CN107866252B - Catalyst for synthesizing pyromellitic anhydride from durene - Google Patents
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Abstract
2 3The invention relates to a catalyst for synthesizing pyromellitic anhydride from durene, which mainly solves the problem of low yield of the pyromellitic anhydride caused by a plurality of byproducts generated in the reaction of synthesizing the pyromellitic anhydride from durene in the prior art.
Description
Technical Field
The invention relates to a catalyst for synthesizing pyromellitic anhydride from durene, a preparation method thereof and a synthesis method of the pyromellitic anhydride.
Technical Field
With the rapid development of petroleum refining, chemical fiber, polyester and other industries, large-scale ethylene plants, catalytic reforming plants, aromatic hydrocarbon plants, disproportionation, isomerization processes and the like will produce a large amount of C10 aromatic hydrocarbons as by-products. Therefore, how to effectively utilize the C10 aromatic hydrocarbon resource has become an important issue in petrochemical industry. As an important intermediate of fine chemicals with high added value, pyromellitic dianhydride (PMDA, pyromellitic dianhydride) with a special structure of 4 symmetrical carboxyl groups can be prepared into a plurality of products with excellent heat resistance, electric insulation and chemical resistance. The product can be mainly used for producing monomers, medical intermediates, epoxy resin curing agents and the like of polyimide, polyimidazole and other heat-resistant resins, and products prepared from the product can be widely applied to advanced technical fields of aviation, aerospace, electronic industry and the like. Therefore, the pyromellitic dianhydride which is extracted from the pyromellitic dianhydride with high content of C10 aromatic hydrocarbon as a refining byproduct and is further processed into high added value has very important research significance and obvious economic benefit.
at present, a gas-phase oxidation method is mostly adopted for preparing the pyromellitic anhydride by taking durene as a raw material, and the process is a complex heterogeneous catalysis process and has various side reactions, so that the yield of the pyromellitic anhydride is very low. The catalyst for preparing the homoanhydride by the gas phase oxidation method mainly takes a vanadium system as an active component, a small amount of metal elements are used as auxiliary materials, the theoretical yield of the homoanhydride is calculated according to a chemical reaction equation and is up to 163%, but the catalyst obtained by the traditional preparation method is relatively low in activity, and the actual yield of the homoanhydride can only reach 56% of the theoretical yield at most. Therefore, it is necessary to improve the selectivity of the catalyst to the homoanhydride by changing the preparation method of the catalyst.
US 4665200 discloses a multi-system catalyst with active components comprising V, Ti, P, Nb and Sb elements, which has a longer lifetime. CN 102008971 reports a catalytic system using V-Ti as a main catalyst and alkali metal as a cocatalyst, and good catalytic effect can be obtained. JP 45-15252 discloses a V-Ti-Na catalyst with some improvement in the yield of the pyromellitic anhydride. The method makes great progress in the preparation of the catalyst for preparing the pyromellitic anhydride by oxidizing durene, but still has the problem of low yield of the pyromellitic anhydride.
Disclosure of Invention
One of the technical problems to be solved by the invention is the problem of low yield of the pyromellitic anhydride in the prior art, and the catalyst for synthesizing the pyromellitic anhydride from durene is provided and has the characteristic of high yield of the pyromellitic anhydride.
The second technical problem to be solved by the present invention is to provide a method for preparing a catalyst corresponding to the first technical problem.
The invention aims to solve the third technical problem and provide a method for synthesizing the pyromellitic anhydride from the durene, which corresponds to the solution of one of the technical problems.
In order to solve one of the technical problems, the technical scheme disclosed by the invention is that the catalyst for synthesizing the pyromellitic anhydride from the durene is characterized in that the catalyst adopts alpha-Al 2 O 3, silicon carbide, a ceramic ring or a mixture thereof as a carrier, and an active component comprises vanadium, a nonmetal element and at least one of a VA group element and a IIIB group element.
In the above technical solution, the nonmetal element is selected from at least one of B, Si, As and Te. More preferably B and Si.
In the above technical solution, the VA group element is selected from at least one of P, Sb, and Bi.
In the above technical solution, the group iiib element is at least one selected from Sc and Y.
In the above technical solutions, as the most preferable technical solution, the active component simultaneously includes a vanadium element, a nonmetal element, a VA group element, and a iiib group element; for example, the active components include V, Si, P and Sc, or V, B, Bi, Sc and Y, or V, Si, P, Bi, Sc and Y, or V, B, Si, P, Bi, Sc and Y.
in the technical scheme, the ratio of vanadium element to nonmetal element in the catalyst is 1 (1-10), and more preferably 1 (3-8); the ratio of vanadium element to sum of VA group element and IIIB group element in the catalyst is 1: (0.01-1), more preferably 1: (0.02-0.5).
To solve the second technical problem, the technical solution of the present invention is as follows: the preparation method of the catalyst for synthesizing the pyromellitic anhydride from durene, which is described in the technical scheme of one of the technical problems, comprises the following steps:
(1) Adding a vanadium source into an oxalic acid solution to obtain a mixed solution; adding a non-metal element, a VA group element and a IIIB group element compound into a reaction system to obtain a precursor;
(2) Spraying the precursor on a carrier, and roasting to obtain the catalyst.
In the above technical solution, the vanadium source in step (1) is preferably at least one selected from vanadium oxide, metavanadate, orthovanadate and vanadium chloride. The compound of the nonmetallic element in step (1) is preferably at least one selected from silicon oxide, silicate, silicic acid, chlorosilane, borate, arsenic oxide, methyl arsenic, methyl arsonic acid and arsenate. The compound of the VA group element in the step (1) is preferably at least one selected from phosphoric acid, ammonium dihydrogen phosphate, diammonium hydrogen phosphate, bismuth nitrate, bismuth sulfate, bismuth halide and bismuth acetate. The compound of the group IIIB element in step (1) is preferably at least one selected from the group consisting of scandium oxide, scandium halide, scandium sulfate, yttrium oxide, and yttrium fluorite.
In the technical scheme, the preparation method for synthesizing the pyromellitic dianhydride catalyst is characterized in that a precursor of the catalyst is loaded into a spraying machine, and is uniformly sprayed on a carrier after being heated at the temperature of 190-260 ℃.
In the technical scheme, the preparation method for the catalyst for synthesizing the pyromellitic anhydride from the durene is characterized in that the carrier sprayed with the catalyst precursor is roasted in a muffle furnace, the roasting temperature is 480-580 ℃, and the roasting time is 1-10 h.
To solve the third technical problem, the technical scheme of the invention is as follows: the synthesis process of sym-anhydride with durene and air as material adopts fixed bed reactor and in the presence of catalyst.
The technical scheme is characterized in that the mass concentration of durene is 25-60g/m 3, the reaction process conditions are that the space velocity is 4000-6500 hr -1, the reaction temperature is 200-600 ℃, and the reaction pressure is normal pressure.
Compared with the prior art, the key point of the invention is that the active component of the catalyst comprises a certain amount of vanadium element, nonmetal element and at least one element selected from VA group element and IIIB group element, which is beneficial to improving the activity and stability of the catalyst, thereby improving the yield of the pyromellitic dianhydride.
The experimental result shows that the yield of the pyromellitic dianhydride prepared by the invention reaches 78.6%, and a better technical effect is achieved, particularly when the active component in the catalyst simultaneously comprises vanadium element, nonmetal element, at least one metal element selected from VA group elements and at least one metal element selected from IIIB group elements, a more prominent technical effect is achieved, and the catalyst can be used for synthesis of pyromellitic dianhydride. The invention is further illustrated by the following examples.
Detailed Description
[ example 1 ]
Weighing 85g of oxalic acid and 320ml of distilled water in a flask, stirring and heating to 88 ℃, preparing an oxalic acid solution after the oxalic acid is completely dissolved, adding 1 part of ammonium metavanadate into the prepared oxalic acid solution, continuously stirring to obtain an ammonium vanadyl oxalate solution, adding 8 parts of boric acid and 0.4 part of bismuth nitrate into the solution, continuously stirring uniformly to obtain a catalyst precursor, filtering and drying the catalyst precursor, putting the dried catalyst precursor into a spraying machine, uniformly spraying the catalyst precursor on silicon carbide serving as an inert carrier, roasting the inert carrier sprayed with the catalyst precursor in a muffle furnace at 520 ℃, naturally cooling to obtain the catalyst, evaluating the catalyst in a fixed bed reactor at 480 ℃ and an airspeed of 0h -1, obtaining the yield of the homogeneous anhydride of 74.7%, and obtaining evaluation results detailed in Table 1.
[ example 2 ]
Weighing 85g of oxalic acid and 320ml of distilled water in a flask, stirring and heating to 88 ℃, preparing an oxalic acid solution after the oxalic acid is completely dissolved, adding 1 part of ammonium metavanadate into the prepared oxalic acid solution, continuously stirring to obtain an ammonium vanadyl oxalate solution, adding 8 parts of boric acid and 0.4 part of scandium sulfate into the solution, continuously stirring uniformly to obtain a catalyst precursor, filtering and drying the catalyst precursor, putting the dried catalyst precursor into a spraying machine, uniformly spraying the dried catalyst precursor on silicon carbide serving as an inert carrier, roasting the inert carrier sprayed with the catalyst precursor in a muffle furnace at 520 ℃, naturally cooling to obtain the catalyst, evaluating the catalyst in a fixed bed reactor at 480 ℃ and an airspeed of 0h -1, obtaining the yield of the homogeneous anhydride of 74.4%, and obtaining evaluation results detailed in Table 1.
comparative example 1
Weighing 85g of oxalic acid and 320ml of distilled water in a flask, stirring and heating to 88 ℃, preparing an oxalic acid solution after the oxalic acid is completely dissolved, adding 1 part of ammonium metavanadate into the prepared oxalic acid solution, continuously stirring to obtain an ammonium vanadyl oxalate solution, adding 8 parts of boric acid into the solution, continuously stirring uniformly to obtain a catalyst precursor, filtering and drying the catalyst precursor, filling the catalyst precursor into a spraying machine, uniformly spraying the catalyst precursor on an inert carrier for carbonization, roasting the inert silicon carrier sprayed with the catalyst precursor in a muffle furnace at 520 ℃, naturally cooling to obtain the catalyst, evaluating the catalyst in a fixed bed reactor at 480 ℃ and an airspeed of 5300h -1, and obtaining the yield of the homogeneous anhydride of 74.7%, wherein the evaluation results are detailed in Table 1.
Compared with the examples 1-2, the catalyst adopted by the invention has the advantages that the performance of the catalyst containing V, B and Bi active components and V, B and Bi active components is better than that of the catalyst containing V, B active components, and the yield of the pyromellitic dianhydride is higher.
[ example 3 ]
Weighing 85g of oxalic acid and 320ml of distilled water in a flask, stirring and heating to 88 ℃, preparing an oxalic acid solution after the oxalic acid is completely dissolved, adding 1 part of vanadium pentoxide into the prepared oxalic acid solution, continuously stirring to obtain an ammonium vanadyl oxalate solution, adding 8 parts of trichlorosilane and 0.4 part of ammonium dihydrogen phosphate into the solution, continuously stirring uniformly to obtain a catalyst precursor, filtering and drying the catalyst precursor, filling the catalyst precursor into a spraying machine, uniformly spraying on an inert carrier silicon carbide, roasting the inert carrier sprayed with the catalyst precursor in a muffle furnace at 520 ℃, naturally cooling to obtain the catalyst, evaluating the catalyst in a fixed bed reactor at a reaction temperature of 480 ℃ and an airspeed of 5300h -1 to obtain an average anhydride yield of 74.5%, wherein the evaluation results are detailed in table 1.
[ example 4 ]
Weighing 85g of oxalic acid and 320ml of distilled water in a flask, stirring and heating to 88 ℃, preparing an oxalic acid solution after the oxalic acid is completely dissolved, adding 1 part of vanadium pentoxide into the prepared oxalic acid solution, continuously stirring to obtain an ammonium vanadyl oxalate solution, adding 8 parts of boric acid and 0.4 part of diammonium hydrogen phosphate into the solution, continuously stirring uniformly to obtain a catalyst precursor, filtering and drying the catalyst precursor, putting the dried catalyst precursor into a spraying machine, uniformly spraying the dried catalyst precursor on silicon carbide serving as an inert carrier, roasting the inert carrier sprayed with the catalyst precursor in a muffle furnace at 520 ℃, naturally cooling to obtain the catalyst, evaluating the catalyst in a fixed bed reactor at 480 ℃ and an airspeed of 0h -1, obtaining the yield of the homogeneous anhydride of 74.8 percent, and obtaining evaluation results detailed in Table 1.
[ example 5 ]
Weighing 85g of oxalic acid and 320ml of distilled water in a flask, stirring and heating to 88 ℃, preparing an oxalic acid solution after the oxalic acid is completely dissolved, adding 1 part of ammonium metavanadate into the prepared oxalic acid solution, continuously stirring to obtain an ammonium vanadyl oxalate solution, adding 8 parts of trichlorosilane and 0.4 part of yttrium oxide into the solution, continuously stirring uniformly to obtain a catalyst precursor, filtering and drying the catalyst precursor, putting the catalyst precursor into a spraying machine, uniformly spraying on an inert carrier silicon carbide, roasting the inert carrier sprayed with the catalyst precursor in a muffle furnace at 520 ℃, naturally cooling to obtain the catalyst, evaluating the catalyst in a fixed bed reactor at the reaction temperature of 480 ℃ and the airspeed of 5300h -1 to obtain the yield of 74.6 percent of homogeneous anhydride, wherein the evaluation results are detailed in table 1.
[ example 6 ]
Weighing 85g of oxalic acid and 320ml of distilled water in a flask, stirring and heating to 88 ℃, preparing an oxalic acid solution after the oxalic acid is completely dissolved, adding 1 part of vanadium pentoxide into the prepared oxalic acid solution, continuously stirring to obtain an ammonium vanadyl oxalate solution, adding 8 parts of boric acid and 0.4 part of scandium sulfate into the solution, continuously stirring uniformly to obtain a catalyst precursor, filtering and drying the catalyst precursor, putting the dried catalyst precursor into a spraying machine, uniformly spraying the dried catalyst precursor on silicon carbide serving as an inert carrier, roasting the inert carrier sprayed with the catalyst precursor in a muffle furnace at 520 ℃, naturally cooling to obtain the catalyst, evaluating the catalyst in a fixed bed reactor at 480 ℃ and an airspeed of 0h -1, obtaining the yield of the homogeneous anhydride of 74.9%, and obtaining evaluation results detailed in Table 1.
[ example 7 ]
Weighing 85g of oxalic acid and 320ml of distilled water in a flask, stirring and heating to 88 ℃, preparing an oxalic acid solution after the oxalic acid is completely dissolved, adding 1 part of ammonium metavanadate into the prepared oxalic acid solution, continuously stirring to obtain an ammonium vanadyl oxalate solution, adding 8 parts of boric acid, 0.2 part of bismuth nitrate and 0.2 part of scandium sulfate into the solution, continuously stirring uniformly to obtain a catalyst precursor, filtering and drying the catalyst precursor, putting the catalyst precursor into a spraying machine, uniformly spraying on an inert carrier silicon carbide, roasting the inert carrier sprayed with the catalyst precursor in a muffle furnace at 520 ℃, naturally cooling to obtain the catalyst, and evaluating the catalyst in a fixed bed reactor at the reaction temperature of 480 ℃ and the airspeed of 5300h -1 to obtain the yield of the homogeneous anhydride of 75.8%, wherein the evaluation results are detailed in table 1.
Compared with the examples 1-2, the VA group Bi element and the IIIB group Sc element have better synergistic effect on improving the yield of the homogeneous anhydride.
[ example 8 ]
Weighing 85g of oxalic acid and 320ml of distilled water in a flask, stirring and heating to 88 ℃, preparing an oxalic acid solution after the oxalic acid is completely dissolved, adding 1 part of ammonium metavanadate into the prepared oxalic acid solution, continuously stirring to obtain an ammonium vanadyl oxalate solution, adding 8 parts of boric acid, 0.1 part of bismuth nitrate, 0.1 part of ammonium dihydrogen sulfate and 0.2 part of scandium sulfate into the solution, continuously stirring uniformly to obtain a catalyst precursor, filtering and drying the catalyst precursor, filling the catalyst precursor into a spraying machine, uniformly spraying on an inert carrier silicon carbide, roasting the inert carrier sprayed with the catalyst precursor in a muffle furnace at 520 ℃, naturally cooling to obtain the catalyst, evaluating the catalyst in a fixed bed reactor at the reaction temperature of 480 ℃ and the airspeed of 5300h -1, measuring the yield of the homogeneous anhydride to be 76.1%, and obtaining the evaluation result of the catalyst in Table 1.
Compared with example 7, this example shows that the Bi element and the P element in the VA group have better synergistic effect with other active components in the invention in improving the yield of the pyromellitic dianhydride.
[ example 9 ]
Weighing 85g of oxalic acid and 320ml of distilled water in a flask, stirring and heating to 88 ℃, preparing an oxalic acid solution after the oxalic acid is completely dissolved, adding 1 part of ammonium metavanadate into the prepared oxalic acid solution, continuously stirring to obtain an ammonium vanadyl oxalate solution, adding 8 parts of boric acid, 0.2 part of bismuth nitrate, 0.1 part of scandium sulfate and 0.1 part of yttrium chloride into the solution, continuously stirring uniformly to obtain a catalyst precursor, filtering and drying the catalyst precursor, putting the catalyst precursor into a spraying machine, uniformly spraying on an inert carrier silicon carbide, roasting the inert carrier sprayed with the catalyst precursor in a muffle furnace at 520 ℃, naturally cooling to obtain the catalyst, evaluating the catalyst in a fixed bed reactor at 480 ℃, airspeed 5300h -1, measuring the yield of the homogeneous anhydride to be 76.9%, and obtaining the evaluation results of the evaluation are detailed in table 1.
In this example, it can be seen from comparison with example 7 that the group IIIB Sc and Y elements have a better synergistic effect with the other active components of the present invention in increasing the yield of the homoanhydride.
[ example 10 ]
Weighing 85g of oxalic acid and 320ml of distilled water in a flask, stirring and heating to 88 ℃, preparing an oxalic acid solution after the oxalic acid is completely dissolved, adding 1 part of ammonium metavanadate into the prepared oxalic acid solution, continuously stirring to obtain an ammonium vanadyl oxalate solution, adding 8 parts of boric acid, 0.1 part of bismuth nitrate, 0.1 part of ammonium dihydrogen sulfate, 0.1 part of scandium sulfate and 0.1 part of yttrium chloride into the solution, continuously stirring uniformly to obtain a catalyst precursor, filtering and drying the catalyst precursor, putting the catalyst precursor into a spraying machine, uniformly spraying on silicon carbide serving as an inert carrier, roasting the inert carrier sprayed with the catalyst precursor in a muffle furnace at 520 ℃, naturally cooling to obtain the catalyst, and evaluating the catalyst in a fixed bed reactor at the reaction temperature of 480 ℃ and the airspeed of 5300h -1 to obtain the average yield of 77.8%, wherein the evaluation results are detailed in Table 1.
In this example, it can be seen that, compared with examples 8 and 9, V, nonmetallic B element, VA group Bi and P element, and iiib group Sc and Y element have very good synergistic effect in increasing the yield of the homogeneous anhydride.
[ example 11 ]
Weighing 85g of oxalic acid and 320ml of distilled water in a flask, stirring and heating to 88 ℃, preparing an oxalic acid solution after the oxalic acid is completely dissolved, adding 1 part of ammonium metavanadate into the prepared oxalic acid solution, continuously stirring to obtain an ammonium vanadyl oxalate solution, adding 8 parts of boric acid, 0.1 part of bismuth nitrate, 0.1 part of ammonium dihydrogen sulfate, 0.1 part of scandium sulfate and 0.1 part of yttrium chloride into the solution, continuously stirring uniformly to obtain a catalyst precursor, filtering and drying the catalyst precursor, putting the catalyst precursor into a spraying machine, uniformly spraying on silicon carbide serving as an inert carrier, roasting the inert carrier sprayed with the catalyst precursor in a muffle furnace at 520 ℃, naturally cooling to obtain the catalyst, and evaluating the catalyst in a fixed bed reactor at the reaction temperature of 480 ℃ and the airspeed of 5300h -1 to obtain the average yield of 78.6%, wherein the evaluation results are detailed in Table 1.
Compared with example 10, this example shows that V, nonmetal B, Si element, VA group Bi and P element, and iiib group Sc and Y element have very good synergistic effect in increasing the yield of pyromellitic anhydride.
TABLE 1
Claims (5)
1. The catalyst for synthesizing pyromellitic dianhydride by oxidizing pyromellitic dianhydride is characterized in that alpha-Al 2 O 3, silicon carbide, a ceramic ring or a mixture thereof is used As a carrier, active components comprise vanadium elements, nonmetal elements, VA group elements and IIIB group elements, the IIIB group elements comprise Sc and Y, the nonmetal elements are selected from at least one of B, Si, As and Te, the VA group elements are selected from at least one of P, Sb and Bi, the molar ratio of the vanadium elements to the nonmetal elements in the catalyst is 1 (1-10), and the molar ratio of the vanadium elements to the sum of the VA group elements and the IIIB group elements is 1 (0.01-1).
2. a process for the preparation of a catalyst for the oxidation of pyromellitic dianhydride according to claim 1, comprising the steps of:
(1) Adding a vanadium source into an oxalic acid solution to obtain a mixed solution; adding a non-metal element, a VA group element and a IIIB group element compound into a reaction system to obtain a precursor;
(2) Spraying the precursor on a carrier, and roasting to obtain the catalyst.
3. The method according to claim 2, wherein the precursor of the catalyst is loaded into a spray coater, heated at 190-260 ℃ and uniformly sprayed on the carrier.
4. The method of claim 2, wherein the carrier coated with the catalyst precursor is calcined in a muffle furnace at 480-580 ℃ for 1-10 h.
5. A process for synthesizing sym-anhydride from sym-tetramethylbenzene includes such steps as using sym-tetramethylbenzene and air as raw materials, fixed-bed reactor, mass concentration of sym-tetramethylbenzene being 25-60g/m 3, and reaction at 4000-6500 hr -1, 200-600 deg.C and normal pressure under existance of catalyst as claimed in claim 1.
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