CA1101891A - Process for the preparation of resorcinol or alkylsubstituted derivatives thereof - Google Patents
Process for the preparation of resorcinol or alkylsubstituted derivatives thereofInfo
- Publication number
- CA1101891A CA1101891A CA289,769A CA289769A CA1101891A CA 1101891 A CA1101891 A CA 1101891A CA 289769 A CA289769 A CA 289769A CA 1101891 A CA1101891 A CA 1101891A
- Authority
- CA
- Canada
- Prior art keywords
- resorcinol
- group
- dihydroresorcinol
- keto
- ester
- 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.)
- Expired
Links
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 20
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000007791 liquid phase Substances 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 10
- -1 keto ester Chemical class 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 229930194542 Keto Natural products 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 239000007792 gaseous phase Substances 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 150000002941 palladium compounds Chemical class 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000012808 vapor phase Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000004702 methyl esters Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- MGTZCLMLSSAXLD-UHFFFAOYSA-N 5-oxohexanoic acid Chemical compound CC(=O)CCCC(O)=O MGTZCLMLSSAXLD-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- FNYDIAAMUCQQDE-UHFFFAOYSA-N 4-methylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C=C1O FNYDIAAMUCQQDE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- IEHMHYAHHVRZIF-UHFFFAOYSA-N 4-methyl-5-oxohexanoic acid Chemical compound CC(=O)C(C)CCC(O)=O IEHMHYAHHVRZIF-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof
-
- 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
- C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
- C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7612281 | 1976-11-05 | ||
| NL7612281A NL7612281A (nl) | 1976-11-05 | 1976-11-05 | Werkwijze voor de bereiding van resorcinol en alkylgesubstitueerde derivaten hiervan. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1101891A true CA1101891A (en) | 1981-05-26 |
Family
ID=19827168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA289,769A Expired CA1101891A (en) | 1976-11-05 | 1977-10-28 | Process for the preparation of resorcinol or alkylsubstituted derivatives thereof |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4154965A (enExample) |
| JP (1) | JPS5359635A (enExample) |
| BE (1) | BE860260A (enExample) |
| CA (1) | CA1101891A (enExample) |
| CH (1) | CH628011A5 (enExample) |
| DE (1) | DE2749437A1 (enExample) |
| FR (1) | FR2370021A1 (enExample) |
| GB (1) | GB1546287A (enExample) |
| IT (1) | IT1090425B (enExample) |
| NL (1) | NL7612281A (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2825073A1 (de) * | 1978-06-08 | 1979-12-20 | Hoechst Ag | Verfahren zur herstellung von resorcinen aus delta-ketocarbonsaeureestern |
| DE2825170A1 (de) * | 1978-06-08 | 1979-12-13 | Hoechst Ag | Verfahren zur herstellung von cyclohexan-1.3-dionen aus delta -ketocarbonsaeureestern |
| US4399310A (en) * | 1981-09-18 | 1983-08-16 | Koppers Company, Inc. | Preparation of 1,3-cyclic diones by vapor phase cyclization of delta-keto carboxylic acid esters utilizing carrier condensable under ambient conditions |
| US4431848A (en) * | 1982-04-26 | 1984-02-14 | Koppers Company, Inc. | Preparation of resorcinol and substituted resorcinols by liquid-phase dehydrogenation of 1,3-cyclic diones derived by vapor-phase cyclization of delta-keto carboxylic acid esters |
| US5233095A (en) * | 1986-03-18 | 1993-08-03 | Catalytica, Inc. | Process for manufacture of resorcinol |
| US4861921A (en) * | 1986-03-18 | 1989-08-29 | Catalytica Associates | Process for manufacture of resorcinol |
| US4798911A (en) * | 1987-07-20 | 1989-01-17 | Eastman Kodak Company | Catalyst composition and method for selective dehydrogenation |
| US5744648A (en) * | 1996-08-01 | 1998-04-28 | Hoechst Celanese Corporation | Process for the manufacture of 1, 3-cyclohexanedione |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3627833A (en) * | 1968-07-05 | 1971-12-14 | Mobil Oil Corp | Preparation of dihydroresorcinol |
| NL174939C (nl) * | 1973-03-14 | 1984-09-03 | Stamicarbon | Werkwijze voor de bereiding van resorcinol en alkylgesubstitueerde derivaten hiervan. |
| NL174940C (nl) * | 1973-03-14 | 1984-09-03 | Stamicarbon | Werkwijze voor de bereiding van cyclohexaan-1,3-dion en alkylgesubstitueerde derivaten hiervan. |
| DE2437983C3 (de) * | 1974-08-07 | 1982-04-01 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Resorcinen |
| DE2450086C3 (de) * | 1974-10-22 | 1981-10-08 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Resorcinen aus δ -Ketocarbonsäuren oder ihren Lactonen |
-
1976
- 1976-11-05 NL NL7612281A patent/NL7612281A/xx not_active Application Discontinuation
-
1977
- 1977-10-28 CA CA289,769A patent/CA1101891A/en not_active Expired
- 1977-10-28 BE BE182171A patent/BE860260A/xx not_active IP Right Cessation
- 1977-10-31 GB GB45258/77A patent/GB1546287A/en not_active Expired
- 1977-11-01 US US05/847,652 patent/US4154965A/en not_active Expired - Lifetime
- 1977-11-02 JP JP13215677A patent/JPS5359635A/ja active Pending
- 1977-11-02 IT IT51660/77A patent/IT1090425B/it active
- 1977-11-03 FR FR7733024A patent/FR2370021A1/fr active Granted
- 1977-11-03 CH CH1339277A patent/CH628011A5/de not_active IP Right Cessation
- 1977-11-04 DE DE19772749437 patent/DE2749437A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2370021B1 (enExample) | 1983-09-16 |
| DE2749437A1 (de) | 1978-05-11 |
| IT1090425B (it) | 1985-06-26 |
| BE860260A (nl) | 1978-04-28 |
| CH628011A5 (de) | 1982-02-15 |
| NL7612281A (nl) | 1978-05-09 |
| US4154965A (en) | 1979-05-15 |
| FR2370021A1 (fr) | 1978-06-02 |
| JPS5359635A (en) | 1978-05-29 |
| GB1546287A (en) | 1979-05-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |