CN119306755A - N-methyl-N-(trimethylsilyl)acetamide and preparation method thereof - Google Patents
N-methyl-N-(trimethylsilyl)acetamide and preparation method thereof Download PDFInfo
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- CN119306755A CN119306755A CN202411426182.9A CN202411426182A CN119306755A CN 119306755 A CN119306755 A CN 119306755A CN 202411426182 A CN202411426182 A CN 202411426182A CN 119306755 A CN119306755 A CN 119306755A
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- trimethylsilyl
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- acetamide
- methyl
- triethylamine
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- QHUOBLDKFGCVCG-UHFFFAOYSA-N n-methyl-n-trimethylsilylacetamide Chemical compound CC(=O)N(C)[Si](C)(C)C QHUOBLDKFGCVCG-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 126
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims abstract description 62
- 239000005051 trimethylchlorosilane Substances 0.000 claims abstract description 29
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000002994 raw material Substances 0.000 claims abstract description 17
- 238000003825 pressing Methods 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 73
- 239000011261 inert gas Substances 0.000 claims description 9
- 239000000706 filtrate Substances 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000012065 filter cake Substances 0.000 claims description 5
- 238000004321 preservation Methods 0.000 claims description 5
- 238000005086 pumping Methods 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims 2
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 13
- 238000009776 industrial production Methods 0.000 abstract description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- BCDGQXUMWHRQCB-UHFFFAOYSA-N aminoacetone Chemical compound CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- -1 nitrogen-containing organic base Chemical class 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 229910052704 radon Inorganic materials 0.000 description 1
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000011863 silicon-based powder Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 238000005475 siliconizing Methods 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/20—Purification, separation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
本申请公开了一种N‑甲基‑N‑(三甲基硅基)乙酰胺及其制备方法，该制备方法包括：S100、采用包括N‑甲基乙酰胺和三甲基氯硅烷的原料，在三乙胺体系下反应，获得第一物料；S200、将所述第一物料依次进行压滤、浓缩和精馏，获得所述N‑甲基‑N‑(三甲基硅基)乙酰胺。本发明采用成本低廉、安全可靠的原料，在常压和较低的温度条件下反应制备N‑甲基‑N‑(三甲基硅基)乙酰胺，提供了一种安全环保、成本低廉、工艺简单、适合工业化生产的N‑甲基‑N‑(三甲基硅基)乙酰胺制备方法。
The present application discloses a kind of N-methyl-N-(trimethylsilyl)acetamide and preparation method thereof, and the preparation method comprises: S100, using raw materials including N-methylacetamide and trimethylchlorosilane, reacting under triethylamine system, obtaining the first material; S200, pressing, concentrating and rectifying the first material in turn, obtaining the N-methyl-N-(trimethylsilyl)acetamide. The present invention adopts low-cost, safe and reliable raw materials, reacts and prepares N-methyl-N-(trimethylsilyl)acetamide under normal pressure and relatively low temperature conditions, and provides a kind of safe and environmentally friendly, low-cost, simple process, and suitable for industrial production N-methyl-N-(trimethylsilyl)acetamide preparation method.
Description
Technical Field
The invention relates to the field of chemical materials, in particular to preparation of N-methyl-N- (trimethylsilyl) acetamide.
Background
N-Methyl-N- (trimethylsilyl) acetamide (N-Methyl-N- (trimethylsilyl) acetamide) is a compound of great utility in organic synthesis. methyl-N- (trimethylsilyl) acetamide is mainly used as a protective agent and a siliconizing agent for introducing trimethylsilyl groups in organic molecules, thereby protecting certain functional groups from other agents. It can also be used as a trimethylsilylating reagent for polar compounds to improve the detection sensitivity and selectivity of analytes during derivatization of Gas Chromatography (GC) and gas chromatography-mass spectrometry (GC-MS).
In the prior art, N-methyl-N- (trimethylsilyl) acetamide is synthesized in two ways, T.R. bailey et al, science of Synthesis (science of synthesis), (2005), 21,811-31, by silylation of N-methylacetamide with trimethylchlorosilane, reaction in anhydrous benzene using triethylamine as nitrogen-containing organic base at a temperature of 0 ℃ to 5 ℃ to give the product N-methyl-N- (trimethylsilyl) acetamide, another synthesis method of N-methyl-N- (trimethylsilyl) acetamide is to directly react N-methylacetamide and N-trimethylsilylimidazole by heating to boiling at 13 mbar, the reaction temperature of the process is between 120 ℃ and 170 ℃, and the reaction product is to be removed by continuous distillation in 8 h. The synthesized crude product needs to be purified by further rectification, and finally the product N-methyl-N- (trimethylsilyl) acetamide is obtained.
The prior art has the defects that if benzene is used as a solvent, the benzene has high toxicity, and the benzene can harm the health of production personnel and is not beneficial to the environment. If N-trimethylsilicon imidazole is used, the cost is high, imidazole in the reaction process needs to be recovered in production, and then the imidazole is converted into the N-trimethylsilicon imidazole by means of hexamethyldisilazane, so that the method has high production cost, complex process and long reaction time. In addition, it is also very difficult to carry out the reaction using such a low pressure in industrial production.
In summary, how to provide a preparation method of N-methyl-N- (trimethylsilyl) acetamide, which is safe, environment-friendly, low in cost, simple in process and suitable for industrial production, is a technical problem to be solved by the technicians in the field.
Disclosure of Invention
The application aims to provide N-methyl-N- (trimethylsilyl) acetamide and a preparation method thereof, which can solve the technical problems of insufficient safety, environmental protection, high cost and complex process in the N-methyl-N- (trimethylsilyl) acetamide production process in the prior art.
In order to solve the technical problems, the application is realized as follows:
the application provides a preparation method of N-methyl-N- (trimethylsilyl) acetamide, which comprises the following steps:
S100, reacting raw materials comprising N-methylacetamide and trimethylchlorosilane in a triethylamine system to obtain a first material;
And S200, sequentially carrying out filter pressing, concentration and rectification on the first material to obtain the N-methyl-N- (trimethylsilyl) acetamide.
In the above technical solution, S100 specifically includes:
S110, under the protection of inert gas, the N-methylacetamide and the triethylamine are sent into a reaction kettle, and the reaction kettle is heated to the reaction temperature;
s120, controlling the reaction kettle to keep the reaction temperature, and dropwise adding the trimethylchlorosilane into the reaction kettle;
And S130, continuing the heat preservation reaction after the trimethylchlorosilane is added dropwise, and obtaining the first material.
In the above technical scheme, in S110, for each 100L of the triethylamine is charged, 15kg to 20kg of the N-methylacetamide is charged, and 20kg to 30kg of the trimethylchlorosilane is added dropwise, respectively.
In the above technical scheme, in S110, for each 100L of the triethylamine is charged, 16kg to 16.5kg of the N-methylacetamide is charged, and 24kg to 24.5kg of the trimethylchlorosilane is added dropwise, respectively.
In the above technical solution, in S110, the reaction temperature is 30 ℃ to 38 ℃.
In the above technical solution, in S120, the trimethylchlorosilane is controlled to be added dropwise within 4 hours.
In the above technical scheme, in S130, the time for continuing the incubation reaction is 1h.
In the above technical solution, S200 specifically includes:
s210, pressing the first material into a filter press under the protection of inert gas, after the filter cake is pressed to be dry, adding triethylamine for washing once, and continuously pressing to be dry to obtain filtrate;
s220, pumping the filtrate into a concentration kettle, removing the triethylamine under negative pressure, stopping concentrating under the condition of target temperature, and recovering the triethylamine to obtain a concentrated material;
s230, transferring the concentrated material to a rectifying tower for rectification to obtain the N-methyl-N- (trimethylsilyl) acetamide.
In the above technical solution, the target temperature condition is 60 ℃.
The invention also provides N-methyl-N- (trimethylsilyl) acetamide, which is obtained by adopting the preparation method according to any technical scheme.
Advantageous effects
The invention provides a preparation method of N-methyl-N- (trimethylsilyl) acetamide, which comprises the steps of firstly adopting raw materials comprising N-methylacetamide and trimethylchlorosilane to react under a triethylamine system to obtain a first material, and then sequentially carrying out filter pressing, concentration and rectification on the first material to obtain the N-methyl-N- (trimethylsilyl) acetamide. In the above method, the hydrogen atom on the nitrogen atom of N-methylacetamide is replaced with the trimethylsilyl group in trimethylchlorosilane, thereby producing N-methyl-N- (trimethylsilyl) acetamide. The raw material triethylamine is used as an acid binding agent and also used as a solvent in the reaction. Triethylamine is a colorless oily liquid, slightly soluble in water, but soluble in most organic solvents such as ethanol, diethyl ether, acetone, etc. This solubility allows triethylamine to act as a solvent for diluting the organic reactants and the active species, allowing the reactants to mix well during the reaction, thereby improving the reaction efficiency and polymer quality. In the reaction of the present invention, the production of acidic substances may reduce the efficiency and quality of the reaction. Triethylamine is used as weak base and can be used as acid binding agent to maintain the balance of reaction, thereby improving the reaction quality. In addition, when triethylamine is used as a solvent, it is easy to recover and handle by distillation or the like because of its relatively stable physical and chemical properties. This helps to reduce production costs and environmental pollution. In conclusion, the invention adopts the raw materials with low cost, safety and reliability, and prepares the N-methyl-N- (trimethylsilyl) acetamide by reaction under the conditions of normal pressure and lower temperature, and provides the preparation method of the N-methyl-N- (trimethylsilyl) acetamide, which is safe and environment-friendly, has low cost and simple process and is suitable for industrial production.
Drawings
FIG. 1 is a process flow diagram of a method for preparing N-methyl-N- (trimethylsilyl) acetamide according to an embodiment of the present invention.
Detailed Description
In order that the above-recited objects, features and advantages of the present invention will become more readily apparent, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings.
The reagents and starting materials used in the invention are commercially available unless otherwise specified. The experimental methods, in which specific conditions are not noted in the following examples, were selected according to conventional methods and conditions, or according to the commercial specifications.
The invention provides a preparation method of N-methyl-N- (trimethylsilyl) acetamide, which comprises the following steps:
S100, reacting raw materials comprising N-methylacetamide and trimethylchlorosilane in a triethylamine system to obtain a first material;
And S200, sequentially carrying out filter pressing, concentration and rectification on the first material to obtain the N-methyl-N- (trimethylsilyl) acetamide.
In the above step, N-methylacetamide and trimethylchlorosilane are used as reaction raw materials.
N-methylacetamide, also known as N-acetylmethylamine or methylacetamide, has the chemical formula C 3H7 NO, and N-methylacetamide generally exhibits white needle-like crystals at ordinary temperature. The N-methylacetamide of the present invention may be obtained commercially or may be obtained by reacting ethyl acetate with methylamine. Mixing ethyl acetate and 65% methylamine, heating to about 60 ℃, reacting for 4 days and nights until layering phenomenon is avoided, namely, after the reaction is finished, distilling under reduced pressure to recover ethanol, and collecting fractions at 95-110 ℃ to obtain the N-methylacetamide. Trimethylchlorosilane is an active compound that can react with a number of compounds. Trimethylchlorosilane is an important raw material for preparing silicon compounds such as silicone rubber, silicone oil, silicone resin and the like. It can also be used for preparing silane coupling agents, silylating agents and the like. The trimethylchlorosilane can be obtained through purchasing in a commercial way, or can be obtained through adopting methyl chloride and silicon powder as raw materials, adopting cuprous chloride as a catalyst to react to prepare a crude product, and then obtaining a finished product through processes such as rectification and purification, or can be obtained through adopting tetramethylsilane and acetyl chloride as raw materials and adding aluminum trichloride as a catalyst to react. By the embodiment of the present invention, the hydrogen atom on the nitrogen atom of N-methylacetamide is replaced by the trimethylsilyl group in trimethylchlorosilane, thereby producing N-methyl-N- (trimethylsilyl) acetamide.
