Divinylsulfon

1.1788 at 68 °F (NTP, 1992) - Denser than water; will sink

1.177 g/cu cm @ 25 °C

greater than or equal to 100 mg/mL at 63 °F (NTP, 1992)

SOL IN WATER

217 °F (NTP, 1992)

217 °F

453 °F at 760 mmHg (NTP, 1992)

234.5 °C

-15 °F (NTP, 1992)

-26 °C

Divinyl sulfone is a clear colorless liquid. (NTP, 1992)

Clear colorless liquid; [CAMEO]

Danger

H300+H310 (65.8%): Fatal if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 158 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

Chemical: Ethene, 1,1'-sulfonylbis-

Divinyl sulphone: HSNO Approval: HSR004457 Approved with controls

DIVINYL SULFONE may react vigorously with strong oxidizing agents. Can react exothermically with reducing agents (such as alkali metals and hydrides) to release gaseous hydrogen or hydrogen sulfide. May react exothermically with both acids and bases. May undergo exothermic polymerization iIn the presence of various catalysts (such as acids) or initiators.

Acute Tox. 2 (99.4%)

Acute toxicity (Oral) - Category 2

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a structure estimation method(2), indicates that vinyl sulfone is expected to have very high mobility in soil(SRC). Under anaerobic conditions in soil, vinyl sulfone may be microbially reduced to the sulfide(5). Volatilization of vinyl sulfone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.9X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Vinyl sulfone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.06 mm Hg(SRC), determined from a fragment constant method(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a structure estimation method(2), indicates that vinyl sulfone is not expected to adsorb to suspended solids and sediment(SRC). Under anaerobic conditions in sediment, vinyl sulfone may be microbially reduced to the sulfide(8). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.9X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1 and 10 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -0.4(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), vinyl sulfone, which has an estimated vapor pressure of 0.06 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase vinyl sulfone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone molecules(SRC); the half-lives for these reactions in air are estimated to be 7 hours and 3 days, respectively(SRC), calculated from their rate constants of 5.3X10-11 and 3.5X10-18 cu cm/molecule-sec at 25 °C(SRC), respectively, determined using structure estimation methods(3).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for vinyl sulfone can be estimated to be 20(SRC). According to a classification scheme(2), this estimated Koc value suggests that vinyl sulfone is expected to have very high mobility in soil.

Divinyl sulfone ... can cause burns of skin & eyes similar to those from mustard gas, but divinyl sulfone differs in having no chlorine & liberating no acid. Can cause injury & enzyme inhibition by condensing with amino & other groups.

... Lacrimator ...

Vinyl sulfone's production and use during the etherization of cotton(1) may result in its release to the environment through various waste streams(SRC). The oxidation of mustard gas can result in the formation of mustard sulfone; the sulfone can further react forming vinyl sulfone(2). Therefore, vinyl sulfone may be formed during the chemical decontamination of mustard gas(2) and released during this process to the environment through various waste streams(SRC).

An estimated BCF of 3 was calculated for vinyl sulfone(SRC), using an estimated log Kow of -0.4(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

The Henry's Law constant for vinyl sulfone is estimated as 4.9X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that vinyl sulfone is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 1 day(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 10 days(SRC). Vinyl sulfone's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). Vinyl sulfone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.06 mm Hg(SRC), determined from a fragment constant method(3).

... Animal experiments show it can cause severe skin and eye burns.

... Tests on rabbit eyes have shown injuriousness graded greater than 5 on scale of 10, indicating severe burns from 0.005 ml.

A SERIES OF VINYL SULFONE MOLLUSCIDAL AGENTS WAS SHOWN TO EXHIBIT A POSITIVE CORRELATION BETWEEN SULFHYDRYL REACTIVITY & MOLLUSCICIDAL POTENCY. HIGH CONCN OF VINYL SULFONE WERE REQUIRED TO INHIBIT ACTIVITY OF MALIC DEHYDROGENASE. NO EFFECT ON ENDOGENOUS RESP OBSERVED. SIMILARLY, NO EFFECT ON ENDOGENOUS RESP OR PYRUVATE METAB WAS OBSERVED IN RATS. A SUBLETHAL DOSE OF VINYL SULFONE INCR BLOOD BUN & DECR URINARY OUTPUT WHILE PRODUCING NO EFFECT ON SGOT & SGPT ACTIVITY OR ON HEMATOCRIT VALUES IN RATS. THESE DATA INDICATE THAT THE TOXICITY OF VINYL SULFONE IS NOT RELATED TO INHIBITION OF ENDOGENOUS RESP IN EITHER SNAILS OR RATS. IT WAS POSTULATED THAT THE TOXICITY OF SUBLETHAL DOSES OF VINYL SULFONE IS CAUSED BY IMPAIRMENT OF NORMAL RENAL FUNCTION.

... The mutagenicity & clastogenicity of cmpds capable of Michael-type reactions /has been evaluated/. These cmpds, including acrylamide, several acrylate & methacrylate esters, vinyl sulfones, & phorone, have been evaluated using TK+/- -3.7.2C mouse lymphoma cells. Mutagenic chemicals induced increases in the number of small colony tk- deficient mutants. This suggested a clastogenic mechanism which was confirmed by demonstrating increases in aberrations & micronucleus frequencies in cultured cells. Vinyl sulfone was found to be the most effective chemical mutagen with induction of genotoxic effects at concns as low as 0.25 ug/ml. The other cmpds also produced positive results, but at higher concns. Since these cmpds are known to deplete glutathione, phorone, a model glutathione depleter, was examined & found to produce similar effects as the other cmpds in mouse lymphoma cells. These results suggest that the direct-acting Michael-type reaction has activity relevant to producing a genotoxic effect. Since acrylamide has been found to be a potent germ cell mutagen, this mechanism may be also relevant in the induction of heritable mutagenic risk.

For more Non-Human Toxicity Excerpts (Complete) data for VINYL SULFONE (6 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of vinyl sulfone with photochemically-produced hydroxyl radicals has been estimated as 5.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Vinyl sulfone may also react with atmospheric ozone with an estimated rate constant for this reaction of 3.5X10-18 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). Vinyl sulfone is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Vinyl sulfone may undergo direct photolysis because it absorbs light in the environmental UV spectrum(3), but the kinetics of this reaction are unknown(SRC).

Vinyl sulfone's production and use in the etherization of cotton may result in its release to the environment through various waste streams. Vinyl sulfone also may be formed during the chemical decontamination of mustard gas and released during this process to the environment through various waste streams. If released to air, an estimated vapor pressure of 0.06 mm Hg at 25 °C indicates vinyl sulfone will exist solely as a vapor in the ambient atmosphere. Vapor-phase vinyl sulfone will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone molecules; the half-lives for these reactions in air are estimated to be 7 hours and 3 days, respectively. If released to soil, vinyl sulfone is expected to have very high mobility based upon an estimated Koc of 20. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 4.9X10-5 atm-cu m/mole. Under anaerobic conditions in soil or sediment, vinyl sulfone may be microbially reduced to the sulfide. If released into water, vinyl sulfone is not expected to adsorb to suspended solids and sediment based upon the estimated Koc value. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 1 and 10 days, respectively. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to vinyl sulfone may occur through inhalation and dermal contact with this compound at workplaces where vinyl sulfone is produced or used or at locations where mustard gas is decontaminated. (SRC)

Cross-linking reagent for agarose gels; [ChemIDplus] Monomer used in manufacture of polymers with diols, urea, and malonic esters; shrinkage control agent in textiles; [Hawley]

Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

Etherization of cotton by divinyl sulfone and its precursors also forms the basis for a large class of fiber-reactive dyestuffs...

/IT/...CAN BE DERIVED FROM MUSTARD GAS.

ACIDS, ESTERS, OR ALKYLATING AGENTS WERE CROSSLINKED TO WATER-SOLUBLE POLYAMINOPOLYAMIDES TO FORM HAIR CONDITIONERS.

IN THE SYNTHESIS OF PREPN USED IN THE TREATMENT OF SEBORRHEA

Crosslinked, stroma-free hemoglobin was combined with physiological carrier, eg. vinyl sulfone, to mfr product for use as blood substitute and plasma expander for transporting oxygen to tissues. Related ref: Morris et al, US patent number 4061736, 12/6/1977 (Alza Corp)

/IT/...CAN BE DERIVED FROM MUSTARD GAS.