DE2208923A1 - Verfahren zur herstellung von perfluorcarbonsaeurenitrilen - Google Patents
Verfahren zur herstellung von perfluorcarbonsaeurenitrilenInfo
- Publication number
- DE2208923A1 DE2208923A1 DE2208923A DE2208923A DE2208923A1 DE 2208923 A1 DE2208923 A1 DE 2208923A1 DE 2208923 A DE2208923 A DE 2208923A DE 2208923 A DE2208923 A DE 2208923A DE 2208923 A1 DE2208923 A1 DE 2208923A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- gas
- phosphorus pentoxide
- temperatures
- acid nitrile
- 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
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000002825 nitriles Chemical class 0.000 title description 4
- 239000002253 acid Substances 0.000 title description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000007789 gas Substances 0.000 claims description 16
- 239000012159 carrier gas Substances 0.000 claims description 13
- -1 perfluorocarboxylic acid nitriles Chemical class 0.000 claims description 11
- BQPIYDUNTQHZBF-UHFFFAOYSA-N n,n-difluorocarbamoyl fluoride Chemical class FN(F)C(F)=O BQPIYDUNTQHZBF-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000010791 quenching Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 5
- 150000003857 carboxamides Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- UGMUDSKJLAUMTC-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanamide Chemical compound NC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UGMUDSKJLAUMTC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- KQTOYEUYHXUEDB-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanamide Chemical compound NC(=O)C(F)(F)C(F)(F)F KQTOYEUYHXUEDB-UHFFFAOYSA-N 0.000 description 1
- JBJGDLDUIBVUMC-UHFFFAOYSA-N FN(C(=O)C1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)F)F Chemical compound FN(C(=O)C1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)F)(F)F)F)F JBJGDLDUIBVUMC-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/20—Preparation of carboxylic acid nitriles by dehydration of carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE795726D BE795726A (fr) | 1972-02-25 | Procede de preparation de perfluorocarbonitriles | |
| DE2208923A DE2208923A1 (de) | 1972-02-25 | 1972-02-25 | Verfahren zur herstellung von perfluorcarbonsaeurenitrilen |
| IT20355/73A IT979082B (it) | 1972-02-25 | 1973-02-13 | Processo per la preparazione di nitrili di acidi perfluorocar bossilici |
| FR7305737A FR2173031B3 (en, 2012) | 1972-02-25 | 1973-02-19 | |
| CH240473A CH572024A5 (en, 2012) | 1972-02-25 | 1973-02-20 | |
| NL7302431A NL7302431A (en, 2012) | 1972-02-25 | 1973-02-21 | |
| CA164,605A CA981284A (en) | 1972-02-25 | 1973-02-23 | Manufacture of perfluorocarboxylic acid nitriles |
| GB894073A GB1411180A (en) | 1972-02-25 | 1973-02-23 | Manufacture of perfluorocarboxylic acid nitriles |
| US00335818A US3847964A (en) | 1972-02-25 | 1973-02-26 | Manufacture of perfluorocarboxylic acid nitriles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2208923A DE2208923A1 (de) | 1972-02-25 | 1972-02-25 | Verfahren zur herstellung von perfluorcarbonsaeurenitrilen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2208923A1 true DE2208923A1 (de) | 1973-09-06 |
Family
ID=5837068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2208923A Pending DE2208923A1 (de) | 1972-02-25 | 1972-02-25 | Verfahren zur herstellung von perfluorcarbonsaeurenitrilen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3847964A (en, 2012) |
| BE (1) | BE795726A (en, 2012) |
| CA (1) | CA981284A (en, 2012) |
| CH (1) | CH572024A5 (en, 2012) |
| DE (1) | DE2208923A1 (en, 2012) |
| FR (1) | FR2173031B3 (en, 2012) |
| GB (1) | GB1411180A (en, 2012) |
| IT (1) | IT979082B (en, 2012) |
| NL (1) | NL7302431A (en, 2012) |
-
0
- BE BE795726D patent/BE795726A/xx unknown
-
1972
- 1972-02-25 DE DE2208923A patent/DE2208923A1/de active Pending
-
1973
- 1973-02-13 IT IT20355/73A patent/IT979082B/it active
- 1973-02-19 FR FR7305737A patent/FR2173031B3/fr not_active Expired
- 1973-02-20 CH CH240473A patent/CH572024A5/xx not_active IP Right Cessation
- 1973-02-21 NL NL7302431A patent/NL7302431A/xx unknown
- 1973-02-23 CA CA164,605A patent/CA981284A/en not_active Expired
- 1973-02-23 GB GB894073A patent/GB1411180A/en not_active Expired
- 1973-02-26 US US00335818A patent/US3847964A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA981284A (en) | 1976-01-06 |
| NL7302431A (en, 2012) | 1973-08-28 |
| FR2173031B3 (en, 2012) | 1976-02-13 |
| GB1411180A (en) | 1975-10-22 |
| CH572024A5 (en, 2012) | 1976-01-30 |
| BE795726A (fr) | 1973-08-21 |
| US3847964A (en) | 1974-11-12 |
| IT979082B (it) | 1974-09-30 |
| FR2173031A1 (en, 2012) | 1973-10-05 |
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