DE103683C - - Google Patents
Info
- Publication number
- DE103683C DE103683C DENDAT103683D DE103683DA DE103683C DE 103683 C DE103683 C DE 103683C DE NDAT103683 D DENDAT103683 D DE NDAT103683D DE 103683D A DE103683D A DE 103683DA DE 103683 C DE103683 C DE 103683C
- Authority
- DE
- Germany
- Prior art keywords
- triamidobenzene
- hydrochloric acid
- vol
- water
- trimethyl
- 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 12
- 229960001553 Phloroglucinol Drugs 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- -1 tetramethyl phloroglucine Chemical compound 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- MNBSXKSWDLYJHN-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3,5-triol Chemical compound CC1=C(O)C(C)=C(O)C(C)=C1O MNBSXKSWDLYJHN-UHFFFAOYSA-N 0.000 description 2
- XIRABDOOVRWLFU-UHFFFAOYSA-N 2,4-dimethylbenzene-1,3,5-triol Chemical compound CC1=C(O)C=C(O)C(C)=C1O XIRABDOOVRWLFU-UHFFFAOYSA-N 0.000 description 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241000218657 Picea Species 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N Silver nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229940030049 trimethylphloroglucinol Drugs 0.000 description 2
- YVJCXMCIFPUNDO-UHFFFAOYSA-N 1,3,5-trimethyl-2,4,6-trinitrobenzene Chemical group CC1=C([N+]([O-])=O)C(C)=C([N+]([O-])=O)C(C)=C1[N+]([O-])=O YVJCXMCIFPUNDO-UHFFFAOYSA-N 0.000 description 1
- BPHYZRNTQNPLFI-UHFFFAOYSA-N 2,4,6-trihydroxytoluene Chemical compound CC1=C(O)C=C(O)C=C1O BPHYZRNTQNPLFI-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 102100013068 CDCA4 Human genes 0.000 description 1
- 101700022879 CDCA4 Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 206010039509 Scab Diseases 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical group I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- UATJOMSPNYCXIX-UHFFFAOYSA-N symmetric Trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UATJOMSPNYCXIX-UHFFFAOYSA-N 0.000 description 1
- 239000000015 trinitrotoluene Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 239000008096 xylene 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
- C07C37/01—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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 12: Chemische Verfahren und Apparate.CLASS 12: Chemical processes and apparatus.
Zusatz zum Patente Λί 102358 vom 28. Dezember 1897.Addendum to patent Λί 102358 of December 28, 1897.
Patentirt im Deutschen Reiche vom 21. Mai 1898 ab. Längste Dauer: 27. Dezember 1912.Patented in the German Empire on May 21, 1898. Longest duration: December 27, 1912.
Homologe des Phloroglucins sind zur Zeit bis auf das Trimethylphloroglucin, welches in sehr geringer Menge bei der Einwirkung von Jodmethyl und Kali auf das Phloroglucin von O. Margulies (Monatshefte 9, S. 1046) neben Pentamethyl- und bisecundärem Tetramethylphloroglucin erhalten wurde, nicht bekannt.Homologues of phloroglucine are currently except for trimethylphloroglucine, which in very small amount in the action of iodomethyl and potash on the phloroglucinol of O. Margulies (MONTHS 9, p. 1046) in addition to pentamethyl and bisecondary tetramethyl phloroglucine not known.
Es wurde nun gefunden, dafs sich Homologe des Phloroglucins in sehr einfacher Weise und fast quantitativ gewinnen lassen, wenn man nach idem Verfahren des Patentes Nr. 102358 die Salze des leicht zugänglichen i-Methyl-2 · 4 · 6-triamidobenzols, des 1 · 3 -Dimethyl-2 ■ 4 · 6-triamidobenzols und des 1-3-5 -Trimethyl - 2 · 4 · 6 - triamidobenzols mit Wasser einige Zeit auf ioo° C. erhitzt. Dasselbe-Resultat wird in verhältnifsmäfsig längerer Zeit erzielt, wenn man die Einwirkungstemperatur erniedrigt. Bei hoher Temperatur oder bei Gegenwart von freien Mineralsäuren werden die Homologen des Phloroglucins ihrer Zersetzlichkeit wegen nicht gebildet.It has now been found that homologues of phloroglucinol can be obtained in a very simple manner can be obtained almost quantitatively if one follows the procedure of patent no. 102358 the salts of the easily accessible i-methyl-2 · 4 · 6-triamidobenzene, 1 · 3-dimethyl-2 ■ 4 · 6-triamidobenzene and 1-3-5 -trimethyl - 2 · 4 · 6 - triamidobenzene heated with water to 100 ° C. for some time. Same result is achieved in a relatively longer time if the temperature of action is taken humiliated. Be at high temperature or in the presence of free mineral acids the homologues of phloroglucinol are not formed because of their decomposition.
Die Methyltriamidobenzole werden nach der bekannten Methode aus den betreffenden Trinitroproducten durch Reduction mit Zinn und Salzsäure gewonnen.The methyltriamidobenzenes are prepared from the trinitro products in question by the known method obtained by reduction with tin and hydrochloric acid.
Das Triamidotoluol wird aus dem käuflichen 2 -4 ■ 6-Trinitrotoluol (Hepp, Annalen 215,344; Griesheim, Berichte der deutschen ehem. Gesellschaft, Bd. 28, R. 125, Patent Nr. 77559) dargestellt. Dasselbe wurde von Claus & Becker (Berichte der. deutschen ehem. Gesellschaft, Bd. 16, S. 1596) in symmetrisches Trinitrobenzol übergeführt und ist dadurch als 2 ■ 4 · 6-Trinitro-1 - Methylbenzol charakterisirt. In Bezug auf die näheren Einzelheiten der Darstellung des 2 · 4 ■ 6-Triamidomethylbenzols wird auf die Abhandlung über das Methylphloroglucin von H. W ei del (Monatshefte, Bd. 19, S. 223) verwiesen.The triamidotoluene is made from the commercially available 2 -4 ■ 6-trinitrotoluene (Hepp, Annalen 215,344; Griesheim, Reports of the former German Society, Vol. 28, R. 125, Patent No. 77559). The same was done by Claus & Becker (reports of the former German society, vol. 16, p. 1596) in symmetrical Converted trinitrobenzene and is thus as 2 ■ 4 · 6-trinitro-1-methylbenzene characterized. With regard to the further details of the representation of the 2 · 4 · 6-triamidomethylbenzene reference is made to the treatise on methylphloroglucine by H. W ei del (monthly books, Vol. 19, p. 223).
Die Darstellung des 1 · 3-Dimethyl-2 · 4 ■ 6-triamidobenzols wurde nach den Angaben einerseits von Grevingk (Berichte der deutschen ehem. Gesellschaft, Bd. 17, S. 2427), andererseits von Luhmann (Annalen, Bd. 144, S. 277) durchgeführt und sind die Eigenschaften dieses Körpers in den angegebenen Abhandlungen beschrieben.The representation of 1 · 3-dimethyl-2 · 4 · 6-triamidobenzene was according to the information on the one hand by Grevingk (reports of the German former Society, vol. 17, p. 2427), on the other hand by Luhmann (Annalen, vol. 144, p. 277) and the properties of this body are given in the treatises given described.
Hinsichtlich des 1-3-5 -Triamido-2 -4-6-trimethylbenzols mufs bemerkt werden,' dafs die Angaben Ladenburg's (Annalen, Bd. 179, S. 176), dafs bei der Reduction des 1-3- 5-Trinitro-2 · 4 · 6-trimethylbenzols mit Zinn und Salzsäure theilweise Rücksubstitution und Bildung von ι ■ 3 - Diamido - 2 · 4 · 6 - trimethylbenzol stattfindet, den thatsächlichen. Verhältnissen nicht entsprechen, sondern -dafs, wie H. Weidel und F.Wenzel (Monatshefteig, 250 u. f.) nachgewiesen haben, in regelrechter Weise aus dem Trinitromesitylen die Bildung des 1-3-5 -Triamido - 2 ■ 4 · 6 - trimethylbenzols stattfindet, und sind die Eigenschaften dieser Verbindung in der genannten Abhandlung genau beschrieben.With regard to the 1-3-5 -Triamido-2 -4-6-trimethylbenzene It must be noted that Ladenburg's statements (Annalen, Vol. 179, P. 176), that in the reduction of 1-3-5-trinitro-2 · 4 · 6-trimethylbenzene with tin and hydrochloric acid partly back substitution and formation of ι ■ 3 - diamido - 2 · 4 · 6 - trimethylbenzene takes place, the actual. Do not correspond to the circumstances, but rather -dafs, how H. Weidel and F. Wenzel (monthly leaflet, 250 and f.) Have shown that trinitromesitylene is formed in a proper way des 1-3-5 -Triamido - 2 · 4 · 6 - trimethylbenzene takes place, and are the properties of this compound in the cited treatise exactly described.
(2. Auflage, alisgegeben am 26. Oktober 1899.)(2nd edition, published October 26, 1899.)
A. Methylphloroglucin ( ι-Methyls'4· 6-trioxybenzol). 10 kg salzsaures ι-Methyl-2 · 4 · 6-triamidobenzol werden in 1 50 1 Wasser gelöst und 8 bis 10 Stunden unter Luftausschlufs (zweckmäfsig im Kohlensäurestrom) unter Rückflufs gekocht. Die auf ca. 30 1 concentrate Flüssigkeit wird mit Amylalkohol ausgeschüttelt. Der Alkohol nimmt das Methylphloroglucin quantitativ auf. Nach dem Abblasen des Amylalkohols mit Wasserdampf wird die wässerige Lösung des Methylphloroglucins mit Bleiessig partiell gefällt, um die färbenden Nebenproducte zu entfernen. Die nach dem Ausfällen des Bleies mit Schwefelwasserstoff erhaltene, fast farblose Lösung liefert nach entsprechender Concentration im Vacuum das Methylphloroglucin in reiner Form.A. Methylphloroglucin (ι-Methyls'4 · 6-trioxybenzene). 10 kg of hydrochloric acid ι-methyl-2 · 4 · 6-triamidobenzene are dissolved in 1 50 1 water and 8 to 10 hours with exclusion of air Boiled under reflux (expediently in a stream of carbonic acid). The on approx. 30 1 concentrate liquid is shaken out with amyl alcohol. The alcohol takes the methylphloroglucine quantitatively. After blowing off the amyl alcohol with steam, the aqueous solution of methylphloroglucine becomes Partially precipitated with lead vinegar to remove the coloring by-products. the almost colorless solution obtained after the lead has been precipitated with hydrogen sulphide delivers the methylphloroglucinol in pure form after the appropriate concentration in a vacuum.
Dasselbe bildet in Wasser leicht lösliche, zu Krusten verwachsene Nadeln, welche mit Eisenchlorid eine violette Farbreaction geben und auch eine der des Phloroglucins ähnliche Fichtenspahnreaction zeigen. Das Methylphloroglucin schmilzt zwischen 214 und 216° C. Es bildet bei Behandlung mit Alkohol und Salzsäure Mono- und Diäther und läfst sich mit Aldehyden, Aminen und Azoverbindungen zu gefärbten Producten condensiren.It forms needles which are easily soluble in water and which have grown together to form crusts, which with ferric chloride give a violet color reaction, and also one similar to that of phloroglucinol Show spruce tooth reaction. The methyl phloroglucine melts between 214 and 216 ° C. When treated with alcohol and hydrochloric acid, it forms mono- and dieters and dissolves condense with aldehydes, amines and azo compounds to give colored products.
B. Di methylphloroglucin (1 · 3 -Dimethyl-2 · 4 ■ 6-trioxybenzol). 10 kg salzsaures ι · 3-Dimethyl - 2 ■ 4 · 6-triamidobenzol, nach dem Verfahren von Grevingk (Berichte der deutschen ehem. Gesellschaft, Bd. 17, S. 2424) dargestellt, werden in 1 50 1 Wasser gelöst und 8 bis 10 Stunden unter Luftausschlufs unter Rückflufs gekocht.B. Dimethylphloroglucinol (1 x 3 -dimethyl-2 · 4 · 6-trioxybenzene). 10 kg of hydrochloric acid ι · 3-dimethyl - 2 · 4 · 6-triamidobenzene, according to the proceedings of Grevingk (reports of the former German society, vol. 17, p. 2424) shown, are dissolved in 1 50 1 water and 8 to 10 hours under the exclusion of air Boiled under reflux.
Die auf ca. 30 1 concen-The concen-
trirte Flüssigkeit wird mit Aether ausgeschüttelt. Aether nimmt das Dimethylphloroglucin leicht auf und hinterläfst es beim Abdampfen nahezu rein. Die Rohausscheidung wird zur weiteren Reinigung wiederholt aus Xylol umkrystallisirt. Aus diesem Lösungsmittel scheidet sich das Dimethylphloroglucin in prächtigen Krystallnadeln ab, die den Schmelzpunkt 1630C. zeigen. Sie geben in wässeriger Lösung mit Eisenchlorid eine roth violette Farbreaction und bringen gleich dem Phloroglucin eineFichtenspahnreaction hervor, die aber viel intensiver ist und einen blauvioletten Farbenton zeigt. Aus Wasser krystallisirt das Dimethylphloroglucin mit 2 Mol. Krystallwasser. Es liefert bei Behandlung mit Alkoholen und Salzsäure nur Monoäther und ist gegenüber Aldehyden, Phenolen, Aminen und Azoverbindungen sehr reactionsfähig.trapped liquid is shaken out with ether. Ether takes up the dimethylphloroglucine easily and leaves it almost pure when it evaporates. The crude precipitate is repeatedly recrystallized from xylene for further purification. For this solvent, the Dimethylphloroglucin separates gorgeous in crystalline needles which show the melting point of 163 0 C.. In an aqueous solution with ferric chloride they give a red-violet color reaction and, like phloroglucine, produce a spruce-tooth reaction, which, however, is much more intense and shows a blue-violet hue. Dimethylphloroglucinol crystallizes from water with 2 mol. Of crystalline water. When treated with alcohols and hydrochloric acid, it delivers only monoethers and is very reactive towards aldehydes, phenols, amines and azo compounds.
C. Tr i m e t hy 1 ρ h 1 ο r ο g 1 u c i η (1-3-5-Trimethyl - 2 · 4 · 6 - trioxybenzol). Das 1-3-5-Trimethyl-2 -4 · 6-trinitrobenzol liefert entgegen den Angaben Ladenburg's (Annalen, Bd. 179, S. 176) bei der Reduction mitZinn und Salzsäure ein 1-3-5 -Trimethyl-2 · 4 · 6-triamidobenzolchlorhydrat, welches bei der Hydrolyse glatt Trimethylphloroglucin bildet.C. Tr i m e t hy 1 ρ h 1 ο r ο g 1 u c i η (1-3-5-trimethyl - 2 x 4 x 6-trioxybenzene). The 1-3-5-trimethyl-2 -4 6-trinitrobenzene delivers contrary to the statements of Ladenburg's (Annalen, Vol. 179, P. 176) in the reduction with tin and hydrochloric acid a 1-3-5 -trimethyl-2 · 4 · 6-triamidobenzene chlorohydrate, which on hydrolysis smoothly forms trimethylphloroglucine.
Zur Darstellung desselben werden 10 kg salzsaures 1-3-5 -Trimethyl-2 ■ 4 · 6-triamidobenzol in 150 1 Wasser gelöst und 8 bis 10 Stunden bei Luftabschlufs unter Rückflufs gekocht. Die auf ca. 25 1 concentrirte Flüssigkeit scheidet nach dem Erkalten die Hauptmenge des Trimethylphloroglucins in licht braungelb gefärbten Blättchen ab. Der in der Mutterlauge verbleibende Rest kann durch Ausschütteln mit Aether gewonnen werden. Die Reindarstellung gelingt durch Umkrystallisiren der Rohausscheidung aus Eisessig. Das Trimethylphloroglucin bildet farblose Nadeln. Die wässerige Lösung desselben wird durch Eisenchlorid erst rothviolett, dann braunviolett gefärbt und giebt endlich mit überschüssigem Eisenchlorid eine grauviolette Fällung. Silbernitrat wird reducirt. Es giebt keine Fichtenspahnreaction und zeigt den Schmelzpunkt 1840 C. Auch das Trimethylphloroglucin, sowie dessen Monoäther, der bei der Einwirkung von Alkohol und Salzsäure entsteht, sind gegenüber Aldehyden, Phenolen, Aminen und Azoverbindungen reactionsfähig.To prepare the same, 10 kg of hydrochloric acid 1-3-5-trimethyl-2 · 4 · 6-triamidobenzene are dissolved in 150 l of water and refluxed for 8 to 10 hours with the air being shut off. The liquid, concentrated to about 25 liters, after cooling, separates most of the trimethylphloroglucinol in light brown-yellow colored leaflets. The remainder in the mother liquor can be extracted by shaking with ether. The pure representation is achieved by recrystallizing the raw precipitate from glacial acetic acid. The trimethylphloroglucine forms colorless needles. The aqueous solution of the same is colored first red-violet, then brown-violet by iron chloride, and finally gives a gray-violet precipitate with excess iron chloride. Silver nitrate is reduced. There is no spruce Spahn Reaction and shows the melting point of 184 0 C. Also, the Trimethylphloroglucinol, and its mono ether, which formed by the action of alcohol and hydrochloric acid are preferred to aldehydes, phenols, amines, and azo compounds reactionsfähig.
In den vorstehenden Beispielen können an Stelle der salzsauren Salze andere mineralsaure Salze verwendet werden. Die angegebene Menge des Wassers kann in weiten Grenzen variirt und das Erhitzen sowohl in offenen wie in geschlossenen Gefäfsen vorgenommen werden.In the above examples, other mineral acids can be used instead of the hydrochloric acid salts Salts are used. The stated amount of water can vary within wide limits and heating can be carried out in both open and closed vessels.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE103683C true DE103683C (en) |
Family
ID=374150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT103683D Active DE103683C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE103683C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2517496A (en) * | 1945-02-02 | 1950-08-01 | Edwal Lab Inc | Preparation of symmetrical monoaminodihydroxytoluene |
-
0
- DE DENDAT103683D patent/DE103683C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2517496A (en) * | 1945-02-02 | 1950-08-01 | Edwal Lab Inc | Preparation of symmetrical monoaminodihydroxytoluene |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1182671B (en) | Process for the production of new ethers and thioethers of panthenol | |
| DE103683C (en) | ||
| DE2211436A1 (en) | Process for the preparation of 2-alkoxy-5-methoxybenzaldehydes | |
| DE102358C (en) | ||
| DE931652C (en) | Process for the preparation of 5-cycloalkylidene-pseudothiohydantoins | |
| DE444014C (en) | Process for the preparation of thiuram disulfides | |
| DE1292142B (en) | Process for the preparation of ª ‡ -Picolinaniliden | |
| DE910646C (en) | Process for the preparation of mineral acid salts of mono- or polysubstituted isothioureas | |
| DE433099C (en) | Process for the preparation of oxindole-3-acetic acids and their homologues which are halogen-substituted in the aromatic nucleus | |
| DE838690C (en) | Azo components for diazotype blueprints | |
| DE650706C (en) | Process for the conversion of carboxylic acids into their next higher homologues or their derivatives | |
| DE814596C (en) | Process for the production of aralkyl mercapto fatty acids | |
| DE1644636C (en) | Acid, diamino-substituted from di arylamine derived Tnarylmethanfarben substances | |
| DE892897C (en) | Process for the preparation of pyrroles | |
| DE557813C (en) | Process for the preparation of piperidine ketones and keto alcohols | |
| DE515468C (en) | Process for the preparation of ª ‰ -Naphthylaminophenoxyfettsaeuren | |
| DE894994C (en) | Process for the production of aliphatic mercury ketone compounds | |
| DE536996C (en) | Process for the production of arsic acids and stibic acids containing sulfur | |
| DE877614C (en) | Process for the production of clusters of p-aminosalicylic acid | |
| DE1242603B (en) | Process for the preparation of 5-hydroxy-5-aminoalkyl-di-benzo- [a, d] -cycloheptanes | |
| DE279549C (en) | ||
| DE182217C (en) | ||
| DE1468344A1 (en) | UNSATABLED ACIDS AND THE METHOD OF MANUFACTURING THEREOF | |
| DE196605C (en) | ||
| DE85568C (en) |