Dibutyl Disulfide: Deep Dive into a Crucial Chemical
Historical Development
Dibutyl disulfide has turned up in both industrial and academic work since the twentieth century, tracing its relevance back to early organosulfur chemistry explorations. Researchers in the mid-1900s often ran into it while studying the degradation of biological materials and the flavor science lurking within onions and garlic. Industry picked it up not just for curiosity but for its role as a specialty solvent, lubricant additive, and process chemical. Over decades, newer synthesis routes and cleaner production standards replaced the hazy, old-school methods full of impurities and laborious separations, which played their role in chemistry classrooms and manufacturing plants alike.
Product Overview
Dibutyl disulfide stands out as a pale yellow liquid with a strong, distinctive odor that most workers in fine chemicals never mistake. Chemists label it as an organosulfur compound—its backbone sits on two butyl chains linked by a disulfide bond. If you flip through safety data sheets, you'll quickly see its industrial-grade presence stretches to pharmaceutical intermediates, flavors, fragrances, solvents, and sometimes, the rubber industry. Some catalogues also flag it for use as a chemical intermediate for more complex molecules, hinting at its value in synthetic organic chemistry and catalysis studies.
Physical & Chemical Properties
A look at its properties reveals a liquid above room temperature, with a boiling point often close to 230°C and a melting point that dips below freezing. In practical work, the density lands around 0.9 g/cm³. It shows poor solubility in water, preferring organic solvents, and its vapor is heavier than air. Many chemists keep in mind its volatility and aggressive sulfur aroma—both serve as natural reminders of potential hazards during transfers and extractions. This characteristic smell, partly what gives unrefined petroleum its punch, makes detection of leaks almost foolproof.
Technical Specifications & Labeling
A typical technical sheet lists purity above 98%, with clear specification of sulfur-content, water content, and color by APHA standards. Certificates often include GC traces showing the absence of secondary disulfides and side-chain sulfides. In warehouse and laboratory labeling, the chemical grabs several red flags: corrosive, flammable, toxic by inhalation—a background that forces strict compliance under global transport (UN 2381), hazard pictograms, and GHS language. Batch numbers, manufacturer details, and reaction suitability form the backbone of responsible tracking, echoing the increasing demands for traceability and accountability in the chemical supply chain.
Preparation Method
Traditional manufacturers react n-butyl mercaptan with oxidizing agents such as hydrogen peroxide or iodine under controlled conditions. Batch or continuous reactors maintain temperature and agitation, balancing complete reaction with minimal side product formation. Years ago, perchlorates and chromates cropped up, but sharper environmental rules now steer choices toward milder, greener oxidizers. Downstream, separation steps include distillation under reduced pressure, washing with brine, and neutralization to polish up the purity for industrial and research use. By controlling stoichiometry and time, experienced process technicians prevent overoxidation into more robust disulfoxides and sulfones, avoiding wasted material and expensive remediation.
Chemical Reactions & Modifications
Dibutyl disulfide reacts with a host of nucleophiles and reducing agents. Catalytic hydrogenation breaks it down to n-butyl mercaptan, and exposure to strong bases cleaves the disulfide bond, sometimes leading down the path toward thioethers and further sulfurized compounds. Chemists use it to introduce disulfide bridges, or shuffle sulfur atoms in synthesis, shaping molecular architecture for target molecules in pharmaceuticals or specialty chemicals. Exposure to halogens can oxidize it further or split it into mixed disulfides, giving synthetic chemists versatile tools for manipulating sulfur chemistry—the practical backbone for many innovations in agriculture, materials, and energy storage.
Synonyms & Product Names
Dissecting catalogs and labeling standards reveals a spectrum of names: n-Butyl disulfide, Didibutyl disulfide, 1-Butyl disulfide, DBDS, and the ever-cryptic CAS number 629-45-8. Some trade names tease at regional branding, while others simply reflect the systematic nomenclature. Industry and research both lean heavily on shorthand—DBDS pops up everywhere, especially when searching through patents, chemical inventory records, or toxicity databases.
