DE199873C - - Google Patents
Info
- Publication number
- DE199873C DE199873C DENDAT199873D DE199873DA DE199873C DE 199873 C DE199873 C DE 199873C DE NDAT199873 D DENDAT199873 D DE NDAT199873D DE 199873D A DE199873D A DE 199873DA DE 199873 C DE199873 C DE 199873C
- Authority
- DE
- Germany
- Prior art keywords
- formic acid
- diformin
- formins
- glycerine
- pure
- 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.)
- Active
Links
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 30
- 235000019253 formic acid Nutrition 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 235000011187 glycerol Nutrition 0.000 claims description 6
- OETHQSJEHLVLGH-UHFFFAOYSA-N [amino-(diaminomethylideneamino)methylidene]-dimethylazanium;chloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- -1 formic acid glycerol ester Chemical class 0.000 claims 1
- 102000020700 Formins Human genes 0.000 description 4
- 108091021778 Formins Proteins 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-Threitol Natural products OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 2
- 239000004386 Erythritol Substances 0.000 description 2
- 229940009714 Erythritol Drugs 0.000 description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N Erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 235000019414 erythritol Nutrition 0.000 description 2
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 1
- BVDRUCCQKHGCRX-UHFFFAOYSA-N 2,3-dihydroxypropyl formate Chemical compound OCC(O)COC=O BVDRUCCQKHGCRX-UHFFFAOYSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UHFFFAOYSA-N Glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N Hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 101700050571 SUOX Proteins 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- WBEPJBUBTRUGLX-UHFFFAOYSA-N formic acid;propane-1,2,3-triol Chemical class OC=O.OCC(O)CO WBEPJBUBTRUGLX-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 230000002045 lasting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/04—Formic acid esters
- C07C69/10—Formic acid esters of trihydroxylic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
i Ii I
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
-JV* 199873-KLASSE 12 ο. GRUPPE -JV * 199873- CLASS 12 ο. GROUP
Patentiert im Deutschen Reiche vom 6. Januar 1907 ab.Patented in the German Empire on January 6, 1907.
Die bisherigen Darstellungsmethoden der Ameisensäureglycerinester aus Glycerin und Oxalsäure usw. ergeben nicht direkt reine Formine, sondern nur Gemische von verschiedenen Forminen mit Glycerin, d. h. Produkte, welche sich in Äther nicht vollständig lösen, während reine Formine klar ätherlöslich sind. . Bei den bisher bekannten umständlichen und nach Angabe von BeilsteinThe previous methods of preparation of the formic acid glycerol esters from glycerol and Oxalic acid etc. do not give pure formins directly, but only mixtures of different ones Formins with glycerine, d. H. Products that do not completely dissolve in ether, while pure formins are clearly ether-soluble are. . With the previously known cumbersome and according to Beilstein
ίο schwierigen Verfahren konnte daher das Diformin nur durch Ausziehen der Reaktionsmasse mit Äther rein erhalten werden. Es wurde nun gefunden, daß beim Erhitzen von Glycerin mit wasserfreier bzw. hochprozentiger Ameisensäure das Glycerin glatt und vollständig in Formine übergeführt wird, d. h. bei Anwendung der hierzu erforderlichen Menge Ameisensäure Diformin bildet. Diese, Kondensation geht außerordentlich rasch vorίο difficult process could therefore the Diformin can only be obtained pure by extracting the reaction mass with ether. It has now been found that when heated Glycerin with anhydrous or high percentage formic acid makes the glycerin smooth and complete is converted into formine, d. H. if the required amount of formic acid is used, diformin is formed. These, Condensation occurs extremely quickly
ao sich, gleichzeitig ist es möglich,, das bei der Kondensation frei werdende Wasser sowie die überschüssige, als Kondensationsmittel benutzte Ameisensäure direkt: abzudestillieren, " so daß als Reaktionsprodukt im Destillierapparat direkt nur reines Formin zurückbleibt. Diese Verwendung von Ameisensäure als Kondensationsmittel ist neu und bildet das Wesentliche des Pateritanspruches.'ao is, at the same time it is possible ,, the liberated in the condensation water as well as the excess, used as condensing agent formic acid directly: distill, so that remains "as a reaction product in the distillation unit directly only pure Formin This use of formic acid as the condensing agent is new and. forms the essence of the paterite claim. '
Beispiel. 1 kg iooprozentiger Ameisensäure wird mit 0,4 kg hochprozentigen Glycerins gemischt und erhitzt. Bei ioo° und darüber beginnt sofort verdünnte Ameisensäure abzudestillieren. Man setzt die Destillation fort, bis die Temperatur auf etwa 1400 gestiegen ist,, worauf das Diformin zurückbleibt.Example. 1 kg of 100% formic acid is mixed with 0.4 kg of high-percentage glycerine and heated. At 100 ° and above, dilute formic acid begins to distill off immediately. It is the distillation continued, has risen to the temperature to about 140 0 ,, remains after which the Diformin.
Andere Formine als der Ameisensäureglycerinester, z. B. das Äthylendiformin und das Erythrittetraformiat, werden zwar auch durch Kochen mit konzentrierter Ameisensäure erhalten, aber bei diesen ist ein lange anhaltendes Kochen mit sehr bedeutendem Überschuß von Ameisensäure erforderlich, um zum gewünschten Ziele zu gelangen. Ein analoges Verhalten liegt hier also nicht vor, um so weniger als Glycerin sich auch sonst wesentlieh anders verhält als Glykol und Erythrit.Formins other than the glycerol formate, e.g. B. the Äthylendiformin and the erythritol tetraformate can also be obtained by boiling with concentrated formic acid preserved, but with these a long lasting cooking is very significant Excess formic acid required to achieve the desired goal. An analog one So there is no behavior here, all the less since glycerine is otherwise essential behaves differently than glycol and erythritol.
Das nach vorliegendem Verfahren erhältliche Diformin soll als Ersatz für Acetin, z.B. in der Druckerei, sowie als Ersatz für •Ameisensäure technische Verwendung finden.'·The Diformin obtainable according to the present process is intended to replace acetin, e.g. in the printing shop and as a substitute for • formic acid used in technical applications. '·
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE199873C true DE199873C (en) |
Family
ID=462554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT199873D Active DE199873C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE199873C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011007043A1 (en) * | 2009-07-14 | 2011-01-20 | Kemira Oyj | Biocidal composition for wood, method for wood treatment, and wood produced thereby |
| US8273926B2 (en) | 2007-01-26 | 2012-09-25 | The Regents Of The University Of California | Method of converting a polyol to an olefin |
-
0
- DE DENDAT199873D patent/DE199873C/de active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8273926B2 (en) | 2007-01-26 | 2012-09-25 | The Regents Of The University Of California | Method of converting a polyol to an olefin |
| WO2011007043A1 (en) * | 2009-07-14 | 2011-01-20 | Kemira Oyj | Biocidal composition for wood, method for wood treatment, and wood produced thereby |
| US9125404B2 (en) | 2009-07-14 | 2015-09-08 | Tmainco Finland | Biocidal composition for wood, method for wood treatment, and wood produced thereby |
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