DE2424373A1 - Verfahren zur herstellung von derivaten des malondialdehyds - Google Patents
Verfahren zur herstellung von derivaten des malondialdehydsInfo
- Publication number
- DE2424373A1 DE2424373A1 DE2424373A DE2424373A DE2424373A1 DE 2424373 A1 DE2424373 A1 DE 2424373A1 DE 2424373 A DE2424373 A DE 2424373A DE 2424373 A DE2424373 A DE 2424373A DE 2424373 A1 DE2424373 A1 DE 2424373A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- dialkylformamide
- malondialdehyde
- carbon atoms
- general formula
- 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- Withdrawn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
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical class O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 31
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 150000002084 enol ethers Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 4
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical class CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- 229960004198 guanidine Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- SJQBHNHASPQACB-ONEGZZNKSA-N (e)-1,2-dimethoxyethene Chemical group CO\C=C\OC SJQBHNHASPQACB-ONEGZZNKSA-N 0.000 description 1
- XDHOEHJVXXTEDV-HWKANZROSA-N (e)-1-ethoxyprop-1-ene Chemical compound CCO\C=C\C XDHOEHJVXXTEDV-HWKANZROSA-N 0.000 description 1
- 241001503485 Mammuthus Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229940118019 malondialdehyde Drugs 0.000 description 1
- NTYICSDTCGMBQM-UHFFFAOYSA-N n,n-bis(2-methylpropyl)formamide Chemical compound CC(C)CN(C=O)CC(C)C NTYICSDTCGMBQM-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2424373A DE2424373A1 (de) | 1974-05-20 | 1974-05-20 | Verfahren zur herstellung von derivaten des malondialdehyds |
| US05/572,135 US3974159A (en) | 1974-05-20 | 1975-04-28 | Manufacture of derivatives of malondialdehyde |
| GB19371/75A GB1499767A (en) | 1974-05-20 | 1975-05-08 | Manufacture of derivatives of malondialdehyde |
| BE156314A BE829027A (fr) | 1974-05-20 | 1975-05-13 | Procede de preparation de derives du dialdehyde malonique |
| FR7515168A FR2272072B1 (https=) | 1974-05-20 | 1975-05-15 | |
| NL7505821A NL7505821A (nl) | 1974-05-20 | 1975-05-16 | Werkwijze voor de bereiding van derivaten van malondialdehyde. |
| JP50057961A JPS511409A (en) | 1974-05-20 | 1975-05-17 | Maronjiarudehidojudotainoseiho |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2424373A DE2424373A1 (de) | 1974-05-20 | 1974-05-20 | Verfahren zur herstellung von derivaten des malondialdehyds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2424373A1 true DE2424373A1 (de) | 1975-12-11 |
Family
ID=5916013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2424373A Withdrawn DE2424373A1 (de) | 1974-05-20 | 1974-05-20 | Verfahren zur herstellung von derivaten des malondialdehyds |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3974159A (https=) |
| JP (1) | JPS511409A (https=) |
| BE (1) | BE829027A (https=) |
| DE (1) | DE2424373A1 (https=) |
| FR (1) | FR2272072B1 (https=) |
| GB (1) | GB1499767A (https=) |
| NL (1) | NL7505821A (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0057363A1 (de) * | 1981-01-30 | 1982-08-11 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Butadiendinitrilen |
| EP0057827A1 (de) * | 1981-01-30 | 1982-08-18 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 2-Aminopyridinderivaten |
-
1974
- 1974-05-20 DE DE2424373A patent/DE2424373A1/de not_active Withdrawn
-
1975
