CN114669294A - Composite catalyst for preparing 2, 2-di (2-tetrahydrofuryl) propane by hydrogenating 2, 2-di (2-furyl) propane - Google Patents
Composite catalyst for preparing 2, 2-di (2-tetrahydrofuryl) propane by hydrogenating 2, 2-di (2-furyl) propane Download PDFInfo
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Abstract
The invention relates to a composite catalyst for preparing 2, 2-di (2-tetrahydrofuryl) propane by hydrogenating 2, 2-di (2-furyl) propane, which mainly comprises active components, an auxiliary agent and a carrier, wherein the active components are Pd and Ru, and the auxiliary agent is element Li. The catalyst is loaded on a carrier by an impregnation method, has certain activity by chemical reduction, can be applied to the reaction for preparing DTHFP from DFP, and can keep the conversion rate of DFP and the selectivity of DTHFP to be more than 99.0 percent and the meso isomer to be more than 79 percent; the activity can not be reduced after repeated application for 20 times in the process of preparing the 2, 2-bis (2-tetrahydrofuryl) propane by hydrogenating the 2, 2-bis (2-furyl) propane.
Description
Technical Field
The invention belongs to the technical field of catalyst preparation, and particularly relates to a composite catalyst for preparing 2, 2-di (2-tetrahydrofuryl) propane by hydrogenating 2, 2-di (2-furyl) propane and a preparation method thereof.
Background
2, 2-di (2-tetrahydrofuryl) propane (hereinafter referred to as DTHFP) is prepared by hydrogenating 2, 2-di (2-furyl) propane (hereinafter referred to as DFP), and DTHFP has three isomers, wherein a meso isomer has wide application and high value.
The prior patent US4577035A uses a palladium catalyst without any addition of auxiliaries and the meso isomer selectivity is about 50%. Patent WO2016046575a1 is improved on the basis that it is carried out in the presence of an auxiliary agent, i.e. lithium salt (such as carboxylate, carbonate, hydroxide, chloride or borate) and an organic solvent (such as tetrahydrofuran, water, ethanol, isopropanol or heptane), and can improve the selectivity of meso-isomer to over 80%.
Disclosure of Invention
The invention aims to overcome and solve the technical defects of the existing patents of US4577035A and WO2016046575A1 and provides a composite catalyst for preparing 2, 2-bis (2-tetrahydrofuryl) propane by hydrogenating 2, 2-bis (2-furyl) propane, which can be subjected to hydrogenation reaction without using a solvent and has the advantages of high selectivity of meso isomer, environmental protection, no reduction of activity after the catalyst can be repeatedly used for more than 20 times and the like.
The invention also provides a preparation method of the composite catalyst for preparing 2, 2-di (2-tetrahydrofuryl) propane by hydrogenating the 2, 2-di (2-furyl) propane.
In order to achieve the purpose, the invention adopts the following technical scheme:
the composite catalyst for preparing 2, 2-di (2-tetrahydrofuryl) propane by hydrogenating 2, 2-di (2-furyl) propane mainly comprises active components, an auxiliary agent and a carrier, wherein the active components are Pd and Ru, and the auxiliary agent is element Li.
Specifically, the total loading of the active components (Pd, Ru) is 2 to 7%, further 4 to 7%, preferably 5%. The loading ratio of metal elements Pd, Ru and Li is 1.0: (0-1.5): (1.0-2.5), and preferably selecting 2% Pd/3% Ru/2% Li after converting the actual load.
Specifically, the carrier is one or more of activated carbon, carbon nanotubes, barium sulfate and alumina, and preferably activated carbon.
The preparation method of the composite catalyst for preparing 2, 2-bis (2-tetrahydrofuryl) propane by hydrogenating 2, 2-bis (2-furyl) propane comprises the following steps: stirring and uniformly mixing the soluble salt water solution of Pd, Ru and Li, the carrier and water according to a certain proportion, soaking for 8-15h (preferably 10-12h) at room temperature, adjusting the pH value to 9-10, then adding excessive reducing agent, heating to above 40 ℃, carrying out reduction reaction for not less than 20min, cooling to room temperature, filtering, washing and drying to obtain the catalyst. The method adopts the steps of dipping, reduction, washing and the like to prepare the high-activity hydrogenation catalyst, and the catalyst has higher catalytic activity in the process of preparing 2, 2-di (2-tetrahydrofuryl) propane by hydrogenating 2, 2-di (2-furyl) propane and can be used repeatedly.
Further, the catalyst is prepared by a liquid phase reduction method, and the reducing agent is one or more of formaldehyde, hydrazine hydrate, sodium borohydride and hydrogen, preferably hydrazine hydrate. The soluble salt aqueous solution of Pd, Ru or Li may be chloride aqueous solution or nitrate aqueous solution thereof. The reducing agent is generally 5 to 10 times of the sum of the mole amounts of Pd and Ru.
Preferably, the temperature is increased to 40-70 ℃ for reduction reaction for 20-60 min.
Specifically, sodium hydroxide aqueous solution with the mass percentage concentration of 10-20% is selected to adjust the pH value to 9-10.
Specifically, the washing is carried out with deionized water until the conductivity is 100. mu.S/cm or less.
The invention also provides application of the composite catalyst in preparation of 2, 2-di (2-tetrahydrofuryl) propane by hydrogenation of 2, 2-di (2-furyl) propane.
The invention provides a Pd/Ru/Li composite catalyst capable of carrying out hydrogenation reaction without using a solvent, which is used for preparing 2, 2-di (2-tetrahydrofuryl) propane by hydrogenating 2, 2-di (2-furyl) propane, has meso isomer selectivity equivalent to that of a patent WO2016046575A1, does not need a solvent, has relatively low metal loading of the catalyst, can effectively reduce the cost, is green and environment-friendly, and does not reduce the activity after being repeatedly used for more than 20 times. Compared with the prior art, the invention has the following beneficial effects:
1) the invention solves the defects that the WO2016046575A1 needs to use solvent and supplement auxiliary agent every time, thus the whole process is more environment-friendly;
2) the invention fully utilizes the catalytic advantages of the Pd/Ru/Li composite catalyst, has good catalytic effect, and can maintain better activity and selectivity after being repeatedly applied for more than 20 times;
3) when the catalyst is prepared, the cheap metal Ru is used for replacing part of metal Pd, so that the use amount of noble metal Pd is directly reduced, and the use amount of an auxiliary agent (Li salt) is also reduced because the Li salt can be better dispersed into the catalyst;
4) when the catalyst prepared by the invention is applied to the reaction of preparing DTHFP from DFP, the conversion rate of DFP and the selectivity of DTHFP can be kept above 99.0%, and the meso isomer accounts for above 79%.
Detailed Description
The technical solution of the present invention is further described in detail with reference to the following examples, but the scope of the present invention is not limited thereto.
In the examples, the starting materials used were all common commercial products which were directly available in the art. Room temperature refers to 25 ± 5 ℃.
Example 1:
accurately weighing a certain amount of palladium chloride aqueous solution, adding 19g of dry-based activated carbon into a 200ml beaker, adding 100ml of deionized water, slowly dripping the metal solution after magnetically stirring for 10min, stirring and soaking for 10h at room temperature, adjusting the pH to 9-10 by using 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%, by mass percentage, the same below) and slowly dripping, heating to 50 ℃ for 30min, preserving the temperature for 30min for reduction reaction, cooling to room temperature after the reaction is finished, filtering, pulping and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst 5% Pd/C is obtained.
Example 2:
accurately weighing a certain amount of palladium chloride aqueous solution, adding 19g of gamma-Al 2O3 as a dry basis into a 200ml beaker, adding 100ml of deionized water, slowly dripping the metal solution after magnetically stirring for 10min, stirring and soaking at room temperature for 10h, adjusting the pH to 9-10 by using 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%), slowly dripping, heating to 50 ℃ for 30min, preserving the temperature for 30min for reduction reaction, cooling to room temperature after the reaction is finished, filtering, pulping and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst 5% Pd/Al2O3 is obtained.
Example 3:
accurately weighing a certain amount of palladium chloride aqueous solution, adding 19g of dry-based carbon nano tubes into a 200ml beaker, adding 100ml of deionized water, slowly dripping the metal solution after magnetically stirring for 10min, stirring and soaking for 10h at room temperature, adjusting the pH to 9-10 by using 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%), slowly dripping, heating to 50 ℃ for 30min, keeping the temperature for 30min for reduction reaction, cooling to room temperature after the reaction is finished, filtering, beating and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst 5% Pd/CNTs is obtained.
Evaluation of catalyst Performance:
100g DFP and 1g dry catalyst are added into a 200ml stainless steel reaction kettle, air is replaced by nitrogen for four times, then nitrogen is replaced by hydrogen for three times, the stirring speed is adjusted to 800r/min, the reaction is carried out at the reaction temperature of 160 ℃ and the pressure of 8MPa until no hydrogen is absorbed, namely the pressure reduction speed is less than 0.1MPa/h, the reaction is continued for 2h, the temperature is reduced to the room temperature after the reaction is finished, the filtration is carried out, and the hydrogenated liquid is detected and analyzed by gas chromatography, and the result is shown in Table 1.
Table 1, results of evaluating the performance of catalysts of examples 1 to 3
According to the results of the evaluation of catalytic performance in Table 1, the catalyst prepared in example 1, i.e., activated carbon was selected as the carrier.
Example 4:
accurately weighing an aqueous solution containing a certain amount of palladium chloride and ruthenium trichloride, adding 19g of dry-based activated carbon into a 200ml beaker, adding 100ml of deionized water, slowly dripping a metal solution after magnetically stirring for 10min, stirring and soaking for 10h at room temperature, adjusting the pH to 9-10 by using a 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%), slowly dripping, heating to 50 ℃ for 30min, preserving the temperature for 30min to perform a reduction reaction, cooling to room temperature after the reaction is finished, filtering, pulping and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst 4% Pd/1% Ru/C was obtained.
Example 5:
accurately weighing an aqueous solution containing a certain amount of palladium chloride and ruthenium trichloride, adding 19g of dry-based activated carbon into a 200ml beaker, adding 100ml of deionized water, slowly dripping a metal solution after magnetically stirring for 10min, stirring and soaking for 10h at room temperature, adjusting the pH to 9-10 by using a 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%), slowly dripping, heating to 50 ℃ for 30min, preserving the temperature for 30min to perform a reduction reaction, cooling to room temperature after the reaction is finished, filtering, pulping and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst 3% Pd/2% Ru/C was obtained.
Example 6:
accurately weighing an aqueous solution containing a certain amount of palladium chloride and ruthenium trichloride, adding 19g of dry-based activated carbon into a 200ml beaker, adding 100ml of deionized water, slowly dripping a metal solution after magnetically stirring for 10min, stirring and soaking for 10h, adjusting the pH to 9-10 by using a 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%), slowly dripping, heating to 50 ℃ for 30min, preserving the temperature for 30min to perform a reduction reaction, reducing the temperature to room temperature after the reaction is finished, filtering, pulping and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst 2.5% Pd/2.5% Ru/C was obtained.
Example 7:
accurately weighing an aqueous solution containing a certain amount of palladium chloride and ruthenium trichloride, adding 19g of dry-based activated carbon into a 200ml beaker, adding 100ml of deionized water, slowly dripping a metal solution after magnetically stirring for 10min, stirring and soaking for 10h, adjusting the pH to 9-10 by using a 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%), slowly dripping, heating to 50 ℃ for 30min, preserving the temperature for 30min to perform a reduction reaction, reducing the temperature to room temperature after the reaction is finished, filtering, pulping and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst 2% Pd/3% Ru/C was obtained.
Example 8:
accurately weighing an aqueous solution containing a certain amount of palladium chloride and ruthenium trichloride, adding 19g of dry-based activated carbon into a 200ml beaker, adding 100ml of deionized water, slowly dripping a metal solution after magnetically stirring for 10min, stirring and soaking for 10h, adjusting the pH to 9-10 by using a 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%), slowly dripping, heating to 50 ℃ for 30min, preserving the temperature for 30min to perform a reduction reaction, reducing the temperature to room temperature after the reaction is finished, filtering, pulping and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst 1% Pd/4% Ru/C was obtained.
The catalytic performances of the catalysts prepared in examples 4 to 8 were measured with reference to the above-mentioned catalyst performance evaluation methods, and the results are shown in Table 2 below.
