US618167A - Alexander classen - Google Patents
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- Publication number
- US618167A US618167A US618167DA US618167A US 618167 A US618167 A US 618167A US 618167D A US618167D A US 618167DA US 618167 A US618167 A US 618167A
- Authority
- US
- United States
- Prior art keywords
- iodin
- compounds
- tetraiodophenolphtalein
- phenolphtalein
- solution
- 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
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- 150000001875 compounds Chemical class 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000243 solution Substances 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- KJFMBFZCATUALV-UHFFFAOYSA-N Phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 235000011121 sodium hydroxide Nutrition 0.000 description 14
- 210000004940 Nucleus Anatomy 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 235000011167 hydrochloric acid Nutrition 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 159000000000 sodium salts Chemical class 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 125000004429 atoms Chemical group 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 210000003932 Urinary Bladder Anatomy 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 208000003796 Chancre Diseases 0.000 description 2
- 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
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 210000003800 Pharynx Anatomy 0.000 description 2
- 235000015450 Tilia cordata Nutrition 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- -1 iodid Substances 0.000 description 2
- 238000006192 iodination reaction Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 150000002696 manganese Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 201000009240 nasopharyngitis Diseases 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000001376 precipitating Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
- C07D307/885—3,3-Diphenylphthalides
Definitions
- This invention relates to the production of the sodium salt of an iodin compound containing the iodin in the benzene nuclei of phenolphtalein.
- the phenolphtalein can be readily converted into iodin derivatives by solution in alkalies, addition of iodin and precipitation of the products by means of acids.
- the iodin compounds thus obtained ditfer from the iodin derivatives hitherto produced from the oxybodies by the fact that by the entrance of all the iodin bodies into the benzene nuclei the hydrogen atoms of the hydroxyl groups remain free and give the resulting compounds the character of strong acids.
- the iodin derivatives of aromatic oxy-bodies hitherto produced in alkaline solution are, Without any exception, insoluble in alkalies, and the reason of this insolubility consists in the presence of iodin oXyl-compounds.
- the iodin can be employed either dissolved in a solution of potassium iodid or in any other suitable solvent or it may be employed in the form of iodids with the addition of agents capable of liberating iodin-for instance, chlorid of lime, chlorin, bromin, or the like.
- Iodinchlorid or the combination of iodin, chlorid, and muriatic acid or the like agents, can be used in place of iodin for producing the iodin compounds from the said hydroxyl products or secondary amins or the like.
- the production of the iodin compounds hereinbefore defined is illustrated by the following examples. The parts are by weight.
- the moist precipitate is raised to a higher temperature, (about 100 centigrade,) it is converted into a white body-namely, tetraiodophenolphtalein-while the yellowishbrown body produced in the cold is to be considered as tetraiodophenolphtalein plus one molecule of water. It is purified by solution of the undried precipitate in chloroform and precipitation with ligroin, and after drying in racuo it is obtained as a yellow powder devoid of odor and is perfectly permanent in light and air. The analysis gives:
- the tetraiodophenolphtalein is insoluble in water and ligroin. In the other organic solvents, under heating, it is easily soluble, but with greater difiiculty in the cold. It is most readily taken up by warm chloroform. It is insoluble in acids; readily soluble in alkalies. It is distinguished by perfect absence of odor, and it is quite permanent when exposed to light and moisture.
- Electrolytz'cal production-3O grams phenolphtalein are dissolved in one hundred grams water containing thirty-five grams sodium hydrate. To this are added one hundred and forty grams potassium iodid in two hun dred grams water, and it is subjected to electrolysis for some hours with a current of about 1.5 amperes. The change of color shows the end of the reaction. It is then heated until the blue tint has changed into brownish yellow, and the tetraiodophenolphtalein is precipitated with hydrochloric acid.
- the tetraiodophenolphtalein is first dissolved in water containing the calculated quantity of sodium hydroxid, (one-tenth of the employed tetraiodophenolphtalein) and the solution is evaporated to dryness.
- the salt thus obtained represents, dried at 100, a blue powder very easily soluble in water with a blue color; with more difficulty in alcohol. It corresponds to the formula:
- the sodium salt here described is used as a sprinkling-powder in the case of purulent Per cent.
- aqueous solution In aqueous solution it is employed for moist bandages and tampons at a concentration of two per cent.
- a solution of two per cent For rinsing the bladder in bladder catarrh a solution of two per cent. has given Very excellent results.
- a solution of from 0.1 to 0.5 per cent. is employed for gargling and rinsing.
- the sodium salt is also used as first material in the production of various metallic salts of tetraiodophenolphtalein-as, for instance, aluminium, zinc, lead, iron, and manganese salts.
- the somy invention Ihave signed my name in pres-- dium salt of an iodin compound containing the enceof two subscribing witnesseses.
- iodin in the benzene nuclei of phenolphtalein the same being a dark-blue amorphous pow- ALEXANDER OLASSEN' 5 cler, nearly odorless and tasteless and readily Vitnesses:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
rvrrn STATES PATENT Orrrcn.
ALEXANDER CLASSEN, OF AIX-LA-OIIAPELLE, GERMANY.
SODIUM SALT OF lODlN COMPOUND.
SPECIFICATION forming part of Letters Patent No. 618,167, dated January 24, 1899. lApplication filed June 1, 1898. Serial No. 682,280 (No specimens.)
To all ll/71 0717) it Hwy 007L667:
Be it known that I, ALEXANDER CLASSEN, of the Technical High School of Aix-la-Ohapelle, a citizen of Germany, and a resident at Templergraben No.57, Aix-la-Ohapelle, in the Kingdom of Prussia, Germany, have invented new and useful Improvements in the Manufacture of New Iodin Compounds and the Resulting Products, (for which I have obtained the following Letters Patent in foreign countries: Great Britain, No. 12,987, dated July 4, 1894; Luxemburg, No. 2,221, dated January 18, 1895; Italy, Reg. Gen.,Vol. XXIX, No. 38,079, and Reg. Att.,Vol. LXXIV, No. 371, dated March 31, 1895; Norway, No. 4, 166, dated January 22, 1895, and No. 1,467, dated July 29, 1895; Portugal, No.1,958, dated September 19, 1895; Brazil, No. 1,916, dated September 3, 1895; British India, No. 610, dated February 23, 1895; Sweden, Nos. 7,132 and 7 ,131, dated January 25, 1895; Denmark, No. 7 67, dated October 2, 1895, and Germany, Nos. 85,929 and 85,930, dated May 26, 1895, No. 86,069, dated July 22, 1895, and No. 88,390, dated May 14, 189 6,) of which the following is a specification.
This invention relates to the production of the sodium salt of an iodin compound containing the iodin in the benzene nuclei of phenolphtalein.
In carrying my invention into effect I first produce tetraiodophenolphtalein, which is described and claimed in an application heretofore filed by me on 29th day of October, 1894:, Serial No. 527,113. I will, however, here first describe some of the processes for producing tetraiodophenolphtalein before proceeding with the description of the processes for producing the sodium salts thereof. Iodin derivatives of phenols have already been produced in great number. I have discovered that new iodin compounds are obtainable, which are also capable of pharmaceutical application, if the phenolphtalein is treatedin a suitable manner withiodin or substances yielding iodin.
According to my investigations the phenolphtalein can be readily converted into iodin derivatives by solution in alkalies, addition of iodin and precipitation of the products by means of acids. The iodin compounds thus obtained ditfer from the iodin derivatives hitherto produced from the oxybodies by the fact that by the entrance of all the iodin bodies into the benzene nuclei the hydrogen atoms of the hydroxyl groups remain free and give the resulting compounds the character of strong acids. The iodin derivatives of aromatic oxy-bodies hitherto produced in alkaline solution are, Without any exception, insoluble in alkalies, and the reason of this insolubility consists in the presence of iodin oXyl-compounds. The proof that in the case of the iodin derivatives of phenolphtalein all the iodin atoms are in the nuclei consists not only in their acid nature, but also in the tetrimetrical determination of the number of the hydroxyl groups, from which it resulted that in the case of the iodin compounds obtained their number is always equal to that of the original matters. Another proof of this position is their behavior in the presence of acetic anhydrid. lVhile it has been shown that the iodin compounds of phenolphtalein are converted by boiling for several hours on the reflux cooler with acetic anhydrid into corresponding (triaceto) compounds, which by boiling with soda-lye are reconverted into the original iodin compounds, the action of the acetic anhydrid on halogenoxyl compounds takes place in quite a different manner. Either the iodin contained in the hydroxyl groups is separated with the formation of an acetyl derivative, containing correspondingly less iodin atoms, or the iodin atoms are transposed into the nucleus. M oreover, all the halogen-oxyl compounds are completely insoluble in alkalies and show only little resistance. On the contrary, the iodin compounds of the phenolphtalein substituted in the nucleus can be treated with boiling soda-lye without decomposing them. The acid nature enables them, moreover, to form salts with light and heavy metals.
The iodin can be employed either dissolved in a solution of potassium iodid or in any other suitable solvent or it may be employed in the form of iodids with the addition of agents capable of liberating iodin-for instance, chlorid of lime, chlorin, bromin, or the like.
According to my researches the electric ourrent can also be used more profitably in order to liberate iodin from the iodids. Iodinchlorid, or the combination of iodin, chlorid, and muriatic acid or the like agents, can be used in place of iodin for producing the iodin compounds from the said hydroxyl products or secondary amins or the like. The production of the iodin compounds hereinbefore defined is illustrated by the following examples. The parts are by weight.
Process for Preparation of Tetra-iodo-phenolphtalein.
(a) Under co0Zing.-Thirty grams phenolphtalein are dissolved in one hundred grams water containing forty grams sodium hydrate. To this is added a solution of one hundred grams iodin and one hundred and twenty grams potassium iodid in four hundred grams water, the temperature of which must not exceed centigrade. The red color of the alkaline phenolphtalein solution is during this process changed into a deep blue. The solution is then well cooled and cooled hydrochloric acid is added. An amorphous yellowish-brown body is precipitated,which, by thoroughly washing with a solution of potassium, iodid, and water, can be perfectly purified.
If the moist precipitate is raised to a higher temperature, (about 100 centigrade,) it is converted into a white body-namely, tetraiodophenolphtalein-while the yellowishbrown body produced in the cold is to be considered as tetraiodophenolphtalein plus one molecule of water. It is purified by solution of the undried precipitate in chloroform and precipitation with ligroin, and after drying in racuo it is obtained as a yellow powder devoid of odor and is perfectly permanent in light and air. The analysis gives:
Calculated for O H LH 1: 60.4 per cent. 5 found 1: 60.05 per cent.
The conditions as to solubility and other properties agree with those of the white tetraiodophenolphtalein, which is at once obtained.
(b) By heating-If after adding the iodin the deep-blue solution be heated for some time on a steam-bath, the color changes into a yellowish-brown tint. If hydrochloric acid be added a gray-white body is precipitated,which by thoroughly washing or also by dissolving in soda-lye and precipitating with acids is obtained in a white condition as tetraiodophenolphtalein. It must therefore be assumed that with the body produced in the cold and having an additional molecule of water the lactone formation is destroyed. In the same way that the yellow body can be converted into the white the reverse operation can be effected. If the white tetraiodid of phenolphtalein is dissolved in the cold in soda-lye and hydrochloric acid is added, under cooling, the first-described yellow body is precipitated. After heating with soda-lye until the color changes the white compound is again obtained by means of hydrochloric acid.
The tetraiodophenolphtalein is insoluble in water and ligroin. In the other organic solvents, under heating, it is easily soluble, but with greater difiiculty in the cold. It is most readily taken up by warm chloroform. It is insoluble in acids; readily soluble in alkalies. It is distinguished by perfect absence of odor, and it is quite permanent when exposed to light and moisture.
The analysis gives the formula: C H I O Per cent. Per cent. Calculated I=61.7 0:29.21 H2122 Found I: 61.92 (1: 9.23 11 1.53
Electrolytz'cal production-3O grams phenolphtalein are dissolved in one hundred grams water containing thirty-five grams sodium hydrate. To this are added one hundred and forty grams potassium iodid in two hun dred grams water, and it is subjected to electrolysis for some hours with a current of about 1.5 amperes. The change of color shows the end of the reaction. It is then heated until the blue tint has changed into brownish yellow, and the tetraiodophenolphtalein is precipitated with hydrochloric acid.
Having thus described the various methods of producing tetraiodophenolphtalein, I will now proceed to describe the process for the production of the sodium salts thereof.
The tetraiodophenolphtalein is first dissolved in water containing the calculated quantity of sodium hydroxid, (one-tenth of the employed tetraiodophenolphtalein) and the solution is evaporated to dryness. The salt thus obtained represents, dried at 100, a blue powder very easily soluble in water with a blue color; with more difficulty in alcohol. It corresponds to the formula:
The sodium salt here described is used as a sprinkling-powder in the case of purulent Per cent.
sores, particularlyin the case of soft chancres.
In aqueous solution it is employed for moist bandages and tampons at a concentration of two per cent. For rinsing the bladder in bladder catarrh a solution of two per cent. has given Very excellent results. For healing diseases of the throat and car a solution of from 0.1 to 0.5 per cent. is employed for gargling and rinsing. The sodium saltis also used as first material in the production of various metallic salts of tetraiodophenolphtalein-as, for instance, aluminium, zinc, lead, iron, and manganese salts.
What I claim as new, and desire to secure by Letters Patent, is
As a new article of manufacture, the somy invention Ihave signed my name in pres-- dium salt of an iodin compound containing the enceof two subscribing Witnesses. iodin in the benzene nuclei of phenolphtalein, the same being a dark-blue amorphous pow- ALEXANDER OLASSEN' 5 cler, nearly odorless and tasteless and readily Vitnesses:
soluble in Water, glycerin and alcohol. J OHN HEOKMANNS, In testimony that I claim the foregoing as F. H. BRUNDAGE.
Publications (1)
Publication Number | Publication Date |
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US618167A true US618167A (en) | 1899-01-24 |
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US618167D Expired - Lifetime US618167A (en) | Alexander classen |
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