The method of obtaining a mixture of 2-methyl-1-naphthol, 2,4-dimethyl-1 - naphthol

 

(57) Abstract:

Usage: substituted condensed aromatic compounds, alkylation of the alcohol, the initial products of the synthesis of vitamin K3. The inventive catalytic vapor-phase methylation of 1-naphthol with methanol is carried out at 250-380°C., a molar ratio of 1-naphthol:methanol = 1:(5-10), space velocity of the raw material 100-1000 h-1. The catalyst contains iron oxide (3), vanadium (5) and manganese (2) in the following ratio, wt.%: Fe2O343-50, V2O5(42-51), MnO - rest. Get a mixture of 2-methyl-1-naphthol, 2,4-dimethyl-1-naphthol. table 1.

The invention relates to the field of organic synthesis, namely to obtain methylated napolov, in particular a mixture of 2-methyl-1-naphthol, 2,6-dimethyl-1-naphthol used as feedstock for the synthesis of 2-methyl-1,4-naphthoquinone - synthetic vitamin K3(menadione).

Synthesis of 2-methyl-1,4-naphthoquinone (menadione), having the properties of vitamin K3by oxidation of 4-R-2-methyl-1-Naftalan, where R = a) H, b) CH3received on this application may be used as the basis for a new waste technologies. Existing industrial method of obtaining menadi the quality of wastewater 15 times the mass of the product, the abundance of toxic waste in excess of the weight of product in 25 times.

A method of obtaining 2-methyl-1-naphthol by methylation of 1-naphthol in methanol at 320-380aboutAnd pressure 21-35 kgf/cm2in terms of liquid-phase oxidation at a molar ratio methanol : 1-naphthol 0.1-1, in the presence of a solvent is toluene, xylene, mesitylene, naphthalene or water and a catalyst of aluminum oxide at the flow rate of liquid raw materials equal to 1-10 h-1.

The degree of conversion of 1-naphthol in this way is 39-49%; the yield of 2-methyl-1-naphthol 32,37-40.7 per cent.

The disadvantage of this method is the low output of the basic substance - 2-methyl-1-naphthol, sections 32-40,7%, low rate of conversion of 1-naphthol, reaching 39-49%, high pressure 21-35 kgf/cm2require the establishment of special equipment for carrying out this reaction, the presence of a solvent and unreacted 1-naphthol, leading to increased energy costs associated with the separation of reactional mixture.

The closest to the technical essence and the achieved result is a method of obtaining 2-methyl-1-naphthol by methylation of 1-naphthol, metanol the grow 100-5000 h-1the temperature of 300-500aboutC and a pressure of 0.5 to 20 kgf/cm2catalyst consisting of oxides of cerium, antimony, germanium, tin and magnesium.

The yield of 2-methyl-1-naphthol is 54.8-95.2 per cent.

The disadvantage of this method is the low yield of 2-methyl-1-naphthol average of 54.8-95.2 per cent, the highest temperature methylation contributing to the high energy intensity of production, and the presence of unreacted 1-naphthol and/or other methylated 1-Naftalan in the reaction products, leading to the holding of additional stages of purification of the target product from the side. The presence of the original 1-naphthol and/or 4-methyl-1-naphthol in quantities of 3% in methylated 1-Naftalan with their oxidation in menadione significantly reduces the yield of the final product of menadione, having the properties of vitamin K3.

The aim of the invention is to increase output and simplify the process of obtaining methylated 1-Naftalan used directly for the synthesis of 2-methyl-1,4-naphthoquinone, synthetic vitamin K3.

This goal is achieved by the proposed method of obtaining a mixture of methylated 1-Naftalan, including vapor-phase methylation of 1-naphthol with methanol at an elevated pace is talesfore, the distinctive feature of which is the process of methylation at a temperature of 250-380aboutWith the use of a catalyst containing the oxides of vanadium (V), manganese (II) and iron (III) in the following ratio, wt. %: Vanadium oxide 42-51 manganese Oxide 6-8 iron Oxide Rest

Application of the proposed method allows a simpler way to get methylated 1-Naftali formula 4-R-2-methyl-1-naphthol, where R = a) H (2-methyl-1-naphthol), b) -CH3(2,4-dimethyl-1-naphthol), used as feedstock for the synthesis of vitamin K3with the release of 70-98%.

The inventive method is new, as stated set of essential features that characterize the way, on the filing date is unknown.

The comparison of the proposed solutions not only prototype, but also with other technical solutions in this field of technology is not allowed to reveal in them the features distinguishing the claimed solution to the prototype that allows to conclude that the criterion of "substantial differences".

The method is as follows.

To obtain the catalyst is first thoroughly mixed oxides of vanadium, manganese and iron in mass soothe not less than 880aboutWith, the melt is cooled, crushed and classified by fractions.

In a flow type reactor with external heating, internal tube diameter and length, respectively, 14 and 700 mm (laboratory setting) or 27 and 1200 mm (pilot plant), download the fraction of the catalyst with a particle size of 1-2 mm (laboratory setting) or 2-3,5 mm (pilot plant).

The reaction mixture of 1-naphthol: methanol in a molar ratio of 1: (5-10) served in the reactor through the evaporator with a bulk velocity of 100-1000 h-1. The reaction is carried out at a temperature of 250-380aboutAnd pressure of 0-2 kgf/cm2. The products of methylation collect distilled off excess methanol, and the resulting reaction mixture was analyzed on the chromatographic device brand Color 104 using ionization plasma detector and the carrier gas helium, supplied with a speed of 40 ml/min, column of 1 m length, filled with 5% SE-30 on chromaton N-AW-DMCS at the temperature of the column and evaporator 180 and 300aboutRespectively.

Carrying out the methylation reaction of 1-naphthol in methanol at a higher temperature leads to the increase of the content of trimethyl-1-naphthol and the decrease in the output of major products of 2-methyl-1-naphthol, 2,4-dimethyl-1-naphthol, and when Bo is 2">

Carrying out the reaction of methylation at different ratios of the starting components of the reaction mixture leads to the reduction outputs methylated Naftalan or increase the energy cost of the process associated with the distillation of methanol.

The increase in the volumetric feed rate of the initial reaction mixture leads to a decrease of the yield of the target products, and reducing the speed to increase output of products.

The change in the ratio of catalyst components leads to a sharp decrease in its catalytic activity. The service life of the catalyst is 1000 hours

The invention is illustrated in the examples.

P R I m e R 1. To obtain the catalyst is thoroughly mixed with 52 g of vanadium oxide (V) THE 6-09-4093-88 containing the basic substance 51 g, 6 g of manganese oxide (II) THE 6-09-3217-78 and 43.9 g of iron oxide THAT 6-09-563-85 containing 43 g of the basic substance, the mixture is then melted at a temperature of not less than 880aboutWith, the melt is cooled, crushed and classified on the screens, selecting the fraction of the catalyst with a particle size of 1-2 mm, the Catalyst has a specific surface area of 0.5 m2/g and a bulk density equal to 1.82 g/cm3.

30 ml of the catalyst load in the laboratory setting - t is m

The reaction mixture of 1-naphthol:methanol in a molar ratio of 1:5 submit to the reactor through the evaporator with a bulk velocity 300 h-1. The reaction is carried out at 280aboutAnd atmospheric pressure. The products of methylation containing 26,65% methanol, 1,77% 1-naphthol, 61,42% 2-methyl-1-naphthol, 10,16% 2,4-dimethyl-1-naphthol, collect. Then distilled off unreacted methanol. Conversion of 1-naphthol is 97%. The yield of 2-methyl-1-naphthol 85%, 2,4-dimethyl-1-naphthol - 12%.

P R I m m e R 2. For the preparation of the catalyst are thoroughly mixed to 428.6 g of vanadium oxide (V) THE 6-09-4093-88 containing 420 g of the basic substance, 80 g of manganese oxide THAT 6-09-3217-78 and 510,2 g of iron oxide (III) THE 6-09-563-85 containing 500 g of the basic substance. The mixture is then melted at a temperature of not less than 880aboutWith, the melt is cooled, crushed and classified on the screens, selecting the fraction of the catalyst with a particle size of 2-3 .5 mm.

The catalyst has a specific surface area of 0.6 m2/g and a bulk density of at 1.91 g/cm3.

525 ml of catalyst was loaded into a pilot plant, a tubular flow type reactor made of stainless steel with external heating and internal tube diameter 27 mm

The reaction mixture of 1-naphthol:methanol in a molar, zootoxin is the t 2 kgf/see The products of methylation is collected and distilled off the excess methanol. Conversion of 1-naphthol is 100%. The yield of 2-methyl-1-naphthol 42%, 2,4-dimethyl-1-naphthol - 38%.

P R I m e R 3. To obtain the catalyst is thoroughly mixed with 52 g of vanadium oxide (V) THE 6-09-4093-88 containing 51 g of the basic substance, 6 g of manganese oxide (II), THE 6-09-3217-78, and 43.9 g of iron (III) oxide, THE 6-09-563-85 containing 43 g of the basic substance. The mixture is then melted at a temperature of not less than 880aboutWith, the melt is cooled, crushed and classified on the screens, selecting the fraction of the catalyst with a particle size of 1-2 mm, the Catalyst has a specific surface area of 0.7 m2/g, bulk density of 1.88 g/cm3.

Further methylation of 1-naphthol in methanol were analogously to example 1, the difference being that the reaction mixture of 1-naphthol:methanol was applied in a molar ratio of 1:8 with a bulk velocity of 400 h-1. The reaction was carried out at 330aboutC. Conversion of 1-naphthol was 100% , the yield of 2-methyl-1-naphthol 65%, 2,4-dimethyl-1-naphthol - 31%.

P R I m e R 4. To obtain the catalyst is thoroughly mixed 469,4 g of vanadium oxide, THE 6-09-4093-88 containing 460 g of the basic substance, 70 g of manganese oxide (II), THE 6-09-3217-78, and 479,6 g of iron oxide (III), THE 6-09-563-85 containing 470 g main VT on the screens, selecting the fraction of the catalyst particle size 2-3,5 mm Catalyst has a specific surface area of 0.5 m2/g and a bulk density of 2.00 g/cm3.

Further methylation of 1-naphthol in methanol were as in example 2, the difference lies in the fact that the reaction was carried out at 300aboutAnd atmospheric pressure. Conversion of 1-naphthol was 98,3% , the yield of 2-methyl-1-naphthol 81%, 2,4-dimethyl-1-naphthol 17%.

P R I m e R 5. Similar to example 2, the difference is that the methylation reaction of 1-naphthol with methanol was carried out at a temperature of 250aboutC, atmospheric pressure and the reaction mixture was applied with a bulk velocity of 100 h-1. The catalyst has a specific surface area of 0.6 m2/g and a bulk density of 1.92 g/cm3. The conversion of 1-naphthol was 70% , the yield of 2-methyl-1-naphthol 53%, 2,4-dimethyl-1-naphthol 17%.

The catalyst composition, its physical and catalytic properties, conditions of methylation of 1-naphthol in methanol are summarized in table.

Thus, this invention allows to obtain methylated 1-Naftali formula 4 - R-2-methyl-1-Naftali, where R = a) H (2-methyl-1-naphthol), b) CH3(2,4-dimethyl-1-naphthol) or their mixtures with a large 2.9 27.7% of the output in a more simple process conditions.

To obtain 2-methyl-1,4-naphthoquinone.

The simplification process is to reduce the reaction temperature and pressure, the exception under division and separation of methylated 1-Naftalan.

The METHOD of OBTAINING a MIXTURE of 2-METHYL-1-NAPHTHOL, 2,4-DIMETHYL-1-NAPHTHOL catalytic vapor-phase methylation of 1-naphthol in methanol at elevated temperature, a molar ratio of 1-naphthol : methanol 1 : (5 - 10) and the space velocity of the feedstock 100 - 1000 h-1, characterized in that, to increase the yield of the target products and simplify the process, the methylation reaction is carried out at 250 - 380oWith the use of a catalyst containing the oxides of vanadium (V), manganese (II) and iron (III) in the following ratio, wt.%:

The vanadium oxide - 42 - 51

Manganese oxide - 6 - 8

Iron oxide - Rest

 

Same patents:

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9 cl, 1 tbl, 12 ex

FIELD: chemistry.

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17 cl, 1 tbl, 16 ex, 17 dwg

FIELD: chemistry.

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27 cl, 8 tbl, 50 ex, 1 dwg

FIELD: chemistry.

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11 cl, 1 tbl, 4 ex

Oxidation catalyst // 2400298

FIELD: process engineering.

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2 ex, 1 tbl

FIELD: chemistry.

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5 cl, 3 tbl, 7 ex

FIELD: chemistry.

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7 cl, 17 ex, 1 tbl

FIELD: chemistry.

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EFFECT: use of present invention simplifies the processing method and increases isoprene output.

3 cl, 12 ex, 1 tbl

FIELD: chemistry.

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3 cl, 1 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to catalytic purification of exhaust gases of internal combustion engines. Claimed is composition for purification of exhaust gases of internal combustion engines based on cerium oxide, containing niobium oxide, with the following weight contents: niobium oxide from 2 to 20%, the remaining part - cerium oxide. Also claimed is composition with the following weight contents: cerium oxide at least 65%, niobium oxide from 2 to 12%, zirconium oxide to 48%. After calcinations for 4 hours at 800°C compositions have acidity at least 6·10-2, with said acidity being expressed in ml of ammonia per m2 of composition, with the surface, expressed in m2, used for determination of acidity, representing specific surface after calcinations for 4 hours at 800°C and specific surface at least 15 m2/g, and after calcinations for 4 hours at 1000°C it has specific surface at least 2 m2/g, in particular at least 3 m2/g. Invention relates to catalyst, which contains said compositions, to methods of oxidising CO and hydrocarbons, N2O, decomposition, for HOx and CO2 adsorption. Said compositions and catalyst are applied in reaction of gas with water, reaction of conversion with water steam, isomeration reaction, reaction of catalytic cracking and as triple action catalyst.

EFFECT: compositions possess satisfactory reducing ability in combination with good acidity, specific surface of which remains suitable for application in catalysis.

16 cl, 1 tbl, 14 ex

FIELD: chemistry.

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EFFECT: invention simplifies technology of producing catalyst, reduces damaging effect on the environment, reduces cost of catalyst.

3 cl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to catalytic cracking of hydrocarbons. Described is method of obtaining light olefins by catalytic cracking of hydrocarbons with 4 or more than 4 carbon atoms, with boiling point 30-200°C, in presence of catalyst, characterised by the fact that 0.01-5.0 wt % of MnO2 and 1-15 wt % of P2O5 are simultaneously added to catalyst components, where catalyst components contain 1-50 wt % of zeolite, 21-70 wt % of clay and 1-40 wt % of inorganic oxide and where both MnO2 and P2O5 are introduced into (modify) each of catalyst components, such as ZSM-5 zeolite, clay and inorganic oxide.

EFFECT: increase of product outcome.

10 cl, 1 dwg, 6 tbl, 9 ex

FIELD: oil and gas industry.

SUBSTANCE: invention relates to the catalyst, containing the hexaaluminate, in which there is the hexaaluminate containing phase, including cobalt in the amount from 2 up to 15 moll. % and at least one other element, selected from the group consisting of lanthanum, barium and strontium in the amount from 2 up to 25 moll. %, and the amount of aluminium is from 70 up to 90 moll. %. Besides the hexaaluminate containing phase in the catalyst, there is from 0 up to 50 wt % of the accessory oxide phase. The proposed catalyst production method contains according to the invention the aluminium source preparing, preferably alumina and/or aluminium hydroxide (boehmite), in the form of dispersible primary particles ≤with the size 500 nm; placing into contact of the fine aluminium source to the fusible or soluble cobalt containing compound, and at least one soluble or fused salt of the metal, selected from the group consisting the barium, lanthanum and strontium; careful mixing of the aluminium source with dissolved, or, respectively, molten metal salts; the mixture drying; the mixture low-temperature calcination; moulding, or respectively shaping. Besides, the invention relates to the gas reforming method, containing more than 70 vol. % of hydrocarbons, preferably methane and in the presence of carbon dioxide, with the hexaaluminate catalyst, which is heated at the contact with gas to be reformed at the temperature above 700°C, preferably above 800°C, more preferably above 900°C in the reactor, the pressure higher than 5 bar, preferably higher than 10 bar, more preferably above 15 bar, the space velocity of the reforming gas, placed into contact to the catalyst, is in the range from 500 to 20,000 h-1, and the catalyst containing hexaaluminate, contains the cobalt and at least one other metal, selected from the group, consisting of barium, strontium and lanthanum.

EFFECT: catalyst with the low lanthanum content, with high coking resistance and high catalytic activity, using over the long periods of time in extremely hard process conditions.

15 cl, 4 dwg, 6 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to the methods for producing oxide catalysts on a metal support substrate that can be used in oxidation reactions of CO to CO2, which take place in the high-temperature processes for cleaning process and exhaust gases, in particular in the energy and automotive industries. The proposed method includes anodizing an aluminium substrate in a galvanostatic mode at the current density of 10-15 mA/cm2 for 20-60 min in 3% aqueous solution of oxalic acid C2H2O4, washing and drying, after which the intermediate porous alumina layer formed on the aluminium substrate is treated with a 1% solution of phosphoric acid heated up to 35°C, washed, dried, and applied to the treated aluminium substrate, ultrafine manganese dioxide, which is formed by impregnation with a 5% solution of potassium permanganate KMnO4 followed by annealing in air at 220-230°C for 10 minutes, while the operation of applying manganese dioxide can be carried out three times.

EFFECT: simplification and cheaper technology while expanding the range of composite catalytic materials containing a metal substrate with supported transition metal oxides.

2 cl, 4 dwg, 2 ex

FIELD: chemistry.

SUBSTANCE: invention refers to a method for the one-stage production of (3-hydroxypropyl)naphthols of having a structure of R1=CH2CH2CH2OH, R2=OH, R3=H; R1=OH, R2=CH2CH2CH2OH, R3=H; R1=OH, R2=CH2CH2CH2OH, R3=CH2CH2CH2OH; R1=OH, R2=T-Bu, R3=CH2CH2CH2OH, effective biologically active substances of neutropic action. The method consists in conducting a reaction of α-, β-naphthols, their derivatives or their sodium salts with allyl alcohol and alkali at temperature 100-170°C. A purified product yield is 40-60%.

EFFECT: higher yield.

4 ex

FIELD: chemistry.

SUBSTANCE: application relates to a marking label for gasolines which represents hydroxyl-containing derivatives of aromatic series, wherein the hydroxyl group is connected directly to the aromatic ring, selected from a series of resorcinol, 4-hexylresorcinol or β-naphthol. The proposed label can be used in low concentrations.

EFFECT: absence of its influence on the performance characteristics of marked gasolines.

3 dwg, 4 ex

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