Di(benzothiazol-2-yl)disulfid

1.54 (NTP, 1992) - Denser than water; will sink

1.50

Density (at 20 °C): 1.5 g/cm³

PALE YELLOW NEEDLES FROM BENZENE

FREE-FLOWING POWDER

Cream to off-white powder or pellets

less than 0.1 mg/mL at 70 °F (NTP, 1992)

INSOLUBLE IN WATER; AT 25 °C LESS THAN 0.5 G/100 ML ACETONE OR BENZENE, 0.2 G/100 ML CARBON TETRACHLORIDE, 0.5 G/100 ML NAPHTHA, 0.2 G/100 ML ALCOHOL, 0.2 G/100 ML ETHER; SOMEWHAT MORE SOL IN CHLOROFORM THAN CARBON TETRACHLORIDE

In water, <10mg/L

Solubility in water: very poor

518 °F (NTP, 1992)

257 °C

334 °F (NTP, 1992)

180 °C

MP: 168 °C MIN /COMMERCIAL PRODUCT/

180 °C

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Chemical: Benzothiazole, 2,2'-dithiobis-

Benzothiazole, 2,2'-dithiobis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzothiazole, 2,2'-dithiobis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 29-09-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/14884

2,2'-Dithiobisbenzothiazole: Does not have an individual approval but may be used under an appropriate group standard

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

A skin, eye, and respiratory tract irritant; May cause skin sensitization; Can be absorbed through skin; [ICSC] May cause skin sensitization; [HSDB] A skin and eye irritant; [CAMEO] May cause skin sensitization; [eChemPortal: ESIS] May cause irritation; May cause skin and respiratory sensitization after prolonged contact; [MSDSonline] See Mercapto mix.

USEPA/OTS; Chemical Hazard Information Profile: Marcaptobenzothiazole Disulfide (MBTS) (Draft) (1983)

Grandjean E (ed); Ergonomics and Health in Modern Offices. Taylor & Francis p.1-18 (1984). Toxicological effects of office machines and material are examined. Sensitizing substances include dibenzthiazyl disulfide.

Decomposes on burning. This produces toxic and corrosive gases including carbon oxides, nitrogen oxides and sulfur oxides. Reacts with strong oxidants. This produces toxic and corrosive gases including carbon oxides, nitrogen oxides, sulfur oxides and hydrogen sulfide.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Use water spray, dry powder, foam, carbon dioxide.

Fresh air, rest.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

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.

MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS...SHOULD BE STORED IN A COOL WELL VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED...

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then dampen the solid spill material with toluene and transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene t pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with soap and water solution. All exposed surfaces should be analyzed for contamination. 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.

Personal protection: face shield and particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

TERRESTRIAL FATE: When released to soil, 2,2'-dibenzothiazyl disulfide will be categorized as immobile(3) based on estimated Koc values ranging from 10,960 to 755,000 (1,2). The rate of biodegradation in soil is probably slow (0.8% theoretical BOD in 2 weeks in an aqueous screening test using soil inoculum)(4).

AQUATIC FATE: Volatilization of 2,2'-dibenzothiazyl disulfide from water will not be an important fate process based on an estimated Henry's Law Constant of 2.34X10-13(1,2). Insufficient data are available to predict the relative importance or rate of biodegradation in aquatic conditions although one aqueous screening biodegradation test would suggest slow biodegradation(SRC). Aquatic bioconcentration factors of 1.0-7.2 and 1.4-51 for concentrations of 0.2 mg/l and 0.02 mg/l, respectively, were measured for carp(3). Since 2,2'-dibenzothiazyl disulfide absorbs light >290 nm(4), it has the potential to photolyze, alhtough the kinetics of the potential photlysis are not known(SRC). It is possible that 2,2'-dibenzothiazyl disulfide will adsorb to sediment or particulate material in an aquatic system based on its estimated Koc(SRC).

ATMOSPHERIC FATE: If released to the atmosphere, 2,2'- dibenzothiazyl disulfide will degrade in the ambient atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of 1.3 hrs(1).

Using a structure estimation method based on molecular connectivity indexes, the Koc for 2,2'-dibenzothiazyl disulfide can be estimated to be about 755,000(1). The Koc for 2,2'-dibenzothiazyl disulfide can be estimated to be about 10,960 based on an estimated water solubility of 0.187 mg/L at 25 °C and a regression derived equation(2). According to a suggested classification scheme(3), these estimated Koc values suggest that 2,2'-dibenzothiazyl disulfide is immobile in soil.

The disposition of 2-mercaptobenzothiazole disulfide (MBTS) was evaluated in male and female Fischer 344 rats ingesting [14C] MBTS via gavage at a single dose of 51.1mg/kg or 0.438mg/kg. Four animals/sex were sacrificed at 8, 24, 48, 72 and 96 hours post treatment, at which time whole blood and plasma were also collected. Urine and feces was collected at 8, 24, 48, 72 and 96 hours. The primary route of elimination of the radioactivity during the 96 hour test period was via the urine, accounting for 72.1% to 106% of the administered radioactivity. Only 4.03% to 10.3% of the administered radioactivity was excreted in the feces over the 96 hour period. A small portion of the administered radioactivity (0.432 to 2.04% of dose) remained associated with the erythrocytes. Low dose animals had a greater percentage of the dose retained in whole blood and plasma relative to the high dose animals, indicating a saturation process at the high dose level. Although tissue was not examined, it was concluded that the data did not indicate that any appreciable amount of radioactivity is retained in the tissue

The disposition of 2-mercaptobenzothiazole disulfide (MBTS) was evaluated in male and female Fischer 344 rats receiving a single intravenous dose of 0.571mg/kg. Four rats/sex were sacrificed at 5min, 15min, 1hr, 2hr, 4hr, 24hr and 72hr post treatment, at which time whole blood and plasma were also collected. For rats sacrificed at 72 hours, urine and feces were collected at 8, 24, 48 and 72 hours. The primary route of elimination of radioactivity during the 72 hour test period was via the urine, accounting for 90.9 to 101% of the administered radioactivity. Only 3.79 to 15.1% of the administered radioactivity was excreted in the feces. A small portion of the administered radioactivity (1.52 to 1.96% of the dose) remained associated with the erythrocytes. Although tissue was not examined, it was concluded that the data did not indicate that any appreciable amounts of radioactivity is retained in the tissue.

ACCELERATORS INCLUDE...BENZOTHIAZOLYL DISULFIDE... COMPD OF THIS GROUP ARE KNOWN SKIN SENSITIZERS & MAY BE PRESENT IN FINISHED RUBBERS IN TOXIC AMT.

Three contact sensitizers in rubber products, ethylbutyl thiourea (EBT), 2-mercaptobenzothiazole (MBT) and 2,2-dithio-bis-benzothiazole (MBTS), /were studied/ to relate the amount of sensitizer eliciting allergic contact dermatitis to the quantity leaching from a product into various biological fluids: normal saline, human plasma and 3 synthetic sweat solutions of pH 5.5 to 7.5. To determine the amount of sensitizer remaining after leaching, Soxhlet extraction with acetonitrile was subsequently performed. High-performance liquid chromatography was used for chemical analysis. 12 MBT-sensitive patients were patch tested with serial dilutions of MBT and MBTS ln petrolatum. A Latin Square design was used in statistical analysis of variance of the patch test results. Large amounts of thioureas leached from 2 rubber articles eliciting thiourea dermatitis, the literature suggesting that these would have been well above the elicitation threshold. Leaching of MBTS was relatively greater than MBT into most media, whereas MBT was a more potent elicitor than MBTS at equivalent concentrations. The lowest eliciting concentration of MBT in 1 subject was 0.01%. Such information should prove helpful to manufacturers in designed products that do not release allergens sufficiently to cause reactions in consumers.

Five cases of allergic contact dermatitis from rubber footwear were investigated by a combination of patch testing in patients and chemical analysis of causative rubber products. /This group of studies/ revealed 2-mercaptobenzothiazole (MBT) and benzothiazyl disulfide (MBTS) (typical allergenic accelerators) as causative chemicals in 3 cases from children's rubber shoes, ladies' rubber boots and ladies' canvas shoes. These 3 patients reacted to mercaptobenzothiazole type accelerators including MBT and MBTS. MBT and MBTS were determined in each item of causative footwear by chemical analysis including extraction by shaking with acetone-chloroform (1:1) mixture at room temperature and determination using reversed-phase high-performance liquid chromatography (R-HPLC). Subsequently, /an identification of/ styrenated phenol (SP) a newly found allergenic antioxidant as a causative chemical in a case from ladies canvas shoes. The patient reacted to SP but not to MBT and MBTS though SP, MBT and MBTS were determined in the causative shoes by gas chromatography (GC) GC-mass spectrometry (GC-MS) and HPLC. p-tert-butylphenol-formaldehyde resin (PTBP-F-R) (a known allergenic adhesive ingredient) as a causative chemical in a case from ladies sneakers /was also identified/. The patient reacted to PTBP-F-R but not to p-tert-butylphenol (PTBP), MBT and MBTS. These 4 compounds were determined in the causative sneakers by GC-MS and HPLC. /These/ studies revealed that not only known allergens such as MBT, MBTS and PTBP-F-R but also a newly found one such as SP were important causes of allergic contact dermatitis from rubber footwear.

The case of miner who developed a contact hypersensitivity to a rubber chemical Pneumax-DM (2,2 -dibenzothiazyl disulfide) present in the cable to miner's lamp is described. The examination first indicated only a positive reaction to 2-mercaptobenzothiazole, patch to the miner's suit, rubber gloves, rubber boots and the cable being negative, which followed to a decision that the illness was not occupation-related. The skin occupational disease was then confirmed by analysis of personal history and catamnesis data, clinical course, and patch of the actual allergen 2,2'-dibenzothiazyl disulfide, which induced a positive erythema infiltration vesiculous reaction. The chemical is cleaved by hydrolysis giving two molecules of 2-mercaptobenzothiazole, which also provoked a positive reaction in the patient, thus exhibiting a group cross sensitivity. ...

Using a flow-through test system, 6-week BCFs for 2,2'-dibenzothiazyl disulfide of 1.0-7.2 and 1.4-51 were measured for concentrations of 0.2 mg/L and 0.02 mg/L, respectively, for carp(1). These experimental BCF values suggest that bioconcentration in aquatic organisms is not expected to be an important fate process(SRC).

The Henry's Law constant for 2,2'-dibenzothiazyl disulfide can be estimated to be 2.34X10-13 atm-cu m/mole using a bond estimation method(1). This value of Henry's Law constant indicates that 2,2'-dibenzothiazyl disulfide is essentially non-volatile(2).

The metabolic fate of the sulfur atom in the sulfhydryl group of 2-thiobenzothiazole (TBT) metabolites was examined in a series of experiments in rats using (14)C and (35)S labeled L-cysteine and TBT metabolites. Male Wistar rats were orally administered (14)C labeled N-oxydiethylene-2-benzothiazole ODEBT, (35)S labeled ODEBT, (35)S labeled 2-mercaptobenzothiazole (MBT) and (35)S labeled 2,2'-dibenzothiazyl-disulfide (BTDS). Urine and feces were collected periodically for 72 hours and the urinary and fecal metabolites were determined. The urinary level of 2-benzothiazyl-mercapturic acid (BTMA) was determined in rats administered OCEBT orally. The incorporation of (14)C or (35)S labeled L-cysteine was determined in rats administered ODEBT orally. Glutathione conjugates of MBT from biliary metabolites were determined in rat liver in vitro. The (35)S retention ratios in BTDS and MBT was over 90%. In BTMA only 0.5% of the (35)S was retained. The ratios of conjugated to nonconjugated radioactivity obtained using (35)S labeled compounds were reduced when compared to those found for (14)C labeled compounds. Coadministration of cysteine increased the hepatic glutathione level and mercapturate excretion while inclusion of the glutathione synthetase inhibitor L-methionine-SR-sulfoximine decreased levels. The /data indicate/ that the sulfur atom in BTMA is mostly replaced by the endogenous sulfur from the cysteine pool.

6OK753033Z

2,2'-DITHIOBISBENZOTHIAZOLE

Established Pharmacologic Class [EPC] - Standardized Chemical Allergen

Physiologic Effects [PE] - Increased Histamine Release

Physiologic Effects [PE] - Cell-mediated Immunity

Chemical Structure [CS] - Allergens

To determine the metabolic disposition of (l4)C-2-mercaptobenzothiazole (MBT) and (14)C-2-mercaptobenzothiazole disulfide (MBTS) male and female rats were dosed topically. Topical doses were 36.1 ug/animal for (14)C-MBT and 33.6 ug/animal for (14)C-MBTS. Although more MBT passed through the skin than MBTS and although relative to rats, guinea pigs absorbed a greater percentage of the dose (33.4% compared to 16.1-17.5% of the MBT and 12.2% compared to 5.94-7.87% for MBTS) the disposition of radioactivity derived from the two compounds was similar. Washing of the skin removed more of the radioactivity from guinea pigs than from rats. For both sexes of rats dosed iv with (14)C-MBT 0.602 mg/kg) or (14)C-MBTS 0.571 mg/kg) disposition of the compounds was similar. In 72 hr, 90.9-101% of the dose appeared in the urine and 3.79-15.1% in the feces. At this time a small portion of the administered radioactivity (1.52-1.96% of the dose) remained associated with erythrocytes. Oral dosing of rats for 14 days with unlabeled MBT (0.510 mg/kg/day) prior to a single dose of (14)C-MBT (0.503 mg/kg) or with unlabeled MBTS (0.521 mg/kg/day) prior to a single dose of (14)C-MBTS (0.730 mg/kg). For both sexes disposition of the compounds was similar. At 96 hr after dosing a small portion of the administered radioactivity (1.20-1.69% of the dose) remained associated with erythrocytes most of which was bound to the membranes. For both compounds and sexes 60.8-101% of the radioactivity administered appeared in the urine and 3.46-9.99% in the feces in 96 hr. At the time only trace amounts of radioactivity remained in tissues other than blood. Of these tissues thyroid contained the highest concentration. In the urine there was a detectable MBT or MBTS but there were two metabolites one of which was identified as a thioglucuronide derivative of MBT. The other was possibly a sulfonic acid derivative of MBT. In conclusion there were similarities in absorption, distribution, and metabolism of (14)C-MBT and (14)C-MBTS in rats and in guinea pigs, indicating that (14)C-MBTS was readily converted to (14)C-MBT.

Used as rubber accelerator, polychloroprene plasticizer/retarder, and neoprene retarder; Also used for general mechanicals and white stocks; [HSDB] Used as cure modifier for neoprene type W and as oxidation cure activator in butyl; Used for extruded and molded products, tires, tubes, wire, cable, and sponge; [Hawley] Workers may be exposed in metals, home, health, laboratory, and building industries; [Kanerva, p. 1779]

Metal Machining [Category: Heat or Machine]

ACCELERATOR FOR NATURAL RUBBER, STYRENE-BUTADIENE RUBBER, NITRILE-BUTADIENE RUBBER; BUTADIENE RUBBER & FOR SYNTHETIC ISOPRENE RUBBER

RETARDER IN NEOPRENE

Gives flat, moderately fast curves in natural and synthetic rubber; used for general mechanicals and white stocks; plasticizer/retarder in polychloroprene.

2023: 4,000,000 - <5,500,000 lb

(1972) 9.66X10+9 GRAMS

(1975) 7.43X10+9 GRAMS

(1991) 4,419,000 kg

Rubber Product Manufacturing

Benzothiazole, 2,2'-dithiobis-: ACTIVE