DE1593957A1 - Perfluoro-2-oxo-3,6-dimethyl-1,4-dioxane and process for its preparation - Google Patents
Perfluoro-2-oxo-3,6-dimethyl-1,4-dioxane and process for its preparationInfo
- Publication number
- DE1593957A1 DE1593957A1 DE19641593957 DE1593957A DE1593957A1 DE 1593957 A1 DE1593957 A1 DE 1593957A1 DE 19641593957 DE19641593957 DE 19641593957 DE 1593957 A DE1593957 A DE 1593957A DE 1593957 A1 DE1593957 A1 DE 1593957A1
- Authority
- DE
- Germany
- Prior art keywords
- oxo
- dimethyl
- perfluoro
- dioxane
- preparation
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/04—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
- C07C59/21—Saturated compounds having only one carboxyl group and containing keto groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/42—Halogen atoms or nitro radicals
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. WALTER ABITZ DR. DIETER F. MORF DR. HANS-A. BRAUNSDR.-ING. WALTER ABITZ DR. DIETER F. MORF DR. HANS-A. BROWN
PatentanwältePatent attorneys
Postanschrift / Postal Address 8 München 86, Postfach 860109Postal address 8 München 86, PO Box 860109
Pienzenauerstraße 28 Telefon 483225 und 486415 Telegramme: Chemindus MünchenPienzenauerstraße 28 Tel. 483225 and 486415 Telegrams: Chemindus Munich
8. Dezember 1969December 8, 1969
AD-2786-Div. Ill (P 41 955)AD-2786-Div. Ill (P 41 955)
P 15 95 957. 8 Neue UnterlagenP 15 95 957. 8 New documents
E. I. DU PONT DB NEMOURS AND COMPANY 10th and Market Streets, Wilmington» Delaware I9898, V.St.A.E. I. DU PONT DB NEMORS AND COMPANY 10th and Market Streets, Wilmington »Delaware I9898, V.St.A.
Perfluor-2-oxo-5»6-dime chyl-1,4-dioxan und Verfahren zu dessen HerstellungPerfluoro-2-oxo-5 »6-dimethyl-1,4-dioxane and Process for its manufacture
Es wurde gefunden, dass »an Perfluor-2-oxo-3,6-dimethyl· 1,4-dloxan der FormelIt was found that »on perfluoro-2-oxo-3,6-dimethyl · 1,4-dloxane of the formula
—of c:?,—Of c:?,
'■ t ι;'■ t ι;
erhält, wenn man Perfluorpyruvylfluorid oder dessen Dimer es mit Hexafluorpropylenepoxyd In einem polaren orga-obtained when perfluoropyruvyl fluoride or its dimer is combined with hexafluoropropylene epoxide in a polar orga-
BADBATH
44/178244/1782
AD-2786-Dlv. IllAD-2786-Dlv. Ill
nischen Lösungsmittel, vorzugsweise aliphatischen Polylthern mit 4 bis 10 Kohlenstoff atomen* in Gegenwart eines Alkalifluorides bei einer Temperatur unter 100 0C unset st.Niche solvents, preferably aliphatic polyethers with 4 to 10 carbon atoms * in the presence of an alkali fluoride at a temperature below 100 0 C unset st.
Die aus den Perfluorpyruvyifluorid gebildete Dioxolanverhlndung eignet sieh als Zwlsehenverbindung für die Erzeugung sauerstoffhaltig«· Fluorkohlenstoffl8sungsfflittel# die temperaturhastitndig und chemisch inert sind und trotsdeit in der für eyolisohe Xther charakteristischen Weise gut» Lösungsnittölelgensehaft«!? besitzen. Die LOsungsaittel werden aus der Moxolanverbindung durch Uinsetsung alt 9ehffefeltetr«fluorid erhalten» das die Carboxylgruppen der cyclischen^^ Verbindungen in CPg-Oruppen überfuhrt. Man erhSlt so> ein Pluorkohlenstoff« ttther-Xiösungsmittel der FormelThe dioxolane compound formed from the perfluoropyruvyifluoride is suitable as an intermediate compound for the production of oxygen-containing "· fluorocarbon solvents # which are temperature-resistant and chemically inert and yet, in the way that is characteristic of eyolisohe Xther, good" solvent oil-like "!? own. The solvents are obtained from the moxolan compound by using an oleochemical fluoride that converts the carboxyl groups of the cyclic compounds into CP groups. This gives a "fluorocarbon" thermosolvent of the formula
»— CP»- CP
CJP9 CPCJP 9 CP
Nan gibt in elften S00*iBl-Drei2ial8k»Xbeni der ein O«e-Bln« laesrohr, eine» mechanischen HUhrer uod ein Cias-Auala·*- rohr enthilt» Wobei das Qae-Auelaesrohr »it xwti hinter-Nan gives in eleventh S00 * iBl-Drei2ial8k »Xbeni der ein O« e-Bln « laesrohr, a »mechanical watch and a Cias-Auala · * - tube contains »Whereby the Qae Auelaesrohr» it xwti behind-
BADBATH
AD-2786-Biv. IHAD-2786-Biv. IH
einandergeaehalteten Kältefallen verbunden ist, deren erste während der Umsetzung auf -10 °C und zweite auf »80 °C gehalten wird, 200 g Bensophenon ein, erhitzt ihn auf 225 0C und hält ihn auf dieser Temperatur, während durch das Bensephenon unter kräftigem Rühren mit 80 ml/Min. Hexafluorpropylenepoxyd hindurchgeleitet wird· Dl· Umsetzung wird im allgemeinen 5 Std. durchgeführt und dann Abgebrochen.einandergeaehalteten cold trap is connected, the first during the reaction and second maintained at -10 ° C to "80 ° C, 200 g Bensophenon a, it is heated to 225 0 C and holding it at that temperature, while vigorously through the Bensephenon stirring at 80 ml / min. Hexafluoropropylene epoxide is passed through · Dl · The reaction is generally carried out for 5 hours and then stopped.
Das vereinigte Reaktionsprodukt' aus den beiden Vorlagen, das ein Gewicht von 150 g aufweist, besteht aus einer kleinen Meng· TrSfluoracetylfluorid, etwa 30 g nicht umgeeetst€B Hexafluorpropylenepoxyd, Rest Perfluorpyruvylfluorid» Das Perfluorpyruvylfluorid wird gereinigt, indem man es einer fraktionierten Destillation durch eine mit Olasspiralen gefüllte 0,6-m-Niedertemperaturkolonne unterwirft.The combined reaction product 'from the two templates, which has a weight of 150 g, consists of a small amount of · TrSfluoroacetyl fluoride, about 30 g not converted € B hexafluoropropylene epoxide, the remainder perfluoropyruvyl fluoride » The perfluoropyruvyl fluoride is purified by treating it subjected to fractional distillation through a 0.6 m low-temperature column filled with oil spirals.
Das Perfluorpyruvylfluorid stellt eine gelbgefärbt· Flüssigkeit dar, die bei +9 bis +10 0C siedet und charakteristische Ultrarot-Ab8orptlonfib&nden bei 5*4 und 5,6 Mikron ' ergibt;. Auch das Kernsiagnetreson&nzapektruin bestätigt die Struktur des Proc'iaktee.The perfluoropyruvyl fluoride is a yellow colored liquid which boils at +9 to +10 0 C and gives characteristic ultrared-ab8orptlon fibers at 5 * 4 and 5.6 microns. The core diagnostic resonance also confirms the structure of the Proc'iaktee.
