CN107935830B - Process method for synthesizing 2,6, 8-trimethyl-4-nonanone by catalyzing methyl isobutyl ketone in one step - Google Patents
Process method for synthesizing 2,6, 8-trimethyl-4-nonanone by catalyzing methyl isobutyl ketone in one step Download PDFInfo
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- CN107935830B CN107935830B CN201711220546.8A CN201711220546A CN107935830B CN 107935830 B CN107935830 B CN 107935830B CN 201711220546 A CN201711220546 A CN 201711220546A CN 107935830 B CN107935830 B CN 107935830B
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- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
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Abstract
The invention belongs to the field of organic compound synthesis, and particularly relates to a process method for synthesizing 2,6, 8-trimethyl-4-nonanone by catalyzing methyl isobutyl ketone in one step, which comprises the following steps: using Ni-M/Al2O3Is used as a catalyst, the catalytic reaction is carried out for 3 to 8 hours under the reaction pressure of 1 to 5MPa and the reaction temperature of 100 to 150 ℃, and the catalyst is Ni-M/Al2O3In the formula, M represents one of Ce, La, Na, K and Cs, the content of M is 1-5 wt%, and the content of Ni is 5-25 wt%. By using Ni-M/Al2O3The conversion rate of methyl isobutyl ketone of the catalyst can reach 50 percent at most, and the selectivity of 2,6, 8-trimethyl-4-nonanone is also up to 90 percent.
Description
Technical Field
The invention belongs to the field of organic compound synthesis, and particularly relates to a process method for synthesizing 2,6, 8-trimethyl-4-nonanone in one step by catalyzing methyl isobutyl ketone.
Background
Branched chain ketone is an important chemical raw material and is widely applied to the field of organic synthesis. In particular, branched ketones are particularly appreciated for use in the daily chemical industry due to their particular physicochemical properties. Compared with straight chain ketone, the branched chain ketone has the advantages of small smell, no irritation to human body, low solidifying point, and excellent flowability, wettability and permeability under the condition of the same carbon number. 2,6, 8-trimethyl-4-nonanone is a main raw material for producing the surfactant as a branched chain ketone, and is widely regarded by industry.
Generally ketones are prepared mainly by oxidation of secondary alcohols, hydrogenation of unsaturated ketones, decarboxylation of carboxylic acids and hydration of non-terminal alkynes. Common to most reactions is that the starting materials used for them are relatively expensive compounds and are often prepared under severe reaction conditions and/or via the necessary complicated product isolation steps. Thus, a great improvement in the preparation of ketones is the use of relatively inexpensive or readily available starting materials or starting materials.
At present, there are rare reports on the preparation of complex ketones via a one-step process of ketone self-condensation. The reason for this is that long-chain aliphatic ketones (such as methyl isobutyl ketone) have a relatively large steric hindrance and a low reactivity, and the selectivity of the condensation reaction and the hydrogenation reaction is difficult to control.
Disclosure of Invention
The invention provides a process method for synthesizing 2,6, 8-trimethyl-4-nonanone in one step by catalyzing methyl isobutyl ketone, which has the characteristics of simple catalyst preparation, convenient reaction raw material source, mild reaction condition, high product yield, less by-products, environmental protection and the like, and the reaction mechanism is as follows:
namely using Ni-M/Al2O3As a catalyst, the reaction is catalyzed for 3 to 8 hours under the reaction pressure of 1 to 5MPa and the reaction temperature of 100 to 150 ℃,
catalyst Ni-M/Al2O3Wherein M represents one of Ce, La, Na, K and Cs, the content of M is 1-5 wt%, the content of Ni is 5-25 wt%,
catalyst Ni-M/Al2O3The preparation method adopts an immersion method, and comprises the following specific process steps:
(1) mixing gamma-Al2O3Roasting at 500 deg.c for 4 hr;
(2) preparing soluble salt of nickel into an impregnation solution, and impregnating the impregnation solution in the gamma-Al treated in the step (1) in an equal volume manner2O3Drying at constant temperature of 110 ℃ to constant weight, then soaking in a soluble salt solution of M, drying, roasting and reducing to obtain Ni-M/Al2O3A catalyst,
the soluble salt of nickel or M is one of nitrate, carbonate and chloride.
The beneficial effect of this patent lies in: by using Ni-M/Al2O3The conversion rate of the catalyst, methyl isobutyl ketone, can reach 50 percent at most, and simultaneously 2,6, 8-trimethylThe selectivity of the-4-nonanone is also up to 90 percent, and the reaction product mainly contains 2,6, 8-trimethyl-4-nonanone; the catalyst is added with alkali metal or rare earth metal as an auxiliary agent, so that the effective condensation of the methyl isobutyl ketone can be effectively promoted, and the acid-base preparation of the carrier can be changed.
Drawings
FIG. 1 is a gas mass spectrum of the product 2,6, 8-trimethyl-4-nonanone synthesized in example 5.
Detailed Description
Example 1
(1) Mixing gamma-Al2O3Roasting at 500 deg.c for 4 hr;
(2) 2.4897g of Ni (NO)3)2·6H2Dissolving O in 30g of distilled water to obtain a solution, and adding 10g of the gamma-Al treated in the step (1)2O3Adding into the soaking solution, dispersing thoroughly, soaking for 12 hr, and drying at constant temperature of 110 deg.C to constant weight; 0.3099g of Ce (NO)3)3·6H2Dissolving O in 30g of distilled water, and adding the treated gamma-Al2O3Soaking for 12h, drying at constant temperature of 110 ℃ to constant weight, and roasting at 500 ℃ for 4h to obtain a catalyst precursor; activating the prepared catalyst precursor in hydrogen atmosphere at normal pressure at 400 ℃ for 2h to prepare Ni-Ce/Al2O3A catalyst.
The catalytic reaction is carried out in a batch reactor, 100g of methyl isobutyl ketone is taken as a raw material, 5g of the catalyst prepared in the example 1 is added, the reaction is carried out for 8 hours under the conditions of 1MPa of hydrogen pressure, 100 ℃ of reaction temperature and 800r/min of stirring speed, the composition of the product is detected by adopting gas chromatography, the conversion rate of the methyl isobutyl ketone as the raw material is 36.15%, the selectivity is 88.27%, and the yield of the product 2,6, 8-trimethyl-4-nonanone is 31.91%.
Example 2
(1) Mixing gamma-Al2O3Roasting at 500 deg.c for 4 hr;
(2) 5.5052g of Ni (NO)3)2·6H2Dissolving O in 30g of distilled water to obtain a solution, and adding 10g of the gamma-Al treated in the step (1)2O3Adding into the soaking solution and dispersing thoroughlyAfter 12h of dipping, drying at the constant temperature of 110 ℃ to constant weight; 0.6234g of La (NO)3)3·6H2Dissolving O in 30g of distilled water, and adding the treated gamma-Al2O3Soaking for 12h, drying at constant temperature of 110 ℃ to constant weight, and roasting at 500 ℃ for 4h to obtain a catalyst precursor; activating the prepared catalyst precursor in hydrogen atmosphere at normal pressure at 400 ℃ for 2h to prepare Ni-La/Al2O3A catalyst.
The catalytic reaction is carried out in a batch reactor, 100g of methyl isobutyl ketone is taken as a raw material, 10g of the catalyst prepared in the example 2 is added, the reaction is carried out for 7 hours under the conditions of hydrogen pressure of 2MPa, reaction temperature of 110 ℃ and stirring speed of 800r/min, the gas chromatography is adopted to detect the composition of the product, the conversion rate of the raw material methyl isobutyl ketone is 39.52 percent, the selectivity is 92.39 percent, and the yield of the product 2,6, 8-trimethyl-4-nonanone is 36.51 percent.
Example 3
(1) Mixing gamma-Al2O3Roasting at 500 deg.c for 4 hr;
(2) 8.7202g of Ni (NO)3)2·6H2Dissolving O in 30g of distilled water to obtain a solution, and adding 10g of the gamma-Al treated in the step (1)2O3Adding into the soaking solution, dispersing thoroughly, soaking for 12 hr, and drying at constant temperature of 110 deg.C to constant weight; 1.1087g of NaNO3Dissolving in 30g of distilled water, and adding the treated gamma-Al2O3Soaking for 12h, drying at constant temperature of 110 ℃ to constant weight, and roasting at 500 ℃ for 4h to obtain a catalyst precursor; activating the prepared catalyst precursor in hydrogen atmosphere at normal pressure at 400 ℃ for 2h to prepare Ni-Na/Al2O3A catalyst.
The catalytic reaction is carried out in a batch reactor, 100g of methyl isobutyl ketone is taken as a raw material, 15g of the catalyst prepared in the example 3 is added, the reaction is carried out for 6 hours under the conditions of 3MPa of hydrogen pressure, 140 ℃ of reaction temperature and 800r/min of stirring speed, the gas chromatography is adopted to detect the composition of the product, the conversion rate of the raw material methyl isobutyl ketone is 40.17%, the selectivity is 91.21%, and the yield of the product 2,6, 8-trimethyl-4-nonanone is 36.64%.
Example 4
(1) Mixing gamma-Al2O3Roasting at 500 deg.c for 4 hr;
(2) 16.5139g of Ni (NO)3)2·6H2Dissolving O in 30g of distilled water to obtain a solution, and adding 10g of the gamma-Al treated in the step (1)2O3Adding into the soaking solution, dispersing thoroughly, soaking for 12 hr, and drying at constant temperature of 110 deg.C to constant weight; 1.0342g of KNO3Dissolving in 30g of distilled water, and adding the treated gamma-Al2O3Soaking for 12h, drying at constant temperature of 110 ℃ to constant weight, and roasting at 500 ℃ for 4h to obtain a catalyst precursor; activating the prepared catalyst precursor in hydrogen atmosphere at normal pressure at 400 ℃ for 2h to prepare Ni-K/Al2O3A catalyst.
The catalytic reaction is carried out in a batch reactor, 100g of methyl isobutyl ketone is taken as a raw material, 25g of the catalyst prepared in the example 4 is added, the reaction is carried out for 3 hours under the conditions of hydrogen pressure of 5MPa, reaction temperature of 150 ℃ and stirring speed of 800r/min, the gas chromatography is adopted to detect the composition of the product, the conversion rate of the raw material methyl isobutyl ketone is 49.45%, the selectivity is 87.12%, and the yield of the product 2,6, 8-trimethyl-4-nonanone is 43.08%.
Example 5
(1) Mixing gamma-Al2O3Roasting at 500 deg.c for 4 hr;
(2) 8.7202g of Ni (NO)3)2·6H2Dissolving O in 30g of distilled water to obtain a solution, and adding 10g of the gamma-Al treated in the step (1)2O3Adding into the soaking solution, dispersing thoroughly, soaking for 12 hr, and drying at constant temperature of 110 deg.C to constant weight; 0.6334g of CsCl was dissolved in 30g of distilled water, and the treated γ -Al was added2O3Soaking for 12h, drying at constant temperature of 110 ℃ to constant weight, and roasting at 500 ℃ for 4h to obtain a catalyst precursor; activating the prepared catalyst precursor in hydrogen atmosphere at normal pressure at 400 ℃ for 2h to prepare Ni-Cs/Al2O3Catalyst, Ni content 15 wt%, Cs content 5 wt%.
The catalytic reaction is carried out in a batch reactor, 100g of methyl isobutyl ketone is taken as a raw material, 20g of the catalyst prepared in the example 5 is added, the reaction is carried out for 7 hours under the conditions of hydrogen pressure of 3MPa, reaction temperature of 150 ℃ and stirring speed of 800r/min, the gas chromatography is adopted to detect the composition of the product, the conversion rate of the raw material methyl isobutyl ketone is 50.05%, the selectivity is 90.12%, and the yield of the product 2,6, 8-trimethyl-4-nonanone is 45.11%.
Comparative example 1
In example 5, Pd-Cs/Al having a Pd content of 15 wt% and a Cs content of 5 wt% was prepared by replacing the nickel salt with the palladium salt2O3A catalyst;
by using 100g of methyl isobutyl ketone as a raw material and adding 20g of the catalyst prepared in comparative example 1, and adjusting the hydrogen pressure, the reaction temperature, the stirring speed and the reaction time to the optimal state of the yield of the target product, the composition of the product is detected by gas chromatography, the conversion rate of the raw material methyl isobutyl ketone is 39.28%, the selectivity is 72.13%, and the yield of the product 2,6, 8-trimethyl-4-nonanone is 28.33%.
Comparative example 2
In example 5, by replacing the nickel salt with the platinum salt, Pt-Cs/Al having a Pt content of 15 wt% and a Cs content of 5 wt% was prepared2O3A catalyst;
100g of methyl isobutyl ketone was used as a raw material, 20g of the catalyst prepared in comparative example 2 was added, the hydrogen pressure, the reaction temperature, the stirring speed and the reaction time were adjusted to the most ideal state for the yield of the target product, and the product composition was determined by gas chromatography, whereby the conversion of the raw material methyl isobutyl ketone was 58.07%, the selectivity was 31.58% and the yield of the product 2,6, 8-trimethyl-4-nonanone was 18.33%.
Comparative example 3
In example 5, by replacing the Cs salt with the Mn salt, Ni-Mn/Al was prepared with a Ni content of 15 wt% and a Mn content of 5 wt%2O3A catalyst;
100g of methyl isobutyl ketone was used as a raw material, 20g of the catalyst prepared in comparative example 3 was added, the hydrogen pressure, the reaction temperature, the stirring speed and the reaction time were adjusted to the optimal state for the yield of the target product, and the product composition was determined by gas chromatography, whereby the conversion of the raw material methyl isobutyl ketone was 25.50%, the selectivity was 40.23% and the yield of the product 2,6, 8-trimethyl-4-nonanone was 10.26%.
Comparative example 4
Using equimolar acetone (58.08g, 1mol) as a raw material, 20g of the catalyst prepared in example 5 was added, and by adjusting the hydrogen pressure, reaction temperature, stirring speed and reaction time to the optimum state for the yield of the target product, the product composition was examined by gas chromatography, the conversion of the raw material acetone was 62.58%, the selectivity was 46.73% and the yield of the product, 4-methyl-2-pentanone, was 29.24%.
Comparative example 5
Starting with an equimolar amount of acetone (58.08g, 1mol), 20g of the Pd-Cs/Al catalyst prepared in comparative example 1 were added2O3The hydrogen pressure, the reaction temperature, the stirring speed and the reaction time are adjusted to the optimal state of the yield of the target product, the composition of the product is detected by adopting gas chromatography, the conversion rate of the raw material acetone is 30.26 percent, the selectivity is 92.15 percent, and the yield of the product 4-methyl-2-pentanone is 27.88 percent.
Claims (6)
1. A process method for synthesizing 2,6, 8-trimethyl-4-nonanone by catalyzing methyl isobutyl ketone in one step is characterized by comprising the following steps: the method is to use Ni-M/Al2O3Catalyzing methyl isobutyl ketone to react with hydrogen by using a catalyst;
the Ni-M/Al2O3The preparation method adopts an immersion method, and comprises the following specific process steps,
(1) mixing gamma-Al2O3Roasting;
(2) preparing soluble salt of nickel into impregnation liquid, and impregnating the impregnation liquid in the gamma-Al roasted in the step (1)2O3Drying to constant weight, soaking in soluble salt solution of M, drying, roasting and reducing to obtain Ni-M/Al2O3；
The M represents one of Ce, La, Na, K and Cs, the content of the M is 1-5 wt%, and the content of the Ni is 5-25 wt%.
2. The process method for one-step synthesis of 2,6, 8-trimethyl-4-nonanone by catalyzing methyl isobutyl ketone as claimed in claim 1, wherein: the reaction pressure of the methyl isobutyl ketone and hydrogen is 1-5 MPa when the methyl isobutyl ketone and the hydrogen are catalyzed, and the reaction temperature is 100-150 ℃.
3. The process method for one-step synthesis of 2,6, 8-trimethyl-4-nonanone by catalyzing methyl isobutyl ketone as claimed in claim 1, wherein: in the step (1), the mixture is roasted for 4 hours at 500 ℃.
4. The process of claim 1 for the synthesis of 2,6, 8-trimethyl-4-nonanone, wherein: in the step (2), the soluble salt of nickel is one of nitrate, carbonate and chloride.
5. The process of claim 1 for the synthesis of 2,6, 8-trimethyl-4-nonanone, wherein: in the step (2), the soluble salt of M is one of nitrate, carbonate and chloride.
6. The process of claim 1 for the synthesis of 2,6, 8-trimethyl-4-nonanone, wherein: in the step (2), the drying temperature is 110 ℃.
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| Direct Synthesis of Renewable Dodecanol and Dodecane with Methyl Isobutyl Ketone over Dual-Bed Catalyst Systems;Xueru Sheng等;《ChemSusChem》;20161229;第10卷(第5期);第825页右栏最后一段至826页左栏第1-2段，图1 * |
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