In the present invention, triethylamine is used as both an acid-binding agent and a solvent in the reaction. Triethylamine is a colorless oily liquid, slightly soluble in water, but soluble in most organic solvents such as ethanol, diethyl ether, acetone, etc. This solubility allows triethylamine to act as a solvent for diluting the organic reactants and the active species, allowing the reactants to mix well during the reaction, thereby improving the reaction efficiency and polymer quality. In the reaction of the present invention, the production of acidic substances may reduce the efficiency and quality of the reaction. Triethylamine is used as weak base and can be used as acid binding agent to maintain the balance of reaction, thereby improving the reaction quality.
In addition, when triethylamine is used as a solvent, it is easy to recover and handle by distillation or the like because of its relatively stable physical and chemical properties. This helps to reduce production costs and environmental pollution.
The invention adopts the raw materials with low cost, safety and reliability, and prepares the N-methyl-N- (trimethylsilyl) acetamide by reaction under the conditions of normal pressure and lower temperature, thereby providing the preparation method of the N-methyl-N- (trimethylsilyl) acetamide, which is safe and environment-friendly, has low cost and simple process and is suitable for industrial production.
In some embodiments of the present invention, S100 specifically includes:
S110, under the protection of inert gas, the N-methylacetamide and the triethylamine are sent into a reaction kettle, and the reaction kettle is heated to the reaction temperature;
s120, controlling the reaction kettle to keep the reaction temperature, and dropwise adding the trimethylchlorosilane into the reaction kettle;
And S130, continuing the heat preservation reaction after the trimethylchlorosilane is added dropwise, and obtaining the first material.
In the above embodiments, the inert gas may be helium (He), neon (Ne), argon (Ar), krypton (Kr), xenon (Xe), radon (Rn, radioactivity), or the like. Preferably, nitrogen is used as inert gas in the present invention. And (3) under the protection of inert gas, the N-methylacetamide and the triethylamine are fed into a reaction kettle, and the aim of heating and raising the temperature is to avoid the decomposition of raw materials or reactants.
It will be appreciated that the reaction temperature has a significant impact on the quality and efficiency of the reaction of the present invention. The invention carries out the reaction under the condition of lower temperature. Preferably, the reaction temperature is from 30 ℃ to 38 ℃.
It is understood that the reaction temperature of the present invention is an interval value, the reaction vessel may be heated to a first reaction temperature after the N-methylacetamide and the triethylamine are fed into the reaction vessel, and the reaction vessel may be heated from the first reaction temperature to a second reaction temperature when the trimethylchlorosilane is added dropwise. Wherein the first reaction temperature and the second reaction temperature are within a temperature range of 30 ℃ to 38 ℃. Preferably, the dropwise addition of trimethylchlorosilane can be started under a temperature condition of 30 ℃, and the reaction temperature is controlled within a temperature interval of 30 ℃ to 38 ℃.
It will be appreciated that the rate of addition of the trimethylchlorosilane will have a significant impact on the quality and efficiency of the reaction of the present invention. The invention needs to control the trimethylchlorosilane to be added dropwise within 4 hours.
After the end of the dropwise addition of the trimethylchlorosilane, the thermal insulation reaction should be continued, and the first material may be obtained after the end of the thermal insulation reaction. Preferably, in S130, the time for continuing the incubation reaction is 1h.
It will be appreciated that the amount and ratio of each raw material added will also have a significant impact on the quality and efficiency of the reaction of the present invention. Preferably, in S110, each 100L of the triethylamine is charged, 15kg to 20kg of the N-methylacetamide is charged accordingly, and 20kg to 30kg of the trimethylchlorosilane is added dropwise accordingly. Further preferably, in S110, for each 100L of the triethylamine is charged, 16kg to 16.5kg of the N-methylacetamide is charged, respectively, and 24kg to 24.5kg of the trimethylchlorosilane is added dropwise, respectively.
After the reaction is finished, further filter pressing, concentration and rectification treatment are needed to be carried out on the first material. S200 specifically comprises:
s210, pressing the first material into a filter press under the protection of inert gas, after the filter cake is pressed to be dry, adding triethylamine for washing once, and continuously pressing to be dry to obtain filtrate;
s220, pumping the filtrate into a concentration kettle, removing the triethylamine under negative pressure, stopping concentrating under the condition of target temperature, and recovering the triethylamine to obtain a concentrated material;
s230, transferring the concentrated material to a rectifying tower for rectification to obtain the N-methyl-N- (trimethylsilyl) acetamide.
Preferably, the target temperature condition is 60 ℃.
It should be noted that in the preparation stage of the press filtration, it is necessary to ensure that the N-methyl-N- (trimethylsilyl) acetamide reaction mixture in the reactor has reacted sufficiently and reaches the desired conversion. Preferably, after the reaction is completed, the reaction medium may be cooled to a suitable temperature (e.g., 0-5 ℃) and then mixed with a suitable amount of solvent (e.g., hexane) to dilute the reaction mixture and promote the formation of precipitates. Solid impurities (e.g., triethylamine hydrochloride precipitate) can be removed by press filtration of the mixture using a press filter. In this process, it is ensured that the pressure and flow of the filter press are controlled within appropriate ranges to avoid damage to the product. Finally, washing the filter cake with a proper amount of triethylamine to remove residual impurities. The filtrate after washing and the washing liquid should be combined and recycled so as to remove the low boiling point solvent. This can be achieved by distillation or stripping, etc. After removal of the solvent, the remaining mixture was concentrated to increase the concentration of N-methyl-N- (trimethylsilyl) acetamide. This can be achieved by distillation under reduced pressure or evaporation by heating. In the process of feeding the reactant into the rectifying tower for rectification, the effective separation and purification of the N-methyl-N- (trimethylsilyl) acetamide can be realized by controlling parameters such as the temperature of the top of the tower, the temperature of the bottom of the tower, the reflux ratio and the like. The fraction collected at the top of the column is purified N-methyl-N- (trimethylsilyl) acetamide. And cooling, crystallizing, drying and the like to obtain a final product. It will be appreciated that in the whole process above, the person skilled in the art can control parameters such as temperature, pressure and flow rate according to actual needs, so as to ensure the quality and yield of the product. Through the steps, the effective filter pressing, concentration and rectification of the N-methyl-N- (trimethylsilyl) acetamide can be realized, so that a high-quality product is obtained.
Example 1
FIG. 1 is a process flow diagram of a method for preparing N-methyl-N- (trimethylsilyl) acetamide according to an embodiment of the present invention. As shown in FIG. 1, this example provides an industrial production method of N-methyl-N- (trimethylsilyl) acetamide, which uses N-methylacetamide and trimethylchlorosilane as raw materials to prepare N-methyl-N- (trimethylsilyl) acetamide by reaction in a triethylamine system.
The method comprises the following specific steps:
1. Raw material preparation, namely, under the protection of nitrogen, putting 1400L of triethylamine and 225 kg of N-methylacetamide into a 2000L reaction kettle, stirring and heating to 30 ℃. 340 kg of trimethylchlorosilane is added into the overhead tank;
2. And (3) dropwise adding, namely after the temperature of the reaction kettle is increased to 30 ℃, starting to dropwise add trimethylchlorosilane, controlling the reaction temperature to be 30-38 ℃, and finishing dropwise adding about 4 hours. The heat preservation reaction is carried out for one hour after the dripping;
3. after the heat preservation reaction is finished, nitrogen is opened to press the materials into a filter press, after the filter cake is pressed to be dry, 400 liters of triethylamine is added for washing once, and the press drying is continued;
4. concentrating, namely pumping the filtrate obtained in the previous step into a concentrating kettle, removing triethylamine under negative pressure until the kettle temperature reaches 60 ℃, and stopping concentrating. The recovered triethylamine is used for the next batch production;
5. and (3) rectifying, namely transferring the concentrated material to a rectifying tower, and rectifying to obtain a product.
Although the present invention is disclosed above, the present invention is not limited thereto. Various changes and modifications may be made by one skilled in the art without departing from the spirit and scope of the invention, and the scope of the invention should be assessed accordingly to that of the appended claims.
Claims (10)
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