BR112017006338B1 - Processos para produção de 2,5-diclorofenol e de ácido 3,6-dicloro-2-metoxibenzóico - Google Patents
Processos para produção de 2,5-diclorofenol e de ácido 3,6-dicloro-2-metoxibenzóico Download PDFInfo
- Publication number
- BR112017006338B1 BR112017006338B1 BR112017006338-7A BR112017006338A BR112017006338B1 BR 112017006338 B1 BR112017006338 B1 BR 112017006338B1 BR 112017006338 A BR112017006338 A BR 112017006338A BR 112017006338 B1 BR112017006338 B1 BR 112017006338B1
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- BR
- Brazil
- Prior art keywords
- dichlorophenol
- modality
- catalyst
- zeolite catalyst
- zeolite
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 490
- 230000008569 process Effects 0.000 title claims abstract description 461
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 title claims abstract description 191
- 239000002253 acid Substances 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 470
- 239000010457 zeolite Substances 0.000 claims abstract description 434
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 412
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 401
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 claims abstract description 275
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims abstract description 50
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims abstract description 23
- 230000000640 hydroxylating effect Effects 0.000 claims abstract description 6
- 238000006317 isomerization reaction Methods 0.000 claims description 198
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 162
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 90
- 239000011148 porous material Substances 0.000 claims description 89
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 81
- 229910052681 coesite Inorganic materials 0.000 claims description 81
- 229910052906 cristobalite Inorganic materials 0.000 claims description 81
- 239000000377 silicon dioxide Substances 0.000 claims description 81
- 235000012239 silicon dioxide Nutrition 0.000 claims description 81
- 229910052682 stishovite Inorganic materials 0.000 claims description 81
- 229910052905 tridymite Inorganic materials 0.000 claims description 81
- 229910052593 corundum Inorganic materials 0.000 claims description 80
- 229910001845 yogo sapphire Inorganic materials 0.000 claims description 80
- 238000005805 hydroxylation reaction Methods 0.000 claims description 66
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 claims description 57
- 230000033444 hydroxylation Effects 0.000 claims description 39
- 230000036961 partial effect Effects 0.000 claims description 38
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 32
- 239000007795 chemical reaction product Substances 0.000 claims description 29
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
- 239000007800 oxidant agent Substances 0.000 claims description 18
- 229910052742 iron Inorganic materials 0.000 claims description 10
- FKIKPQHMWFZFEB-UHFFFAOYSA-N 3,6-dichloro-2-hydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C(Cl)=CC=C1Cl FKIKPQHMWFZFEB-UHFFFAOYSA-N 0.000 claims description 7
- 239000002002 slurry Substances 0.000 claims description 4
- 230000001035 methylating effect Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 99
- 229910052799 carbon Inorganic materials 0.000 description 61
- 239000007789 gas Substances 0.000 description 59
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 34
- 238000002474 experimental method Methods 0.000 description 30
- 230000001965 increasing effect Effects 0.000 description 29
- 239000000203 mixture Substances 0.000 description 27
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 23
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 23
- 229910052782 aluminium Inorganic materials 0.000 description 23
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 22
- 230000000694 effects Effects 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 150000002989 phenols Chemical class 0.000 description 20
- 229910000323 aluminium silicate Inorganic materials 0.000 description 18
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 15
- 230000003716 rejuvenation Effects 0.000 description 15
- 230000004913 activation Effects 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 230000003247 decreasing effect Effects 0.000 description 12
- 238000011068 loading method Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 230000002378 acidificating effect Effects 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical class OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 238000001354 calcination Methods 0.000 description 8
- 239000012013 faujasite Substances 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 150000001555 benzenes Chemical class 0.000 description 7
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 7
- 230000000737 periodic effect Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- CFRNXBBHKHHBQM-UHFFFAOYSA-N titanium(4+);silicate Chemical class [Ti+4].[O-][Si]([O-])([O-])[O-] CFRNXBBHKHHBQM-UHFFFAOYSA-N 0.000 description 7
- 239000005504 Dicamba Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000001172 regenerating effect Effects 0.000 description 6
- 230000008929 regeneration Effects 0.000 description 6
- 238000011069 regeneration method Methods 0.000 description 6
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 description 5
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- 238000006298 dechlorination reaction Methods 0.000 description 5
- 229910052733 gallium Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 230000001186 cumulative effect Effects 0.000 description 4
- 230000009849 deactivation Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000001272 nitrous oxide Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 241000894007 species Species 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- -1 titanium silicates Chemical class 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- CGKXWKPNOMQLLK-UHFFFAOYSA-N 2,4-dichlorophenol;2,5-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl.OC1=CC(Cl)=CC=C1Cl CGKXWKPNOMQLLK-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 2
- 229910002800 Si–O–Al Inorganic materials 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 230000002860 competitive effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
- UYCAHJVVSUZSBJ-UHFFFAOYSA-N 1,2-dichlorobenzene;1,3-dichlorobenzene;1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1.ClC1=CC=CC(Cl)=C1.ClC1=CC=CC=C1Cl UYCAHJVVSUZSBJ-UHFFFAOYSA-N 0.000 description 1
- OOYZEVHHFLKRQS-UHFFFAOYSA-N 2,3-dichlorophenol;2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl.OC1=CC=CC(Cl)=C1Cl OOYZEVHHFLKRQS-UHFFFAOYSA-N 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000008380 degradant Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000003837 high-temperature calcination Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(III) nitrate Inorganic materials [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013020 steam cleaning Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/88—Use of additives, e.g. for stabilisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/633—Pore volume less than 0.5 ml/g
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/64—Pore diameter
- B01J35/643—Pore diameter less than 2 nm
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/64—Pore diameter
- B01J35/647—2-50 nm
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/64—Pore diameter
- B01J35/651—50-500 nm
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/26—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms
- C07C39/27—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms all halogen atoms being bound to ring carbon atoms
- C07C39/30—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms all halogen atoms being bound to ring carbon atoms the halogen being two chlorine atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nanotechnology (AREA)
- Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462058886P | 2014-10-02 | 2014-10-02 | |
| US62/058,886 | 2014-10-02 | ||
| US201462091995P | 2014-12-15 | 2014-12-15 | |
| US62/091,995 | 2014-12-15 | ||
| PCT/US2015/053715 WO2016054506A1 (en) | 2014-10-02 | 2015-10-02 | Processes for preparing 2,5-dichlorophenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112017006338A2 BR112017006338A2 (pt) | 2017-12-19 |
| BR112017006338B1 true BR112017006338B1 (pt) | 2021-11-16 |
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| BR112017006338-7A BR112017006338B1 (pt) | 2014-10-02 | 2015-10-02 | Processos para produção de 2,5-diclorofenol e de ácido 3,6-dicloro-2-metoxibenzóico |
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| Country | Link |
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| US (2) | US10550063B2 (https=) |
| EP (1) | EP3201164B1 (https=) |
| JP (1) | JP6752783B2 (https=) |
| KR (1) | KR102615452B1 (https=) |
| CN (2) | CN113801001A (https=) |
| BR (1) | BR112017006338B1 (https=) |
| WO (1) | WO2016054506A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11065611B2 (en) * | 2016-10-05 | 2021-07-20 | Monsanto Technology Llc | Emission control during catalyst regeneration |
| CN113160901B (zh) * | 2021-03-24 | 2023-01-03 | 柳州东风容泰化工股份有限公司 | 一种提高氯代苯酚合成率的方法及装置 |
| EP4166531A1 (en) * | 2021-10-12 | 2023-04-19 | Studiengesellschaft Kohle mbH | Process for preparing a phenolic hydrocarbon |
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| US2480817A (en) | 1947-06-17 | 1949-08-30 | Us Rubber Co | Preparation of polychlorophenoxyacetic acids useful as plant growth regulators |
| US2651659A (en) | 1952-01-31 | 1953-09-08 | Us Rubber Co | Preparation of 2, 4-dichlorophenoxyacetic acid |
| US2708209A (en) | 1953-10-29 | 1955-05-10 | Olin Mathieson | Process for selective crystallization of 2, 5-dichlorophenol |
| US3013054A (en) | 1958-08-04 | 1961-12-12 | Velsicol Chemical Corp | 2-methoxy-3, 6-dichlorobenzoates |
| DE1493493A1 (de) | 1965-09-10 | 1969-02-20 | Boehringer Sohn Ingelheim | Verfahren zur Gewinnung von 2,5-Dichlorphenol aus einem Isomerengemisch von 2,4- und 2,5-Dichlorphenol |
| GB1221019A (en) | 1968-02-09 | 1971-02-03 | Coalite Chem Prod Ltd | Process for the production of dihalophenols |
| US4418235A (en) * | 1980-02-14 | 1983-11-29 | Mobil Oil Corporation | Hydrocarbon conversion with zeolite having enhanced catalytic activity |
| US4326994A (en) * | 1980-02-14 | 1982-04-27 | Mobil Oil Corporation | Enhancement of zeolite catalytic activity |
| JPS58144330A (ja) * | 1982-02-24 | 1983-08-27 | Toray Ind Inc | ポリハロゲン化芳香族化合物の異性化方法 |
| EP0144760B1 (de) * | 1983-11-12 | 1989-01-04 | Hoechst Aktiengesellschaft | Verfahren zur Isomerisierung von Mono- oder Dichlorophenolen |
| DE3340997A1 (de) * | 1983-11-12 | 1985-05-23 | Hoechst Ag, 6230 Frankfurt | Verfahren zur isomerisierung von chlorphenolen |
| JP2725179B2 (ja) * | 1988-04-21 | 1998-03-09 | 日本カーバイド工業株式会社 | ２，４，５−トリフルオロー３−ヒドロキシ安息香酸の製造方法 |
| US5118876A (en) | 1989-01-18 | 1992-06-02 | Zinnen Hermann A | Separation of dichlorophenol isomers with zeolite adsorbents |
| FR2648810B1 (fr) | 1989-06-22 | 1992-02-28 | Rhone Poulenc Chimie | Procede de preparation de phenols |
| US5110995A (en) | 1991-03-12 | 1992-05-05 | Institute Of Catalysis | Preparation of phenol or phenol derivatives |
| RU2058286C1 (ru) | 1994-04-12 | 1996-04-20 | Институт катализа им.Г.К.Борескова СО РАН | Способ получения фенола или его производных |
| RU2074164C1 (ru) | 1994-04-12 | 1997-02-27 | Институт катализа им.Г.К.Борескова СО РАН | Способ получения фенола или его производных |
| US5648562A (en) * | 1994-08-03 | 1997-07-15 | Sandoz Ltd. | Oxidation process |
| US6323377B1 (en) | 1995-06-07 | 2001-11-27 | Syngenta Participations Ag | Oxidation process |
| US6586624B1 (en) | 1995-12-12 | 2003-07-01 | Syngenta Participations Ag | Oxidation process |
| US6274776B1 (en) | 1995-12-12 | 2001-08-14 | Syngenta Participations | Oxidation process |
| JP3684265B2 (ja) * | 1996-03-26 | 2005-08-17 | 触媒化成工業株式会社 | 均一なミクロポアと均一なメソポアの２種類の細孔を有するフォージャサイト型ゼオライトおよびその製造方法 |
| US6156938A (en) | 1997-04-03 | 2000-12-05 | Solutia, Inc. | Process for making phenol or phenol derivatives |
| AU2387597A (en) | 1997-04-17 | 1998-11-13 | Novartis Ag | Process for the hydroxylation of 1,4-dichlorobenzene |
| RU2127721C1 (ru) | 1997-07-29 | 1999-03-20 | Институт органической химии им.Зелинского РАН | Способ получения фенола и его производных |
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| DE10036953A1 (de) | 2000-07-28 | 2002-02-07 | Bayer Ag | Verfahren zur Herstellung von Hydroxyaromaten |
| RU2192308C1 (ru) | 2001-02-19 | 2002-11-10 | Институт катализа им. Г.К.Борескова СО РАН | Способ активации цеолитных катализаторов для процесса окислительного гидроксилирования ароматических соединений |
| DE10112396A1 (de) | 2001-03-13 | 2002-10-02 | Krupp Uhde Gmbh | Verfahren zur Verringerung des N¶2¶O-Gehalts in Gasen und ausgewählte Katalysatoren |
| US8361434B2 (en) * | 2008-09-18 | 2013-01-29 | Exxonmobil Research And Engineering Company | Extra mesoporous Y zeolite |
| CN102125035B (zh) * | 2010-12-13 | 2013-07-31 | 上海力智生化科技有限公司 | 一种除草剂麦草畏的制备工艺 |
| US20160017238A1 (en) * | 2012-02-17 | 2016-01-21 | Kior, Inc. | Mesoporous Zeolite-Containing Catalysts For The Thermoconversion Of Biomass And For Upgrading Bio-Oils |
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2015
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- 2015-10-02 CN CN202111195305.9A patent/CN113801001A/zh active Pending
- 2015-10-02 CN CN201580065029.0A patent/CN107001211B/zh active Active
- 2015-10-02 US US15/516,105 patent/US10550063B2/en active Active
- 2015-10-02 KR KR1020177011983A patent/KR102615452B1/ko active Active
- 2015-10-02 EP EP15845685.5A patent/EP3201164B1/en active Active
- 2015-10-02 JP JP2017517663A patent/JP6752783B2/ja active Active
- 2015-10-02 BR BR112017006338-7A patent/BR112017006338B1/pt active IP Right Grant
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Also Published As
| Publication number | Publication date |
|---|---|
| CN113801001A (zh) | 2021-12-17 |
| CN107001211B (zh) | 2021-10-29 |
| US20200216379A1 (en) | 2020-07-09 |
| US10550063B2 (en) | 2020-02-04 |
| JP6752783B2 (ja) | 2020-09-09 |
| KR102615452B1 (ko) | 2023-12-19 |
| BR112017006338A2 (pt) | 2017-12-19 |
| EP3201164B1 (en) | 2020-11-25 |
| EP3201164A4 (en) | 2018-06-06 |
| WO2016054506A1 (en) | 2016-04-07 |
| KR20170063923A (ko) | 2017-06-08 |
| CN107001211A (zh) | 2017-08-01 |
| EP3201164A1 (en) | 2017-08-09 |
| JP2017530150A (ja) | 2017-10-12 |
| US20170247310A1 (en) | 2017-08-31 |
| US11008276B2 (en) | 2021-05-18 |
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