CA1117980A - Process for producing aromatic aldehydes, in particular benzaldehyde and derivatives thereof - Google Patents
Process for producing aromatic aldehydes, in particular benzaldehyde and derivatives thereofInfo
- Publication number
- CA1117980A CA1117980A CA000320390A CA320390A CA1117980A CA 1117980 A CA1117980 A CA 1117980A CA 000320390 A CA000320390 A CA 000320390A CA 320390 A CA320390 A CA 320390A CA 1117980 A CA1117980 A CA 1117980A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- quinoline
- solution
- trimethoxy
- process according
- 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
- 150000003934 aromatic aldehydes Chemical class 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 25
- 230000008569 process Effects 0.000 title claims description 18
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title description 14
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 title description 7
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 14
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 35
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 239000005864 Sulphur Substances 0.000 claims description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 150000001299 aldehydes Chemical class 0.000 abstract description 3
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000009467 reduction Effects 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- VGGWRNXXWACLNH-UHFFFAOYSA-N [3-oxo-3-(3,4,5-trimethoxyphenyl)propyl] hydrogen carbonate Chemical compound COC1=CC(C(=O)CCOC(O)=O)=CC(OC)=C1OC VGGWRNXXWACLNH-UHFFFAOYSA-N 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- -1 methoxy-benzoyl-ethyl carbonate Chemical compound 0.000 description 3
- QPHLRCUCFDXGLY-UHFFFAOYSA-N (3,4,5-trimethoxyphenyl)methanol Chemical compound COC1=CC(CO)=CC(OC)=C1OC QPHLRCUCFDXGLY-UHFFFAOYSA-N 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- KCIZTNZGSBSSRM-UHFFFAOYSA-N 3,4,5-Trimethoxytoluene Chemical compound COC1=CC(C)=CC(OC)=C1OC KCIZTNZGSBSSRM-UHFFFAOYSA-N 0.000 description 1
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
- KLSHZDPXXKAHIJ-UHFFFAOYSA-N 3-bromo-4-hydroxy-5-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(Br)=C1O KLSHZDPXXKAHIJ-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- AESSRVJSJDMVGC-UHFFFAOYSA-N CN(C)C.[Cl] Chemical compound CN(C)C.[Cl] AESSRVJSJDMVGC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- LNCIVKPQULKBSP-UHFFFAOYSA-N OC(=O)OCCC(=O)C1=CC=CC=C1 Chemical compound OC(=O)OCCC(=O)C1=CC=CC=C1 LNCIVKPQULKBSP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical class C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000007787 solid 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
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT47813A/78 | 1978-01-27 | ||
| IT47813/78A IT1155795B (it) | 1978-01-27 | 1978-01-27 | Metodo di sintesi per la preparazione della 3,4,5-trimetossibenzaldeide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1117980A true CA1117980A (en) | 1982-02-09 |
Family
ID=11262676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000320390A Expired CA1117980A (en) | 1978-01-27 | 1979-01-26 | Process for producing aromatic aldehydes, in particular benzaldehyde and derivatives thereof |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4240984A (en, 2012) |
| JP (1) | JPS54117432A (en, 2012) |
| AT (1) | AT367012B (en, 2012) |
| AU (1) | AU524947B2 (en, 2012) |
| BE (1) | BE873647A (en, 2012) |
| CA (1) | CA1117980A (en, 2012) |
| CH (1) | CH636333A5 (en, 2012) |
| DE (1) | DE2902542A1 (en, 2012) |
| DK (1) | DK34079A (en, 2012) |
| ES (1) | ES477208A1 (en, 2012) |
| FR (1) | FR2415615A1 (en, 2012) |
| GB (1) | GB2013202B (en, 2012) |
| GR (1) | GR65656B (en, 2012) |
| IE (1) | IE47907B1 (en, 2012) |
| IT (1) | IT1155795B (en, 2012) |
| LU (1) | LU80833A1 (en, 2012) |
| NL (1) | NL7900396A (en, 2012) |
| NO (1) | NO149544C (en, 2012) |
