DE3025350C2 - Verfahren zur Herstellung von 2-Methylenaldehyden - Google Patents
Verfahren zur Herstellung von 2-MethylenaldehydenInfo
- Publication number
- DE3025350C2 DE3025350C2 DE3025350A DE3025350A DE3025350C2 DE 3025350 C2 DE3025350 C2 DE 3025350C2 DE 3025350 A DE3025350 A DE 3025350A DE 3025350 A DE3025350 A DE 3025350A DE 3025350 C2 DE3025350 C2 DE 3025350C2
- Authority
- DE
- Germany
- Prior art keywords
- aldehyde
- formaldehyde
- aldehydes
- secondary amine
- reaction
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 4
- 239000008098 formaldehyde solution Substances 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 3
- 150000001299 aldehydes Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000003335 secondary amines Chemical class 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- -1 aliphatic aldehydes Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 229940005605 valeric acid Drugs 0.000 description 2
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 1
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3025350A DE3025350C2 (de) | 1980-07-04 | 1980-07-04 | Verfahren zur Herstellung von 2-Methylenaldehyden |
| US06/220,382 US4346239A (en) | 1980-07-04 | 1980-12-29 | Process for the preparation of 2-methylene aldehydes |
| NLAANVRAGE8102971,A NL187012C (nl) | 1980-07-04 | 1981-06-19 | Werkwijze voor de bereiding van 2-methyleenaldehyden. |
| FR8112534A FR2486069A2 (fr) | 1980-07-04 | 1981-06-25 | Procede pour la preparation de 2-methylene-aldehydes |
| CH4246/81A CH651006A5 (de) | 1980-07-04 | 1981-06-26 | Verfahren zur herstellung von 2-methylenaldehyden. |
| JP56101374A JPS5745123A (en) | 1980-07-04 | 1981-07-01 | Manufacture of 2-methylenealdehyde |
| GB8120616A GB2078748B (en) | 1980-07-04 | 1981-07-03 | Preparation of 2-methylenealdehydes |
| IT8148830A IT1209875B (it) | 1980-07-04 | 1981-07-03 | Procedimento per la produzione di 2-metilenaldeidi |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3025350A DE3025350C2 (de) | 1980-07-04 | 1980-07-04 | Verfahren zur Herstellung von 2-Methylenaldehyden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3025350A1 DE3025350A1 (de) | 1982-01-28 |
| DE3025350C2 true DE3025350C2 (de) | 1993-10-14 |
Family
ID=6106399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3025350A Expired - Fee Related DE3025350C2 (de) | 1980-07-04 | 1980-07-04 | Verfahren zur Herstellung von 2-Methylenaldehyden |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4346239A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5745123A (cg-RX-API-DMAC7.html) |
| CH (1) | CH651006A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3025350C2 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2486069A2 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2078748B (cg-RX-API-DMAC7.html) |
| IT (1) | IT1209875B (cg-RX-API-DMAC7.html) |
| NL (1) | NL187012C (cg-RX-API-DMAC7.html) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3106557A1 (de) * | 1981-02-21 | 1982-09-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von (alpha)-alkylacroleinen |
| DE3213681A1 (de) * | 1982-04-14 | 1983-10-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von (alpha)-alkylacroleinen |
| US4739111A (en) * | 1983-05-26 | 1988-04-19 | Exxon Research & Engineering Co. | Alpha, beta-ethylenically unsaturated acids and derivatives thereof using a multicomponent acidic catalyst composition containing zirconium |
| EP0162891B1 (en) * | 1983-11-10 | 1990-05-23 | Monsanto Company | Mixture of amines and process for producing it |
| JPS6133137A (ja) * | 1984-07-24 | 1986-02-17 | Sumitomo Chem Co Ltd | チグリルアルデヒドの製造方法 |
| US4683342A (en) * | 1985-09-26 | 1987-07-28 | International Flavors & Fragrances Inc. | Process for preparing natural benzaldehyde and acetaldehyde, natural benzaldehyde and acetaldehyde compositions, products produced thereby and organoleptic utilities therefor |
| US4740639A (en) * | 1987-06-12 | 1988-04-26 | Eastman Kodak Company | Process for preparation of 2,4-disubstituted-1,5-pentanediols |
| DE3740293A1 (de) * | 1987-11-27 | 1989-06-01 | Hoechst Ag | Verfahren zur herstellung von alpha-alkylacroleinen |
| DE3811039A1 (de) * | 1988-03-31 | 1989-10-19 | Hoechst Ag | Verfahren zur gewinnung von 2-methylalkanalen aus gemischen isomerer aldehyde |
| DE3842186A1 (de) * | 1988-12-15 | 1990-06-21 | Basf Ag | Verfahren zur gewinnung von 2-alkylverzweigten alkanalen aus alkanalgemischen |
| US4945184A (en) * | 1989-06-19 | 1990-07-31 | Aristech Chemical Corporation | Preparation of unsaturated ketones |
| ES2714899T3 (es) * | 2016-09-30 | 2019-05-30 | Oxea Gmbh | Método de producción continuo para 2-metilenos-alcanales |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE875194C (de) * | 1939-08-24 | 1953-04-30 | Basf Ag | Herstellung ª‡-substituierter Acroleine |
| US2518416A (en) * | 1948-04-28 | 1950-08-08 | Rohm & Haas | Preparation of acroleins |
| US2639295A (en) * | 1948-07-16 | 1953-05-19 | Eastman Kodak Co | Manufacture of unsaturated aldehydes |
| US3463818A (en) * | 1966-01-25 | 1969-08-26 | Int Flavors & Fragrances Inc | Unsaturated aldehydes and alcohols |
| BE758908R (fr) * | 1968-09-27 | 1971-05-13 | Basf Ag | Procede de preparation de dimethyl-2, 2-hydroxy-3- |
| DE2855504C3 (de) * | 1978-12-22 | 1989-04-06 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur Herstellung von Methacrolein |
| JPS5587739A (en) * | 1978-12-26 | 1980-07-02 | Mitsui Petrochem Ind Ltd | Preparation of aromatic aldehyde or ketone |
-
1980
- 1980-07-04 DE DE3025350A patent/DE3025350C2/de not_active Expired - Fee Related
- 1980-12-29 US US06/220,382 patent/US4346239A/en not_active Expired - Lifetime
-
1981
- 1981-06-19 NL NLAANVRAGE8102971,A patent/NL187012C/xx not_active IP Right Cessation
- 1981-06-25 FR FR8112534A patent/FR2486069A2/fr active Granted
- 1981-06-26 CH CH4246/81A patent/CH651006A5/de not_active IP Right Cessation
- 1981-07-01 JP JP56101374A patent/JPS5745123A/ja active Pending
- 1981-07-03 GB GB8120616A patent/GB2078748B/en not_active Expired
- 1981-07-03 IT IT8148830A patent/IT1209875B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| CH651006A5 (de) | 1985-08-30 |
| NL187012B (nl) | 1990-12-03 |
| GB2078748A (en) | 1982-01-13 |
| DE3025350A1 (de) | 1982-01-28 |
| FR2486069A2 (fr) | 1982-01-08 |
| US4346239A (en) | 1982-08-24 |
| FR2486069B2 (cg-RX-API-DMAC7.html) | 1984-10-19 |
| GB2078748B (en) | 1984-07-11 |
| NL187012C (nl) | 1991-05-01 |
| NL8102971A (nl) | 1982-02-01 |
| JPS5745123A (en) | 1982-03-13 |
| IT1209875B (it) | 1989-08-30 |
| IT8148830A0 (it) | 1981-07-03 |
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Legal Events
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8340 | Patent of addition ceased/non-payment of fee of main patent |