DE2728926A1 - METHOD FOR PRODUCING 3,3-DIMETHYL-PENT-4-ENSAEURE - Google Patents
METHOD FOR PRODUCING 3,3-DIMETHYL-PENT-4-ENSAEUREInfo
- Publication number
- DE2728926A1 DE2728926A1 DE19772728926 DE2728926A DE2728926A1 DE 2728926 A1 DE2728926 A1 DE 2728926A1 DE 19772728926 DE19772728926 DE 19772728926 DE 2728926 A DE2728926 A DE 2728926A DE 2728926 A1 DE2728926 A1 DE 2728926A1
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl
- dimethylpent
- pent
- ensaeure
- producing
- 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- Withdrawn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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DR.-ING. H. FINCKE DIPL.-ING. H. BOHR DIPL.-ING. S. STAEGER DR. rer. not. R. KNEISSLDR.-ING. H. FINCKE DIPL.-ING. H. BOHR DIPL.-ING. S. STAEGER DR. Rer. not. R. KNEISSL
ti München s. 27. Juni 1977ti Munich see June 27, 1977
rornruf (J3>) · J6 6J 6.) O^ ',' ) C* rornruf (J3>) J6 6J 6.) O ^ ',' ) C *
Mop,,» No Mop ,, » No.
24 288 - Dr. K/hü24 288 - Dr. K / hü
ICI CASE PP 2887ICI CASE PP 2887
IMPERIAL CHEMICAL INDUSTRIES LTD. London - GroßbritannienIMPERIAL CHEMICAL INDUSTRIES LTD. London - Great Britain
"Verfahren zur Herstellung von 3 , 3-D Line thy 1-pent-4-ensau re""Process for the production of 3, 3-D Line thy 1-pent-4-ensau re"
PRIORITÄT: 28. Juni 1976 - Großbritannien - 26799/76PRIORITY: June 28, 1976 - Great Britain - 26799/76
Die Erfindung bezieht sich auf ein Verfahren zur Herstellung von 3 ,S-Diinethylpent-l-ensäure.The invention relates to a method of manufacture of 3, S-Diinethylpent-1-enoic acid.
3,3-Dimethylpent-4-ensäure ist ein wertvoiLes Zwischenprodukt bei der Herstellung von 3-(2,2-Dichlorovinyl)-3,3-dimethyL-cyclopropancarbonsäure. Gewisse Ester dieser Säure sind kräftige Insektizide. Beispielsweise beschreiben Kondo et al3,3-Dimethylpent-4-enoic acid is a valuable intermediate in the preparation of 3- (2,2-dichlorovinyl) -3,3-dimethyL-cyclopropanecarboxylic acid. Certain esters of this acid are powerful insecticides. For example, Kondo et al
709881/1080709881/1080
ORIGINALORIGINAL
2728Π262728Π26
(BE-PS 833 278) die Verwendung der Ester von 3,3-Dimethylpent-4-ensäure zur Herstellung des Insektizids 3-(2,2-Dichlorovinyl)-3,S-dimethylcyclopropancarbonsäure-S-phenoxybenzy lester .(BE-PS 833 278) the use of the esters of 3,3-dimethylpent-4-enoic acid for the production of the insecticide 3- (2,2-dichlorovinyl) -3, S-dimethylcyclopropanecarboxylic acid-S-phenoxybenzy lester.
Die Herstellung von 3,3-Dimethyl-4-ensäure aus 2-Äthoxycarbonyl-3,3-dimethyl-4-insäure-äthylester ist in der US-PS 3 4 52 015 beschrieben. Das verwendete Verfahren ist mühsam, umfaßt mehrere Stufen, erfordert eine Hochdruckhydrierungsvorrichtung und benötigt beträchtliche Mengen Energie. Das oben erwähnte Ausgangsmaterial selbst muß durch ein Verfahren mit mehreren Stufen hergestellt werden. The preparation of 3,3-dimethyl-4-enoic acid from ethyl 2-ethoxycarbonyl-3,3-dimethyl-4-ynoate is described in US Pat. No. 3,452,015. The process used is cumbersome, involves several steps, requires high pressure hydrogenation equipment, and consumes considerable amounts of energy. The above-mentioned starting material itself must be prepared by a multi-step process.
Das erfindungsgemäße Verfahren ist demgegenüber in der Durchführung einfach, verbraucht weniger Energie und benötigt keine spezielle oder teure Anlage.In contrast, the method according to the invention is in the Simple to carry out, uses less energy and does not require any special or expensive equipment.
Gegenstand der Erfindung ist also ein Verfahren zur Herstellung von 3,3-Dimethylpent-4-ensäure, welches dadurch ausgeführt wird, daß man 3,3-Dimethylpent-4-en-1-al mit einer wäßrigen Suspension eines Ubergangsmetalloxyds zusammenbringt. The invention therefore relates to a process for the preparation of 3,3-dimethylpent-4-enoic acid, which is carried out by bringing 3,3-dimethylpent-4-en-1-al together with an aqueous suspension of a transition metal oxide .
Die Oxydation wird vorzugsweise bei atmosphärischem Druck und bei Temperaturen im Bereich von 0 bis 600C ausgeführt. Ein bevorzugtes Übergangsmetalloxyd ist "feuchtes Silber oxyd", welches beispielsweise dadurch erhalten wird, daß roan ein lösliches Silbersalz mit einem Alkalimetallhydroxyd, wie z.B. Natriumhydroxyd, behandelt. The oxidation is preferably carried out at atmospheric pressure and at temperatures ranging from 0 to 60 0 C. A preferred transition metal oxide is "wet silver oxide", which is obtained, for example, by treating a soluble silver salt with an alkali metal hydroxide such as sodium hydroxide.
Die Erfindung liegt in der Auswahl des Oxydationsmittels. Insbesondere ergibt die Verwendung von feuchtem SilberoxydThe invention resides in the choice of oxidizing agent. In particular, the use of moist silver oxide results
709881/1080709881/1080
27283262728326
eine nahezu quantitative Umwandlung der Aldehydgruppe zur Carbonsäuregruppe ohne daß unerwünschte Nebenreaktionen stattfinden, wie z.B. Kondensationen der Aldoltype oder Oxydation der olefinischen Doppelbindung.an almost quantitative conversion of the aldehyde group to the carboxylic acid group without undesired side reactions taking place, such as condensation of the aldol type or Oxidation of the olefinic double bond.
Andere Oxydationsmittel waren nicht brauchbar, da sie entweder nicht die hohen Ausbeuten oder die reinen Produkte des erfindungsgemäßen Verfahrens ergaben. So gibt beispielsweise die Oxydation mit Luft in Gegenwart von Aluminiumoxyd oder die Verwendung von Peroxyden oder anorganischen oder organischen Persäuren auch in Gegenwart einer löslichen Selenverbindung aufgrund gleichzeitiger Oxydation der olefinischen Doppelbindung zu einem Gemisch von Produkten Anlaß,das schwierig zu trennen ist.Other oxidizing agents were not useful because they either did not provide high yields or the pure products of the method according to the invention. For example, there is oxidation with air in the presence of aluminum oxide or the use of peroxides or inorganic or organic peracids in the presence of a soluble selenium compound due to simultaneous oxidation of the olefinic double bond to form a mixture of products Occasion that is difficult to separate.
Das beim erfindungsgemäßen Verfahren verwendete 3 ,3-Dimethylpent-4-en-1 -al kann durch ein Verfahren hergestellt werden, das von P. Cresson in Bull. Soc. Chim. France, 1964, j), S. 2618-2628 beschrieben wurde.The 3,3-dimethylpent-4-en-1 used in the process according to the invention -al can be prepared by a method described by P. Cresson in Bull. Soc. Chim. France, 1964, j), Pp. 2618-2628.
Die Erfindung wird durch das folgende Beispiel näher erläutert. The invention is illustrated in more detail by the following example.
Dieses Beispiel erläutert die Oxydation von 3,3-Dimethylpent-4-en-1-al mit Silberoxyd.This example illustrates the oxidation of 3,3-dimethylpent-4-en-1-al with silver oxide.
Eine eiskalte Lösung von 1,8 g Natriumhydroxyd in Wasser wird zu einer gerührten Lösung von 3,6 g Silbernitrat in 15 ml Wasser zugegeben, was zur Bildung eines suspendierten gefällten Silberoxyds führt. Zu diesem Gemisch werden tropfenweise 1/12 g 3,3-Dimethylpent-4-en-1-al zugegeben, woraufAn ice-cold solution of 1.8 g of sodium hydroxide in water becomes a stirred solution of 3.6 g of silver nitrate in 15 ml of water are added, which leads to the formation of a suspended, precipitated silver oxide. To this mixture are added dropwise 1/12 g of 3,3-dimethylpent-4-en-1-al was added, whereupon
709881/1080709881/1080
das Rühren weitere 10 min fortgesetzt wird. Das Gemisch wird dann filtriert, und das Filtrat wird mit Xther extrahiert,
um Verunreinigungen zu entfernen. Das Filtrat wird dann mit konzentrierter Salzsäure angesäuert, und
die dabei gebildete ölige Ausfällung wird mit Chloroform extrahiert, worauf die Chloroformextrakte mit wasserfreiem
Natriumsulfat getrocknet werden. Das Lösungsmittel wird unter vermindertem Druck entfernt, wobei ein öl mit einemstirring is continued for a further 10 min. The mixture is then filtered and the filtrate is extracted with Xther to remove impurities. The filtrate is then acidified with concentrated hydrochloric acid, and
the resulting oily precipitate is extracted with chloroform, and the chloroform extracts are dried with anhydrous sodium sulfate. The solvent is removed under reduced pressure, leaving an oil with a
24
Brechungsindex von n^ = 1,4227 zurückbleibt. Dieses öl
wird durch magnetische Kernresonanzspektroskopie als 3,3-Dimethylpent-4-ensäure
identifiziert.24
Refractive index of n ^ = 1.4227 remains. This oil is identified as 3,3-dimethylpent-4-enoic acid by nuclear magnetic resonance spectroscopy.
709881/1080709881/1080
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26799/76A GB1520818A (en) | 1976-06-28 | 1976-06-28 | Process for preparing 3,3-dimethylpent-4-enoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2728926A1 true DE2728926A1 (en) | 1978-01-05 |
Family
ID=10249415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772728926 Withdrawn DE2728926A1 (en) | 1976-06-28 | 1977-06-27 | METHOD FOR PRODUCING 3,3-DIMETHYL-PENT-4-ENSAEURE |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS532415A (en) |
| AU (1) | AU507282B2 (en) |
| DE (1) | DE2728926A1 (en) |
| FR (1) | FR2356623A1 (en) |
| GB (1) | GB1520818A (en) |
| NL (1) | NL7706899A (en) |
| NZ (1) | NZ184432A (en) |
| ZA (1) | ZA773665B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0045426A1 (en) * | 1980-08-01 | 1982-02-10 | Bayer Ag | -1,1-Dichlor-3,3-dimethyl-1,4-pentadien and its use to prepare 3,3-dimethylpent-4-enoic acid |
| FR2804989A1 (en) * | 2000-02-15 | 2001-08-17 | Jacques Felli | container for exhumation of human remains has pouch with lifting eyes and lower mesh panel |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020072627A1 (en) * | 2000-10-25 | 2002-06-13 | Somaiya Organo Chemicals Limited | Process for the manufacture of alkali metal salt of sorbic acid or free Sorbic Acid by oxidation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1113852A (en) * | 1953-11-19 | 1956-04-05 | Union Carbide & Carbon Corp | Aldehyde oxidation process |
-
1976
- 1976-06-28 GB GB26799/76A patent/GB1520818A/en not_active Expired
-
1977
- 1977-06-20 NZ NZ184432A patent/NZ184432A/en unknown
- 1977-06-20 ZA ZA00773665A patent/ZA773665B/en unknown
- 1977-06-22 NL NL7706899A patent/NL7706899A/en not_active Application Discontinuation
- 1977-06-23 AU AU26381/77A patent/AU507282B2/en not_active Expired
- 1977-06-27 FR FR7719645A patent/FR2356623A1/en active Pending
- 1977-06-27 DE DE19772728926 patent/DE2728926A1/en not_active Withdrawn
- 1977-06-28 JP JP7623677A patent/JPS532415A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0045426A1 (en) * | 1980-08-01 | 1982-02-10 | Bayer Ag | -1,1-Dichlor-3,3-dimethyl-1,4-pentadien and its use to prepare 3,3-dimethylpent-4-enoic acid |
| FR2804989A1 (en) * | 2000-02-15 | 2001-08-17 | Jacques Felli | container for exhumation of human remains has pouch with lifting eyes and lower mesh panel |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7706899A (en) | 1977-12-30 |
| JPS532415A (en) | 1978-01-11 |
| AU507282B2 (en) | 1980-02-07 |
| GB1520818A (en) | 1978-08-09 |
| AU2638177A (en) | 1979-01-04 |
| NZ184432A (en) | 1978-09-25 |
| FR2356623A1 (en) | 1978-01-27 |
| ZA773665B (en) | 1978-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |