CN112062792A - Production method of tris (dimethylamine) cyclopentadiene hafnium - Google Patents

Production method of tris (dimethylamine) cyclopentadiene hafnium Download PDF

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CN112062792A
CN112062792A CN202010775113.4A CN202010775113A CN112062792A CN 112062792 A CN112062792 A CN 112062792A CN 202010775113 A CN202010775113 A CN 202010775113A CN 112062792 A CN112062792 A CN 112062792A
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hafnium
dimethylamino
cyclopentane
dimethylamine
reaction
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曹季
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Core Yuexin Nanjing Electronic Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00—Metallocenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
    • C07C1/30—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms by splitting-off the elements of hydrogen halide from a single molecule
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • 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
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

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Abstract

The invention relates to the technical field of compound production, and discloses a method for producing tris (dimethylamine) cyclopentadiene hafnium, which comprises the following steps: s1: adding raw materials, and adding 20-60 parts of hafnium tetrachloride into a flask under the protection of inert atmosphere; 1000-1800 parts of ionic liquid buffer solvent and 100-300 parts of dimethylamino lithium salt; s2: heating and stirring, heating during reaction, and then stirring intermittently; s3: and (3) purifying, namely adding activated carbon particles into the solution after reaction, fully stirring by using a glass rod after the activated carbon particles are added, standing for 10-30 minutes, filtering, and collecting filtrate to obtain high-precision tetrakis (dimethylamino) hafnium. The invention can reduce the reaction heat release, avoid the generation of byproducts, improve the yield of the tetra (dimethylamino) hafnium, and carry out distillation purification after the reaction generates the tri (dimethylamino) cyclopentadienyl hafnium, thereby improving the purity of the product.

