DK162831B - STABILIZED SOLUTIONS OF HYDROXYLAMINE OR SALTS THEREOF, AND METHOD FOR PREPARING THESE - Google Patents
STABILIZED SOLUTIONS OF HYDROXYLAMINE OR SALTS THEREOF, AND METHOD FOR PREPARING THESE Download PDFInfo
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- DK162831B DK162831B DK570184A DK570184A DK162831B DK 162831 B DK162831 B DK 162831B DK 570184 A DK570184 A DK 570184A DK 570184 A DK570184 A DK 570184A DK 162831 B DK162831 B DK 162831B
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- stabilized
- hydroxylamine
- salts
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- flavones
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/14—Hydroxylamine; Salts thereof
- C01B21/149—Stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/08—Acetic acid
- C07C53/10—Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/122—Propionic acid
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
DK 162831 BDK 162831 B
Opfindelsen angår stabiliserede opløsninger af hydro-xylamin eller dennes salte i vand eller alkoholer samt en fremgangsmåde til fremstilling disse.The invention relates to stabilized solutions of hydroxylamine or its salts in water or alcohols and to a process for their preparation.
Opløsninger af hydroxylammoniumsalte sønderdeles langsomt 5 ved stuetemperatur og hurtigere ved forhøjet temperatur.Solutions of hydroxylammonium salts decompose slowly at room temperature and more rapidly at elevated temperature.
Dette gælder i højere grad for opløsninger af fri hydr-oxylamin. Det har ikke manglet på forsøg på stabilisering af opløsninger af hydroxylamin og salte af denne med henblik på tilvejebringelse af forbedrede opbeva-10 ringsegenskaber. Ifølge US PS 3 344 270 anvendes urin stofderivater som stabiliseringsmiddel. Ifølge US PS 3 480 391 anvendes amidoximer og ifølge US PS 3 480 392 hydroxamsyrer til samme formål. Endelig er anvendelse af chelatdannende midler, såsom natriumsaltet af ethylen-15 diamintetraeddikesyre, som stabiliseringsmiddel kendt fra US PS 3 145 082. Det er imidlertid ønskeligt at tilvejebringe stabiliseringsmidler, der er mere effektive end de hidtil anvendte.This is more true for solutions of free hydroxylamine. It has not been lacking in attempts to stabilize solutions of hydroxylamine and its salts to provide improved storage properties. According to US PS 3,344,270, urine substance derivatives are used as a stabilizing agent. According to US PS 3 480 391, amidoximes and according to US PS 3 480 392 hydroxamic acids are used for the same purpose. Finally, the use of chelating agents, such as the sodium salt of ethylene-diamine tetraacetic acid, as a stabilizing agent is known from US PS 3,148,082. However, it is desirable to provide stabilizers which are more effective than those previously used.
Den til grund for opfindelsen liggende opgave går ud 20 på at tilvejebringe stabiliserede opløsninger af hydroxyl amin eller dennes salte, der er stabile gennem et længere tidsrum og især udmærker sig ved en minimal sønderdeling af fri hydroxylamin.The object of the invention is to provide stabilized solutions of hydroxyl amine or its salts which are stable over a long period of time and are particularly distinguished by a minimal decomposition of free hydroxylamine.
Denne opgave løses ifølge opfindelsen ved stabiliserede 25 opløsninger af hydroxylamin eller dennes salte i vand eller alkoholer, som er ejendommelige ved, at de indeholder flavoner med formlen R1* p' Vv r5This problem is solved according to the invention by stabilized solutions of hydroxylamine or its salts in water or alcohols, which are characterized by containing flavones of the formula R1 * p 'Vv r5
DK 162831 BDK 162831 B
2 hvori R"*- - hver betyder et hydrogenatom, en hydroxyl-gruppe, en (C^-C^)alkoxygruppe eller en (C^-C^)acyl-oxygruppe, idet mindst én substituent er en hydroxyl-gruppe.2 wherein R "- each represents a hydrogen atom, a hydroxyl group, a (C C-CC) alkoxy group or a (C ^-C ^) acyl oxy group, at least one substituent being a hydroxyl group.
5 Opfindelsen angår endvidere en fremgangsmåde til frem stilling af stabiliserede opløsninger af hydroxylamin eller dennes salte ved tilsætning af stabilisatorer, som er ejendommelig ved, at man fjerner det i opløst form tilstedeværende molekylære oxygen fra de opløs-10 ninger, som ønskes stabiliseret, ved behandling med nitrogen, som ikke indeholder molekylær oxygen, og derpå tilsætter flavoner, der er substitueret med mindst én hydroxylgruppe.The invention further relates to a process for preparing stabilized solutions of hydroxylamine or its salts by adding stabilizers which are characterized by removing the molecular oxygen present in the dissolved form from the solutions which are desired to be stabilized by treatment. with nitrogen which does not contain molecular oxygen, and then adds flavones substituted by at least one hydroxyl group.
De ifølge opfindelsen stabiliserede opløsninger af hydr-15 oxylamin eller dennes salte udviser den fordel, at de er stabile gennem længere tid end de hidtil kendte stabiliserede opløsninger. Især er sønderdelingen af fri hydroxylamin reduceret til et minimum.The stabilized solutions of hydroxylamine or its salts according to the invention have the advantage of being stable for longer than the previously known stabilized solutions. In particular, the decomposition of free hydroxylamine is reduced to a minimum.
Ued fremstillingen af opløsningerne ifølge opfindelsen 20 går man ud fra opløsninger af hydroxylamin eller dennes salte i vand eller alkoholer, f.eks. alkanoler med 1 -4 carbonatomer. Egnede salte af hydroxylamin er f.eks. salte med stærke mineralsyrer, såsom svovlsyre, salpetersyre og saltsyre, eller med fede syrer, f.eks. eddike-25 syre eller propionsyre. På grund af de forskellige oplø seligheder foreligger hydroxylamin fortrinsvis opløst i vand eller alkoholer, medens saltene fortrinsvis foreligger som vandige opløsninger. Indholdet af hydroxylamin eller dennes salte udgør som regel fra 10 til 70 30 vægt-?i. Udgangsopløsningerne har som regel en pH-værdi på 8 - 11. Særligt foretrukne er opløsninger af hydroxylamin i vand.In the preparation of the solutions of the invention 20, solutions of hydroxylamine or its salts in water or alcohols are used, e.g. alkanols having 1 -4 carbon atoms. Suitable hydroxylamine salts are e.g. salts with strong mineral acids such as sulfuric acid, nitric acid and hydrochloric acid, or with fatty acids, e.g. acetic acid or propionic acid. Because of the different solubilities, hydroxylamine is preferably dissolved in water or alcohols, while the salts are preferably present as aqueous solutions. The content of hydroxylamine or its salts usually ranges from 10 to 70 by weight. The starting solutions usually have a pH of 8 - 11. Particularly preferred are solutions of hydroxylamine in water.
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DK 162831 BDK 162831 B
**
Som stabilisatorer anvendes flavoner indeholdende mindst 1, fortrinsvis mindst 3 hydroxylgrupper i molekylet. Foretrukne flavoner er forbindelser med formlen R4Flavones containing at least 1, preferably at least 3 hydroxyl groups in the molecule are used as stabilizers. Preferred flavones are compounds of formula R4
r _^hyR5 Ir _ ^ hyR5 I
R2 0 hvori R"*· - R^ hver betyder et hydrogenatom, en hydroxyl-5 gruppe, en (C^-C^)alkoxygruppe eller en (C^-C^)acyloxy- gruppe, idet mindst én substituent er en hydroxylgruppe. Særligt foretrukne flavoner med formel (I) er forbindelser, hvori R·*" - R° hver betyder et hydrogenatom, en hydroxylgruppe eller en methoxygruppe, idet mindst 10 3 substituenter er hydroxylgrupper. De hydroxysubsti- tuerede flavoner kan også foreligge som glycosider.R2 is wherein R "* - R ^ each represents a hydrogen atom, a hydroxyl group, a (C ^-C ^) alkoxy group or a (C ^-C ^) acyloxy group, at least one substituent being a hydroxyl group Particularly preferred flavones of formula (I) are compounds wherein R R · - R ° each represents a hydrogen atom, a hydroxyl group or a methoxy group, wherein at least 10 3 substituents are hydroxyl groups. The hydroxy-substituted flavones may also be present as glycosides.
Egnede flavoner er f.eks.Suitable flavones are e.g.
