GB701179A - An improved method of manufacturing 3-picoline - Google Patents
An improved method of manufacturing 3-picolineInfo
- Publication number
- GB701179A GB701179A GB20836/51A GB2083651A GB701179A GB 701179 A GB701179 A GB 701179A GB 20836/51 A GB20836/51 A GB 20836/51A GB 2083651 A GB2083651 A GB 2083651A GB 701179 A GB701179 A GB 701179A
- Authority
- GB
- United Kingdom
- Prior art keywords
- picoline
- chloride
- cuprous chloride
- cupric
- decomposed
- 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
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 title abstract 13
- 238000004519 manufacturing process Methods 0.000 title 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract 5
- 229960003280 cupric chloride Drugs 0.000 abstract 5
- 229940045803 cuprous chloride Drugs 0.000 abstract 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 4
- 239000002585 base Substances 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 238000001816 cooling Methods 0.000 abstract 3
- 239000002244 precipitate Substances 0.000 abstract 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 2
- 150000004699 copper complex Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 2
- 239000004291 sulphur dioxide Substances 0.000 abstract 2
- 229910052936 alkali metal sulfate Inorganic materials 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
Landscapes
- Pyridine Compounds (AREA)
Abstract
3-Picoline is separated from a mixture of pyridine bases contained in basic tar fractions boiling at 140-145 DEG C., by treating with cupric or cuprous chloride or with cupric chloride and a reducing agent such as sulphur dioxide or alkali metal sulphates whereupon the 3-picoline forms a crystalline precipitate of a copper complex from which the free base is obtained by steam distilling in the presence of an alkali such as sodium hydroxide. The cupric chloride may suitably be added as an aqueous solution. In a modification suitable for the purification of high percentage 3-picoline the crude base is added dropwise to solid cuprous chloride, the reaction mixture is heated until the cuprous chloride is dissolved and the crystalline precipitate produced by cooling is separated and decomposed. In examples (1) a mixture of pyridine bases is treated with aqueous cupric chloride and boiled and the copper complex which separates on cooling is decomposed by steam-distilling with aqueous alkali to give 3-picoline; (2) pyridine bases are separated as in (1) using cupric chloride and sulphur dioxide and (3) 95 per cent. pure 3-picoline is added to solid cuprous chloride and heated to dissolve the cuprous chloride and the precipitate which separates on cooling is decomposed to give 3-picoline.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS701179X | 1950-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB701179A true GB701179A (en) | 1953-12-16 |
Family
ID=5454928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20836/51A Expired GB701179A (en) | 1950-09-30 | 1951-09-04 | An improved method of manufacturing 3-picoline |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB701179A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2767187A (en) * | 1954-12-29 | 1956-10-16 | Pittsburgh Coke & Chemical Co | Isolation of gamma picoline |
| US2913323A (en) * | 1956-10-24 | 1959-11-17 | Monsanto Chemicals | Herbicidal method and composition employing bis(2-methyl-5-ethylpyridine) copper (ii) chloride |
-
1951
- 1951-09-04 GB GB20836/51A patent/GB701179A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2767187A (en) * | 1954-12-29 | 1956-10-16 | Pittsburgh Coke & Chemical Co | Isolation of gamma picoline |
| US2913323A (en) * | 1956-10-24 | 1959-11-17 | Monsanto Chemicals | Herbicidal method and composition employing bis(2-methyl-5-ethylpyridine) copper (ii) chloride |
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