DE1593227A1 - Process for the preparation of 1-bromo-1,1-difluoroethane - Google Patents
Process for the preparation of 1-bromo-1,1-difluoroethaneInfo
- Publication number
- DE1593227A1 DE1593227A1 DE19631593227 DE1593227A DE1593227A1 DE 1593227 A1 DE1593227 A1 DE 1593227A1 DE 19631593227 DE19631593227 DE 19631593227 DE 1593227 A DE1593227 A DE 1593227A DE 1593227 A1 DE1593227 A1 DE 1593227A1
- Authority
- DE
- Germany
- Prior art keywords
- difluoroethane
- bromo
- bromine
- reaction
- seconds
- 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
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D1/00—Fire-extinguishing compositions; Use of chemical substances in extinguishing fires
- A62D1/0028—Liquid extinguishing substances
- A62D1/0057—Polyhaloalkanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Business, Economics & Management (AREA)
- Emergency Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fire-Extinguishing Compositions (AREA)
Description
betreffend
Verfahren zur Herstellung von 1-ürom-l,1-difLuoräthan concerning
Process for the production of 1-urom-l, 1-difluoroethane
Die Herstellung von 1-Brom-l,i-difluoräthan wurde bereits beschrieben. Z.B. Iäi3t man nach der USA-Patentschrift 2 678 953 Brom auf ein Metallsalz, insbesondere das Silbersalz, der Difluorpropionsäure bei einer Temperatur nahe 0° C einwirken. Nach dem von Haszeldine und Osborne, Journ. Chem. Soc (London) 1956, Seite 61 beschriebenen Verfahren lagert man Bromwasserstoffsäure an Vinylidenfluorid an, wodurch im wesentlichen 2-Brom-l,ldifluor-äthan und nur ein kleiner Anteil 1-Brom-l,1-difluoräthan entsteht.The production of 1-bromo-l, i-difluoroethane was already described. E.g. the USA patent specification is used 2,678,953 bromine on a metal salt, especially the silver salt, of difluoropropionic acid at a temperature act close to 0 ° C. After that of Haszeldine and Osborne, Journ. Chem. Soc (London) 1956, page 61 Process involves adding hydrobromic acid Vinylidene fluoride, essentially 2-bromo-l, ldifluoroethane and only a small proportion of 1-bromo-1,1-difluoroethane arises.
In Anbetracht des hohen Preises der verwendeten Ausgangsstoffe sind diese Herstellungsverfahren für die industrielle Herstellung nicht geeignet.In view of the high price of the raw materials used, these manufacturing processes are for the industrial production not suitable.
009829/1730009829/1730
BAD ORIGINALBATH ORIGINAL
Das erfindungsgemäße Verfahren vermeidet diesen Nachteil und gestattet eine bedeutende Verminderung der Gestehungskosten des gesuchten Produktes.The method according to the invention avoids this disadvantage and allows a significant reduction in production costs of the product you are looking for.
Die Erfindung betrifft daher ein Verfahren zur Herstellung von 1-Brom-l,1-difluoräthan, das dadurch gekennzeichnet ist, daß man 1, L-Difluoräthan mit Brom bei 350 bis 500° C umsetzt, das Reaktionsprodukt unter 40° C abkühlt und das 1-Brom-l,1-difluoräthan in an sich bekannter Weise isoliert.The invention therefore relates to a process for the preparation of 1-bromo-l, 1-difluoroethane, which is characterized is that 1, L-difluoroethane with bromine at 350 Reacts to 500 ° C, the reaction product cools below 40 ° C and the 1-bromo-l, 1-difluoroethane in per se known Way isolated.
Vorzugsweise erfolgt die Umsetzung bei einer Temperatur von etwa 400 bis etwa 450° C.The reaction is preferably carried out at a temperature of about 400 to about 450 ° C.
Nach einem bevorzugten Verfahren bringt man das gasförmige Gemisch der Reaktionsteilnehmer in einem Molverhältnis von Brom zu 1,1-Difluoräthan von 0,5 bis 1£ und vorzugsweise von etwas unter 1 zur Reaktion. Die Dauer des Kontaktes der Reaktionspartner beträgt mindestens 5 sek und im allgemeinen 10 bis 30 sek.In a preferred method, the gaseous mixture of reactants is brought in a molar ratio from bromine to 1,1-difluoroethane from 0.5 to £ 1 and preferably from slightly below 1 to the reaction. The duration of contact between the reactants is at least 5 seconds and generally 10 to 30 seconds.
