US829262A - Preparation of amino alcohol. - Google Patents
Preparation of amino alcohol. Download PDFInfo
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- US829262A US829262A US19928304A US1904199283A US829262A US 829262 A US829262 A US 829262A US 19928304 A US19928304 A US 19928304A US 1904199283 A US1904199283 A US 1904199283A US 829262 A US829262 A US 829262A
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- 150000001414 amino alcohols Chemical class 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 230000008569 process Effects 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- -1 AMINO Chemical class 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- VFPKIWATTACVJR-UHFFFAOYSA-N 1-(dimethylamino)propan-2-one Chemical compound CN(C)CC(C)=O VFPKIWATTACVJR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- BCDGQXUMWHRQCB-UHFFFAOYSA-N aminoacetone Chemical class CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003747 Grignard reaction Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 125000001650 tertiary alcohol group Chemical group 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- QQXLDOJGLXJCSE-KNVOCYPGSA-N tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 2
- XJGZYFXMKLIKCX-UHFFFAOYSA-N 2-(dimethylamino)butan-2-ol Chemical compound CCC(C)(O)N(C)C XJGZYFXMKLIKCX-UHFFFAOYSA-N 0.000 description 1
- VQFCXWUBLIFPCR-UHFFFAOYSA-N 3-(dimethylamino)pentan-3-ol Chemical compound C(C)C(CC)(O)N(C)C VQFCXWUBLIFPCR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000007519 figuring Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- LRZFEBJUJIQVDQ-UHFFFAOYSA-N methyl 2-(dimethylamino)acetate Chemical compound COC(=O)CN(C)C LRZFEBJUJIQVDQ-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
Definitions
- Patented rin 21, 1906 Patented rin 21, 1906.
- the present invention relates to a process for making alkamins (amino alcohols) which contain a tertiary alcohol group and a tertiary amino group.
- the heating under pressure is avoided as, figuring from the halogenacetone (Stormer Bertclzte 9 28, 223) and the halogen-acid esters (Nillstatter Bcrichtc 35, p. 594) the corresponding amino dcrivates are formed in the cold, and in their turn also enter into reaction on the magnesium organic compounds in the which is slighter than that of the eucaines and cocaines.
- These salts moreover, are exceedingly easily soluble in water with the exception of those of the aromatic series, which are less easily soluble.
- the solutions under action of heat are completely sterilizable, as they undergo no changes even with a continuous heating to 110.
- Example 1 Ethyldimethylaminopropanol I on2. CH3.(JH2.COH CH3 CH3 Twenty-four grams of magnesium are dis solved in one hundred and eighty grams of ethyl bromid as well as three hundredgrams of other free of water, according to Grignards directions, (loco citato.) As soon as the ingredients are dissolved one hundred grams of dimethylaminacetone, which boils at 123, (Stoermore, loco citato) are slowly introduced into the cooled-ofi liquid. The reaction is a very lively one. A white powder is 'reci itated and the ether is brought to boil The liquid remains but little colored, and the introduction of the dimethylacetone keeps on for about three hours.
- the mixture is left to itself for half a day. Then it is mixed with ounded ice and hydrochloric acid, which liitter is added in just sufficient quantity to make the medium slightly acid. Now the existing-acid layer is decanted and evaporated as much as possible with rarefication of air. It then suffices to treat the remaining salty mass at low temperature with a concentrated solution of soda in order to be able to take up the base in a solution of other, whereafter the whole is distilled With rarefication of air after the solvent has been dried out and evaporated. The product boilsat 37 and twenty-three millimeters mercurial column.
- Phenyldimethylaminopropanol CH3 H2N I CH3 This body can be obtained by either allowing phenylmagnesiumbromid to act on dimethylaminoacetone, which represents the most practical recess, or methylniagnesiumioilid. may also ncaused to act on (limethylamino- Seventy grams magnesium, in strips or in form of powder,'are dissolved in four hundred grains of iodidemethyl and two thousand grams of other free from water. As soon as the solution is complete, (the mixture is) cooled off, and. three hundred grams dinicthylamidoacetophenone(previously dissolved in five hundred grams of ether free from water) are allowed to flow into the liquid drop by drop. The reaction is a lively one and is conductei-l exactly as in the previous cases. The whole is left to itself for twenty-four hours, and the (EH5. OOH
- saaaaa mass is then decomposed. by means of ice and hydrochloric acid.
- the base is then freed from the aeidiferous solution b means of soda and finally subjected to a distillation after the same has been lixiviated by means of ether.
- the body boils at to and twenty-four millimeters Hg. It is li uid, very slightly soluble in water, less s luble in warm than in cold water.
- the hydrochloric compound crystallizes out of acetone in ver fine needles, in which it is very slightly so uble in cold and melts at 158 to 160. Chlor-aurate in raw state melts at 110.
- the benzoylizedderivative is viscous and colorless. Its. hydrochloric compound is very slightly soluble in absolute, even warm, alcohol and dissolves pretty badly in cold water. It crystallizes out of absolute alcohol in beautiful prisms, which melt at 205 to-206.
- This body is obtained by allowing dimethylaminoacetone to act u on methylamagnesiumiodid.
- the hydrochloric compound of their benzo lized derivatives crystallizes out of the sol tion in boiling absolute alcohol in large cubes, which decompose in the air and melt at 202 Eaamp le. 5.
- Phenyldiethylarninopropanol: I /C2H5 is obtained by allowing benzylmagnesiumactionated chlorid to act upon dimethylaminoacetone.
- the chlorhydrate of the benzoylized deriva tive melts at 134 and crystallizes out of an alcohol-ether mixture in long hygroscopic needles.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
UNITED STATES PATENT OFFICE.
ERNEST FOU RNEAU,
0F PARIS, FRANCE.
PREPARATION OF AMINO ALCOHOL- Specification of Letters "Patent.
Patented rin 21, 1906.
Application filed March 21, 1904. Serial No. 199,283.
citizen of the Republic of France, residing in the city of Paris, in the Republic of France, have invented" certain new and useful Improvements in the Preparation of Amino Alcohols, of which the following is a specification.
The present invention relates to a process for making alkamins (amino alcohols) which contain a tertiary alcohol group and a tertiary amino group.
The processes generall used for producing alkamins are limited to our: First, action of amins'on the halogen hydrins, (Wurtz, Liebigs Ann. 121, 228;) second, action of amins on ethylenoxids, (Wurtz, Suppl. Ann. 6, 202;) third, reduction of the amlnoacetones, (Heintz, Ltebigs Ann. 182, 29; O'Zoezs Ann. 6, 9, 159;) fourth, fixing the ingredients of the water onto the double compound of a base which contains an ethylene group (Willstatter, Liebt'gs Ann. 326, p. 93; Einhorn, Berickte 23, p. 2889.) In reality the first process alone is available for the alkamins of the kind mentioned at the beginning, and it was a question still of discovering a process which permits the production in an easy way of the suitable halogen h drins.
The researches of rignard (Oomptes- Rendus dc ZAcademtc des Sciences 132, pp. 528, 836, 133, &c.) have enabled Tiffeneau to bring about the synthesis of these halogenhydrins with ease. His process consists herein that the magnesium or anic compounds are permitted to act on halogen acetones (0'. R. Ac. D. Sc. 134, p. 774.) The yield, however, is usually too slight and too irregular. Besides, complicated secondary reactions may arise, which are to be ascribed to the intense chemical activity of the halogen in the molecule. Finally, the halogen hydrin once formed changes very easily. Now the process forming the object of the present application is founded on an entirely new application of Grignards reaction, and consists herein that the magnesium organic compounds are brought to act on aminoacetones or on the ester of an amino acid with tertiary amino group.
Examples.
CH2. N I
1. CH3lMg+GO corn emu H2O ore on.
CH3 H2O OOH" CH3 CzaHeGzHs COMgBrCH3 CIIz-N cn. The advantages which the present method show as compared with the known processes are as followsi First. This method makes the production of halogen hydrins unnecessary, and thus the reactions connected with this production do not appear. Conse uently the yield almost corresponds to the t eoretical one, and the product of reaction distils to the last drop without undergoing the slightest decomposition.
