US567968A - Arthur eichengrun - Google Patents
Arthur eichengrun Download PDFInfo
- Publication number
- US567968A US567968A US567968DA US567968A US 567968 A US567968 A US 567968A US 567968D A US567968D A US 567968DA US 567968 A US567968 A US 567968A
- Authority
- US
- United States
- Prior art keywords
- iodoform
- hexamethylenamine
- arthur
- centigrade
- grains
- 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
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 64
- 229960003172 iodoform Drugs 0.000 description 64
- VKYKSIONXSXAKP-UHFFFAOYSA-N Hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 50
- 239000000203 mixture Substances 0.000 description 38
- 229960004011 Methenamine Drugs 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 24
- 239000002585 base Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000654 additive Substances 0.000 description 14
- 230000000996 additive Effects 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- SQGYOTSLMSWVJD-UHFFFAOYSA-N Silver nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- 230000001476 alcoholic Effects 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- HKZLPVFGJNLROG-UHFFFAOYSA-M Silver chloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 229910001961 silver nitrate Inorganic materials 0.000 description 6
- HFFLGKNGCAIQMO-UHFFFAOYSA-N Chloral Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- PGMYKACGEOXYJE-UHFFFAOYSA-N Amyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- QFFVPLLCYGOFPU-UHFFFAOYSA-N Barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N Ethyl iodide Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- CLSUSRZJUQMOHH-UHFFFAOYSA-L Platinum(II) chloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N Propadiene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229940072049 amyl acetate Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 159000000032 aromatic acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004035 chlorins Chemical class 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- -1 iodoform ethylhexamethyleniodid Chemical compound 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/18—Bridged systems
Definitions
- alkyl iodids usually can be easily combined with ammonia and fatty bases, in forming the iodin salts of amine, imide, nitrile, and ammonium bases, iodoform, which already differs entirely by its manner of formation and its chemical behavior from the real alkyl iodids, remains quite indifferent upon coming in contact with these bases.
- iodoform readily enters into a combination with the nitrile base hexamethylentetramine in producing a substance of the compositions O H N -OHI
- This compound is not only formed by the action of iodoform upon the free base, but also upon the additive products which the latter forms with other substances, in which case these compounds are decomposed into their components, as such additive combinations are principally to be considered as the combinations of hexamethylenamine with phenols,with chlorids of aromatic acids, and with a1dehydesfor instance, the combination of hexamethylenamine and hydrate of chloral.
- Example I Fourteen grains hexamethylenamine are dissolved in absolute alcohol, then 39.4 grains of iodoform are added, and the mixture heated a short time by means of a water-bath. A white fine powder is then deposited consisting of iodoform hexamethylentetramine and having the above-mentioned properties. Instead of taking pure hexamethylentetramine one may mix the alcoholic solutions of its components with a solution of iodoform.
- Example II 23.4 grains of monophenolhexamethylenamine are dissolved in alcohol, then 39.4 grains iodoform added, and the precipitated iodoform hexamethylenamine filtered. The mother liquor contains all the phenol.
- Example III Dissolve 30.5 grains chloralhexamethylenamine in chloroform, add a hot solution of 39.4 grains iodoform in the same dissolvent, and apply a gentle heat to promote the action. After cooling one separates the precipitation from the solution containing the hydrate of chloral and washes the iodoform hexamethylenamine with alcohol.
- Example IV Dissolve 29.6 grains ethyliodid hexamethylentetramine in absolute alcohol, add an alcoholic solution of 39.4 grains iodoform, and heat for a short time. On cooling a mass of lemon-yellow crystals is deposited consisting of iodoform ethylhexamethyleniodid. They melt at 128 centigrade, are not soluble in Water, readily soluble in hot alcohol. If the alcoholic solution is heated too long, another compound is formed, melting at 172 centigrade. It seems to be an isomeric of the above combination.
- Example V One dissolves iodoform hexamethylenamine in amyl acetate and adds to the hot solution methyliodide. On cooling the iodoform methylhexamethylenaminiodid is obtained in light-yellow needles, which are easily dissolved in alcohol and melt at 179 centigrade.
- iodoform with alkyl-haloid derivatives of hexamethylenamine; as, for instance, methylene iodidhexamethylenamine forms, with iodoform an additive product, crystallizing in small yellow needles, melting at 174 centigrade. Bromethylhexamethylenamine (melting at 155 centigrade) forms With iodoform a new compound, which is easily soluble in alcohol and crystallizes in light-yellow prisms, melting at 114 centigrade.
- compositions of matter to be used for surgical purposes consisting of crystalline inodorous additive combinations of iodoform with hexamcthylentetramine or its haloidalkyl derivatives, which are not soluble in water and become decomposed into their components by the action of acids or alkalies, liberating iodoform.
Description
NITE STATES FFICE.
ARTHUR EIOHENGRT IN, OF BONN, GERMANY.
SPECIFICATION forming part of Letters Patent No. 567,968 dated September 22, 1896. Application filed December 8, 1895. Serial No. 571,257. (Specimens) To all whom it may concern.-
Be it known that I, ARTHUR EIOHENGRUN, a citizen of Germany, residing at Bonn, Gen many, have invented new and useful Chemical Combinations to be Used for Surgical Purposes, of which the following is a specification.
Combination of Iodoform with Heaamethylentetramz'ne and its Haloidalkyl Derivatires.
Whereas the alkyl iodids usually can be easily combined with ammonia and fatty bases, in forming the iodin salts of amine, imide, nitrile, and ammonium bases, iodoform, which already differs entirely by its manner of formation and its chemical behavior from the real alkyl iodids, remains quite indifferent upon coming in contact with these bases. For this reason it is very peculiar that iodoform, as I have discovered, readily enters into a combination with the nitrile base hexamethylentetramine in producing a substance of the compositions O H N -OHI This compound is not only formed by the action of iodoform upon the free base, but also upon the additive products which the latter forms with other substances, in which case these compounds are decomposed into their components, as such additive combinations are principally to be considered as the combinations of hexamethylenamine with phenols,with chlorids of aromatic acids, and with a1dehydesfor instance, the combination of hexamethylenamine and hydrate of chloral.
The action of iodoform on hexamethylenamine or one of its derivatives produces the above mentioned iodoform hexamethylenamine C I-I N OHI This result is very strange for the following reasons: first, because additive combinations of iodoform and free bases are entirely unknown; second, because according to the combinations of hexa methylentetramine with real alkylhaloids (discovered by A. Wohl, Berz'chte der Deutschen Chem. Gescllsch. XIX, 1840) one should have expected that iodoform, in case of its at all entering into reaction with this base,
would combine with three molecules of hexamethylenamine, thus:
The reason that the process does not turn out in aforesaid manner, (formula 0,) but, instead, that the compound O H l T -OI-II is formed, is that this substance is a molecular additive combination, whereas the products obtained by Wohl are iodin salts of new bases, (methyl, ethyl, methylene, ethylene, hexamethylentetramine, which are real atomistic combinations. This can be seen from the entirely-different chemical properties. Iodoform hexamethylenamine is a white subtile powder, which melts at 178 centigrade and cannot be dissolved either in water or in ether or in alcohol. Upon coming in contact with diluted acids or alkalies, and even being agitated With water, it separates into iodoform and hexamethylenamine. By the action of silver nitrate no precipitation of silver iodid is formed,but iodoform liberated, and a double salt of silver nitrate and hexamethylenamine formed. By the action of silver ohlorid and platinum chlorid the same decomposing effect is produced. On the other hand, the compounds of Wohl have the characteristic properties of iodin salts of ammonium bases. They are easily soluble in Water and crystallize unaltered by evaporating the aqueous solution. The iodin is completely removed by treatment with silver nitrate.
When heated with silver chlorid, WVohls compounds are converted into the corresponding chlorin salts from which platinchloriddouble salts-can be prepared:
I O1 O I-I N +AgOl: O II, N,+AgI.
CH 01-1 but:
0 H, N CHI +AgCl:C.,H, N,AgCl+OHI When heated in alcoholic solution, WVohls compounds become altered, as, for instance, the ethiodid hexamethylenamine, melting at 144 centigrade, is converted into a compound melting at 180 centigrade, but never under any circumstances do they decompose into their components as iodoform hexamethylenamine does. If hydrate of potash be added to a concentrated watery solution, the compounds of Wohl are precipitated without being altered. This reaction doubtless shows that they are salts of quaternary ammonium bases. As such compounds they are not able to form a combination with another haloidalkyl, but just as well as hexamethylenamine itself they are also able to form additive combinations with iodoform. These new compounds have the same chemical properties as iodoform hexamethylenamine. They cannot be dissolved in water and become decomposed with acids and alkalies in liberating iodoform. Equally as well as by the action of iodoform on haloidalkyl hexamethylenamine they can be obtained by the action of haloidalkyl iodoform hexamethylenamine.
111 ethods for Preparing.
Example I: Fourteen grains hexamethylenamine are dissolved in absolute alcohol, then 39.4 grains of iodoform are added, and the mixture heated a short time by means of a water-bath. A white fine powder is then deposited consisting of iodoform hexamethylentetramine and having the above-mentioned properties. Instead of taking pure hexamethylentetramine one may mix the alcoholic solutions of its components with a solution of iodoform.
Example II: 23.4 grains of monophenolhexamethylenamine are dissolved in alcohol, then 39.4 grains iodoform added, and the precipitated iodoform hexamethylenamine filtered. The mother liquor contains all the phenol.
Example III: Dissolve 30.5 grains chloralhexamethylenamine in chloroform, add a hot solution of 39.4 grains iodoform in the same dissolvent, and apply a gentle heat to promote the action. After cooling one separates the precipitation from the solution containing the hydrate of chloral and washes the iodoform hexamethylenamine with alcohol.
Example IV: Dissolve 29.6 grains ethyliodid hexamethylentetramine in absolute alcohol, add an alcoholic solution of 39.4 grains iodoform, and heat for a short time. On cooling a mass of lemon-yellow crystals is deposited consisting of iodoform ethylhexamethyleniodid. They melt at 128 centigrade, are not soluble in Water, readily soluble in hot alcohol. If the alcoholic solution is heated too long, another compound is formed, melting at 172 centigrade. It seems to be an isomeric of the above combination.
Example V: One dissolves iodoform hexamethylenamine in amyl acetate and adds to the hot solution methyliodide. On cooling the iodoform methylhexamethylenaminiodid is obtained in light-yellow needles, which are easily dissolved in alcohol and melt at 179 centigrade. By the same methods one obtains the other combinations of iodoform with alkyl-haloid derivatives of hexamethylenamine; as, for instance, methylene iodidhexamethylenamine forms, with iodoform an additive product, crystallizing in small yellow needles, melting at 174 centigrade. Bromethylhexamethylenamine (melting at 155 centigrade) forms With iodoform a new compound, which is easily soluble in alcohol and crystallizes in light-yellow prisms, melting at 114 centigrade.
What I claim as my invention, and desire to secure by Letters Patent of the United States, is-
The herein-described compositions of matter to be used for surgical purposes, consisting of crystalline inodorous additive combinations of iodoform with hexamcthylentetramine or its haloidalkyl derivatives, which are not soluble in water and become decomposed into their components by the action of acids or alkalies, liberating iodoform.
Signed at Cologne, in the Empire of Germany, this 23d day of November, A. D. 1895.
ARTHUR EIOHENGRUN.
Witnesses:
SOPHIE NAGEL, MARIA NAGEL.
Publications (1)
Publication Number | Publication Date |
---|---|
US567968A true US567968A (en) | 1896-09-22 |
Family
ID=2636674
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US567968D Expired - Lifetime US567968A (en) | Arthur eichengrun |
Country Status (1)
Country | Link |
---|---|
US (1) | US567968A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3244710A (en) * | 1963-12-23 | 1966-04-05 | Dow Chemical Co | Iodine complexes of hexamethylene-tetramine quaternary salts |
-
0
- US US567968D patent/US567968A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3244710A (en) * | 1963-12-23 | 1966-04-05 | Dow Chemical Co | Iodine complexes of hexamethylene-tetramine quaternary salts |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US567968A (en) | Arthur eichengrun | |
Jones et al. | THE BECKMANN REARRANGEMENT INVOLVING OPTICALLY ACTIVE RADICALS1 | |
US726126A (en) | Mercury salts of ethylenediamin bases and process of making same. | |
US1685407A (en) | Dicyclic derivatives of pentamethylene and process for the manufacture of same | |
RU2470913C1 (en) | Method of producing gamma-glycine from solutions | |
Bogert et al. | RESEARCHES ON QUINAZOLINES (TWENTY-FOURTH PAPER). ON OXALYL ANTHRANILIC COMPOUNDS AND QUINAZOLINES DERIVED THEREFROM. | |
US483290A (en) | Israel roos | |
US692437A (en) | Hydrochlorid of cinnamyl-quinin and process of making same. | |
US706356A (en) | Acet salicyl phenetidin and process of making same. | |
US892414A (en) | Process for preparation of phthalic-acid salts of cotarnin and product resulting therefrom. | |
Japp et al. | XXXIV.—On the action of aldehydes on phenanthraquinone in presence of ammonia.(Second notice.) | |
RU2480450C1 (en) | Method for preparing gamma-glycine from solutions | |
Adams et al. | PHENYL ESTERS OF OXALIC ACID. | |
US1145487A (en) | Process for producing 4-ketones of the quinolin series. | |
US848230A (en) | Bromin derivative of fatty acids. | |
US646631A (en) | Phenol ether of quinin carbonic acid. | |
US1052762A (en) | Pharmaceutical product. | |
McCombie et al. | LXXV.—Condensations of cyanohydrins. Part I. Condensation products from anisaldehydecyanohydrin and cinnamaldehydecyanohydrin | |
Rennie | VII.—On benzyl-phenol and its derivatives | |
US676861A (en) | Process of preparing alkylized purins. | |
Curtiss et al. | Pseudo acid esters in the mesoxalic ester synthesis. | |
US654123A (en) | Formic aldehyde compound of uric acid and process of making same. | |
US782739A (en) | C-c-dialkyl-barbituric acid and process of making same. | |
US631762A (en) | Process of making oxymethylene-uric acid. | |
US598502A (en) | Emil fischer |