Nach Abkühlen der Reaktionsprodukte auf eine unter 40° C liegende Temperatur, z.B. auf Außentemperatur, werden die nicht kondensierten Produkte mit einer alkalischen Lösung, z. B. mit einer wässrigen Natriumhydroxyd- oder Kaiiumhydroxylösung, behandelt, um die mit den Reaktionsprodukten mitgeführte Bromwasserstoffsäure und freies Brom zu entfernen. Die Produkte können hierauf nach klassischenAfter the reaction products have cooled to a temperature below 40 ° C, e.g. to outside temperature the non-condensed products with an alkaline solution, e.g. B. with an aqueous sodium hydroxide or Potassium hydroxyl solution, treated with the reaction products entrained hydrobromic acid and free bromine to remove. The products can then be based on classic
009829/1730009829/1730
BAD ORIGINALBATH ORIGINAL
Verfahren getrocknet und fraktioniert werden, um das l-Brom-l,l~difluoräthan in reinem Zustand 2u gewinnen.Process can be dried and fractionated to obtain the Obtain l-bromine-l, l-difluoroethane in the pure state.
Das erfindungsgemäße Verfahren wird durch nachstehendesBeispiel näher erläutert:The method of the invention is illustrated by the following example explained in more detail:
Durch ein Glasrohr von 40 cm Länge und 4 cm innerem Durchmesser, das sich in einer elektrisch beheizten Umhüllung befand und auf einer Temperatur nahe 4 25° G gehalten wurde, ließ man ein gasförmiges Gemisch aus 0,91t) Mol Brom je Hol 1,1-Difluoräthan hindurchstreichen. Das Gasgemisch bewegte sich durch das Hohr mit solcher Geschwindigkeit, daß die Verweilzeit des Gases in dem Hohr ungefähr 15 sek. betrug. Die das Kohr verlassenden gasförmigen Produkte durchstrichen einen aufsteigenden Wasserkühler und gelangten in zwei aufeinanderfolgende Waschflaschen, die eine 10 #ige wässrige Hatriumhydroxydlösung enthielten. Hierauf wurde das Gas zur Trocknung durch eine, mit einem Gemisch von Kalziumchlorid und Natriumhydroxyd in Plätzchenform gefüllte, Kolonne geleitet. Dann wurden die Gase mittels einer, auf ungefähr -SO C gekühlten, Kältefalle kondensiert. Dieses Kondensat enthielt 84 Gew.-^ l-Brom-l,l-difluoräthan und 16 Gew.-^ 1,1-Difluoräthan und wurde einer fraktionierten Destillation unterworfen. Die Ausbeute an l-Brom-i,l-difluoräthan betrug etwa 64^d. Th., bezogen auf eingesetztes 1,1-Difiuoräthan.Through a glass tube of 40 cm length and 4 cm inner diameter, which is in an electrically heated envelope and was kept at a temperature close to 4 25 ° G, a gaseous mixture of 0.91t) Stroke moles of bromine per hol of 1,1-difluoroethane. That Gas mixture moved through the tube at such a speed that the residence time of the gas in the tube about 15 sec. fraud. The gaseous products leaving the Kohr passed through an ascending water cooler and ended up in two successive wash bottles containing a 10 # aqueous sodium hydroxide solution contained. The gas was then dried by means of a mixture of calcium chloride and sodium hydroxide column filled in cookie form. Then the gases were cooled by means of a Cold trap condenses. This condensate contained 84 wt .- ^ l-bromo-l, l-difluoroethane and 16 wt .- ^ 1,1-difluoroethane and was subjected to fractional distillation. The yield of l-bromo-i, l-difluoroethane was about 64 ^ d. Th., Based on 1,1-Difiuoräthan used.
