FR2640966A1 - Process for the preparation of pentachlorophenol - Google Patents
Process for the preparation of pentachlorophenol Download PDFInfo
- Publication number
- FR2640966A1 FR2640966A1 FR8817380A FR8817380A FR2640966A1 FR 2640966 A1 FR2640966 A1 FR 2640966A1 FR 8817380 A FR8817380 A FR 8817380A FR 8817380 A FR8817380 A FR 8817380A FR 2640966 A1 FR2640966 A1 FR 2640966A1
- Authority
- FR
- France
- Prior art keywords
- phenol
- gallium
- pentachlorophenol
- chlorination
- dichloro
- 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.)
- Granted
Links
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 18
- 229910052733 gallium Inorganic materials 0.000 claims abstract description 15
- -1 gallium halide Chemical class 0.000 claims abstract description 12
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical class OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 claims abstract description 11
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical class OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 claims abstract description 7
- KEWNKZNZRIAIAK-UHFFFAOYSA-N 2,3,5,6-tetrachlorophenol Chemical class OC1=C(Cl)C(Cl)=CC(Cl)=C1Cl KEWNKZNZRIAIAK-UHFFFAOYSA-N 0.000 claims abstract description 6
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical class OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 claims description 15
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical group Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 claims description 5
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 claims description 4
- OEPYKQWKPYWOJU-UHFFFAOYSA-N 4,4,6-trichlorocyclohexa-1,5-dien-1-ol Chemical compound OC1=CCC(Cl)(Cl)C=C1Cl OEPYKQWKPYWOJU-UHFFFAOYSA-N 0.000 claims description 4
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- DWRNSCDYNYYYHT-UHFFFAOYSA-K gallium(iii) iodide Chemical compound I[Ga](I)I DWRNSCDYNYYYHT-UHFFFAOYSA-K 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 230000004927 fusion Effects 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 18
- 239000000460 chlorine Substances 0.000 abstract description 18
- 229910052801 chlorine Inorganic materials 0.000 abstract description 18
- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 abstract description 15
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 230000000855 fungicidal effect Effects 0.000 abstract description 2
- 239000000417 fungicide Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910005267 GaCl3 Inorganic materials 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- NLBQVWJHLWAFGJ-UHFFFAOYSA-N 1,2,3,4,6,7-hexachlorodibenzo-p-dioxin Chemical compound ClC1=C(Cl)C(Cl)=C2OC3=C(Cl)C(Cl)=CC=C3OC2=C1Cl NLBQVWJHLWAFGJ-UHFFFAOYSA-N 0.000 description 1
- SQYPHURZDDGYGF-UHFFFAOYSA-N 2,4,4-trichlorocyclohexa-1,5-dien-1-ol Chemical compound OC1=C(Cl)CC(Cl)(Cl)C=C1 SQYPHURZDDGYGF-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 150000002013 dioxins Chemical class 0.000 description 1
- SRVXDMYFQIODQI-UHFFFAOYSA-K gallium(iii) bromide Chemical compound Br[Ga](Br)Br SRVXDMYFQIODQI-UHFFFAOYSA-K 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 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
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003171 wood protecting agent Substances 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)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8817380A FR2640966A1 (en) | 1988-12-23 | 1988-12-23 | Process for the preparation of pentachlorophenol |
| GB8928880A GB2226314A (en) | 1988-12-23 | 1989-12-21 | Preparation of pentachlorophenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8817380A FR2640966A1 (en) | 1988-12-23 | 1988-12-23 | Process for the preparation of pentachlorophenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2640966A1 true FR2640966A1 (en) | 1990-06-29 |
| FR2640966B1 FR2640966B1 (enrdf_load_stackoverflow) | 1991-04-12 |
Family
ID=9373563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8817380A Granted FR2640966A1 (en) | 1988-12-23 | 1988-12-23 | Process for the preparation of pentachlorophenol |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2640966A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2226314A (enrdf_load_stackoverflow) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0262063A2 (fr) * | 1986-09-25 | 1988-03-30 | Rhone-Poulenc Chimie | procédé de stabilisation des mélanges de chloration du phénol et/ou de chlorophénols |
-
1988
- 1988-12-23 FR FR8817380A patent/FR2640966A1/fr active Granted
-
1989
- 1989-12-21 GB GB8928880A patent/GB2226314A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0262063A2 (fr) * | 1986-09-25 | 1988-03-30 | Rhone-Poulenc Chimie | procédé de stabilisation des mélanges de chloration du phénol et/ou de chlorophénols |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2226314A (en) | 1990-06-27 |
| GB8928880D0 (en) | 1990-02-28 |
| FR2640966B1 (enrdf_load_stackoverflow) | 1991-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |