DE921266C - Solvents and neutralizers for amines - Google Patents
Solvents and neutralizers for aminesInfo
- Publication number
- DE921266C DE921266C DEB19495A DEB0019495A DE921266C DE 921266 C DE921266 C DE 921266C DE B19495 A DEB19495 A DE B19495A DE B0019495 A DEB0019495 A DE B0019495A DE 921266 C DE921266 C DE 921266C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- amines
- solvents
- water
- boric acid
- 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
Links
- 150000001412 amines Chemical class 0.000 title claims description 14
- 239000002904 solvent Substances 0.000 title claims description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 9
- 239000004327 boric acid Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 235000000346 sugar Nutrition 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 150000008163 sugars Chemical class 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 4
- 210000004400 mucous membrane Anatomy 0.000 description 4
- 239000008121 dextrose Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- -1 amines Amines Chemical class 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- 125000005219 aminonitrile group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Description
Lösungs- und Neutralisierungsmittel für Amine Amine wirken bekanntlich stark reizend auf Schleimhäute. Insbesondere können sie im Auge schwerste Dauerschäden verursachen. Das gilt sowohl für wasserunlösliche Amine, wie Oleyl-, Stearyl- oder das sogenannte Dimethylpalmkernfettamin oder Anilin und seine Substitutionsprodukte und Aminonitrile, wie auch für wasserlösliche Amine, wie Diäthylamin oder Äthylen- und Hexamethylendiamin oder Äthanolamine.Solvents and neutralizing agents for amines Amines are known to have an effect strongly irritating to mucous membranes. In particular, they can cause very severe permanent damage to the eye cause. This applies to both water-insoluble amines, such as oleyl, stearyl or the so-called dimethyl palm kernel fatty amine or aniline and its substitution products and aminonitriles, as well as for water-soluble amines, such as diethylamine or ethylene and hexamethylenediamine or ethanolamines.
Man hat bisher versucht, die Amine durch Lösungen schwacher organischer Säuren, wie Essigsäure, zu lösen und zu neutralisieren, muBte dabei aber Schädigungen der Schleimhäute durch diese Säuren in Kauf nehmen. Überdies werden manche Amine durch verdünnte wäßrige Essigsäure nicht oder nur unvollständig gelöst oder neutralisiert. Es wurde nun gefunden, daß die durch Umsetzung von Borsäure mit aliphatischen Polyalkoholen und vorteilhaft mit Zuckern im ungefähren Gewichtsverhältnis i : (q.-6) : (0-0,7) erhältlichen Produkte sich vorzüglich als Lösungs- und Neutralisierungsmittel für Amine eignen. Diese Umsetzungsprodukte sind in Wasser leicht löslich; die Lösungen vermögen, im Gegensatz zur Borsäure selbst, wasserunlösliche Amine glatt zu lösen und alle Arten von Aminen derart zu neutralisieren, daB sie keine Schädigung der Schleimhäute mehr ausüben. Sie sind im Gegensatz zur Essigsäure völlig indifferent gegen die Schleimhäute, sogar gegen die Cornea des Auges.Attempts have been made so far, the amines by solutions of weak organic To dissolve and neutralize acids such as acetic acid, however, had to do some damage of the mucous membranes due to these acids. In addition, some become amines not or only incompletely dissolved or neutralized by dilute aqueous acetic acid. It has now been found that the reaction of boric acid with aliphatic polyalcohols and advantageously with sugars in the approximate weight ratio i: (q.-6): (0-0.7) available products are excellent as solvents and neutralizing agents for Amines are suitable. These reaction products are easily soluble in water; the solutions are able, in contrast to boric acid itself, to dissolve water-insoluble amines smoothly and to neutralize all types of amines in such a way that they do not damage the Exercise more mucous membranes. In contrast to acetic acid, they are completely indifferent against the mucous membranes, even against the cornea of the eye.
Als aliphatische Polyalkohole kann man z. B. Glycerin, i, 6-Hexandiol, Glykol, Diäthylentriglykol oder Butantriol verwenden; als Zucker eignen sich unter anderem Traubenzucker, Saccharose, Ribose.As aliphatic polyalcohols you can, for. B. glycerin, i, 6-hexanediol, Glycol, diethylene triglycol or use butanetriol; than sugar among others, dextrose, sucrose, ribose are suitable.
Die Umsetzung erfolgt zweckmäßig durch kurzes Erwärmen, z. B. auf 8o bis ioo°.The reaction is expediently carried out by brief heating, e.g. B. on 8o to 100 °.
Die in den folgenden Beispielen genannten Teile sind Gewichtsteile. Beispiel i Man löst 5o Teile Borsäure unter Erwärmen in 25o Teilen Glycerin, fügt 3o Teile Traubenzucker hinzu und erwärmt weiter, bis eine klare Lösung entstanden ist. Der erhaltene Sirup wird mit dem doppelten Volumen Wasser verdünnt; diese Lösung löst wasserunlösliche Fettamine glatt auf. Beispiel 2 Man löst ,4o Teile Borsäure unter Erwärmen in 25o Teilen i, 6-Iiexandiol, fügt 3o Teile Traubenzucker hinzu und erwärmt weiter, bis ein homogener Sirup entstanden ist. Dieser wird mit der zwei- bis dreifachen Menge Wasser verdünnt. Die erhaltene Lösung löst Oleylamin bereits in der Kälte rasch und vollständig zu einer klaren, schäumenden, mit Wasser beliebig verdünnbaren Lösung. Beispiel 3 Man trägt in 26o Teile Ät'hylenglykol bei 70° unter Rühren 4.5 Teile Borsäure und 3o Teile Traubenzucker ein und rührt, bis alles gelöst ist. Die wäßrige Lösung des erhaltenen Sirups löst Fettamine klar auf. Beispiel q.The parts mentioned in the following examples are parts by weight. EXAMPLE i 50 parts of boric acid are dissolved in 250 parts of glycerol with heating Add 3o parts glucose and continue heating until a clear solution is obtained is. The syrup obtained is diluted with twice the volume of water; this solution dissolves water-insoluble fatty amines smoothly. EXAMPLE 2 40 parts of boric acid are dissolved while heating in 25o parts of i, 6-iiexanediol, add 30 parts of glucose and continue to heat until a homogeneous syrup is obtained. This is with the Diluted two to three times the amount of water. The solution obtained dissolves oleylamine even in the cold quickly and completely to a clear, foaming, with water Any solution that can be diluted. EXAMPLE 3 260 parts of ethylene glycol are added 70 ° with stirring 4.5 parts of boric acid and 3o parts of grape sugar and stir until everything is resolved. The aqueous solution of the syrup obtained dissolves fatty amines clearly. Example q.
Man trägt in 55o Teile i, 2, q.-Butantriol bei 8o° unter Rühren ioo Teile Borsäure und 55 Teile Traubenzucker ein und erwärmt, bis eine klare Lösung entstanden ist. Das Produkt löst Fettamine. Beispiel 5 Man löst 8o Teile Borsäure in 5oo Teilen Glycerin unter Erwärmen auf. Nach Verdünnen mit dem zwei- bis dreifachen Volumen Wasser erhält man eine Lösung, die Fettamine klar löst. Beispiel 6 In ioo Teile einer Lösung von 5o Teilen Borsäure und 3o Teilen Traubenzucker in 25o Teilen Glycerin trägt man 15 Teile Anilin ein. Das Anilin löst sich rasch bereits bei gewöhnlicher Temperatur. Die erhaltene klare Lösung kann mit Wasser verdünnt werden, ohne sich zu trüben.One carries i, 2, q.-butanetriol in 55o parts at 80 ° with stirring Parts boric acid and 55 parts dextrose and heated until a clear solution originated. The product dissolves fatty amines. Example 5 80 parts of boric acid are dissolved in 500 parts of glycerol with heating. After diluting by two to three times Volume of water gives a solution which clearly dissolves fatty amines. Example 6 In ioo Parts of a solution of 5o parts boric acid and 3o parts dextrose in 25o parts 15 parts of aniline are entered into glycerine. The aniline dissolves quickly even with ordinary ones Temperature. The clear solution obtained can be diluted with water without becoming to tarnish.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB19495A DE921266C (en) | 1952-03-14 | 1952-03-14 | Solvents and neutralizers for amines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB19495A DE921266C (en) | 1952-03-14 | 1952-03-14 | Solvents and neutralizers for amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE921266C true DE921266C (en) | 1954-12-13 |
Family
ID=6960066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB19495A Expired DE921266C (en) | 1952-03-14 | 1952-03-14 | Solvents and neutralizers for amines |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE921266C (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB511645A (en) * | 1937-07-07 | 1939-08-22 | Talalmanykifejleszto Es Erteke | Improvements in or relating to turbo-compressors or pumps |
-
1952
- 1952-03-14 DE DEB19495A patent/DE921266C/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB511645A (en) * | 1937-07-07 | 1939-08-22 | Talalmanykifejleszto Es Erteke | Improvements in or relating to turbo-compressors or pumps |
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