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CN104549348A - Catalyst for synthesis of 2,6-dimethyl-4-heptanone from acetone and preparation method for catalyst - Google Patents

Catalyst for synthesis of 2,6-dimethyl-4-heptanone from acetone and preparation method for catalyst Download PDF

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CN104549348A
CN104549348A CN201310495783.0A CN201310495783A CN104549348A CN 104549348 A CN104549348 A CN 104549348A CN 201310495783 A CN201310495783 A CN 201310495783A CN 104549348 A CN104549348 A CN 104549348A
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acetone
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CN104549348B (en
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王春梅
苏杰
侯学伟
李风华
季秀珍
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China Petroleum and Chemical Corp
Sinopec Fushun Research Institute of Petroleum and Petrochemicals
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China Petroleum and Chemical Corp
Sinopec Fushun Research Institute of Petroleum and Petrochemicals
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Abstract

The invention discloses a catalyst for synthesis of 2,6-dimethyl-4-heptanone from acetone and a preparation method for the catalyst. The catalyst comprises an active ingredient Ni and a carrier ZrO12-MnO2; based on the total weight of the catalyst, the content of the active ingredient Ni is 1 to 10 weight percent, preferably 3 to 6 weight percent, the content of MnO2 is 1 to 20 weight percent, preferably 5 to 10 weight percent, and the balance is ZrO2. The catalyst disclosed by the invention is applied to a reaction for synthesis of the 2,6-dimethyl-4-heptanone from the acetone, and has the characteristics that conversion rate of the acetone serving as a raw material is high; the selectivity of the 2,6-dimethyl-4-heptanone serving as a product is high, that is the yield of the 2,6-dimethyl-4-heptanone serving as a target product is high.

Description

A kind of Catalysts and its preparation method of acetone synthesis diisobutyl ketone
Technical field
The present invention relates to catalyzer and the preparation method of a kind of acetone through one-step method synthesis diisobutyl ketone.
Background technology
Diisobutyl ketone is a kind of excellent solvent and chemical intermediate.The boiling point of diisobutyl ketone is high, velocity of evaporation is fast, solvency power is strong, can improve film levelling, gloss, recoatability, good to the wettability of plastic bottom material, increase sorptive force, available nitro sprays paint, the solvent of ethenoid resin paint and other synthetic resin coatings, can improve its moisture protection.Also can be used as manufacturing the dispersion agent of Organic aerosol and food and refine intermediate with solvent and some drugs, sterilant, also can be used on rare metal extraction and separating metal salt in purifying.
At present, about introducing the synthesis diisobutyl ketone report that is and few.Great majority are the methods introducing synthesize methyl-isobutyl ketone coproduction diisobutyl ketone.Totally see, if for the purpose of diisobutyl ketone product, its yield await improve.
CN101712606A discloses a kind of Ni/MgO-Al 2o 3zrO 2catalyzer, this catalyzer consists of: Ni:6wt%, MgO:60wt%, Al 2o 3: 21wt%, Ni:13wt%, catalyzer is obtained by NiMgAlZr four-component hydrotalcite compound.Acetone conversion is 60%, and the selectivity of diisobutyl ketone reaches 24%, and the yield of diisobutyl ketone is 14.4%.
CN102806085A discloses the catalyzer of a kind of acetone hydrogenation coproduction Virahol and diisobutyl ketone, and catalyzer comprises alumina supporter and load at γ-Al 2o 3ni, Mg on carrier, with the total weight of catalyzer, containing the Ni of 20 ~ 25%, the Mg of 8 ~ 12%.Acetone conversion is 92.8%, and the selectivity of diisobutyl ketone reaches 25.6%, and the yield of diisobutyl ketone is 23.8%.
CN1566060A discloses the processing method of a kind of Status of OneStep Synthesis of Methyl isoButyl Ketone from Acetone and diisobutyl ketone.The method uses Pd/ZrO 2as catalyzer, Pd content is 0.5wt%, normal pressure, fixed-bed reactor.When acetone conversion is 65.13%, the selectivity of diisobutyl ketone is up to 61.34%, and now the yield of diisobutyl ketone is 40.01%.