- 1975-04-28 US US05/572,135 patent/US3974159A/en not_active Expired - Lifetime
- 1975-05-08 GB GB19371/75A patent/GB1499767A/en not_active Expired
- 1975-05-13 BE BE156314A patent/BE829027A/xx unknown
- 1975-05-15 FR FR7515168A patent/FR2272072B1/fr not_active Expired
- 1975-05-16 NL NL7505821A patent/NL7505821A/xx not_active Application Discontinuation
- 1975-05-17 JP JP50057961A patent/JPS511409A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0057363A1 (de) * | 1981-01-30 | 1982-08-11 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Butadiendinitrilen |
| EP0057827A1 (de) * | 1981-01-30 | 1982-08-18 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 2-Aminopyridinderivaten |
Also Published As
| Publication number | Publication date |
|---|---|
| BE829027A (fr) | 1975-11-13 |
| JPS511409A (en) | 1976-01-08 |
| FR2272072A1 (https=) | 1975-12-19 |
| GB1499767A (en) | 1978-02-01 |
| US3974159A (en) | 1976-08-10 |
| NL7505821A (nl) | 1975-11-24 |
| FR2272072B1 (https=) | 1978-02-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0012117B1 (de) | Verfahren zur Herstellung von 2,3,5-Trichlorpyridin, 2,4,4-Trichlor-4-formyl-butyronitril als neue Verbindung und Verfahren zu dessen Herstellung | |
| DE2447348A1 (de) | Verfahren zur herstellung von diarylcarbonaten | |
| DE2528211C3 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| EP1444205A1 (de) | Verfahren zur herstellung von 2-halogenpyridincarbonsäureamiden | |
| DE68922275T2 (de) | Verfahren zur Herstellung von Monochloroacetaldehyde-Trimer. | |
| DE2424373A1 (de) | Verfahren zur herstellung von derivaten des malondialdehyds | |
| DE2924133A1 (de) | Verfahren zur kontinuierlichen cyanaethylierung | |
| CH628877A5 (de) | Verfahren zur herstellung von acylcyaniden. | |
| DE2819264C2 (de) | Verfahren zur Herstellung von Cyanopinacolon | |
| DE60110807T2 (de) | Kontinuierliches verfahren zur herstellung von pestiziden chlorthiazolen | |
| DE2614241A1 (de) | Verfahren zur herstellung von acylcyaniden | |
| DE3002553C2 (https=) | ||
| EP0090185B1 (de) | Verfahren zur Herstellung von Acetalen und Enoläthern aus Acryloxymethylenverbindungen | |
| EP0045425B1 (de) | Verfahren zur Halogenierung von gegebenenfalls substituierten 4-tert.-Butyltoluolen sowie die daraus erhaltenen Gemische aus gegebenenfalls substituierten 4-tert.-Butylbenzalhalogeniden, 4-tert.-Butylbenzylhalogeniden und 4-tert.-Butylbenzotrihalogeniden | |
| EP0523619B1 (de) | Verfahren zur Herstellung von N-Cyanimidocarbonaten | |
| DE69021535T3 (de) | Verfahren zur Herstellung von chlorierten Carbonsäurechloriden. | |
| DE68904350T2 (de) | Herstellung von 3,5,6-trichlorpyridin-2-ol und zwischenprodukte dafuer. | |
| DE2140649C3 (de) | Verfahren zur Herstellung von Tetraalkylpyrazinen | |
| DE3221239C2 (de) | Verfahren zur Herstellung von Methylformiat | |
| DE2601399C2 (de) | Cis-β-[Trimethylammonium]-acrylnitriltosylat, Verfahren zu dessen Herstellung und dessen Verwendung zur Herstellung von Cyclocytidintosylat | |
| DE2254701A1 (de) | Verfahren zur herstellung von thiazolinen-(3) | |
| DE2756560A1 (de) | Verfahren zur herstellung von piperonal | |
| DE2453365A1 (de) | Verfahren zur herstellung von n-trimethylsilylacetamid | |
| DE2717075A1 (de) | Verfahren zur herstellung von benzoylcyanid | |
| DE2303115A1 (de) | Verfahren zur halogenierung der niedrigalkylgruppen von aromatischen verbindungen unter bestrahlung mit ultraviolettem licht |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |