CN114907306B - Method for removing organic bromine in organic solvent - Google Patents
Method for removing organic bromine in organic solvent Download PDFInfo
- Publication number
- CN114907306B CN114907306B CN202111048389.3A CN202111048389A CN114907306B CN 114907306 B CN114907306 B CN 114907306B CN 202111048389 A CN202111048389 A CN 202111048389A CN 114907306 B CN114907306 B CN 114907306B
- Authority
- CN
- China
- Prior art keywords
- bromine
- organic
- carbonate
- organic solvent
- ethylene glycol
- 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.)
- Active
Links
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 title claims abstract description 74
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 229910052794 bromium Inorganic materials 0.000 title claims abstract description 74
- 239000003960 organic solvent Substances 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 185
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 23
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical group OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000012535 impurity Substances 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 44
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 30
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 22
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 15
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 abstract description 7
- 230000008901 benefit Effects 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 39
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 238000009775 high-speed stirring Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000852 hydrogen donor Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000007256 debromination reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000012263 liquid product Substances 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
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002957 persistent organic pollutant Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
- C07D317/38—Ethylene carbonate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/08—Purification; Separation; Stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of chemical industry, in particular to a method for removing organic bromine in an organic solvent. The invention comprises the following steps: and (3) carrying out contact reaction on an organic solvent containing organic bromine as an impurity and an ethylene glycol solution of carbonate to convert the organic bromine into inorganic bromine, wherein the organic bromine is 2-bromoethanol. According to the invention, the nucleophilic substitution reaction is carried out on the organic bromine and the ethylene glycol solution under the condition of high-temperature stirring, so that the organic bromine is converted into inorganic bromine, and the inorganic bromine can further react with carbonate to promote forward progress of the nucleophilic substitution reaction, so that a better removal effect can be obtained, and meanwhile, the method has the advantages of simple operation steps, mild reaction conditions and better market prospect.
Description
Technical Field
The invention relates to the technical field of chemical industry, in particular to a method for removing organic bromine in an organic solvent.
Background
At present, in the organic chemical production process of bromine-containing catalysts, organic bromine is often generated, so that the quality of products is affected, and organic bromide is a global emerging persistent organic pollutant which is a great concern after organic chloride.
In an invention patent (CN 201910343003.8) of a method for measuring the total organic bromine content by catalytic reduction debromination, a method for generating active hydrogen atoms by utilizing a hydrogen donor to react with a catalyst and reducing organic bromine into inorganic bromine through the active hydrogen atoms is disclosed, and the method has excessively complicated operation steps, and meanwhile, the hydrogen donor and the catalyst need to be provided, so that the purification cost is increased, and the method is unfavorable for large-scale purification.
In an invention patent (cn2015139203. X) of an analysis method of the contents of organic and inorganic chlorine in a reforming catalyst, a method of eluting chloride ions by alkaline hydrolysis is disclosed, but the method is not suitable for the removal of organic bromine because the organic bromine causes serious corrosion to equipment when converted into inorganic bromine in an aqueous environment. Thus, there is a need to develop a process for converting organic bromine to inorganic bromine in an anhydrous system.
Disclosure of Invention
In order to solve the technical problems, the invention provides a method for removing organic bromine in an organic solvent, which is used for converting the organic bromine into inorganic bromine by nucleophilic substitution reaction of the organic bromine and a glycol solution under the condition of high-temperature stirring, so as to realize the conversion of the organic bromine into the inorganic bromine under an anhydrous system.
The invention provides a method for removing organic bromine in an organic solvent, which comprises the following steps: and (3) carrying out contact reaction on an organic solvent containing organic bromine as an impurity and an ethylene glycol solution of carbonate to convert the organic bromine into inorganic bromine, wherein the organic bromine is 2-bromoethanol.
In certain embodiments of the present invention, the organic solvent comprises one or more of ethylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate.
Of course, it should be noted that, for the selection of the organic solvent, it is necessary to ensure that Br groups in the organic bromine are more easily removed than those contained in the organic solvent during the contact reaction, and, at the same time, for the mixed organic solvent, it is also necessary to ensure that the main component of the mixed organic solvent differs from the boiling point of ethylene glycol by more than 30 ℃ in order to avoid that the organic solvent and/or the main component of the organic solvent forms an azeotrope with the ethylene glycol, which is disadvantageous for the subsequent removal of ethylene glycol.
In certain embodiments of the invention, the ethylene glycol solution of carbonate is a ethylene glycol solution of potassium carbonate and/or a ethylene glycol solution of sodium carbonate.
In certain embodiments of the present invention, the ethylene glycol solution of potassium carbonate is formulated into an ethylene glycol solution of 10% to 30% by mass potassium carbonate, and the ethylene glycol solution of sodium carbonate is formulated into an ethylene glycol solution of 5% to 8% by mass sodium carbonate.
In certain embodiments of the invention, the mass ratio of the potassium carbonate and/or sodium carbonate to the organic bromine is 1:100 to 1:10.
In certain embodiments of the present invention, the organic bromine is contained in the organic solvent in an amount of 100ppm to 20000ppm.
In certain embodiments of the present invention, the temperature at which the organic solvent containing organic bromine is contacted with the ethylene glycol solution of carbonate is 80-100 ℃. Too low a reaction temperature (below 80 ℃) results in low reaction rate and long time consumption, too high a reaction temperature (above 100 ℃) not only consumes high energy but also causes volatilization of the low-boiling organic solvent, and the related side reactions are correspondingly increased, such as acceleration of hydrolysis of ethylene carbonate, etc.
In certain embodiments of the present invention, the organic solvent containing the impurity organic bromine is contacted with the ethylene glycol solution of carbonate for a reaction time of 4 to 8 hours.
In certain embodiments of the present invention, the contacting reaction of the organic solvent containing the contaminant organic bromine with the ethylene glycol solution of carbonate further comprises stirring, particularly high speed stirring. The high-speed stirring is used for uniformly mixing the organic solvent containing the organic bromine with the ethylene glycol solution of the carbonate, so as to promote the forward progress of the reaction.
In certain embodiments of the present invention, the contact reaction of the organic solvent containing the organic bromine impurity with the ethylene glycol solution of carbonate further comprises cooling, filtering and rectifying separation. This is because, as the reaction time increases, ethylene glycol in the ethylene glycol solution of carbonate is continuously consumed, inorganic salts such as carbonate are precipitated, the carbonate precipitated from the ethylene glycol solution and other inorganic salts produced by the reaction are removed by cooling and filtration, and the purpose of rectification is to obtain the organic solvent from which organic bromine is removed.
Compared with the prior art, the invention has the following advantages:
the invention provides a method for removing organic bromine in an organic solvent, which is characterized in that nucleophilic substitution reaction is carried out on the organic bromine and glycol solution under the contact reaction, so that the organic bromine is converted into inorganic bromine, and the inorganic bromine can be further reacted with carbonate to promote forward progress of the nucleophilic substitution reaction, so that a better removing effect can be obtained, and meanwhile, the method is simple in operation steps, mild in reaction conditions and better in market prospect.
Detailed Description
The following description of the embodiments of the present invention will clearly and completely describe the technical solutions of the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to fall within the scope of the invention.
The reaction principle of the contact reaction of the organic solvent containing organic bromine and the ethylene glycol solution of carbonate in the invention is as follows: (taking ethylene glycol solution of Potassium carbonate as an example)
HBr+K 2 CO 3 ＝KBr+KHCO 3 (2)
Wherein, br atom belongs to easy leaving group, and because of the induction effect, the C atom connected with Br atom is positively charged, and at the same time, O atom on glycol hydroxyl has lone electron pair, so that whole glycol can attack C+ connected with Br atom as nucleophilic reagent, finally glycol loses H+ and Br-as leaving group to combine into HBr, potassium carbonate can react with generated HBr to promote forward progress of reaction (1).
Preparation of ethylene glycol solution for carbonate
Ethylene glycol solution of 10% potassium carbonate: 10g of potassium carbonate was weighed out and dissolved in 90g of ethylene glycol.
Ethylene glycol solution of 20% potassium carbonate: 20g of potassium carbonate was weighed and dissolved in 80g of ethylene glycol.
Ethylene glycol solution of 30% potassium carbonate: 30g of potassium carbonate was weighed and dissolved in 70g of ethylene glycol.
Ethylene glycol solution of 5% sodium carbonate: 5g of sodium carbonate was weighed out and dissolved in 95g of ethylene glycol.
Ethylene glycol solution of 6% sodium carbonate: 6g of sodium carbonate are weighed out and dissolved in 94g of ethylene glycol.
Ethylene glycol solution of 8% sodium carbonate: 8g of sodium carbonate was weighed out and dissolved in 92g of ethylene glycol.
Method for measuring organic bromine in (II) organic solvent
Gas chromatography
Sampling: and taking a liquid sample obtained by cooling, filtering and rectifying separation after the reaction.
The operation is as follows: (1) Respectively preparing standard solutions of organic bromine and organic solvents;
(2) Respectively sampling the standard solutions to obtain standard curves;
(3) And sampling the sampled liquid sample, and correcting by using the standard curve to obtain a test result.
The present invention will be further described in detail by way of examples, but the present invention is not limited thereto.
Example 1
The ethylene carbonate contained 1000ppm of 2-bromoethanol.
Ethylene glycol solution containing 1000ppm of 2-bromoethanol and 10% of potassium carbonate is added into ethylene glycol solution containing 1000ppm of 2-bromoethanol, the mixture is stirred at a high speed for 4 hours at the temperature of 80 ℃, and after cooling, filtering and rectifying, the obtained test results of 2-bromoethanol in the ethylene carbonate are filled in Table 1.
Examples 2 to 3
As shown in Table 1, the ethylene glycol solutions having the potassium carbonate contents shown in examples 2 to 3 of Table 1 were added, and the test results of 2-bromoethanol in the ethylene carbonate obtained in the same manner as in example 1 were filled in Table 1.
Example 4
Ethylene carbonate contained 3600ppm of 2-bromoethanol.
Ethylene glycol solution containing 3600ppm of 2-bromoethanol and 10% potassium carbonate is added into ethylene glycol solution, the mixture is stirred at a high speed for 6 hours at 90 ℃, and after cooling, filtering and rectifying, the test results of 2-bromoethanol in the ethylene carbonate are filled in Table 1.
Examples 5 to 6
As shown in Table 1, the ethylene glycol solutions having the potassium carbonate contents shown in examples 5 to 6 of Table 1 were added, and the test results of 2-bromoethanol in the ethylene carbonate obtained were the same as those of example 4, and the results are shown in Table 1.
Example 7
The ethylene carbonate contained 20000ppm of 2-bromoethanol.
Ethylene glycol solution containing 10% of 10% potassium carbonate is added into 20000ppm of ethylene carbonate containing 2-bromoethanol, the mixture is stirred at a high speed for 8 hours at a temperature of 100 ℃, and after cooling, filtering and rectifying, the test results of the 2-bromoethanol in the ethylene carbonate are filled in Table 1.
Examples 8 to 9
As shown in Table 1, the ethylene glycol solutions having the potassium carbonate contents shown in examples 8 to 9 of Table 1 were added, and the test results of 2-bromoethanol in the ethylene carbonate obtained were the same as those of example 7, and the results are shown in Table 1.
TABLE 1
Examples 10 to 12
Examples 10-12 include most of the operating steps of example 1, except that:
the organic solvent containing 2-bromoethanol before the reaction was the organic solvents shown in examples 10 to 12 in Table 2, and the test results of 2-bromoethanol in the organic solvents shown after the reaction were obtained in the same manner as in example 1, and were filled in Table 2.
TABLE 2
Examples 13 to 15
Examples 13-15 include most of the procedures described in example 1, except that: the ethylene glycol solution of potassium carbonate was replaced with the ethylene glycol solution of sodium carbonate, and the ethylene glycol solution of sodium carbonate content shown in examples 13 to 15 in Table 3 was added, and the test results of 2-bromoethanol in the ethylene carbonate obtained were filled in Table 3.
TABLE 3 Table 3
According to the method for removing the organic bromine in the organic solvent, nucleophilic substitution reaction is carried out on the organic bromine and the glycol solution under the condition of high-temperature stirring, so that the organic bromine is converted into inorganic bromine, and the inorganic bromine can further react with carbonate to promote forward progress of the nucleophilic substitution reaction. Cooling, filtering and rectifying separation are usually required after the reaction to obtain a purified organic solvent, wherein the cooling, filtering are used for removing carbonate remained in the reaction and other inorganic salts generated by the reaction, and the rectifying separation is used for separating the organic solvent from other liquid products generated in the reaction to obtain the purified organic solvent.
The invention has been further described with reference to specific embodiments, but it should be understood that the detailed description is not to be construed as limiting the spirit and scope of the invention, but rather as providing those skilled in the art with the benefit of this disclosure with the benefit of their various modifications to the described embodiments.
Claims (8)
1. A method for removing organic bromine from an organic solvent, comprising: the method comprises the steps of (1) carrying out contact reaction on an organic solvent containing organic bromine as an impurity and ethylene glycol solution of carbonate to convert the organic bromine into inorganic bromine, wherein the organic bromine is 2-bromoethanol;
the Br group in the organic bromine is easier to leave than the Br group contained in the organic solvent, and the main component of the organic solvent and the boiling point of ethylene glycol differ by more than 30 ℃;
the ethylene glycol solution of the carbonate is the ethylene glycol solution of potassium carbonate and/or the ethylene glycol solution of sodium carbonate; the mass concentration of the ethylene glycol solution of the potassium carbonate is 10% -30%, and the mass concentration of the ethylene glycol solution of the sodium carbonate is 5% -8%.
2. The method for removing organic bromine from organic solvent according to claim 1 wherein: the organic solvent comprises one or more of ethylene carbonate, dimethyl carbonate, diethyl carbonate and methyl ethyl carbonate.
3. The method for removing organic bromine from organic solvent according to claim 1 wherein: the mass ratio of the potassium carbonate and/or sodium carbonate to the organic bromine is 1:100-1:10.
4. The method for removing organic bromine from organic solvent according to claim 1 wherein: the content of the organic bromine in the organic solvent is 100ppm-20000ppm.
5. The method for removing organic bromine from organic solvent according to claim 1 wherein: the temperature of the contact reaction of the organic solvent containing organic bromine and the ethylene glycol solution of carbonate is 80-100 ℃.
6. The method for removing organic bromine from organic solvent according to claim 1 wherein: the time for the contact reaction of the organic solvent containing organic bromine and the ethylene glycol solution of carbonate is 4-8 hours.
7. The method for removing organic bromine from organic solvent according to claim 1 wherein: the contact reaction of the organic solvent containing organic bromine and the ethylene glycol solution of carbonate also comprises stirring.
8. The method for removing organic bromine in organic solvent according to any one of claims 5 to 7 wherein: the contact reaction of the organic solvent containing organic bromine and the ethylene glycol solution of carbonate further comprises cooling, filtering and rectifying separation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111048389.3A CN114907306B (en) | 2021-09-08 | 2021-09-08 | Method for removing organic bromine in organic solvent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111048389.3A CN114907306B (en) | 2021-09-08 | 2021-09-08 | Method for removing organic bromine in organic solvent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114907306A CN114907306A (en) | 2022-08-16 |
| CN114907306B true CN114907306B (en) | 2024-03-15 |
Family
ID=82760707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111048389.3A Active CN114907306B (en) | 2021-09-08 | 2021-09-08 | Method for removing organic bromine in organic solvent |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114907306B (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5962699A (en) * | 1998-07-23 | 1999-10-05 | Huntsman Petrochemical Corporation | Process for decolorizing organic carbonates |
| JP2002193892A (en) * | 2000-12-28 | 2002-07-10 | Ube Ind Ltd | Method for producing high-purity carbonate |
| CN105218509A (en) * | 2015-07-12 | 2016-01-06 | 九江学院 | The minimizing technology of ethylene glycol in a kind of NSC 11801 |
| CN105732566A (en) * | 2014-12-12 | 2016-07-06 | 中国石油天然气股份有限公司 | Method of producing ethylene carbonate |
| TW201827395A (en) * | 2016-12-28 | 2018-08-01 | 荷蘭商蜆殼國際研究所 | A method of treating a carbonate stream |
| CN109081310A (en) * | 2018-10-26 | 2018-12-25 | 山东省海洋化工科学研究院 | A method of extracting bromine from brominated feed liquid or waste water |
| CN110817901A (en) * | 2019-12-03 | 2020-02-21 | 广东飞南资源利用股份有限公司 | Bromine fixation process for waste plate and bromine recovery process for waste plate |
-
2021
- 2021-09-08 CN CN202111048389.3A patent/CN114907306B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5962699A (en) * | 1998-07-23 | 1999-10-05 | Huntsman Petrochemical Corporation | Process for decolorizing organic carbonates |
| JP2002193892A (en) * | 2000-12-28 | 2002-07-10 | Ube Ind Ltd | Method for producing high-purity carbonate |
| CN105732566A (en) * | 2014-12-12 | 2016-07-06 | 中国石油天然气股份有限公司 | Method of producing ethylene carbonate |
| CN105218509A (en) * | 2015-07-12 | 2016-01-06 | 九江学院 | The minimizing technology of ethylene glycol in a kind of NSC 11801 |
| TW201827395A (en) * | 2016-12-28 | 2018-08-01 | 荷蘭商蜆殼國際研究所 | A method of treating a carbonate stream |
| CN109081310A (en) * | 2018-10-26 | 2018-12-25 | 山东省海洋化工科学研究院 | A method of extracting bromine from brominated feed liquid or waste water |
| CN110817901A (en) * | 2019-12-03 | 2020-02-21 | 广东飞南资源利用股份有限公司 | Bromine fixation process for waste plate and bromine recovery process for waste plate |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114907306A (en) | 2022-08-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101274750B (en) | Tail gas-recycled sulfur recovery method | |
| EP2738861B1 (en) | Method for producing lithium tetrafluoroborate solution | |
| US6866689B2 (en) | Aqueous borohydride compositions | |
| CN102125851B (en) | Application method of waste copper based catalyst to preparing catalyst for preparing hydrogen from methanol | |
| WO2010061838A1 (en) | Hydrogen fluoride purification method | |
| EP0198971B1 (en) | Process for purification of silane and analysis of contaminants therein | |
| CN1227839A (en) | Process for low-pressure synthesis of dimethyl carbonate by carbon monoxide | |
| CN113321587B (en) | Preparation method of adamantyl trimethyl ammonium hydroxide and quaternary ammonium base aqueous solution prepared by preparation method | |
| CN114907306B (en) | Method for removing organic bromine in organic solvent | |
| WO2024008206A1 (en) | Preparation method for lithium difluorophosphate | |
| CN101597275B (en) | Method for purifying fluoroethylene carbonate | |
| CN102492845A (en) | Method for digesting spent rhodium catalyst in carbonyl group synthetic reaction | |
| CN115215292A (en) | Method for preparing hydrogen by using secondary aluminum ash | |
| CN113634274B (en) | Method for efficiently decomposing hydrogen peroxide by graphene-coated cobalt catalyst under acidic condition | |
| CN114990586A (en) | Preparation process of adamantyl trimethyl ammonium hydroxide and quaternary ammonium base aqueous solution prepared by preparation process | |
| WO2022015717A1 (en) | Improved alkali metal cyanide production | |
| CN112473742A (en) | Desulfurization catalyst for simultaneously removing hydrogen sulfide and carbonyl sulfide and preparation method thereof | |
| CN112875730B (en) | Purification method of nuclear pure lithium fluoride | |
| CN116836147B (en) | Preparation method and application of cyclic sulfate | |
| CN1296410C (en) | Process for preparing doped conductive polyaniline | |
| CN110407224B (en) | Modified vanadium-silicon molecular sieve, preparation method and application thereof, and thioether oxidation method | |
| CN116143079B (en) | Method and device for purifying HIx phase of thermochemical sulfur-iodine cyclic hydrogen production | |
| CN112573565A (en) | Method for preparing potassium stannate trihydrate by using tin stripping waste liquid | |
| CN115367938A (en) | Treatment system and treatment method for waste alkali liquor generated by extracting trioxymethylene | |
| CN109111424B (en) | Method for recovering sulfolene crystallization wastewater |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |