GB873251A - Process for the production of fluorinated 1,3,5-triazines - Google Patents
Process for the production of fluorinated 1,3,5-triazinesInfo
- Publication number
- GB873251A GB873251A GB12796/58A GB1279658A GB873251A GB 873251 A GB873251 A GB 873251A GB 12796/58 A GB12796/58 A GB 12796/58A GB 1279658 A GB1279658 A GB 1279658A GB 873251 A GB873251 A GB 873251A
- Authority
- GB
- United Kingdom
- Prior art keywords
- potassium
- triazines
- fluoride
- compounds
- sodium
- 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
- 150000000182 1,3,5-triazines Chemical class 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 abstract 2
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 abstract 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- SGQWCRMKJYYBKC-UHFFFAOYSA-M 14986-57-3 Chemical compound [K+].[O-]S(F)=O SGQWCRMKJYYBKC-UHFFFAOYSA-M 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910001618 alkaline earth metal fluoride Inorganic materials 0.000 abstract 1
- 150000001495 arsenic compounds Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical class [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 150000002222 fluorine compounds Chemical class 0.000 abstract 1
- 229940093920 gynecological arsenic compound Drugs 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Fluorinated-1,3,5-triazines of the formula <FORM:0873251/III/1> where X is F, Cl, Br or I are prepared by reacting cyanuric chloride, bromide, or iodide with hydrogen fluoride, a neutral, or acid ammonium, alkali metal or alkaline earth metal fluoride, or a salt of fluorosulphinic acid in the absence of water at an elevated temperature. Suitable fluorine compounds are anhydrous HF, sodium, potassium, ammonium or calcium fluorides, sodium, or potassium, hydrogen fluorides, or potassium fluorosulphinate FSOOK. Reaction may be at 100-350 DEG C., under superatmospheric pressure up to 200 atms., in a solvent such as aliphatic, or aromatic, hydrocarbons, or halogenated hydrocarbons, e.g. benzene, toluene, xylene, decane, or tetrahydro-, or decahydro-, naphthalene, and in the presence of arsenic compounds, p antimonous oxide, or antimonic chloride as catalyst. Examples refer to the preparation of trifluoro-1,3,5-triazine (cyanuric fluoride), and mixtures of 2,4-difluoro-6-chloro-, and 2-fluoro-4,6-dichloro-, 1,3,5 triazines, and of the corresponding bromo-compounds. The product may be purified and separated by distillation.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE873251X | 1957-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB873251A true GB873251A (en) | 1961-07-19 |
Family
ID=6816361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12796/58A Expired GB873251A (en) | 1957-04-25 | 1958-04-22 | Process for the production of fluorinated 1,3,5-triazines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB873251A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3162632A (en) * | 1964-12-22 | Preparation of cyanuric fluorides | ||
| US4161593A (en) * | 1977-01-22 | 1979-07-17 | Bayer Aktiengesellschaft | Process for the preparation of triazines containing a mixture of chlorine and fluorine substituents, and of cyanuric fluoride |
| US4332939A (en) | 1977-04-06 | 1982-06-01 | Ciba-Geigy Ag | Process for the preparation of fluorinated s-triazines |
-
1958
- 1958-04-22 GB GB12796/58A patent/GB873251A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3162632A (en) * | 1964-12-22 | Preparation of cyanuric fluorides | ||
| US4161593A (en) * | 1977-01-22 | 1979-07-17 | Bayer Aktiengesellschaft | Process for the preparation of triazines containing a mixture of chlorine and fluorine substituents, and of cyanuric fluoride |
| US4332939A (en) | 1977-04-06 | 1982-06-01 | Ciba-Geigy Ag | Process for the preparation of fluorinated s-triazines |
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