B« Herstellung von Perfluqr-2-oxo-3«6-dimethyl«»la4-dloxan Man beschickt einen 200-ml-Kolben, der einen MagnetrUhrer B «Manufacture of Perfluor- 2-oxo-3« 6-dimethyl «» l a 4-dloxane A 200 ml flask with a magnetic stirrer is charged
00 98A4/17 8200 98A4 / 17 82
AD-2786-Dlν. IllAD-2786-Dlν. Ill
enthält» mit ) g Gäsiumfluorid und 20 ml Diäthylenglykoldimethyläther, fcUhlt den Kolben auf 0 0C und setzt 44 g PerfluorpyruvyXfluorid hinzu, hält das Reaktionsgemiech auf 0 0C und vorsetzt es allmählich mit 50»6 g Hexafluorpropylenepoxyd. Die Reaktion läuft während des Zusatzes des Epoxydss rasch ab* wobei das Epoxyd so rasch verbraucht wlrdg wie sein Zusatz erfolgt. Di« untere Schicht des Geaaffifcrealctionsproduktea wird abgetrennt und durch eine 0,9>=m-Podbielniak-Kolonne destilliert, wobei man 57 g (73 $5 Perfluop-2-oxo-3,6-dimettiy;i.~l,4-dioxen, Kp. 70P0 bis 70,5 0C,contains "with) g Gäsiumfluorid and 20 ml of diethylene glycol dimethyl ether, fcUhlt the flask to 0 0 C., and 44 g PerfluorpyruvyXfluorid added, which holds Reaktionsgemiech to 0 0 C and set before it gradually with 50" 6 g Hexafluorpropylenepoxyd. The reaction proceeds rapidly during the addition of the epoxide, with the epoxide being consumed as quickly as it is added. The lower layer of the Geaaffifcreactionsproduktea is separated and distilled through a 0.9> = m Podbielniak column, 57 g (73 $ 5 perfluop-2-oxo-3,6-dimety; i. 1,4-dioxene , Bp. 70 P 0 to 70.5 0 C,
Berechnet ftli c^j/Pa 2^*2. 6l,3 Calculates ftli c ^ j / Pa 2 ^ * 2. 6l, 3
Die Ul üraro4,' und v;«i-rfa!agnetresonan2£ip©fe:tren stijsmen de:.' Strxüik'uF der Verbiiidußg Überein«The Ul üraro 4 , ' and v ; «ir f a! Agnetresonan2 £ ip © fe: tren stijsmen de :.'Strxüik'uF the Verbiiidußg Agreement «
man asstellf öes ■Ferfluorpyy-uvylfluorides dessen Dier, des Psrfluo?··^* oxo-2*5-^tstethyl-2-flucroerhony'l-l,3 äioxoIt«Ti e^i^^UEi:, Vj.?rd ebenfalls das öiföevhyl-t, i-"»^ ,ss^ erhalten,man asstellf öes ■ Ferfluorpyy-uvylfluorides whose Dier, des Psrfluo? ·· ^ * oxo-2 * 5- ^ tstethyl-2-flucroerhony'l-l, 3 ÄioxoIt «Ti e ^ i ^^ UEi :, Vj.?rd also received the öiföevhyl- t , i - "» ^ , ss ^,
G Q J Q k 4 / · . "U 2 GQ JQ k 4 / ·. "U 2
BAD ORIGINALBATH ORIGINAL
Claims (1)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP0035354 | 1964-10-26 | ||
| DEP0041935 | 1964-10-26 | ||
| DEP0041934 | 1964-10-26 | ||
| DEP0041936 | 1964-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1593957A1 true DE1593957A1 (en) | 1970-10-29 |
Family
ID=33033201
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641593957 Pending DE1593957A1 (en) | 1964-10-26 | 1964-10-26 | Perfluoro-2-oxo-3,6-dimethyl-1,4-dioxane and process for its preparation |
| DE19641468776 Pending DE1468776B1 (en) | 1964-10-26 | 1964-10-26 | Process for the preparation of perfluoropyruvyl fluoride |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641468776 Pending DE1468776B1 (en) | 1964-10-26 | 1964-10-26 | Process for the preparation of perfluoropyruvyl fluoride |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE1593957A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1298706C (en) * | 2001-09-21 | 2007-02-07 | 杜邦公司 | Insecticidal diamides |
-
1964
- 1964-10-26 DE DE19641593957 patent/DE1593957A1/en active Pending
- 1964-10-26 DE DE19641468776 patent/DE1468776B1/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1298706C (en) * | 2001-09-21 | 2007-02-07 | 杜邦公司 | Insecticidal diamides |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1468776B1 (en) | 1970-05-21 |
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