3,3,7,2 ' ,4'-penta-hydroxy-flavon (morin) 3,5,7,3',4'-penta-hydroxy-flavon (quercetin) 15 3,5,7,3 ' ,41,5'-hexa-hydroxy-flavon (myricetin) 3,5,7,81,3',4’-hexa-hydroxy-flavon (gossypetin) 3,7,3',4',5'-penta-hydroxy-flavon (robinetin) 3,5,7,4'-tetra-hydroxy-flavon (kæmpferol) 5,7,3',4'-tetra-hydroxy-flavon (luteolin) 20 3,7,3',4'-tetra-hydroxy-flavon (fisetin) 5,7,4'-tri-hydroxy-flavon (apigenin) 3.5.7- tri-hydroxy-flavon (galgangin) 5.7- di-hydroxy-flavon (chrysin) og 3-mono-hydroxy-flavon (flavonol).3,3,7,2 ', 4'-penta-hydroxy-flavone (morphine) 3,5,7,3', 4'-penta-hydroxy-flavone (quercetin) 3,5,7,3 ', 41,5'-hexa-hydroxy-flavone (myricetin) 3,5,7,81,3 ', 4'-hexa-hydroxy-flavone (gossypetin) 3,7,3', 4 ', 5'-penta. hydroxy-flavone (robinetin) 3,5,7,4'-tetra-hydroxy-flavone (giant pyrol) 5,7,3 ', 4'-tetra-hydroxy-flavone (luteolin) 3,7,3', 4 '-tetra-hydroxy-flavone (fisetin) 5,7,4'-tri-hydroxy-flavone (apigenin) 3.5,7-tri-hydroxy-flavone (galgangin) 5.7-di-hydroxy-flavone (chrysin) and 3- monohydroxy-flavone (flavonol).
25 De hydroxysubstituerede flavoner anvendes fortrinsvis i en mængde fra 0,005 til 1 vægt-?o, især fra 0,01 til 0,1 vægt-?o, beregnet på den opløsning, som ønskes stabiliseret. Det har endvidere vist sig fordelagtigt atThe hydroxy-substituted flavones are preferably used in an amount of from 0.005 to 1% by weight, especially from 0.01 to 0.1% by weight, based on the solution desired to be stabilized. Furthermore, it has proved advantageous to
DK 162831 BDK 162831 B
4 medanvende polyhydroxybenzener, især pyrogallol. Poly-hydroxybenzenerne tilsættes fortrinsvis i mængder fra 0,005 til 1 vægt-%, beregnet på den opløsning, som ønskes stabiliseret. Det er bemærkelsesværdigt, at der tilveje-5 bringes en synergistisk virkning ved kombineret anvendel se af hydroxylsubstituerede flavoner og polyhydroxybenzener .4 co-existing polyhydroxybenzenes, especially pyrogallol. The polyhydroxybenzenes are preferably added in amounts of 0.005 to 1% by weight, based on the solution desired to be stabilized. It is noteworthy that a synergistic effect is produced by the combined use of hydroxyl-substituted flavones and polyhydroxybenzenes.
Stabiliserede opløsninger af hydroxylamin eller dennes salte i vand eller alkoholer fremstilles ifølge opfin-10 delsen på følgende måde: først fortrænges det i opløst form tilstedeværende molekylære oxygen fra de opløsninger, som ønskes stabiliseret, ved behandling med nitrogen, som ikke indeholder molekylær oxygen. Denne behandling kan f.eks. gennemføres ved gennemledning af oxygen-15 fri nitrogen, f.eks. i 5 - 10 minutter. Det anvendte nitrogen indeholder fortrinsvis mindre end 2 ppm O2.Stabilized solutions of hydroxylamine or its salts in water or alcohols are prepared according to the invention as follows: first, the dissolved molecular oxygen present in the solution is desired to be displaced from the solutions which are desired to be stabilized by treatment with nitrogen which does not contain molecular oxygen. This treatment may e.g. is carried out by passing oxygen-free nitrogen, e.g. for 5 - 10 minutes. The nitrogen used preferably contains less than 2 ppm O 2.
Derefter tilsættes hydroxysubstitueret flavon samt eventuelt polyhydroxybenzener, og disse opløses i den opløsning, som ønskes stabiliseret. Det er også muligt at 20 tilsætte stabilisatorerne i opløst tilstand.Then hydroxy-substituted flavone and optionally polyhydroxybenzenes are added and dissolved in the solution which is desired to be stabilized. It is also possible to add the stabilizers in the dissolved state.
De her omhandlede tilsætningsstoffer giver en fordelagtig stabilisering af vandige opløsninger ved 5-40 °C.The present additives provide an advantageous stabilization of aqueous solutions at 5-40 ° C.
Det er klart, at det er fordelagtigt at undgå kontamine-25 ring af opløsningerne med tungmetaller, især kobber eller ædelmetaller, da disse katalyserer sønderdelingen af hydroxylamin. Det er endvidere fordelagtigt at udelukke energirige stråler ved anvendelse af passende farvede glasbeholdere. Endelig er det fordelagtigt at 30 opbevare de stabiliserede opløsninger ved temperaturer mindre end 40 °C, f.eks. ved temperaturer på 5 - 20 °C.Obviously, it is advantageous to avoid contamination of the solutions with heavy metals, especially copper or precious metals, as these catalyze the decomposition of hydroxylamine. Furthermore, it is advantageous to exclude energy-rich rays using suitably colored glass containers. Finally, it is advantageous to store the stabilized solutions at temperatures less than 40 ° C, e.g. at temperatures of 5 - 20 ° C.
55
DK 162831 BDK 162831 B
De stabiliserede opløsninger af hydroxylamin eller dennes salte er egnet til fremstilling af oximer.The stabilized solutions of hydroxylamine or its salts are suitable for the production of oxymers.
I det følgende belyses opfindelsen nærmere ved hjælp af en række eksempler.In the following, the invention is further elucidated by means of a number of examples.
5 EKSEMPEL 1 og SAMMENLIGNINGSEKSEMPEL 1 og 2EXAMPLE 1 and COMPARATIVE EXAMPLES 1 and 2
En vandig opløsning af ca. 10 vægt-?0 hydroxylamin blev behandlet med oxygenfri nitrogen i 10 minutter ved 20 °C, hvorefter stabilisatoren blev tilsat. Hydroxylamin-koncentration, tilsat mængde og art af stabilisatoren 10 samt de af tid og temperatur afhængige resultater fremgår af nedenstående tabel 1.An aqueous solution of approx. 10 wt-O hydroxylamine was treated with oxygen-free nitrogen for 10 minutes at 20 ° C, after which the stabilizer was added. Hydroxylamine concentration, amount and type of stabilizer 10 added, as well as the time and temperature dependent results are shown in Table 1 below.
TABEL 1TABLE 1
Stabilisator Tid (timer) 0 20 112 287 668Stabilizer Time (hours) 0 20 112 287 668
Eksempel 1 Morin 100,5* 100,15* - 99,66* 99,33* 0,02 vægt-%Example 1 Morin 100.5 * 100.15 * - 99.66 * 99.33 * 0.02% by weight
Sammenligningseksempel 1 - 138,5* 134,8* - 105,6* 76,6*Comparative Example 1 - 138.5 * 134.8 * - 105.6 * 76.6 *
Sammenligningseksempel 2 Pyrogallol 101,0* 99,9* 97,0* 96,2* 94,5*Comparative Example 2 Pyrogallol 101.0 * 99.9 * 97.0 * 96.2 * 94.5 *
0,005 vægt-S0.005 weight-S
Mængde N^OH (g/1) EKSEMPEL 2-4Amount of N 2 OH (g / l) EXAMPLES 2-4
Man gik frem som beskrevet i eksempel 1. Hydroxylamin-koncentration, tilsat mængde og art af stabilisator 15 samt de af tid og temperatur afhængige resultater fremgår af nedenstående tabel 2.Proceed as described in Example 1. Hydroxylamine concentration, added amount and nature of stabilizer 15, and the time and temperature dependent results are shown in Table 2 below.
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DK 162831 BDK 162831 B
TABEL 2TABLE 2
Eksempel Stabilisator “CExample Stabilizer “C
0 743 1195 timer0 743 1195 hours
2 50 ppm Morin + 5 110,55 110,48 110,05 g/i nh OH2 50 ppm Morin + 5 110.55 110.48 110.05 g / l nh OH
50 ppm Pyrogallol ^ 0 404 1195 timer50 ppm Pyrogallol ^ 0 404 1195 hours
" 20 110,25 110,06 109,89 g/1 1IH20H110.25 110.06 109.89 g / l 1 H 2 OH
0 359 1194 timer0 359 1194 hours
" 40 110,25 109,73 108,08 g/1 NH20H40.25.25 109.73 108.08 g / l NH 2 OH
3 50 ppm Quercetin 0 384 526 timer3 50 ppm Quercetin 0 384 526 hours
5 136,95 136,62 136,46 g/1 HH20H136.66 136.66 g / l HH 2 OH
0 384 523 timer0 384 523 hours
" 20 136,95 135,96 135,63 g/1 KH20H136.96 135.96 135.63 g / l KH 2 OH
0 384 522 timer0 384 522 hours
" 40 136,95 135,96 135,63 g/1 HH20H40 136.95 135.96 135.63 g / l HH 2 OH
0 162 . 1656 timer0 162. 1656 hours
4 Morin 25 473,55 454,08 414,15 g/1 HH20S4 Morin 473.55 454.08 414.15 g / l HH 2 OS
25 mg/aol KH2®^25 mg / aol KH2® ^
Claims (6)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3343597 | 1983-12-02 | ||
| DE19833343597 DE3343597A1 (en) | 1983-12-02 | 1983-12-02 | STABILIZED SOLUTIONS OF HYDROXYLAMINE OR THEIR SALT IN WATER OR ALCOHOLS AND THEIR PRODUCTION |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| DK570184D0 DK570184D0 (en) | 1984-11-30 |
| DK570184A DK570184A (en) | 1985-06-03 |
| DK162831B true DK162831B (en) | 1991-12-16 |
| DK162831C DK162831C (en) | 1992-05-04 |
Family
ID=6215846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK570184A DK162831C (en) | 1983-12-02 | 1984-11-30 | STABILIZED SOLUTIONS OF HYDROXYLAMINE OR SALTS THEREOF, AND METHOD FOR PREPARING THESE |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0151249B1 (en) |
| JP (1) | JPS60137809A (en) |
| DE (2) | DE3343597A1 (en) |
| DK (1) | DK162831C (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200940706A (en) | 2007-10-29 | 2009-10-01 | Ekc Technology Inc | Methods of cleaning semiconductor devices at the back end of line using amidoxime compositions |
| US8802609B2 (en) | 2007-10-29 | 2014-08-12 | Ekc Technology Inc | Nitrile and amidoxime compounds and methods of preparation for semiconductor processing |
| US7838483B2 (en) | 2008-10-29 | 2010-11-23 | Ekc Technology, Inc. | Process of purification of amidoxime containing cleaning solutions and their use |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3145082A (en) * | 1959-12-07 | 1964-08-18 | Dow Chemical Co | Stabilized hydroxylamine and its method of preparation |
| US3480392A (en) * | 1967-08-24 | 1969-11-25 | Sinclair Research Inc | Hydroxylamine solutions stabilized with a hydroxamic acid and method for their preparation |
| US3480391A (en) * | 1967-08-24 | 1969-11-25 | Sinclair Research Inc | Hydroxylamine solutions stabilized with an amide oxime and method for their preparation |
| US3544270A (en) * | 1968-08-13 | 1970-12-01 | Sinclair Oil Corp | Aqueous hydroxylamine solutions stabilized with hydroxyurea or hydroxythiourea derivatives |
-
1983
- 1983-12-02 DE DE19833343597 patent/DE3343597A1/en not_active Withdrawn
-
1984
- 1984-11-26 DE DE8484114251T patent/DE3466522D1/en not_active Expired
- 1984-11-26 EP EP84114251A patent/EP0151249B1/en not_active Expired
- 1984-11-30 DK DK570184A patent/DK162831C/en not_active IP Right Cessation
- 1984-11-30 JP JP59252108A patent/JPS60137809A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK570184A (en) | 1985-06-03 |
| DK570184D0 (en) | 1984-11-30 |
| EP0151249A2 (en) | 1985-08-14 |
| DE3466522D1 (en) | 1987-11-05 |
| EP0151249A3 (en) | 1986-02-12 |
| DK162831C (en) | 1992-05-04 |
| JPS60137809A (en) | 1985-07-22 |
| DE3343597A1 (en) | 1985-06-13 |
| EP0151249B1 (en) | 1987-09-30 |
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