009829/1,730
BAD ORIGINAL : 009829 / 1.730
ORIGINAL BATHROOM:
_M_M
Claims (4)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR903763A FR1336749A (en) | 1962-07-12 | 1962-07-12 | New extinguishing agent |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1593227A1 true DE1593227A1 (en) | 1970-07-16 |
Family
ID=8783042
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19631593227 Pending DE1593227A1 (en) | 1962-07-12 | 1963-07-11 | Process for the preparation of 1-bromo-1,1-difluoroethane |
DEP32186A Pending DE1278254B (en) | 1962-07-12 | 1963-07-11 | Fire extinguishers |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEP32186A Pending DE1278254B (en) | 1962-07-12 | 1963-07-11 | Fire extinguishers |
Country Status (7)
Country | Link |
---|---|
US (1) | US3276999A (en) |
BE (1) | BE634814A (en) |
DE (2) | DE1593227A1 (en) |
FR (1) | FR1336749A (en) |
GB (2) | GB1048694A (en) |
LU (1) | LU44031A1 (en) |
NL (1) | NL295126A (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1132636A (en) * | 1965-09-22 | 1968-11-06 | Montedison Spa | Improvements in or relating to flame-extinguishing compositions |
US3480545A (en) * | 1966-08-17 | 1969-11-25 | Monsanto Res Corp | Method of controlling the spread of fires |
NL7006794A (en) * | 1969-05-16 | 1970-11-18 | ||
US3844354A (en) * | 1973-07-11 | 1974-10-29 | Dow Chemical Co | Halogenated fire extinguishing agent for total flooding system |
US4668407A (en) * | 1983-11-09 | 1987-05-26 | Gerard Mark P | Fire extinguishing composition and method for preparing same |
US5093013A (en) * | 1989-12-11 | 1992-03-03 | Halocarbon Products Corporation | Ozone friendly fire-extinguishing agents |
US5055208A (en) * | 1991-01-02 | 1991-10-08 | Powsus, Inc. | Fire extinguishing compositions |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US866437A (en) * | 1907-01-09 | 1907-09-17 | Edward M Davidson | Fire-extinguishing compound. |
US2021981A (en) * | 1930-06-23 | 1935-11-26 | Gen Motors Corp | Self propelling fire extinguishing charge containing a double halogen hydrocarbon compound |
DE587932C (en) * | 1931-07-01 | 1933-11-10 | Werner Ursum Dr | Fillings for fire extinguishers |
BE444329A (en) * | 1940-11-16 | |||
US2678953A (en) * | 1950-10-14 | 1954-05-18 | Douglas Aircraft Co Inc | Method of making fluorinated organic bromides and resulting new chemical compounds |
US2653130A (en) * | 1951-05-17 | 1953-09-22 | Du Pont | Fire extinguishing composition of cbrf or cfbrcfbr containing cf as a propellant |
US2668419A (en) * | 1951-10-26 | 1954-02-09 | Specialties Dev Corp | Fluid carbon dioxide composition |
US2757212A (en) * | 1955-03-25 | 1956-07-31 | Du Pont | Process of reacting a halogen, fluorine compound and carbon at temperatures above 1500 deg. c |
US2897151A (en) * | 1956-09-07 | 1959-07-28 | Superior Products Co | Vaporizing fire extinguisher fluid |
US2972637A (en) * | 1958-06-19 | 1961-02-21 | Du Pont | Preparation of bromofluoromethanes |
-
0
- NL NL295126D patent/NL295126A/xx unknown
- BE BE634814D patent/BE634814A/xx unknown
-
1962
- 1962-07-12 FR FR903763A patent/FR1336749A/en not_active Expired
-
1963
- 1963-07-09 LU LU44031D patent/LU44031A1/xx unknown
- 1963-07-09 US US293878A patent/US3276999A/en not_active Expired - Lifetime
- 1963-07-10 GB GB27311/63A patent/GB1048694A/en not_active Expired
- 1963-07-10 GB GB29639/66A patent/GB1048695A/en not_active Expired
- 1963-07-11 DE DE19631593227 patent/DE1593227A1/en active Pending
- 1963-07-11 DE DEP32186A patent/DE1278254B/en active Pending
Also Published As
Publication number | Publication date |
---|---|
DE1278254B (en) | 1968-09-19 |
LU44031A1 (en) | 1964-01-09 |
NL295126A (en) | |
GB1048695A (en) | 1966-11-16 |
GB1048694A (en) | 1966-11-16 |
FR1336749A (en) | 1963-09-06 |
BE634814A (en) | |
US3276999A (en) | 1966-10-04 |
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