Document " Ni, Ni/Al 2o 3to acetone hydrogenation one-step synthesis methyl iso-butyl ketone (MIBK) Performance comparision " (SCI, o. 11th, 1865 pages in 1997) report, in the process of acetone hydrogenation one-step synthesis methyl iso-butyl ketone (MIBK), adopt Ni-Ce/Al 2o 3during catalyzer, the transformation efficiency of acetone is 81.7%, and the selectivity of diisobutyl ketone is 50.05%, and now the yield of diisobutyl ketone is up to 40.9%.
Summary of the invention
For the deficiencies in the prior art, a kind of acetone is the object of the present invention is to provide to synthesize the Catalysts and its preparation method of diisobutyl ketone, catalyzer of the present invention is used for acetone synthesis diisobutyl reactive ketone, there is raw material acetone transformation efficiency high, the selectivity of product diisobutyl ketone is good, i.e. the yield high of object product diisobutyl ketone.
The catalyzer of acetone synthesis diisobutyl ketone of the present invention, comprises active ingredient Ni and carrier ZrO 2-MnO 2, with overall catalyst weight gauge, active ingredient Ni for 1wt% ~ 10wt%, is preferably 3wt% ~ 6wt%, MnO in element content 2content be 1wt% ~ 20wt%, be preferably 5wt% ~ 10wt%, surplus is ZrO 2.
The preparation method of the catalyzer of acetone synthesis diisobutyl ketone of the present invention, comprises following content:
(1) be added drop-wise in alkaline solution by the mixing solutions of the soluble salt of the soluble salt containing zirconium and manganese, control ph is 8 ~ 11, dropwises, and stirs 15 ~ 60 minutes, aging, obtains Zr (OH) 4with Mn (OH) 2mixing water gel, washing, drying, roasting, shaping, obtain ZrO 2-MnO 2carrier;
(2) by ZrO that step (1) obtains 2-MnO 2carrier impregnation active ingredient Ni, dry, roasting obtains catalyst n i/ZrO 2-MnO 2; Wherein steeping fluid is the mixing solutions of the soluble salt containing ammonium salt and nickel.
In the inventive method, the soluble salt of the zirconium described in step (1) is zirconium oxychloride and zirconium nitrate, preferred zirconium oxychloride, and the soluble salt of manganese is manganous nitrate, manganous sulfate and Manganous chloride tetrahydrate, preferred Manganous chloride tetrahydrate.
In the inventive method, described solution is generally the aqueous solution, also can be C 4following alcoholic solution as methyl alcohol, ethanol, propyl alcohol or Virahol etc., or is the mixing solutions of water and alcohol.
In the inventive method, in the mixing solutions of Zr and the Mn described in step (1), metal content is 0.02 ~ 1.5mol/L, preferably 0.2 ~ 1.0mol/L, and concrete Zr and Mn concentration is determined according to Zr and Mn ratio in prepared catalyzer.
In the inventive method, it is aging that aging described in step (1) is generally normal temperature, and digestion time is 20 ~ 30 hours.
In the inventive method, Zr (OH) in step (1) 4with Mn (OH) 2mixing water gel with deionized water wash to without Cl -exist.
In the inventive method, the drying conditions described in step (1) is: drying 4 ~ 8 hours at 100 ~ 120 DEG C; Roasting condition is: roasting 6 ~ 10 hours at 200 ~ 500 DEG C.
In the inventive method, the carrier described in step (1) is shaping can drip ball forming, spin granulation, extrusion molding and compression molding etc., and support shapes is bar shaped (cylindrical, trilobal and quatrefoil etc.), spherical or sheet shape.
In the inventive method, the soluble salt of the described nickel described in step (2) is nitrate and acetate, and ammonium salt is the soluble salt of nitrate, vitriol, carbonate, acetate and muriate, the ammonium salt that preferred anionic is identical and nickel.
In the inventive method, the dipping time described in step (2) is 20 ~ 25 hours.
In the inventive method, the drying conditions described in step (2) is: 100 ~ 115 DEG C of dryings 3 ~ 4 hours; Roasting condition is: 300 ~ 500 DEG C of roastings 8 ~ 10 hours.
In the inventive method, in step (2) steeping fluid, the content of Ni counts 0.05 ~ 1.5mol/L with element, preferably 0.2 ~ 1.0mol/L; NH in steeping fluid 4 +content be 0.01 ~ 1.0mol/L, preferably 0.05 ~ 0.5mol/L.
In the inventive method, active component content is determined according to response situation.
Ni/ZrO of the present invention 2-MnO 2catalyst application is in acetone synthesis diisobutyl reactive ketone, and the general condition of reaction is: temperature of reaction 150 ~ 250 DEG C, preferably 150 ~ 200 DEG C, and reaction pressure is normal pressure, and acetone feed air speed is 0.25 ~ 2.5h -1(V), preferred 0.5 ~ 2.0h -1(V), H 2/ acetone (V/V) is 200 ~ 500, preferably 300 ~ 400.
Catalyzer of the present invention loads reactor before use, adopts reduction method reduction in device.Reductive condition is: reduction temperature is 300 DEG C, reduction pressure normal pressure, and the time is 5 ~ 8 hours, and the catalyzer after reduction completely cuts off air and preserves.
The present invention is by introducing metal M n in the carrier, and metal M n is finally with MnO 2state exist, effectively can stop the crystallite melting of W metal on carrier, better divided active component, thus improve the activity of catalyzer and stability.Meanwhile, MnO 2ketone is generated to alcohol oxidation and there is katalysis, so MnO in catalyzer 2existence inhibit the generation of by-product alcohol, be conducive to the selectivity improving object product diisobutyl ketone.And auxiliary agent Mn joins in carrier in the mode of co-precipitation, avoid Mn at carrier ZrO 2the absorption of upper formation eggshell, and the phenomenon causing active ingredient Ni to adsorb on carrier to be thus obstructed occurs, and adsorbs effectively in active ingredient Ni on carrier.In the present invention, complex catalyst precursor is impregnated in the nickel nitrate solution mixing solutions containing ammonium nitrate, makes Ni ion and NH 4 +catalyst precursor forms competitive adsorption, is conducive to the presoma that Ni can load to catalyzer more equably, thus improve transformation efficiency and the selectivity of catalyzer.
Embodiment
Below in conjunction with embodiment, the present invention is further described, but does not therefore limit the present invention.
embodiment 1
By 262g ZrOCl 28H 2o and 8g MnCl 24H 2o is dissolved in 1000mL deionized water, is made into mixing solutions.Mixing salt solution being added drop-wise to 800mL concentration is in 0.2mol/L ammonia soln, and dropping 0.2mol/L NaOH solution control ph is 11 simultaneously.Dropwise rear stirring 40 minutes, more aging 24 hours of static precipitation in mother liquor at normal temperatures, obtained Zr (OH) 4with Mn (OH) 2mixing water gel.Zr (OH) 4with Mn (OH) 2mixing water gel with deionized water wash to without Cl -exist, filter and be precipitated thing, throw out is dried 6 hours at 110 DEG C, and at 300 DEG C, roasting 8 hours, obtains ZrO 2-MnO 2support C-1.
By 16gNi (NO 3) 26H 2o and 3gNH 4nO 3be dissolved in 130mL distilled water and be made into steeping fluid, 100gC-1 is impregnated in steeping fluid, flood 24 hours, remove upper strata clear water, dry 3 hours in 110 DEG C, roasting 8 hours in 400 DEG C.Obtained catalyst A-1.The MnO of this catalyzer 2content is 3wt%, Ni content is 3wt%.
embodiment 2
By 185gZrCl 4and 16gMnCl 24H 2o is dissolved in 1000mL deionized water, is made into mixing solutions.Mixing salt solution being added drop-wise to 800mL concentration is in 0.2mol/L ammonia soln, and dropping 0.2mol/L NaOH solution control ph is 11 simultaneously.Dropwise rear stirring 40 minutes, more aging 24 hours of static precipitation in mother liquor at normal temperatures, obtained Zr (OH) 4with Mn (OH) 2mixing water gel.Zr (OH) 4with Mn (OH) 2mixing water gel with deionized water wash to without Cl -exist, filter and be precipitated thing, throw out is dried 6 hours at 110 DEG C, and at 300 DEG C, roasting 8 hours, obtains ZrO 2-MnO 2support C-2.
By 22gNi (NO 3) 26H 2o and 3gNH 4nO 3be dissolved in 130mL distilled water and be made into steeping fluid, 100gC-3 is impregnated in this steeping fluid, flood 24 hours, remove upper strata clear water, dry 3 hours in 110 DEG C, roasting 8 hours in 400 DEG C.Obtained catalyst A-2.The MnO of this catalyzer 2content is 6wt%, Ni content is 4wt%.
embodiment 3
By 250gZrOCl 28H 2o and 28gMn (NO 3) 24H 2o is dissolved in 1000mL deionized water, is made into mixing solutions.Mixing salt solution being added drop-wise to 800mL concentration is in 0.2mol/L ammonia soln, and dropping 0.2mol/L NaOH solution control ph is 11 simultaneously.Dropwise rear stirring 40 minutes, more aging 24 hours of static precipitation in mother liquor at normal temperatures, obtained Zr (OH) 4with Mn (OH) 2mixing water gel.Zr (OH) 4with Mn (OH) 2mixing water gel with deionized water wash to without Cl -exist, filter and be precipitated thing, throw out is dried 6 hours at 110 DEG C, and at 300 DEG C, roasting 8 hours, obtains ZrO 2-MnO 2support C-3.
By 24gNi (CH 3cOO) 24H 2o and 3.5g CH 3cOONH 4be dissolved in 150mL distilled water and be made into steeping fluid, 100gC-3 is impregnated in this steeping fluid, flood 24 hours, remove upper strata clear water, dry 3 hours in 110 DEG C, roasting 8 hours in 400 DEG C.Obtained catalyst A-3.The MnO of this catalyzer 2content is 8wt%, Ni content is 5wt%.
embodiment 4
ZrO 2-MnO 2the preparation of support C-4 is with embodiment 1.
By 27gNi (NO 3) 26H 2o and 3.2gNH 4nO 3be dissolved in 160mL distilled water and be made into steeping fluid, 100gC-4 is impregnated in this steeping fluid, flood 24 hours, remove upper strata clear water, dry 3 hours in 110 DEG C, roasting 8 hours in 400 DEG C.Obtained catalyst A-4.The MnO of this catalyzer 2content is 3wt%, Ni content is 5wt%.
embodiment 5
ZrO 2-MnO 2the preparation of support C-5 is with embodiment 3.
By 32gNi (NO 3) 26H 2o and 3.2gNH 4nO 3be dissolved in 160mL distilled water and be made into steeping fluid, 100gC-5 is impregnated in this steeping fluid, flood 24 hours, remove upper strata clear water, dry 3 hours in 110 DEG C, roasting 8 hours in 400 DEG C.Obtained catalyst A-5.The MnO of this catalyzer 2content is 8wt%, Ni content is 6wt%.
comparative example 1
By 17gNi (NO 3) 26H 2o is dissolved in 130mL distilled water and is made into the aqueous solution, with this solution impregnation 100g Zirconia carrier Z-1, removes upper strata clear water, dries 3 hours, roasting 8 hours in 400 DEG C in 110 DEG C.Obtained catalyst B-1.The Ni content of this catalyzer is 3wt%.
comparative example 2
By 17gNi (NO 3) 26H 2o is dissolved in 130mL distilled water and is made into the aqueous solution, with this solution impregnation 100g γ-Al 2o 3carrier Z-2, removes upper strata clear water, dries 3 hours, roasting 8 hours in 400 DEG C in 110 DEG C.Obtained catalyst B-2.The Ni content of this catalyzer is 3wt%.
comparative example 3
By 11gMn (NO 3) 24H 2o joins in 130mL distilled water and is made into the aqueous solution, with this solution impregnation 100g γ-Al 2o 3carrier, floods 24 hours.Remove upper strata clear water, dry 3 hours in 110 DEG C, then roasting 8 hours in 300 DEG C, make the carrier Z-3 containing manganese.
By 17gNi (NO 3) 26H 2o is dissolved in 130mL distilled water and is made into the aqueous solution, is impregnated into by 100gZ-3 in this nickel solution, removes upper strata clear water, dries 3 hours, roasting 8 hours in 400 DEG C in 110 DEG C.Obtained catalyst B-3.The Mn content of this catalyzer is 3wt%, Ni content is 3wt%.
comparative example 4
By 11gMn (NO 3) 24H 2o joins in 130mL distilled water and is made into the aqueous solution, with this solution impregnation 100gZrO 2carrier, floods 24 hours.Remove upper strata clear water, dry 3 hours in 110 DEG C, then roasting 8 hours in 300 DEG C, make the carrier Z-4 containing manganese.
By 17gNi (NO 3) 26H 2o is dissolved in 130mL distilled water and is made into the aqueous solution, is impregnated into by 100gZ-4 in this nickel solution, removes upper strata clear water, dries 3 hours, roasting 8 hours in 400 DEG C in 110 DEG C.Obtained catalyst B-4.The MnO of this catalyzer 2content is 3wt%, Ni content is 3wt%.
embodiment 6
Catalyzer C-1 is loaded reactor, adopts reduction method reduction in device.Reductive condition is: reduction temperature is 300 DEG C, and normal pressure reduces 8 hours, and during reduction, hydrogen gas space velocity is 120h -1.Answer temperature 180 DEG C, reaction pressure normal pressure, acetone feed air speed is 1.5, H 2/ acetone (V/V) is 300.
After raw material acetone enters reactor reaction, product through cooling and gas-liquid separation, vapor phase hydrogen emptying or recycle, liquid-phase reaction product gas chromatographic analysis.The transformation efficiency of result acetone is 49.78%, and the selectivity of diisobutyl ketone is 34.26%, and yield is 17.05%.
With the method for embodiment 6 respectively evaluate catalysts A-2, A-3, A-4, A-5, B-1, B-2, B-3, B-4 compare the performance of different catalysts, the results are shown in Table 1.
Table 1 catalyst performance evaluation.
As can be seen from the table, the yield of the activity of the catalyzer obtained by the present invention, selectivity and diisobutyl ketone compared with prior art has raising by a relatively large margin.

Claims (15)

1. a catalyzer for acetone synthesis diisobutyl ketone, is characterized in that: by active ingredient Ni and carrier ZrO 2-MnO 2composition, with overall catalyst weight gauge, active ingredient Ni in element content for 1wt% ~ 10wt%, MnO 2content be 1wt% ~ 20wt%, surplus is ZrO 2.
2., according to catalyzer according to claim 1, it is characterized in that: active ingredient Ni in element content for 3wt% ~ 6wt%, MnO 2content be 5wt% ~ 10wt%.
3. the preparation method of the catalyzer described in claim 1 or 2, it is characterized in that comprising following content: the mixing solutions of the soluble salt of the soluble salt containing zirconium and manganese is added drop-wise in alkaline solution by (1), control ph is 8 ~ 11, dropwise, stir 15 ~ 60 minutes, aging, obtain Zr (OH) 4with Mn (OH) 2mixing water gel, washing, drying, roasting, shaping, obtain ZrO 2-MnO 2carrier; (2) by ZrO that step (1) obtains 2-MnO 2carrier impregnation active ingredient Ni, dry, roasting obtains catalyst n i/ZrO 2-MnO 2; Wherein steeping fluid is the mixing solutions of the soluble salt containing ammonium salt and nickel.
4. in accordance with the method for claim 3, it is characterized in that: the soluble salt of the zirconium described in step (1) is one or both mixing in zirconium oxychloride and zirconium nitrate; The soluble salt of manganese is one or more in manganous nitrate, manganous sulfate and Manganous chloride tetrahydrate.
5. in accordance with the method for claim 3, it is characterized in that: described solution is the aqueous solution, C 4following alcoholic solution or be the mixing solutions of water and alcohol.
6. in accordance with the method for claim 3, it is characterized in that: in the mixing solutions of Zr and the Mn described in step (1), metal content is 0.02 ~ 1.5mol/L.
7. in accordance with the method for claim 3, it is characterized in that: described in step (1) aging for normal temperature aging, digestion time is 20 ~ 30 hours.
8. in accordance with the method for claim 3, it is characterized in that: the drying conditions described in step (1) is: drying 4 ~ 8 hours at 100 ~ 120 DEG C; Roasting condition is: roasting 6 ~ 10 hours at 200 ~ 500 DEG C.
9. in accordance with the method for claim 3, it is characterized in that: the soluble salt of the described nickel described in step (2) be in nitrate and acetate one or both; Ammonium salt be nitrate, vitriol, carbonate, acetate and muriate one or more.
10. according to the method described in claim 3 or 9, it is characterized in that: ammonium salt is identical with the negatively charged ion of the soluble salt of nickel.
11. in accordance with the method for claim 3, it is characterized in that: the dipping time described in step (2) is 20 ~ 25 hours.
12. in accordance with the method for claim 3, it is characterized in that: the drying conditions described in step (2) is: 100 ~ 115 DEG C of dryings 3 ~ 4 hours; Roasting condition is: 300 ~ 500 DEG C of roastings 8 ~ 10 hours.
13. in accordance with the method for claim 3, it is characterized in that: in step (2) steeping fluid, the content of Ni counts 0.05 ~ 1.5mol/L with element, NH in steeping fluid 4 +content be 0.01 ~ 1.0mol/L.
Catalyst application described in 14. claims 1 or 2 is in acetone synthesis diisobutyl reactive ketone.
15., according to reaction according to claim 14, is characterized in that: the condition of reaction is: temperature of reaction 150 ~ 250 DEG C, and reaction pressure is normal pressure, and acetone feed volume space velocity is 0.25 ~ 2.5h -1, H 2the volume ratio of/acetone is 200 ~ 500.
CN201310495783.0A 2013-10-22 2013-10-22 A kind of catalyst of acetone synthesis diisobutyl ketone and preparation method thereof Active CN104549348B (en)

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CN1218921C (en) * 2003-07-03 2005-09-14 中国科学院兰州化学物理研究所 Technological process for synthesizing methyl isobutyl ketone and diisobutyl ketone with acetone
CN1332752C (en) * 2004-08-09 2007-08-22 中国科学院大连化学物理研究所 Catalyst for synthesizing methyl isopropyl ketone and diethylketone, process for preparing the same and application thereof
FR2968002B1 (en) * 2010-11-30 2012-11-23 Rhodia Poliamida E Especialidades Ltda PROCESS FOR THE PRODUCTION OF DIBK
CN102698761A (en) * 2012-01-17 2012-10-03 中国海洋石油总公司 Preparation method of catalyst for hexone synthesis by acetone hydrogenation and application
CN102806085B (en) * 2012-08-13 2014-07-23 中国海洋石油总公司 Preparation method of catalyst for co-generating of isopropanol and diisobutyl ketone through acetone hydrogenation and application

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