Description

Production method of tris (dimethylamine) cyclopentadiene hafnium
Technical Field
The invention relates to the technical field of compound production, in particular to a method for producing tris (dimethylamine) cyclopentadiene hafnium.
Background
The tris (dimethylamino) cyclopentadienyl hafnium is liquid at normal temperature, is a compound very sensitive to air and water vapor, can be dissolved in organic solvents such as hydrocarbons, carbon tetrachloride and the like, has better stability and higher vapor pressure, and shows quite high reactivity, so the physicochemical characteristics of the tris (dimethylamino) cyclopentadienyl hafnium can be used for preparing hafnium oxide films by CVD or ALD technology.
In many syntheses, generally, the cyclopentadienyl group introduced into an intermediate needs two steps, wherein the first step is to synthesize sodium cyclopentadienyl, and the second step is to react with the intermediate to finally obtain a target product, but the purity of the tris (dimethylamine) cyclopentadienyl hafnium synthesized by the method is not high, and the purity cannot meet the requirements of people.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides a method for producing tris (dimethylamine) cyclopentadiene hafnium, which mainly solves the problems that the purity of the tris (dimethylamine) cyclopentadiene hafnium synthesized by the prior method is not high and can not meet the requirements of people.
(II) technical scheme
In order to achieve the purpose, the invention provides the following technical scheme:
the production method of the tri (dimethylamine) cyclopentadiene hafnium comprises the following steps:
s1: adding raw materials, and adding 20-60 parts of hafnium tetrachloride into a flask under the protection of inert atmosphere; 1000-1800 parts of ionic liquid buffer solvent and 100-300 parts of dimethylamino lithium salt;
s2: heating and stirring, heating during reaction, and then stirring intermittently;
s3: purifying, adding activated carbon particles into the solution after reaction, fully stirring by using a glass rod after the activated carbon particles are added, standing for 10-30 minutes, filtering, and collecting filtrate to obtain high-precision tetrakis (dimethylamino) hafnium;
s4: preparing monobromo cyclopentane, selecting cyclopentane, and reacting the cyclopentane with bromine under illumination to obtain monobromo cyclopentane;
s5: preparing cyclopentadiene, heating monobromo cyclopentane in an alcohol solution of sodium hydroxide to react to obtain cyclopentene, reacting with a carbon tetrachloride solution of bromine to obtain o-dibromo cyclopentane, and heating to remove the o-dibromo cyclopentane to obtain cyclopentadiene;
s6: adding cyclopentadiene dropwise into tetrakis (dimethylamino) hafnium to react to generate tris (dimethylamino) cyclopentadienyl hafnium, and then distilling and purifying.
Further, in the S1, the inert gas is one of argon gas and helium gas, the ionic buffer solution is anhydrous diethyl ether, 4,4' -diaminodiphenyl sulfide, tetramethylguanidine lactate, polyoxyethylene 20 oleyl ether, perfluoropolyether oil, 3-acetyl-2-fluorophenylboronic acid and ethylene.
On the basis of the scheme, the heating temperature in the S2 is controlled to be 10-29 ℃, the stirring time interval is 10-30 minutes, and the primary product is prepared by stirring for 8-15 times.
As a further scheme of the invention, the activated carbon particles in S3 are granular objects which are baked at 150-170 ℃ for 180-300 minutes for activation, and the mass ratio of the activated carbon particles to the mass ratio of the solution to be purified after reaction is 1-4: 5-10.
Further, the irradiation of light is performed for 20 to 60 minutes in the step S4, and the reaction temperature is controlled to be 10 to 50 ℃.
On the basis of the scheme, the heating temperature in the S5 is between 20 and 80 ℃ when cyclopentene is prepared, and the temperature is between 30 and 60 ℃ when cyclopentadiene is obtained by heating.
In a still further scheme of the invention, the molar ratio of the lithium salt of dimethylamino to the hafnium tetrachloride in S1 is 0.5-2: 0.2-3.
Further, the alcoholic solution of monobromocyclopentane and sodium hydroxide in S5 is used in a molar ratio of 0.5-2:5-10, and diluted with ethylbenzene when subjected to distillation in S6.
(III) advantageous effects
Compared with the prior art, the invention provides a method for producing the tris (dimethylamine) cyclopentadiene hafnium, which has the following beneficial effects:
1. by adding the ionic liquid buffer solvent, the exothermic reaction can be reduced, the generation of byproducts can be avoided, and the yield of the tetra (dimethylamino) hafnium can be improved.
2. In S4, sufficient reaction is carried out for 20-60 minutes of illumination, and the preparation effect of the monobromocyclopentane can be improved by carrying out sufficient illumination.
3. Adding activated carbon particles into the solution after reaction, and adsorbing impurities by the activated carbon particles after high-temperature activation to obtain high-precision tetrakis (dimethylamino) hafnium, thereby conveniently preparing the higher-precision tris (dimethylamino) cyclopentadienyl hafnium.
4. After the reaction generates the tris (dimethylamino) cyclopentadienyl hafnium, the tris (dimethylamino) cyclopentadienyl hafnium is distilled and purified, thereby improving the purity of the tris (dimethylamino) cyclopentadienyl hafnium.
Drawings
FIG. 1 is a schematic flow chart of a method for producing tris (dimethylamine) cyclopentadienyl hafnium according to the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Referring to fig. 1, a method for producing tris (dimethylamine) cyclopentadienylhafnium, comprising the steps of:
s1: adding raw materials, and adding 20-60 parts of hafnium tetrachloride into a flask under the protection of inert atmosphere; 1000-1800 parts of ionic liquid buffer solvent, which is convenient for the reaction of objects, and 100-300 parts of dimethylamino lithium salt;
s2: heating and stirring, heating during reaction, and then stirring intermittently;
s3: purifying, adding activated carbon particles into the solution after reaction, fully stirring by using a glass rod after the activated carbon particles are added, standing for 10-30 minutes, filtering, and collecting filtrate to obtain high-precision tetrakis (dimethylamino) hafnium;
s4: preparing monobromo cyclopentane, selecting cyclopentane, and reacting the cyclopentane with bromine under illumination to obtain monobromo cyclopentane;
s5: preparing cyclopentadiene, heating monobromo cyclopentane in an alcohol solution of sodium hydroxide to react to obtain cyclopentene, reacting with a carbon tetrachloride solution of bromine to obtain o-dibromo cyclopentane, and heating to remove the o-dibromo cyclopentane to obtain cyclopentadiene;
s6: adding cyclopentadiene dropwise into tetra (dimethylamino) hafnium to react to generate tri (dimethylamino) cyclopentadienyl hafnium, and then carrying out distillation purification to improve the purity of the product.
The inert gas in S1 is one of argon and helium, the ionic buffer solution is anhydrous ether, 4,4' -diaminodiphenyl sulfide, tetramethylguanidine lactate, polyoxyethylene 20 oleyl ether, perfluoropolyether oil, 3-acetyl-2-fluorophenylboric acid and ethylene are mixed, the reaction heat release can be reduced, the generation of byproducts is avoided, the yield of tetrakis (dimethylamino) hafnium is improved, the heating temperature in S2 is controlled at 10-29 ℃, the stirring time is 10-30 minutes apart, the stirring is carried out for 8-15 times in total, a primary product is prepared, the activated carbon particles in S3 are granular objects which are baked at 150-170 ℃ for 180-300 minutes for activation, the mass ratio of the activated carbon particles to the solution to be purified after the reaction is 1-4:5-10, and the activated carbon particles after high-temperature activation can adsorb impurities, highly accurate tetrakis (dimethylamino) hafnium is obtained.
In particular, the preparation effect of monobromocyclopentane can be improved by carrying out sufficient reaction and sufficient light irradiation after carrying out light irradiation for 20 to 60 minutes in S4, the reaction temperature is controlled to be 10 to 50 ℃, the heating temperature is 20 to 80 ℃ when cyclopentene is prepared in S5, the temperature is 30 to 60 ℃ when cyclopentadiene is obtained by heating, the molar ratio of the lithium salt of dimethylamino to the hafnium tetrachloride in S1 is 0.5 to 2:0.2 to 3, the molar ratio of the alcoholic solution of monobromocyclopentane and sodium hydroxide in S5 is 0.5 to 2:5 to 10, and the distillation effect can be improved by diluting with ethylbenzene in advance when distilling in S6.
Example 2
Referring to fig. 1, a method for producing tris (dimethylamine) cyclopentadienylhafnium, comprising the steps of:
s1: adding raw materials, and adding 20-60 parts of hafnium tetrachloride into a flask under the protection of inert atmosphere; 1000-1800 parts of ionic liquid buffer solvent, which is convenient for the reaction of objects, and 100-300 parts of dimethylamino lithium salt;
s2: heating and stirring, heating during reaction, and then stirring intermittently;
s3: purifying, adding activated carbon particles into the solution after reaction, fully stirring by using a glass rod after the activated carbon particles are added, standing for 10-30 minutes, filtering, and collecting filtrate to obtain high-precision tetrakis (dimethylamino) hafnium;
s4: preparing monobromo cyclopentane, selecting cyclopentane, and reacting the cyclopentane with bromine under illumination to obtain monobromo cyclopentane;
s5: preparing cyclopentadiene, heating monobromo cyclopentane in an alcohol solution of sodium hydroxide to react to obtain cyclopentene, reacting with a carbon tetrachloride solution of bromine to obtain o-dibromo cyclopentane, and heating to remove the o-dibromo cyclopentane to obtain cyclopentadiene;
s6: adding cyclopentadiene dropwise into tetra (dimethylamino) hafnium to react to generate tri (dimethylamino) cyclopentadienyl hafnium, and then carrying out distillation purification to improve the purity of the product.
The inert gas in S1 is one of argon and helium, the ionic buffer solution is anhydrous ether, 4,4' -diaminodiphenyl sulfide, tetramethylguanidine lactate, polyoxyethylene 20 oleyl ether, perfluoropolyether oil, 3-acetyl-2-fluorophenylboric acid and ethylene are mixed, the heating temperature in S2 is controlled at 15-29 ℃, the stirring time interval is 10-20 minutes, the stirring is carried out for 6-12 times, a primary product is prepared, active carbon particles in S3 are granular objects which are baked at 150-170 ℃ for 180-300 minutes for activation, the mass ratio of the active carbon particles to a solution needing to be purified after reaction is 1-3:6-10, and the active carbon particles activated at high temperature can adsorb impurities to obtain high-precision tetra (dimethylamino) hafnium.
In particular, the preparation effect of monobromocyclopentane can be improved by carrying out sufficient reaction and sufficient light irradiation in S4 for 20-60 minutes, the reaction temperature is controlled to be 10-40 ℃, the heating temperature in S5 is 20-76 ℃ when cyclopentene is prepared, the heating temperature in S5 is 30-60 ℃ when cyclopentadiene is obtained, the molar ratio of the lithium salt of dimethylamino to the hafnium tetrachloride in S1 is 0.5-2:0.2-4, the molar ratio of the alcoholic solution of monobromocyclopentane and sodium hydroxide in S5 is 0.5-2:5-10, and the distillation effect can be improved by diluting with ethylbenzene in advance when distilling in S6.
Example 3
Referring to fig. 1, a method for producing tris (dimethylamine) cyclopentadienylhafnium, comprising the steps of:
s1: adding raw materials, and adding 20-60 parts of hafnium tetrachloride into a flask under the protection of inert atmosphere; 1000-1800 parts of ionic liquid buffer solvent, which is convenient for the reaction of objects, and 100-300 parts of dimethylamino lithium salt;
s2: heating and stirring, heating during reaction, and then stirring intermittently;
s3: purifying, distilling the solution after reaction under reduced pressure, and collecting fraction at 76-79 ℃/5-9 mmHg;
s4: preparing monobromo cyclopentane, selecting cyclopentane, and reacting the cyclopentane with bromine under illumination to obtain monobromo cyclopentane;
s5: preparing cyclopentadiene, heating monobromo cyclopentane in an alcohol solution of sodium hydroxide to react to obtain cyclopentene, reacting with a carbon tetrachloride solution of bromine to obtain o-dibromo cyclopentane, and heating to remove the o-dibromo cyclopentane to obtain cyclopentadiene;
s6: dripping cyclopentadiene into tetra (dimethylamino) hafnium to react to generate tri (dimethylamino) cyclopentadienyl hafnium, and then carrying out distillation purification to improve the purity of the product;
according to the invention, the inert gas in S1 is one of argon and helium, the ionic buffer solution is anhydrous ether, 4,4' -diaminodiphenyl sulfide, tetramethylguanidine lactate, polyoxyethylene 20 oleyl ether, perfluoropolyether oil, 3-acetyl-2-fluorophenylboric acid and ethylene are mixed, the reaction heat release can be reduced, the generation of byproducts is avoided, the yield of tetrakis (dimethylamino) hafnium is improved, the heating temperature in S2 is controlled at 10-29 ℃, the stirring time is 10-30 minutes apart, and the stirring is carried out for 8-15 times in total, so that the primary product is prepared.
In particular, the preparation effect of monobromocyclopentane can be improved by carrying out sufficient reaction and sufficient light irradiation after carrying out light irradiation for 20 to 60 minutes in S4, the reaction temperature is controlled to be 10 to 50 ℃, the heating temperature is 20 to 80 ℃ when cyclopentene is prepared in S5, the temperature is 30 to 60 ℃ when cyclopentadiene is obtained by heating, the molar ratio of the lithium salt of dimethylamino to the hafnium tetrachloride in S1 is 0.5 to 2:0.2 to 3, the molar ratio of the alcoholic solution of monobromocyclopentane and sodium hydroxide in S5 is 0.5 to 2:5 to 10, and the distillation effect can be improved by diluting with ethylbenzene in advance when distilling in S6.
In the description herein, it is noted that relational terms such as first and second, and the like, are used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.

Claims (8)

1. The production method of the tris (dimethylamine) cyclopentadiene hafnium is characterized by comprising the following steps of:
s1: adding raw materials, and adding 20-60 parts of hafnium tetrachloride into a flask under the protection of inert atmosphere; 1000-1800 parts of ionic liquid buffer solvent and 100-300 parts of dimethylamino lithium salt;
s2: heating and stirring, heating during reaction, and then stirring intermittently;
s3: purifying, adding activated carbon particles into the solution after reaction, fully stirring by using a glass rod after the activated carbon particles are added, standing for 10-30 minutes, filtering, and collecting filtrate to obtain high-precision tetrakis (dimethylamino) hafnium;
s4: preparing monobromo cyclopentane, selecting cyclopentane, and reacting the cyclopentane with bromine under illumination to obtain monobromo cyclopentane;
s5: preparing cyclopentadiene, heating monobromo cyclopentane in an alcohol solution of sodium hydroxide to react to obtain cyclopentene, reacting with a carbon tetrachloride solution of bromine to obtain o-dibromo cyclopentane, and heating to remove the o-dibromo cyclopentane to obtain cyclopentadiene;
s6: adding cyclopentadiene dropwise into tetrakis (dimethylamino) hafnium to react to generate tris (dimethylamino) cyclopentadienyl hafnium, and then distilling and purifying.
2. The method of claim 1, wherein the inert gas in S1 is one of argon and helium, and the ionic buffer is dehydrated ether, 4,4' -diaminodiphenyl sulfide, tetramethylguanidine lactate, polyoxyethylene 20 oleyl ether, perfluoropolyether oil, 3-acetyl-2-fluorophenylboronic acid, and ethylene.
3. A method for producing tris (dimethylamine) cyclopentadienylhafnium according to claim 1, wherein the heating temperature in S2 is controlled to 10 to 29 degrees, and the primary product is prepared by stirring 8 to 15 times in total at intervals of 10 to 30 minutes.
4. A method for producing tris (dimethylamine) cyclopentadienylhafnium according to claim 3, wherein the activated carbon particles in S3 are granular objects which are baked at 150-170 ℃ for 180-300 minutes to be activated, and the mass ratio of the activated carbon particles to the solution to be purified after the reaction is 1-4: 5-10.
5. A method of producing tris (dimethylamine) cyclopentadienylhafnium according to claim 1, wherein the S4 is irradiated with light for 20 to 60 minutes to allow sufficient reaction, and the reaction temperature is controlled to 10 to 50 ℃.
6. A method for producing tris (dimethylamine) cyclopentadienylhafnium according to claim 1, wherein the heating temperature in S5 is 20 to 80 degrees when cyclopentene is obtained and 30 to 60 degrees when cyclopentadiene is obtained.
7. A method of producing tris (dimethylamine) cyclopentadienylhafnium according to claim 2, wherein the molar ratio of the lithium salt of dimethylamide to hafnium tetrachloride in S1 is 0.5-2: 0.2-3.
8. A method of producing tris (dimethylamine) cyclopentadienylhafnium according to claim 6, wherein the S5 is prepared by using an alcoholic solution of monobromocyclopentane and sodium hydroxide in a molar ratio of 0.5-2:5-10, and diluting with ethylbenzene during distillation in S6.
CN202010775113.4A 2020-08-05 2020-08-05 Production method of tris (dimethylamine) cyclopentadiene hafnium Pending CN112062792A (en)

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CN114773403A (en) * 2022-05-27 2022-07-22 苏州欣诺科生物科技有限公司 Synthesis method of tri (dialkylamino) cyclopentadienyl metal complex

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CN101341155A (en) * 2005-12-06 2009-01-07 Tri化学研究所股份有限公司 Hafnium compound, hafnium thin film-forming material and method for forming hafnium thin film
CN107188908A (en) * 2017-06-26 2017-09-22 江苏南大光电材料股份有限公司 Three（Dimethylamino）The preparation method of cyclopentadienyl group zirconium
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114773403A (en) * 2022-05-27 2022-07-22 苏州欣诺科生物科技有限公司 Synthesis method of tri (dialkylamino) cyclopentadienyl metal complex
CN114773403B (en) * 2022-05-27 2024-01-05 苏州欣诺科生物科技有限公司 Synthesis method of tri (dialkylamino) cyclopentadienyl metal complex

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