CA1085875A - Difluoroamino-pentafluorothioethanes - Google Patents
Difluoroamino-pentafluorothioethanesInfo
- Publication number
- CA1085875A CA1085875A CA871,172A CA871172A CA1085875A CA 1085875 A CA1085875 A CA 1085875A CA 871172 A CA871172 A CA 871172A CA 1085875 A CA1085875 A CA 1085875A
- Authority
- CA
- Canada
- Prior art keywords
- difluoroamino
- pentafluorothio
- difluoroamine
- temperature
- takes place
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B43/00—Compositions characterised by explosive or thermic constituents not provided for in groups C06B25/00 - C06B41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
Pentafluorothio-difluoroamine reacts with ethylenic alkyl unsaturated lower aliphatic compounds to yield difluoroamino-pentafluorothioalkane addition products containing NF2 and SF5 groups. The reaction proceeds according to the following scheme:
Pentafluorothio-difluoroamine reacts with ethylenic alkyl unsaturated lower aliphatic compounds to yield difluoroamino-pentafluorothioalkane addition products containing NF2 and SF5 groups. The reaction proceeds according to the following scheme:
Description
.
This invention relates to difluoroamino-pentafluorothioalkanes and to their process of preparation.
It has been found that pentafluorothio-difluoroam;ne, reacts with ethylenic alkyl unsaturated lower aliphatic compounds to yield an addition product conta;ning NF2 and SF5 groups. The reaction proceeds according to the following scheme:
R2\ /R3 R2\ /R3 Rl R4 Rl N
In this equation Rl, R2, R3 and R4 are radicals selected from the group oonsisting of hydrogen, lower alkyl, nitro, halogen, nitrile, carbonyl and carbethoxy. Since the product contains both NF2 and SF5 groups, it is a high energy compound, suitable for use as a rocket fuel.
The reaction according to one aspect of the present invention takes place merely by heating the pentafluorothio-difluoroamine with the ethylenic alkyl unsaturated lower aliphatic compound. The temperature may vary from about 50 to about 250 C. Preferred temperature ranges are from 100-150 C.
The time o:i~ reaction ;s dependent upon the temperature, but usually varies from about 30 hours to about 5 minutes. Thereaction takes place under super-atmospheric pressure. Such pressures may conveniently range from about 1 to about 100 atmosphere.
The following Examples are given to illustrate embodiments of the :
present invention.
E~cam ple -Into an evacuated pressure vessel cooled in liquid nitrogen was distilled pentafluorothio-difluoroamine, F2N-SF5(7. Og, 0. 039 mole) followed by ethylene (3. Og., 0. 107 mole). The bomb was allowed to warm up to room temperature and heated at 75 C. for 30hours. The gases coming off from the pressure vessel were condensed in a liquid nitrogen cooled trap under vacuum. The gaseous fraction at room temperature was analyæed by gas chromatography and mass spectrometry to give SF4, SOF2, traces 9~
of NF2-SF5. The liquid remaining at room temperature W~8 found to be SOF2 (traces) and mainly difluoroamino-pentafluorothioethane, F2N-CH2-CH2-SF5, which had a retention time of 66.1 minutes at 95C. and was identified by mass spectrometry. Yield, 2,5g, b.p.~92C. The pressure vessel was opened and a liquid remained which was rnostly F2N-CH2-CH2-SF5. Yield, 5.5g. The total yield was ~.Og. or 98% from F2N-SF5. The heat of vaporization was determined to be 8820 calories per mole per degree Centigrade; the density to be 1.64, and the refractive index 1 . 3585 .
Difluoroamino-pentafluorothioethane is a colourless liquid, unstable in water, soluble in chloroform and organic solvents. It liber-ates io~ine from a sodium iodide solution. Its density is greater than 1Ø
The mass spectrogram consists of peaks assigned to NF, SF, SF, SF, SF4, SF5 and CH2NF, CHNF, CNF.
E~ample 2 In a similar manner, propylene was reacted with F2N-SF5 to yield CH3C~H-CH2-SF5 which was identified by chromatography and mass spectrometry, It is a liquid, b.p.~106 C. showing the same chemical property as the ethylene adduct. The yield was 95 per cent from F2N-SF5.
The heat of vaporization is 8990 calories per mole per degree Centigrade;
the density is 1.54, and the refractive index is 1.3580.
The process of synthesis of the difluoroamino-pentafluorothio-alkanes is most advantageously conducted, as hereinbefore specified, in a pressure vessel and can be conducted by passing the gases or vapours through a tubular reactor for a suitable residence time.
This invention relates to difluoroamino-pentafluorothioalkanes and to their process of preparation.
It has been found that pentafluorothio-difluoroam;ne, reacts with ethylenic alkyl unsaturated lower aliphatic compounds to yield an addition product conta;ning NF2 and SF5 groups. The reaction proceeds according to the following scheme:
R2\ /R3 R2\ /R3 Rl R4 Rl N
In this equation Rl, R2, R3 and R4 are radicals selected from the group oonsisting of hydrogen, lower alkyl, nitro, halogen, nitrile, carbonyl and carbethoxy. Since the product contains both NF2 and SF5 groups, it is a high energy compound, suitable for use as a rocket fuel.
