FR2491457A1 - Procede pour la preparation d'ethers phenoliques - Google Patents
Procede pour la preparation d'ethers phenoliques Download PDFInfo
- Publication number
- FR2491457A1 FR2491457A1 FR8118402A FR8118402A FR2491457A1 FR 2491457 A1 FR2491457 A1 FR 2491457A1 FR 8118402 A FR8118402 A FR 8118402A FR 8118402 A FR8118402 A FR 8118402A FR 2491457 A1 FR2491457 A1 FR 2491457A1
- Authority
- FR
- France
- Prior art keywords
- reaction
- mixture
- mol
- preparation
- phenol
- 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
- 238000000034 method Methods 0.000 title abstract description 22
- 230000008569 process Effects 0.000 title abstract description 14
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 150000002170 ethers Chemical class 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 abstract description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 12
- 235000013824 polyphenols Nutrition 0.000 abstract description 11
- 239000003930 superacid Substances 0.000 abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 9
- 150000001298 alcohols Chemical class 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 28
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000002253 acid Substances 0.000 description 13
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- -1 phenolic ethers Chemical class 0.000 description 10
- 229920000557 Nafion® Polymers 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 238000006266 etherification reaction Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- ABDKAPXRBAPSQN-UHFFFAOYSA-N Brenzkatechindimethylether Natural products COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229960001867 guaiacol Drugs 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- LHGVFZTZFXWLCP-UHFFFAOYSA-N pyrocatechol monomethyl ether Natural products COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical class C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- BBGJFAYGMNGEIW-UHFFFAOYSA-N 2,6-ditert-butyl-4-[[4-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]piperazin-1-yl]methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2CCN(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)CC2)=C1 BBGJFAYGMNGEIW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GMVPRGQOIOIIMI-DODZYUBVSA-N 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DODZYUBVSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000008379 phenol ethers Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 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
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| IT25106/80A IT1132911B (it) | 1980-10-03 | 1980-10-03 | Processo per la preparazione di eteri fenolici |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2491457A1 true FR2491457A1 (fr) | 1982-04-09 |
| FR2491457B1 FR2491457B1 (enrdf_load_stackoverflow) | 1985-02-15 |
Family
ID=11215718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8118402A Granted FR2491457A1 (fr) | 1980-10-03 | 1981-09-30 | Procede pour la preparation d'ethers phenoliques |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5791940A (enrdf_load_stackoverflow) |
| BE (1) | BE890589A (enrdf_load_stackoverflow) |
| CA (1) | CA1173859A (enrdf_load_stackoverflow) |
| CH (1) | CH647221A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3139324A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2491457A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2085004B (enrdf_load_stackoverflow) |
| IT (1) | IT1132911B (enrdf_load_stackoverflow) |
| NL (1) | NL8104500A (enrdf_load_stackoverflow) |
-
1980
- 1980-10-03 IT IT25106/80A patent/IT1132911B/it active
-
1981
- 1981-09-30 FR FR8118402A patent/FR2491457A1/fr active Granted
- 1981-10-01 BE BE0/206141A patent/BE890589A/fr not_active IP Right Cessation
- 1981-10-02 CA CA000387190A patent/CA1173859A/en not_active Expired
- 1981-10-02 NL NL8104500A patent/NL8104500A/nl not_active Application Discontinuation
- 1981-10-02 GB GB8129804A patent/GB2085004B/en not_active Expired
- 1981-10-02 DE DE19813139324 patent/DE3139324A1/de not_active Withdrawn
- 1981-10-02 CH CH6365/81A patent/CH647221A5/de not_active IP Right Cessation
- 1981-10-02 JP JP56156309A patent/JPS5791940A/ja active Pending
Non-Patent Citations (1)
| Title |
|---|
| JOURNAL OF ORGANIC CHEMISTRY, vol. 43, no. 16, 4 août 1978, American Chemical Society (US) J. KASPI et al.: "Heterogeneous catalysis by solid superacids. 4. Methylation of phenols with methyl alcohol and the rearrangement of anisole and methylanisoles over a perfluorinated resinsulfonic acid (Nafion * |
Also Published As
| Publication number | Publication date |
|---|---|
| BE890589A (fr) | 1982-02-01 |
| GB2085004B (en) | 1984-11-07 |
| JPS5791940A (en) | 1982-06-08 |
| CH647221A5 (de) | 1985-01-15 |
| DE3139324A1 (de) | 1982-06-16 |
| IT1132911B (it) | 1986-07-09 |
| NL8104500A (nl) | 1982-05-03 |
| IT8025106A0 (it) | 1980-10-03 |
| CA1173859A (en) | 1984-09-04 |
| FR2491457B1 (enrdf_load_stackoverflow) | 1985-02-15 |
| GB2085004A (en) | 1982-04-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |