GB970024A - Preparation of tetrachloroxylylenediamines - Google Patents
Preparation of tetrachloroxylylenediaminesInfo
- Publication number
- GB970024A GB970024A GB14158/63A GB1415863A GB970024A GB 970024 A GB970024 A GB 970024A GB 14158/63 A GB14158/63 A GB 14158/63A GB 1415863 A GB1415863 A GB 1415863A GB 970024 A GB970024 A GB 970024A
- Authority
- GB
- United Kingdom
- Prior art keywords
- meta
- isomer
- mixture
- temperature
- hydrogen chloride
- 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
- JRLHCCTVNWABTH-UHFFFAOYSA-N n,n-dichloro-1-[2-[(dichloroamino)methyl]phenyl]methanamine Chemical class ClN(Cl)CC1=CC=CC=C1CN(Cl)Cl JRLHCCTVNWABTH-UHFFFAOYSA-N 0.000 title abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- WEWXCIOGPKAVFO-UHFFFAOYSA-N 1,2-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1C(Cl)(Cl)Cl WEWXCIOGPKAVFO-UHFFFAOYSA-N 0.000 abstract 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 2
- 229910052742 iron Inorganic materials 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- SCOSFGXUBLANNC-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5,6-dimethylbenzene Chemical group CC1=C(C)C(Cl)=C(Cl)C(Cl)=C1Cl SCOSFGXUBLANNC-UHFFFAOYSA-N 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A tetrachloroxylylenediamine is made by aminating the corresponding tetrachloroxylylene dichloride with liquid ammonia at a temperature of at least 20 DEG C., e.g. 20-90 DEG C., under super-atmospheric pressure sufficient to keep the ammonia in liquid form, say 100-700 p.s.i.g. The product is a mixture of ortho, meta and para isomers and the meta-isomer may be separated by treating the mixture with aqueous hydrogen chloride to dissolve the meta-isomer and separating the solution from the ortho- and para isomers. The meta-isomer is then re-precipitated with NaOH. The starting material may be made by dissolving xylene in a solvent, such as carbon tetrachloride, adding iron, ferric chloride, or a mixture thereof, introducing chlorine while excluding light at a temperature in the range 30-90 DEG C. until the theoretical amount of hydrogen chloride has been evolved and separating tetrachloroxylene. This product is dissolved in a solvent and chlorine is introduced while under the influence of light and in the absence of iron catalyst at a temperature in the range 30-90 DEG C. until the theoretical amount of hydrogen chloride, for replacement of two hydrogens by chlorine has been evolved and the tetrachloroxylylene dichloride is separated. Detailed examples are given.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18888162A | 1962-04-19 | 1962-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB970024A true GB970024A (en) | 1964-09-16 |
Family
ID=22694950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14158/63A Expired GB970024A (en) | 1962-04-19 | 1963-04-09 | Preparation of tetrachloroxylylenediamines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB970024A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0099622A1 (en) * | 1982-05-27 | 1984-02-01 | Imperial Chemical Industries Plc | Process for the hydrogenation of perhalogenated terephthalonitriles to amines, 2,3,5,6-tetrafluoroxylylene diamine and salts thereof |
-
1963
- 1963-04-09 GB GB14158/63A patent/GB970024A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0099622A1 (en) * | 1982-05-27 | 1984-02-01 | Imperial Chemical Industries Plc | Process for the hydrogenation of perhalogenated terephthalonitriles to amines, 2,3,5,6-tetrafluoroxylylene diamine and salts thereof |
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