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Adipoyl Dichloride: Unpacking Its Industrial Journey and Future Impact

Diving Into the Past: A Chemical’s Development Story

Adipoyl dichloride has shown up in industrial chemistry with a history that follows the curve of progress in synthesis and polymer science. Its discovery dates back to the early efforts to manipulate carboxylic acids to create useful derivatives. By the time companies intentionally sought to make strong, flexible synthetic fibers like nylon, adipoyl dichloride had become almost indispensable. The timeline matches the growth of synthetic materials after World War II, with this chemical adopted as a key intermediate for stronger coatings, more durable plastics, and novel research around polyamide polymers. People sometimes overlook how much daily life changed through innovations in chemistry. Every time I zip up a weatherproof jacket or notice how light yet sturdy lab gear can be, I remember chemicals like adipoyl dichloride made that leap possible. The influence of adipoyl dichloride grew as companies realized it could anchor high-performance materials — another reminder that technological advancement doesn't just happen at the front end but often relies on the less-publicized advances in raw chemical production.

Product in Focus: Physical And Chemical Groundwork

Bring out two clear liquids in a lab, and one carries a sharp, irritating odor that tells you it’s no typical household cleaner. This is adipoyl dichloride, chemical formula C6H8Cl2O2. The molecule centers on a six-carbon backbone, making it part of the dicarboxylic acid family, but with each end "capped" by a reactive chloride. The substance floats with a density close to 1.3 g/cm³, boiling at nearly 210 °C under controlled pressure. Its reactivity defines its usefulness and its hazards—accidentally add water, and it breaks down, releasing dense clouds of hydrogen chloride. It’s not the kind of chemical you want to handle without proper protections, given its fuming and corrosive properties that can ruin glassware and burn skin on contact. Many who’ve worked in synthesis remember the pungent smell and the white mist — strong prompts to double-check goggles and work behind high-grade fume hoods. No chemist shrugs off the need for extra respect in its presence.

Technical Specs, Labeling, and Why They Matter

Over the years, detailed labeling for chemicals like adipoyl dichloride became a necessity, not just for compliance but for real safety. Regulatory bodies around the world require printed hazard statements detailing the dangers: corrosive to eyes, skin, and the respiratory tract, with risks of severe burns. Labels must highlight the need for gloves, tightly sealed goggles, and specialized ventilation—nothing left to chance. Documentation often includes the CAS number (111-50-2) and a warning to store the liquid in tightly sealed containers, away from sources of moisture. The technical side might seem distant for those outside the lab, but this standardization protects workers from some of the worst kinds of chemical injuries, and as I’ve learned, the safety sheet can be the best protection alongside practical training.

Making Adipoyl Dichloride: The Heart of the Process

Production begins with adipic acid, itself an important industrial chemical. Through the use of thionyl chloride or phosphorus pentachloride, each carboxylic acid group loses its -OH end and gains a chlorine, turning inert acid into a highly reactive diacid chloride. This isn’t just a textbook reaction; it’s a precise orchestration, requiring careful temperature management and the controlled addition of reagents to capture pure adipoyl dichloride without excess side products. Mistakes lead to hydrolysis, wasted raw materials, and workplace hazards. The robust protocols built over decades make it possible to reliably manufacture a chemical that behaves politely only under the right conditions, and that means rigorous attention to detail every step of the way.

Reactions, Modifications, and Versatility

What really drives home the importance of adipoyl dichloride is how it serves as a starting gun for building tough polymers and advanced materials. It readily reacts with diamines to form polyamides—think nylon 66, which transformed clothing, automotive parts, and even engineering design. The reactive chloride ends open doors to modifying the structure, creating crosslinked polymers or specialized copolymers with unique strengths or flexibility. Chemists push these reactions beyond basics, swapping in new reactants that respond to modern needs—faster process times, less waste, greater control over structure. Every move signals the chemical’s role as a platform for creative innovation rather than just a cog in the industrial machine.

Synonyms and Nomenclature: Clarity Amidst Complexity

Every major chemical gets a thicket of names. For adipoyl dichloride, you'll hear hexanedioyl dichloride, 1,6-hexanedicarbonyl dichloride, or just adipic acid dichloride, depending on the research paper or shipping manifest. This highlights a classic challenge in industry and research: ensuring transparent communication. In my experience, the right name at the right time saves countless hours and prevents dangerous mix-ups during ordering or handling. While it might sound like a minor paperwork detail, synonym tracking keeps global industry flowing smoothly and science clear.

Meeting Safety and Operational Standards, Not Just Checking Boxes

Day-to-day handling of adipoyl dichloride draws a firm line between safe practice and disaster. This chemical burns unprotected skin instantly and eats through some common materials, so storage calls for corrosion-resistant containers, well-ventilated chemical hoods, and a tight protocol for spill response. Regulatory bodies such as OSHA and REACH keep a close eye on exposure levels, requiring employers to train staff in the correct use of respirators and acid-resistant gloves. In honest conversations with lab colleagues, nearly everyone has a story about a close call—a cracked flask, a lick of vapor sneaking through a poorly sealed mask. These shared experiences drive home why compliance and vigilance must become habit, not afterthoughts. The cost of complacency becomes clear with every accidental squirt on a bench or forgotten glove change.

Application Zone: Industries Powered by Adipoyl Dichloride

Most people benefit from adipoyl dichloride without ever seeing or hearing about it. The biggest consumer remains the polymer industry, where it helps make nylon 66 through its direct reaction with hexamethylenediamine. These fibers shape clothing, carpeting, tire reinforcements, industrial hose, and even engine parts. Paints and coatings get a quality and durability boost from polyamides formed with this compound, leading to longer-lasting finishes and better protection against wear. Pharmaceutical industries use adipoyl dichloride in small volumes for custom molecule synthesis, opening up pathways to active ingredient development, controlled-release drug forms, and molecular scaffolds for new therapies. For engineers and materials scientists, it’s hard to overstate the enabling role that this overlooked chemical has played in making consumer goods affordable, varied, and reliable under harsh use conditions.

Innovation and Research: Looking Beyond Traditional Uses

Researchers keep coming back to adipoyl dichloride in search of materials that push past old limits. I’ve seen new research use modified forms to improve solvent resistance, mechanical strength, or biodegradability of polyamides and copolymers. Scientists blend classic reactivity with modern green chemistry—limiting hazardous byproducts and finding routes that use milder reagents. In academic labs, new functional materials emerge through creative variations on the classic acid chloride chemistry. This search doesn’t just answer commercial demands; it feeds into academic curiosity about how small tweaks at the molecular level lead to dramatic changes in performance or sustainability.

Toxicity Studies: Not Overlooked, But Instructive

Learning from the past, toxicology studies with adipoyl dichloride make clear that this isn’t a chemical for lax safety. Exposure studies identify severe risks: caustic burns, persistent respiratory irritation, and even chronic health problems after sustained or high-level exposure. Animal testing and workplace data both support the need for rigorous ventilation and personal protection. Such evidence has triggered modifications in workplace layout and equipment—sealed transfer systems, negative pressure rooms, and regular air monitoring. For me, reviewing toxicity reports always brings up a sense of urgency to advocate for ongoing attention to safety in every research or production step. Human error finds every loophole, and this chemical will exploit every one left unclosed.

Future Paths: Challenges and Promises

Looking ahead, adipoyl dichloride faces pressure to stay relevant in a chemical world demanding safer, greener, more sustainable practices. Industry shifts toward recycling, waste minimization, and alternatives with less severe hazards influence both production processes and product development. Emerging research into bio-based adipic acid creates new opportunities for “greener” dichloride routes, aiming to lower the carbon footprint while preserving the core chemistry. Some innovators are pulling polymer chemistry into the 21st century with catalysts that demand less harsh conditions or produce less waste, potentially making the old acid chloride tricks cleaner than ever. Here, I see lessons from past generations—taking established chemistry and demanding that it work with nature, not against it. The demand for stronger, lighter, more adaptable materials won’t fade, and neither will the call to make every step safer for workers and the environment.




What is Adipoyl Dichloride used for?

What Makes Adipoyl Dichloride Stand Out?

Adipoyl dichloride doesn’t get much attention outside chemical circles, but its influence runs wide. Anyone who owns something made from nylon 6,6 has benefited from this compound. Rather than being a flashy ingredient, it works quietly to make strong, long-lasting plastics. Its main claim rests with fibers and plastics that hold up to wear and high temperatures—think of car engine parts, carpet fibers, seat belts, and sports gear.

The Backbone of Nylon 6,6

Nylon 6,6 began changing manufacturing back in the 1930s, long before “performance textiles” became a buzzword. Its secret weapon lies in its structure, and that starts with adipoyl dichloride. Chemists pair this molecule with hexamethylenediamine to build nylon 6,6. The reaction produces a polymer chain that resists abrasion and stands up to solvents and heat.

Without adipoyl dichloride, the technical leap to high-strength, stretchy fibers would have taken much longer. Textiles would feel flimsier, and engine parts would give out faster. Nylon 6,6 can support heavier loads and stands up well to friction, which makes it essential in car manufacturing. According to the American Chemistry Council, the global demand for nylons remains strong, especially in Asia and North America, and adipoyl dichloride sits right at the start of this supply chain.

Beyond Nylon: Its Chemical Versatility

Industrial chemists don’t stop with fibers. Adipoyl dichloride gives them a way to build specialty plastics and coatings that need to last for years. At home, it’s rare to see a label with this chemical, but people experience its results daily—in outdoor furniture designed to last through sun and rain, or in plumbing that you can trust not to leak.

Liquid crystalline polymers, for example, also lean on this compound. These materials deliver strength at high temperatures and even in challenging chemical environments. Companies use these polymers to make medical devices or sleek, precision parts for electronics.

Safety and Environmental Discussion

Now for a real-world worry: manufacturing brings risks. Adipoyl dichloride reacts strongly with water, giving off hydrochloric acid and heat. People working with it must use personal protective equipment, install ventilation, and train carefully. Mistakes mean real danger—burns, lung problems, or environmental leaks.

Factories that handle this chemical invest in scrubber systems and double-walled piping to keep it contained. That’s not just common sense, it’s also required by environmental laws in the United States, Europe, and other developed regions. Oversight helps, but training and equipment make the real difference on the shop floor.

What Could Improve?

Leaning toward greener chemistry, researchers keep searching for safer substitutes or milder production routes. Some are looking at bio-based alternatives, although these haven’t reached commercial scale yet. Reducing waste and handling hazards could make the whole field safer and less polluting in the long run. Private and public research support both play a role here, nudging progress beyond profit motives.

For now, most of us experience adipoyl dichloride through everyday products that last longer and perform better. Knowing its story raises bigger questions about how we build the things we rely on—and how chemistry quietly shapes daily life.

What are the safety precautions for handling Adipoyl Dichloride?

Understanding the Risks

Adipoyl dichloride shows up in chemistry labs and some industrial processes — sharp, pungent, fuming. Once, early in my graduate studies, I learned the hard way that even small leaks in a fume hood matter. My colleague didn’t tighten a cap fully, and we caught the whiff before the vapor could do real harm, but our nerves learned a real lesson. Direct contact burns skin and eyes, and its vapors cause serious respiratory irritation. If water touches it, the chemical breaks down, releasing hydrochloric acid gas, so even a sweaty hand is risky. Chemical burns aren’t worth any shortcut.

The Essential Personal Gear

Before handling this chemical, I grab a full pair of splash goggles, not just safety glasses, and pull on heavy butyl rubber gloves. Nitrile gloves fail quickly here. I zip up a lab coat that covers wrists, collar buttoned tight. In case of any project that could splash, I’ll use a face shield too. I’ve seen people dismiss lab aprons as clunky, but the front of my body is less replaceable than a stained coat. For shoes, only closed-toe leather works; canvas soaks up spills.

Working Environment

Doors closed and fans running don’t stop the fumes of adipoyl dichloride. Only a well-ventilated, certified fume hood stops exposure. “Good enough” on ventilation means trouble. Once, a rushed setup in a crowded undergrad space sent vapors drifting when a bottle was opened on the bench — two students spent the afternoon with sore throats. In my own lab routine, I check the fume hood airflow indicator before even getting the bottle from storage.

Storage and Handling

The storage shelf for reactive chemicals stays cool, dry, and locked. Every bottle stands in a containment tray, away from acids, bases, or anything with water. Clear labeling saves headaches; more than once I’ve watched a misplaced bottle cause someone to scramble after nearly adding the wrong reagent to a flask. Movement between the stockroom and hood goes in a secondary container — not a hand. At the hood, I open bottles slowly, with spout pointing away, so pressure doesn’t spray a fine, invisible mist.

Dealing with Spills and Accidents

A good lab doesn’t guess at accident response. Spill kits include absorbent pads, neutralizing agents for acid and organic compounds, and bags for waste. I keep the eyewash and shower unblocked, tested weekly. Quick thinking once saved our group from serious injury: a drop splashed onto someone’s forearm, and they darted to the sink to flush the spot for 20 straight minutes. We reported to occupational health, not brushing off “just a small burn.”

Disposal the Right Way

Never pour adipoyl dichloride down the drain. Our facility traps all waste in a sealed container, clearly labeled, and the hazardous waste team removes it to an incineration service. Neutralizing with a weak base under a hood is possible only when fully trained, because hydrochloric acid gas forms quickly. Good records matter — regulators do check, but keeping your coworkers safe matters more.

Training and Staying Alert

Safety with this compound grows from experience and vigilance. Everyone working with it reads the material safety datasheet, reviews emergency steps, and never acts alone. I’ve seen confidence lead to shortcuts. The right way is slower, but everybody goes home healthy.

What is the chemical formula of Adipoyl Dichloride?

The Role of Adipoyl Dichloride in Industry

Adipoyl dichloride carries the chemical formula C6H8Cl2O2. In the hustle of daily chemical processes, this compound doesn’t always grab the headlines, but it fuels a lot of progress behind the scenes. This compound comes from adipic acid through a reaction with thionyl chloride or phosphorus pentachloride, leading to two chlorine atoms stepping in where hydroxyls once stood. The product plays a key role in synthesizing high-performance nylons, which engineers depend on for mechanical parts, car components, and clothing fibers.

Polymer manufacturing keeps turning to adipoyl dichloride for its reactivity and how quickly it joins forces with diamines in condensation reactions. Nylons like nylon 6,6 owe their backbone to these kinds of reactions, where each molecule of adipoyl dichloride links up with hexamethylene diamine, kicking out hydrochloric acid in the process. The result: strong, flexible chains that resist wear and hold their ground when stretched.

Health and Environmental Impacts

Workers handle this chemical with utmost care. Short contact with vapors irritates eyes, skin, and lungs, since it reacts quickly with moisture to give off hydrogen chloride. Reports of breathing trouble in poorly ventilated processing plants serve as a sobering reminder. Respirators, chemical gloves, and safety training are more than just regulations—they directly affect health and well-being.

Leaks and spills matter, too. Adipoyl dichloride reacts in water, forming acids that alter the pH of waterways. Fish and plants deal with the fallout. Limiting emissions makes a real difference—containment systems and dedicated treatment plants have stopped thousands of liters from reaching rivers. These steps don’t just tick boxes for compliance; they protect neighbors and whole ecosystems.

Why Accurate Formulation Matters

Mistakes at the formula stage cascade through an entire production line. An incorrect molar ratio in nylon manufacture might slow curing, lower fiber strength, or even spark within machines. Raw material traceability tightens safety, even saving money in waste reduction. In my time managing production lines, our team saw significant savings and fewer product recalls as we worked closely with suppliers and checked every incoming batch for purity and consistency. Relying on quality checks from trusted labs, we narrowed down issues to particular lots and found patterns that improved the whole operation.

Improving Safety and Efficiency

The future looks more reliable through better oversight and smarter technology. Digital tracking logs every canister and pinpoints leak sources quickly. Modern analytical tools, like chromatography and spectroscopy, highlight contamination before it sneaks into the supply chain. The company culture in many plants has shifted from finger-pointing to real-time problem solving. Supervisors lead drills, teach younger operators, and reinforce that asking questions stops trouble before it starts.

Regulators keep raising the bar, but the big push comes from the people onsite, who see how one formula—C6H8Cl2O2—branches into hundreds of real-world applications. This type of stewardship doesn’t only serve clients; it’s about leaving a safer shop floor and cleaner planet for the next person who walks in the door.

How should Adipoyl Dichloride be stored?

Not Your Average Chemical: Why Safe Storage Matters

Adipoyl dichloride packs a real punch in the chemical world. Anyone who has spent time in a university lab or a production plant knows its sharp, irritating fumes hit you long before you open the container. This chemical reacts fiercely with water; a tiny spill quickly fills the air with the choking scent of hydrochloric acid. At the first exposure, whether in school or a manufacturing job, you quickly realize how crucial proper storage becomes—not just for the person working with the chemical, but for everyone nearby.

Avoiding Moisture: The Golden Rule

Any hint of humidity nearby triggers a reaction. That’s why folks working with adipoyl dichloride keep it in tightly closed containers. Glass or high-grade plastic containers make the cut. Metal can sometimes corrode, and leaky lids invite vapor leaks and worse. Dry, well-ventilated rooms serve as the best option, far away from steam, open taps, or HVAC systems that carry unpredictable currents of moisture-laden air. In my own experience, even baggy gloves or a damp lab bench spell trouble. Don’t risk it—keep everything bone-dry.

The Importance of Ventilation and Fire Protection

I learned early in my career that a strong ventilator above the chemical storage shelves isn’t just a luxury—it saves lungs and maybe lives. Adipoyl dichloride fumes irritate eyes and breathing passages after only a modest release. Throw in a leaking cap, and the room becomes uninhabitable in minutes. Storing containers with extra space between them, away from flammable substances, limits the hazard if vapors escape. Remember, once those vapors drift around, even static electricity or a tiny flame can pose a risk.

Label Everything and Train Everyone

Clear, bold labels help everyone—from new lab assistants to the most experienced chemists. Labels with dates, hazards, and emergency contact numbers belong front and center. Training never ends, either. Every new staffer deserves a run-through of best practices before touching the stuff. I’ve watched older team members point out a near-miss simply because one bottle ended up on the wrong shelf, a reminder that even seasoned workers benefit from repeated drills and reminders.

Spill Kits and Emergency Plans

During one abrupt chemical spill in a shared lab fridge, our only safe move meant using a spill kit containing neutralizer and absorbent pads made for corrosive liquids. Quick response limited the damage to a countertop, not an entire room. Not everyone realizes that water—usually the first impulse during a spill—actually makes the situation worse. Thorough preparation includes spill response drills, storing proper personal protective equipment right at hand, and an exit plan for evacuation.

Modern Data for Modern Safety

Industry guidelines from organizations like OSHA and the European Chemicals Agency set clear limits. Chemical storage experts suggest keeping adipoyl dichloride below 25°C (77°F), shielded from direct sunlight. Safety Data Sheets recommend sites dedicated only to corrosive substances, never shared with basics or oxidizing agents. I’ve seen smart companies invest in temperature regulation alarms—whenever storage climbs a few degrees, an alert triggers a safety check. These steps don’t just check boxes on a compliance sheet: they keep workplaces running smoothly and protect everyone who steps inside.

Collaborative Safety Culture

Experience shows that safety grows as a shared responsibility, not an afterthought. Working with a chemical like adipoyl dichloride always brings risk, but treating storage protocols seriously, training every person on site, and preparing for the unexpected makes the difference. Safe storage practices save property, protect health, and build trust on the shop floor or in the lab. Experience has proven: sacrificing safety for convenience never pays off.

What are the physical and chemical properties of Adipoyl Dichloride?

Looking at Its Physical Nature

Adipoyl dichloride grabs attention right away because of its sharp, irritating smell. Anyone who's worked with this liquid knows to handle it with care, as it comes off as colorless to light yellow and doesn’t waste time irritating eyes and the nose. Pouring it out, you’ll notice it moves easily—its viscosity falls on the lighter side. It boils at around 110°C under reduced pressure, but heat makes it give off corrosive fumes, so leaving it in open containers near a source of warmth creates a real hazard.

It dissolves in many organic solvents like diethyl ether, but refuses to mix with water. Instead, it reacts right away, splitting and releasing hydrogen chloride. I remember washing out glassware and accidentally splashing it—within seconds, you get white fumes, the tell-tale sign of hydrochloric acid forming. That immediate hydrolysis is both a challenge and an advantage, depending on what you’re trying to accomplish.

Laying Out the Chemistry

On the molecular level, adipoyl dichloride stands out because of its reactivity. The two acyl chloride groups attached to a six-carbon chain allow it to participate in all sorts of condensation reactions. This is exactly why it’s so important for making nylon—hexamethylenediamine and adipoyl dichloride react to form nylon salt, pushing out hydrochloric acid as a byproduct. That release of acid isn’t just a lab curiosity; operators working in plastics environments need strong ventilation and protective gear for that very reason.

Because it reacts fiercely with water, even moisture in the air can start breaking it down. This limits how long you can store it, and how you package it. Metal cans corrode, so glass or high-grade plastics become the go-to. Also, any leak spells trouble—for both equipment and anyone in the room—since the fumes start up right away. Material safety data sheets always flag it for serious eye, skin, and respiratory harm, so handling calls for gloves, goggles, and, honestly, a good bit of respect.

Industrial and Environmental Concerns

Industries use adipoyl dichloride because it lets them make hardy polyamides and certain pharmaceuticals quickly. This isn’t a substance anyone can toss down the drain. If it gets in water, it kills aquatic life fast through sudden acidification. Labs and factories need dedicated waste treatment setups to neutralize it, and spillage calls for immediate neutralization, usually with a strong base, before cleanup crews can get to work. We all want robust materials, but trading off for environmental trouble means companies and researchers must weigh production benefits carefully.

As for improvement, replacing reagents like adipoyl dichloride with greener alternatives continues to be a priority. Some labs have begun shifting toward less corrosive coupling agents for producing polyamides, but cost and availability keep the transition slow. Until safer options arrive, real protection comes from sharp training and investment in handling infrastructure. Each bottle on a shelf reminds us that chemical progress leans on respect for risk, constant safety diligence, and the responsibility to think beyond just a successful reaction.

Adipoyl Dichloride
Adipoyl Dichloride
Adipoyl Dichloride
Names
Preferred IUPAC name hexanedioyl dichloride
Other names Adipoyl chloride
Adipic acid dichloride
Hexanedioyl dichloride
Hexanedioic acid dichloride
Pronunciation /ˌæd.ɪˈpɔɪl daɪˈklɔː.raɪd/
Identifiers
CAS Number 111-50-2
Beilstein Reference 1205743
ChEBI CHEBI:51818
ChEMBL CHEMBL141206
ChemSpider 8167
DrugBank DB14055
ECHA InfoCard 04be8ea6-8c2f-421b-a816-5824a2b16f49
EC Number 204-824-3
Gmelin Reference 7787
KEGG C14364
MeSH D006748
PubChem CID 77481
RTECS number AR9625000
UNII Q4G0I4FV9S
UN number UN 2920
CompTox Dashboard (EPA) QCATLJZUCAPFNL-UHFFFAOYSA-N
Properties
Chemical formula C6H8Cl2O2
Molar mass 183.03 g/mol
Appearance Clear colorless to pale yellow liquid
Odor Pungent
Density 1.511 g/cm3
Solubility in water Decomposes
log P 1.49
Vapor pressure 0.4 mmHg (20 °C)
Acidity (pKa) -2.8
Basicity (pKb) –3.5
Magnetic susceptibility (χ) -7.45 × 10⁻⁶ cm³/mol
Refractive index (nD) 1.451
Viscosity 2.46 mPa·s (25 °C)
Dipole moment 2.95 D
Thermochemistry
Std molar entropy (S⦵298) 354.6 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) -706.63 kJ/mol
Std enthalpy of combustion (ΔcH⦵298) -864.7 kJ/mol
Hazards
Main hazards Corrosive, causes severe burns, harmful if inhaled, reacts violently with water.
GHS labelling GHS05, GHS06
Pictograms GHS05,GHS06
Signal word Danger
Hazard statements H314: Causes severe skin burns and eye damage.
Precautionary statements P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P363, P405, P501
NFPA 704 (fire diamond) 3-2-1-W
Flash point Flash point: -1 °C
Autoignition temperature 230°C
Lethal dose or concentration LD50 oral rat 630 mg/kg
LD50 (median dose) LD50 (median dose): Oral, rat: 630 mg/kg
NIOSH SD7875000
PEL (Permissible) PEL (Permissible Exposure Limit) for Adipoyl Dichloride: Not established.
REL (Recommended) 410
IDLH (Immediate danger) 5 ppm
Related compounds
Related compounds Sebacoyl chloride
Isophthaloyl chloride
Terephthaloyl chloride