The reaction according to one aspect of the present invention takes place merely by heating the pentafluorothio-difluoroamine with the ethylenic alkyl unsaturated lower aliphatic compound. The temperature may vary from about 50 to about 250 C. Preferred temperature ranges are from 100-150 C.
The time o:i~ reaction ;s dependent upon the temperature, but usually varies from about 30 hours to about 5 minutes. Thereaction takes place under super-atmospheric pressure. Such pressures may conveniently range from about 1 to about 100 atmosphere.
The following Examples are given to illustrate embodiments of the :
present invention.
E~cam ple -Into an evacuated pressure vessel cooled in liquid nitrogen was distilled pentafluorothio-difluoroamine, F2N-SF5(7. Og, 0. 039 mole) followed by ethylene (3. Og., 0. 107 mole). The bomb was allowed to warm up to room temperature and heated at 75 C. for 30hours. The gases coming off from the pressure vessel were condensed in a liquid nitrogen cooled trap under vacuum. The gaseous fraction at room temperature was analyæed by gas chromatography and mass spectrometry to give SF4, SOF2, traces 9~
of NF2-SF5. The liquid remaining at room temperature W~8 found to be SOF2 (traces) and mainly difluoroamino-pentafluorothioethane, F2N-CH2-CH2-SF5, which had a retention time of 66.1 minutes at 95C. and was identified by mass spectrometry. Yield, 2,5g, b.p.~92C. The pressure vessel was opened and a liquid remained which was rnostly F2N-CH2-CH2-SF5. Yield, 5.5g. The total yield was ~.Og. or 98% from F2N-SF5. The heat of vaporization was determined to be 8820 calories per mole per degree Centigrade; the density to be 1.64, and the refractive index 1 . 3585 .
Difluoroamino-pentafluorothioethane is a colourless liquid, unstable in water, soluble in chloroform and organic solvents. It liber-ates io~ine from a sodium iodide solution. Its density is greater than 1Ø
The mass spectrogram consists of peaks assigned to NF, SF, SF, SF, SF4, SF5 and CH2NF, CHNF, CNF.
E~ample 2 In a similar manner, propylene was reacted with F2N-SF5 to yield CH3C~H-CH2-SF5 which was identified by chromatography and mass spectrometry, It is a liquid, b.p.~106 C. showing the same chemical property as the ethylene adduct. The yield was 95 per cent from F2N-SF5.
The heat of vaporization is 8990 calories per mole per degree Centigrade;
the density is 1.54, and the refractive index is 1.3580.
The process of synthesis of the difluoroamino-pentafluorothio-alkanes is most advantageously conducted, as hereinbefore specified, in a pressure vessel and can be conducted by passing the gases or vapours through a tubular reactor for a suitable residence time.
Claims (15)
1. Difluoroamino-pentafluorothio lower alkanes.
2. Difluoroamino-pentafluoroethane.
3. Difluoroamino-pentafluoropropane.
4. A process for the preparation of difluoroamino-pentafluorothio-alkanes which comprises reacting pentafluorothio-difluoroamine with an ethylenically unsaturated lower aliphatic compound.
5. The process of claim 4 wherein the reaction takes place at elevated temperatures.
6. The process of claim 4 wherein the temperature is about 60 to about 250°C.
7. The process of claim 6 wherein the temperature is 100-150°C.
8. The process of claim 5 wherein the reaction takes place under pressure at elevated temperatures.
9. The process of claim 8 wherein the pressure is about 1 to about 100 atmospheres.
10. A process for the production of difluoroamino-pentafluoroethane which comprises heating pentafluorothio-difluoroamine with ethane under pressure.
11. A process for the production of difluoroamine-pentafluoropro-pane which comprises heating pentafluorothio-difluoroamine with propylene under pressure.
12. The process of claim 10 wherein the pressure is a maximum of 100 atmospheres.
13. The process of claim 11 wherein the pressure is a maximum of 100 atmospheres.
14. The process of claim 10 wherein the reaction takes place at a temperature of about 75°C.
15. The process of claim 11 wherein the reaction takes place at a temperature of 50-250°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA871,172A CA1085875A (en) | 1963-03-19 | 1963-03-19 | Difluoroamino-pentafluorothioethanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA871,172A CA1085875A (en) | 1963-03-19 | 1963-03-19 | Difluoroamino-pentafluorothioethanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1085875A true CA1085875A (en) | 1980-09-16 |
Family
ID=4141689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA871,172A Expired CA1085875A (en) | 1963-03-19 | 1963-03-19 | Difluoroamino-pentafluorothioethanes |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1085875A (en) |
-
1963
- 1963-03-19 CA CA871,172A patent/CA1085875A/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |