CN115477578A - Purification method of nonanoyl chloride - Google Patents
Purification method of nonanoyl chloride Download PDFInfo
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- CN115477578A CN115477578A CN202211269998.6A CN202211269998A CN115477578A CN 115477578 A CN115477578 A CN 115477578A CN 202211269998 A CN202211269998 A CN 202211269998A CN 115477578 A CN115477578 A CN 115477578A
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- dioxane
- dmf
- nonanoyl chloride
- mixture
- chloride
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- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 title claims abstract description 62
- 238000000034 method Methods 0.000 title claims abstract description 43
- 238000000746 purification Methods 0.000 title claims abstract description 18
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000002156 mixing Methods 0.000 claims abstract description 12
- 239000011541 reaction mixture Substances 0.000 claims abstract description 11
- 238000004821 distillation Methods 0.000 claims abstract description 9
- 150000001263 acyl chlorides Chemical class 0.000 claims abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 33
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 21
- 239000012535 impurity Substances 0.000 abstract description 19
- 230000008569 process Effects 0.000 abstract description 12
- 239000007864 aqueous solution Substances 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 61
- 239000002351 wastewater Substances 0.000 description 13
- 238000001514 detection method Methods 0.000 description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000945 filler Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229960001929 meloxicam Drugs 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 238000005262 decarbonization Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/64—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a purification method of nonanoyl chloride, which specifically comprises the following steps: adding an entrainer into the acyl chloride reaction mixture, fully mixing at room temperature, and carrying out distillation treatment at the temperature of 30-45 ℃ under the pressure of-0.08-0.09 MPa; the entrainer is mainly 1,4-dioxane. The invention is used for removing DMF impurities from DMF-containing nonanoyl chloride products. The process does not use water and aqueous solutions, avoids possible damage to nonanoyl chloride by water, and provides a suitable protocol for removing DMF from the nonanoyl chloride product. By applying the method provided by the scheme to treat DMF impurities in nonanoyl chloride, the content of the DMF impurities in nonanoyl chloride can be reduced to be below 0.03% at a lower temperature, so that the physicochemical state of nonanoyl chloride is ensured, and the energy consumption of the process of removing the DMF impurities from nonanoyl chloride is lower.
Description
Technical Field
The invention relates to a purification method, in particular to a purification method of nonanoyl chloride, which is used for removing DMF impurities from a DMF-containing nonanoyl chloride product.
Background
N, N-Dimethylformamide (DMF) is one of the common solvents used in organic synthesis, is often used as a solvent or catalyst in the synthesis of acid chlorides, and in order to obtain a product meeting the purity requirement, it is usually necessary to remove the introduced DMF from the reaction product so as to obtain the target product with the desired purity. Conventionally, there are several methods for removing DMF from the reaction mixture. The first method is water washing or extraction separation, and the product is separated by using solubility. The second method is high vacuum distillation, suitable for the purification of products that are less sensitive to temperature. The third method is azeotropic distillation, using acetonitrile or more than ten times of water as entrainer to make azeotrope with DMF.
In order to remove DMF contained in the mixture more efficiently, the skilled person is continuously proposing some innovations and improvements; the invention application with the publication number of CN01128086.7 provides a refining process of meloxicam, wherein a method and a step are provided for reducing the content of crude meloxicam with the DMF content of more than 1000ppm to less than 10ppm after the crude meloxicam is treated by an alkaline alcohol solution. The invention application number of 202111560948 provides a method for treating DMF-containing wastewater, which comprises the steps of firstly adjusting the mixture to a specified acidity and temperature range, then performing alkaline hydrolysis for a certain time, and then performing tower treatment. The waste water with DMF content of 15-20 g/L can be treated to DMF content below 0.08g/L and DMF removing efficiency over 99.6%.
In 2019, liu Guo and the like research the detection influence factors of DMF wastewater treatment by an air stripping method. The result shows that, when dimethylamine is added into 5mL of DMF standard solution (100 mg/L), the absorbance and the addition amount of dimethylamine are in good linear relation within the range of 0-142 mg of dimethylamine, the linear equation is y = -0.000 7x +0.311 2, and the correlation coefficient (r) is 0.970 0. When dimethylamine was added in an amount of 178mg, a red precipitate was produced. After the influence of dimethylamine is removed, the recovery rate is 94.7-97.9 percent and the Relative Standard Deviation (RSD) is 3.79-7.70 percent under different standard adding levels.
In 2020, gao Yanfang and the like utilize centrifugal extraction to treat high-concentration DMF wastewater, examine the influence of phase ratio, stage number and flow rate on the DMF extraction effect, and determine the optimal conditions for treating the DMF wastewater. From the results, the preferred operation conditions are that the total flow rate of the feed is controlled within 600mL/min and the DMF content in the raffinate is lower than 1% compared with O/A = 1: 1 (volume ratio) and three-stage countercurrent. Simultaneously, a series of problems in the prior art are solved, and the treatment cost of the wastewater is greatly reduced. In the same year, xu Kunlun and the like reported that DMF organics in wastewater can be reasonably recovered by applying a self-developed pressure reduction device or a rectification device and the like.
In 2021, ma Ruili and the like adopt a 2-grade A/O-HBR process to treat N, N-Dimethylformamide (DMF) wastewater, and comparative experimental research is carried out on the denitrification and decarbonization effects of the process of adding the high-efficiency biological rope filler and the polyurethane sponge filler. The result shows that 2 fillers can finish film forming in 21 days, and the removal rate of COD reaches more than 95%; the TN removal effect of the polyurethane sponge filler is obviously better than that of the high-efficiency biological rope filler, the COD removal rate and the TN removal rate are respectively up to 97.35 percent and 88.85 percent, the shock load resistance is strong, the synchronous nitrification and denitrification reaction effect is obvious, and the method is more suitable for treating DMF wastewater in a 2-level A/O-HBR process.
In the same year, chen Luyuan and the like degrade DMF wastewater by taking titanium oxide-loaded activated carbon particles (TiO 2/AC) as three-dimensional electrodes and taking an iron plate and a graphite plate as an electrode anode and a cathode respectively. The influence of electrolytic voltage, pH, electrolyte concentration, electrolytic time and aeration quantity on the COD degradation effect of the DMF wastewater is investigated. The optimal condition of COD degradation effect is researched through an orthogonal test, and the research result shows that when the pH is 4, the voltage is 13V, the electrolyte concentration is 2.5g/L, the aeration amount is 1L/h, and the electrolysis time is 80min, the degradation rate of the COD of the DMF wastewater can reach 91%. The experimental result provides a certain reference value for the treatment of DMF organic wastewater.
In 2022, xia Yunkang and the like adopt a two-stage A/O-sponge filler process to treat DMF wastewater, and the segmented water inlet ratio (8: 2, 7: 1) of a first-stage A/O anoxic tank (A1) and a second-stage A/O anoxic tank (A2) is researched
3. 6: 4, 5: 5) on the denitrification and decarbonization efficiency of the system. The result shows that the two-stage A/O-sponge filler process can realize the high-efficiency removal of COD under the conditions of different sectional water inlet ratios, the average removal rate of the COD is over 95 percent, and the removal of TN, NO 3-N and NH4+ -N by the system is greatly influenced by the sectional water inlet ratios. Under the condition of higher (8: 2 and 7: 3) segmented water inlet ratio, the removal rate of the TN of the system is 81.39-89.03 percent, and the TN mainly exists in the forms of NH4+ -N and NO 3-N at the moment; when the segmented water inlet ratio is reduced to 6: 4, the TN removal rate of the system reaches an optimal value 91.33%, and the NH4+ -N and NO3- -N of effluent are obviously lower than the rest water inlet ratio working conditions and are respectively reduced to 8.04mg/L and 7.06mg/L.
The above schemes all use water or aqueous solutions, however, the above schemes are not suitable for removal of DMF from nonanoyl chloride. Pelargonyl chloride has strong water sensitivity, and can easily react with water when contacting with the water, so that the pelargonyl chloride is damaged by the water.
Therefore, the above scheme and technique are not applicable to remove DMF contained in pelargonyl chloride, and thus a purification method of pelargonyl chloride is needed.
Disclosure of Invention
The invention aims to provide a purification method of nonanoyl chloride, which is used for removing DMF impurities from a DMF-containing nonanoyl chloride product.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a purification method of pelargonyl chloride specifically comprises the following steps: adding an entrainer into the acyl chloride reaction mixture, fully mixing at room temperature, and carrying out distillation treatment at the temperature of 30-45 ℃ under the pressure of-0.08-0.09 MPa;
wherein the entrainer is mainly 1,4-dioxane.
Wherein the entrainer is 1,4-dioxane, 1,4-dioxane and toluene mixture or 1,4-dioxane and n-butyl ether mixture.
Further optimized, the adding amount of the entrainer is 0.5 to 10 times of the liquid volume of the acyl chloride reaction mixture.
Wherein the addition amount of the entrainer is 5 to 8 times of the liquid volume of the acyl chloride reaction mixture.
Wherein the 1,4-dioxane and toluene mixture is 1,4-dioxane and toluene mixed in proportion, and the mass fraction of 1,4-dioxane in the mixture is 50% -99%.
Further limit, the weight percentage of 1,4-dioxane in the mixture is 75-85%.
The mixture of 1,4-dioxane and n-butyl ether is a mixture obtained by mixing 1,4-dioxane and n-butyl ether in proportion, and the mass fraction of 1,4-dioxane in the mixture is 70% -99%.
Further optimizing, the weight percentage of 1,4-dioxane in the mixture is 85-95%.
Compared with the prior art, the invention has the following beneficial effects:
the invention is used for removing DMF impurities from DMF-containing nonanoyl chloride products. The process does not use water and aqueous solutions, avoids possible damage to nonanoyl chloride by water, and provides a suitable protocol for removing DMF from the nonanoyl chloride product. By applying the method provided by the scheme to treat DMF impurities in nonanoyl chloride, the content of the DMF impurities in nonanoyl chloride can be reduced to below 0.03% at a lower temperature, so that the physical and chemical states of the nonanoyl chloride are ensured, and the energy consumption in the process of removing the DMF impurities from the nonanoyl chloride is lower.
Detailed Description
The following disclosure provides many different embodiments or examples for implementing different configurations of embodiments of the invention. To simplify the disclosure of embodiments of the invention, the components and arrangements of specific examples are described below. Of course, they are merely examples and are not intended to limit embodiments of the invention. Moreover, embodiments of the present invention may repeat reference numerals and/or reference letters in the various examples for purposes of simplicity and clarity and do not in themselves dictate a relationship between the various embodiments and/or configurations discussed.
Example one
The embodiment discloses a purification method of nonanoyl chloride, which specifically comprises the following steps: adding an entrainer into the acyl chloride reaction mixture, fully mixing at room temperature, and carrying out distillation treatment at the temperature of 30-45 ℃ under the pressure of-0.08-0.09 MPa; preferably distillation treatment at-0.08 MPa and 40 ℃;
wherein the entrainer is mainly 1,4-dioxane.
Further optimized, the entrainer is 1,4-dioxane, 1,4-dioxane and toluene or 1,4-dioxane and n-butyl ether.
Wherein the entrainer is added in an amount of 0.5 to 10 times, preferably 6 times, the liquid volume of the acid chloride reaction mixture.
Further defined, the entrainer is added in an amount of 5 to 8 times the liquid volume of the acid chloride reaction mixture.
Wherein the 1,4-dioxane and toluene mixture is 1,4-dioxane and toluene mixed in proportion, and the mass fraction of 1,4-dioxane in the mixture is 50% -99%.
Further defined, the weight percentage of 1,4-dioxane in the mixture is 75% -85%, and 70% is preferred.
Wherein the 1,4-dioxane and n-butyl ether mixture is 1,4-dioxane and n-butyl ether which are mixed in proportion, and the mass fraction of 1,4-dioxane in the mixture is 70-99%.
Further limiting, the weight percentage of 1,4-dioxane in the mixture is 85% -95%.
To facilitate a further understanding of the invention by those skilled in the art, the invention is further described below in conjunction with specific embodiments.
Case one
Taking a nonanoyl chloride crude product with 19.48 percent of DMF (N, N-dimethylformamide) impurity content, adding 5 times of 1,4-dioxane, uniformly mixing, carrying out reduced pressure distillation at-0.09 MP pressure and 60 ℃ until no obvious distillate exists, and carrying out gas phase detection (according to a gas phase detection standard) on the obtained nonanoyl chloride, wherein the detection result shows that after the nonanoyl chloride crude product is treated by 1,4-dioxane, the residual DMF content can be reduced to 0.02 percent.
Case two
Taking a nonanoyl chloride crude product with 19.48 percent of DMF impurity content, adding a mixture of 1,4-dioxane and toluene with 6 times volume, wherein the weight percentage content of 1,4-dioxane in the mixture is 70 percent, the weight percentage content of toluene in the mixture is 30 percent, and uniformly mixing;
carrying out reduced pressure distillation at the pressure of-0.08 MP and the temperature of 60 ℃ until no obvious distillate exists, and carrying out gas phase detection on the obtained nonanoyl chloride to obtain a detection result, wherein the detection result shows that the residual DMF content of the crude nonanoyl chloride can be reduced to 0.02 percent after the crude nonanoyl chloride is treated by the method.
Case three
Taking a nonanoyl chloride crude product with 19.48 percent of DMF impurity content, adding a mixture of 1,4-dioxane and n-butyl ether with the volume being 8 times that of the nonanoyl chloride crude product, wherein the weight percentage content of 1,4-dioxane in the mixture is 80 percent, the weight percentage content of n-butyl ether in the mixture is 20 percent, and uniformly mixing;
carrying out reduced pressure distillation at the pressure of-0.09 MP and the temperature of 58 ℃ until no obvious distillate exists, and carrying out gas phase detection on the obtained nonanoyl chloride to obtain a detection result, wherein the detection result shows that the residual DMF content of the crude nonanoyl chloride can be reduced to 0.03 percent after the crude nonanoyl chloride is treated by the method.
Case four
Taking two parts of crude nonanoyl chloride with the DMF impurity content of 19.48%, respectively adding dichloromethane and toluene with the volume being 6 times that of the crude nonanoyl chloride, uniformly mixing, carrying out reduced pressure distillation at the pressure of-0.09 MP and the temperature of 58 ℃ until no obvious distillate exists, and carrying out gas phase detection on the obtained nonanoyl chloride to obtain two samples with the residual DMF contents of 10.49% and 15.22% respectively.
Case five
Taking a nonanoyl chloride crude product with 19.48 percent of DMF impurity content, adding 1,4-dioxane with 6 times volume and water with the same volume, uniformly mixing, keeping the temperature at 60 ℃ for 1 hour, sampling and analyzing, wherein the nonanoyl chloride content is reduced by 30 percent, and the existence of the water shows that the nonanoyl chloride causes reaction or conversion.
According to the first to fifth cases, the nonanoyl chloride is purified by using the 1,4-dioxane as the main entrainer, so that the residual DMF content can be effectively reduced. The invention is used for removing DMF impurities from DMF-containing nonanoyl chloride products. The process does not use water and aqueous solutions, avoids possible damage to nonanoyl chloride by water, and provides a suitable protocol for removing DMF from the nonanoyl chloride product. By applying the method provided by the scheme to treat DMF impurities in nonanoyl chloride, the content of the DMF impurities in nonanoyl chloride can be reduced to be below 0.03% at a lower temperature, so that the physicochemical state of nonanoyl chloride is ensured, and the energy consumption of the process of removing the DMF impurities from nonanoyl chloride is lower.
While preferred embodiments of the present invention have been described, additional variations and modifications in those embodiments may occur to those skilled in the art once they learn of the basic inventive concepts. Therefore, it is intended that the appended claims be interpreted as including preferred embodiments and all such alterations and modifications as fall within the scope of the invention.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, it should be noted that any modifications, equivalents and improvements made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (8)
1. The purification method of pelargonyl chloride is characterized by comprising the following steps: adding an entrainer into the acyl chloride reaction mixture, fully mixing at room temperature, and carrying out distillation treatment at the temperature of 30-45 ℃ under the pressure of-0.08-0.09 MPa;
wherein the entrainer is mainly 1,4-dioxane.
2. The purification method of nonanoyl chloride according to claim 1, wherein: the entrainer is 1,4-dioxane, 1,4-dioxane and toluene mixture or 1,4-dioxane and n-butyl ether mixture.
3. The purification method of nonanoyl chloride according to claim 1, wherein: the adding amount of the entrainer is 0.5 to 10 times of the liquid volume of the acyl chloride reaction mixture.
4. The purification method of nonanoyl chloride according to claim 3, wherein: the amount of entrainer added is 5-8 times the volume of the liquid acyl chloride reaction mixture.
5. The purification method of nonanoyl chloride according to claim 2, wherein: 1,4-dioxane and toluene mixture is specifically 1,4-dioxane and toluene mixture obtained by mixing in proportion, wherein the weight fraction of 1,4-dioxane in the mixture is 50% -99%.
6. The purification method of nonanoyl chloride according to claim 5, wherein: the weight percentage of the 1,4-dioxane in the mixture is 75-85%.
7. The purification method of nonanoyl chloride according to claim 5, wherein: 1,4-dioxane and n-butyl ether mixture is specifically 1,4-dioxane and n-butyl ether mixture obtained by mixing in proportion, and the mass fraction of 1,4-dioxane in the mixture is 70% -99%.
8. The purification method of nonanoyl chloride according to claim 7, wherein: the weight percentage of the 1,4-dioxane in the mixture is 85-95%.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007061087A (en) * | 2005-08-04 | 2007-03-15 | Univ Of Tokyo | New artificial base pair and utilization of the same |
| WO2012129792A1 (en) * | 2011-03-30 | 2012-10-04 | 中国科学院上海药物研究所 | Pyrimidinone compounds, preparation methods, pharmaceutical compositions and uses thereof |
| CN102942470A (en) * | 2012-11-02 | 2013-02-27 | 常州大学 | Production technology of pharmaceutical grade valeryl chloride |
| CN108299190A (en) * | 2018-03-07 | 2018-07-20 | 福州大学 | A kind of method of separation and azeotropic system |
| CN111646893A (en) * | 2020-06-03 | 2020-09-11 | 宁波海曙琼杰化工技术研发工作室 | Preparation method of 2,4, 6-trimethylbenzoyl chloride |
-
2022
- 2022-10-18 CN CN202211269998.6A patent/CN115477578B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007061087A (en) * | 2005-08-04 | 2007-03-15 | Univ Of Tokyo | New artificial base pair and utilization of the same |
| WO2012129792A1 (en) * | 2011-03-30 | 2012-10-04 | 中国科学院上海药物研究所 | Pyrimidinone compounds, preparation methods, pharmaceutical compositions and uses thereof |
| CN102942470A (en) * | 2012-11-02 | 2013-02-27 | 常州大学 | Production technology of pharmaceutical grade valeryl chloride |
| CN108299190A (en) * | 2018-03-07 | 2018-07-20 | 福州大学 | A kind of method of separation and azeotropic system |
| CN111646893A (en) * | 2020-06-03 | 2020-09-11 | 宁波海曙琼杰化工技术研发工作室 | Preparation method of 2,4, 6-trimethylbenzoyl chloride |
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