| PT (1) | PT69140A (en, 2012) |
| SE (1) | SE446973B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE443138B (sv) * | 1979-12-10 | 1986-02-17 | Berol Kemi Ab | Ytaktiv kvarter ammoniumforening samt anvendning av denna vid behandling av textil- och cellulosamaterial |
| EP0150961B1 (en) * | 1984-01-18 | 1988-05-11 | Mitsubishi Kasei Corporation | Catalytic process of producing aromatic aldehydes |
| JPS62148444A (ja) * | 1985-12-19 | 1987-07-02 | チバ−ガイギ− ア−ゲ− | ４，４′−スチルベンジアルデヒド類の製法 |
| JPS62265240A (ja) * | 1986-05-12 | 1987-11-18 | Shin Etsu Chem Co Ltd | カルボン酸の還元方法 |
| US6441246B1 (en) * | 1998-08-27 | 2002-08-27 | Japan Science And Technology Corporation | Catalytic synthesis of aldehydes by direct hydrogenation of carboxylic acids |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1123664A (fr) * | 1954-02-23 | 1956-09-25 | Chinoin Gyogyszer Es Vegyeszet | Procédé de préparation d'alcools primaires |
| US2883426A (en) * | 1956-10-05 | 1959-04-21 | Shell Dev | Process for the preparation of aldehydes and ketones |
| US3322833A (en) * | 1963-01-24 | 1967-05-30 | Sun Oil Co | Preparation of aromatic aldehydes |
| DE2064105C3 (de) * | 1970-12-28 | 1978-08-24 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Aldehyden |
| BE789586A (fr) * | 1972-03-27 | 1973-04-02 | Hoffmann La Roche | Procede pour la preparation de 3,4,5-trimethoxy-benzaldehyde |
| US3978140A (en) * | 1974-09-23 | 1976-08-31 | Aldrich-Boranes, Inc. | Process for the preparation of carbinols |
-
1978
- 1978-01-27 IT IT47813/78A patent/IT1155795B/it active
-
1979
- 1979-01-18 NL NL7900396A patent/NL7900396A/xx not_active Application Discontinuation
- 1979-01-18 US US06/004,448 patent/US4240984A/en not_active Expired - Lifetime
- 1979-01-19 CH CH54079A patent/CH636333A5/it not_active IP Right Cessation
- 1979-01-23 BE BE193031A patent/BE873647A/xx unknown
- 1979-01-24 DE DE19792902542 patent/DE2902542A1/de active Granted
- 1979-01-26 AT AT0059979A patent/AT367012B/de not_active IP Right Cessation
- 1979-01-26 FR FR7902126A patent/FR2415615A1/fr active Granted
- 1979-01-26 ES ES477208A patent/ES477208A1/es not_active Expired
- 1979-01-26 DK DK34079A patent/DK34079A/da not_active Application Discontinuation
- 1979-01-26 SE SE7900717A patent/SE446973B/sv not_active IP Right Cessation
- 1979-01-26 LU LU80833A patent/LU80833A1/xx unknown
- 1979-01-26 PT PT7969140A patent/PT69140A/pt unknown
- 1979-01-26 GB GB7902894A patent/GB2013202B/en not_active Expired
- 1979-01-26 NO NO790260A patent/NO149544C/no unknown
- 1979-01-26 AU AU43693/79A patent/AU524947B2/en not_active Ceased
- 1979-01-26 CA CA000320390A patent/CA1117980A/en not_active Expired
- 1979-01-27 JP JP864879A patent/JPS54117432A/ja active Granted
- 1979-01-27 GR GR58196A patent/GR65656B/el unknown
- 1979-01-30 IE IE87/79A patent/IE47907B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54117432A (en) | 1979-09-12 |
| LU80833A1 (fr) | 1979-06-05 |
| ES477208A1 (es) | 1979-10-16 |
| AU524947B2 (en) | 1982-10-14 |
| IE790087L (en) | 1979-07-27 |
| GB2013202A (en) | 1979-08-08 |
| IT1155795B (it) | 1987-01-28 |
| DE2902542A1 (de) | 1979-08-02 |
| AU4369379A (en) | 1979-08-02 |
| FR2415615A1 (fr) | 1979-08-24 |
| GB2013202B (en) | 1982-04-07 |
| IE47907B1 (en) | 1984-07-25 |
| NO149544C (no) | 1984-05-09 |
| DK34079A (da) | 1979-07-28 |
| GR65656B (en) | 1980-10-16 |
| ATA59979A (de) | 1981-10-15 |
| NO790260L (no) | 1979-07-30 |
| PT69140A (en) | 1979-02-01 |
| NL7900396A (nl) | 1979-07-31 |
| AT367012B (de) | 1982-05-25 |
| BE873647A (fr) | 1979-05-16 |
| SE446973B (sv) | 1986-10-20 |
| NO149544B (no) | 1984-01-30 |
| CH636333A5 (it) | 1983-05-31 |
| US4240984A (en) | 1980-12-23 |
| SE7900717L (sv) | 1979-07-28 |
| DE2902542C2 (en, 2012) | 1987-11-26 |
| IT7847813A0 (it) | 1978-01-27 |
| JPS6157816B2 (en, 2012) | 1986-12-09 |
| FR2415615B1 (en, 2012) | 1984-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |