DE863190C - Process for the production of trifluoroethyl alcohol - Google Patents

Process for the production of trifluoroethyl alcohol

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Publication number
DE863190C
DE863190C DEF3649D DEF0003649D DE863190C DE 863190 C DE863190 C DE 863190C DE F3649 D DEF3649 D DE F3649D DE F0003649 D DEF0003649 D DE F0003649D DE 863190 C DE863190 C DE 863190C
Authority
DE
Germany
Prior art keywords
trifluoroethyl
alcohol
production
weight
parts
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
Application number
DEF3649D
Other languages
German (de)
Inventor
Otto Dr Scherer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to DEF3649D priority Critical patent/DE863190C/en
Application granted granted Critical
Publication of DE863190C publication Critical patent/DE863190C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/34—Halogenated alcohols

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von Trifluoräthylalkohol Der Trifluoräthylalkohol ist von S. w arts (s.Bull. Soc. chim. Belg. Bd. ¢3, S. 471) durch katalytische Hydrierung von Trifluoressigsäureanhydrid in Gegenwart von Platinschwarz bei 5o Atmosphären Druck hergestellt worden. Aus 2 Mol Trifluoressigsäureanhydrid erhält man theoretisch neben 2 Mol Trifluoressigsäure nur 2 Mol Trifluoräthylalkohol. Das Verfahren ist deshalb technisch unwirtschaftlich, zumal die Trifluoressigsäure sehr mühsam durch- Oxydation von 3-Aminobenzotrifluorid gewonnen werden muß.Process for the preparation of trifluoroethyl alcohol Trifluoroethyl alcohol is from S. w arts (see Bull. Soc. chim. Belg. Vol. [3, p. 471) by catalytic hydrogenation of trifluoroacetic anhydride in the presence of platinum black at 50 atmospheres Print has been made. Theoretically, 2 moles of trifluoroacetic anhydride are obtained in addition to 2 moles of trifluoroacetic acid, only 2 moles of trifluoroethyl alcohol. The procedure is therefore technically uneconomical, especially since the trifluoroacetic acid is very laboriously Oxidation of 3-aminobenzotrifluoride must be obtained.

Es wurde nun .gefunden, @daß man den Trifluoräthylalkohol in einfacher und glatter Weise erhalten kann, wenn man ß, ß, ß-Trifluoräthylchlorid mit Alkaliacetat in Gegenwart oder Abwesenheit von Lösungsmitteln bei mindestens 2oo° unter Druck umsetzt und den erhaltenen Essigsäuretrifluoräthylester anschließend mit Alkalilauge verseift. Dias ß, ß, ß-Trifluoräthylchlorid kann nach den Angaben der amerikanischen Patentschrift 2:230 925 hergestellt werden. Der Trifluoräthylal:kohol ist für die Einführung von trifluorierten Äthoxygruppen in Farbstoffe von :Bedeutung.It has now been found that you can use the trifluoroethyl alcohol in a simple way and can be obtained smoothly if you ß, ß, ß-trifluoroethyl chloride with alkali acetate in the presence or absence of solvents at at least 2oo ° under pressure reacted and the resulting acetic acid trifluoroethyl ester then with alkali saponified. This ß, ß, ß-Trifluoroäthylchlorid can according to the information of the American Patent 2: 230 925 can be produced. The trifluoroethylal: alcohol is for the Introduction of trifluorinated ethoxy groups in dyes of: Importance.

Beispiele 1. 1185 Gewichtsteile ß, ß, ß-Trifluoräthylchlorid und 105o Gewichtsteile wasserfreies Kal.i.umacetat werden in einer verbleiten druckfesten Bombe q.0. bis 5ö Stunden auf Zoo bis 25ö°' erhitzt. Der Anfangsdruck beträgt ungefähr 8o bis' 9o Atmosphären; er fällt im Verlauf der Reaktion auf ungefähr 5o Atmosphären ab.Examples 1. 1185 parts by weight of β, β, β-trifluoroethyl chloride and 105o Parts by weight of anhydrous Kal.i.umacetat are pressure-resistant in a leaded bomb q.0. Heated up to 25 ° 'at the zoo for up to 5ö hours. The initial pressure is about 8o to '9o atmospheres; it falls to roughly in the course of the reaction 5o atmospheres.

