DE2140738B2 - Verfahren zur Herstellung von Monomethyläthern von Dihydroxybenzole!! - Google Patents
Verfahren zur Herstellung von Monomethyläthern von Dihydroxybenzole!!Info
- Publication number
- DE2140738B2 DE2140738B2 DE2140738A DE2140738A DE2140738B2 DE 2140738 B2 DE2140738 B2 DE 2140738B2 DE 2140738 A DE2140738 A DE 2140738A DE 2140738 A DE2140738 A DE 2140738A DE 2140738 B2 DE2140738 B2 DE 2140738B2
- Authority
- DE
- Germany
- Prior art keywords
- dihydroxybenzenes
- reaction
- catechol
- methanol
- monomethyl ethers
- 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- Withdrawn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
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 17
- 150000005205 dihydroxybenzenes Chemical class 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 20
- YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 claims description 7
- 229910000149 boron phosphate Inorganic materials 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 36
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 20
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 11
- 229960001867 guaiacol Drugs 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WGCUZUDACXOATC-UHFFFAOYSA-N 1,4-dimethylcyclohexa-3,5-diene-1,2-diol Chemical compound CC1=CC(O)C(C)(O)C=C1 WGCUZUDACXOATC-UHFFFAOYSA-N 0.000 description 1
- RYHGQTREHREIBC-UHFFFAOYSA-N 3,4-dimethylbenzene-1,2-diol Chemical compound CC1=CC=C(O)C(O)=C1C RYHGQTREHREIBC-UHFFFAOYSA-N 0.000 description 1
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 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)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE787411D BE787411A (fr) | 1971-08-13 | Procede de preparation d'ethers monomethyliques de dihydroxybenzenes | |
| DE2140738A DE2140738B2 (de) | 1971-08-13 | 1971-08-13 | Verfahren zur Herstellung von Monomethyläthern von Dihydroxybenzole!! |
| US277205A US3895076A (en) | 1971-08-13 | 1972-08-02 | Process for the preparation of monomethylethers of dihydroxybenzene |
| NL7210942A NL7210942A (OSRAM) | 1971-08-13 | 1972-08-10 | |
| JP7955172A JPS554092B2 (OSRAM) | 1971-08-13 | 1972-08-10 | |
| GB3749172A GB1394221A (en) | 1971-08-13 | 1972-08-11 | Process for the preparation of monomethylethers of dihydroxy benzenes |
| IT52124/72A IT961970B (it) | 1971-08-13 | 1972-08-11 | Procedimento per produrre eteri monometilici di diidrossibenzoli |
| CH1194072A CH587208A5 (OSRAM) | 1971-08-13 | 1972-08-11 | |
| FR7229226A FR2149461B1 (OSRAM) | 1971-08-13 | 1972-08-11 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2140738A DE2140738B2 (de) | 1971-08-13 | 1971-08-13 | Verfahren zur Herstellung von Monomethyläthern von Dihydroxybenzole!! |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2140738A1 DE2140738A1 (de) | 1973-02-22 |
| DE2140738B2 true DE2140738B2 (de) | 1979-02-08 |
Family
ID=5816731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2140738A Withdrawn DE2140738B2 (de) | 1971-08-13 | 1971-08-13 | Verfahren zur Herstellung von Monomethyläthern von Dihydroxybenzole!! |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3895076A (OSRAM) |
| JP (1) | JPS554092B2 (OSRAM) |
| BE (1) | BE787411A (OSRAM) |
| CH (1) | CH587208A5 (OSRAM) |
| DE (1) | DE2140738B2 (OSRAM) |
| FR (1) | FR2149461B1 (OSRAM) |
| GB (1) | GB1394221A (OSRAM) |
| IT (1) | IT961970B (OSRAM) |
| NL (1) | NL7210942A (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51108026A (en) * | 1975-03-14 | 1976-09-25 | Ube Industries | 2kafuenooru no monoarukirueeteru no seizoho |
| JPS5236634A (en) * | 1975-09-17 | 1977-03-22 | Ube Ind Ltd | Process for preparation of monovalent phenol alkyl ethers |
| DE2740718C2 (de) * | 1977-09-09 | 1987-04-30 | Eastman Kodak Co., Rochester, N.Y. | Verfahren zur Herstellung von Monoalkylethern von Hydrochinon bzw. Alkylhydrochinonen |
| US4294991A (en) * | 1978-05-10 | 1981-10-13 | Eastman Kodak Company | Process for monoalkylation of dihydric phenols |
| US4490553A (en) * | 1980-08-29 | 1984-12-25 | Celanese Corporation | Process for production of ethyl acrylate |
| IT1209617B (it) * | 1985-03-01 | 1989-08-30 | Eniricerche Spa | Procedimento per la preparazione di alchilarileteri. |
| IT1190016B (it) * | 1986-05-27 | 1988-02-10 | Eniricerche Spa | Procedimento per la preparazione di alchilarileteri |
| FR2635103B1 (fr) * | 1988-08-05 | 1990-11-02 | Rhone Poulenc Chimie | Procede de monomethylation de composes phenoliques |
| EP0420756B1 (en) * | 1989-09-29 | 1994-12-14 | Ube Industries, Ltd. | Process for catalytically producing monoalkylether of dihydric phenol compound |
| DE4104417A1 (de) * | 1991-02-14 | 1992-08-20 | Basf Ag | Verfahren zur herstellung von brenzcatechinmonoethern und brenzcatechinen |
| US10266554B2 (en) | 2017-05-31 | 2019-04-23 | Momentive Performance Materials Inc. | Preparation of isocyanatosilanes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3689570A (en) * | 1970-01-14 | 1972-09-05 | Peter S Gradeff | Monoalkylation of unsubstituted dihydric phenols with lower alkyl chlorides using alkali metal carbonates or bicarbonates as a condensing agent |
-
0
- BE BE787411D patent/BE787411A/xx unknown
-
1971
- 1971-08-13 DE DE2140738A patent/DE2140738B2/de not_active Withdrawn
-
1972
- 1972-08-02 US US277205A patent/US3895076A/en not_active Expired - Lifetime
- 1972-08-10 JP JP7955172A patent/JPS554092B2/ja not_active Expired
- 1972-08-10 NL NL7210942A patent/NL7210942A/xx unknown
- 1972-08-11 GB GB3749172A patent/GB1394221A/en not_active Expired
- 1972-08-11 CH CH1194072A patent/CH587208A5/xx not_active IP Right Cessation
- 1972-08-11 IT IT52124/72A patent/IT961970B/it active
- 1972-08-11 FR FR7229226A patent/FR2149461B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1394221A (en) | 1975-05-14 |
| FR2149461B1 (OSRAM) | 1977-12-30 |
| CH587208A5 (OSRAM) | 1977-04-29 |
| JPS4828439A (OSRAM) | 1973-04-14 |
| US3895076A (en) | 1975-07-15 |
| JPS554092B2 (OSRAM) | 1980-01-29 |
| FR2149461A1 (OSRAM) | 1973-03-30 |
| BE787411A (fr) | 1973-02-12 |
| DE2140738A1 (de) | 1973-02-22 |
| NL7210942A (OSRAM) | 1973-02-15 |
| IT961970B (it) | 1973-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8230 | Patent withdrawn |