Table 2, results of evaluating the performance of catalysts of examples 1, 4 to 8
The results of table 2 above illustrate that:
1) the Ru is used for replacing Pd with the same mass, so that the influence on the DFP conversion rate and the DTHFP selectivity is small, and the content of the inner racemic isomer is slightly positively influenced;
2) with the increase of the ruthenium content, the activity of the catalyst is slightly reduced, and the reaction time is correspondingly increased;
3) the catalyst of example 7 is more advantageous in cost, and the catalyst of example 7 is preferably suggested.
Example 9:
accurately weighing an aqueous solution containing a certain amount of palladium chloride, ruthenium trichloride and lithium chloride, adding 19g of dry-based activated carbon into a 200ml beaker, adding 100ml of deionized water, slowly dripping a metal solution after magnetically stirring for 10min, stirring and soaking for 10h, adjusting the pH to 9-10 by using a 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%), slowly dripping, heating to 50 ℃ for 30min, preserving the temperature for 30min to perform a reduction reaction, cooling to room temperature after the reaction is finished, filtering, pulping and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst was obtained 2% Pd/3% Ru/0.5% Li/C.
Example 10:
accurately weighing an aqueous solution containing a certain amount of palladium chloride, ruthenium trichloride and lithium chloride, adding 19g of dry-based activated carbon into a 200ml beaker, adding 100ml of deionized water, slowly dripping a metal solution after magnetically stirring for 10min, stirring and soaking for 10h, adjusting the pH to 9-10 by using a 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%), slowly dripping, heating to 50 ℃ for 30min, preserving the temperature for 30min to perform a reduction reaction, cooling to room temperature after the reaction is finished, filtering, pulping and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst 2% Pd/3% Ru/1.0% Li/C was obtained.
Example 11:
accurately weighing an aqueous solution containing a certain amount of palladium chloride, ruthenium trichloride and lithium chloride, adding 19g of dry-based activated carbon into a 200ml beaker, adding 100ml of deionized water, slowly dripping a metal solution after magnetically stirring for 10min, stirring and soaking for 10h, adjusting the pH to 9-10 by using a 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%), slowly dripping, heating to 50 ℃ for 30min, preserving the temperature for 30min to perform a reduction reaction, cooling to room temperature after the reaction is finished, filtering, pulping and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst was obtained 2% Pd/3% Ru/1.5% Li/C.
Example 12:
accurately weighing an aqueous solution containing a certain amount of palladium chloride, ruthenium trichloride and lithium chloride, adding 19g of dry-based activated carbon into a 200ml beaker, adding 100ml of deionized water, slowly dripping a metal solution after magnetically stirring for 10min, stirring and soaking for 10h, adjusting the pH to 9-10 by using a 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%), slowly dripping, heating to 50 ℃ for 30min, preserving the temperature for 30min to perform a reduction reaction, cooling to room temperature after the reaction is finished, filtering, pulping and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst was obtained 2% Pd/3% Ru/2.0% Li/C.
Example 13:
accurately weighing an aqueous solution containing a certain amount of palladium chloride, ruthenium trichloride and lithium chloride, adding 19g of dry-based activated carbon into a 200ml beaker, adding 100ml of deionized water, slowly dripping a metal solution after magnetically stirring for 10min, stirring and soaking for 10h, adjusting the pH to 9-10 by using a 15% sodium hydroxide aqueous solution, then weighing 3.5g of hydrazine hydrate (80%), slowly dripping, heating to 50 ℃ for 30min, preserving the temperature for 30min to perform a reduction reaction, cooling to room temperature after the reaction is finished, filtering, pulping and washing by using deionized water until the conductivity is below 100 mu S/cm, and drying at 110 ℃. The catalyst was obtained 2% Pd/3% Ru/2.5% Li/C.
The catalytic performances of the catalysts prepared in examples 9 to 13 were measured with reference to the above-mentioned catalyst performance evaluation methods, and the results are shown in Table 3 below.
Table 3, results of evaluating the performances of the catalysts of examples 9 to 13
The results of table 3 above illustrate that:
1) after metallic Li is introduced, the selectivity of meso isomer is obviously improved, the meso isomer content is increased along with the increase of Li content, but the reaction time is relatively prolonged;
2) preferred example 12 the resulting catalyst was prepared.
The catalyst prepared in example 12 was used indiscriminately, and the catalyst was added directly to the reactor without treatment. In addition, because of the catalyst loss during the transfer and filtration processes, 10% of the initial amount is added each time when the catalyst is used, and the evaluation data are summarized as shown in the following table 4.
TABLE 4, example 12 evaluation of catalyst application Performance
The results in table 4 show: the catalyst prepared in example 12 can be repeatedly used for 20 times without obvious reduction of activity, the reaction is influenced to a certain extent by factors such as catalyst amount, stirring speed, reaction time, heating speed and the like, and the data obtained in the experiment are slightly fluctuated, which belongs to a normal phenomenon.
The above description is for the purpose of describing the present invention in detail with reference to specific embodiments, and the present invention should not be construed as being limited to the above description. All such alterations and modifications as would be obvious to one skilled in the art are intended to be included within the scope of the present invention as defined by the appended claims.
Claims (9)
1. The composite catalyst for preparing 2, 2-bis (2-tetrahydrofuryl) propane by hydrogenating 2, 2-bis (2-furyl) propane is characterized by mainly comprising an active component, an auxiliary agent and a carrier, wherein the active component is Pd and Ru, the auxiliary agent is element Li, and the loading capacity of the active component is 2-7%.
2. The composite catalyst for hydrogenation of 2, 2-bis (2-furyl) propane to 2, 2-bis (2-tetrahydrofuryl) propane according to claim 1, wherein the loading ratio of the metal elements Pd, Ru and Li is 1.0: (0-1.5): (1.0-2.5).
3. The composite catalyst for hydrogenation of 2, 2-bis (2-furyl) propane to 2, 2-bis (2-tetrahydrofuryl) propane according to claim 1, wherein the support is one or more of activated carbon, carbon nanotubes, barium sulfate, and alumina.
4. A preparation method of the composite catalyst for preparing 2, 2-bis (2-tetrahydrofuryl) propane by hydrogenating 2, 2-bis (2-furyl) propane according to any one of claims 1 to 3, which is characterized in that soluble salt aqueous solution of Pd, Ru and Li, a carrier and water are uniformly stirred according to a proportion, dipped for 8 to 15 hours at room temperature, the pH value is adjusted to 9 to 10, then excessive reducing agent is added, the temperature is raised to more than 40 ℃ for reduction reaction for not less than 20 minutes, and the composite catalyst is obtained by cooling to room temperature, filtering, washing and drying.
5. The method for preparing the composite catalyst for preparing 2, 2-bis (2-tetrahydrofuryl) propane by hydrogenating 2, 2-bis (2-furanyl) propane according to claim 4, wherein the reducing agent is one or more of formaldehyde, hydrazine hydrate, sodium borohydride and hydrogen.
6. The method for preparing the composite catalyst for preparing 2, 2-bis (2-tetrahydrofuryl) propane by hydrogenating 2, 2-bis (2-furanyl) propane according to claim 4, wherein the temperature is raised to 40 to 70 ℃ for the reduction reaction for 20 to 60 min.
7. The method for preparing the composite catalyst for preparing 2, 2-bis (2-tetrahydrofuryl) propane by hydrogenating 2, 2-bis (2-furanyl) propane according to claim 4, wherein the pH is adjusted to 9 to 10 by using an aqueous solution of sodium hydroxide with a mass concentration of 10 to 20%.
8. The method for producing a composite catalyst for producing 2, 2-bis (2-tetrahydrofuryl) propane by hydrogenating 2, 2-bis (2-furanyl) propane according to claim 4, wherein the washing is carried out with deionized water until the conductivity is 100. mu.S/cm or less.
9. Use of the composite catalyst of any one of claims 1 to 3 in the hydrogenation of 2, 2-bis (2-furyl) propane to produce 2, 2-bis (2-tetrahydrofuryl) propane.
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| WO2022149471A1 (en) * | 2021-01-07 | 2022-07-14 | 旭化成株式会社 | Rubber composition for crosslinking, rubber composition for tire, molded body for tire sidewall, sheet, method for producing tire sidewall, and tire sidewall |
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| CN114602463A (en) * | 2022-04-13 | 2022-06-10 | 宏业生物科技股份有限公司 | Ethyl p-hydroxybenzoate hydrogenation catalyst and preparation method thereof |
| CN114602463B (en) * | 2022-04-13 | 2023-12-05 | 宏业生物科技股份有限公司 | P-hydroxybenzoic acid ethyl ester hydrogenation catalyst and preparation method thereof |
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