Nach Ablassen der Bombe-erhält man 1300 Gewichtsteile Kondensat;- davon sind 120o Gewichtsteile Essigsäuretrifluoräthylester vom Siedepunkt 78° und Zoo Gewichtsteile nicht umgesetztes ß, ß, ß-Trifluoräthylchlorid. Das entspricht einer Ausbeute an Trifluoräthylalkoholacetat von 91,5%, bezogen .auf das in Reaktion getretene Trifluorätfhylchlorid.After the bomb has been released, 1,300 parts by weight of condensate are obtained, 120o parts by weight of trifluoroethyl acetate with a boiling point of 78 ° and zoo parts by weight of unreacted β, β, β-trifluoroethyl chloride. This corresponds to a yield of trifluoroethyl alcohol acetate of 91.5%, based on the trifluoroethyl chloride which has reacted.

2. 1185 Gewichtsteile Trifluoräthylchlorid, looö Gewichtsteile wasserfreies Natriumacetat und looo Gewichtsteile Eisessig werden_ unter den gleichen Bifedingungen, wie in Beispiel r eschrieben, umgesetzt. Man erhält ungefähr 110o Gewichtsteile Essigsäuretrifluoräthylester. Durch Verseifung des nach Beispiel 1 oder 2 erhaltenen. Essigsäuretriflüoräthylesters mit Alkalilauge erhält man in quantitativer Ausbeute den Trifluoräthylalkohol vom Siedepunkt 7q.°.2. 1185 parts by weight Trifluoräthylchlorid, looö parts by weight of anhydrous sodium acetate and looo parts by weight of glacial acetic acid _, reacted under the same Bifedingungen, esch rubbed as in Example r. About 110o parts by weight of trifluoroethyl acetate are obtained. By saponification of that obtained according to Example 1 or 2. Acetic acid trifluoroethyl ester with alkali lye gives the trifluoroethyl alcohol with a boiling point of 7q. ° in quantitative yield.

Claims (3)

PATENTANSPRUCH: Verfahren zur Herstellung von Trifluoräthylalkohol, .dadurch gekennzeichnet, daB man ß, ß, ß-Trifluoräthylchlorid mit Alkaliacetaten in Gegenwart oder Abwesenheit von Lösungsmitteln bei mindestens 20o° unter Druck umsetzt und den erhaltenen Essigsäuretrifluoräthylester mit Alkalilauge verseift. Ahgezogene Druckschriften: USA.-Patentschrift Nr. PATENT CLAIM: Process for the production of trifluoroethyl alcohol, Characterized by the fact that ß, ß, ß-trifluoroethyl chloride with alkali acetates in the presence or absence of solvents at at least 20o ° under pressure reacted and the resulting trifluoroethyl acetate saponified with alkali. Copied publications: U.S. Patent No. 2 230 925; Ha@u-ben, »Die Methoden der organischen Chemie«, 2,230,925; Ha @ u-ben, "The Methods of Organic Chemistry", 3. Auflage, Bd. 111 (1930), S. 5o/51.3rd edition, Vol. 111 (1930), pp. 5o / 51.
DEF3649D 1941-07-04 1941-07-04 Process for the production of trifluoroethyl alcohol Expired DE863190C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF3649D DE863190C (en) 1941-07-04 1941-07-04 Process for the production of trifluoroethyl alcohol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF3649D DE863190C (en) 1941-07-04 1941-07-04 Process for the production of trifluoroethyl alcohol

Publications (1)

Publication Number Publication Date
DE863190C true DE863190C (en) 1953-01-15

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Family Applications (1)

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DEF3649D Expired DE863190C (en) 1941-07-04 1941-07-04 Process for the production of trifluoroethyl alcohol

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DE (1) DE863190C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2868846A (en) * 1956-01-05 1959-01-13 Pennsalt Chemicals Corp Preparation of 2, 2, 2-trifluoroethanol
DE1075583B (en) * 1960-02-18 Pennsalt Chemicals Corporation, Philadelphia, Pa. (V. St. A.) Process for the production of trifluoroethanol
US4434297A (en) 1981-03-23 1984-02-28 Halocarbon Products Corporation Process for the preparation of trifluoroethanol

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2230925A (en) * 1939-03-23 1941-02-04 Kinetic Chemicals Inc Preparation of 1, 1, 1-trifluoro-2-chloro-ethane

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2230925A (en) * 1939-03-23 1941-02-04 Kinetic Chemicals Inc Preparation of 1, 1, 1-trifluoro-2-chloro-ethane

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1075583B (en) * 1960-02-18 Pennsalt Chemicals Corporation, Philadelphia, Pa. (V. St. A.) Process for the production of trifluoroethanol
US2868846A (en) * 1956-01-05 1959-01-13 Pennsalt Chemicals Corp Preparation of 2, 2, 2-trifluoroethanol
US4434297A (en) 1981-03-23 1984-02-28 Halocarbon Products Corporation Process for the preparation of trifluoroethanol
EP0101526A1 (en) * 1981-03-23 1984-02-29 Halocarbon Products Corporation Process for the preparation of trifluoroethanol

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