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)
Description
Claims (1)
- Verfahren zur Herstellung von 2-Methylenaldehyden in weiterer Ausgestaltung des Gegenstandes des Patents 28 55 504 durch Umsetzung eines Aldehydes der allgemeinen Formel R-CH₂-CHO, worin R für einen Alkylrest mit 2 bis 12 Kohlenstoffatomen steht, mit Formaldehyd in Gegenwart eines sekundären Amins, das Alkylreste mit insgesamt bis zu 16 Kohlenstoffatomen enthält und einer Carbonsäure, dadurch gekennzeichnet, daß man einem Gemisch aus Aldehyd, wäßriger Formaldehydlösung und einer Carbonsäure mit bis zu 5 Kohlenstoffatomen unter Kühlen das sekundäre Amin zusetzt, wobei je mol Aldehyd 0,01 bis 0,05 mol des sekundären Amins und 0,005 bis 0,02 mol Carbonsäure angewandt werden, und darauf bei Temperaturen von 70 bis 120°C und Drücken von 0,2 bis 1,0 MPa reagieren läßt.
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 |
IT8148830A IT1209875B (it) | 1980-07-04 | 1981-07-03 | Procedimento per la produzione di 2-metilenaldeidi |
GB8120616A GB2078748B (en) | 1980-07-04 | 1981-07-03 | Preparation of 2-methylenealdehydes |
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 (de) |
JP (1) | JPS5745123A (de) |
CH (1) | CH651006A5 (de) |
DE (1) | DE3025350C2 (de) |
FR (1) | FR2486069A2 (de) |
GB (1) | GB2078748B (de) |
IT (1) | IT1209875B (de) |
NL (1) | NL187012C (de) |
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 |
WO1985002173A1 (en) * | 1983-11-10 | 1985-05-23 | Monsanto Company | New route to long chain amines |
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 |
EP3301084B1 (de) * | 2016-09-30 | 2018-12-12 | OXEA GmbH | Kontinuierliches herstellungsverfahren für 2-methylenalkanale |
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 IT IT8148830A patent/IT1209875B/it active
- 1981-07-03 GB GB8120616A patent/GB2078748B/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
GB2078748B (en) | 1984-07-11 |
US4346239A (en) | 1982-08-24 |
GB2078748A (en) | 1982-01-13 |
NL187012C (nl) | 1991-05-01 |
IT1209875B (it) | 1989-08-30 |
NL8102971A (nl) | 1982-02-01 |
NL187012B (nl) | 1990-12-03 |
JPS5745123A (en) | 1982-03-13 |
FR2486069B2 (de) | 1984-10-19 |
DE3025350A1 (de) | 1982-01-28 |
IT8148830A0 (it) | 1981-07-03 |
FR2486069A2 (fr) | 1982-01-08 |
CH651006A5 (de) | 1985-08-30 |
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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 |