US546165A - Signors to the badische anilin and soda fabrik - Google Patents
Signors to the badische anilin and soda fabrik Download PDFInfo
- Publication number
- US546165A US546165A US546165DA US546165A US 546165 A US546165 A US 546165A US 546165D A US546165D A US 546165DA US 546165 A US546165 A US 546165A
- Authority
- US
- United States
- Prior art keywords
- acid
- signors
- badische anilin
- soda fabrik
- soda
- 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title description 4
- 239000002253 acid Substances 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- COHYTHOBJLSHDF-BUHFOSPRSA-N Indigo dye Chemical compound N\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-BUHFOSPRSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- VIFKLIUAPGUEBV-UHFFFAOYSA-N 2-(3-hydroxy-1H-indol-2-yl)-1H-indol-3-ol Chemical compound N1C2=CC=CC=C2C(O)=C1C1=C(O)C2=CC=CC=C2N1 VIFKLIUAPGUEBV-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- -1 phenyl glycocoll Chemical compound 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WGSLWEXCQQBACX-UHFFFAOYSA-N Chlorin Chemical compound C=1C(C=C2)=NC2=CC(C=C2)=NC2=CC(C=C2)=NC2=CC2=NC=1CC2 WGSLWEXCQQBACX-UHFFFAOYSA-N 0.000 description 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N Indigo Blue Chemical compound N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 2
- YEQRASMGLPZYDE-UHFFFAOYSA-N Indoxyl Chemical group C1=CC=C[C]2C(O)=CN=C21 YEQRASMGLPZYDE-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N Silver nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium monoxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001376 precipitating Effects 0.000 description 2
- 230000000630 rising Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
Definitions
- Our invention relates to the manufacture soda, which must also be as free from water of a new commercial product suited for use in as possible. Grind these two ingredients to- 20 printing indigo-blue shades on textile fabrics. gether, so that they become thoroughly mixed,
- cipitate Filter and wash with ice-cold water. In the moist state the acid is unstable, but becomes more stable after drying. Drying must be effected at a moderate heat (not above 50 centigrade) by spreading the material overa large surface. It is advantageous, but not necessary, to exclude the oxygen of the atmosphere.
- Our new commercial product is a gray powder but slightly soluble in cold water, soluble It is readily soluble in alkaline water, and the solution turns blue from formation of indigotin on exposure to the action of the atmospheric oxygen.
- the old indoxylic acid described in literature has existed solely as a scientific curiosity, and from its costliness and difficulty of production could never be commercially manufactured.
Description
UNITED STATES PATENT EEicE.
RUDOLPH KN'IETSOH AND PAUL SEIDEL, OF LUDVVIGSHAFEN, GERMANY, AS- STGNORS TO THE BADISCHE ANILIN AND SODA FABRIK, OF SAME PLACE.
INDOXYLIC ACID AND PROCESS OF MAKiNG IT.
SPECIFICATION forming part of Letters Patent No. 546,165, dated September 10, 1895.
App 5185 May 17, 1895- Serial No. 549,709. (No specimens.) Patented in France November 12, 1894, No. 206,982 in Belgium November 17, 1894, No. 112,74'i; in Italy December 6, 1394, XXIX, 37,665, and LXXIII, 498, and in Austria Decamber 24, 3.5394 1%. 44/ 6,512.
'0 (632 whom, it may concern/.- white in ice-water and precipitating the in Be it known that we, RUDOLPH KNIETSCH, doxylic acid by the addition of sulfuric or hydoctor of philosophy,asubject of the King of droohloricacid or a stronger organic acid. Prussia, German Emperor, and PAUL SEIDEL, Indoxylic acid, as heretofore obtained by the 5 doctor of philosophy, 2. subject of the King of process of Baeyer, and as described in the Saxony, residing at Ludwigshafen-on-thetext-books, contains more or less combined Rhine, in the Kingdom of Bavaria and Emhaloid elements, as bromin or chlorin; but pire of Germany, have invented new and useindoxylic acid as obtained by our process is 5 5 ful Improvements in the Manufacture of a entirely free from haloid elements.
[0 New .lndoxylic Acid, (for which patents have The following example will serve to illusbeen obtained in France, No. 206,982, (certifitrate the manner in which our invention can eat daddition,) dated November 12, 1894:; in best be carried into practical effect. The Austria, i4. 6,512, dated December 24, 1894;; parts are by weight. in Belgium, No. 112,744., dated November 17, Example: Mix about ten (10) parts of so- 1 5 189%, and in Italy, XXIX, 37,-365,LXXHI,498, dium phenyl glycocoll ortho carboxylate, dated December 6, 1894,) of which the followwhich must be quite neutral and thoroughly ing is a specification. dried with about twenty (20) parts of caustic Our invention relates to the manufacture soda, which must also be as free from water of a new commercial product suited for use in as possible. Grind these two ingredients to- 20 printing indigo-blue shades on textile fabrics. gether, so that they become thoroughly mixed,
In the Letters Patent No. 534,560, granted to and spread the fine powder so obtained in a Karl lleumanmthere is described the producthin layer. Then heat uniformly to a temtion of a new artificial indigo-white from perature of about two hundred and forty to phenyl-glycocoll-orthocarboxylic acid by two hundred and sixtyfive degrees centi- 2 treating with alkali. This is described as grade, (24.0-265G.) Throughout the operaconsisting of an intimate combination or mixtion the atmospheric air must be excluded as ture of unaltered alkali or alkaline earth with far as conveniently possible. This can be a body having the nature ofaleuco compound done, for example, by conducting the operaand with other products of the reaction. We tion in an atmosphere of an indifferent gas,
30 have found that the nature of this contained such as nitrogen, hydrogen, or the like. As leuco body varies according to the conditions the mass does not melt, the period of heating under which the reaction is effected, and that depends upon the thickness of the layer. In usually the leuco body is a mixture of ingenerah'from half an hour to one hours heatdoxyl and an indoxylie acid in the form of aling after the temperature mentioned is at- 3 5 kaline salt. We have discovered modificatained, is requisite. Allow the mass to cool. tions of the process for treating the phenyl- It should then possess a uniform lemon-yelglycocoll-ortho-carboxylic acid with alkalies low color throughout. The presence of a whereby it is possible with certainty to prowhitish. mass in the interior indicates that duce an artificial indigo-white containing inthe reaction is not complete and the heat must 4c doxylic acid only, to the practical exclusion of be maintained longer. Next grind about fifty indoxyl. This is effected by the use of caus- (50) parts of the artificial indigdwhite so obtic soda in the treatment of the phenyl-glycotained to powder and add it to a mixture of coll-ortho-carboxylic acid and at a temperaabout four hundred (400) parts of ice and go ture rising to about 240 to 265 centigrade. about one hundred and seventy -five- 45 From this artificial indigo-white we prepare part-s of dilute sulfuric acid containing about and isolate our new indoxylic acid. This is twenty-two per cent. (22%) real acid (H 80 effected by dissolving the artificial indigo- The indoxylic acid separates out as a prein alcohol and ether.
cipitate. Filter and wash with ice-cold water. In the moist state the acid is unstable, but becomes more stable after drying. Drying must be effected at a moderate heat (not above 50 centigrade) by spreading the material overa large surface. It is advantageous, but not necessary, to exclude the oxygen of the atmosphere.
Our new commercial product is a gray powder but slightly soluble in cold water, soluble It is readily soluble in alkaline water, and the solution turns blue from formation of indigotin on exposure to the action of the atmospheric oxygen.
This new product diifers from the substance heretofore known as indoxylic acid, and described as such, in the fact that it is 00111- pletely free from combined halogen, as can be seen by oxidizingto indigotin in alkaline solution, filtering off the indigotin, washing and testing the indigotin for halogens in the usual way'for instance, by treating with caustic lime, dissolving in nitric acid and testing for the haloid elements by means of nitrate of silver. The old indoxylic acid described in literature has existed solely as a scientific curiosity, and from its costliness and difficulty of production could never be commercially manufactured.
. Now, what we claim is 1. Asanew product theindoxylic acid which can be produced by the reaction of phenylglycocoll-ortho-carboxylic acid with caustic soda, and which is a gray powder but slightly soluble in cold water, soluble in alcohol and treating phenyl glycocoll ortho carboxylic acid with caustic soda at about240 to 265 centigrade, then treating the melt with ice cold dilute acid, then filtering and washing the precipitate, substantially as described.
In testimony whereof we have hereunto set our hands in the presence of two subscribing witnesses.
RUDOLPH KNIETSCH. PAUL SEIDEL.
\Vitnesses:
ERNEST F. EHRHARDT. ADOLPH RENTLINGER.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US546165A true US546165A (en) | 1895-09-10 |
Family
ID=2614909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US546165D Expired - Lifetime US546165A (en) | Signors to the badische anilin and soda fabrik |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US546165A (en) |
-
0
- US US546165D patent/US546165A/en not_active Expired - Lifetime
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