CN101318912A - Process for preparing butanone oxime - Google Patents
Process for preparing butanone oxime Download PDFInfo
- Publication number
- CN101318912A CN101318912A CNA2008101200368A CN200810120036A CN101318912A CN 101318912 A CN101318912 A CN 101318912A CN A2008101200368 A CNA2008101200368 A CN A2008101200368A CN 200810120036 A CN200810120036 A CN 200810120036A CN 101318912 A CN101318912 A CN 101318912A
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- CN
- China
- Prior art keywords
- diacetylmonoxime
- preparation
- hydrogen peroxide
- butanone
- ammonia
- 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.)
- Pending
Links
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 30
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- FSEUPUDHEBLWJY-HWKANZROSA-N diacetylmonoxime Chemical compound CC(=O)C(\C)=N\O FSEUPUDHEBLWJY-HWKANZROSA-N 0.000 claims description 22
- 239000002808 molecular sieve Substances 0.000 claims description 10
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 2
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 abstract 3
- 238000005516 engineering process Methods 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method for methylethylketoxime. The method is as follows: under the action of catalyst, the methylethylketoxime is produced by reacting butanone with hydrogen peroxide and ammonia in water, according to a molar ratio of the butanone to the hydrogen peroxide to the mole of the ammonia of 1:0.8-1.5:1-3.5, which is carried out at a temperature of between 55 and 80 DEG C, under the atmospheric pressure for 1 to 3 hours. The method for preparing the methylethylketoxime is characterized by moderate reaction conditions and environment protection, no requirement of an organic solvent, etc.
Description
Technical field
The present invention relates to a kind of preparation method of organic compound Diacetylmonoxime.
Background technology
Structural formula Diacetylmonoxime as shown in Equation 1 is a kind of chemosynthesis intermediate, and it is the important source material of synthetic neutral linking agent methyl tributanoximo silane, vinyl tributanoximo silane, also can be used as the anti of boiler deoxidant and paint, coating etc.
Formula 1
The preparation method of Diacetylmonoxime mainly contains hydroxylamine assay and TS-1 molecular sieve catalytic oxidation proceses of ammonia, the existing TS-1 molecular sieve catalytic of document oxidation proceses of ammonia has been used organic solvent in reaction process, and need pressurization to react (Chemical industry and engineering, 2005, Vol.22, NO.4,279～281), this makes the energy consumption of this technology and separation costs increase.
Summary of the invention
The problem to be solved in the present invention provides a kind ofly not to be needed with an organic solvent, the preparation method of reaction conditions gentleness, eco-friendly Diacetylmonoxime.
In order to solve the problems of the technologies described above, the invention provides a kind of preparation method of Diacetylmonoxime, under the effect of catalyzer, butanone and hydrogen peroxide and ammonia react generate Diacetylmonoxime in water; Reaction times is 1～3 hour, and temperature is 55～80 ℃, and the mol ratio of butanone, hydrogen peroxide, ammonia is 1: 0.8～1.5: 1～3.5, and reaction pressure is a normal pressure.
Improvement as the preparation method of Diacetylmonoxime of the present invention: catalyzer is the TS-1 molecular sieve that contains active ingredient, and the consumption of active ingredient is 5～10% of a butanone quality.
Further improvement as the preparation method of Diacetylmonoxime of the present invention: active ingredient is the skeleton titanium.
Further improvement as the preparation method of Diacetylmonoxime of the present invention: active ingredient accounts for 1～2.5% of TS-1 molecular sieve gross weight.
Further improvement as the preparation method of Diacetylmonoxime of the present invention: hydrogen peroxide is that mass concentration is 20～35% hydrogen peroxide.
Further improvement as the preparation method of Diacetylmonoxime of the present invention: ammonia is that mass concentration is 15～30% ammoniacal liquor.
Reaction formula of the present invention is as follows:,
Used catalyzer is the TS-1 molecular sieve in the reaction process, and its preparation method can be referring to Journal ofmolecular catalysis, 1996, Vol.10, NO.1,25～31.
Among the present invention, more excellent catalyst levels is: the mass ratio of active ingredient and butanone is 6.5%, and more excellent hydrogen peroxide concentration is 25～30%, and more excellent ammonia concn is 20～25%, and more excellent temperature of reaction is 65 ℃.
The preparation method of Diacetylmonoxime of the present invention does not need to add organic solvent, and the feature of environmental protection is good; Reaction pressure is a normal pressure, can make whole technology more succinct, convenient; Help reducing cost.
The product that employing the inventive method makes is defined as Diacetylmonoxime through gas chromatogram and standard specimen comparison and detection.With low cost, the environmental friendliness of this method, yield can be up to 70.3%.
Embodiment
The preparation method of embodiment 1, a kind of Diacetylmonoxime is a raw material with butanone, ammoniacal liquor, hydrogen peroxide, and operation steps is:
In volume is the still of 250mL, add TS-1 molecular sieve (including the Ti of 1.0g) as catalyzer, Ti content in the TS-1 molecular sieve is 1.5%; Add the 20mL water as solvent again.With 20mL butanone (0.22mol, 16.1g), the 40mL massfraction is 25% the disposable charging of ammoniacal liquor (0.53mol), after being heated to 65 ℃ of temperature of reaction, add the hydrogen peroxide 30mL (0.24mol) of massfraction 25% with the speed of 30g/h, keeping temperature of reaction during this period is 65 ℃.Under 65 ℃ temperature of reaction and non-pressurized reaction pressure, react and finish reaction after 1.5 hours; With gas chromatographic analysis still liquid.Analysis revealed, pimelinketone transformation efficiency are 71.7%, and yield is 70.3%.
Embodiment 2～5:
Change the following reaction conditions among the embodiment 1: the volumetric usage (being called for short V2) of the volumetric usage (being called for short V1) of the weight of Ti content (abbreviation active component content), Ti in the TS-1 molecular sieve (being called for short m1), temperature of reaction (being called for short T), hydrogen peroxide, the mass concentration (being called for short w1) of hydrogen peroxide, ammoniacal liquor, the mass concentration (being called for short w2) of ammoniacal liquor, reaction times (being called for short t), obtain embodiment 2～5, thereby obtain transformation efficiency (being called for short x), the product yield (being called for short y) of corresponding butanone.Particular content and data results see Table 1.
Table 1
| Embodiment number | 1 | 2 | 3 | 4 | 5 |
| Active component content (%) | 1.5 | 1.0 | 2.0 | 2.5 | 1.5 |
| m1(g) | 1.0 | 1.5 | 1.6 | 1.2 | 1.4 |
| T(℃) | 65 | 75 | 65 | 70 | 55 |
| V1(mL) | 30 | 35 | 30 | 20 | 25 |
| w1(％) | 25 | 20 | 30 | 35 | 25 |
| V2(mL) | 40 | 40 | 55 | 25 | 30 |
| w2(％) | 25 | 20 | 15 | 30 | 20 |
| t(h) | 1.5 | 1 | 2 | 2.5 | 3 |
| x | 71.7％ | 65.3％ | 70.2％ | 64.7％ | 55.2％ |
| y | 70.3％ | 64.0％ | 69.0％ | 61.6％ | 47.9％ |
At last, it is also to be noted that what more than enumerate only is several specific embodiments of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be arranged.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention all should be thought protection scope of the present invention.
Claims (6)
1, a kind of preparation method of Diacetylmonoxime is characterized in that: under the effect of catalyzer, butanone and hydrogen peroxide and ammonia react generate Diacetylmonoxime in water; Reaction times is 1～3 hour, and temperature is 55～80 ℃, and the mol ratio of butanone, hydrogen peroxide, ammonia is 1: 0.8～1.5: 1～3.5, and reaction pressure is a normal pressure.
2, the preparation method of Diacetylmonoxime according to claim 1 is characterized in that: described catalyzer is the TS-1 molecular sieve that contains active ingredient, and the consumption of active ingredient is 5～10% of a butanone quality.
3, the preparation method of Diacetylmonoxime according to claim 2 is characterized in that: described active ingredient is the skeleton titanium.
4, the preparation method of Diacetylmonoxime according to claim 3 is characterized in that: described active ingredient accounts for 1～2.5% of TS-1 molecular sieve gross weight.
5, the preparation method of Diacetylmonoxime according to claim 4 is characterized in that: described hydrogen peroxide is that mass concentration is 20～35% hydrogen peroxide.
6, the preparation method of Diacetylmonoxime according to claim 5 is characterized in that: described ammonia is that mass concentration is 15～30% ammoniacal liquor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008101200368A CN101318912A (en) | 2008-07-15 | 2008-07-15 | Process for preparing butanone oxime |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008101200368A CN101318912A (en) | 2008-07-15 | 2008-07-15 | Process for preparing butanone oxime |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101318912A true CN101318912A (en) | 2008-12-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008101200368A Pending CN101318912A (en) | 2008-07-15 | 2008-07-15 | Process for preparing butanone oxime |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103864643A (en) * | 2014-03-04 | 2014-06-18 | 华东师范大学 | Preparation method of oxime |
| CN104860842A (en) * | 2015-05-13 | 2015-08-26 | 南京工业大学 | Solvent-free green ammoximation process based on membrane distribution |
| US9133106B2 (en) | 2012-12-25 | 2015-09-15 | China Petrochemical Development Corporation | Method for producing ketoxime |
| CN110407716A (en) * | 2019-08-16 | 2019-11-05 | 山东省化工研究院 | A kind of method that oximate process inhibits nitroparaffins |
| CN111501346A (en) * | 2020-05-13 | 2020-08-07 | 常州雅美特窗饰股份有限公司 | Method for preventing curtain coating slurry from coagulating |
| CN115872896A (en) * | 2022-12-05 | 2023-03-31 | 衢州巨化锦纶有限责任公司 | Preparation method for producing butanone oxime by using nickel-doped titanium silicalite molecular sieve |
-
2008
- 2008-07-15 CN CNA2008101200368A patent/CN101318912A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9133106B2 (en) | 2012-12-25 | 2015-09-15 | China Petrochemical Development Corporation | Method for producing ketoxime |
| CN103864643A (en) * | 2014-03-04 | 2014-06-18 | 华东师范大学 | Preparation method of oxime |
| CN103864643B (en) * | 2014-03-04 | 2015-11-18 | 华东师范大学 | A kind of preparation method of oxime |
| CN104860842A (en) * | 2015-05-13 | 2015-08-26 | 南京工业大学 | Solvent-free green ammoximation process based on membrane distribution |
| WO2016179910A1 (en) * | 2015-05-13 | 2016-11-17 | 南京工业大学 | Solvent-free green ammoximation process based on film distribution |
| CN110407716A (en) * | 2019-08-16 | 2019-11-05 | 山东省化工研究院 | A kind of method that oximate process inhibits nitroparaffins |
| CN110407716B (en) * | 2019-08-16 | 2022-04-29 | 山东省化工研究院 | Method for inhibiting nitroalkane in oximation process |
| CN111501346A (en) * | 2020-05-13 | 2020-08-07 | 常州雅美特窗饰股份有限公司 | Method for preventing curtain coating slurry from coagulating |
| CN115872896A (en) * | 2022-12-05 | 2023-03-31 | 衢州巨化锦纶有限责任公司 | Preparation method for producing butanone oxime by using nickel-doped titanium silicalite molecular sieve |
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| PB01 | Publication | ||
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Application publication date: 20081210 |