DE216917C - - Google Patents
Info
- Publication number
- DE216917C DE216917C DE1908216917D DE216917DA DE216917C DE 216917 C DE216917 C DE 216917C DE 1908216917 D DE1908216917 D DE 1908216917D DE 216917D A DE216917D A DE 216917DA DE 216917 C DE216917 C DE 216917C
- Authority
- DE
- Germany
- Prior art keywords
- lactic acid
- glycerol
- percent
- dilactate
- heated
- 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- 235000011187 glycerol Nutrition 0.000 claims description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 8
- 235000014655 lactic acid Nutrition 0.000 claims description 6
- 239000004310 lactic acid Substances 0.000 claims description 6
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- PVSDCKDNZFNSMO-UHFFFAOYSA-N [3-hydroxy-2-(2-hydroxypropanoyloxy)propyl] 2-hydroxypropanoate Chemical compound CC(O)C(=O)OCC(CO)OC(=O)C(C)O PVSDCKDNZFNSMO-UHFFFAOYSA-N 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RSGINGXWCXYMQU-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-hydroxypropanoate Chemical group CC(O)C(=O)OCC(O)CO RSGINGXWCXYMQU-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- -1 glycerol lactic acid lactone Chemical class 0.000 description 2
- 150000003903 lactic acid esters Chemical class 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VIWIWXKTPWZMEW-UHFFFAOYSA-N 2-hydroxypropanoic acid;propane-1,2,3-triol Chemical class CC(O)C(O)=O.OCC(O)CO VIWIWXKTPWZMEW-UHFFFAOYSA-N 0.000 description 1
- ZZUUMCMLIPRDPI-UHFFFAOYSA-N 2-hydroxypropanoic acid;sodium Chemical compound [Na].CC(O)C(O)=O ZZUUMCMLIPRDPI-UHFFFAOYSA-N 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-M Sodium 2-anthraquinonesulfonate Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002045 lasting Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- IUEMQUIQAPPJDL-UHFFFAOYSA-M sodium;2,3-dihydroxypropanoate Chemical compound [Na+].OCC(O)C([O-])=O IUEMQUIQAPPJDL-UHFFFAOYSA-M 0.000 description 1
- NGSFWBMYFKHRBD-UHFFFAOYSA-N sodium;2-hydroxypropanoic acid Chemical compound [Na+].CC(O)C(O)=O NGSFWBMYFKHRBD-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A47—FURNITURE; DOMESTIC ARTICLES OR APPLIANCES; COFFEE MILLS; SPICE MILLS; SUCTION CLEANERS IN GENERAL
- A47G—HOUSEHOLD OR TABLE EQUIPMENT
- A47G21/00—Table-ware
- A47G21/14—Knife racks or stands; Holders for table utensils attachable to plates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
- C07C69/68—Lactic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
3{q'uetfic(j<m- c3 {q'uetfic (j <m- c
fi've e2fi've e 2
bebtrembling
l'cwnfe.l'cwnfe.
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE-12 o. GRUPPECLASS-12 or GROUP
KALLE & CO. AKT-GES. in BIEBRICH a. Rh.KALLE & CO. ACT-TOTAL in BIEBRICH a. Rh.
Verfahren zur Darstellung von Glycerinmono- und -dilaktatProcess for the preparation of glycerol mono- and dilactate
Verbindungen von Milchsäure mit Glycerin sind bisher nur vereinzelt bekannt geworden, so z. B. das GlycerinmilchsäurelactonCompounds of lactic acid with glycerine have so far only become known sporadically, so z. B. the glycerol lactic acid lactone
„ CH^O-CH-CH8 " CH ^ O-CH-CH 8
I . II. I.
CH-O-COCH-O-CO
CH2-OH -'CH 2 -OH - '
ίο aus Mononatriumglycerat und a-Brompropion-ίο from monosodium glycerate and a-bromopropion
/ säureester (Bischoff, Berl. Ber. 40, S. 2810)./ acid esters (Bischoff, Berl. Ber. 40, p. 2810).
Über die einfachen esterartigen Milchsäureglycerinderivate scheint bisher nichts bekannt geworden zu sein.So far nothing seems to be known about the simple ester-like lactic acid glycerol derivatives to have become.
Versuche haben nun ergeben, daß sich solche Derivate in sehr einfacher Weise durch Erhitzen von Milchsäure mit Glycerin darstellen lassen, und zwar ist dabei im Gegensatz zur Darstellung anderer Milchsäureester überraschenderweise nicht einmal die Anwendung wasserfreier Materialien erforderlich, sondern es genügen die gewöhnlichen mit etwa 75 bis 85 Prozent Reingehalt.Experiments have now shown that such derivatives can be carried out in a very simple manner Heating lactic acid with glycerine is in contrast to the representation of other lactic acid esters Surprisingly, it is not even necessary to use anhydrous materials, but rather the usual ones with about 75 to 85 percent pure content are sufficient.
Ein weiterer Weg besteht in der Umsetzung der Glycerinchlorhydrine mit geeigneten Lactaten. Diese Reaktion vollzieht sich aber nur bei Dichlorhydrin mit technisch genügender Leichtigkeit und Vollständigkeit.Another way is to convert glycerol chlorohydrins with suitable lactates. This reaction takes place only with dichlorohydrin with a technically sufficient level Ease and completeness.
„0 Beispiel 1." 0 example 1.
Man erhitzt 120 g Milchsäure von 75 Prozent mit 106 g Glycerin von 87 Prozent zunächst auf dem Wasserbade und schließlich langsam im Ölbade auf etwa 150 bis i6o° Ölbadtemperatur, bis Gewichtskonstanz ein^ getreten ist. Vorteilhaft ist es dabei, wenn man einen etwa 10 bis 20 Prozent betragenden Glycerinüberschuß anwendet, welcher dann im Vakuum wieder abdestilliert wird. Der einen dicken, zähen, fast farblosen, hygroskopischen Sirup bildende Rückstand hat dann die Zusammensetzung des Glycerinmonolactats.120 g of 75 percent lactic acid are initially heated with 106 g of 87 percent glycerol on the water bath and finally slowly in the oil bath to about 150 to 160 ° Oil bath temperature until the weight is constant. It is advantageous if an approximately 10 to 20 percent excess glycerol is used, which then is distilled off again in vacuo. One is thick, tough, almost colorless, hygroscopic The syrup-forming residue then has the composition of glycerol monolactate.
Wendet man 2 Mol. Milchsäure (= 247 g von 72,5 Prozent) und 1 Mol. Glycerin (= 106 g von 87 Prozent) an und verfährt wie bei 1, so erhält man das Dilactat.·If you use 2 mol. Lactic acid (= 247 g of 72.5 percent) and 1 mol. Glycerin (= 106 g of 87 percent) and proceed as in 1, the dilactate is obtained.
224 g trockenes milchsaures Natrium werden mit 129 g Dichlorhydrin fein zerrieben und zunächst etwa 1 Stunde auf 100 bis iio°, dann weiter einige Stunden bis 150 bis i6o° ■erhitzt. Nach Entfernung des Natriumchlorids erhält man das Dilactat als einen fast farblosen, blaß gelblichbraunen, mäßig dicken hygroskopischen Sirup.224 g of dry sodium lactic acid are finely ground with 129 g of dichlorohydrin and first about 1 hour to 100 to 10 °, then heated for a few more hours to 150 to 160 °. After removing the sodium chloride the dilactate is obtained as an almost colorless, pale yellowish brown, moderately thick hygroscopic syrup.
An Stelle von milchsaurem Natrium können andere milchsaure Salze, z. B. das Kalium- oder Silbersalz, verwendet werden.Instead of lactic acid sodium, other lactic acid salts, e.g. B. the potassium or silver salt, can be used.
Die Glycerinlactate sind mit Wasser und alkoholischen Flüssigkeiten mischbar; Äther lösen sie nur sehr schwer, Schwefelkohlenstoff, Ligroin und ähnliche Lösungsmittel dagegen nicht. Schon durch reines Wasser zerfallen sie in der Kälte langsam, rascher in der Wärme, in ihre Komponenten; ebenso durch sehr schwach saure oder alkalische Lösungen.The glycerol lactates can be mixed with water and alcoholic liquids; ether They are very difficult to dissolve, but carbon disulfide, ligroin and similar solvents on the other hand not. Even with pure water, they slowly disintegrate in the cold, faster in the heat, in their components; also with very weakly acidic or alkaline solutions.
Sie können fast ohne Zersetzung auf ziemlieh hohe Temperaturen erhitzt werden, lassen sich aber nur in sehr hohem Vakuum einigermaßen unzersetzt destillieren.They can be heated to fairly high temperatures with almost no decomposition but can only be distilled somewhat undecomposed in a very high vacuum.
Die neuen Verbindungen sollen besonders in der Therapie an Stelle der Milchsäure selbst verwendet werden, vor welcher sie den Vor-The new compounds are said to be used in therapy instead of lactic acid itself be used, in front of which they
teil der Reizlosigkeit und einer langer dauernden gleichmäßigen Wirkung voraushaben.part of the lack of irritation and a long lasting, uniform effect.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT44375D AT44375B (en) | 1908-09-16 | 1909-03-29 | Process for the preparation of glycerol mono- and dilactate. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE216917C true DE216917C (en) |
Family
ID=478275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1908216917D Expired - Lifetime DE216917C (en) | 1908-09-16 | 1908-09-16 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE216917C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2584998A (en) * | 1948-06-18 | 1952-02-12 | Edward M Filachione | Mixed glycerol esters and their acylation products |
-
1908
- 1908-09-16 DE DE1908216917D patent/DE216917C/de not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2584998A (en) * | 1948-06-18 | 1952-02-12 | Edward M Filachione | Mixed glycerol esters and their acylation products |
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