Stabilization of hydroxylamine containing solutions and method for their preparation

A kind of hydroxylamine, stable technology, is used in stable hydroxylamine-containing solution and its preparation field

Inactive Publication Date: 2010-12-08
EKC TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] A problem with the present situation for formulators aiming at preparing a stable hydroxylamine-containing cleaning solution is that the cleaning solution is only selective for metal oxides and not for the metal itself, as in the case of metal applications such as copper

Method used

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  • Stabilization of hydroxylamine containing solutions and method for their preparation
  • Stabilization of hydroxylamine containing solutions and method for their preparation
  • Stabilization of hydroxylamine containing solutions and method for their preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0413] Example 2: Comparative example with US Patent No. 3,480,391.

[0414] Add 50ppm of FeCl to the hydroxylamine solution stabilized with various nitriles, amidoximes and hydroxamic acid compounds below 3 Solution. These solutions were placed in a water bath at 50°C for 24 hours. After 24 hours, the hydroxylamine concentration was analyzed by titration.

[0415]

[0416] result:

[0417] Test Results

[0418] All tested compounds provide further stability of hydroxylamine. Comparing the results of Example 1 with the results of Example 2, it is shown that the hydroxylamine sample of Example 1 decomposed about 30%. It was observed that nitriles with a molecular weight less than about 200 decompose hydroxylamine more than compound A07 (this compound reacts with acrylonitrile through ethylenediamine, and then is converted into amidoxime (its chemical name is 3,3',3",3"'- (Prepared by ethane-1,2-diylbis(azaalkyltriyl))tetra(N'-hydroxypropionamidine)).

Embodiment 3

[0421]

[0422] The solution containing the amidoxime molecule of 1,2,3,4,5,6-hexa-0-[3-(hydroxyamino)-3-iminopropylhexitol provides more than the solution without any stabilizer Better stability of cleaning solution.

Embodiment 4

[0424] The following nitrile compounds with different carbon numbers and molecular weights are introduced into the hydroxylamine free base solution. Extract 10 ml from each sample and add 100 microliters of Fe raw material (1000 ppm), the effective dose of Fe is 10 ppm. After 24 hours at 50°C, the samples were analyzed for HDA%. The results show that the nitrile compound reacts with hydroxylamine to form the corresponding amidoxime molecule. Even if 10 ppm iron is added to the solution, the hydroxylamine solution can be further stabilized.

[0425]

[0426]

[0427]

[0428] List of specific amidoxime compounds prepared from nitriles:

[0429] Nitrile

[0430] Cinnamonitrile

[0431] List of specific amidoxime compounds prepared from nitriles by cyanoethylation of nucleophilic compounds:

[0432] Nucleophilic compound

[0433] Pentaerythritol

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Abstract

The invention relates to the use of amidoximes for prevention of or stabilization of hydroxylamine compounds against undesired decomposition.

Description

Invention field [0001] The invention relates to a stable hydroxylamine-containing composition and a preparation method thereof. More specifically, the present invention relates to the use of amidoximes to stabilize hydroxylamine compounds to prevent undesirable decomposition. Background technique [0002] Aqueous hydroxylamine is widely used in chemical synthesis, but its instability greatly limits its application in reactions where storage and product purity are critical. When hydroxylamine-containing aqueous solutions are obtained through ion exchange technology, the problem of instability of these aqueous solutions is particularly serious. [0003] In the first ten years alone, there have been two incidents involving catastrophic explosions in the production process of hydroxylamine free alkali due to the presence of unstable hydroxylamine, leading to death. See figure 1 . [0004] Because Lee introduced hydroxylamine into the semiconductor cleaning process (see, for example, U...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C01B21/14
CPCH01L21/02041C11D3/32C11D11/0047G03F7/422C01B21/1445
Inventor W·M·李
Owner EKC TECH
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