CA1096867A - Process for the production of 2,4-difluoro-6-amino-s- triazine - Google Patents
Process for the production of 2,4-difluoro-6-amino-s- triazineInfo
- Publication number
- CA1096867A CA1096867A CA319,680A CA319680A CA1096867A CA 1096867 A CA1096867 A CA 1096867A CA 319680 A CA319680 A CA 319680A CA 1096867 A CA1096867 A CA 1096867A
- Authority
- CA
- Canada
- Prior art keywords
- ammonia
- triazine
- amino
- difluoro
- cyanuric fluoride
- 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
- 238000000034 method Methods 0.000 title claims abstract description 13
- BPWSQBVQMDHRSQ-UHFFFAOYSA-N 4,6-difluoro-1,3,5-triazin-2-amine Chemical compound NC1=NC(F)=NC(F)=N1 BPWSQBVQMDHRSQ-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 36
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 18
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 238000007792 addition Methods 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- -1 photochemicals Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- LHYQAEFVHIZFLR-UHFFFAOYSA-L 4-(4-diazonio-3-methoxyphenyl)-2-methoxybenzenediazonium;dichloride Chemical compound [Cl-].[Cl-].C1=C([N+]#N)C(OC)=CC(C=2C=C(OC)C([N+]#N)=CC=2)=C1 LHYQAEFVHIZFLR-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- DBZLAIRBFBGCNR-UHFFFAOYSA-N FN1NC(=CC(=N1)F)N Chemical compound FN1NC(=CC(=N1)F)N DBZLAIRBFBGCNR-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
-
- 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
- C07D251/42—One nitrogen atom
- C07D251/44—One nitrogen atom with halogen atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/046—Specific dyes not provided for in group C09B62/06 - C09B62/10
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH51678A CH638503A5 (de) | 1978-01-18 | 1978-01-18 | Verfahren zur herstellung von 2,4-difluor-6-amino-s-triazin. |
| CH516/78-6 | 1978-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1096867A true CA1096867A (en) | 1981-03-03 |
Family
ID=4188790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA319,680A Expired CA1096867A (en) | 1978-01-18 | 1979-01-16 | Process for the production of 2,4-difluoro-6-amino-s- triazine |
Country Status (11)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3171901D1 (en) * | 1980-05-30 | 1985-09-26 | Ciba Geigy Ag | Process for the preparation of amino-fluor-s-triazine dyestuffs |
| DE3727253A1 (de) * | 1987-08-15 | 1989-02-23 | Bayer Ag | Verfahren zur monoacylierung wasserloeslicher organischer aminoverbindungen mit 2,4,6-trifluortriazin in waessrigem medium |
| US8676987B2 (en) | 2008-03-21 | 2014-03-18 | Lg Electronics Inc. | Method of processing data in internet protocol television receiver and internet protocol television receiver |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670866A1 (de) * | 1967-05-11 | 1971-03-11 | Bayer Ag | Fluortriazinverbindungen |
-
1978
- 1978-01-18 CH CH51678A patent/CH638503A5/de not_active IP Right Cessation
- 1978-12-25 JP JP15873678A patent/JPS54106482A/ja active Granted
-
1979
- 1979-01-08 US US06/001,574 patent/US4225709A/en not_active Expired - Lifetime
- 1979-01-15 FR FR7900860A patent/FR2415106A1/fr active Granted
- 1979-01-16 CA CA319,680A patent/CA1096867A/en not_active Expired
- 1979-01-16 BE BE0/192910A patent/BE873495A/xx unknown
- 1979-01-16 DE DE19792901498 patent/DE2901498A1/de active Granted
- 1979-01-17 CS CS79381A patent/CS205137B2/cs unknown
- 1979-01-17 BR BR7900298A patent/BR7900298A/pt unknown
- 1979-01-17 GB GB7901727A patent/GB2013663B/en not_active Expired
- 1979-01-17 ES ES476914A patent/ES476914A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2901498C2 (US07816562-20101019-C00012.png) | 1988-06-16 |
| JPS54106482A (en) | 1979-08-21 |
| GB2013663A (en) | 1979-08-15 |
| GB2013663B (en) | 1982-06-03 |
| BR7900298A (pt) | 1979-08-14 |
| CH638503A5 (de) | 1983-09-30 |
| ES476914A1 (es) | 1979-11-16 |
| BE873495A (fr) | 1979-07-16 |
| CS205137B2 (en) | 1981-04-30 |
| DE2901498A1 (de) | 1979-07-19 |
| JPS643871B2 (US07816562-20101019-C00012.png) | 1989-01-23 |
| FR2415106B1 (US07816562-20101019-C00012.png) | 1981-02-27 |
| FR2415106A1 (fr) | 1979-08-17 |
| US4225709A (en) | 1980-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3985749A (en) | Process for preparation of 4-aminoquinazoline | |
| CA1096867A (en) | Process for the production of 2,4-difluoro-6-amino-s- triazine | |
| JPS6165856A (ja) | α‐（ο‐クロルフエニル）‐アミノメチレン‐β‐ホルミルアミノプロピオニトリル及びその製法 | |
| EP0014844B1 (de) | Fluortriazin-Derivate, Verfahren zur Herstellung von Fluortriazin-Derivaten und von Reaktivfarbstoffen und deren Verwendung | |
| US2907762A (en) | New anthraquinonoid dyestuffs | |
| US2826580A (en) | Derivatives of y | |
| US3900510A (en) | Sulfuric acid ester of 1-aminobenzene-4-(' -hydroxyethyl-sulfone)-2-sulfonic acid, the 4-vinylsulfone compound thereof and a process for their preparation | |
| JPH0130826B2 (US07816562-20101019-C00012.png) | ||
| US4785081A (en) | Process for the production of reactive dyes by adiabatic reaction of cyanuric chloride with an amino group-containing dye at elevated temperature | |
| US4361698A (en) | Process for the manufacture of dihalogenotriazinylamino-naphthol compounds | |
| US3983115A (en) | Bis-dihalogeno-s-triazinyl ureas | |
| US3954759A (en) | Process for preparation of 6-substituted 5-fluorouracil derivatives | |
| US4256882A (en) | Reactive dyestuffs | |
| JPH0616958A (ja) | 反応性染料 | |
| US3086020A (en) | Alkali and alkaline earth metal 2, 4-dichloro-5-pyrimidine sulfonate | |
| US3496214A (en) | Condensation products of cyanoacetyl urea and amine complexes | |
| US3810892A (en) | Trichloroisocyanuric acid manufacture | |
| CA1108142A (en) | Process for the preparation of 2-isopropylamino pyrimidine | |
| US3622608A (en) | Nitro anilino-polyalkylene polyamines and the salts thereof | |
| US2774761A (en) | Preparation of sulfuric acid half esters of leuco vat dyes | |
| GB1491954A (en) | Process for the preparation of concentrated solutions of urea compounds | |
| JPS5880349A (ja) | 水溶性モノアゾーピリドン化合物及びこれを用いて染色する方法 | |
| US3691164A (en) | Production improvement for substituted triazines | |
| US3359286A (en) | Preparation of 1-amino-4-(3'-thiosulfato-ethylsulfonyl-anilino)-anthraquinone-2-sulfonic acid | |
| US3644389A (en) | 6-hydroxy-1 3-dialkyl benzotriazolium derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |