LU85703A1 - Procede de preparation de phenols halogenes - Google Patents
Procede de preparation de phenols halogenes Download PDFInfo
- Publication number
- LU85703A1 LU85703A1 LU85703A LU85703A LU85703A1 LU 85703 A1 LU85703 A1 LU 85703A1 LU 85703 A LU85703 A LU 85703A LU 85703 A LU85703 A LU 85703A LU 85703 A1 LU85703 A1 LU 85703A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- group
- free
- modified
- organic functional
- groups
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 51
- 230000008569 process Effects 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 16
- 150000002989 phenols Chemical class 0.000 title description 3
- 125000000524 functional group Chemical group 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 27
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 238000006277 sulfonation reaction Methods 0.000 claims description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Chemical class 0.000 claims description 15
- 238000005658 halogenation reaction Methods 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- ZZJVDYQPZOHNIK-UHFFFAOYSA-N 2,6-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(O)=C1S(O)(=O)=O ZZJVDYQPZOHNIK-UHFFFAOYSA-N 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 238000005660 chlorination reaction Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000005893 bromination reaction Methods 0.000 claims description 9
- 230000026030 halogenation Effects 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical class 0.000 claims description 6
- 230000031709 bromination Effects 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 230000002140 halogenating effect Effects 0.000 claims description 6
- 238000011065 in-situ storage Methods 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-Phenylethanol Natural products OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 230000026045 iodination Effects 0.000 claims 2
- 238000006192 iodination reaction Methods 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229940067107 phenylethyl alcohol Drugs 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 description 31
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 150000007513 acids Chemical class 0.000 description 20
- SWZVJOLLQTWFCW-UHFFFAOYSA-N 2-chlorobenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1Cl SWZVJOLLQTWFCW-UHFFFAOYSA-N 0.000 description 17
- -1 aliphatic alcohols Chemical class 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- 229960001755 resorcinol Drugs 0.000 description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
- 238000005903 acid hydrolysis reaction Methods 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 150000003460 sulfonic acids Chemical class 0.000 description 5
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 159000000011 group IA salts Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Chemical class [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- VWXVJYKCCPSYRD-UHFFFAOYSA-N 4,6-dihydroxybenzene-1,3-disulfonic acid Chemical group OC1=CC(O)=C(S(O)(=O)=O)C=C1S(O)(=O)=O VWXVJYKCCPSYRD-UHFFFAOYSA-N 0.000 description 2
- IAKDZGDUVPOFBV-UHFFFAOYSA-N 5-chloro-4,6-dihydroxybenzene-1,3-disulfonic acid Chemical compound OC1=C(Cl)C(O)=C(S(O)(=O)=O)C=C1S(O)(=O)=O IAKDZGDUVPOFBV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000006479 redox reaction Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BLIQUJLAJXRXSG-UHFFFAOYSA-N 1-benzyl-3-(trifluoromethyl)pyrrolidin-1-ium-3-carboxylate Chemical compound C1C(C(=O)O)(C(F)(F)F)CCN1CC1=CC=CC=C1 BLIQUJLAJXRXSG-UHFFFAOYSA-N 0.000 description 1
- GQTHXQVZAKGYGN-UHFFFAOYSA-N 2,4-dihydroxybenzene-1,3-disulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C(O)=C1S(O)(=O)=O GQTHXQVZAKGYGN-UHFFFAOYSA-N 0.000 description 1
- UOLPZAPIFFZLMF-UHFFFAOYSA-N 2-bromobenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1Br UOLPZAPIFFZLMF-UHFFFAOYSA-N 0.000 description 1
- BMNAUVHUXKPMOO-UHFFFAOYSA-N 3,5-dihydroxybenzene-1,2,4-trisulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=C(S(O)(=O)=O)C(O)=C1S(O)(=O)=O BMNAUVHUXKPMOO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- FNXLCIKXHOPCKH-UHFFFAOYSA-N bromamine Chemical class BrN FNXLCIKXHOPCKH-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004674 formic acids Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- XHFXMNZYIKFCPN-UHFFFAOYSA-N perchloryl fluoride Chemical compound FCl(=O)(=O)=O XHFXMNZYIKFCPN-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
- C07C35/14—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings with more than one hydroxy group bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8349556A IT1212907B (it) | 1983-12-21 | 1983-12-21 | Preparazione di fenoli alogenati |
| IT4955683 | 1983-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU85703A1 true LU85703A1 (fr) | 1985-07-24 |
Family
ID=11271015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU85703A LU85703A1 (fr) | 1983-12-21 | 1984-12-20 | Procede de preparation de phenols halogenes |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4704469A (de) |
| EP (1) | EP0146923B1 (de) |
| JP (2) | JPH0635408B2 (de) |
| KR (1) | KR880000202B1 (de) |
| AR (1) | AR240908A1 (de) |
| AT (1) | ATE65076T1 (de) |
| AU (2) | AU3711784A (de) |
| BE (1) | BE901323A (de) |
| BR (1) | BR8406649A (de) |
| CA (1) | CA1325812C (de) |
| CH (1) | CH666257A5 (de) |
| DE (1) | DE3484792D1 (de) |
| DK (1) | DK625284A (de) |
| ES (1) | ES8604845A1 (de) |
| FI (1) | FI84907C (de) |
| FR (1) | FR2557096B1 (de) |
| GR (1) | GR82532B (de) |
| HU (1) | HU196938B (de) |
| IE (1) | IE57964B1 (de) |
| IL (1) | IL73787A (de) |
| IN (1) | IN163437B (de) |
| IT (1) | IT1212907B (de) |
| LU (1) | LU85703A1 (de) |
| MX (1) | MX162546A (de) |
| NO (1) | NO164235C (de) |
| NZ (1) | NZ210605A (de) |
| PT (1) | PT79716A (de) |
| YU (1) | YU44992B (de) |
| ZA (1) | ZA849669B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5410083A (en) * | 1993-10-15 | 1995-04-25 | The Dow Chemical Company | Synthesis of diaminoresorcinal from resorcinol |
| US5371291A (en) * | 1993-10-15 | 1994-12-06 | The Dow Chemical Company | Synthesis of 4,6-diaminoresorcinol |
| US20050054586A1 (en) * | 2003-06-30 | 2005-03-10 | Bartels Stephen P. | Treatment of ophthalmic disorders |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE141751C (de) * | ||||
| FR499094A (fr) * | 1919-04-17 | 1920-01-30 | Joseph Cucumel | Machine pour le finissage des velours et tissus à poils |
| DE663552C (de) * | 1935-09-29 | 1938-08-09 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von metallhaltigen Komplexverbindungen |
| GB663552A (en) * | 1947-11-28 | 1951-12-27 | Gen Aniline & Film Corp | Process of preparing 2,4-dihydroxybenzene-sulfonic acid |
| NL94108C (de) * | 1952-06-17 | |||
| US3337549A (en) * | 1962-11-08 | 1967-08-22 | Keuffel & Esser Co | 1-[tertiary amino-carbanilido]-3, 5-dihydroxy-4-bromo benzenes |
| DE1447733B2 (de) * | 1963-12-23 | 1977-04-21 | Hoechst Ag, 6000 Frankfurt | 2-(3,5-dihydroxyphenyl)-benzimidazolderivate |
| FR1545111A (fr) * | 1966-11-22 | 1968-11-08 | Gen Aniline & Film Corp | Procédé perfectionné de préparation d'acide 3-benzoly-4-hydroxy-6-méthoxybenzènesulfonique et produit obtenu par ce procédé |
| DE1643400C3 (de) * | 1966-11-22 | 1980-09-25 | Basf Wyandotte Corp., Wyandotte, Mich. (V.St.A.) | Verwendung von 3-Benzoyl-4-hydroxy-6-methoxybenzolsulfonsäure als ultraviolett-Hchtabsorbierendes Mittel |
| US3919322A (en) * | 1969-01-22 | 1975-11-11 | Hoffmann La Roche | 3-Substituted -5-alkyl-2-cyclohexen-1-ones |
| US3770547A (en) * | 1971-05-14 | 1973-11-06 | Sloane Mfg Co R & G | Color bond surveillance system |
| US3790636A (en) * | 1971-09-16 | 1974-02-05 | Hoffmann La Roche | Process for the preparation of alkyl substituted resorcinols |
| US3713256A (en) * | 1971-10-28 | 1973-01-30 | Besenbruch Hofmann | Adjustable grinding tool for brake cylinders and the like |
| JPS5644413B2 (de) * | 1973-05-12 | 1981-10-19 | ||
| CH605827A5 (en) * | 1973-11-08 | 1978-10-13 | Hoffmann La Roche | 2,4-diamino-5-(3,5-dialkoxy-4-halo-benzyl)-pyrimidines |
| DK136470B (da) * | 1973-11-08 | 1977-10-17 | Hoffmann La Roche | Analogifremgangsmåde til fremstilling af 2,4-diamino-5-benzylpyrimidinderivater eller salte deraf. |
| DE2616479C2 (de) * | 1976-04-14 | 1986-12-04 | Brickl, Rolf, Dr., 7951 Warthausen | Substituierte Fluoracylresorcine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel und Kosmetika |
| IT1088554B (it) * | 1977-11-17 | 1985-06-10 | F I D I A Spa | Procedimento sellettivo per la preparazione di derivati della 7-indrossi cumarina |
| JPS555721A (en) * | 1978-06-27 | 1980-01-16 | Kawasaki Steel Corp | Detecting method for clogging of nozzle |
| DE3071196D1 (en) * | 1979-08-03 | 1985-11-28 | Toshiba Kk | Device for performing a heat-sensitive recording, heat-sensitive recording sheet, and a method for performing a heat-sensitive recording |
| JPS5644413A (en) * | 1979-09-18 | 1981-04-23 | Honda Motor Co Ltd | Device for introducing secondary air in engine |
| DD147424A1 (de) * | 1979-11-28 | 1981-04-01 | Detlef Rehorek | Ein-oder zweikomponentendiazotypiematerial |
| JPS56111849A (en) * | 1980-02-12 | 1981-09-03 | Konishiroku Photo Ind Co Ltd | Silver halide photographic sensitive material |
| DE3016905A1 (de) * | 1980-05-02 | 1981-11-05 | Henkel KGaA, 4000 Düsseldorf | Haarfaerbemittel |
| DE3044128A1 (de) * | 1980-11-24 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Cumarine, verfahren zu ihrer herstellung und ihre verwendung |
| JPS5934530A (ja) * | 1982-08-23 | 1984-02-24 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
-
1983
- 1983-12-21 IT IT8349556A patent/IT1212907B/it active
-
1984
- 1984-12-11 IL IL73787A patent/IL73787A/xx unknown
- 1984-12-11 IN IN863/CAL/84A patent/IN163437B/en unknown
- 1984-12-12 ES ES538544A patent/ES8604845A1/es not_active Expired
- 1984-12-12 ZA ZA849669A patent/ZA849669B/xx unknown
- 1984-12-14 MX MX203758A patent/MX162546A/es unknown
- 1984-12-18 NZ NZ210605A patent/NZ210605A/xx unknown
- 1984-12-18 FR FR8419343A patent/FR2557096B1/fr not_active Expired
- 1984-12-19 AT AT84115842T patent/ATE65076T1/de active
- 1984-12-19 EP EP84115842A patent/EP0146923B1/de not_active Expired - Lifetime
- 1984-12-19 KR KR1019840008110A patent/KR880000202B1/ko not_active Expired
- 1984-12-19 CA CA000470581A patent/CA1325812C/en not_active Expired - Fee Related
- 1984-12-19 FI FI845035A patent/FI84907C/fi not_active IP Right Cessation
- 1984-12-19 DE DE8484115842T patent/DE3484792D1/de not_active Expired - Lifetime
- 1984-12-20 GR GR82532A patent/GR82532B/el unknown
- 1984-12-20 BE BE1/11161A patent/BE901323A/fr not_active IP Right Cessation
- 1984-12-20 JP JP59270575A patent/JPH0635408B2/ja not_active Expired - Lifetime
- 1984-12-20 NO NO845150A patent/NO164235C/no unknown
- 1984-12-20 IE IE3276/84A patent/IE57964B1/en not_active IP Right Cessation
- 1984-12-20 PT PT79716A patent/PT79716A/pt not_active IP Right Cessation
