2695-37-6

Basic information

• Product Name: Sodium p-styrenesulfonate
• Synonyms: p-Sodium styrenesulfonate;Sodium p-styrenesulfonate ,95%;p-Vinylbenzenesulphonic acid sodium salt hydrate, tech. 90%;Styrene sulfonate;SSS;Styrene-4-sulfonic acid sodiuM salt hydrate, tech. 90%;SodiuM p-styrenesulf;SodiuM 4-vinylbenzenesulfonate hydrate
• CAS NO: 2695-37-6
• Molecular Formula: C₈H₇O₃S*Na
• Molecular Weight: 206.19
• EINECS: 220-266-3
• Product Categories: Aromatic Esters
• Mol File: 2695-37-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 151-154 °C
• Boiling Point: 111-112 °C
• Flash Point: 78 °F
• Appearance: White/Powder
• Density: 1.043 g/mL at 25 °C
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: n20/D 1.387
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Soluble in water.
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 3575931
• CAS DataBase Reference: Sodium p-styrenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium p-styrenesulfonate(2695-37-6)
• EPA Substance Registry System: Sodium p-styrenesulfonate(2695-37-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-41-37/38-37-20/22-10
• Safety Statements: 26-36/37-36-36/37/39-39
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 3
• F: 8-23
• TSCA: Yes
• Hazardous Substances Data: 2695-37-6(Hazardous Substances Data)

Usage

Chemical Reactivity

Sodium p-styrenesulfonate (NaSS) is a functional monomer having a radical polymerizable vinyl group, a hydrophobic benzene ring having π electrons, and a sulfonic acid (salt) group that is a strong electrolyte and has been valued in various industrial fields.With the inductive effect of sulfo radical on the para position against vinyl group, sodium p-styrenesulfonate (NaSS) possesses the highest reactivity (polymerization activity) among all sulfonated vinyl monomers. It performs radical polymerization in such polar solvents as DMF, DMSO and water using common or redox polymerization initiators. For example, it has been used as a reactive emulsifier in order to improve stability of an emulsion and water resistance or cationic dye dyeability of a (emulsion) polymer.

Application

Sodium p-styrenesulfonate has been used as a reactive emulsifier in order to improve stability of an emulsion and water resistance or cationic dye dyeability of a (emulsion) polymer. Further, a polymer or a copolymer of sodium p-styrenesulfonate has been used as a dispersant for producing various aqueous dispersions of pigments, antioxidants, various polymers (tackifier resins, chloroprene rubber, polyacrylic acid esters, polyesters, styrene-butadiene copolymers, polyvinyl chloride, poly-acrylonitrile, polysilicones, conductive polymers and the like), nanocarbon materials, silica particles for hot forging release agents or abrasives, battery electrode materials (carbon, lithium iron phosphate, lithium manganese phosphate and the like), photographic silver halides and the like. Furthermore, the polymer of sodium p-styrenesulfonate has been utilized as synthetic starch for clothing finishing such as an ironing agent, a hair care product, an antistatic agent, a resist acid generator, a water treatment agent, an allergen scavenger, an ion-exchange resin, a plating solution additive, a detergent for production of semiconductors and hard disks, an additive to fluids for shale oil drilling and a flame retardant for resins.

Chemical Properties

white to light beige powder

Uses

Styrene-4-sulfonic acid sodium salt is grafted on poly(ethersulfone) membrane to determine the fractionation of proteins with similar molecular weights. It is used as sodium based ion exchange membranes for membrane capacitive deionization (MCDI) for synthesis. It is used in the study of copolymerization characteristics of sodium styrenesulfonate.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C8H8O3S/c1-2-7-3-5-8(6-4-7)12(9,10)11/h2-6H,1H2,(H,9,10,11)/p-1

Synthetic route

p-β-bromoethylbenzenesulfonic acid (54322-31-5) → sodium 4-styrenesulfonate (2695-37-6)

Conditions	Yield
With sodium hydroxide; sodium nitrite In water at 90℃; for 4h; Autoclave; Large scale;

p-β-bromoethylbenzenesulfonic acid (54322-31-5) → sodium m-styrenesulfonate + sodium 4-styrenesulfonate (2695-37-6)

Conditions	Yield
With sodium hydroxide; sodium nitrite In water at 105℃; for 1h; Inert atmosphere; Autoclave;

sodium 4-styrenesulfonate (2695-37-6) → 4-vinylbenzenesulfonyl chloride (2633-67-2)

Conditions	Yield
With thionyl chloride; 2,6-di-tert-butyl-4-methyl-phenol In N,N-dimethyl-formamide for 27h; Cooling;	100%
With thionyl chloride In N,N-dimethyl-formamide for 27h;	95%
With thionyl chloride In N,N-dimethyl-formamide; acetonitrile at 70℃; for 3h; Inert atmosphere; Cooling with ice;	82%

sodium 4-styrenesulfonate (2695-37-6) + benzyltri(n-butyl)ammonium chloride (23616-79-7) → 4-vinylbenzenesulfonic acid benzyltributylammonium salt (732306-18-2)

Conditions	Yield
In water at 20℃; for 0.0833333h;	100%
In dichloromethane; water at 20℃; for 0.5h;	99%
In dichloromethane; water	85%

1-vinyl-3-hexyl-1H-imidazol-3-ium bromide + sodium 4-styrenesulfonate (2695-37-6) → C11H19N2(1+)*C8H7O3S(1-) (1453193-88-8)

Conditions	Yield
In water at 20℃;	98%

sodium 4-styrenesulfonate (2695-37-6) + benzyltriphenylphosphonium chloride (1100-88-5) → C8H7O3S(1-)*C25H22P(1+)

Conditions	Yield
In dichloromethane; water	98%

sodium 4-styrenesulfonate (2695-37-6) + stearyl dimethyl ammonium chloride → N,N-dimethyl-n-octadecylammonium p-styrenesulfonate (155676-49-6)

Conditions	Yield
In chloroform; water for 0.5h;	97.5%

sodium 4-styrenesulfonate (2695-37-6) + (8S,9R)-(-)-N-benzylcinchonidinium chloride (69221-14-3, 69257-04-1, 95189-65-4) → N-9-benzylcinchonidinium p-styrenesulfonate (1092983-02-2)

Conditions	Yield
In dichloromethane; water	97%

sodium 4-styrenesulfonate (2695-37-6) + tetra-n-butylphosphonium chloride (2304-30-5) → tetrabutylphosphonium p-styrenesulfonate (1354745-59-7)

Conditions	Yield
In water at 20℃; for 48h;	97%
In water at 20℃; for 24h;

sodium 4-styrenesulfonate (2695-37-6) + dimethyldioctadecylammonium bromide (3700-67-2) → dioctadecyldimethylammonium p-styrenesulfonate (134291-78-4)

Conditions	Yield
In water at 70℃;	95%

sodium 4-styrenesulfonate (2695-37-6) + 1-vinyl-3-hexadecyl-3H-imidazol-1-ium bromide → C21H39N2(1+)*C8H7O3S(1-) (1453193-92-4)

Conditions	Yield
In methanol; water at 20℃;	95%

sodium 4-styrenesulfonate (2695-37-6) + tributylbenzylphosphonium chloride (1224-56-2) → C8H7O3S(1-)*C19H34P(1+)

Conditions	Yield
In dichloromethane; water	95%

tetrabutylammomium bromide (1643-19-2) + sodium 4-styrenesulfonate (2695-37-6) → tetrabutylammonium 4-vinylbenzenesulfonate (151164-21-5)

Conditions	Yield
In water; acetone at 20℃; for 6h; Inert atmosphere;	95%

1-vinyl-3-dodecyl-3H-imidazol-1-ium bromide + sodium 4-styrenesulfonate (2695-37-6) → 1-vinyl-3-dodecylimidazolium 4-styrene sulfonate

Conditions	Yield
In water at 20℃; for 24h;	94%

sodium 4-styrenesulfonate (2695-37-6) + 1-vinyl-3-octadecyl-3H-imidazol-1-ium bromide → 1-vinyl-3-octadecylimidazolium p-styrenesulphonate (1357148-55-0)

Conditions	Yield
In water at 20℃; for 48h;	91.9%
In water at 20℃; for 48h;

tetrabutyl-ammonium chloride (1112-67-0) + sodium 4-styrenesulfonate (2695-37-6) → tetrabutylammonium 4-vinylbenzenesulfonate (151164-21-5)

Conditions	Yield
In dichloromethane; water	90%

carbon dioxide (124-38-9) + sodium 4-styrenesulfonate (2695-37-6) → 4-styrene carbonate sulfonic acid sodium salt

Conditions	Yield
With N-Bromosuccinimide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene at 60℃; under 12929 Torr; for 6h; Product distribution / selectivity;	89%
With water; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; tetrabutylammomium bromide at 45 - 55℃; under 12929 Torr; for 15h; Product distribution / selectivity;	89%

sodium 4-styrenesulfonate (2695-37-6) + N-(9-anthracenylmethyl)-cinchonidinium chloride → N-9-anthracenylmethylcinchonidinium p-styrenesulfonate (1092983-04-4)

Conditions	Yield
In dichloromethane; water	89%

sodium 4-styrenesulfonate (2695-37-6) + triphenylsulfonium chloride (4270-70-6) → triphenylsulfonium 4-(vinyl)benzenesulfonate

Conditions	Yield
In water at 20℃;	83%
In water at 20℃;

sodium 4-styrenesulfonate (2695-37-6) → sodium 4-(oxiranyl)benzenesulfonate

Conditions	Yield
With D-glucose; oxygen; glucose oxidase; further reagents In phosphate buffer; water-d2 for 3h; pH=7.0; Product distribution; Further Variations:; Reagents; concentrations;	81%
With magnesium monoperoxyphthalate hexahydrate In water-d2 for 1.5h; Product distribution; Ambient temperature; add of meso-tetrakis-(4-N-methylpyridyl)porphyrinatomanganese(III) chloride, Mn(III)TPPS or CoTMPyP: efficient cat. effect; pH 6.5-6.8 (phosphate buffer); var. time.;
With Oxone; chloro(meso-tetra(4-N-methylpyridinio)porphyrinato)manganese(III)(4+) In water-d2 for 0.0333333h; Ambient temperature; pH 6.8 (phosphate buffer); Yield given;
With magnesium monoperoxyphthalate hexahydrate In water-d2 for 15h; Ambient temperature; pH 6.5 (phosphate buffer); Yield given;
With C30H24F3FeN5O(2+) In water at 25℃; pH=5.5; Kinetics; Reagent/catalyst;

Tetrapropylammonium chloride (5810-42-4) + sodium 4-styrenesulfonate (2695-37-6) → C8H7O3S(1-)*C12H28N(1+)

Conditions	Yield
In dichloromethane; water	81%

sodium 4-styrenesulfonate (2695-37-6) + 1-(4-vinylbenzyl)thymine (623563-56-4) → polymer, Mw 260 kDa, VBT/VPS ratio: 1:14; monomer(s): N1-(p-vinylbenzyl)thymine; sodium p-vinylphenylsufonate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In water; isopropyl alcohol at 65℃; for 15h;	80%

bromobenzene (108-86-1) + sodium 4-styrenesulfonate (2695-37-6) → 4-styrylphenylsulfonic acid (22692-67-7)

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In water; N,N-dimethyl-formamide at 100℃; for 2h; Heck Reaction;	80%

[(99)TcO3(tacn)](1+) (910095-44-2) + sodium 4-styrenesulfonate (2695-37-6) → (99)TcO(StyreneSO3)(tacn)

Conditions	Yield
at 95℃; for 1.5h;	78%

2-(4-hydroxy-3-methoxystyryl)-1-methylquinolinium iodide + sodium 4-styrenesulfonate (2695-37-6) → C19H18NO2(1+)*C8H7O3S(1-)

Conditions	Yield
In methanol at 20℃;	75%

ethyl bromide (74-96-4) + sodium 4-styrenesulfonate (2695-37-6) → 4-styrenesulfonate ethyl ester (16736-98-4)

Conditions	Yield
Stage #1: sodium 4-styrenesulfonate With silver nitrate In water at 0℃; for 2h; Stage #2: ethyl bromide In acetonitrile at 70℃; for 15h;	70%
With silver nitrate In water; acetonitrile at 0 - 70℃;	67%

S-difluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium tetrafluoroborate + sodium 4-styrenesulfonate (2695-37-6) → difluoromethyl 4-vinylbenzenesulfonate

Conditions	Yield
In acetonitrile at 45℃; for 72h;	67%

C24H43N2O6P + sodium 4-styrenesulfonate (2695-37-6) → C32H51N2O9PS

Conditions	Yield
With trifluoroacetic acid In water at 30℃; for 72h; Temperature; Schlenk technique; Inert atmosphere;	66%

sodium 4-styrenesulfonate (2695-37-6) + Cyclopropylamine (765-30-0) → N-cyclopropyl-4-vinylbenzenzene sulfonamide

Conditions	Yield
Stage #1: sodium 4-styrenesulfonate With thionyl chloride In N,N-dimethyl-formamide; toluene at 100℃; for 2h; Stage #2: Cyclopropylamine In dichloromethane at 20℃; for 1h;	46.2%

sodium 4-styrenesulfonate (2695-37-6) → sodium 4-(α-hydroxyethyl)benzenesulfonate

Conditions	Yield
With sulfuric acid In water for 16h; Reflux;	34%

Ni(II)dibromoporphyrin (1384190-54-8) + sodium 4-styrenesulfonate (2695-37-6) → Ni(II)di(sodium 4-phenyl sulfonate)monobenzoporphyrin

Conditions	Yield
With PPh3; Pd(OAc)2; K2CO3 In N,N-dimethyl-formamide Ni(II) dibromoporphyrin reacted with sodium 4-styrenesulfonate in DMF/xylene in presence of PPh3, Pd(OAc)2 and K2CO3; NMR, MS;	26%

sodium 4-styrenesulfonate (2695-37-6) + ethyl piperidine-2-carboxylate hydrochloride (77034-33-4) → 1-(4-vinyl-benzenesulfonyl)-piperidine-2-carboxylic acid ethyl ester

Conditions	Yield
Stage #1: sodium 4-styrenesulfonate With oxalyl dichloride In DMF (N,N-dimethyl-formamide) at 20℃; for 2.5h; Stage #2: ethyl piperidine-2-carboxylate hydrochloride With triethylamine In dichloromethane at 20℃; for 16h;	19%

Upstream product

• 54322-31-5 p-(β-bromoethyl)benzenulfonic acid 

Downstream Products

• 732306-18-2 4-vinylbenzenesulfonic acid benzyltributylammonium salt 
• 1354745-59-7 tetrabutylphosphonium p-styrenesulfonate 
• 1354745-63-3 tributylhexylphosphonium p-styrenesulfonate 
• 1365832-73-0 [⁽⁹⁹⁾TcO(OCH₂CH(C₆H₄SO₃)O)(N-benzyl-2-(1,4,7-triazononan-1-yl)acetamide)] 
• 1365832-75-2 [⁽⁹⁹⁾TcO(OCH₂CH(C₆H₄SO₃)O)(2,2',2''-(1,4,7-triazononan-1,4,7-triyl)triacetate)]^(3-) 
• 1357148-55-0 1-vinyl-3-octadecylimidazolium p-styrenesulphonate 
• 98-70-4 styrene-4-sulfonic acid 
• 1261267-89-3 C₈H₇O₃S^(1-)*C₂₄H₅₂N⁽¹⁺⁾ 
• 151164-21-5 tetrabutylammonium 4-vinylbenzenesulfonate 
• 4551-68-2 C₄H₁₂N⁽¹⁺⁾*C₈H₇O₃S^(1-) 
• 4551-88-6 4-vinylbenzene sulfonate lithium salt 
• 1161027-46-8 C₈H₇O₃S^(1-)*C₃₂H₆₈N⁽¹⁺⁾ 
• 947705-50-2 C₂₅H₄₃NO₉PS^(1-)*Na⁽¹⁺⁾ 
• 2633-67-2 4-vinylbenzenesulfonyl chloride 

Relevant articles and documents

HIGH-PURITY SODIUM P-STYRENESULFONATE WITH EXCELLENT HUE, METHOD FOR PRODUCING THE SAME, POLY (SODIUM P-STYRENESULFONATE) WITH EXCELLENT HUE USING THE SAME, AND DISPERSANT AND SYNTHETIC STARCH FOR CLOTHING FINISHING USING THE POLY ( SODIUM P-STYRENESULFONATE)

Provided are high purity sodium p-styrenesulfonate with an excellent hue which is useful as a reactive emulsifier or dispersant for producing a polymer emulsion, or synthetic starch for clothing ironing and poly(sodium p-styrene-sulfonate) with an excellent hue using the same or sodium p-styrenesulfonate improved in fluidity while keeping good solubility. An aqueous p-β-bromoethylbenzenesulfonic acid solution and an aqueous sodium hydroxide solution are reacted under specific conditions to control the particle size, thereby obtaining sodium p-styrenesulfonate particles improved in a balance between fluidity and solubility, and further, impurities such as isomers are reduced, thereby obtaining high-purity sodium p-styrenesulfonate with an excellent hue.