DE2117690A1 - Verfahren zur Herstellung von Phenoxyphenolen bzw. Chlorphenoxyphenolen - Google Patents
Verfahren zur Herstellung von Phenoxyphenolen bzw. ChlorphenoxyphenolenInfo
- Publication number
- DE2117690A1 DE2117690A1 DE19712117690 DE2117690A DE2117690A1 DE 2117690 A1 DE2117690 A1 DE 2117690A1 DE 19712117690 DE19712117690 DE 19712117690 DE 2117690 A DE2117690 A DE 2117690A DE 2117690 A1 DE2117690 A1 DE 2117690A1
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- chlorophenol
- reaction
- alkali
- phenoxyphenols
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- KDTZBYPBMTXCSO-UHFFFAOYSA-N 2-phenoxyphenol Chemical class OC1=CC=CC=C1OC1=CC=CC=C1 KDTZBYPBMTXCSO-UHFFFAOYSA-N 0.000 title claims description 7
- FCPHOVHDDYCNCK-UHFFFAOYSA-N 3-chloro-2-phenoxyphenol Chemical class OC1=CC=CC(Cl)=C1OC1=CC=CC=C1 FCPHOVHDDYCNCK-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 25
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 claims description 17
- 239000003513 alkali Substances 0.000 claims description 14
- 239000010949 copper Substances 0.000 claims description 10
- 150000002989 phenols Chemical class 0.000 claims description 10
- -1 chlorophenol ethers Chemical class 0.000 claims description 9
- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 4
- 239000005749 Copper compound Substances 0.000 claims description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001880 copper compounds Chemical class 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 claims description 2
- 229960001867 guaiacol Drugs 0.000 claims description 2
- 150000008379 phenol ethers Chemical class 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 230000035484 reaction time Effects 0.000 description 15
- 235000011118 potassium hydroxide Nutrition 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- JMSKYMHFNWGUJG-UHFFFAOYSA-N 1-bromo-2-(2-bromophenoxy)benzene Chemical compound BrC1=CC=CC=C1OC1=CC=CC=C1Br JMSKYMHFNWGUJG-UHFFFAOYSA-N 0.000 description 1
- MFJMZOUFSWSBNV-UHFFFAOYSA-N 1-chloro-2-(2-chlorophenoxy)benzene Chemical compound ClC1=CC=CC=C1OC1=CC=CC=C1Cl MFJMZOUFSWSBNV-UHFFFAOYSA-N 0.000 description 1
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical class OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- PLXMSFGJWZAQTH-UHFFFAOYSA-N 2-(2-chlorophenoxy)phenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1Cl PLXMSFGJWZAQTH-UHFFFAOYSA-N 0.000 description 1
- YBCSVIZLTRILNU-UHFFFAOYSA-N 2-(2-propan-2-ylphenoxy)phenol Chemical compound CC(C)C1=CC=CC=C1OC1=CC=CC=C1O YBCSVIZLTRILNU-UHFFFAOYSA-N 0.000 description 1
- LRADVKQALJANQG-UHFFFAOYSA-N 2-chlorophenol;sodium Chemical compound [Na].OC1=CC=CC=C1Cl LRADVKQALJANQG-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- ZORRXTMYEMLDRT-UHFFFAOYSA-N 4-chloro-2,3-diphenoxyphenol Chemical compound ClC1=C(C(=C(C=C1)O)OC1=CC=CC=C1)OC1=CC=CC=C1 ZORRXTMYEMLDRT-UHFFFAOYSA-N 0.000 description 1
- MXJBIALFHGDUPE-UHFFFAOYSA-N 4-chlorophenol;sodium Chemical compound [Na].OC1=CC=C(Cl)C=C1 MXJBIALFHGDUPE-UHFFFAOYSA-N 0.000 description 1
- PRLINSMUYJWPBL-UHFFFAOYSA-N 4-tert-butyl-2-chlorophenol Chemical compound CC(C)(C)C1=CC=C(O)C(Cl)=C1 PRLINSMUYJWPBL-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 241000092161 Pithys Species 0.000 description 1
- 229920006328 Styrofoam Polymers 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- KSQXVLVXUFHGJQ-UHFFFAOYSA-N sodium;2-phenylphenol Chemical compound [Na+].OC1=CC=CC=C1C1=CC=CC=C1 KSQXVLVXUFHGJQ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/24—[b,e]-condensed with two six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712117690 DE2117690A1 (de) | 1971-04-10 | 1971-04-10 | Verfahren zur Herstellung von Phenoxyphenolen bzw. Chlorphenoxyphenolen |
| BE781377A BE781377A (fr) | 1971-04-10 | 1972-03-29 | Procede de fabrication de phenoxyphenols ou de chlorophenoxyphenols |
| NL7204617A NL7204617A (enrdf_load_stackoverflow) | 1971-04-10 | 1972-04-06 | |
| IT4944472A IT952544B (it) | 1971-04-10 | 1972-04-07 | Procedimento per produrre fenossi fenoli e clorofenosifenoli |
| GB1633872A GB1342455A (en) | 1971-04-10 | 1972-04-10 | Production of phenoxy and chlorophenoxyphenols |
| FR7212505A FR2132825A1 (enrdf_load_stackoverflow) | 1971-04-10 | 1972-04-10 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712117690 DE2117690A1 (de) | 1971-04-10 | 1971-04-10 | Verfahren zur Herstellung von Phenoxyphenolen bzw. Chlorphenoxyphenolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2117690A1 true DE2117690A1 (de) | 1972-10-26 |
Family
ID=5804505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712117690 Pending DE2117690A1 (de) | 1971-04-10 | 1971-04-10 | Verfahren zur Herstellung von Phenoxyphenolen bzw. Chlorphenoxyphenolen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE781377A (enrdf_load_stackoverflow) |
| DE (1) | DE2117690A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2132825A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1342455A (enrdf_load_stackoverflow) |
| NL (1) | NL7204617A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113429268A (zh) * | 2021-06-18 | 2021-09-24 | 浙江禾本科技股份有限公司 | 一种4-苯氧基苯酚的合成方法 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2242519C2 (de) * | 1972-08-30 | 1982-03-18 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von gegebenenfalls im Kern substituierten chlorierten Diphenylethern |
| GB2185016B (en) * | 1985-12-20 | 1989-11-29 | Hardwicke Chemical Co | Process for preparing 3-phenoxybenzaldehydes |
| DE60035639T2 (de) * | 1999-05-20 | 2008-05-21 | Ciba Specialty Chemicals Holding Inc. | Hydroxydiphenyletherverbindungen |
| JP6169141B2 (ja) * | 2015-09-07 | 2017-07-26 | 住友化学株式会社 | 有機材料用の安定剤 |
-
1971
- 1971-04-10 DE DE19712117690 patent/DE2117690A1/de active Pending
-
1972
- 1972-03-29 BE BE781377A patent/BE781377A/xx unknown
- 1972-04-06 NL NL7204617A patent/NL7204617A/xx unknown
- 1972-04-10 GB GB1633872A patent/GB1342455A/en not_active Expired
- 1972-04-10 FR FR7212505A patent/FR2132825A1/fr not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113429268A (zh) * | 2021-06-18 | 2021-09-24 | 浙江禾本科技股份有限公司 | 一种4-苯氧基苯酚的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2132825A1 (enrdf_load_stackoverflow) | 1972-11-24 |
| BE781377A (fr) | 1972-07-17 |
| GB1342455A (en) | 1974-01-03 |
| NL7204617A (enrdf_load_stackoverflow) | 1972-10-12 |
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