DE102358C - - Google Patents
Info
- Publication number
- DE102358C DE102358C DENDAT102358D DE102358DA DE102358C DE 102358 C DE102358 C DE 102358C DE NDAT102358 D DENDAT102358 D DE NDAT102358D DE 102358D A DE102358D A DE 102358DA DE 102358 C DE102358 C DE 102358C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- water
- triamidobenzoic
- hydrochloric acid
- triamidobenzene
- 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.)
- Active
Links
- QCDYQQDYXPDABM-UHFFFAOYSA-N Phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 229960001553 Phloroglucinol Drugs 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 208000001848 Dysentery Diseases 0.000 claims 1
- 101700076142 ERL1 Proteins 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- KAQBNBSMMVTKRN-UHFFFAOYSA-N 2,4,6-trinitrobenzoic acid Chemical compound OC(=O)C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KAQBNBSMMVTKRN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 240000000358 Viola adunca Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- FSDSKERRNURGGO-UHFFFAOYSA-N cyclohexane-1,3,5-triol Chemical compound OC1CC(O)CC(O)C1 FSDSKERRNURGGO-UHFFFAOYSA-N 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- -1 hydrochloric acid compound Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/045—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 12: Chemische Verfahren dnd Apparate.CLASS 12: Chemical processes and apparatus.
Patentirt im Deutschen Reiche vom 28. Dezember 1897 ab.Patented in the German Empire on December 28, 1897.
Die Umständlichkeit und Kostspieligkeit der bisherigen Darstellungsmethoden des Phloroglucins haben dessen technische Verwendung bis jetzt verhindert. In sehr einfacher Weise und fast quantitativ bildet sich diese Verbindung, wenn man Salze des leicht zugänglichen 1-3 ■ 5-Triamidobenzols oder der 1· 2-4- 6-Triamidobenzoesäure*) mit Wasser einige Zeit auf ioo° C. erhitzt. Ein gleiches Resultat wird in verhältnifsmäfsig längerer Zeit erzielt, wenn man die Einwirkungstemperatur erniedrigt. Der Austausch der TVi^-Gruppe durch OH durch Hydrolyse ist schon mehrfach beobachtet und auch technisch benutzt worden (s. Monatshefte der Chemie 14, S. 401 u. f.; 16,. S. 248 bis 249, Patentschriften Nr. 71494, 74644 und 74879, sowie ferner Ber. d. d. ehem. Ges. Bd. XXX, S. 2568). Obige Reactionen verlaufen mit Ausnahme der Bildung von Phloroglucin aus Phloramin bei Temperaturen von 160 bis 2oo° C, deren Anwendung auf das vorliegende Verfahren völlig unzulässig wäre, weil dabei das Phloroglucin in Condensationsproducte (Phloroglucit etc.) übergehen würde.The awkwardness and cost of the previous methods of preparation of phloroglucin have prevented its technical use up to now. This compound is formed in a very simple manner and almost quantitatively if salts of the easily accessible 1-3-5-triamidobenzene or 1 · 2-4- 6-triamidobenzoic acid *) are heated to 100 ° C. with water for some time. The same result is achieved in a relatively longer time if the temperature of action is lowered. The exchange of the TVi ^ group by OH by hydrolysis has already been observed several times and has also been used industrially (see monthly journals of Chemistry 14, p. 401 uf; 16 ,. pp. 248 to 249, patents nos. 71494, 74644 and 74879 , and also Ber. dd. former Ges. Vol. XXX, p. 2568). The above reactions, with the exception of the formation of phloroglucine from phloramine, take place at temperatures of 160 to 200 ° C, the application of which to the present process would be completely inadmissible because the phloroglucine would then be converted into condensation products (phloroglucitol, etc.).
*) Erhalten durch Reduction der von Tiemann & Judson, Ber. Ill, S. 224 beschriebenen Trinitrobenzoesäure. Sie bildet ein in Salzsäure schwer lösliches Zinndoppelsalz. Das hieraus durch Entfernen des Zinns mittels Schwefelwasserstoff erhältliche Chlorhydrat krystallisirt aus Wasser in durchsichtigen Prismen. Seine wässerige Lösung wird durch Bichromat blauviolett gefärbt. Bei der Einwirkung salpetriger Säure erhält man eine intensiv gelbe Lösung, deren Farbe durch Soda in violett umschlägt.*) Obtained through the reduction of Tiemann & Judson, Ber. Ill, p. 224 described trinitrobenzoic acid. It forms a tin double salt that is sparingly soluble in hydrochloric acid. That from this by removing Hydrochloride, obtainable from tin by means of hydrogen sulfide, crystallizes from water in transparent prisms. Its aqueous solution is colored blue-violet by dichromate. In the The action of nitrous acid produces an intensely yellow solution, the color of which is caused by soda in turns purple.
Nach den bisherigen, in der Literatur verzeichneten Angaben konnte daher erwartet werden, dafs sich aus dem 1 · 3 · 5-Triamidobenzol event, sämmtliche NH^-Reste abspalten lassen, dafs aber infolge der Reactionsbedingungen das Phloroglucin total verändert oder nur in minimalen Mengen entstehen würde.According to the information previously recorded in the literature, it could therefore be expected that all the NH3 residues could be split off from the 1 · 3 · 5-triamidobenzene event, but that the phloroglucine would be totally changed or only formed in minimal quantities as a result of the reaction conditions would.
10 kg salzsaures 1 · 3 ■ 5-Triamidobenzol oder eine entsprechende Menge der Salzsäureverbindung der ι · 2 · 4 · 6 -Triamidobenzoe'säure werden in 1 50 1 Wasser gelöst und 8 Stunden bei Luftabschlufs (zweckmä'fsig bei Gegenwart eines indifferenten Gases) unter Rückflufs gekocht. Die Flüssigkeit concentrirt man sodann auf 30 1 und läfst abkühlen. Das gebildete Phloroglucin scheidet sich zum gröfsten Theil ab und kann durch Umkrystallisiren gereinigt werden.10 kg hydrochloric acid 1 · 3 ■ 5-triamidobenzene or a corresponding amount of the hydrochloric acid compound of ι · 2 · 4 · 6 -triamidobenzoic acid are dissolved in 1 50 l of water and 8 hours in the absence of air (expediently in the presence an inert gas) boiled under reflux. The liquid is then concentrated to 30 l and allow to cool. Most of the phloroglucinine formed separates and can be purified by recrystallization.
In dem obigen Beispiel können an Stelle des salzsauren andere mineralsaure Salze des ι · 3 · 5-Triamidobenzols bezw. der 1-2-4-6-Triamidobenzoesäure verwendet werden. Die angegebene Menge des Wassers kann innerhalb ziemlich weiter Grenzen variirt und das Erhitzen sowohl in offenen als in geschlossenen Gefäfsen vorgenommen werden.In the above example, instead of the hydrochloric acid, other mineral acid salts of the ι · 3 · 5-Triamidobenzols respectively. of 1-2-4-6-triamidobenzoic acid be used. The amount of water given can vary within fairly wide limits, as can the heating can be carried out in both open and closed vessels.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102358C true DE102358C (en) |
Family
ID=372964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT102358D Active DE102358C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE102358C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2684383A (en) * | 1951-03-28 | 1954-07-20 | Ringwood Chemical Corp | Preparation of symmetrical triaminobenzene compounds |
| DE1195327B (en) * | 1963-03-22 | 1965-06-24 | Kalle Ag | Process for the preparation of symmetrical trihydroxybenzenes |
| FR2351076A1 (en) * | 1976-05-14 | 1977-12-09 | Akzo Nv | PROCESS FOR PREPARING THE PHLOROGLUCIN |
| US4296260A (en) * | 1978-09-18 | 1981-10-20 | Akzona Incorporated | Process for the preparation of phloroglucinol |
| US7217840B2 (en) | 2002-06-11 | 2007-05-15 | Phv Analytic | Method for preparing 1,3,5-triaminobenzene and hydrolyzing it into high-purity phloroglucinal |
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0
- DE DENDAT102358D patent/DE102358C/de active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2684383A (en) * | 1951-03-28 | 1954-07-20 | Ringwood Chemical Corp | Preparation of symmetrical triaminobenzene compounds |
| DE1195327B (en) * | 1963-03-22 | 1965-06-24 | Kalle Ag | Process for the preparation of symmetrical trihydroxybenzenes |
| FR2351076A1 (en) * | 1976-05-14 | 1977-12-09 | Akzo Nv | PROCESS FOR PREPARING THE PHLOROGLUCIN |
| US4296260A (en) * | 1978-09-18 | 1981-10-20 | Akzona Incorporated | Process for the preparation of phloroglucinol |
| US7217840B2 (en) | 2002-06-11 | 2007-05-15 | Phv Analytic | Method for preparing 1,3,5-triaminobenzene and hydrolyzing it into high-purity phloroglucinal |
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