NO784070L - Fremgangsmaate ved fremstilling av klorert fenol - Google Patents
Fremgangsmaate ved fremstilling av klorert fenolInfo
- Publication number
- NO784070L NO784070L NO784070A NO784070A NO784070L NO 784070 L NO784070 L NO 784070L NO 784070 A NO784070 A NO 784070A NO 784070 A NO784070 A NO 784070A NO 784070 L NO784070 L NO 784070L
- Authority
- NO
- Norway
- Prior art keywords
- reaction
- reaction medium
- dichlorophenol
- trichlorophenol
- catalyst
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title 1
- 239000012429 reaction media Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 17
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 claims description 15
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 claims description 13
- 239000011968 lewis acid catalyst Substances 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 238000005660 chlorination reaction Methods 0.000 claims description 7
- XGCHAIDDPMFRLJ-UHFFFAOYSA-N 2,3,6-trichlorophenol Chemical compound OC1=C(Cl)C=CC(Cl)=C1Cl XGCHAIDDPMFRLJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000012430 organic reaction media Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 239000006227 byproduct Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 3
- JHBKHLUZVFWLAG-UHFFFAOYSA-N 1,2,4,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C=C1Cl JHBKHLUZVFWLAG-UHFFFAOYSA-N 0.000 claims 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims 1
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 claims 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims 1
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 claims 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 claims 1
- VBZBVAZQSYTWLB-UHFFFAOYSA-N 3-benzyl-3,4,4,5,5,6-hexachlorocyclohexene Chemical compound ClC1C(C(C(C=C1)(CC1=CC=CC=C1)Cl)(Cl)Cl)(Cl)Cl VBZBVAZQSYTWLB-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000003899 bactericide agent Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims 1
- 229940106681 chloroacetic acid Drugs 0.000 claims 1
- 239000002537 cosmetic Substances 0.000 claims 1
- 238000006193 diazotization reaction Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 claims 1
- 229960004068 hexachlorophene Drugs 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical group [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000000344 soap Substances 0.000 claims 1
- 239000001119 stannous chloride Substances 0.000 claims 1
- 235000011150 stannous chloride Nutrition 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 claims 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 230000007306 turnover Effects 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5077377 | 1977-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO784070L true NO784070L (no) | 1979-06-07 |
Family
ID=10457294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO784070A NO784070L (no) | 1977-12-06 | 1978-12-04 | Fremgangsmaate ved fremstilling av klorert fenol |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4237321A (de) |
| EP (1) | EP0002373A1 (de) |
| AT (1) | AT360507B (de) |
| DK (1) | DK548478A (de) |
| FI (1) | FI783731A7 (de) |
| NO (1) | NO784070L (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4346248A (en) * | 1980-02-20 | 1982-08-24 | Vertac Chemical Corporation | Preparation of 2,4,5-trichlorophenol and 2,4,5-trichlorophenoxyacetic acid free of 2,3,7,8-tetrachloro-dibenzo-p-dioxin contamination |
| DE3132692A1 (de) * | 1981-08-19 | 1983-03-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur halogenierung von organischen verbindungen |
| US4564714A (en) * | 1984-10-30 | 1986-01-14 | Givaudan Corporation | Process for the preparation of 2,4,5-trichlorophenol under acidic conditions |
| FR2587332B1 (fr) * | 1985-09-19 | 1989-02-17 | Rhone Poulenc Spec Chim | Procede de chloration selective de composes phenoliques |
| FR2601001B1 (fr) * | 1986-07-02 | 1988-11-10 | Rhone Poulenc Chim Base | Procede de chloration de composes phenoliques |
| FR2611702B1 (fr) * | 1987-03-05 | 1989-06-09 | Rhone Poulenc Chimie | Procede de chloration de l'orthochlorophenol |
| FR2611701B1 (fr) * | 1987-03-05 | 1989-06-16 | Rhone Poulenc Chimie | Procede de chloration de composes phenoliques |
| FR2618144B1 (fr) * | 1987-07-17 | 1989-11-24 | Rhone Poulenc Chimie | Procede de chloration de composes phenoliques |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE527393C (de) * | 1929-06-09 | 1931-06-19 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von chlorierten Phenolen |
| US2494993A (en) * | 1943-04-21 | 1950-01-17 | Ici Ltd | Manufacture of chlorocresols |
| US2665314A (en) * | 1951-04-04 | 1954-01-05 | Du Pont | Selective chlorination of 2, 5-dichlorophenal to 2, 4, 5-trichlorophenol in the presence of 2, 4-dichlorophenal |
| US2756260A (en) * | 1952-08-14 | 1956-07-24 | Dow Chemical Co | Method of making trichlorophenol mixtures which are rich in the 2, 4, 5-isomer |
| NL274287A (de) * | 1961-02-03 |
-
1978
- 1978-12-01 EP EP78300722A patent/EP0002373A1/de not_active Withdrawn
- 1978-12-04 NO NO784070A patent/NO784070L/no unknown
- 1978-12-04 DK DK548478A patent/DK548478A/da unknown
- 1978-12-04 US US05/966,101 patent/US4237321A/en not_active Expired - Lifetime
- 1978-12-05 AT AT869278A patent/AT360507B/de not_active IP Right Cessation
- 1978-12-05 FI FI783731A patent/FI783731A7/fi unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT360507B (de) | 1981-01-12 |
| EP0002373A1 (de) | 1979-06-13 |
| ATA869278A (de) | 1980-06-15 |
| FI783731A7 (fi) | 1979-06-07 |
| DK548478A (da) | 1979-06-07 |
| US4237321A (en) | 1980-12-02 |
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