67
- 239000011777 magnesium Substances 0.000 claims description 66
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 60
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 58
- 239000002904 solvent Substances 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 20
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical group [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 claims description 17
- -1 magnesium alkoxide Chemical class 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- KRPXAHXWPZLBKL-UHFFFAOYSA-L magnesium;diphenoxide Chemical compound [Mg+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 KRPXAHXWPZLBKL-UHFFFAOYSA-L 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- NXWFBGYARFPCAQ-UHFFFAOYSA-L magnesium;2-formylphenolate Chemical compound [Mg+2].[O-]C1=CC=CC=C1C=O.[O-]C1=CC=CC=C1C=O NXWFBGYARFPCAQ-UHFFFAOYSA-L 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 239000004411 aluminium Substances 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical class [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 150000002443 hydroxylamines Chemical class 0.000 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- LCSPHILVKFKAQH-UHFFFAOYSA-L magnesium;2-formyl-4-nonylphenolate Chemical group [Mg+2].CCCCCCCCCC1=CC=C([O-])C(C=O)=C1.CCCCCCCCCC1=CC=C([O-])C(C=O)=C1 LCSPHILVKFKAQH-UHFFFAOYSA-L 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 239000003880 polar aprotic solvent Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000003609 titanium compounds Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- FTASRILAGVAYFM-UHFFFAOYSA-L magnesium;4-nonylphenolate Chemical group [Mg+2].CCCCCCCCCC1=CC=C([O-])C=C1.CCCCCCCCCC1=CC=C([O-])C=C1 FTASRILAGVAYFM-UHFFFAOYSA-L 0.000 claims 1
- 239000000243 solution Substances 0.000 description 114
- 238000010992 reflux Methods 0.000 description 75
- 238000004821 distillation Methods 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- 239000010410 layer Substances 0.000 description 44
- 239000000203 mixture Substances 0.000 description 41
- 239000002002 slurry Substances 0.000 description 38
- 238000000926 separation method Methods 0.000 description 33
- 238000001816 cooling Methods 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 31
- 238000005194 fractionation Methods 0.000 description 27
- 239000007787 solid Substances 0.000 description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 26
- 239000001117 sulphuric acid Substances 0.000 description 26
- 235000011149 sulphuric acid Nutrition 0.000 description 26
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 24
- 239000006227 byproduct Substances 0.000 description 24
- 239000012044 organic layer Substances 0.000 description 23
- 229930040373 Paraformaldehyde Natural products 0.000 description 19
- 229920002866 paraformaldehyde Polymers 0.000 description 19
- 239000000725 suspension Substances 0.000 description 18
- 238000006146 oximation reaction Methods 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 17
- 235000002639 sodium chloride Nutrition 0.000 description 17
- 230000002378 acidificating effect Effects 0.000 description 16
- VGYYSIDKAKXZEE-UHFFFAOYSA-L hydroxylammonium sulfate Chemical compound O[NH3+].O[NH3+].[O-]S([O-])(=O)=O VGYYSIDKAKXZEE-UHFFFAOYSA-L 0.000 description 16
- 238000013019 agitation Methods 0.000 description 15
- 238000009835 boiling Methods 0.000 description 15
- 238000002390 rotary evaporation Methods 0.000 description 15
- 238000001035 drying Methods 0.000 description 14
- 238000006170 formylation reaction Methods 0.000 description 14
- 238000010306 acid treatment Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229940007550 benzyl acetate Drugs 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 238000001556 precipitation Methods 0.000 description 11
- 239000006184 cosolvent Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 230000011514 reflex Effects 0.000 description 5
- MJUVQSGLWOGIOB-UHFFFAOYSA-N 2-[(Z)-hydroxyiminomethyl]-4-nonylphenol Chemical compound OC1=C(C=N/O)C=C(C=C1)CCCCCCCCC MJUVQSGLWOGIOB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000022244 formylation Effects 0.000 description 3
- NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 description 3
- 159000000003 magnesium salts Chemical class 0.000 description 3
- FPGVILQTFULZRC-UHFFFAOYSA-N magnesium;2-nonylphenol Chemical compound [Mg].CCCCCCCCCC1=CC=CC=C1O FPGVILQTFULZRC-UHFFFAOYSA-N 0.000 description 3
- SMQUZDBALVYZAC-UHFFFAOYSA-N ortho-hydroxybenzaldehyde Natural products OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 2
- CBATZAFODMYWPH-UHFFFAOYSA-N 2-(hydroxyiminomethyl)-4,6-dimethylphenol Chemical compound CC1=CC(C)=C(O)C(C=NO)=C1 CBATZAFODMYWPH-UHFFFAOYSA-N 0.000 description 2
- UFLSRRHSCGPKAE-UHFFFAOYSA-N 2-(hydroxyiminomethyl)-4-methoxyphenol Chemical compound COC1=CC=C(O)C(C=NO)=C1 UFLSRRHSCGPKAE-UHFFFAOYSA-N 0.000 description 2
- SMQUZDBALVYZAC-HOSYLAQJSA-N 2-hydroxybenzaldehyde Chemical class OC1=CC=CC=C1[13CH]=O SMQUZDBALVYZAC-HOSYLAQJSA-N 0.000 description 2
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000005248 alkyl aryloxy group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- VPTYRUGUZUYAGZ-UHFFFAOYSA-N 1-(hydroxyiminomethyl)naphthalen-2-ol Chemical compound C1=CC=C2C(C=NO)=C(O)C=CC2=C1 VPTYRUGUZUYAGZ-UHFFFAOYSA-N 0.000 description 1
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 1
- CFPNMYCFVVUHHC-UHFFFAOYSA-N 2-(hydroxyiminomethyl)-4-methylphenol Chemical compound CC1=CC=C(O)C(C=NO)=C1 CFPNMYCFVVUHHC-UHFFFAOYSA-N 0.000 description 1
- ZWJHFFKODHFICU-WEVVVXLNSA-N 2-[(E)-hydroxyiminomethyl]-6-methylphenol Chemical compound CC1=CC=CC(\C=N\O)=C1O ZWJHFFKODHFICU-WEVVVXLNSA-N 0.000 description 1
- UPYJLUZZMCGPJW-UHFFFAOYSA-N 2-butan-2-yl-6-(hydroxyiminomethyl)phenol Chemical compound CCC(C)C1=CC=CC(C=NO)=C1O UPYJLUZZMCGPJW-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- JYWIGMQDJSGOMD-UHFFFAOYSA-N 2-hydroxy-5-nonylbenzaldehyde Chemical compound CCCCCCCCCC1=CC=C(O)C(C=O)=C1 JYWIGMQDJSGOMD-UHFFFAOYSA-N 0.000 description 1
- CYEKUDPFXBLGHH-UHFFFAOYSA-N 3-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1 CYEKUDPFXBLGHH-UHFFFAOYSA-N 0.000 description 1
- KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 description 1
- FXAILOLNECSGMI-RUDMXATFSA-N 4-chloro-2-[(E)-hydroxyiminomethyl]phenol Chemical compound O\N=C\C1=C(O)C=CC(Cl)=C1 FXAILOLNECSGMI-RUDMXATFSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- UWGTVLYQSJNUFP-SILNSSARSA-N 4-dodecyl-2-[(Z)-hydroxyiminomethyl]phenol Chemical compound [H]\C(=N\O)C1=C(O)C=CC(CCCCCCCCCCCC)=C1 UWGTVLYQSJNUFP-SILNSSARSA-N 0.000 description 1
- FUKAYNNEWXTIIT-UHFFFAOYSA-N 5-tert-butyl-2-(hydroxyiminomethyl)phenol Chemical compound CC(C)(C)C1=CC=C(C=NO)C(O)=C1 FUKAYNNEWXTIIT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- FQOLHICYFDRFOM-UHFFFAOYSA-N C1=CC=CC2=C(O)C(C=NO)=CC=C21 Chemical compound C1=CC=CC2=C(O)C(C=NO)=CC=C21 FQOLHICYFDRFOM-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 206010013647 Drowning Diseases 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- OPZZWWFHZYZBRU-UHFFFAOYSA-N butanedioic acid;butane-1,1-diol Chemical compound CCCC(O)O.OC(=O)CCC(O)=O OPZZWWFHZYZBRU-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- QBRSFUSGKXVSPM-UHFFFAOYSA-N hydroxylamine;hydrobromide Chemical compound Br.ON QBRSFUSGKXVSPM-UHFFFAOYSA-N 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DPNUIZVZBWBCPB-UHFFFAOYSA-J titanium(4+);tetraphenoxide Chemical compound [Ti+4].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 DPNUIZVZBWBCPB-UHFFFAOYSA-J 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
- C07C251/46—Quinone oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
- C07C47/565—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups all hydroxy groups bound to the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9217724.5 | 1992-08-20 | ||
| GB929217724A GB9217724D0 (en) | 1992-08-20 | 1992-08-20 | Chemical process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2104068A1 CA2104068A1 (en) | 1994-02-21 |
| CA2104068C true CA2104068C (en) | 2004-10-26 |
Family
ID=10720680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002104068A Expired - Lifetime CA2104068C (en) | 1992-08-20 | 1993-08-13 | Chemical process |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US5399761A (en, 2012) |
| JP (1) | JP3536122B2 (en, 2012) |
| KR (1) | KR100287195B1 (en, 2012) |
| CN (1) | CN1036710C (en, 2012) |
| AT (1) | ATE144493T1 (en, 2012) |
| AU (1) | AU668739B2 (en, 2012) |
| CA (1) | CA2104068C (en, 2012) |
| DE (1) | DE69305599T2 (en, 2012) |
| FI (1) | FI112863B (en, 2012) |
| GB (2) | GB9217724D0 (en, 2012) |
| IN (2) | IN187887B (en, 2012) |
| PL (1) | PL174040B1 (en, 2012) |
| RU (1) | RU2124500C1 (en, 2012) |
| TW (1) | TW258728B (en, 2012) |
| ZA (1) | ZA935809B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6288276B1 (en) * | 1997-05-21 | 2001-09-11 | Henkel Kommanditgeselschaft Auf Aktien | Salicylaldoximes and method of preparation |
| US5969185A (en) * | 1997-07-14 | 1999-10-19 | Henkel Corporation | Process for making phenolic ketones |
| BR9800783A (pt) * | 1998-02-27 | 2000-05-02 | Peter Rudolf Seidl | Processo de obtenção de oximas e produtos resultantes. |
| US6673969B2 (en) * | 1998-02-27 | 2004-01-06 | Comselho Nacional De Desenvolvimento Cientifico E Tecnologico Cnpq | Process for preparation of oximes and resulting products |
| WO2001012589A1 (en) | 1999-08-12 | 2001-02-22 | Cognis Corporation | Method for separating copper from iron |
| WO2007034501A2 (en) * | 2005-09-21 | 2007-03-29 | Star Orechem International Pvt. Ltd | A novel process for the manufacture of 5-nonyl salicylaldoxime |
| CN101497576B (zh) * | 2009-03-12 | 2012-04-18 | 常州胜杰化工有限公司 | 5-壬基水杨醛肟的制备方法 |
| PL227238B1 (pl) * | 2015-03-02 | 2017-11-30 | Politechnika Warszawska | Sposób wytwarzania 5-alkilosalicylaldoksymów i zastosowanie |
| EP3121161B1 (en) | 2015-07-23 | 2018-03-07 | S.P.C.M. Sa | A method for the preparation of alkylsalicylaldehyde and alkylsalicylaldoxime, and use thereof |
| CN106966921A (zh) * | 2017-03-29 | 2017-07-21 | 江西理工大学 | 一种特辛基水杨醛肟及其合成方法 |
| GB201705330D0 (en) * | 2017-04-03 | 2017-05-17 | Johnson Matthey Plc | Platinum(II) complexes |
| CN114262282B (zh) * | 2021-12-16 | 2024-04-19 | 广东省科学院资源利用与稀土开发研究所 | 一种醛肟类化合物及其制备方法和应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU315434A1 (ru) * | 1969-12-12 | 1975-12-05 | Новокузнецкий научно-исследовательский химико-фармацевтический институт | Способ получени оксимов |
| DE2114029C3 (de) * | 1970-03-25 | 1973-11-22 | Toagosei Chemical Industry Co., Ltd., Tokio | Verfahren zur Herstellung von Oximen |
| US3808275A (en) * | 1970-03-25 | 1974-04-30 | Toa Gosei Chem Ind | Process for producing oximes |
| US4020106A (en) * | 1972-03-21 | 1977-04-26 | Imperial Chemical Industries Limited | Metal extraction process |
| GB1447114A (en) * | 1973-02-20 | 1976-08-25 | Glaxo Lab Ltd | Process for the preparation of 2-aryl-2-hydroxyiminoacetic acid |
| US4133834A (en) * | 1978-01-03 | 1979-01-09 | Allied Chemical Corporation | Process for preparing α- and β-hydroxy oximes |
| US4323706A (en) * | 1978-02-23 | 1982-04-06 | Allied Corporation | Production of acetaldehyde oxime |
| JPS54163538A (en) * | 1978-06-13 | 1979-12-26 | Sumitomo Chemical Co | Production of salycilaldehydes |
| FR2514344A1 (fr) * | 1981-10-09 | 1983-04-15 | Rhone Poulenc Spec Chim | Procede de preparation d'orthohydroxybenzaldehydes |
| US4638096A (en) * | 1982-10-12 | 1987-01-20 | Henkel Corporation | Process of preparing hydroxyarylaldehydes and catalyst therefor |
| US4507248A (en) * | 1982-11-01 | 1985-03-26 | Allied Corporation | Preparation from hydroxylammonium sulfate of oximes and hydroxamic acids via alcoholic hydroxylamine solution |
| ATE133155T1 (de) * | 1991-08-23 | 1996-02-15 | Zeneca Ltd | Herstellung von 2-hydroxyarylaldehyden |
-
1992
- 1992-08-20 GB GB929217724A patent/GB9217724D0/en active Pending
-
1993
- 1993-08-06 AT AT93306225T patent/ATE144493T1/de not_active IP Right Cessation
- 1993-08-06 DE DE69305599T patent/DE69305599T2/de not_active Expired - Lifetime
- 1993-08-06 GB GB939316310A patent/GB9316310D0/en active Pending
- 1993-08-10 IN IN856DE1993 patent/IN187887B/en unknown
- 1993-08-10 RU RU93050167A patent/RU2124500C1/ru not_active IP Right Cessation
- 1993-08-10 ZA ZA935809A patent/ZA935809B/xx unknown
- 1993-08-10 AU AU44524/93A patent/AU668739B2/en not_active Ceased
- 1993-08-11 FI FI933546A patent/FI112863B/fi not_active IP Right Cessation
- 1993-08-13 CA CA002104068A patent/CA2104068C/en not_active Expired - Lifetime
- 1993-08-16 TW TW082106571A patent/TW258728B/zh not_active IP Right Cessation
- 1993-08-19 US US08/108,424 patent/US5399761A/en not_active Expired - Lifetime
- 1993-08-19 JP JP20506193A patent/JP3536122B2/ja not_active Expired - Lifetime
- 1993-08-19 PL PL93300156A patent/PL174040B1/pl not_active IP Right Cessation
- 1993-08-20 CN CN93118264A patent/CN1036710C/zh not_active Expired - Lifetime
- 1993-08-20 KR KR1019930016200A patent/KR100287195B1/ko not_active Expired - Fee Related
- 1993-08-30 IN IN944DE1993 patent/IN187888B/en unknown
-
1995
- 1995-03-15 US US08/404,468 patent/US5502254A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU668739B2 (en) | 1996-05-16 |
| US5399761A (en) | 1995-03-21 |
| IN187888B (en, 2012) | 2002-07-13 |
| TW258728B (en, 2012) | 1995-10-01 |
| FI933546A0 (fi) | 1993-08-11 |
| DE69305599D1 (de) | 1996-11-28 |
| US5502254A (en) | 1996-03-26 |
| RU2124500C1 (ru) | 1999-01-10 |
| JPH06172290A (ja) | 1994-06-21 |
| KR100287195B1 (ko) | 2001-05-02 |
| ZA935809B (en) | 1994-07-27 |
| ATE144493T1 (de) | 1996-11-15 |
| FI112863B (fi) | 2004-01-30 |
| CN1036710C (zh) | 1997-12-17 |
| CN1099377A (zh) | 1995-03-01 |
| IN187887B (en, 2012) | 2002-07-13 |
| GB9217724D0 (en) | 1992-09-30 |
| PL174040B1 (pl) | 1998-06-30 |
| CA2104068A1 (en) | 1994-02-21 |
| AU4452493A (en) | 1994-03-03 |
| JP3536122B2 (ja) | 2004-06-07 |
| FI933546L (fi) | 1994-02-21 |
| PL300156A1 (en) | 1994-04-05 |
| KR950005801A (ko) | 1995-03-20 |
| DE69305599T2 (de) | 1997-03-13 |
| GB9316310D0 (en) | 1993-09-22 |
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|---|---|---|---|
| EEER | Examination request | ||
| MKEC | Expiry (correction) |
Effective date: 20131009 |