DE2412371C2 - Herstellung von Resorcin und alkylsubstituierten Resorcinen - Google Patents
Herstellung von Resorcin und alkylsubstituierten ResorcinenInfo
- Publication number
- DE2412371C2 DE2412371C2 DE2412371A DE2412371A DE2412371C2 DE 2412371 C2 DE2412371 C2 DE 2412371C2 DE 2412371 A DE2412371 A DE 2412371A DE 2412371 A DE2412371 A DE 2412371A DE 2412371 C2 DE2412371 C2 DE 2412371C2
- Authority
- DE
- Germany
- Prior art keywords
- resorcinol
- catalyst
- ester
- weight
- hydrogen
- 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 description 38
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 150000004702 methyl esters Chemical class 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- 239000007789 gas Substances 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 13
- 239000002253 acid Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- MGTZCLMLSSAXLD-UHFFFAOYSA-N 5-oxohexanoic acid Chemical compound CC(=O)CCCC(O)=O MGTZCLMLSSAXLD-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 238000006356 dehydrogenation reaction Methods 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 239000008246 gaseous mixture Substances 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- -1 keto ester Chemical class 0.000 description 3
- IEHMHYAHHVRZIF-UHFFFAOYSA-N 4-methyl-5-oxohexanoic acid Chemical compound CC(=O)C(C)CCC(O)=O IEHMHYAHHVRZIF-UHFFFAOYSA-N 0.000 description 2
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BXDJIVKCVVTETR-UHFFFAOYSA-N 4-methylcyclohexane-1,3-dione Chemical compound CC1CCC(=O)CC1=O BXDJIVKCVVTETR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241001163743 Perlodes Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- KVBYPTUGEKVEIJ-UHFFFAOYSA-N benzene-1,3-diol;formaldehyde Chemical compound O=C.OC1=CC=CC(O)=C1 KVBYPTUGEKVEIJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 210000000540 fraction c Anatomy 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JRTYPQGPARWINR-UHFFFAOYSA-N palladium platinum Chemical compound [Pd].[Pt] JRTYPQGPARWINR-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
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 |
|---|---|---|---|
| NLAANVRAGE7303537,A NL174939C (nl) | 1973-03-14 | 1973-03-14 | Werkwijze voor de bereiding van resorcinol en alkylgesubstitueerde derivaten hiervan. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2412371A1 DE2412371A1 (de) | 1974-09-19 |
| DE2412371C2 true DE2412371C2 (de) | 1983-01-20 |
Family
ID=19818431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2412371A Expired DE2412371C2 (de) | 1973-03-14 | 1974-03-14 | Herstellung von Resorcin und alkylsubstituierten Resorcinen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3950438A (enExample) |
| JP (1) | JPS5811846B2 (enExample) |
| BE (1) | BE812306A (enExample) |
| CA (1) | CA1016959A (enExample) |
| CH (1) | CH589579A5 (enExample) |
| DE (1) | DE2412371C2 (enExample) |
| FR (1) | FR2221428B1 (enExample) |
| GB (1) | GB1398377A (enExample) |
| IT (1) | IT1008420B (enExample) |
| NL (1) | NL174939C (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2448677C3 (de) * | 1974-10-12 | 1980-04-03 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Cyclohexan-13-dionen bzw. 6-Alkyl-3, 4-dihydro-2-pyranonen |
| DE2450086C3 (de) * | 1974-10-22 | 1981-10-08 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Resorcinen aus δ -Ketocarbonsäuren oder ihren Lactonen |
| DE2533920C2 (de) * | 1975-07-30 | 1982-12-09 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Resorcinen |
| DE2533919C3 (de) * | 1975-07-30 | 1980-09-18 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von CyclohexandioneM 1.3) |
| US4165339A (en) * | 1976-02-12 | 1979-08-21 | Union Carbide Corporation | Catalytic aldol condensations |
| NL7612281A (nl) * | 1976-11-05 | 1978-05-09 | Stamicarbon | Werkwijze voor de bereiding van resorcinol en alkylgesubstitueerde derivaten hiervan. |
| DE2825073A1 (de) * | 1978-06-08 | 1979-12-20 | Hoechst Ag | Verfahren zur herstellung von resorcinen aus delta-ketocarbonsaeureestern |
| NL7905024A (nl) * | 1979-06-28 | 1980-12-30 | Stamicarbon | Werkwijze voor de bereiding van, eventueel alkyl- -gesubstitueerd, resorcinol en daarbij te gebruiken katalysator. |
| NL8102390A (nl) * | 1981-05-15 | 1982-12-01 | Stamicarbon | Werkwijze voor de bereiding van indool of een methylgesubstitueerd indool eventueel gemengd met het overeenkomstige gehydrogeneerde produkt. |
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3580970A (en) * | 1967-11-22 | 1971-05-25 | Gulf Research Development Co | Dehydrogenation of cycloaliphatic ketones and alcohols |
| US3691102A (en) * | 1970-05-11 | 1972-09-12 | Gulf Research Development Co | Group viii metal-tin catalyst and method of making same |
-
1973
- 1973-03-14 NL NLAANVRAGE7303537,A patent/NL174939C/xx not_active IP Right Cessation
-
1974
- 1974-03-11 US US05/450,219 patent/US3950438A/en not_active Expired - Lifetime
- 1974-03-12 FR FR7408313A patent/FR2221428B1/fr not_active Expired
- 1974-03-12 GB GB1102574A patent/GB1398377A/en not_active Expired
- 1974-03-12 CH CH346274A patent/CH589579A5/xx not_active IP Right Cessation
- 1974-03-13 JP JP49028944A patent/JPS5811846B2/ja not_active Expired
- 1974-03-13 CA CA194,939A patent/CA1016959A/en not_active Expired
- 1974-03-14 DE DE2412371A patent/DE2412371C2/de not_active Expired
- 1974-03-14 BE BE142008A patent/BE812306A/xx not_active IP Right Cessation
- 1974-03-15 IT IT49257/74A patent/IT1008420B/it active
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| NL174939B (nl) | 1984-04-02 |
| JPS5024231A (enExample) | 1975-03-15 |
| BE812306A (fr) | 1974-09-16 |
| DE2412371A1 (de) | 1974-09-19 |
| CH589579A5 (enExample) | 1977-07-15 |
| CA1016959A (en) | 1977-09-06 |
| NL7303537A (enExample) | 1974-09-17 |
| GB1398377A (en) | 1975-06-18 |
| FR2221428B1 (enExample) | 1977-09-23 |
| US3950438A (en) | 1976-04-13 |
| FR2221428A1 (enExample) | 1974-10-11 |
| NL174939C (nl) | 1984-09-03 |
| JPS5811846B2 (ja) | 1983-03-04 |
| IT1008420B (it) | 1976-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |