CN111995496B - Preparation method of isononanol - Google Patents
Preparation method of isononanol Download PDFInfo
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- CN111995496B CN111995496B CN202010481547.3A CN202010481547A CN111995496B CN 111995496 B CN111995496 B CN 111995496B CN 202010481547 A CN202010481547 A CN 202010481547A CN 111995496 B CN111995496 B CN 111995496B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
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- Y02P20/584—Recycling of catalysts
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Abstract
The invention discloses a preparation method of isononanol, which comprises the following steps: 1) Isooctene and formaldehyde are used as raw materials, and Isononyl alcohol is generated through Prins reaction under the catalysis of an acid catalyst; 2) Hydrogenating the isononyl alcohol obtained in the step 1) in the presence of a hydrogenation catalyst to obtain isononyl alcohol; wherein, when the Prins reaction is carried out in the step 1), the reaction conditions are as follows: the temperature is 160-250 ℃, the reaction pressure is 5.0-10.0MPa, the stirring speed is 100-400 rpm, and the reaction time is 1-5h; the isononanol hydrogenation reaction conditions of the step 2) are as follows: hydrogen oil volume ratio 300:1-1000:1, the reaction temperature is 50-120 ℃, the reaction pressure is 2.0-6.0MPa, and the reaction space velocity is 0.2-1.0h ‑1 . The preparation method of isononanol provided by the invention has the advantages of mild reaction conditions, smaller reaction heat, low catalyst price, no corrosion to equipment, environmental friendliness, insolubility in organic matters, recycling through simple filtration, simple equipment, convenient operation and lower investment cost.
Description
Technical Field
The invention relates to a preparation method of an alcohol compound, in particular to a preparation method of isononanol.
Background
Isononanol (3, 5-trimethyl-1-hexanol) is an important chemical intermediate, and its downstream products can be used in perfumery, medicine, high-end lubricating oil, plasticizers and the like. At present, isononanol in China almost needs to be imported, and the production of the global isononanol is controlled in a few manufacturers including Exxon Mobil, oxeno, BASF, kyowa Yuka in Japan, taiwan south Asia plastics company and other few enterprises.
Isononol is produced through the hydroformylation of isooctene and synthesis gas, and through aldehyde hydrogenation to produce isononanol, there are mainly German basf process, exxon Mobil chemical company process, oxeno process, johnson Matthey process, etc.
Chinese patent CN1186060a describes a process for the preparation of alcohols of 7-18 carbon atoms by hydroformylation of olefins with synthesis gas at a temperature of 50-220 ℃ and a pressure of 100-400 bar using a cobalt-containing catalyst to produce aldehydes which are then hydrogenated to produce alcohols. CN101903318B describes a single stage continuous process for the hydroformylation of higher olefins or mixtures of olefins, which process has the advantage that the formation of the cobalt carbonyl complex catalyst, the extraction and the hydroformylation of olefins are carried out in one reactor. CN101497553a specifically describes a method for preparing C9 alcohol from C8 olefin, which uses cobalt-based catalyst, and uses the hydroformylation reaction of C8 olefin and synthesis gas to prepare alcohol by hydrogenation, and is mainly characterized by using two-stage hydroformylation reactor, and for better reaction effect, using one nozzle or several mixed nozzles to spray the olefin, synthesis gas and cobalt salt aqueous solution of catalyst into the reactor.
The catalyst for preparing isononyl aldehyde by hydroformylation of isooctene is mainly cobalt carbonyl complex or rhodium phosphine complex, the catalyst is complex to manufacture, and meanwhile, the cobalt carbonyl complex is easy to decompose, and the reaction is required to be carried out under higher pressure in order to keep the activity of the catalyst. The rhodium-based catalyst has higher cost and lower hydroformylation reaction activity for high-carbon number isoolefin. The hydroformylation reaction liquid usually has a step of removing the catalyst, and an acidic cobalt salt aqueous solvent is generally adopted to oxidize and remove the cobalt-based catalyst at a certain temperature, so that the problem of equipment corrosion exists. The formylation reaction is a strongly exothermic reaction requiring the addition of an inert solvent or the addition of a heat exchanger to the reactor to maintain the exotherm. Therefore, the production equipment is complex, the operation is very complicated, the investment is huge, and the small and medium enterprises are difficult to bear.
It can be seen that there is a need for an improvement in at least one of the above-mentioned problems with the prior art.
Disclosure of Invention
In view of the above problems of the prior art, an aspect of the present invention is to provide a process for producing isononanol which is mild in reaction conditions and is not corroded by equipment.
In order to achieve the above object, the present invention provides a method for preparing isononanol, comprising:
1) Isooctene and formaldehyde are used as raw materials, and Isononyl alcohol is generated through Prins reaction under the catalysis of an acid catalyst;
2) Hydrogenating the isononyl alcohol obtained in the step 1) in the presence of a hydrogenation catalyst to obtain isononyl alcohol;
wherein, when the Prins reaction is carried out in the step 1), the reaction conditions are as follows: the temperature is 160-250 ℃, the reaction pressure is 5.0-10.0MPa, the stirring speed is 100-400 rpm, and the reaction time is 1-5h; the isononanol hydrogenation reaction conditions of the step 2) are as follows: hydrogen oil volume ratio 300:1-1000:1, the reaction temperature is 50-120 ℃, the reaction pressure is 2.0-6.0MPa, and the reaction space velocity is 0.2-1.0h -1 。
Preferably, the isooctene is 2, 4-trimethyl-1-pentene or a mixture containing 2, 4-trimethyl-1-pentene, and the formaldehyde is one or more of formaldehyde aqueous solution, formaldehyde methanol solution, paraformaldehyde or trioxymethylene.
Preferably, in the Prins reaction in step 1), the molar ratio of enal is 4:1-20:1.
preferably, the reaction in the step 1) is carried out in a high-pressure reaction kettle, wherein the mass ratio of the acid catalyst to formaldehyde is 1:100-5:100, inert gas is filled for protection, the reaction product is filtered to remove the acid catalyst, the acid catalyst enters a rectifying tower to separate unreacted isooctene to obtain isononyl enol, the isooctene returns to a first reaction section for recycling, and the isononyl enol enters the step 2).
Preferably, the inert gas is one or more of nitrogen, argon or helium.
Preferably, the acidic catalyst is one or more of acidic molecular sieve, lewis acid or phosphoric acid salt.
Preferably, the acidic molecular sieve is hydrogen beta molecular sieve, mordenite or MCM-22; the Lewis acid is one of aluminum trichloride, ferric trichloride, copper chloride, zinc chloride or stannic chloride; the phosphoric acid salt is one of potassium dihydrogen phosphate, dipotassium hydrogen phosphate, sodium dihydrogen phosphate or disodium hydrogen phosphate.
Preferably, the hydrogenation catalyst comprises one or a mixture of several of nickel, copper, platinum or palladium.
Compared with the prior art, the preparation method of isononanol provided by the invention adopts isooctene and formaldehyde as raw materials, isononanol is prepared through Prins reaction, isononanol is prepared through hydrogenation, the reaction condition is mild, the reaction heat is smaller, the catalyst is low in price, equipment is not corroded, the method is environment-friendly, the method is insoluble in organic matters, and the method can be recycled through simple filtration, and is simple in equipment, convenient to operate and low in investment cost.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the disclosure.
This document provides an overview of various implementations or examples of the technology described in this disclosure, and is not a comprehensive disclosure of the full scope or all of the features of the disclosed technology.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present disclosure more apparent, the technical solutions of the embodiments of the present disclosure will be clearly and completely described below with reference to the accompanying drawings of the embodiments of the present disclosure. It will be apparent that the described embodiments are some, but not all, of the embodiments of the present disclosure. All other embodiments, which can be made by one of ordinary skill in the art without the need for inventive faculty, are within the scope of the present disclosure, based on the described embodiments of the present disclosure.
In order to keep the following description of the embodiments of the present disclosure clear and concise, the present disclosure omits detailed description of known functions and known components.
The preparation method of isononanol provided by the embodiment of the invention comprises the following steps: 1) Isooctene and formaldehyde are used as raw materials, and Isononyl alcohol is generated through Prins reaction under the catalysis of an acid catalyst; 2) Hydrogenating the isononyl alcohol obtained in the step 1) in the presence of a hydrogenation catalyst to obtain isononyl alcohol; wherein, when the Prins reaction is carried out in the step 1), the reaction conditions are as follows: the temperature is 160-250 ℃, the reaction pressure is 5.0-10.0MPa, the stirring speed is 100-400 rpm, and the reaction time is 1-5h; the isononanol hydrogenation reaction conditions of the step 2) are as follows: hydrogen oil volume ratio 300:1-1000:1, the reaction temperature is 50-120 ℃, the reaction pressure is 2.0-6.0MPa, and the reaction space velocity is 0.2-1.0h -1 。
In this example, the process is split into two reaction stages, the first stage starting from isooctene and formaldehyde, wherein preferably the isooctene is 2, 4-trimethyl-1-pentene or a mixture comprising 2, 4-trimethyl-1-pentene; preferably, the formaldehyde is one or more of aqueous formaldehyde solution, methanolic formaldehyde solution, paraformaldehyde or trioxymethylene. In the first stage reaction, two raw materials react under the action of an acid catalyst through Prins to generate isononyl alcohol; the second stage uses isononanol to produce isononanol through catalytic hydrogenation.
The first stage reaction is carried out in a high-pressure reaction kettle, specifically, isooctene, formaldehyde and an acid catalyst are put into the reaction kettle together, wherein the molar ratio of olefine to aldehyde is 4:1-20:1, the mass ratio of the catalyst to formaldehyde is 1:100-5, inert gas is filled for protection, the reaction temperature is 160-250 ℃, the reaction pressure is 5.0-10.0MPa, the stirring speed is 100-400 r/min, and the reaction time is 1-5h. The reaction product is filtered to remove the catalyst, and the catalyst enters a rectifying tower to separate unreacted isooctene to obtain isononyl enol, the isooctene returns to the first reaction section for recycling, and isononyl enol enters the second reaction section. In this stage, the inert gas is one of nitrogen, argon or helium; the acid catalyst is one of an acid molecular sieve, lewis acid or phosphoric acid salt, wherein the acid molecular sieve is one of hydrogen beta molecular sieve, mordenite and MCM-22, the Lewis acid is one of aluminum trichloride, ferric trichloride, copper chloride, zinc chloride or stannic chloride, and the phosphoric acid salt is one of potassium dihydrogen phosphate, dipotassium hydrogen phosphate, sodium dihydrogen phosphate or disodium hydrogen phosphate;
the second stage of reaction is carried out in a fixed bed continuous reaction, and the reactor device hydrogenates the catalyst. The isononanenol in the first reaction section is mixed with hydrogen and then enters a reactor, and the volume ratio of hydrogen to oil is 300:1-1000:1, the reaction temperature is 50-120 ℃, the reaction pressure is 2.0-6.0MPa, and the reaction space velocity is 0.2-1.0h -1 The hydrogenation product is separated by a rectifying tower, and the isononanol with high purity is obtained. The hydrogenation catalyst is one or a mixture of several of nickel, copper, platinum or palladium as main active substances.
Specific examples are provided below to illustrate the invention.
Example 1
300g of isooctene, 8g of paraformaldehyde and 1g of sodium dihydrogen phosphate are added into an autoclave, wherein the molar ratio of olefine to aldehyde is=10:1; after the kettle is closed, checking the air tightness, confirming no air leakage, replacing air in the kettle with nitrogen for five times, then introducing nitrogen for pressurizing, stirring at 170 r/min, heating to 200 ℃, wherein the pressure is 7.0MPa, and reacting for 4 hours; after the reaction is finished, cooling to room temperature, decompressing, opening the kettle, taking out the reaction liquid, filtering, taking the solid as a catalyst, and recycling; the rest reaction liquid is subjected to chromatographic analysis, and contains 87.5% of unreacted isooctene, 11.9% of isononanol and 0.6% of other components.
Example 2
300g of isooctene, 40g of 40% aqueous formaldehyde solution and 1g H beta molecular sieve are charged into an autoclave, wherein the molar ratio of isoolefine aldehyde=5:1; after the kettle is closed, checking the air tightness, confirming no air leakage, replacing air in the kettle with nitrogen for five times, then introducing nitrogen for pressurizing, stirring at 320 r/min, heating to 230 ℃, wherein the pressure is 9.0MPa, and reacting for 2 hours; after the reaction is finished, cooling to room temperature, decompressing, opening the kettle, taking out the reaction liquid, filtering, taking the solid as a catalyst, and recycling; the rest reaction liquid is separated by a separating funnel, and the upper oil phase is subjected to chromatographic analysis and contains 75.5% of unreacted isooctene, 22.3% of isononanol and 2.2% of other components.
Example 3
300g of isooctene, 6g of trioxymethylene and 1g of zinc chloride are added into a high-pressure reaction kettle, wherein the molar ratio of enal is 13.4:1; after the kettle is closed, checking the air tightness, confirming no air leakage, replacing air in the kettle with nitrogen for five times, then introducing nitrogen for pressurizing, stirring at the speed of 250 revolutions per minute, heating to 180 ℃, and reacting for 5 hours at the pressure of 6.0 MPa; after the reaction is finished, cooling to room temperature, decompressing, opening the kettle, taking out the reaction liquid, filtering, taking the solid as a catalyst, and recycling; the rest reaction liquid is subjected to chromatographic analysis, and contains 90.8% of unreacted isooctene, 8.9% of isononyl alcohol and 0.3% of other components.
Example 4
300g of isooctene, 22g of formaldehyde-methanol mixture with 45% formaldehyde content and 1g of dipotassium hydrogen phosphate are added into a high-pressure reaction kettle, wherein the molar ratio of olefine aldehyde is=8.1:1; after the kettle is closed, checking the air tightness, confirming no air leakage, replacing air in the kettle with nitrogen for five times, then introducing nitrogen for pressurizing, stirring at 390 r/min, heating to 250 ℃, wherein the pressure is 10.0MPa, and reacting for 1 hour; after the reaction is finished, cooling to room temperature, decompressing, opening the kettle, taking out the reaction liquid, filtering, taking the solid as a catalyst, and recycling; the rest reaction liquid is subjected to chromatographic analysis, and contains 80.3% of unreacted isooctene, 13.7% of isononanol, 3.6% of methanol and 3.1% of other components.
Example 5
Filling 10ml of Raney nickel catalyst on the fixed bed micro reactor; the reaction solution in the example 1 is subjected to rectification separation to obtain 36g of isononanol as a raw material, and the raw material is mixed with hydrogen and then enters a reactor; hydrogen oil volume ratio 500:1, the reaction temperature is 100 ℃, the reaction pressure is 3.0MPa, and the reaction space velocity is 0.5h < -1 >; the reaction solution was analyzed by chromatography and contained 99.2% isononanol, 0.5% isononane and 0.3% of other components.
Example 6
10ml of copper catalyst was packed on a fixed bed microreactor; the reaction solution in the example 2 is rectified and separated to obtain 70g of isononanol as a raw material, and the isononanol is mixed with hydrogen and then enters a reactor; hydrogen oil volume ratio 900:1, the reaction temperature is 120 ℃, the reaction pressure is 5.0MPa, and the reaction space velocity is 0.2h < -1 >; the reaction solution was analyzed by chromatography and contained 98.4% isononanol, 1.0% isononane and 0.6% of other components.
Example 7
10ml of platinum catalyst is filled on the fixed bed micro reactor; the reaction solution in the example 4 is subjected to rectification separation to obtain 44g of isononanol as a raw material, and the 44g of isononanol is mixed with hydrogen and enters a reactor; hydrogen oil volume ratio 300:1, the reaction temperature is 60 ℃, the reaction pressure is 2.0MPa, and the reaction space velocity is 0.8h < -1 >; the reaction solution was analyzed by chromatography and contained 99.5% isononanol, 0.1% isononane and 0.4% of other components.
The above embodiments are only exemplary embodiments of the present invention and are not intended to limit the present invention, the scope of which is defined by the claims. Various modifications and equivalent arrangements of this invention will occur to those skilled in the art, and are intended to be within the spirit and scope of the invention.
Claims (7)
1. A process for the preparation of isononanol comprising:
1) Isooctene and formaldehyde are used as raw materials, and Isononyl alcohol is generated through Prins reaction under the catalysis of an acid catalyst;
2) Hydrogenating the isononyl alcohol obtained in the step 1) in the presence of a hydrogenation catalyst to obtain isononyl alcohol;
wherein, when the Prins reaction is carried out in the step 1), the reaction conditions are as follows: the temperature is 160-250 ℃, the reaction pressure is 5.0-10.0MPa, the stirring speed is 100-400 rpm, and the reaction time is 1-5h; the isononanol hydrogenation reaction conditions of the step 2) are as follows: hydrogen oil volume ratio 300:1-1000:1, the reaction temperature is 50-120 ℃, the reaction pressure is 2.0-6.0MPa, and the reaction space velocity is 0.2-1.0h -1 The isooctene is 2, 4-trimethyl-1-pentene or a mixture containing 2, 4-trimethyl-1-pentene, and the formaldehyde is one or more of formaldehyde aqueous solution, formaldehyde methanol solution, paraformaldehyde or trioxymethylene.
2. The process for producing isononanol according to claim 1, wherein the molar ratio of enal is 4 when the Prins reaction is carried out in step 1): 1-20:1.
3. the preparation method of isononanol according to claim 1, wherein the reaction in the step 1) is carried out in a high-pressure reaction kettle, wherein the mass ratio of the acid catalyst to formaldehyde is 1:100-5:100, inert gas is filled for protection, the reaction product is filtered to remove the acid catalyst, unreacted isooctene is separated in a rectifying tower to obtain isononyl enol, the isooctene is returned to the first reaction section for recycling, and the isononyl enol is fed into the step 2).
4. A process for the preparation of isononanol according to claim 3, wherein the inert gas is one or more of nitrogen, argon or helium.
5. The process for producing isononanol according to claim 1, wherein the acidic catalyst is one or more of acidic molecular sieve, lewis acid or phosphoric acid salt.
6. The process for preparing isononanol according to claim 5, wherein the acidic molecular sieve is hydrogen beta molecular sieve, mordenite or MCM-22; the Lewis acid is one of aluminum trichloride, ferric trichloride, copper chloride, zinc chloride or stannic chloride; the phosphoric acid salt is one of potassium dihydrogen phosphate, dipotassium hydrogen phosphate, sodium dihydrogen phosphate or disodium hydrogen phosphate.
7. The process for producing isononanol according to claim 1, wherein the hydrogenation catalyst comprises one or a mixture of several of nickel, copper, platinum or palladium.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1681756A (en) * | 2002-09-17 | 2005-10-12 | 约翰森·马瑟公开有限公司 | Process for production of an alcohol |
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| CN1681756A (en) * | 2002-09-17 | 2005-10-12 | 约翰森·马瑟公开有限公司 | Process for production of an alcohol |
Non-Patent Citations (2)
| Title |
|---|
| Molecular behaviors of formaldehyde encapsulated in supercages of zeolite NaY with different loadings and its intrinsic reactivity for the carbonyl-ene reaction with α-methylstyrene;Sato, Kei-ichi等;《Bulletin of the Chemical Society of Japan》;20171231;第90卷(第12期);1318-1324 * |
| Product Subclass 7:Alkenylsodium Compounds;A. Mordini等;《Science of Synthesis》;20061231;1205-1208 * |
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