CN117126208A - Synthesis method of (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt - Google Patents
Synthesis method of (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt Download PDFInfo
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- CN117126208A CN117126208A CN202210551099.9A CN202210551099A CN117126208A CN 117126208 A CN117126208 A CN 117126208A CN 202210551099 A CN202210551099 A CN 202210551099A CN 117126208 A CN117126208 A CN 117126208A
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- butyne
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- PPWNCLVNXGCGAF-UHFFFAOYSA-N 3,3-dimethylbut-1-yne Chemical compound CC(C)(C)C#C PPWNCLVNXGCGAF-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 239000010941 cobalt Substances 0.000 title claims abstract description 50
- 229910017052 cobalt Inorganic materials 0.000 title claims abstract description 50
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000001308 synthesis method Methods 0.000 title abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- 239000002904 solvent Substances 0.000 claims abstract description 24
- 239000000047 product Substances 0.000 claims abstract description 21
- 239000013067 intermediate product Substances 0.000 claims abstract description 18
- 238000002156 mixing Methods 0.000 claims abstract description 10
- 239000012298 atmosphere Substances 0.000 claims abstract description 4
- 230000001681 protective effect Effects 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims description 25
- 238000004821 distillation Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 230000002194 synthesizing effect Effects 0.000 claims description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 5
- 238000000746 purification Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical group CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000013341 scale-up Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- SHXUSAVSZLLFIU-UHFFFAOYSA-N C(C)(C)(C)C#C.[Co] Chemical compound C(C)(C)(C)C#C.[Co] SHXUSAVSZLLFIU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt, which comprises the following steps: uniformly mixing octacarbonyl cobalt and a solvent in a protective gas atmosphere to obtain an intermediate product; 3, 3-dimethyl-1-butyne is added into the intermediate product in a dropwise manner, and a pre-product is obtained after the reaction; and separating the pre-product to obtain (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt. The synthesis method of the (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt has the advantages of simple operation steps, short time consumption, high yield and low cost.
Description
Technical Field
The invention relates to the field of fine chemical industry, in particular to a method for synthesizing (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt.
Background
Cobalt (3, 3-dimethyl-1-butyne) hexacarbonyl is an important precursor for CVD/ALD, and cobalt-containing precursors, formed by deposition, have been used for functional layers such as passivation layers, insulating layers, etc. in integrated circuit fabrication and have great potential for use as wiring and interconnects in chips.
The Chinese patent with publication number of CN110818745A provides a preparation method of (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt; under the protection of nitrogen atmosphere, adding a cobalt carbonyl reagent and 1500-2000 parts of hydrocarbon solvent into a reactor, controlling the temperature to be 0-30 ℃, slowly adding 0.1-0.5 part of ionic liquid modified graphene oxide material and 20-30 parts of tertiary butyl acetylene into the system, and stirring and reacting for 1-10 hours under the protection of nitrogen atmosphere after the addition; filtering after the reaction is finished, distilling the obtained filtrate to remove volatile components to obtain a (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt coarse product, and purifying to obtain the (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt. The preparation method has strong operability, less reaction byproducts and higher yield. However, the method has more steps, complex operation, longer whole flow time and more reaction materials, and is unfavorable for purification. And the solvent ratio is too large, so that the actual products obtained by one-time synthesis are fewer for the reaction kettle with fixed volume. Meanwhile, the method has the defects of high cost and low benefit.
Disclosure of Invention
The invention aims to provide a synthesis method of (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt, which has the advantages of simple steps, short time consumption, high yield and low cost.
In order to achieve the above object, an embodiment of the present invention provides a method for synthesizing (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt, comprising the steps of: uniformly mixing octacarbonyl cobalt and a solvent in a protective gas atmosphere to obtain an intermediate product; 3, 3-dimethyl-1-butyne is added into the intermediate product in a dropwise manner, and a pre-product is obtained after the reaction; and separating the pre-product to obtain (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt.
In one or more embodiments of the invention, the molar ratio of the cobalt octacarbonyl, the solvent, and the 3, 3-dimethyl-1-butyne is 1:20-40:1.1-1.3.
In one or more embodiments of the present invention, the solvent is at least one of n-hexane, n-pentane; and/or the shielding gas is at least one of nitrogen and argon.
In one or more embodiments of the present invention, the mixing of the cobalt octacarbonyl and the solvent uniformly is specifically: mixing and stirring the cobalt octacarbonyl and the solvent for 3-5min.
Wherein, through stirring, uniform mixing can be realized; and meanwhile, the specific stirring time is adjusted according to the factors such as the size of the reaction kettle, the synthesis amount and the like.
In one or more embodiments of the invention, the addition of 3, 3-dimethyl-1-butyne drops to the intermediate product is in particular: 3, 3-dimethyl-1-butyne is added dropwise to the intermediate product at a rate of 1 to 10 drops/sec at a temperature of 5 to 25 ℃.
In one or more embodiments of the present invention, the synthesis method further comprises: 3, 3-dimethyl-1-butyne was distilled.
In one or more embodiments of the invention, the reaction time of the 3, 3-dimethyl-1-butyne and the intermediate product is from 1 to 4 hours.
In one or more embodiments of the invention, separating the pre-product specifically comprises: the pre-product is subjected to distillation treatment.
In one or more embodiments of the invention, the distillation treatment is an atmospheric distillation.
In one or more embodiments of the invention, the temperature of the distillation treatment is 70-100 ℃.
Compared with the prior art, the synthesis method of the (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt according to the embodiment of the invention has only three reaction raw materials, reduces the probability of impurity introduction and side reaction generation, and is beneficial to subsequent purification. The synthesis method has the advantages of simple operation steps, short time consumption, high yield and low cost, and has great value of industrial scale-up production.
Drawings
FIG. 1 is a schematic flow diagram of a process for the synthesis of (3, 3-dimethyl-1-butyne) hexacarbonyl cobaltate according to one embodiment of the present invention;
FIG. 2 is a nuclear magnetic resonance 1H spectrum of (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt prepared in example 1.
Detailed Description
The following detailed description of embodiments of the invention is, therefore, to be taken in conjunction with the accompanying drawings, and it is to be understood that the scope of the invention is not limited to the specific embodiments.
As shown in fig. 1, the synthesis method of (3, 3-dimethyl-1-butyne) hexacarbonyl cobaltous according to the preferred embodiment of the present invention comprises the following steps:
s1, uniformly mixing the octacarbonyl cobalt and the solvent in a protective gas atmosphere to obtain an intermediate product.
In S1, the shielding gas may be at least one of nitrogen and argon. The solvent may be at least one of n-hexane and n-pentane. The effect of the shielding gas can play a role in reducing the probability of side reactions.
In order to uniformly mix the cobalt octacarbonyl and the solvent, the cobalt octacarbonyl and the solvent can be mixed and stirred for 3-5min. And the stirring rate may be 700-1100r/s. Stirring can play a role in quickly and uniformly mixing the octacarbonyl cobalt and the solvent, and the efficiency of the whole synthesis method is improved. Through stirring, uniform mixing can be realized. In other embodiments, if the amount of raw materials is too large or the reaction vessel is different, the stirring rate and time can be adjusted according to the size of the reaction vessel and the amount of synthesis.
S2, dropwise adding 3, 3-dimethyl-1-butyne into the intermediate product, and obtaining a pre-product after reaction.
In S2, 3-dimethyl-1-butyne is added dropwise to the intermediate product at a rate of 1 to 10 drops/sec at a temperature of 5 to 25 ℃. The utilization rate of each raw material can be improved by slowly dripping, and the probability of side reaction is reduced.
In S2, 3-dimethyl-1-butyne may be distilled first, and then the distilled 3, 3-dimethyl-1-butyne may be added dropwise to the intermediate product. And 3, 3-dimethyl-1-butyne is preferably distilled at present, which is favorable for improving the purity of the final (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt and avoiding introducing new impurities.
In the above step, the reaction time of 3, 3-dimethyl-1-butyne and the intermediate product is 1 to 4 hours. According to different reaction temperatures, the reaction time is different, so that the 3, 3-dimethyl-1-butyne and the intermediate product can be fully reacted.
S3, separating a pre-product to obtain (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt.
In S3, the step of separating the pre-product may specifically include: the pre-product is subjected to distillation. Because only three reaction raw materials exist in the synthesis method, the probability of impurity introduction and side reaction generation is reduced, and the purification effect can be achieved by adopting the normal pressure distillation mode in the distillation treatment. The normal pressure distillation mode can be used for simplifying the purification equipment. The cost of the synthesis method is reduced.
In the above step, the temperature of the distillation treatment may be 70 to 100 ℃. The specific temperature may be determined according to the boiling point of the product.
In S1 and S2, the molar ratio of cobalt carbonyl, solvent and 3, 3-dimethyl-1-butyne is 1:20-40:1.1-1.3.
The synthesis of (3, 3-dimethyl-1-butyne) hexacarbonyl cobaltate according to the present invention is described in detail below with reference to specific examples.
Example 1
Under the nitrogen atmosphere, 0.1mol of octacarbonyl cobalt and 2mol (about 250 ml) of normal hexane solvent are sequentially added into the reaction kettle, the stirring speed is 900r/s, and the stirring is carried out for 3min until octacarbonyl cobalt is completely dissolved. The temperature of the reaction kettle is kept at 15 ℃, stirring is started, then 0.12mol of 3, 3-dimethyl-1-butyne just distilled is dripped into the reaction kettle at the speed of 3 drops/second, and stirring reaction is kept for 2H after the dripping is completed. After the reaction is finished, heating the reaction kettle to 75 ℃ under normal pressure for distillation, and finishing the reaction after no liquid is distilled out to obtain the (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt.
The yield of (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt in this example was 85%.
Example 2
Under the nitrogen atmosphere, 0.1mol of cobaltosic octacarbonyl and 3mol (about 250 ml) of normal hexane solvent are sequentially added into the reaction kettle, the stirring speed is 700r/s, and the stirring is carried out for 4min until the cobaltosic octacarbonyl is completely dissolved. The temperature of the reaction kettle is kept at 5 ℃, stirring is started, then 0.11mol of 3, 3-dimethyl-1-butyne just distilled is dripped into the reaction kettle at the speed of 1 drop/second, and stirring reaction is kept for 1H after the dripping is completed. After the reaction is finished, heating the reaction kettle to 70 ℃ under normal pressure for distillation, and finishing the reaction after no liquid is distilled out to obtain the (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt.
The properties of the product obtained were tested to be substantially identical to those of example 1.
Example 3
Under the nitrogen atmosphere, 0.1mol of octacarbonyl cobalt and 4mol (about 250 ml) of normal hexane solvent are sequentially added into the reaction kettle, the stirring speed is 1100r/s, and the stirring is carried out for 5min until octacarbonyl cobalt is completely dissolved. The temperature of the reaction kettle is kept at 25 ℃, stirring is started, then 0.13mol of 3, 3-dimethyl-1-butyne just distilled is dripped into the reaction kettle at the speed of 10 drops/second, and stirring reaction is kept for 4H after the dripping is completed. After the reaction is finished, heating the reaction kettle to 85 ℃ under normal pressure for distillation, and finishing the reaction after no liquid is distilled out to obtain the (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt.
The properties of the product obtained were tested to be substantially identical to those of example 1.
Example 4
Under the argon atmosphere, 0.1mol of octacarbonyl cobalt and 35mol (about 250 ml) of n-pentane solvent are sequentially added into the reaction kettle, the stirring speed is 1000r/s, and the stirring is carried out for 5min until the octacarbonyl cobalt is completely dissolved. The temperature of the reaction kettle is kept at 20 ℃, stirring is started, then 0.12mol of 3, 3-dimethyl-1-butyne just distilled is dripped into the reaction kettle at the rate of 5 drops per second, and stirring reaction is kept for 3H after the dripping is completed. After the reaction is finished, heating the reaction kettle to 100 ℃ under normal pressure for distillation, and finishing the reaction after no liquid is distilled out to obtain the (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt.
The product obtained was tested for properties substantially identical to those of example 1, and the yields were: .
FIG. 2 is a nuclear magnetic resonance 1H spectrum of (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt prepared in example 1. From the chemical shift and integral area ratio on the hydrogen spectrum, the final product can be proved to be CCTBA, and the hydrogen spectrum has fewer impurity peaks, which indicates that the synthesized CCTBA has higher purity.
In summary, the synthetic method of the invention has the following beneficial effects:
firstly, the concentration of cobalt carbonyl is increased by adopting lower solvent proportion, the probability of contact reaction with tertiary butyl acetylene is increased, and the reaction rate and the yield are greatly improved under the condition of not using a catalyst;
secondly, the lower solvent proportion improves the productivity of synthesizing the target product, reduces the cost, simplifies the purification equipment by using normal pressure distillation;
finally, the synthesis method of the invention has only three reaction raw materials, reduces the probability of impurity introduction and side reaction generation, and is beneficial to subsequent purification. Therefore, the synthesis method has the advantages of simple operation steps, short time consumption, high yield and low cost, and has great value of industrial scale-up production.
The foregoing descriptions of specific exemplary embodiments of the present invention are presented for purposes of illustration and description. It is not intended to limit the invention to the precise form disclosed, and obviously many modifications and variations are possible in light of the above teaching. The exemplary embodiments were chosen and described in order to explain the specific principles of the invention and its practical application to thereby enable one skilled in the art to make and utilize the invention in various exemplary embodiments and with various modifications as are suited to the particular use contemplated. It is intended that the scope of the invention be defined by the claims and their equivalents.
Claims (10)
1. A method for synthesizing (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt, which is characterized by comprising the following steps:
uniformly mixing octacarbonyl cobalt and a solvent in a protective gas atmosphere to obtain an intermediate product;
3, 3-dimethyl-1-butyne is added into the intermediate product in a dropwise manner, and a pre-product is obtained after the reaction; and
separating the pre-product to obtain (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt.
2. The method for synthesizing (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt according to claim 1, wherein the molar ratio of octacarbonyl cobalt, solvent and 3, 3-dimethyl-1-butyne is 1:20-40:1.1-1.3.
3. The method for synthesizing (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt according to claim 1, wherein said solvent is at least one of n-hexane and n-pentane; and/or the number of the groups of groups,
the shielding gas is at least one of nitrogen and argon.
4. The method for synthesizing (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt according to claim 1, wherein the method comprises the following steps of:
mixing and stirring the cobalt octacarbonyl and the solvent for 3-5min.
5. The method for synthesizing (3, 3-dimethyl-1-butyne) hexacarbonyl cobaltosic according to claim 1, wherein the dropwise addition of 3, 3-dimethyl-1-butyne to said intermediate product is in particular:
3, 3-dimethyl-1-butyne is added dropwise to the intermediate product at a rate of 1 to 10 drops/sec at a temperature of 5 to 25 ℃.
6. The method for synthesizing (3, 3-dimethyl-1-butyne) hexacarbonyl cobaltosic according to claim 1, further comprising:
3, 3-dimethyl-1-butyne was distilled.
7. The method for synthesizing (3, 3-dimethyl-1-butyne) hexacarbonyl cobaltosic according to claim 1, wherein the reaction time between said 3, 3-dimethyl-1-butyne and said intermediate product is 1 to 4 hours.
8. The method for synthesizing (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt according to claim 1, wherein said separation of said pre-product comprises:
the pre-product is subjected to distillation treatment.
9. The method for synthesizing (3, 3-dimethyl-1-butyne) hexacarbonyl cobaltosic acid according to claim 8, wherein said distillation treatment is an atmospheric distillation.
10. The method for synthesizing (3, 3-dimethyl-1-butyne) hexacarbonyl cobaltosic according to claim 8, wherein said distillation treatment is carried out at a temperature of 70 to 100 ℃.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210551099.9A CN117126208A (en) | 2022-05-18 | 2022-05-18 | Synthesis method of (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210551099.9A CN117126208A (en) | 2022-05-18 | 2022-05-18 | Synthesis method of (3, 3-dimethyl-1-butyne) hexacarbonyl cobalt |
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