CN113831213A - Method for preparing ethyl iodide by recycling iodine ion-containing solution - Google Patents
Method for preparing ethyl iodide by recycling iodine ion-containing solution Download PDFInfo
- Publication number
- CN113831213A CN113831213A CN202111209974.7A CN202111209974A CN113831213A CN 113831213 A CN113831213 A CN 113831213A CN 202111209974 A CN202111209974 A CN 202111209974A CN 113831213 A CN113831213 A CN 113831213A
- Authority
- CN
- China
- Prior art keywords
- containing solution
- iodine ion
- iodoethane
- preparing
- recovering
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 title claims abstract description 39
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000004064 recycling Methods 0.000 title abstract description 7
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229940008406 diethyl sulfate Drugs 0.000 claims abstract description 17
- 239000002808 molecular sieve Substances 0.000 claims abstract description 12
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 10
- -1 iodide ions Chemical class 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000004448 titration Methods 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 2
- 229940006461 iodide ion Drugs 0.000 claims description 2
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 claims description 2
- 229910001641 magnesium iodide Inorganic materials 0.000 claims description 2
- 238000011085 pressure filtration Methods 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052740 iodine Inorganic materials 0.000 abstract description 8
- 239000011630 iodine Substances 0.000 abstract description 8
- 238000011084 recovery Methods 0.000 abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 238000003825 pressing Methods 0.000 abstract description 2
- 238000011112 process operation Methods 0.000 abstract description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 206010018498 Goitre Diseases 0.000 description 1
- 102000018997 Growth Hormone Human genes 0.000 description 1
- 108010051696 Growth Hormone Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 201000003872 goiter Diseases 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 239000002920 hazardous waste Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910001505 inorganic iodide Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/389—Separation; Purification; Stabilisation; Use of additives by adsorption on solids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for preparing iodoethane by recycling iodine ion-containing solution, which comprises the steps of dropwise adding diethyl sulfate into the iodine ion-containing solution under the stirring state, distilling to obtain iodoethane, dewatering the collected iodoethane by a molecular sieve, and performing filter pressing to the collected iodoethane in a collecting tank, wherein the content of the obtained iodoethane is 99.9 percent, the water content is below 100ppm, the recovery rate of iodine in the solution is more than 90 percent, the process operation is simple, and the recovery rate is high.
Description
Technical Field
The invention relates to the field of recycling of iodine ion solution containing still residue, in particular to a method for preparing iodoethane by recycling iodine ion solution containing iodine.
Background
Iodothane is an important intermediate in organic synthesis, is an important raw material for synthesizing MO source, and is used as ethylation reagent, goiter therapeutic agent, plant growth hormone and the like. In the pharmaceutical industry as diagnostic aids and as analytical reagents, but also in organic synthesis. At present, in the production process, the content of iodide ions in kettle residues is 750g/L, and the content of iodide ions is rich, so that the iodide ions recovered from the iodine ion-containing solution are converted into iodoethane, the recovery and the reutilization of company raw materials can be realized, and the harmless treatment of waste liquid can be realized. In the prior art, red phosphorus, iodine and methanol are used for preparing ethyl iodide, the method has the advantages of large investment of devices, low yield, complex separation, incapability of recovering phosphoric acid and serious environmental pollution; therefore, it is very important to easily recover iodine-containing ions to prepare iodoethane.
Disclosure of Invention
In order to solve the problems, the invention provides a method for preparing iodoethane by recycling iodine ion solution, which comprises the steps of dropwise adding diethyl sulfate into the iodine ion solution under the stirring state, distilling to obtain the iodoethane, dewatering the collected iodoethane by a molecular sieve, and then performing filter pressing on the collected iodoethane into a collection tank, wherein the obtained iodoethane has the content of 99.9 percent, the water content is below 100ppm, the recovery rate of iodine in the solution is more than 90 percent, the process operation is simple, the recovery rate is high, and the problems in the background art are solved.
The invention aims to provide a method for preparing iodoethane by recovering iodine ion-containing solution, which is characterized by comprising the following steps: the method comprises the following steps:
the method comprises the following steps: the recovered iodine ion-containing solution is filtered to remove large particles;
step two: adding the iodine ion-containing solution filtered in the step one into a reaction kettle, maintaining the initial temperature at 30-80 ℃, and then dropwise adding diethyl sulfate;
step three: after the dropwise adding is finished, reacting for 4 hours, slowly raising the temperature of the bottom kettle, and carrying out fractional distillation to receive a distillate product until no liquid is dripped out of the receiving bottle;
step four: and after receiving, adding a molecular sieve, standing for 24 hours, filtering to obtain ethyl iodide, and finally performing pressure filtration to a collection tank.
The further improvement lies in that: and step one, filtering, and determining the content of iodide ions in the kettle residue by a titration method.
The further improvement lies in that: the iodide ions of the iodine ion-containing solution are potassium iodide or magnesium iodide.
The further improvement lies in that: and step two, slowly heating the iodine ion-containing solution to 70 ℃ under the condition of stirring, and then dropwise adding diethyl sulfate under the condition of stirring.
The further improvement lies in that: and adding diethyl sulfate for reaction in the second step, wherein the addition molar ratio of the diethyl sulfate is as follows: iodide ion/diethyl sulfate = 1/0.5-1.4.
The further improvement lies in that: the temperature of the reaction kettle is controlled to be 50-90 ℃, and the water content in the distilled ethyl iodide is reduced.
The further improvement lies in that: the adding amount of the molecular sieve in the step four is 1-10% of the weight of the iodoethane.
The further improvement lies in that: the molecular sieve is a zeolite molecular sieve or a UOP molecular sieve.
The experimental principle is as follows:
the invention has the beneficial effects that: the invention prepares the iodoethane from the iodine ion-containing solution, the iodine ion-containing solution removes solid particles by filtration, the diethyl sulfate is dripped, the iodoethane is received and the water is removed, on one hand, quantitative diethyl sulfate is dripped into the iodine kettle residual liquid, on the other hand, the reaction is promoted to be rapidly carried out by preheating the kettle residual liquid, and the final product of the iodoethane is obtained by filtration after the molecular sieve drying. The purity of the recovered ethyl iodide is more than 99 percent, the water content is less than 100ppm, and the yield of the recovered ethyl iodide is more than 90 percent. Simple process, short route, low equipment investment, simple operation, high recovery rate and easy industrialized production.
Detailed Description
In order to further understand the present invention, the following detailed description will be made with reference to the following examples, which are only used for explaining the present invention and are not to be construed as limiting the scope of the present invention.
The first embodiment is as follows:
taking 200ml of the recovered iodine ion-containing solution, filtering, and analyzing by a silver nitrate titration method to obtain 673g/L of iodine ion content;
adding 200ml of iodine-containing ion solution, starting stirring, and slowly heating to 70 ℃;
slowly dropwise adding 180g of diethyl sulfate into the iodine ion-containing solution for fractionation, keeping stirring, receiving distillate while dropwise adding, controlling the temperature of the reaction kettle within 90 ℃, and receiving 152g of distillate altogether;
and adding 20g of zeolite molecular sieve into the collected distillate, stirring for 2h, drying for 24h, filtering to obtain iodoethane, and testing by nuclear magnetic analysis that the content of the iodoethane is more than 99.9%, the water content is 96ppm, and the yield is 91.9%.
Example two
Taking 150ml of the recovered iodine ion-containing solution, filtering, and analyzing by a silver nitrate titration method to obtain the iodine ion content of 750 g/L;
adding 150ml of iodine-containing ion solution, starting stirring, and slowly heating to 70 ℃;
slowly dropwise adding 143g of diethyl sulfate into the iodine ion-containing solution for fractionation, keeping stirring, receiving distillate while dropwise adding, controlling the temperature of the reaction kettle within 90 ℃, and receiving 124g of distillate altogether;
adding 20g of UOP molecular sieve into the collected distillate, stirring for 2h, drying for 24h, filtering to obtain iodoethane, and performing nuclear magnetic analysis to test that the content of the iodoethane is more than 99.9%, the water content is 84ppm, and the yield is 90%.
The method has the advantages that the process is simple, the operation is easy, the residual liquid after the reaction can be directly disposed as hazardous waste, the diethyl sulfate is a low-toxicity substance in the use process of the raw materials, the safety risk is low, the method is suitable for realizing industrial production, the recovery rate is high, the product purity is high, and the recycling of iodide ions can be realized.
It should be noted that: the above description is only a preferred embodiment of the present invention, and is suitable for recovering various inorganic iodides or iodine ion-containing waste liquids to prepare ethyl iodide.
Claims (7)
1. A method for preparing ethyl iodide by recovering iodine ion-containing solution is characterized in that: the method comprises the following steps:
the method comprises the following steps: the recovered iodine ion-containing solution is filtered to remove large particles;
step two: adding the iodine ion-containing solution filtered in the step one into a reaction kettle, maintaining the initial temperature at 30-80 ℃, and then dropwise adding diethyl sulfate;
step three: after the dropwise adding is finished, reacting for 4 hours, slowly raising the temperature of the bottom kettle, and carrying out fractional distillation to receive a distillate product until no liquid is dripped out of the receiving bottle;
step four: and after receiving, adding a molecular sieve, standing for 24 hours, filtering to obtain ethyl iodide, and finally performing pressure filtration to a collection tank.
2. The method for preparing the iodoethane by recovering the iodine ion-containing solution as claimed in claim 1, wherein: and step one, filtering, and determining the content of iodide ions in the kettle residue by a titration method.
3. The method for preparing the iodoethane by recovering the iodine ion-containing solution as claimed in claim 1, wherein: the iodide ions of the iodine ion-containing solution are potassium iodide or magnesium iodide.
4. The method for preparing the iodoethane by recovering the iodine ion-containing solution as claimed in claim 1, wherein: and step two, slowly heating the iodine ion-containing solution to 70 ℃ under the condition of stirring, and then dropwise adding diethyl sulfate under the condition of stirring.
5. The method for preparing the iodoethane by recovering the iodine ion-containing solution as claimed in claim 1, wherein: and adding diethyl sulfate for reaction in the second step, wherein the addition molar ratio of the diethyl sulfate is as follows: iodide ion/diethyl sulfate = 1/0.5-1.4.
6. The method for preparing the iodoethane by recovering the iodine ion-containing solution as claimed in claim 1, wherein: the temperature of the reaction kettle is controlled to be 50-90 ℃.
7. The method for preparing the iodoethane by recovering the iodine ion-containing solution as claimed in claim 1, wherein: the adding amount of the molecular sieve in the step four is 1-10% of the weight of the iodoethane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111209974.7A CN113831213A (en) | 2021-10-18 | 2021-10-18 | Method for preparing ethyl iodide by recycling iodine ion-containing solution |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111209974.7A CN113831213A (en) | 2021-10-18 | 2021-10-18 | Method for preparing ethyl iodide by recycling iodine ion-containing solution |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113831213A true CN113831213A (en) | 2021-12-24 |
Family
ID=78965327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111209974.7A Pending CN113831213A (en) | 2021-10-18 | 2021-10-18 | Method for preparing ethyl iodide by recycling iodine ion-containing solution |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113831213A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB879350A (en) * | 1959-04-13 | 1961-10-11 | Gen Aniline & Film Corp | Method of manufacturing alkyl iodides |
| JP2000273057A (en) * | 1999-03-19 | 2000-10-03 | Kooriyama Kasei Kk | Production of alkyl iodide |
| CN102295519A (en) * | 2011-07-26 | 2011-12-28 | 太仓沪试试剂有限公司 | Preparation method for iodomethane |
| CN111875472A (en) * | 2020-07-23 | 2020-11-03 | 江苏南大光电材料股份有限公司 | Method for recovering methyl iodide from iodine-containing residual liquid |
-
2021
- 2021-10-18 CN CN202111209974.7A patent/CN113831213A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB879350A (en) * | 1959-04-13 | 1961-10-11 | Gen Aniline & Film Corp | Method of manufacturing alkyl iodides |
| JP2000273057A (en) * | 1999-03-19 | 2000-10-03 | Kooriyama Kasei Kk | Production of alkyl iodide |
| CN102295519A (en) * | 2011-07-26 | 2011-12-28 | 太仓沪试试剂有限公司 | Preparation method for iodomethane |
| CN111875472A (en) * | 2020-07-23 | 2020-11-03 | 江苏南大光电材料股份有限公司 | Method for recovering methyl iodide from iodine-containing residual liquid |
Non-Patent Citations (1)
| Title |
|---|
| BY S. TIETZE ET AL.: "Synthesis of I-131 labelled iodine species relevant during severe nuclear accidents in light water reactors", RADIOCHIM. ACTA, pages 1 - 6 * |
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| PB01 | Publication | ||
| PB01 | Publication | ||
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| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20211224 |
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| RJ01 | Rejection of invention patent application after publication |