Safety & Operational Standards
Handling dibutyl disulfide pushes safety to the front. Workers soon notice its toxic vapor, which irritates lungs and eyes with surprising speed. Companies require local exhaust, chemical splash goggles, nitrile gloves, and rigorous personal monitoring. Spills call for absorbents matched to sulfur compounds—regular cloths and paper won’t cut it. Fire risk jumps whenever containers stay near open flames or hot machinery. Companies bundle standard GHS labeling with workplace training to drive home the danger, and trusted suppliers issue updated safety data sheets as soon as regulatory changes occur. No shortcut replaces proper ventilation, routine leak checks, or responsible waste disposal—lessons learned from years spent in crowded, fume-filled synthesis labs.
Application Area
Dibutyl disulfide finds its way into lubrication, corrosion protection, organic synthesis, and electronics. Lubricant formulators value its ability to form protective layers on metal surfaces, prolonging machinery lifespan in automotive and industrial settings. Rubber industry chemists use it for vulcanization modifications that toughen tires and industrial belts. Its sulfur trust plays out in agrochemical precursor manufacture, and fragrance designers chase the complex aroma profile for more authentic notes in synthetic garlic, onion, and truffle flavors. Some companies blend it into cable insulation formulations to ward off copper corrosion, especially in high-voltage power infrastructure. Academic researchers and process chemists also value DBDS’s versatility as both a reactant and a chemical probe for disulfide shuffling in bioorganic synthesis and new polymer research.
Research & Development
Over the last decade, R&D focus has shifted toward greener, more selective synthesis routes and alternative applications. Teams experiment with catalyst-based systems for disulfide bond formation, hoping to sharpen selectivity and slash environmental impact. There’s also heavy interest in recycling strategies for sulfur-rich waste streams, aiming for circular chemistry that turns unavoidable byproducts into useful organosulfur chemicals like dibutyl disulfide. Instrument developers have designed new sensors based on DBDS detection for oil and gas pipelines, since its presence tracks equipment aging and elemental sulfur contamination—both threats to downtime and repair budgets.
Toxicity Research
Toxicologists dig deep into dibutyl disulfide’s impact on living systems. Inhalation studies on rodents point to acute toxicity at high levels, largely because sulfur vapors irritate and inflame respiratory tissues. Repeated, long-term exposure risks liver, kidney, and nervous system effects. Occupational health records indicate that those working consistently around DBDS must undergo respiratory health monitoring and medical checkups. People with sulfite sensitivity report headaches, nausea, or asthmatic symptoms even at trace exposures, which drew regulatory attention from both workplace safety agencies and environmental groups. The increasing data pool now helps regulators set more precise exposure limits and inform emergency response guides.
Future Prospects
Looking at the horizon, dibutyl disulfide will likely hold ground in niche industrial and scientific applications. The shift toward greener chemistry sparks more demand for alternatives to heavy-metal catalysts, giving DBDS a bigger role as a “transformer” molecule for advanced synthesis and biomimetic chemistry. Startups dig into using sulfur-based compounds for safer battery electrolytes and high-durability polymers, and dibutyl disulfide becomes a logical tool for those pushing into uncharted territory. As the chemical sector tightens sustainability targets, more efficient synthesis, lower-emission handling, and smarter reuse of sulfur sources promise to reshape the lifecycle of DBDS.
What People Use Dibutyl Disulfide For
Dibutyl disulfide can sound like some fancy oddball chemical, but it’s more common in industry than most realize. This yellowish liquid shows up in lubricant manufacturing, as well as oil and gas drilling fluids. That oily, pungent smell usually means you're dealing with a sulfur compound, and dibutyl disulfide fits right in. It delivers strong sulfur content, which many refineries and oilfield teams want for managing metal parts and heavy loads.
That sulfur comes in handy for cutting oils and extreme pressure lubricants. Sulfur-based additives help reduce wear on tools and machinery, keeping engines or equipment going during tough jobs. In my own experience with shop repairs and farm equipment, these kinds of additives really make the difference between smooth operation and clunky breakdowns. Lubricants with sulfur stick around on moving parts longer than other oils. It keeps friction and heat down inside engines and gearboxes.