- 1984-12-20 AU AU37117/84A patent/AU3711784A/en not_active Abandoned
- 1984-12-20 BR BR8406649A patent/BR8406649A/pt not_active IP Right Cessation
- 1984-12-20 HU HU844755A patent/HU196938B/hu not_active IP Right Cessation
- 1984-12-20 CH CH6084/84A patent/CH666257A5/fr not_active IP Right Cessation
- 1984-12-20 LU LU85703A patent/LU85703A1/fr unknown
- 1984-12-21 AR AR299067A patent/AR240908A1/es active
- 1984-12-21 DK DK625284A patent/DK625284A/da not_active Application Discontinuation
- 1984-12-21 US US06/684,733 patent/US4704469A/en not_active Expired - Lifetime
- 1984-12-21 YU YU2183/84A patent/YU44992B/xx unknown
-
1989
- 1989-07-06 AU AU37925/89A patent/AU618819B2/en not_active Ceased
-
1992
- 1992-11-18 JP JP4308634A patent/JPH0788349B2/ja not_active Ceased
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0377381A1 (de) | Verfahren zur Herstellung von 1-Phenyl-2-diethyl-aminocarbonyl-2-phthalimidomethyl-cyclopropan Z | |
| FR2529886A1 (fr) | Procede de preparation d'arylalcanoates a partir de 1-halogenalkylarylcetals catalyses par des carboxylates de zinc | |
| EP0149407A2 (de) | Verfahren zur Herstellung von Brombenzaldehyden-Hydroxy und/oder Alkoxy substituiert | |
| EP2170801B1 (de) | Neues verfahren zur synthese von fenofibrat | |
| EP0149952B1 (de) | Verfahren zur Herstellung von Brombenzaldehyden-Hydroxy und/oder Alkoxy substituiert | |
| LU85703A1 (fr) | Procede de preparation de phenols halogenes | |
| FR2601005A1 (fr) | Procede de preparation d'esters alkyliques de l'acide cyano-2 tetrachlorobenzoique | |
| EP0200840B1 (de) | Verfahren zur Herstellung von gegebenenfalls in 5-Stellung halogenisierten 6-(Nieder)-alkoxy-1-naphthoesäuren und den entsprechenden Estern | |
| CH642614A5 (fr) | Procede de preparation d'acides trichlorophenoxyalcanoiques et de leurs derives exempts de dibenzo-p-dioxines chlorees. | |
| WO2004007424A1 (fr) | Procede de preparation d'un nitrophenol | |
| EP0072293B1 (de) | Verfahren zur Herstellung von Ursodeoxy-Cholsäure ausgehend von 3-alpha, 7-beta, 12-alpha-trihydroxy-Cholsäure und verwendete Zwischenprodukte | |
| EP0278822B1 (de) | Verfahren zur Herstellung von Perhalogenalkansulfin- und -sulfonsäureabkömmlingen | |
| CH648329A5 (fr) | Procede de preparation de steroides. | |
| EP0195171B1 (de) | Verfahren zur Herstellung von Monochlorhydrochinonen | |
| FR2540860A1 (fr) | Nouveaux intermediaires pour la production de derives de l'acide 2-(2-aminothiazol-4-yl) glyoxylique ou d'un de ses sels et le procede de production desdits intermediaires | |
| FR2550190A1 (fr) | Procede de preparation de b-phenylserine | |
| WO2011098985A1 (fr) | Procede de preparation de composes adamantyles | |
| EP1468993A1 (de) | Verfahren zur Herstellung von Hexahydropyridazin-3-carbonsäure-Derivaten | |
| EP0059659B1 (de) | Derivate der 4-Methyl-3-formyl-pentansäure, ihr Herstellungsverfahren und Anwendung zur Herstellung von cyclischen Derivaten | |
| EP0037352A1 (de) | Verfahren zur Herstellung chlorierter Benzoxazolonderivate | |
| CA1111447A (fr) | Composes halogenes, procede de preparation et application a la preparation du metaphenoxy benzaldehyde | |
| EP0860443A1 (de) | Industrialisierungsverfahren zur Herstellung von Diosmin aus Hesperidin | |
| EP0495952A1 (de) | Verfahren zur herstellung von 2-nitrobenzaldehyd- und nitrobenzoesäurederivate | |
| EP0767162A1 (de) | Natrium-Orthohydroxymandelat-Phenol-Wasser-Komplexe, Verfahren zu deren Herstellung sowie Verwendung zur Isolation des Natrium Orthohydroxymandelats | |
| FR2573754A1 (fr) | Procede de preparation d'acides a-hydroxyphenylalcanoiques et composes obtenus par ce procede |