Synthetic method of diacetylmonoxime

A synthetic method and technology of butanone oxime, which is applied in the field of methyl ethyl ketone ammonia oxime to produce butanone oxime, can solve the problems of uneconomical process, large environmental pollution, inconvenient operation, etc.

Active Publication Date: 2012-06-27
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method still has the disadvantages of low yield and the use of dangerous and highly corrosive sulfuric acid, which is inconvenient to operate.
In addition, about 4 tons of low-value by-product ammonium sulfate and nitrogen oxide emissions are produced for every ton of butanone oxime produced. Not only is the process uneconomical, but the production of NOx and Sox is also very polluting to the environment.
[0010] (Chemical Industry and Engineering, 2005, 25 (4): 279) have reported that adopting TS-1 is a catalyzer, methyl ethyl ketone, ammoniacal liquor, hydrogen peroxide are the method for reaction raw material one-step oxidation synthesis butanone oxime, but because this method must be The selectivity of the product can only be improved in the case of a large excess of ammonia water, and titanium silicon molecular sieve is afraid of alkali, if the excess of ammonia water is too much, it is easy to dissolve the Si of the skeleton, causing the loss of Ti and deactivation of the catalyst
Though (CN1556096A, CN 1651405 A, CN 1706818 A) improve this method to some extent, still exist hydrogen peroxide cost height and because H 2 o 2 Extremely unstable, will decompose when exposed to heat, light, rough surface, heavy metals and other impurities, corrosive, special safety measures should be taken in packaging, storage and transportation, etc.

Method used

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  • Synthetic method of diacetylmonoxime
  • Synthetic method of diacetylmonoxime
  • Synthetic method of diacetylmonoxime

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Get 20 grams of titanium-silicon molecular sieve TS-1, concentration is 0.01g / ml (as palladium atom) ammonium nitrate palladium complex solution and appropriate amount of hydrazine hydrate and cetyltrimethylammonium bromide are added to tetrapropyl Aqueous solution of ammonium hydroxide (mass percentage concentration 10%) stirs and mixes evenly, wherein titanium silicon molecular sieve (gram): hexadecyltrimethylammonium bromide (mole): tetrapropyl ammonium hydroxide (mole): hydrated Hydrazine (mol): ammonium nitrate palladium complex (g, calculated as palladium): water (mol) = 100: 0.005: 0.5: 3.0: 2.0: 1000. Then put it into a stainless steel sealed reaction kettle, hydrothermally treat it at a temperature of 150°C and autogenous pressure for 48 hours, filter the resultant, wash with water, dry it naturally, and continue drying at 180°C for 3 hours to obtain the novel compound containing Noble metal microporous titanium silicon material A. After characterization, its ...

Embodiment 2

[0080] Get 20 grams of titanium-silicon molecular sieve TS-1, a palladium chloride solution with a concentration of 0.01 g / ml (in terms of palladium atoms), and an appropriate amount of hydrazine hydrochloride and polypropylene to join in an aqueous solution of sodium hydroxide (mass percentage concentration 15%) and stir Mix well, wherein titanium silicon molecular sieve (gram): polypropylene (mol): sodium hydroxide (mol): hydrazine hydrochloride (mol): palladium chloride (gram, in palladium): water (mol) = 100: 0.9: 1.8:0.15:0.1:4600. Then put it into a stainless steel sealed reaction kettle, hydrothermally treat it at a temperature of 180°C and autogenous pressure for 24 hours, filter the resultant, wash with water, dry it naturally, and continue to dry it at 110°C for 3 hours to obtain the novel containing Noble metal microporous titanium silicon material B. After characterization, its composition can be expressed as 8TiO in the form of oxides 2 100SiO2 2 ·0.006PdO·0.00...

Embodiment 3

[0082] Tetraethyl orthosilicate, tetrabutyl titanate, palladium acetate solution and Tween 80 with a concentration of 0.01 g / ml (in terms of palladium atoms) were added to the aqueous solution of tetrapropylammonium hydroxide and butylenediamine (mass The percentage concentration is 10%) and stir and mix evenly, wherein the molar composition silicon source: titanium source: tetrapropylammonium hydroxide: butylenediamine: palladium source: protective agent: water = 100: 0.03: 0.5: 0.1: 0.05: 0.02:550, silicon source is SiO 2 In terms of titanium source as TiO 2 In terms of palladium source in terms of Pd. Then put it into a sealed reactor, hydrothermally treat it at a temperature of 120°C and autogenous pressure for 120 hours, take out the resultant, filter it, dry it, and roast it to obtain an intermediate crystalline material. Transfer the intermediate crystalline material to the above remaining filtrate, add an appropriate amount of hydrazine hydrate, and then conduct a hy...

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Abstract

The invention discloses a synthetic method of diacetylmonoxime, which is characterized in that under the conditions that the temperature is 0-180 DEG C and the pressure is 0.1-3.0 MPa, ethyl methyl ketone, ammonia, oxygen, hydrogen, diluent gas and solvent are contacted with catalyst, wherein the mol ratio of the ethyl methyl ketone, the ammonia, the oxygen, the hydrogen and the diluent gas is 1:(0.1-10.0) : (0.1-10.0) : (0.1-10.0) : (0-100), and the mass ratio of the solvent and the catalyst is (20-1000) : 1; the catalyst is a micropore titanium silicon material or a composition containing the micropore titanium silicon material, the component of the micropore titanium silicon material is expressed by an oxide form as xTiO2.100SiO2.yEmOn.zE, wherein the value of x is 0.001-50.0, the value of (y-z) is 0.005-20.0, and y / z is less than 1; E is one or more selected from noble metals of Ru, Rh, Pd, Re, Os, Ir, Ag, Pt and Au, and m and n are numbers which satisfy the requirements of E oxidation state; and the material crystal grains comprise hollow or concave-convex structures. The invention has high diacetylmonoxime selectivity, long stable running time and low cost and is environment-friendly.

Description

technical field [0001] The present invention relates to a method for ammoximation, and more particularly relates to a method for ammoximating methyl ethyl ketone to generate butanone oxime. Background technique [0002] Butanone oxime, also known as 2-butanone oxime (Methyl ethyl ketoxime; 2-butanon oxime), is an important fine chemical product. Because its toxicity and anti-skinning properties are superior to traditional acetone oxime and cyclohexanone oxime, it is widely used as an antioxidant and anti-skinning agent for paints. It can prevent easily oxidized drying materials from being oxidized in the air. It is mainly used It is used for skinning treatment of polyurethane paint and various alkyd resin paints during storage. It is also widely used as an oxygen scavenger for boiler water supply in large-scale thermal power plants, replacing hydrazine hydrate and acetone oxime that are toxic to humans; in addition, it is also used as an intermediate in organic synthesis to...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C259/06B01J29/89
Inventor 林民史春风朱斌舒兴田慕旭宏罗一斌汪燮卿汝迎春
Owner CHINA PETROLEUM & CHEM CORP
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