Down-to-Earth Applications
Beyond the basics, mining companies use dibutyl disulfide for extracting precious metals using flotation processes. Chemicals like this react with mineral surfaces to help separate out copper, gold, and other metals from everything else. It’s kind of like oiling a rusty lock: the right chemical can get stuff working smoothly and efficiently, but in this case, it makes the minerals stick just where you want them during separation.
Dibutyl disulfide also finds its way into making specialty chemicals. It acts as a building block for creating flavors, fragrances, or agricultural products where the sulfur content gives a strong base for different reactions. Even though that might sound like a small corner, small differences at the chemical level can make a big impact on crop yields or flavor profiles in food chemistry.
Risks, Realities, and Responsible Use
This chemical is far from harmless. Work crews and lab technicians have to handle it with care due to health risks. Just one whiff can trigger headaches, nausea, or worse, if exposure runs high. There have been plenty of workplace incidents where improper ventilation or handling caused problems. Long-term exposure raises concerns around lungs and skin, with some evidence suggesting ongoing irritation and potential long-term health effects. Rules for proper personal protective equipment and air handling haven’t come out of nowhere—they come from hard-learned lessons.
Environmental risks run alongside worker safety. Dibutyl disulfide doesn’t break down easily if it gets loose in water or soil. That sharp, rotting cabbage odor signals that nature doesn’t absorb these kinds of substances quietly. Industrial spills can linger if cleanup doesn’t happen right away, adding stress to river systems and farmland. I remember one local river cleanup tied to a chemical spill—it took months to get things back (mostly) to normal, with wildlife slow to return.
Managing Industry Needs Fairly and Safely
A lot comes down to what safeguards get put in place. Companies that focus on training, monitoring air quality, and reviewing their chemical handling see far fewer issues. Where cost-cutting shortcuts win out, health and environmental problems rack up fast. Regulators and watchdog groups help by setting limits and testing water and air near big users. Community reporting—sometimes just neighbors comparing odd smells—often catches leaks before official channels do.
Switching to safer alternatives isn’t as easy as swapping out one ingredient, but research keeps moving on creating additives and flotation agents with less toxic side effects. Every old-school chemical carries some risk, so clear communication and fast response matter every bit as much as the technical details.
From Lab Benches to Daily Life
Dibutyl disulfide isn’t some far-off chemical tucked away in a niche laboratory. It crops up in chemical plants, industrial settings, and even in ongoing conversations about workplace safety or environmental monitoring. The formula—C8H18S2—might look simple, but the way those atoms connect creates a chemical with plenty of personality.
Breaking Down C8H18S2
I still remember mixing up organic compounds in college labs, where the smallest change—a swapped-out carbon, a new bond—could transform clear liquid into a stinky, volatile mess. Here, we've got eight carbons, eighteen hydrogens, and two sulfurs. Each butyl chain (that’s four carbons, nine hydrogens) links up on either end of a sulfur-sulfur bridge. This double-sulfur feature gives dibutyl disulfide its punchy odor and reactive nature. You know it's in the room—even tiny amounts leave no doubt.
Handling and Hazards
Smell isn’t the only story. With chemicals like C8H18S2, safety jumps front and center. Breathing in vapors over long shifts can lead to headaches or irritation. Research points out that these disulfide compounds, especially in poorly ventilated spaces, ramp up health concerns for industrial workers. Strong odor doesn’t equal toxicity, but it should signal respect for protective equipment and safe handling rules.
Industry Uses
Dibutyl disulfide plays a role in petroleum refining, where sulfur-based chemicals pop up as byproducts and process additives. Oil refineries turn to it for desulfurization steps, stripping out contaminants that would otherwise poison catalysts or harm engines. Maybe you’ve never set foot in a refinery, but if you rely on clean-burning fuels or care about reduced exhaust emissions, that chemistry makes ripples in your life.
Sulfur Compounds and Environmental Questions
These disulfide types don’t just disappear once used. Some enter the air or wastewater streams. Environmental scientists flag them as part of the broader sulfur pollution puzzle. Odor complaints around plants often trace back to disulfide leaks. Routine monitoring and better containment go a long way, but community engagement offers even more. Living near chemical industry zones, I’ve seen how quick reporting of smells and health symptoms helps regulators identify and address problems sooner, keeping neighborhoods safer.
Improving Practices
Safer alternatives sometimes step in, but cost or process compatibility still holds many companies to what works. As green chemistry gains steam, research pushes for less hazardous sulfur process agents—either by changing solvents or capturing more volatile emissions at the source. On the ground, regular checks, smart sensor placement, and better communication lines between workers, residents, and plant managers show promise. I’ve watched local groups become vital watchdogs, holding operators accountable for environmental and health impacts.
Why Formula Knowledge Counts
Understanding that dibutyl disulfide fits the formula C8H18S2 isn’t just trivia. A clear grasp of its structure opens doors to recognizing its risks, knowing where it appears, and choosing smarter responses—whether at work, in policy, or simply reading the label on an industrial product. Chemistry isn’t distant. It lands on real lives, workplaces, and neighborhoods every day.
What Happens With Dibutyl Disulfide?
Dibutyl disulfide pops up mainly in chemical manufacturing, sometimes in petroleum refining or as an additive in lubricants. The strong sulfur smell hits the nose right away. That alone signals the body to be cautious. Anyone who’s worked around chemicals knows safety isn’t just paperwork—it’s personal protection backed by hard evidence.
Health and Safety Risks
Breathe in even small amounts, and irritation quickly follows. The eyes water, the throat starts to burn, sometimes the skin gets itchy or turns red. Higher concentrations lead to headaches, dizziness, or nausea. If it stays on the skin long enough, it can cause blisters. OSHA and NIOSH both list dibutyl disulfide on their hazard sheets, flagging it as a chemical worth real attention, not just a passing glance.
Everyday experience in a lab or near industrial tanks teaches that assumptions get people hurt. NIOSH rates dibutyl disulfide’s exposure limit at 0.5 ppm over an eight-hour workday. That low number sticks out for a reason: chronic exposure may result in longer-term problems with the liver, nervous system, or lungs. Rats and other test subjects don’t fare well with repeated inhalation, showing tissue damage after weeks of exposure.
Environmental Hazards
Letting dibutyl disulfide seep away means passing the problem on to rivers, soil, and anyone downstream. Small spills harm aquatic life. Fish and invertebrates face toxic effects, and once environmental damage begins, reversing it gets expensive and complicated. The EPA flags this compound for careful handling and controlled disposal. Anyone dumping or mishandling it, knowingly or not, faces fines—or worse, lawsuits over contaminated land or water.
Handling and Prevention
Having worked with industrial chemicals, I’ve seen the difference that clear rules and working equipment make. Ventilation isn’t optional. Good gloves, proper goggles, a working respirator—all stand between a safe shift and an emergency call. Lab coats and eye washes save skin and save sight. On-site safety training sometimes gets treated as a box-check, yet it turns practical after one close call with a spill.
Lab managers and plant supervisors must ensure proper labeling and storage. Storing dibutyl disulfide away from open flames and oxidizers reduces accident risks. Regular audits and maintenance of equipment stop leaks before they start. Working with knowledgeable staff, rather than untrained labor, lowers the odds of mistakes.
Looking at Safer Alternatives
No one enjoys the idea of risking health for a chemical that might have alternatives. Newer lubricants and additives come on the market every year, some with better toxicity profiles. Companies who make the switch not only reduce liability but build trust with employees and local communities. Switching isn’t always cheap or easy, but the long-term savings—from less worker illness to fewer fines—often outweigh short-term costs.
Final Thoughts
Dibutyl disulfide doesn’t belong in the same category as everyday household risks. Its hazards aren’t theoretical; real people have landed in clinics and emergency rooms after mishandling it. Respecting the risks, investing in training, and considering safer options matter every day.
Understanding What’s At Stake
Dibutyl Disulfide carries a pungent odor, even at low concentrations, that makes it a challenge for anyone managing warehouses or manufacturing plants. It doesn’t take much to notice a spill or a leaky drum—this chemical can turn a quiet facility into a tough environment fast. Staff working with this material often recall their first encounter by smell alone, a reminder that just ignoring best practices isn’t an option.
Keeping It Contained
A good rule for Dibutyl Disulfide is always respect the volatility. It can react with strong oxidizers, which puts safety at the top of the list for anyone storing it. Tanks, drums, and containers should come made from materials like stainless steel or high-density polyethylene that hold up against corrosion. Folks who skimp on quality containers will face repairs, unexpected leaks, and complaints from anyone working nearby.
Proper sealing matters—vented caps keep pressure from building up but stop vapors from escaping into the work area. Drips and splashes mean trouble for both workflow and health. Separate out Dibutyl Disulfide from acids, bleaching agents, and other reactive chemicals. I’ve seen facilities pay heavily for mixing this one in the wrong space—a single mixing error can shut down operations for days due to contamination and cleanup.
Temperature, Ventilation, and Safety Measures
Room temperature storage works, but don’t let things get too warm. High heat speeds up vapor release. Good ventilation pays big dividends in lowering fumes—open-air storage or powerful exhaust fans create a safer workday for everyone. Never toss drums in direct sunlight or next to steam lines if you want to avoid those phone calls from panicked safety teams. Every time those mistakes happen, complaints start rolling in and productivity tanks.
Spills often lead to rapid evacuations—quick response plans should always be in place. Absorbent materials that resist chemical breakdown, like clay-based granules, help stop spread and make cleanup less dangerous. Regular training sessions on spill kits and eye wash stations go a long way—nobody thinks they need it, until the day it happens.
Health Hazards and Worker Protection
Dibutyl Disulfide vapors don’t just smell bad—they can irritate the eyes, skin, and lungs, sometimes immediately. Anyone handling open containers or pumps should use gloves, chemical splash goggles, and, where ventilation runs short, a respirator fitted for organic vapors. Clean work clothes and regular rotation out of odor-heavy areas cut down on worker fatigue and health complaints. Regulations from OSHA and similar agencies set clear limits, but companies that go beyond minimums usually see better staff retention and fewer accidents.
What Makes a Good Policy?
On-site management isn’t just about rules on paper. Regular inspections, digital inventory logs that flag expiring products, and transparent communication with nearby teams help everyone keep an eye on the material. It adds a personal layer to safety, something I saw firsthand in facilities that encouraged anyone to speak up about leaks or smells—no matter their role. Companies with open lines rarely get caught off guard.
Outside audits by industrial hygienists offer fresh perspective and can catch overlooked issues. Improvement isn’t just a checklist—it comes from feedback from the people who move, mix, and monitor every day. Respecting that hands-on experience avoids problems and keeps operations running smoothly.
Understanding Dibutyl Disulfide
Dibutyl disulfide appears as a yellowish liquid, often with a pungent, sulfur-like odor that never fails to hit the nose hard on first encounter. This chemical flows with an oily texture, slipping past the skin and stubbornly clinging if spilled. Anyone who’s handled industrial chemicals knows just how pervasive that sulfur smell can get, sticking to clothing long after the work is done. Its boiling point hovers around 231°C, so it sticks around as a liquid in most lab and plant environments, even under heat. Dibutyl disulfide’s molecular structure allows it to dissolve well in many organic solvents, but it shuns water. Try to wash it away, and it floats, barely mixing—something best remembered when thinking about clean-up or containment.
Reactivity and Stability
Chemists notice right away that the bonds holding the two sulfur atoms together react strongly under certain conditions. Add strong acids or bases, and this disulfide might break apart, releasing unpleasant-smelling compounds and, sometimes, posing a risk of toxic fumes. The reactivity with metal surfaces or strong oxidizers can make storage a matter of real attention. Containers with a tight seal, along with good ventilation in the area, protect not just the product but the workers around it. Leaks tend to leave behind a lingering signature—once that smell sneaks into a workspace, it doesn’t let go until every trace disappears. So, work with care becomes more than a guideline. It’s basic common sense in any lab or factory using it.
Common Uses and Workplace Hazards
People use dibutyl disulfide in a handful of industries. Refineries and specialty chemical producers rely on it as a sulfurizing agent, especially in making lubricant additives and rubber chemicals. Some folks in research play with its structure to study how sulfur compounds interact, or to create flavors and fragrances—though the notion of adding that scent to anything edible seems wild to most folks outside the lab. What often gets overlooked is its toxicity. Direct skin contact can cause irritation, and breathing fumes can spark headaches or breathing issues. On a factory floor, you don’t want anyone ignoring a spill or breathing in its fumes just because it isn’t a household name. Good training, effective fume hoods, gloves, and goggles matter.
Environmental and Health Considerations
Because dibutyl disulfide doesn’t mix with water, spills threaten local waterways and soil instead of dissolving away. Wildlife can’t just “process” it, so contamination lingers, and the heavy odor tips off anyone nearby long before any scientific test. Environmental crews often rely on absorbent materials to soak up contamination, followed by careful disposal. People who live or work near factories handling this chemical sometimes worry about long-term effects, citing studies that link chronic exposure to potential nervous system effects and longer-lasting respiratory problems.
Working Toward Fewer Risks
The chemical industry keeps working on improved process containment and personal protective equipment. Regular safety drills and spill response plans help keep risk in check. Digital monitoring and tighter storage policy tightened exposure limits, cutting down on careless mistakes. Plant managers who spend real time on the floor spot problems early, listening to those who know the routines and know what happens when corners get cut. That’s where the biggest gains in safety show up. Teaching everyone on site about the peculiarities of each substance, down to how to spot even faint traces of that telltale odor, keeps people safer and the environment cleaner. No one wants a legacy of neglect in their town or workspace, so more folks in chemical-heavy industries are embracing transparency around hazardous materials.
| Names | |
| Preferred IUPAC name | bis(butylsulfanyl)methane |
| Other names |
Dibutylbisulfide
Dibutyl disulphide Bis(n-butyl) disulfide n-Butyl disulfide |
| Pronunciation | /daɪˈbjuːtɪl daɪˈsʌlfaɪd/ |
| Identifiers | |
| CAS Number | 629-45-8 |
| 3D model (JSmol) | ``` C(CCSC(=S)SCC)(CC)SC(=S)SCC ``` |
| Beilstein Reference | 1721247 |
| ChEBI | CHEBI:51453 |
| ChEMBL | CHEMBL154198 |
| ChemSpider | 5326 |
| DrugBank | DB11424 |
| ECHA InfoCard | 03b71de8-51b3-4019-bd3a-2b88501c5dcd |
| EC Number | 203-729-4 |
| Gmelin Reference | 77830 |
| KEGG | C08227 |
| MeSH | D003978 |
| PubChem CID | 8189 |
| RTECS number | KN5250000 |
| UNII | 66C261P0R6 |
| UN number | UN2347 |
| Properties | |
| Chemical formula | C8H18S2 |
| Molar mass | 178.36 g/mol |
| Appearance | Pale yellow liquid |
| Odor | Unpleasant, garlic-like |
| Density | 0.918 g/mL at 25 °C |
| Solubility in water | Insoluble |
| log P | 2.82 |
| Vapor pressure | 0.27 mmHg (25°C) |
| Acidity (pKa) | ~10.6 |
| Magnetic susceptibility (χ) | -65.9×10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.527 |
| Viscosity | 1.44 mPa·s (25 °C) |
| Dipole moment | 0.19 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 233.6 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -121.6 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -2487 kJ/mol |
| Hazards | |
| GHS labelling | GHS02, GHS07, GHS09 |
| Pictograms | GHS02,GHS07,GHS09 |
| Signal word | Warning |
| Hazard statements | H226, H302, H315, H319, H335, H400 |
| Precautionary statements | P210, P261, P273, P305+P351+P338, P304+P340, P501 |
| NFPA 704 (fire diamond) | 1-2-2-W |
| Flash point | 90°C |
| Autoignition temperature | 180 °C |
| Explosive limits | 1.1–7.5% (in air) |
| Lethal dose or concentration | ATE (oral, rat): 2600 mg/kg |
| LD50 (median dose) | LD50 (median dose): Rat oral 260 mg/kg |
| NIOSH | UN2203 |
| PEL (Permissible) | PEL: 0.5 ppm (as sulfur) |
| REL (Recommended) | REL (Recommended Exposure Limit) of Dibutyl Disulfide is "0.5 ppm (3 mg/m³) TWA |
| IDLH (Immediate danger) | 100 ppm |
| Related compounds | |
| Related compounds |
Diethyl disulfide
Dimethyl disulfide Dipropyl disulfide Di-tert-butyl disulfide |
