DE2912560A1 - Verfahren zur herstellung von m-phenoxytoluol - Google Patents
Verfahren zur herstellung von m-phenoxytoluolInfo
- Publication number
- DE2912560A1 DE2912560A1 DE19792912560 DE2912560A DE2912560A1 DE 2912560 A1 DE2912560 A1 DE 2912560A1 DE 19792912560 DE19792912560 DE 19792912560 DE 2912560 A DE2912560 A DE 2912560A DE 2912560 A1 DE2912560 A1 DE 2912560A1
- Authority
- DE
- Germany
- Prior art keywords
- cresylate
- chlorobenzene
- per mole
- cresol
- potassium
- 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.)
- Withdrawn
Links
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 50
- 229940051043 cresylate Drugs 0.000 claims description 27
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 11
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 239000011591 potassium Substances 0.000 claims description 10
- 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 claims description 9
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 7
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 18
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 10
- 229930003836 cresol Natural products 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- -1 alkali metal salt Chemical class 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002989 phenols Chemical class 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
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- UJUNUASMYSTBSK-UHFFFAOYSA-N 1-(bromomethyl)-3-phenoxybenzene Chemical compound BrCC1=CC=CC(OC=2C=CC=CC=2)=C1 UJUNUASMYSTBSK-UHFFFAOYSA-N 0.000 description 1
- XGCVFGOKEISJGC-UHFFFAOYSA-N 1-(dibromomethyl)-3-phenoxybenzene Chemical compound BrC(Br)C1=CC=CC(OC=2C=CC=CC=2)=C1 XGCVFGOKEISJGC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89195178A | 1978-03-31 | 1978-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2912560A1 true DE2912560A1 (de) | 1979-10-04 |
Family
ID=25399103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792912560 Withdrawn DE2912560A1 (de) | 1978-03-31 | 1979-03-29 | Verfahren zur herstellung von m-phenoxytoluol |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS54132536A (ja) |
| BE (1) | BE874981A (ja) |
| CH (1) | CH638478A5 (ja) |
| DE (1) | DE2912560A1 (ja) |
| DK (1) | DK130179A (ja) |
| FR (1) | FR2421163A1 (ja) |
| GB (1) | GB2018244B (ja) |
| IT (1) | IT7921411A0 (ja) |
| NL (1) | NL7902447A (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2460283A1 (fr) * | 1979-07-03 | 1981-01-23 | Rhone Poulenc Ind | Procede de preparation d'ethers diaryliques |
| GB2185016B (en) * | 1985-12-20 | 1989-11-29 | Hardwicke Chemical Co | Process for preparing 3-phenoxybenzaldehydes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1415945A (en) | 1972-08-30 | 1975-12-03 | Bayer Ag | Process for the production of halogenated diphenyl ethers optionally further substituted in the nucleus |
| US4014940A (en) | 1973-01-19 | 1977-03-29 | Sumitomo Chemical Company, Limited | Process for preparing m-phenoxybenzylalcohol and side-chain halogenated m-phenoxytoluene |
-
1979
- 1979-03-21 BE BE1/9321A patent/BE874981A/xx not_active IP Right Cessation
- 1979-03-29 FR FR7907897A patent/FR2421163A1/fr active Granted
- 1979-03-29 NL NL7902447A patent/NL7902447A/xx not_active Application Discontinuation
- 1979-03-29 JP JP3634979A patent/JPS54132536A/ja active Pending
- 1979-03-29 DE DE19792912560 patent/DE2912560A1/de not_active Withdrawn
- 1979-03-29 GB GB7910938A patent/GB2018244B/en not_active Expired
- 1979-03-29 IT IT7921411A patent/IT7921411A0/it unknown
- 1979-03-29 DK DK130179A patent/DK130179A/da not_active Application Discontinuation
- 1979-03-29 CH CH294279A patent/CH638478A5/de not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1415945A (en) | 1972-08-30 | 1975-12-03 | Bayer Ag | Process for the production of halogenated diphenyl ethers optionally further substituted in the nucleus |
| US4014940A (en) | 1973-01-19 | 1977-03-29 | Sumitomo Chemical Company, Limited | Process for preparing m-phenoxybenzylalcohol and side-chain halogenated m-phenoxytoluene |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7902447A (nl) | 1979-10-02 |
| JPS54132536A (en) | 1979-10-15 |
| BE874981A (nl) | 1979-09-21 |
| GB2018244B (en) | 1982-10-20 |
| GB2018244A (en) | 1979-10-17 |
| IT7921411A0 (it) | 1979-03-29 |
| CH638478A5 (de) | 1983-09-30 |
| DK130179A (da) | 1979-10-01 |
| FR2421163B1 (ja) | 1984-05-18 |
| FR2421163A1 (fr) | 1979-10-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |