Chemists first synthesized diethyl maleate during the late 1800s, tapping into the growing field of organic synthesis that shaped modern carbon chemistry. At the time, researchers were keen on transforming simple molecules into compounds with functional uses, and diethyl maleate, as a dialkyl ester of maleic acid, stood out due to its reactivity. With the advent of more precise distillation and purification methods, its production quickly became scalable by the early 20th century, feeding into both experimental research and early industrial needs. War-time shortages often shifted the focus towards homegrown feedstocks, encouraging improved synthesis from fumaric acid and ethylene. By the 1960s, demand from the plastics, coatings, and additives sector had anchored diethyl maleate as a staple in fine chemicals and materials science, laying out a groundwork for more advanced applications to emerge in biochemical research and specialty manufacturing.
Diethyl maleate carries a straightforward structure: two ethyl groups attached to the trans form of maleic acid. This set-up gives the molecule an accessible double bond, making it a cornerstone reactant for Michael additions and related transformations. Its clarity and slight odor fit well within established industrial protocols. The product goes into packaging meant for stability, often sold as a yellowish liquid or a more refined colorless variant for electronics-grade use. Existing demand arises from its utility as an intermediate, and plenty of chemists depend on reliable suppliers for meeting regulatory and logistical lines required by current large-scale production.
This ester melts at around −65°C and boils close to 229°C. With a moderate vapor pressure at room temperature, diethyl maleate does not tend to evaporate quickly, which helps during processing. It dissolves in alcohols and ethers but holds minimal solubility in water, a trait that points to easy recovery from washing steps. Its double bond attracts nucleophiles and radicals, readily entering Diels-Alder, Michael, and transesterification reactions. These properties place practical handling above mere theoretical interest; in my experience, labs appreciate its manageable volatility and chemical behavior that helps tailor small-molecule and polymer designs for engineered properties.
When purchased as a raw material, diethyl maleate comes labeled with its purity—usually 98% or higher for most commercial uses. Proper labeling includes hazard symbols indicating potential health risks: eye irritation, possible respiratory issues, and the need for gloves and goggles during handling. Laboratories and warehouses must keep containers sealed and shaded from direct light, with date of manufacture and lot number for traceability. Meeting such documentation standards allows audits and regulatory checks to run smoothly and backs up claims during product recalls or incident reviews. Careful handling proves no small matter; even seasoned workers appreciate a product whose labeling points them to clear industry norms.
Large-scale producers rely on a well-established esterification route: maleic anhydride reacts with ethanol in the presence of a small acid catalyst load, producing diethyl maleate alongside water. Once the mixture settles, separation of the aqueous and organic layers follows, using distillation at reduced pressure to concentrate and purify the ester. Some facilities introduce azeotropic removal of water to drive the reaction forward. Energy efficiency and waste minimization count during each stage, and changes in catalyst selection or feed purity give unique fingerprints to plant-specific materials. Research teams keep iterating on ways to lower energy costs and push selectivity upwards, especially when pursuing greener chemistry approaches.
In synthesis, diethyl maleate draws strong interest as a Michael acceptor. The molecule teams up with nucleophiles such as amines or thiols to produce fine-tuned adducts. Use in Diels-Alder cycloadditions brings new ring systems to life, aiding pharmaceutical and agrochemical research. On the surface of polymers, its double bond welcomes cross-linking and surface modification, improving adhesion or reactivity. Reactive blending with hydrogels or elastomers pushes the compound into emerging fields such as soft robotics and medical devices. Downstream, chemists introduce additional functional groups by hydrogenation or hydrolysis, opening up a swath of building blocks for customized applications.
Chemistry markets know diethyl maleate by a handful of names: DEM, diethyl (Z)-butenedioate, and ethenedioic acid diethyl ester. Several manufacturers use proprietary names on their packaging, but all point to the same core formula. For research supply catalogs and regulatory records, synonyms ensure orders go through without mistakes, supporting supply chains for fine chemicals and specialty industries worldwide.
Safe use starts with clear workspace ventilation and strong protocols for chemical handling. Diethyl maleate’s vapor can irritate membranes and cause headaches, so fume hoods and personal protective equipment matter. Spills get treated with absorbent materials combined with proper disposal as hazardous waste. Workers in industrial settings receive training to avoid prolonged skin or eye contact, and a suite of emergency options—eyewash stations, spill kits, and fire extinguishers—should be nearby. Regulatory frameworks such as REACH and OSHA keep updating their standards, reflecting better toxicology studies and field feedback. Plants invest in sensor networks to catch accidental leaks or emission spikes, showing that robust operational culture makes the difference between safe manufacturing and costly incidents.
Industries tap diethyl maleate for its flexibility in synthesis and manufacturing. Producers of resins and adhesives add it as a plasticizer or cross-linking agent, expanding their options for custom blends. Its presence in agricultural intermediates supports formulations that control release or enhance crop protection. In the pharmaceutical sector, drug designers use it to build prodrugs or targeted delivery systems, counting on the compound’s selective reactivity. Specialty coatings and inks benefit from its ability to modify curing rates or improve material compatibility. Research circles rely on small quantities for developing next-generation sensors, functional polymers, or bioactive molecules. These fields invest in both volume supply chains and precision applications, showing a dual approach—bulk utility meets specialty innovation.
R&D efforts around diethyl maleate explore new catalysts for greener synthesis and broaden its scope as a reagent for emerging classes of materials. Initiatives in sustainable chemistry focus on biobased feedstocks for starting materials, trimming down on fossil-derived inputs. Functional studies target its compatibility with advanced polymers destined for electronics and biomedical uses. Multinational collaborations between academia and industry bring new ideas for scaling eco-friendly processes and improving product stability during transit. Start-up ventures test diethyl maleate in high-performance coatings or responsive medical implants, betting on its unique double bond to trigger novel behaviors. These efforts echo a shift toward smarter design, where raw materials play a starring role in transformative technology.
Toxicologists pay close attention to the ways diethyl maleate interacts with biological systems. Short-term exposure can trigger irritation of skin, eyes, and airway, while higher doses in animal models hint at impacts on liver and kidney function. Chronic effects remain rare at occupational levels, but regulators stay vigilant, periodically refreshing permissible exposure limits and requiring thorough documentation during product approvals. Testing in vitro and in vivo informs labeling updates and safety protocols. Manufacturers must back up claims of product purity and processing residues with independent validation, underpinning transparent communication to end users and communities. Research continues into breakdown products and their environmental persistence, building a safer profile for all stakeholders.
The field sees a bright outlook as demand for tailored chemical building blocks rises in both established and emerging markets. Innovations in circular chemistry will likely boost recycling or upcycling of maleate esters, while automation streamlines quality control and reduces batch variance. Advances in digital monitoring promise tighter control of emissions and more predictive maintenance. New product grades could fuel applications from renewable energy storage to smart coatings, reflecting wider shifts in technology and regulation. Connecting laboratory discovery with industrial scale grows ever more critical, and new partnerships—between researchers, suppliers, and users—stand to define the next decade of diethyl maleate’s journey.
Diethyl maleate doesn’t get much attention outside the world of chemistry, but this clear, oily liquid finds its way into more places than most people realize. With a background in chemical manufacturing, I’ve handled chemicals like DEM during the development of products both in the lab and in large-scale settings. Knowing what goes into these processes brings a whole new respect for the building blocks behind products we use every day. DEM isn’t a household name, yet its fingerprints are all around us.
Many people working in manufacturing have seen DEM shipped in blue drums marked with UN warning labels. Manufacturers use DEM as a key ingredient in making other chemicals. It reacts with substances carrying free radicals, helping chemists steer reactions toward exactly the product they want. Painting companies rely on DEM to create certain resins used in coatings for metal and wood. These coatings can stand up to corrosion, moisture, and rough handling—demands that matter on construction sites and in coastal towns where harsh weather is routine.
Think about toys, packaging, or garden hoses. DEM enters the picture in the early stages of crafting soft plastics. To get vinyl or other plastics that bend without cracking, manufacturers look for additives that won’t leave traces or break down over time. DEM fits the bill, helping keep plastics flexible while extending lifespan. Its use supports the comfort and reliability of everyday plastics, from food wraps to medical tubing.
Folks expecting safe fruit and vegetables count on advances in agrochemicals. DEM steps in as a “synergist” for certain pesticides, blocking enzymes in bugs that destroy crops while leaving people unharmed when used by trained professionals following safety measures. This means fewer wasted harvests and better food security. Pharmaceutical labs also draw on DEM to create active ingredients in medications, including drugs used for detox and treatments in hospitals. Behind the scenes, chemists trust DEM’s chemical structure to fine-tune how these drugs act in the body.
Pollution control has drifted from the headlines, but it remains critical. Research shows that DEM can remove harmful mercury from industrial waste streams. By binding with pollutants, DEM makes it easier for engineers to separate toxins from water. Growing up in a region where polluted rivers were just part of the landscape, I’ve seen how technical advances—sometimes as simple as swapping out chemicals—can restore health to waterways and bring fish back to families living nearby. That makes DEM more than just another lab supply—it becomes part of the solution.
Just because DEM helps in so many areas doesn’t mean its use comes without headaches. Chemical spills and improper handling raise health concerns, from skin irritation to respiratory trouble. Factory workers and chemists need protective equipment and training. Safe manufacturing matters for people and the environment, as does oversight of what’s ending up in landfills or storm drains. Responsible sourcing and improved recycling methods could cut the risks further. As industries shift toward safer, greener chemistry, DEM’s story isn’t finished yet.
Diethyl maleate carries the formula C8H12O4. You won't spot this name in a list of household products, but you might be surprised where its chemistry powers the things we use. This clear liquid plays a role in making everything from pharmaceuticals to plastics. One thing that stands out—chemicals like this don’t exist in a vacuum. They shape the world beyond labs and technical manuals. My own years spent in a research environment taught me early that every bottle on a shelf can spark more innovation than a whole toolbox, as long as you understand its makeup.
Having a formula like C8H12O4 on hand works as a universal language for researchers and manufacturers. It tells you the building blocks involved—eight carbons, twelve hydrogens, and four oxygens—a setup with many uses. Diethyl maleate reacts with other molecules through its double bonds, so industries that create additives, resins, or medicines turn to it to make their own processes more efficient or targeted. Without that chemical blueprint, the wrong ingredient could derail a process, causing higher costs, waste, or even safety risks. Standardization helps, especially in supply chains, where sourcing consistency means less headache and higher trust for business partners and consumers alike.
My time spent with safety data sheets underscored the importance of knowing what is being handled. Diethyl maleate can irritate the eyes or skin and might affect workers if released without control. Strict guidelines surround its transport and handling. Following those rules doesn’t just check a box—it keeps people out of harm’s way. On job sites, I watched experienced handlers always double-check labels and protective equipment. Mistakes with chemicals aren’t like forgetting a tool. You can’t undo exposure, so awareness around formulas and risks forms the core of a safe workplace.
Chemicals like diethyl maleate have roles in cleaner, more sustainable production. It often stars in producing water-based coatings and eco-friendlier solvents. The right choice in both formulation and application can cut down on emissions. Over the past decade, I’ve noticed a real shift—a drive among businesses and teams to select ingredients with lower environmental footprints, not just profit in mind. Knowing chemical formulas lets buyers vet supplies more carefully, pushing transparency upstream. Responsible manufacturers publish detailed profiles of their ingredients. It gives regulators, safety engineers, and even end-users the knowledge they need to avoid toxic by-products and promote safer alternatives.
The solution lies in boosting both education and collaboration between those making these chemicals and those using them. Training helps everyone involved—from warehouse staff to researchers—use proper measures in storage, spill response, and transport. Strong communication between suppliers and buyers can weed out misunderstandings and improve quality control. If you’re in industry or research, it pays to dig beyond the chemical’s name and learn what it holds, how it’s made, and how it can be improved. Chemicals like diethyl maleate may sound ordinary, but in the right hands, that formula sets the stage for safe, responsible innovation.
Diethyl maleate shows up in more places than most people think. Folks in chemical plants, scientists, and even workers in plastics manufacturing might encounter it during their regular routines. In research, it helps tweak molecules or adjust how other compounds react. Familiarity with this substance means concerns about its safety come up fairly often.
Any material with a chemical backbone asks for respect. Diethyl maleate might come across as a clear, harmless-looking liquid, but that alone doesn’t guarantee it’s safe. It can irritate the skin and eyes on contact. Breathing in the vapors, especially in a closed space, may lead to headaches, dizziness, or even more serious symptoms. Several industrial data sheets list it as a possible respiratory irritant.
Folks handling this chemical over long stretches run certain risks. Animal studies point to possible liver and kidney effects when high concentrations make their way into bodies. Some research points toward oxidative stress responses, which is a way chemicals can mess with cells and organs over time if exposure stays unchecked. Data from official sources like the U.S. National Library of Medicine suggest people should avoid touching or inhaling this chemical whenever possible.
Diethyl maleate going anywhere except where it belongs introduces more problems. It has some solubility in water so it can spread if it spills. Aquatic creatures in rivers or ponds near manufacturing stations could face stress if a leak escapes into the environment. The chemical doesn’t break down right away, which means ongoing risk in contaminated sites. For the folks living near plants or dumpsites, it becomes more than a lab hazard; it can work its way into the wider world and impact wildlife.
Most facilities that work with diethyl maleate train their people to treat it like a threat. Gloves, goggles, and proper ventilation aren’t just recommendations—they’re required to keep staff safe. Spills need immediate cleanup with proper gear and disposal in tightly controlled waste streams.
Supervisors should stay on top of safety updates. I’ve seen teams cut corners with chemicals, thinking routine makes them immune to trouble. That’s exactly how people end up with burns or headaches. Proper labeling and frequent reminders about danger zones win a lot more respect than posters on a wall. From personal experience, a safety shower that actually works is worth more than any promise to be careful.
Official guidance from groups like OSHA and the European Chemicals Agency puts diethyl maleate on lists requiring strict attention. These organizations don’t take chances. Exposure limits, protective rules, and required reporting all outpace any personal guesswork. In education labs or industrial settings, making rules clear and keeping gear fresh can stop most problems before they build up.
It pays to ask tough questions about any chemical you can’t pronounce. Substances like diethyl maleate deserve the full respect that science, regulation, and common sense can provide. The lesson here rings simple: careful habits and solid information work better than hope when it comes to real-world safety.
Diethyl maleate, a colorless liquid used in a range of chemical manufacturing, always asks for careful attention in the lab or factory. I remember chemistry labs in college, where spills and sneezing classmates proved that a lax approach rarely ends well. Despite its usefulness, this substance carries real health risks. It can irritate skin, eyes, and the respiratory system. In my own experience, colleagues sometimes raised eyebrows at the strong, fruity smell, a hint that proper storage and protection should always matter more than convenience.
Strong protocols around storage work best for chemicals like this. Glass or high-grade HDPE containers with airtight seals usually hold up to the challenge. Metal might seem sturdy, but contact with reactive substances could spell trouble. Cabinets or storage rooms designed for flammable liquids, out of direct sunlight and away from heat sources, keep diethyl maleate stable. I once saw a container left out on a windowsill during summer — the resulting batch spoiled, and lab time blew out for days. Heat and light don’t just cause spills; they destroy product and raise the risk of hazardous vapor spreading.
A cramped, stuffy storage area can turn a minor leak into a major emergency. Fume hoods and constant airflow prevent vapors from building up. In my stints at pharma labs, simple fans rarely did the job. Exhaust systems that draw air away from storage shelves give much better control. If you catch even a faint odor of the chemical in storage, it’s a clue to check airflow and seals right away.
Nobody wants to find out the hard way how chemicals interact with skin and eyes. Gloves (nitrile is the go-to), sealed goggles, and splash aprons cut down on exposure. I once brushed a few drops onto my sleeve during a rushed pour and spent the day with mild irritation. Beyond gear, slow and steady motion matters. Pouring too quickly or lifting a heavy drum without planning can send a fine mist into the air. Labels with hazard warnings front and center help prevent those “I thought that was something else” moments.
Most problems start with shortcuts or forgotten procedures. Ongoing training pays off every time. I’ve seen workplaces where new staff walk through storage routines with a seasoned team member before touching a single bottle. Digital record keeping — simple spreadsheets or inventory software — tracks what comes in, what goes out, and who accessed materials. Such habits catch leaks, theft, and expired containers long before they threaten anyone.
Throwing leftover chemicals down the sink can put everyone in danger and break the law. Dedicated waste containers and assigned disposal runs make a real difference. Absorbent pads, neutralizing kits, and clear instructions keep smaller spills from turning into bigger headaches. After a near-miss with a poorly disposed container, our team overhauled its entire cleanup process, storing spill kits beside every major storage point. The benefits showed up instantly — less confusion, faster cleanup, and fewer stressful days.
Safety in storage and handling does more than protect workers. Keeping diethyl maleate secure means local air and water stay clear, neighbors stay healthy, and businesses avoid hard legal penalties. Paying close attention to every step, from purchase through disposal, drives open trust and safety in any operation.
Factories don’t run on magic—they run on smart chemistry. Diethyl maleate shows up often behind the scenes in chemical synthesis. I’ve seen it used as a building block in the creation of other substances, like additives and specialty esters. The industry leans on its reactivity with thiol and amine groups, so manufacturers use it to make ingredients that end up in everyday plastics and resins. This stuff can help control the physical properties of materials that turn up in consumer goods, making it more important than most folks realize.
Folks growing crops need every tool they can get, and crop protection depends on chemistry as much as rain. Diethyl maleate helps in the formulation of insecticides. Its knack for reacting with glutathione gives it a role as a synergist—meaning, it bumps up how well a pesticide performs. People at the farm level want solutions that work efficiently without too many environmental risks, so scientists keep looking at maleate-based blends to fine-tune action and cut down on overuse.
In my work with manufacturers, I’ve seen engineers hunt for additives that deliver real-world performance in products like adhesives, paints, and coatings. Diethyl maleate takes part in polymer crosslinking. Crosslinking is what makes the difference between a floppy plastic and a sturdy one, letting items hold up over time. It changes the way material stretches or copes with temperature swings, so you get paints that stay put or adhesives that won’t quit under stress.
Every pill starts as a raw ingredient. Labs use diethyl maleate to make other chemicals that end up in medicines. Its chemical structure lets it connect with active molecules without triggering unwanted reactions, which is crucial for safety and predictability. Pharmaceutical routes need reliable intermediates; diethyl maleate has built a good reputation for this job. The tighter regulations on impurity profiles push producers to source high-purity material, and here, transparency in supply chains matters.
Dyeing cloth and keeping colors from fading isn’t a straightforward art. Dyes need to lock into fibers, which sometimes means tweaking the surface. Diethyl maleate works as a modifier, changing fiber properties so they bond better with color. The difference shows up in color fastness after dozens of washes—a detail that matters in everyday life for clothing, upholstery, or even outdoor gear.
Every industry using diethyl maleate faces questions about safety for workers and the broader world. I’ve watched increased scrutiny drive changes in how this chemical gets handled and disposed. The push for green chemistry now encourages companies to revisit how maleates are synthesized, aiming for renewable raw materials and cleaner production routes. Real progress depends on working together. Chemical makers listen to end users, push innovation to limit exposure risks, and support transparency about environmental footprints.
With industries searching for better performance and sustainable options, diethyl maleate’s track record keeps it in play. Efforts now focus on responsible sourcing and lifecycle analysis, tying chemical use to broader goals in health and sustainability. For companies and workers alike, keeping an eye on safety, supply chain integrity, and waste management will shape the reputation—and usefulness—of this compound for years to come.
| Names | |
| Preferred IUPAC name | Diethyl (Z)-but-2-enedioate |
| Other names |
diethyl (Z)-butenedioate
diethyl fumarate DEM maleic acid diethyl ester maleic acid, diethyl ester diethyl cis-butenedioate |
| Pronunciation | /daɪˈɛθ.ɪl ˈmeɪ.li.eɪt/ |
| Identifiers | |
| CAS Number | 141-05-9 |
| Beilstein Reference | 1206821 |
| ChEBI | CHEBI:34779 |
| ChEMBL | CHEMBL1500766 |
| ChemSpider | 7921 |
| DrugBank | DB02044 |
| ECHA InfoCard | ECHA InfoCard: 100.003.198 |
| EC Number | 203-742-5 |
| Gmelin Reference | 77867 |
| KEGG | C01423 |
| MeSH | D006943 |
| PubChem CID | 8027 |
| RTECS number | OD9625000 |
| UNII | 0R2S3U8F4L |
| UN number | UN2362 |
| Properties | |
| Chemical formula | C8H12O4 |
| Molar mass | 172.20 g/mol |
| Appearance | Colorless transparent liquid |
| Odor | Odorless |
| Density | 1.023 g/cm³ |
| Solubility in water | Slightly soluble |
| log P | 1.99 |
| Vapor pressure | 0.11 mmHg (25°C) |
| Acidity (pKa) | 9.56 |
| Basicity (pKb) | 1.79 |
| Magnetic susceptibility (χ) | -7.44×10^-6 cm³/mol |
| Refractive index (nD) | 1.4150 |
| Viscosity | 0.83 mPa·s (20°C) |
| Dipole moment | 2.45 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 489.6 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -468.1 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | –3571 kJ/mol |
| Hazards | |
| GHS labelling | GHS02, GHS07 |
| Pictograms | GHS02,GHS07 |
| Signal word | Warning |
| Hazard statements | H302, H315, H319, H335 |
| Precautionary statements | P261, P280, P304+P340, P312, P305+P351+P338, P337+P313 |
| NFPA 704 (fire diamond) | 2-2-2-0 |
| Flash point | 96°C |
| Autoignition temperature | 415°C |
| Explosive limits | Explosive limits: 1.1%–8.0% |
| Lethal dose or concentration | LD50 oral rat 4700 mg/kg |
| LD50 (median dose) | Rat oral LD50: 4,200 mg/kg |
| NIOSH | Not established |
| PEL (Permissible) | Not established |
| REL (Recommended) | 50 mg/m³ |
| IDLH (Immediate danger) | Unknown |
| Related compounds | |
| Related compounds |
Diethyl fumarate
Dimethyl maleate Diethyl succinate Maleic anhydride Diethyl phthalate |
