DE2749437A1 - Verfahren zur herstellung von resorcin oder alkylsubstituierten derivaten desselben - Google Patents
Verfahren zur herstellung von resorcin oder alkylsubstituierten derivaten desselbenInfo
- Publication number
- DE2749437A1 DE2749437A1 DE19772749437 DE2749437A DE2749437A1 DE 2749437 A1 DE2749437 A1 DE 2749437A1 DE 19772749437 DE19772749437 DE 19772749437 DE 2749437 A DE2749437 A DE 2749437A DE 2749437 A1 DE2749437 A1 DE 2749437A1
- Authority
- DE
- Germany
- Prior art keywords
- resorcinol
- keto
- ester
- dihydroresorcinol
- alkyl
- 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- Withdrawn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
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229960001755 resorcinol Drugs 0.000 title 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 230000018044 dehydration Effects 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- -1 keto ester Chemical class 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229930194542 Keto Natural products 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 150000002941 palladium compounds Chemical class 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000007363 ring formation reaction Methods 0.000 description 7
- MGTZCLMLSSAXLD-UHFFFAOYSA-N 5-oxohexanoic acid Chemical compound CC(=O)CCCC(O)=O MGTZCLMLSSAXLD-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- IEHMHYAHHVRZIF-UHFFFAOYSA-N 4-methyl-5-oxohexanoic acid Chemical compound CC(=O)C(C)CCC(O)=O IEHMHYAHHVRZIF-UHFFFAOYSA-N 0.000 description 4
- FNYDIAAMUCQQDE-UHFFFAOYSA-N 4-methylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C=C1O FNYDIAAMUCQQDE-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000003245 coal Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 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
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 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
- 239000003921 oil Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| DE2749437A1 true DE2749437A1 (de) | 1978-05-11 |
Family
ID=19827168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772749437 Withdrawn DE2749437A1 (de) | 1976-11-05 | 1977-11-04 | Verfahren zur herstellung von resorcin oder alkylsubstituierten derivaten desselben |
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) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006170A1 (de) * | 1978-06-08 | 1980-01-09 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Cyclohexan-1.3-dionen aus Delta-Ketocarbonsäureestern |
| EP0008322A1 (de) * | 1978-06-08 | 1980-03-05 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Resorcinen aus Delta-Ketocarbonsäureestern und Verfahren zur Regenerierung des verwendeten Katalysators |
| 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 |
| DE3302848A1 (de) * | 1982-04-26 | 1983-11-03 | Koppers Co., Inc., 15219 Pittsburgh, Pa. | Verfahren zur herstellung von resorzin und substituierten resorzinen |
| US5744648A (en) * | 1996-08-01 | 1998-04-28 | Hoechst Celanese Corporation | Process for the manufacture of 1, 3-cyclohexanedione |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006170A1 (de) * | 1978-06-08 | 1980-01-09 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Cyclohexan-1.3-dionen aus Delta-Ketocarbonsäureestern |
| EP0008322A1 (de) * | 1978-06-08 | 1980-03-05 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Resorcinen aus Delta-Ketocarbonsäureestern und Verfahren zur Regenerierung des verwendeten Katalysators |
| 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 |
| DE3302848A1 (de) * | 1982-04-26 | 1983-11-03 | Koppers Co., Inc., 15219 Pittsburgh, Pa. | Verfahren zur herstellung von resorzin und substituierten resorzinen |
| JPS58194830A (ja) * | 1982-04-26 | 1983-11-12 | コツパ−ス・コムパニ−・インコ−ポレ−テツド | δ−ケトカルボン酸エステルの気相環化によつて誘導される１，３−環式ジオンの液相脱水素によるレゾルシンおよび置換レゾルシンの製造 |
| US5744648A (en) * | 1996-08-01 | 1998-04-28 | Hoechst Celanese Corporation | Process for the manufacture of 1, 3-cyclohexanedione |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2370021B1 (enExample) | 1983-09-16 |
| 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 |
| CA1101891A (en) | 1981-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR |
|
| 8130 | Withdrawal |