CN102746200A - Synthesis method of alkyl disulfonate - Google Patents
Synthesis method of alkyl disulfonate Download PDFInfo
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- CN102746200A CN102746200A CN2012102497293A CN201210249729A CN102746200A CN 102746200 A CN102746200 A CN 102746200A CN 2012102497293 A CN2012102497293 A CN 2012102497293A CN 201210249729 A CN201210249729 A CN 201210249729A CN 102746200 A CN102746200 A CN 102746200A
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- alkyl
- disulfonic acid
- disulfonate
- orthoformate
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Abstract
The invention provides a synthesis method of alkyl disulfonate. Alkyldisulfonic acid and trialkyl ortho-formate react to obtain the alkyl disulfonate, wherein the trialkyl ortho-formate is used as both a reaction reagent and a reaction solvent. The invention has the advantages of accessible raw materials and short reaction time, and is simple to operate. The alkyl disulfonate can be used as a lithium battery electrolyte additive to prolong the cycle life of the lithium battery.
Description
Technical field
The present invention relates to the organic synthesis field, particularly relate to a kind of compound method of alkyl disulfonate.At length say alkyl disulfonic acid and alkyl orthoformate are reacted, obtain the alkyl disulfonate.
Background technology
The alkyl disulfonate has widely to be used, and very high industrial application value is arranged.The alkyl disulfonate can be used as a kind of pharmacological agent reagent and uses; The alkyl disulfonate can also use as the lithium-ion battery electrolytes additive in addition, improves the cycle life of lithium cell.
About the compound method of alkyl disulfonate, bibliographical information less.The alkyl disulfonate can't react to such an extent that method prepares with alkyl disulfonic acid and pure direct esterification.In J. American Pharmaceutical Association, reported a kind of method; This method is earlier with methane-disulfonic acid and silver carbonate reaction synthesizing methane disulfonic acid silver; Then with methane-disulfonic acid silver and iodomethane reaction synthesizing methane disulfonic acid dimethyl ester; This method has been used expensive silver carbonate and methyl iodide, certainly will cause production cost high.In J.Am.Chem.Soc., mentioned a kind of method, ethane disulfonic acid and olefine reaction synthesize the ethane disulfonic acid verivate, then carry out the synthetic ethane disulfonic acid diethyl ester of pyrolysis, and this method difficulty or ease control and yield are low.
Do not have a kind of good method to produce the alkyl disulfonate in the industry at present, this has also influenced applying of alkyl disulfonate.
Given this, the invention provides a kind of method of the condition synthesis of alkyl disulfonate in gentleness, this method adopts alkyl disulfonic acid and alkyl orthoformate to react; One step obtained the alkyl disulfonate; This method raw material is easy to get, and cost is low, is easy to realize suitability for industrialized production.
Summary of the invention
The object of the present invention is to provide a kind of compound method of alkyl disulfonate.
Alkyl disulfonate of the present invention is methane-disulfonic acid dimethyl ester, methane-disulfonic acid diethyl ester, ethane disulfonic acid dimethyl ester, ethane disulfonic acid diethyl ester.
The method of synthesis of alkyl disulfonate of the present invention is that alkyl disulfonic acid and alkyl orthoformate are reacted under the condition of gentleness, obtains corresponding alkyl disulfonate.
The method of synthesis of alkyl disulfonate of the present invention, the alkyl disulfonic acid comprises methane-disulfonic acid, ethane disulfonic acid.
The method of synthesis of alkyl disulfonate of the present invention, alkyl orthoformate comprise trimethyl orthoformate, triethyl orthoformate.
The method of synthesis of alkyl disulfonate of the present invention, need not to add other solvent can accomplish.
The method of synthesis of alkyl disulfonate of the present invention, alkyl orthoformate also as reaction solvent, can through distillatory method reclaim excessive alkyl orthoformate after reaction finishes both as reaction reagent.
The method of synthesis of alkyl disulfonate of the present invention has only by products such as methyl-formiate, ethyl formate, methyl alcohol, ethanol to generate in reaction process, is easy to separate with product.
The present invention adopts following technical scheme.
The method of synthesis of alkyl disulfonate of the present invention is that alkyl disulfonic acid and alkyl orthoformate are reacted under the condition of gentleness, obtains corresponding alkyl disulfonate.
In alkyl disulfonate synthetic; The alkyl disulfonic acid comprises methane-disulfonic acid, ethane disulfonic acid; The alkyl disulfonic acid contains the crystal water or the easy moisture absorption usually; If contain the crystal water or the moisture absorption, can adopt known method to remove crystal water and contained moisture, such processing is favourable to the reaction of back.
In alkyl disulfonate synthetic, alkyl orthoformate comprises trimethyl orthoformate, triethyl orthoformate, and alkyl orthoformate is both as reaction reagent, also as reaction solvent.
In alkyl disulfonate synthetic, the mol ratio of alkyl disulfonic acid and alkyl orthoformate is 1:2～1:10, does not have special qualification.
In alkyl disulfonate synthetic, order of addition(of ingredients) has no particular limits, and alkyl disulfonic acid and alkyl orthoformate can disposablely add; Also can add the alkyl disulfonic acid earlier, drip alkyl orthoformate then; Also can add alkyl orthoformate earlier, add the alkyl disulfonic acid then in batches.
In alkyl disulfonate synthetic, temperature of reaction is 0～100 ℃, and temperature of reaction is not had special qualification.
In alkyl disulfonate synthetic, the reaction times there is not special qualification, the reaction times is 0.5～10h.
In alkyl disulfonate synthetic, reaction can take the separation known purification process to obtain required alkyl disulfonate product after finishing.
Embodiment
Through specific embodiment the present invention is done further description below, but the present invention not only is defined in these instances.
Embodiment 1
In the 500ml flask of electric mixer, TM, spherical condensation tube is housed, successively add 88g methane-disulfonic acid, 250g trimethyl orthoformate, then at 60 ℃ with interior stirring reaction 5h.After reaction finishes, distill out the methyl alcohol, methyl-formiate and the excessive trimethyl orthoformate that generate in the reaction, the residual methane-disulfonic acid dimethyl ester that promptly obtains.
Embodiment 2
In the 500ml flask of electric mixer, TM, constant pressure funnel, spherical condensation tube is housed; Add the 95g ethane disulfonic acid earlier; Then through constant pressure funnel at 2h with interior droppings 300g trimethyl orthoformate, drip to finish afterwards at 80 ℃ with interior continuation stirring reaction 5h.After reaction finishes, distill out the methyl alcohol, methyl-formiate and the excessive trimethyl orthoformate that generate in the reaction, the residual ethane disulfonic acid dimethyl ester that promptly obtains.
Embodiment 3
In the 2000ml flask of electric mixer, TM, spherical condensation tube is housed, successively add 200g ethane disulfonic acid, 740g triethyl orthoformate, then reaction mass at 80 ℃ with interior continuous stirring reaction 7h.After reaction finishes, adopt the method for normal pressure or decompression to distill out ethanol, ethyl formate and the excessive triethyl orthoformate that generates in the reaction, the residual ethane disulfonic acid diethyl ester that promptly obtains.
Embodiment 4
In the 1000ml flask of electric mixer, TM, constant pressure funnel, spherical condensation tube is housed, add earlier the 180g methane-disulfonic acid, Dropwise 5 00g triethyl orthoformate in 2h then, then at 70 ℃ with interior continuation stirring reaction 4h.After reaction finishes, distill out the ethanol, ethyl formate and the excessive triethyl orthoformate that generate in the reaction, the residual methane-disulfonic acid diethyl ester that promptly obtains.
Claims (5)
1. the compound method of an alkyl disulfonate is characterized in that: alkyl disulfonic acid and alkyl orthoformate are reacted, obtain the alkyl disulfonate.
2. the compound method of alkyl disulfonate as claimed in claim 1 is characterized in that: described alkyl disulfonic acid is methane-disulfonic acid or ethane disulfonic acid.
3. the compound method of alkyl disulfonate as claimed in claim 1 is characterized in that: described alkyl orthoformate is trimethyl orthoformate or triethyl orthoformate.
4. like the compound method of claim 1 and 3 described alkyl disulfonates, it is characterized in that: described alkyl orthoformate is a reaction reagent, also is reaction solvent.
5. the compound method of alkyl disulfonate as claimed in claim 1 is characterized in that: the mol ratio of described alkyl disulfonic acid and alkyl orthoformate is 1:2～1:10.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012102497293A CN102746200A (en) | 2012-07-18 | 2012-07-18 | Synthesis method of alkyl disulfonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012102497293A CN102746200A (en) | 2012-07-18 | 2012-07-18 | Synthesis method of alkyl disulfonate |
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| CN102746200A true CN102746200A (en) | 2012-10-24 |
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| CN2012102497293A Pending CN102746200A (en) | 2012-07-18 | 2012-07-18 | Synthesis method of alkyl disulfonate |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115650949A (en) * | 2022-09-08 | 2023-01-31 | 深圳市瑞禾新材科技有限公司 | Preparation method of methylene methanedisulfonate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2928859A (en) * | 1958-06-23 | 1960-03-15 | Chemstrand Corp | Alkylation of acids with alkyl orthocarboxylates |
| US20070117945A1 (en) * | 2005-11-11 | 2007-05-24 | Canon Kabushiki Kaisha | Novel polymer, charge control agent, and toner for developing electrostatic latent images |
-
2012
- 2012-07-18 CN CN2012102497293A patent/CN102746200A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2928859A (en) * | 1958-06-23 | 1960-03-15 | Chemstrand Corp | Alkylation of acids with alkyl orthocarboxylates |
| US20070117945A1 (en) * | 2005-11-11 | 2007-05-24 | Canon Kabushiki Kaisha | Novel polymer, charge control agent, and toner for developing electrostatic latent images |
Non-Patent Citations (3)
| Title |
|---|
| A. A.PADMAPRIYA等: ""A New Method for the Esterification of Sulfonic Acids"", 《SYNTHETIC COMMUNICATIONS》 * |
| JOHN I. TRUJILLO等: ""Facile Esterification of Sulfonic Acids and Carboxylic Acids with Triethylorthoacetate"", 《TETRAHEDRON LETTERS》 * |
| MANABU HATANO等: ""Synthesis of chiral 3,3’-disubstituted 1,1’-binaphthyl-2,2’-disulfonic acids"", 《TETRAHEDRON: ASYMMETRY》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115650949A (en) * | 2022-09-08 | 2023-01-31 | 深圳市瑞禾新材科技有限公司 | Preparation method of methylene methanedisulfonate |
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Application publication date: 20121024 |