请输入您要查询的百科知识：

　

词条 Vinylsulfonic acid
释义

  1. Preparation

  2. Use

  3. Research

  4. References

{{Chembox
| ImageFile = Vinylsulfonic acid.svg
| ImageSize =
| ImageAlt =
| IUPACName = ethenesulfonic acid
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 1184-84-5
| CASNo1 = 3039-83-6
| CASNo1_Comment = (sodium salt)
| PubChem = 62474
| ChemSpiderID = 56254
| SMILES = C=CS(=O)(=O)O
| InChI = 1/C2H4O3S/c1-2-6(3,4)5/h2H,1H2,(H,3,4,5)
| InChIKey = NLVXSWCKKBEXTG-UHFFFAOYAA
| StdInChI = 1S/C2H4O3S/c1-2-6(3,4)5/h2H,1H2,(H,3,4,5)
| StdInChIKey = NLVXSWCKKBEXTG-UHFFFAOYSA-N}}
|Section2={{Chembox Properties
| C =2|H=4|O=3|S=1
| MolarMass =
| Appearance = colouless liquid
| Density =
| MeltingPt =
| BoilingPt = 128 °C (1,29 hPa)[1]
| Solubility =
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

Vinylsulfonic acid is the organosulfur compound with the formula CH2=CHSO3H. It is simplest unsaturated sulfonic acid.[2][3] The C=C double bond is a site of high reactivity. polymerize gives polyvinylsulfonic acid, especially when used as a comonomer with functionalized vinyl[4] and (meth)acrylic acid compounds.[5] It is a colorless, water-soluble liquid,[2] although commercial samples can appear yellow or even red.

Preparation

Vinylsulfonic acid is produced industrially by the alkaline hydrolysis of carbyl sulfate with subsequent acidification of the resulting vinyl sulfonate salt:[6]

The reaction is highly exothermic (reaction enthalpy: 1,675 kJ/kg) and requires exact maintenance of temperature and pH during the hydrolysis. When calcium hydroxide is used as the hydrolysis medium, a solution of calcium vinyl sulfonate is obtained. Acidification of this hydrolysis mixture with sulfuric acid gives vinylsulfonic acid, together with the poorly soluble calcium sulfate.

Vinylsulfonic acid also can be prepared by dehydration of isethionic acid with phosphorus pentoxide:[7]

Vinylsulfonic acid can also be prepared by sulfochlorination of chloroethane, dehydrohalogenation to vinylsulfonyl chloride and subsequent hydrolysis of the acid chloride.

Use

The activated C=C double bond of vinylsulfonic acid reacts readily with nucleophiles in an addition reaction. 2-Aminoethanesulfonic acid is formed with ammonia and 2-methylaminoethanesulfonic acid with methylamine.[8]

Vinylsulfonic acid is the monomer in the preparation of highly acidic or anionic homopolymers and copolymers. These polymers are used in the electronic industry as photoresists, as ion-conductive polymer electrolyte membranes (PEM) for fuel cells. For example, transparent membranes with high ion exchange capacity and proton conductivity can be produced from polyvinylsulfonic acid.[9]

Research

Vinylsulfonic acid may also be grafted to polymeric supports (e.g. polystyrene) to give highly acidic ion exchangers, which used as catalysts for esterification and Friedel-Crafts acylations.[10] Where the sulfonic acid functionality is not essential, the much more usable alkaline aqueous solution of sodium vinylsulfonate is used, which is obtained directly in the alkaline hydrolysis of the carbyl sulfate and is commercially supplied as an aqueous solution..

References

1. ^H.C. Haas, M.S. Simon: Reactivity ratios of some monomer pairs in J. Polymer Sci. 9 (1952) 309–314, {{DOI|10.1002/pol.1952.120090403}}.
2. ^1 {{cite journal|first=Kurt|last=Kosswig|title=Sulfonic Acids, Aliphatic|journal=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|year=2000|doi=10.1002/14356007.a25_503|isbn=3-527-30673-0}}
3. ^H. Distler: Zur Chemie der Vinylsulfonsäure in Angew. Chem. 77 (1965) 291–311, {{DOI|10.1002/ange.19650770704}} (PDF).
4. ^{{Cite patent | country = EP | number = 0643081 | title = Polymers of vinylsulfonic acid | A-Datum = | gdate = 1995-03-15 | invent1 =H. Hoffmann et al. | assign1 =Hoechst AG }}
5. ^{{Cite patent | country = US | number = 2011017954 | title =VINYL SULFONIC ACID, POLYMER THEREOF, AND PRODUCTION METHOD THEREOF | A-Datum = | gdate =2011-01-27 | invent1 =H. Akikaze et al. | assign1 = }}
6. ^{{Cite patent | country = US | number = 3872165 | Typ = Erteilung | title = Manufacture of vinyl sulfonates and vinylsulfonic acid from carbylsulfate | A-Datum = 1971-11-30 | gdate = 1975-03-18 | invent1 = Roland Dahlinger, Walter Schenk, Dieter Stockburger | assign1 = BASF | DB = Google}}
7. ^{{Cite patent | country = US | number = 2597696 | Typ = Erteilung | title = Preparation of Ethylenesulfonic acid | A-Datum = 1948-03-18 | gdate = 1952-05-20 | invent1 = J.A. Anthes, J.R. Dudley | assign1 = American Cyanamid | DB = Google}}
8. ^{{cite journal |author = H. Distler | title = Zur Chemie der Vinylsulfonsäure | work = Angewandte Chemie | volume = 77 | date = 1965-04-07| number = 7| pages = 291–302| DOI= 10.1002/ange.19650770704}}
9. ^{{citation|surname1=Teruyuki Okayasu, Toshiyasu Hibino, Hiroyuki Nishide|periodical=Macromolecular Chemistry and Physics|title=Free Radical Polymerization Kinetics of Vinylsulfonic Acid and Highly Acidic Properties of its Polymer|volume=212|issue=10|year=|pages=1072–1079|date= 17 May 2011|doi=10.1002/macp.201000773|url=http://libgen.io/scimag/get.php?doi=10.1002/macp.201000773}}
10. ^T. Okayasu, K. Saito, H. Nishide, M.T W. Hearn: Poly(vinylsulfonic acid)-grafted solid catalysts: new materials for acid-catalysed organic synthetic reactions. In: Green Chem. 12 (2010) 1981–1989, {{DOI|10.1039/C0GC00241K}}.

3 : Sulfonic acids|Monomers|Vinyl compounds
随便看

　

开放百科全书收录14589846条英语、德语、日语等多语种百科知识，基本涵盖了大多数领域的百科知识，是一部内容自由、开放的电子版国际百科全书。

　

Copyright © 2023 OENC.NET All Rights Reserved
京ICP备2021023879号 更新时间：2024/9/20 16:45:28