CN107488136B - Method for preparing ethyl hydrogen sulfate - Google Patents
Method for preparing ethyl hydrogen sulfate Download PDFInfo
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- CN107488136B CN107488136B CN201710785694.8A CN201710785694A CN107488136B CN 107488136 B CN107488136 B CN 107488136B CN 201710785694 A CN201710785694 A CN 201710785694A CN 107488136 B CN107488136 B CN 107488136B
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- sulfate
- ethanol
- reaction
- ethyl
- hydrogen sulfate
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- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 title claims abstract description 77
- 238000000034 method Methods 0.000 title claims abstract description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 68
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical group [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 3
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
- 235000011152 sodium sulphate Nutrition 0.000 claims description 3
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims description 2
- 229910052939 potassium sulfate Inorganic materials 0.000 claims description 2
- 235000011151 potassium sulphates Nutrition 0.000 claims description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract description 26
- 229940008406 diethyl sulfate Drugs 0.000 abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 15
- 238000004821 distillation Methods 0.000 abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 239000000376 reactant Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 26
- 235000019441 ethanol Nutrition 0.000 description 18
- DIMZOVQGUDDSHG-UHFFFAOYSA-N ethene;sulfuric acid Chemical group C=C.OS(O)(=O)=O DIMZOVQGUDDSHG-UHFFFAOYSA-N 0.000 description 7
- ROAYSRAUMPWBQX-UHFFFAOYSA-N ethanol;sulfuric acid Chemical compound CCO.OS(O)(=O)=O ROAYSRAUMPWBQX-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000008104 plant cellulose Substances 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the field of chemical synthesis, in particular to a method for preparing ethyl hydrogen sulfate. The method takes ethanol and sulfur trioxide as reactants, and the ethyl bisulfate is generated by reaction under the action of a catalyst, the obtained ethyl bisulfate has high purity and low water content, and the hydrolysis reaction of the ethyl bisulfate and diethyl sulfate is weak in the distillation process of generating the diethyl sulfate by reaction, so that the yield of the diethyl sulfate is improved.
Description
Technical Field
The invention relates to the field of chemical synthesis, and relates to a method for preparing ethyl hydrogen sulfate.
Background
There are several methods for preparing ethyl hydrogen sulfate, such as: sulfuric acid-ethanol process, sulfuric acid-ethylene process.
The sulfuric acid-ethanol method comprises the following steps: mixing sulfuric acid and ethanol at a certain temperature for reaction to generate a mixture, wherein the reaction of the sulfuric acid and the ethanol is a reversible reaction, and the obtained mixture mainly contains ethyl bisulfate, water, unreacted sulfuric acid and unreacted ethanol; according to literature and experimental verification, the content of the ethyl bisulfate containing the ethyl bisulfate obtained by the sulfuric acid ethanol method is generally in the range of 20-60 percent, and the yield of the product obtained by producing the diethyl sulfate is low due to the large content of water.
The sulfuric acid-ethylene method is to introduce ethylene into sulfuric acid under the condition of controlling a certain temperature, and the mixture obtained through the process mainly contains diethyl sulfate, ethyl bisulfate and sulfuric acid; according to the literature (Zhang Piao Shui, scheme for the preparation of intermediates in the fine chemical industry, chemical industry Press, 1999, pp372-374), the mixture contained about 43% diethyl sulfate, 45% ethyl hydrogen sulfate and 12% sulfuric acid.
Reacting ethyl hydrogen sulfate at a certain temperature to generate diethyl sulfate and sulfuric acid, and carrying out reduced pressure distillation to obtain the diethyl sulfate. The reaction equation can be expressed as:
the temperature of the reaction reduced pressure distillation is generally 100-180 ℃.
When water is present in the system, the diethyl sulfate can generate ethanol and sulfuric acid under the catalysis of acid, the yield of the diethyl sulfate is reduced by the presence of the water, and the yield of the diethyl sulfate is reduced as the water content is larger. According to our research, ethyl hydrogen sulfate is obtained by an ethanol sulfate method in industrial scale production to produce diethyl sulfate, and the yield is only 10-30%.
The production of diethyl sulfate from ethyl hydrogen sulfate by the ethylene sulfate process has great advantages over the sulfuric acid-ethanol process. Because the former has no water or less water, in the subsequent process of obtaining diethyl sulfate by reduced pressure distillation, reversible reaction does not exist or the reversible reaction speed is slower. The sulfuric acid-ethylene method is also a better method for producing diethyl sulfate before, and the method for producing diethyl sulfate is an additional method for preparing ethanol by the ethylene sulfuric acid hydrolysis method and coproducing ethanol. However, the existing method for preparing ethanol by reacting ethylene and sulfuric acid and hydrolyzing is replaced by a plant cellulose fermentation method; and ethylene storage, transportation and handling operations are somewhat difficult. So that the preparation of ethyl hydrogen sulfate from ethylene-sulfuric acid is no longer possible and the process for the production of diethyl sulfate therefrom is no longer advantageous.
Disclosure of Invention
The invention provides a method for preparing ethyl hydrogen sulfate, which aims at solving the problems in the prior art, ethanol and sulfur trioxide are used as reactants and react under the action of a catalyst to obtain the ethyl hydrogen sulfate, the obtained ethyl hydrogen sulfate has high purity and low water content, and the hydrolysis reaction of the ethyl hydrogen sulfate and diethyl sulfate is weak in a distillation reaction, so that the yield of the diethyl sulfate is improved.
The ethyl hydrogen sulfate mentioned in the present invention actually contains a mixture of ethyl hydrogen sulfate, which may contain ethanol, water, sulfuric acid, diethyl sulfate, etc., but the content of ethyl hydrogen sulfate is high, and the mixture can be used for synthesizing diethyl sulfate (the yield can reach more than 85%), and can also be used in the manufacture of industrial products such as organic chemical industry, pesticides, medicines, etc.
The specific technical scheme of the invention is as follows:
a method for preparing ethyl hydrogen sulfate is characterized in that: the method comprises the following specific steps:
adding a certain amount of ethanol and a certain proportion of catalyst into a reactor, adding sulfur trioxide into a reaction solution, and controlling the reaction temperature to be-20-100 ℃ in the adding process to obtain ethyl bisulfate;
wherein the dosage of the catalyst is that the molar ratio of the catalyst to the ethanol is 0.001-1,
the ethanol is absolute ethanol or 95% ethanol;
the catalyst is sulfate or hydrochloride or phosphate or nitrate or carbonate of potassium, sodium, calcium, magnesium, aluminum, zinc, iron, tin, lead, copper and ammonium, or sulfuric acid;
the reaction time is preferably 0.1-20h, and the preferred time is 0.5-2 h;
further, the ethanol is absolute ethanol; the molar ratio of the catalyst to the ethanol is 0.05-0.15; the catalyst is sodium sulfate or potassium sulfate or ammonium sulfate;
the preferable reaction temperature is 5-60 ℃,
the invention provides a method for preparing ethyl hydrogen sulfate, which has the main advantages that:
1) anhydrous ethanol and sulfur trioxide are adopted to prepare the ethyl bisulfate in the presence of the catalyst, and no water is generated in the reaction process, so that the prepared ethyl bisulfate has high purity. In the preparation process, because the inorganic salt catalyst is added, the reaction speed can be accelerated, the ethanol is prevented from being carbonized by sulfur trioxide, and the generated ethyl hydrogen sulfate is colorless or light yellow.
2) Compared with the ethyl hydrogen sulfate prepared by the sulfuric acid-ethanol method, the sulfuric acid-ethanol method generates water by esterification reaction in the reaction process, and the water can promote ester to hydrolyze, so that a reversible reaction exists, only 20-60% of the ethyl hydrogen sulfate can be prepared, but the preparation process of the invention does not generate water, does not have the reversible reaction, can prepare the ethyl hydrogen sulfate with higher purity and less water content, and thus, the yield of subsequent reaction can be greatly improved; compared with the sulfuric acid-ethylene method, the sulfuric acid-ethylene method is a method for preparing ethanol by an ethylene sulfuric acid hydrolysis method and coproducing diethyl sulfate and is additionally used for producing diethyl sulfate, but the current method for preparing ethanol by reacting and hydrolyzing ethylene and sulfuric acid is replaced by a plant cellulose fermentation method; and ethylene storage, transportation and use operations have great difficulty. Therefore, the method provided by the invention has stronger advantages compared with the ethylene-sulfuric acid method.
In conclusion, the new method for preparing the ethyl bisulfate can greatly improve the purity of the ethyl bisulfate, further can greatly improve the yield of the reaction for preparing the diethyl sulfate from the ethyl bisulfate, and improves the economic benefit.
Detailed Description
The present invention is further described below in conjunction with examples which will allow those skilled in the art to more fully understand the present invention, but which are not intended to limit the invention in any way.
Example 1
A method for preparing ethyl hydrogen sulfate comprises the following specific steps:
1) and (2) placing the three-necked bottle with stirring in an ice-water bath, adding 100g of absolute ethyl alcohol into the three-necked bottle, adding 20g of sodium sulfate, starting stirring, adding 174g of sulfur trioxide into the reaction solution, controlling the reaction temperature to be about 50 ℃, and preserving the temperature at 50 ℃ for 30 minutes after the addition is finished to obtain the ethyl hydrogen sulfate.
Distilling the prepared ethyl bisulfate under reduced pressure at 150-160 ℃, controlling the vacuum degree at-0.095 MPa to obtain 151g of diethyl sulfate, washing the product twice, drying the product with anhydrous magnesium sulfate, filtering the drying agent to obtain 150g of the product with yield of 89.6 percent and main peak of 99.3 percent by GC, distilling the product under reduced pressure once (85-130 ℃/10mmHg) to obtain 148g of the product, wherein the purity of GC is 99.8 percent.
Example 2
A method for preparing ethyl hydrogen sulfate comprises the following specific steps:
1) and (3) placing the three-necked bottle with stirring in an ice-water bath, adding 100g of absolute ethyl alcohol into the three-necked bottle, adding 30g of ammonium sulfate, starting stirring, adding 174g of sulfur trioxide into the reaction solution, controlling the reaction temperature to be about 50 ℃, and preserving the temperature at 50 ℃ for 30 minutes after the addition is finished to obtain the ethyl hydrogen sulfate.
Distilling the prepared ethyl bisulfate under reduced pressure at 150-160 ℃, controlling the vacuum degree at-0.095 MPa to obtain 155g of diethyl sulfate, washing the product twice, drying the product with anhydrous magnesium sulfate, filtering the drying agent to obtain 154g of the product with the yield of 91.9 percent and the main peak of GC (gas chromatography) of over 99.2 percent, and distilling the product under reduced pressure once (85-130 ℃/10mmHg) to obtain 152g of the product with the purity of 99.7 percent by GC.
Therefore, the method for preparing the ethyl bisulfate can greatly improve the purity of the ethyl bisulfate, further greatly improve the yield of subsequent reaction using the ethyl bisulfate, improve the economic benefit and have great improvement compared with the prior method.
Claims (2)
1. A method for preparing ethyl hydrogen sulfate is characterized in that: the method comprises the following specific steps:
adding a certain amount of ethanol and a certain proportion of catalyst into a reactor, then adding sulfur trioxide into the reaction solution, and controlling the reaction temperature between minus 20 ℃ and 100 ℃ in the adding process and the reaction time between 0.1 hour and 20 hours to obtain ethyl hydrogen sulfate;
wherein the ethanol is absolute ethanol; the molar ratio of the catalyst to the ethanol is 0.05-0.15; the catalyst is sodium sulfate or potassium sulfate or ammonium sulfate.
2. The method of claim 1, wherein:
the reaction temperature is 5-60 ℃, and the reaction time is 0.5-2 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710785694.8A CN107488136B (en) | 2017-09-04 | 2017-09-04 | Method for preparing ethyl hydrogen sulfate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710785694.8A CN107488136B (en) | 2017-09-04 | 2017-09-04 | Method for preparing ethyl hydrogen sulfate |
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| CN107488136A CN107488136A (en) | 2017-12-19 |
| CN107488136B true CN107488136B (en) | 2020-04-14 |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110642755A (en) * | 2019-09-05 | 2020-01-03 | 泰安汉威集团有限公司 | Environment-friendly production process of diethyl sulfate |
| CN115449003B (en) * | 2021-06-09 | 2023-12-01 | 中国石油化工股份有限公司 | Preparation method of PVC resin with low film content and uniform pores |
| CN115028555B (en) * | 2022-07-04 | 2023-09-29 | 武汉青江化工黄冈有限公司 | Continuous synthesis process of diethyl sulfate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3047604A (en) * | 1958-11-14 | 1962-07-31 | Leatherman Martin | Process for manufacture of ethyl sulfuric acid |
| CN104744198A (en) * | 2015-03-25 | 2015-07-01 | 商洛学院 | Method for preparing ethylene in laboratory |
-
2017
- 2017-09-04 CN CN201710785694.8A patent/CN107488136B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3047604A (en) * | 1958-11-14 | 1962-07-31 | Leatherman Martin | Process for manufacture of ethyl sulfuric acid |
| CN104744198A (en) * | 2015-03-25 | 2015-07-01 | 商洛学院 | Method for preparing ethylene in laboratory |
Non-Patent Citations (2)
| Title |
|---|
| Synthesis of Sodium Ethylenesulfonate from Ethanol;David S. Breslow et al.;《Journal of the American Chemical Society》;19541105;第76卷;第5361-5363页 * |
| 硫酸二乙酯合成方法的研究;吴志广等;《化学试剂》;19911231;第13卷(第3期);第190、144页 * |
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