138 results about "Formylation reaction" patented technology

The invention discloses a system device and a method for producing aldehyde compounds through supergravity two-phase hydroformylation. The system device comprises a supergravity reactor, a buffer tank, a first circulating pump, a tower kettle heat exchanger, a circulating heat exchanger, a split-phase tank, a second circulating pump, a crude aldehyde transfer pump, a supergravity rectification unit, a tower kettle reboiler, a product extraction pump and a cold and hot all-in-one machine. According to the system device, under the condition that a polar solvent and a surfactant are not added, the two-phase hydroformylation reaction process can be greatly enhanced through the supergravity reactor, the technological process is shortened, and then a product is separated and purified through the supergravity rectification unit to obtain an aldehyde compound; the problems of low two-phase hydroformylation reaction efficiency, serious self-polymerization in a hydroformylation product purification process and the like in the prior art are solved; by utilizing the method, the olefin conversion rate is more than 90%, the aldehyde selectivity of the product is more than 99%, the purity of the purified product is more than 99%, and the loss amount of the catalyst is less than or equal to 0.5 mg / kg.

This invention belongs to the field of homogeneous catalysis technology, and particularly relates to a method for the hydroformylation of propylene to prepare isobutyraldehyde. The method includes: in the presence of a bidentate P-N ligand and a rhodium metal compound, introducing propylene and syngas to carry out a hydroformylation reaction to prepare isobutyraldehyde. The structural formula of the bidentate P-N ligand is as follows: [Insert structural formula here]. Wherein, R1 is selected from one of C2-C4 alkyl groups, substituted or unsubstituted phenyl groups; R2 is selected from one of hydrogen, C1-C4 alkyl groups, alkoxy groups, substituted or unsubstituted phenyl groups. This method provides a highly active P-N ligand, which, while reducing the amount of rhodium catalyst, maintains high activity and can significantly improve the conversion rate of propylene, as well as the selectivity and yield of isobutyraldehyde.

A process for producing an aldehyde is disclosed. The process comprises: hydroformylating an olefin to form the aldehyde using a hydroformylation catalyst; recovering an effluent stream comprising the aldehyde, hydrogen and the hydroformylation catalyst; passing the effluent stream to a stripper; contacting the effluent stream with a strip gas in the stripper to produce a stripped effluent stream having a lower hydrogen concentration than the effluent stream; and recovering the stripped effluent stream.

The present application provides a catalyst for preparing oxygen-containing compounds by olefin hydroformylation reaction, and a preparation method and use thereof, the catalyst is Fe x Co y M, the catalyst contains 0.1-15wt% M, 85-99.9wt% Fe and Co, the atomic ratio of x to y is 0.1-10, and M is a metal element. When the catalyst is used for preparing oxygen-containing compounds by olefin hydroformylation reaction, the conversion rate of olefin can reach 93-99.9%, and the selectivity of oxygen-containing compounds can reach 89-98.8%; and the catalyst is in a solid state during the reaction, which is easy to realize solid-liquid separation with the product, and also avoids the loss of the catalyst during the separation process.

The utility model belongs to the field of chemical reaction, and particularly relates to an automatic reaction system which comprises a microfluidic device, the microfluidic device is provided with a gas supply module for supplying gas, and the interior of the microfluidic device is used for hydrogenation reaction and hydroformylation reaction; the first mechanical arm module is used for moving a reagent; the first mechanical arm module and the micro-fluidic module are in signal connection with the control module. The utility model provides an automatic reaction system and aims to solve the problem of safety risk of manual operation in the prior art.

This invention provides a method for determining the deactivation temperature and deactivation characteristics of a hydroformylation catalyst, comprising: S1. preparing a hydroformylation reaction solution; S2. measuring the reaction solution and placing it in an adiabatic testing instrument to simulate a hydroformylation reaction, stopping the heating when the temperature reaches T0 and incubating the reaction under adiabatic conditions; recording the temperature change and obtaining the highest temperature T. m S3. After cooling the test ball, remove half of the reactant material, add the hydroformylation reaction raw material, and heat up to simulate the hydroformylation reaction. When the temperature reaches T1, stop heating and perform an adiabatic reaction. Record the highest temperature T. mf S4. Compare T1 and T m and T mf If T mf =T1, catalyst deactivation temperature is T m Irreversible inactivation; if T mf =T m The catalyst deactivation temperature is T m Reversible inactivation; if T mf >T m Remove the material from the test sphere and repeat steps S2 to S4. The judgment method of this invention has a short testing cycle, high safety, and eliminates the need for sample separation and component analysis. It provides guidance for research on catalyst operating limits and the selection of homogeneous catalyst recovery temperatures.

The application provides a method and device for continuously preparing aldehyde compounds through a hydroformylation reaction. The method for continuously preparing aldehyde compounds through the hydroformylation reaction comprises the following steps: using a catalyst to catalyze an olefin raw material and synthetic gas to perform a hydroformylation reaction, so as to obtain a reaction product containing aldehyde compounds; and separating the reaction product, so as to obtain the aldehyde compounds and recover the catalyst. The hydroformylation reaction comprises a homogeneous reaction or a heterogeneous reaction. The method can solve the problem of a large amount of catalyst loss in the hydroformylation reaction in the prior art and is suitable for the field of Fischer-Tropsch synthesis.

The application provides a preparation method of N,N-dimethylformamide (DMF). The method uses carbon dioxide, hydrogen and dimethylamine as reaction raw materials, and N,N-dimethylformamide is prepared through N-formylation of carbon dioxide under the action of a catalyst. The method uses an oxide supported transition metal as the catalyst, the catalyst composition and the preparation method are simple and low in cost, the reaction is carried out in a fixed bed reactor, the reaction continuity is good, the catalyst and the reaction system are easy to separate, the catalyst is convenient to recycle, the reaction condition is relatively mild, the conversion rate of dimethylamine and the selectivity of DMF are high, and the method provides an economic, environment-friendly and effective way for the synthesis of DMF.

The invention belongs to the technical field of chemical synthesis, and relates to a synthesis method of 2, 3-dimethoxybenzaldehyde. According to the invention, o-dimethoxybenzene reacts with butyl lithium in an organic solvent system, and butyl lithium is used as a strong base to'remove 'hydrogen atoms at specific positions in o-dimethoxybenzene molecules, so that an active intermediate 2, 6-dimethoxyphenyl lithium is formed. The intermediate has electronegative phenyl carbon anions, has relatively strong nucleophilic ability, and provides good reaction sites for subsequent formylation reaction, so that the yield of the target product 2, 3-dimethoxybenzaldehyde can reach a relatively high level, the purity of the target product 2, 3-dimethoxybenzaldehyde also reaches an industrial application standard, and the utilization rate of raw materials and the market competitiveness of the product are greatly improved.

The invention discloses a monatomic photocatalytic material as well as a preparation method and application thereof in N-formylation reaction, and aims at innovating a high-energy-consumption and high-risk process for synthesizing traditional N-formylmorpholine and efficiently converting greenhouse gas CO2 into high-added-value chemicals through photocatalytic reaction at normal temperature and normal pressure. According to the catalyst disclosed by the invention, the separation and transfer efficiency of photo-generated charges is remarkably improved by constructing double active sites in which Sb single atoms and MnOx nano-particles are synergistic, in practical application, the catalyst shows excellent performance, the production rate of N-formylmorpholine reaches up to 13.8 mmol g <-1 > h <-1 > under 12-hour illumination, the selectivity exceeds 90%, the activity retention rate exceeds 95% after the catalyst is recycled for 5 times, and the catalyst has a good application prospect. The stability is excellent.

Specifically, a process for controlling heavies in a recycle catalyst stream for use in a continuous hydroformylation process in which olefins are converted with synthesis gas in the presence of a hydroformylation catalyst to form an aldehyde product stream, followed by separation of the catalyst for recycle to the hydroformylation step, comprises removing a crude product stream from a hydroformylation reaction zone, the crude product stream comprising one or more aldehyde products, one or more heavy by-products, a transition metal-organophosphorus ligand complex catalyst, one or more unconverted reactants, and one or more inert lights; providing a water stream; combining the water stream with the crude product stream into an azeotropic vaporizer; removing from the vaporizer an overhead gas stream comprising the one or more aldehyde products, the one or more unconverted reactants, the one or more inert lights, a portion of the water, and a portion of the heavy by-products; a liquid recycle catalyst stream to be sent to the reaction zone, the liquid recycle catalyst stream comprising the transition metal-organophosphorus ligand complex catalyst, a remainder of the aldehyde product, and a remainder of the heavy by-products, as a residue stream from the azeotropic vaporizer, wherein at least 25% of the aldehyde product recovered in the overhead gas stream from the condenser is removed as a water azeotrope.

The present invention addresses the problem of providing a method for producing TCD-DA having less impurities generated as by-products, by depositing materials in a reactor in a batch and performing a hydroformylation rection at a low pressure.　The method for producing tricyclodecane dialdehyde is characterized by depositing a catalyst, dicyclopentadiene, and a solvent in a reactor in a batch, increasing the pressure to 2.0-4.0 MPaG by means of a gas mixture of hydrogen and carbon monoxide, and performing a hydroformylation reaction in the gas mixture in which the molar ratio of hydrogen : carbon monoxide is 90:10 to 100:99.

The invention relates to a preparation method of a pharmaceutical active molecule Azurimoline. According to the present invention, the brand new synthesis method is adopted, and comprises the selective metal-catalyzed Suzuki coupling reaction, the formylation reaction and the condensation reaction, such that the synthesis of the Azaurein can be achieved, and the total yield can be increased to 32.3%. The method is simple in route, the yield is greatly improved compared with that of a traditional method, and efficient and high-selectivity synthesis of Azurimulin is achieved. The novel and efficient preparation method of the pharmaceutical active molecule skeletal muscle relaxant Azumolene and the key intermediate of the pharmaceutical active molecule skeletal muscle relaxant Azumolene is more suitable for industrial production.

The invention relates to the technical field of synthesis of organic compounds, and discloses a synthesis method of boclean flood aldehyde, which is characterized in that 4-tert-butylstyrene is used as a raw material, and the boclean flood aldehyde is prepared through one-step hydroformylation reaction. Rh (CO) 2C5H7O2 and bis (2, 4-dicumyl phenyl) pentaerythritol diphosphite form a composite catalyst, the composite catalyst is matched with triethylamine organic alkali to react under specific process conditions, and a pure product is obtained through vacuum distillation. The method has the advantages of simple process, mild reaction conditions, raw material conversion rate of more than 98%, product yield of more than 80%, purity of more than 98%, easy reagent recovery and small environmental harm, and is suitable for industrial large-scale production.

The invention discloses a novel ketorolac synthesis method, which takes 2-(1H-pyrrole-1-yl) propionitrile as a raw material, and ketorolac is obtained through the steps of cyclization reaction, benzoylation reaction, Vanderson reaction, hydrolysis reaction and the like.

The invention relates to the technical field of organic alcohol synthesis, and discloses a method for synthesizing isononyl alcohol. The method comprises the following steps: (1) mixing octylene, a rhodium catalyst and a phosphine ligand, then introducing synthesis gas into the obtained mixture, and carrying out hydroformylation reaction to obtain isononanal; (2) in the presence of a hydrogenation catalyst, mixing the isononanal with hydrogen for hydrogenation reaction; wherein the phosphine ligand is selected from two or more of triphenyl phosphite, tris (2, 4-di-tert-butylphenyl) phenyl phosphite, triphenylphosphine, 6, 6 '-{[5, 5'-dimethoxy-3, 3 '-bis (2-methyl-2-propyl)-2, 2'-biphenyl diyl] bis (oxy)} bis [dibenzo (d, f) (1, 3, 2) dioxaphosphoheptane] and 4, 5-bis (diphenylphosphine)-9, 9-dimethyl xanthene. According to the method, the conversion rate of mixed octylene in the hydroformylation process and the selectivity and yield of isononyl aldehyde can be remarkably improved, so that the yield of isononyl alcohol is improved, reaction conditions are mild, and the method has remarkable economic value and wide industrial application prospects.

The application discloses a norpinane alkyl carbazole enhanced fluorescent probe for detecting viscosity and a preparation method and application thereof. The application takes norpinone as raw material, and performs a cyclization reaction with phenylhydrazine hydrochloride to obtain a compound TC; the compound TC is subjected to N-alkylation reaction with N,N-dimethyl-3-chloropropylamine to obtain a compound TC-AP; the compound TC-AP is subjected to formylation reaction with phosphorus oxychloride to obtain a compound TC-AP-F; and the compound TC-AP-F is subjected to condensation reaction with 4-(cyanomethyl)-1-methylpyridin-1-yl iodide to obtain a fluorescent probe TC-AP-A. The probe TC-AP-A can specifically recognize viscosity, and the red fluorescence of the solution is gradually enhanced with the continuous increase of the viscosity of the system, and the minimum detection limit is 1.41 cP. The probe has the advantages of simple synthesis, good selectivity, high sensitivity, good biocompatibility, low toxicity and the like, and has a good application prospect.

The application provides a method for synthesizing branched aldehyde with high selectivity through a hydroformylation reaction. Through a simple two-step treatment method, only by changing one or more of the gas phase composition, temperature and pressure, the terminal olefin is isomerized into an internal olefin, and then the branched aldehyde product is synthesized with high selectivity through hydroformylation. The method uses a heterogeneous catalyst without phosphine ligand, is environment-friendly, and has the advantages of simple operation steps, cheap and easily available raw materials, and easy separation of the catalyst and the product.

To provide a good method for hydroformylation. [Solution] The present invention relates to a hydroformylation reaction method. In one embodiment, the hydroformylation reaction method includes (a) contacting an olefin with hydrogen and carbon monoxide in the presence of a homogeneous catalyst in a reactor to provide a reaction fluid, the reactor comprising one or more reaction zones; (b) removing a portion of the reaction fluid from a first reaction zone; (c) passing at least a portion of the removed reaction fluid through a shear mixer to generate bubbles in the portion of the removed reaction fluid, the hydrogen and carbon monoxide supplied to the reactor being introduced through the shear mixer; and (d) returning the removed reaction fluid to the first reaction zone through one or more nozzles, the returned reaction fluid coming out of each nozzle being a jet, the mixing energy density supplied to the reactor by the jet being 500 watts / m³ 3 That's all.

This invention discloses a bimetallic catalyst, its preparation method, and its applications. The bimetallic catalyst comprises pretreated graphene oxide and rhodium and nickel supported on the graphene oxide, wherein the molar ratio of nickel to rhodium is 1:10-300. The bimetallic catalyst of this invention exhibits higher activity and selectivity in the hydroformylation reaction of olefins, and also shows good recovery performance after the reaction. The separated catalyst composition can be recycled, reducing production costs and facilitating industrial production applications.

The invention relates to the technical field of organic synthesis, and discloses a synthesis process of salicylaldehyde. The process sequentially comprises three core stages: firstly, performing mechanochemical ball milling pretreatment on phenol, a catalytic complexing agent and a molecular sieve drying agent in an inert atmosphere; then, transferring the pretreated mixture into a reactor containing a composite solvent of sulfolane and ionic liquid [BMIM] PF6, and dropwise adding a hexamethylenetetramine solution under programmed temperature control to perform formylation reaction; and finally, cooling the reaction liquid, filtering, hydrolyzing the filtrate by using a phosphoric acid aqueous solution with gradient concentration, and separating the product in real time through azeotropic distillation. According to the process, mechanical activation, composite solvent and programmed reaction are combined, the process is continuous, and the reaction efficiency and selectivity are improved.

The invention discloses a method for establishing a prediction model of an olefin hydroformylation reaction result based on a random forest and XGBoost. The method comprises the following steps: a data acquisition step: extracting a data set for converting hydroformylation of related olefin into aldehyde from database query; the data set comprises reaction conditions and experimental results of aldehyde yield and linear selectivity; the reaction conditions of the olefin hydroformylation reaction comprise the structure of the pre-catalyst, the ratio of the substrate to the pre-catalyst, the solvent, the temperature, the time and the pressure; a feature extraction step: optimizing the data set based on the random forest, establishing a random forest model on the initial data set, giving importance evaluation of input parameters by the random forest model, quantitatively screening out important input parameters in an experimental result for predicting the olefin hydroformylation reaction, and processing the initial data so as to form an optimized data set; and a model establishment step: establishing an XGBoost model based on the optimized data set and optimizing the XGBoost model to obtain an intelligent prediction model.

The invention provides a preparation method of a diphosphine ligand and a hydroformylation reaction method, and relates to the technical field of catalysts. The preparation method is as shown in a reaction formula (A) or a reaction formula (B), under the action of first Lewis acid, a compound as shown in a formula (1) and a compound as shown in a formula (2.1) or a formula (2.2) are subjected to an electrophilic substitution reaction, the reacted material is extracted, concentrated and recrystallized, and the diphosphine ligand as shown in a formula (3.1) or a formula (3.2) is obtained; reaction formula (A); reaction formula (B); according to the preparation method of the diphosphine ligand, the technological process is simple, the reaction system is simplified, the use of flammable and explosive organic lithium reagents can be avoided, the safety is improved, and the high-purity diphosphine ligand can be obtained. The diphosphine ligand prepared by the invention can catalyze the enol hydroformylation reaction to be efficiently carried out, so that the enol conversion rate is not less than 99%, the product selectivity is not less than 95%, and the normal / isomeric ratio of the prepared aldehyde product is greater than 30.

The invention relates to an ionic carbonyl cobalt-phosphine complex. The complex has a structure as shown in a formula I, wherein R1 to R8 are respectively any one of independently aryl, benzyl or cycloalkylene formed in pairs; x is an integer of 1-3; y is a counter anion; the xanthene ligand is any one of phenyl, diphenyl ether group, xanthene group, biphenyl group, dinaphthyl group, silyl group and cyclosiloxy / nitrogen alkyl ligand skeleton; and the dotted line part only represents a complex structure composed of tridentate or more phosphine compounds and cobalt. Meanwhile, the invention also discloses a synthesis method and application of the complex. The synthesis method is simple and high in yield, and the obtained ionic carbonyl cobalt-phosphine complex has more excellent stability and oxidation resistance, is more convenient to store, transport and use in long-period hydroformylation reaction, has the advantages of being capable of being separated, recycled and reused and the like, and is more suitable for industrial amplification application.

The application discloses a supported metal cluster catalyst and a preparation method thereof. The supported metal cluster catalyst is metal clusters wrapped in an aerogel carrier. In the application, the metal clusters are wrapped in the aerogel in situ in the process of synthesizing the aerogel, and a stable catalyst is obtained. When the catalyst is applied to a carbon dioxide hydroformylation reaction, the integration of carbon dioxide capture and efficient utilization can be realized without adding an external additive. The catalyst has excellent catalytic activity and selectivity, and the regeneration process is simple, environment-friendly and recyclable, so the catalyst has great industrial application prospect.

This invention discloses a porous carbon-supported copper catalyst, its preparation method, and its application, belonging to the field of catalyst preparation technology. The invention uses three-dimensional interconnected ordered porous carbon (NCP) with a large-pore structure as a support, tetraphenylporphyrin copper(II) and tetraphenylporphyrin as nitrogen and copper sources, and KOH or NaOH as activators. An NCP precursor adsorbed with tetraphenylporphyrin copper(II), tetraphenylporphyrin, and an alkaline component is obtained through a two-step adsorption process. This precursor is then pyrolyzed at 600-900℃ under nitrogen protection, cooled to room temperature, and washed with water to obtain the porous carbon-supported copper catalyst (NCP@NC-Cu). This catalyst retains a three-dimensional interconnected porous structure, with the active component (copper species) mainly distributed within the pores of the NCP support, and possesses a large specific surface area and abundant nitrogen. The catalyst was applied to the N-formylation reaction of amines with CO2 and H2 to prepare formamide compounds, exhibiting excellent catalytic activity, recyclability, and good substrate versatility, showing promising application prospects.

The invention provides a preparation method of a bisphosphite ligand and an olefin hydroformylation reaction method. The preparation method of the ligand comprises the following steps: in the presence of a first solvent and a reaction aid, carrying out contact reaction on a compound as shown in a formula (A) and at least one compound as shown in a formula (B); removing the reacted material by using a solvent, and recrystallizing to obtain a bisphosphite ligand; the formula (A), the formula (B) and R1-R16 are respectively and independently selected from hydrogen, alkyl, cycloalkyl, heterocyclic cycloalkyl, aryl, heteroaryl, alkoxy, cycloalkyloxy, heterocyclic cycloalkyloxy, aryloxy, heteroaryloxy, carboxyl, carboxylate, sulfonic acid group, sulfonate, halogen, nitryl, acyl or cyano; the reaction aid is selected from at least one of anhydrous potassium carbonate, anhydrous sodium carbonate, anhydrous lithium carbonate, potassium hydroxide, sodium hydroxide and lithium hydroxide, and the reaction aid is powder with the particle size not larger than 200 microns; the prepared ligand can promote high-stability catalytic olefin hydroformylation reaction, and an aldehyde product with a high normal / isomer ratio is obtained.

The invention relates to the technical field of organic alcohol preparation, and discloses a method for preparing iso-tridecanol from Fischer-Tropsch olefin. The method comprises the following steps: (1) mixing a Fischer-Tropsch C6 fraction section, aluminum alkyl and a supported metal, and then introducing hydrogen into the obtained mixture for polymerization reaction to obtain isododecene; (2) mixing the isododecene, a cobalt catalyst and a diphosphine ligand, then introducing synthesis gas into the obtained reaction mixture, and carrying out hydroformylation reaction to obtain isotridecanal; and (3) in the presence of a hydrogenation catalyst, mixing the iso-tridecanal with hydrogen to carry out aldehyde hydrogenation reaction. The method has the characteristics of easily available raw materials, high conversion rate, good selectivity, high yield of iso-tridecanol, mild reaction conditions and relatively strong process stability, and the method is simple and convenient to operate and good in economic benefit, highly conforms to large-scale industrial production requirements, and shows remarkable economic value and wide industrial application prospects.

Disclosed is a catalyst composition comprising: (a) a transition metal; and (b) a diphosphoramidite ligand having the structure of formulas (I), (II), or (III): The catalyst composition is particularly useful for the hydroformylation of olefins to form aldehydes.

The invention relates to the technical field of olefin hydroformylation, and discloses a method for olefin hydroformylation by using crude hydrogen, an olefin hydroformylation reaction system and application thereof, the method comprises the following steps: in the presence of an ester compound, olefin, crude hydrogen and a catalytic material are contacted for reaction to obtain an olefin hydroformylation product; the catalytic material comprises a first active component and a second active component, the first active component is Cu, and the second active component is Rh; wherein in the crude hydrogen, the volume ratio of H2 to CO is 0.1 to 10. According to the method, crude hydrogen can be directly used for olefin formylation reaction, olefin hydroformylation and ester hydrogenation are realized at the same time, redundant hydrogen components are captured and removed through esters, and residual optimized composition gas is used for olefin hydroformylation, so that production of high-value chemicals is realized.