US1404055A - Purification of crude anthracene - Google Patents
Purification of crude anthracene Download PDFInfo
- Publication number
- US1404055A US1404055A US404145A US40414520A US1404055A US 1404055 A US1404055 A US 1404055A US 404145 A US404145 A US 404145A US 40414520 A US40414520 A US 40414520A US 1404055 A US1404055 A US 1404055A
- Authority
- US
- United States
- Prior art keywords
- anthracene
- carbazole
- potassium
- purification
- crude anthracene
- 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 - Lifetime
Links
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title description 52
- 238000000746 purification Methods 0.000 title description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 37
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 28
- 235000011118 potassium hydroxide Nutrition 0.000 description 12
- 238000000034 method Methods 0.000 description 8
- WFTICIXFISZPCW-UHFFFAOYSA-N 9h-carbazole;potassium Chemical group [K].C1=CC=C2C3=CC=CC=C3NC2=C1 WFTICIXFISZPCW-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 241000985284 Leuciscus idus Species 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14833—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds
- C07C7/1485—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds oxides; hydroxides; salts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Definitions
- German Patent No. 111,359 recommends the temperature of 260 degrees 0.; in the process of German Patent No. 178,764 the anthracene is distilled off from the carbazolepotash melt in a vacuum, which likewise requires a temperature of far above 200 degrees C.
- Beilstein, vol. IV, p. 390 gives the temperature at which carbazole potassium forms from carbazole and potassium hydrate as 220 to 240 degrees C.
- the invention has for its basis the discovery that the theoretical yield of carbazole potassium from carbazole and potassium hydrate can be ob tained at much lower temperatures, if the carbazole be mixed with potassium hydrate in the presence of a solvent for carbazole and anthracene, for example' hydrocarbons, and boiling until carbazole potassium is formed, water being meanwhile distilled off. In this manner it is possible to produce carbazole potassium even at the boiling point of toluol. On the basis of this discovery, the carbazole can be separated from the crude anthracene in the theoretical quantity.
- the water formed in the aforesaid reaction may be advantageously distilled off mixed with the solvent or larger quantities of caustic potash may be employed, in which Specification of Letters Patent.
- Crude anthracene containa ing 53.4 per cent of anthracene is purifiedby dissolving it in na htha of a boiling point of 145 degrees. emi-purified anthracene containing 70 per cent of anthracene is obtained.
- the hot anthracene solution is drawn off and after cooling there is obtained an anthracene which when drawn off and separated from the naphtha has a degree of purity far above 90 per cent and contains no trace of carbazole.
- the carbazole-potassium is freed from the naphtha by means of steam and simultaneously decomposed into carbazole and potassium hydrate. In this manner it is possible, at temperatures which can be easily reached by indirect steam heating, to separate from each other and obtain anthracene and carbazole in most without loss of purity.
- Example 2 150 parts by weight of crude anthracene containing about 50 per cent of anthracene are dissolved bymeans of coal tar naphtha of a boiling point of 130 degrees C., and the paste obtained which cona very simple manner, aland of an excellent degree tains about 70 per cent of pure anthracene, is heated to 120 degrees C. with 200 to 300 part by weight ofnaphtha and 60 arts by weight of 80 per cent caustic potash i the mixture being meanwhile well'stirred.
- a process for the separation'of anthracene and carbazole consisting in dissolving the mixture in a neutral solvent, adding caustic potash, and removing the water produced during the reaction in order to avoid decomposition of the carbazole-potassium.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT87645D AT87645B (de) | 1916-10-30 | 1916-10-30 | Verfahren zur Reinigung von Rohanthracen. |
| AT87648D AT87648B (de) | 1916-10-30 | 1917-03-31 | Verfahren zum Reinigen von Rohanthracen. |
| FR519211A FR519211A (fr) | 1916-10-30 | 1920-06-30 | Procédé d'épuration de l'anthracène brut |
| US404145A US1404055A (en) | 1916-10-30 | 1920-08-17 | Purification of crude anthracene |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT87645T | 1916-10-30 | ||
| US404145A US1404055A (en) | 1916-10-30 | 1920-08-17 | Purification of crude anthracene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1404055A true US1404055A (en) | 1922-01-17 |
Family
ID=23598352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US404145A Expired - Lifetime US1404055A (en) | 1916-10-30 | 1920-08-17 | Purification of crude anthracene |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US1404055A (de) |
| AT (2) | AT87645B (de) |
| FR (1) | FR519211A (de) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2419969A (en) * | 1943-09-04 | 1947-05-06 | Koppers Co Inc | Process of recovering and purifying carbazole and anthracene |
| US2464811A (en) * | 1944-06-20 | 1949-03-22 | Koppers Co Inc | Purification of carbazole |
| US2464833A (en) * | 1945-08-28 | 1949-03-22 | Koppers Co Inc | Purification of carbazole |
-
1916
- 1916-10-30 AT AT87645D patent/AT87645B/de active
-
1917
- 1917-03-31 AT AT87648D patent/AT87648B/de active
-
1920
- 1920-06-30 FR FR519211A patent/FR519211A/fr not_active Expired
- 1920-08-17 US US404145A patent/US1404055A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2419969A (en) * | 1943-09-04 | 1947-05-06 | Koppers Co Inc | Process of recovering and purifying carbazole and anthracene |
| US2464811A (en) * | 1944-06-20 | 1949-03-22 | Koppers Co Inc | Purification of carbazole |
| US2464833A (en) * | 1945-08-28 | 1949-03-22 | Koppers Co Inc | Purification of carbazole |
Also Published As
| Publication number | Publication date |
|---|---|
| AT87645B (de) | 1922-03-10 |
| FR519211A (fr) | 1921-06-07 |
| AT87648B (de) | 1922-03-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2376008A (en) | Production of lutidine-urea compounds | |
| US1841768A (en) | Chlorinated and brominated ethine carbinols | |
| US1404055A (en) | Purification of crude anthracene | |
| US2273922A (en) | Fluorine-containing compounds of the naphthalene series | |
| US256400A (en) | James h | |
| US2688631A (en) | Process for preparing dicyano stilbenes | |
| US2016784A (en) | Production of organic sulpho-halides | |
| US2347228A (en) | Method of producing anthracene | |
| US2216131A (en) | Process for the production of polynuclear carbon compounds | |
| US1548920A (en) | Manufacturing pure anthracene and pure carbazol | |
| US1397134A (en) | Making trichlorethylene | |
| US1045139A (en) | Process of making chlorinated hydrocarbons | |
| US2077548A (en) | Production of dinaphthylene oxide | |
| US1153054A (en) | Process of producing sulfids of phosphorus. | |
| US2114286A (en) | Method of purifying beta-phenylethyl alcohol | |
| US1766747A (en) | Process for manufacturing vic. trihalogenbenzenes | |
| US2007241A (en) | office | |
| US961915A (en) | Reduction products of commercial nitrobenzaldehyde. | |
| US2342794A (en) | Long-chain aliphatic isocyanides | |
| US1140747A (en) | 2.3-oxynaphthoic-acid derivative. | |
| US1869481A (en) | Process for producing pure anthracene | |
| US1086294A (en) | Bromodiethylacetylisocyanate. | |
| US2442547A (en) | Method of producing iminodiacetonitrile | |
| US782154A (en) | Preparation of theophyllin. | |
| US1747535A (en) | Aromatic diacidyl compound and process for preparing the same |