Second. It permits not only to produce the alkamins, which are derived from the halogen hydrins of Tifieneau, but also all alkamins which are derived from any desired aminoacetone or amino-acid ester. Thus, for instance, the alkamins which are derived from tropinone or from triacetonamiu.
Third. By means of the process the heating under pressure is avoided as, figuring from the halogenacetone (Stormer Bertclzte 9 28, 223) and the halogen-acid esters (Nillstatter Bcrichtc 35, p. 594) the corresponding amino dcrivates are formed in the cold, and in their turn also enter into reaction on the magnesium organic compounds in the which is slighter than that of the eucaines and cocaines. These salts, moreover, are exceedingly easily soluble in water with the exception of those of the aromatic series, which are less easily soluble. Furthermore, the solutions under action of heat are completely sterilizable, as they undergo no changes even with a continuous heating to 110.
Example 1. Ethyldimethylaminopropanol I on2. CH3.(JH2.COH CH3 CH3 Twenty-four grams of magnesium are dis solved in one hundred and eighty grams of ethyl bromid as well as three hundredgrams of other free of water, according to Grignards directions, (loco citato.) As soon as the ingredients are dissolved one hundred grams of dimethylaminacetone, which boils at 123, (Stoermore, loco citato) are slowly introduced into the cooled-ofi liquid. The reaction is a very lively one. A white powder is 'reci itated and the ether is brought to boil The liquid remains but little colored, and the introduction of the dimethylacetone keeps on for about three hours.
After the same is ended the mixture is left to itself for half a day. Then it is mixed with ounded ice and hydrochloric acid, which liitter is added in just sufficient quantity to make the medium slightly acid. Now the existing-acid layer is decanted and evaporated as much as possible with rarefication of air. It then suffices to treat the remaining salty mass at low temperature with a concentrated solution of soda in order to be able to take up the base in a solution of other, whereafter the whole is distilled With rarefication of air after the solvent has been dried out and evaporated. The product boilsat 37 and twenty-three millimeters mercurial column. It consists of a mobile, almost colorless, liquid of slight odor, which is very easily soluble in water and the other solvents. The eorres onding salts are crystallizable with (liilicu ty excepting the oxalate. The chlorplatin-aeid salt is very soluble in Water and alcohol. The aurate, on the other hand, is very dillic'ult to dissolve, but liquefics out of this solvent 'acetophcnone for this purpose.
efi'ect when a small quantity of the same is placed on the tongue. Example. 2. 'Ethyldimethylaminobutanol:
CHaN CafisCOH H3 Cells The process used herefor is exactly the same as that before described, with the single exception that the ethylmagnesium bromid is no longer allowed to be acted upon by dimethylaminoacetone, but ethyl or methyl dimethylaminoacetate, which has been obtained by the Willstatter process, (Berichte 35, p. 594.) The yield is much less satisfactory and there very probably arise alkamins which contain an oxid-ester group.
its homologues, causes At all events the reigning product, about sixty per cent., consists of ethyldimethylbutano Which boils at 76 to 79 and twenty-four millimeters Hg. The product consists of an almost wholly colorless liquid which is less soluble in water than the body before described. The hydrochloric com mind of the benzoylized derivative is slight y soluble in cold absolute alcohol and crystallizes from in beautifully shining little plates, which melt at 189. Like all its homologues it is but slightly soluble in acetone.
Example.
3. Phenyldimethylaminopropanol CH3 H2N I CH3 This body can be obtained by either allowing phenylmagnesiumbromid to act on dimethylaminoacetone, which represents the most practical recess, or methylniagnesiumioilid. may also ncaused to act on (limethylamino- Seventy grams magnesium, in strips or in form of powder,'are dissolved in four hundred grains of iodidemethyl and two thousand grams of other free from water. As soon as the solution is complete, (the mixture is) cooled off, and. three hundred grams dinicthylamidoacetophenone(previously dissolved in five hundred grams of ether free from water) are allowed to flow into the liquid drop by drop. The reaction is a lively one and is conductei-l exactly as in the previous cases. The whole is left to itself for twenty-four hours, and the (EH5. OOH
IIO
saaaaa mass is then decomposed. by means of ice and hydrochloric acid. The base is then freed from the aeidiferous solution b means of soda and finally subjected to a distillation after the same has been lixiviated by means of ether. The body boils at to and twenty-four millimeters Hg. It is li uid, very slightly soluble in water, less s luble in warm than in cold water. The b ody in time, in cold, reduces permanganate of potassium in acid solution, and this reduction takes place very rapidly, heat being applied. The hydrochloric compound crystallizes out of acetone in ver fine needles, in which it is very slightly so uble in cold and melts at 158 to 160. Chlor-aurate in raw state melts at 110. The benzoylizedderivative is viscous and colorless. Its. hydrochloric compound is very slightly soluble in absolute, even warm, alcohol and dissolves pretty badly in cold water. It crystallizes out of absolute alcohol in beautiful prisms, which melt at 205 to-206.
- Example. 4. Methyldimethylaminopropanol:
This body is obtained by allowing dimethylaminoacetone to act u on methylamagnesiumiodid. The base bolls at 160 and fortyeight millimeters Hg. Its ro erties are the same as those of the base bellire described. The hydrochloric compound of their benzo lized derivatives crystallizes out of the sol tion in boiling absolute alcohol in large cubes, which decompose in the air and melt at 202 Eaamp le. 5. Phenyldiethylarninopropanol: I /C2H5 is obtained by allowing benzylmagnesiumactionated chlorid to act upon dimethylaminoacetone. This product presents a thick liquid, which boils at 144 and twenty-four millimeters Hg. The chlorhydrate of its benzoylized derivative crystallizes from out of absolute alcohol and out of methyl alcohol in beautiful trans arent prisms several millimeters in lengt which melt at Example. 7. Propyldimethylaminopropanol:
GH3 CH3.CH2.OH2.COH CH3 CH2.N
is obtained by allowing ro lma esiumbromid and dimethylamiiioaPdetong to act upon each other. This base is very soluble in water and boils at 78 and thirty-five millimeters H The salt compounds are uncrystalliza le. The chlorhydrate of the benzoylized derivative melts at 140 and crystallizes out of an alcohol ether mixture in very fine needles. It is very soluble in absolute alcohol and hygroscopic besides.
Example.
8. Isobutyldimethylaminopropanol H3 CH3 H2.N omoon "H8 CH3 CH3 This base boils at 83 and 34 millimeters Hg.
The chlorhydrate of the benzoylized deriva tive melts at 134 and crystallizes out of an alcohol-ether mixture in long hygroscopic needles.
in the air, and is very slig tly soluble in water. The product boils at 98 to 99 and twenty-four millimeters Hg. The chlorhydrate of the benzoylized derivative crystallizes out of an alcohol-etheranixture in long silk-like non-h groscopic needles, which are almost insolub e in acetone; but, on the other hand, very soluble in alcohol. and melt at 138 I claim as my invention In testimony whereof I have signed my The process for producmg alkamms conname to this specification in the presence of taining tertiary alcohol group and tertiary two subscribing witnesses amino group, which consists in causing mag- ERNEST FOURNEAU. 5 nesium organic com ounds to act upon Witnesses:
aminoacetones where y bodies are obtained HANSON C. OOXE,
adapted to produce local anesthesia, &c. ANTONIN MOUHEALHE-.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19928304A US829262A (en) | 1904-03-21 | 1904-03-21 | Preparation of amino alcohol. |
| US263636A US828846A (en) | 1904-03-21 | 1905-06-03 | Process of making alkamins. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19928304A US829262A (en) | 1904-03-21 | 1904-03-21 | Preparation of amino alcohol. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US829262A true US829262A (en) | 1906-08-21 |
Family
ID=2897738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US19928304A Expired - Lifetime US829262A (en) | 1904-03-21 | 1904-03-21 | Preparation of amino alcohol. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US829262A (en) |
-
1904
- 1904-03-21 US US19928304A patent/US829262A/en not_active Expired - Lifetime
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