Nanjing Liwei Chemical Co., Ltd

Знание

4-Vinylphenol: A Deep Dive into Its Past, Present, and Future

Historical Development

The story of 4-vinylphenol winds through over a century of organic chemistry. Chemists first took note of this compound in the late 19th century. It cropped up as a natural degradation product in a handful of fermentation reactions. Decades rolled by, and it found its place in labs interested in phenolic derivatives, especially as advances in polymer science ramped up after World War II. Researchers began tuning its structure and testing its reactions, realizing early on that 4-vinylphenol offered a valuable bridge between fundamental chemistry and the burgeoning field of synthetic resins.

Product Overview

4-Vinylphenol stands out as a versatile monomer used in multiple fields. Its commercial importance stretches from flavor chemistry all the way to high-performance plastics. Chemically, it’s a phenolic compound – meaning it carries both a benzene ring and a reactive hydroxyl group. You notice this in its mild aromatic odor, a detail that’s actually critical in brewing, since unwanted yeast strains can generate it and spoil a batch of beer with “off” flavors. Away from the food world, manufacturers tap 4-vinylphenol to build specialty polymers thanks to its combination of reactivity and stability.

Physical & Chemical Properties

A clear, colorless to slightly yellow solid at room temperature, 4-vinylphenol melts at roughly 52°C and boils at 227°C under standard pressure. Because of the vinyl group, the compound reacts with ease through polymerization. The phenol moiety means it can participate in hydrogen bonding and shows moderate acidity, with a pKa around 9.9. The substance dissolves in many organic solvents like ethanol, ether, and chloroform, but it won’t easily dissolve in water. Stability depends on light and temperature; storing it in cool, dark conditions lengthens shelf life and lowers risk of spontaneous polymerization.

Technical Specifications & Labeling

Chemical suppliers often sell 4-vinylphenol at purities above 98%, packaged in amber or inert-coated containers to keep it stable. Container labels typically display the chemical formula (C8H8O), molar mass (120.15 g/mol), batch number, manufacturing date, and clear hazard symbols reflecting flammability and toxicity. Since the vinyl group reacts easily, storage instructions warn users to avoid excessive heat and exposure to direct sunlight. Many suppliers include a certificate of analysis to help labs verify the quality and purity of each batch.

Preparation Method

Industrial chemists produce 4-vinylphenol mainly by decarboxylating p-coumaric acid under controlled heat and pressure. This method mimics the natural reactions carried out by some bacteria and yeast, but it’s tweaked for efficiency and purity. Another route starts with 4-ethylphenol, which gets oxidized and then dehydrogenated to bring in the vinyl group. Rigorous purification steps, including distillation under vacuum conditions, help achieve a product clear of impurities that could either spoil polymerization reactions or introduce unwanted flavors in food work.

Chemical Reactions & Modifications

In the lab, 4-vinylphenol excels as a building block. Its vinyl group kicks off free-radical polymerizations under the right catalytic conditions, letting chemists make specialty plastics, copolymers, and ion-exchange resins. The phenol group stays open for further modifications: etherification, esterification, and even nitration reactions generate a flood of derivatives. Many research teams have linked 4-vinylphenol units to bigger molecules, chasing novel surfactants or designing monomers for new adhesives. In metabolic studies, this molecule steps in as a marker for certain spoilage yeast in winemaking, since it impacts aroma and flavor profiles.

Synonyms & Product Names

Chemists know this compound by a range of names: p-vinylphenol, 4-ethenylphenol, and para-vinylphenol show up in older literature. Producers sometimes reference trade names or catalog numbers, but the core identifiers rarely change. On the analytical front, databases list it by CAS number 2628-17-3, and industry workers in flavor or resin development recognize both its systematic and common monikers when ordering.

Safety & Operational Standards

4-Vinylphenol requires careful handling due to its moderate toxicity and potential to irritate skin, eyes, or airways. Direct exposure causes redness or discomfort, so standard operating procedures call for goggles, gloves, and use of well-ventilated fume hoods. Storage away from incompatible materials — acids, oxidizers, or open flames — heads off many risks. Spill protocols stress containment with absorbent material, followed by neutralization and secure disposal. Emergency data sheets accompany every shipment, citing exposure limits, and many companies train staff on protocols that exceed minimal compliance to keep labs and workshops safe.

Application Area

4-Vinylphenol has roots in both the flavor and fragrance industry and the worlds of polymers and advanced materials. Its presence in food and drink sparks concern among brewers and vintners, especially when spoilage microbes start generating levels that tank product quality. In plastics, the vinyl group brings mutability: cross-linking leads to hard-wearing resins, useful in ion-exchange membranes for water treatment, electronics, and adhesives. Researchers studying surface coatings seek out 4-vinylphenol-based polymers for better thermal and chemical resistance. Some niche sectors look for it as a precursor in the synthesis of specialty chemicals used in pharmaceuticals and agrochemicals.

Research & Development

Over the last few decades, the field has shifted. Analytical chemists invent better ways to detect trace levels in beverages to support food safety. Polymer scientists experiment with 4-vinylphenol in new copolymers tuned for selective ion transport or improved stability. Industry-academic collaborations focus on “green” chemistry routes using renewable starters such as lignin derivatives, hoping to build sustainability into both the feedstocks and the processes. Graduate students and postdocs, especially in organic labs, continue to probe the radical mechanisms of vinylphenol-based polymerizations, sometimes hitting on breakthroughs that trickle outward into applied products.

Toxicity Research

Toxicologists have put 4-vinylphenol under the microscope, tracking its impact on living tissues and organs. Results point to moderate acute toxicity; oral and dermal exposures in rodents provoke discomfort, reddening, or — at higher doses — mild systemic effects. Eyes and mucous membranes stay especially sensitive. In fermentation industries, even minor spills draw attention because of potential downstream contamination. Most published studies so far haven’t flagged the substance as a carcinogen, but regulatory agencies recommend minimizing exposure due to its irritant profile and incomplete long-term data.

Future Prospects

From materials science to green chemistry, 4-vinylphenol finds itself at a threshold. Scientists have their eye on scaling up biosynthetic routes, trying to replace petrochemical starting materials and ease pressure on supply chains. In polymers, the push for next-generation membranes — for batteries, desalination, or fuel cells — keeps demand high for specialty monomers like this. Researchers see the molecule as a testbed for new cross-linking strategies or as a platform for designing “intelligent” materials that respond to light or heat. Meanwhile, the food and beverage sector continues to watch for methods to control its formation and detection, tying sensory analytics to practical steps in quality assurance. As commercial and academic labs keep working, 4-vinylphenol’s blend of versatility and reactivity ensures it won’t fade from the scene anytime soon.



What is 4-Vinylphenol used for?

Pinning Down the Source

Every time I sip on a glass of wine and catch that slight whiff of Band-Aid or barnyard, I think about 4-vinylphenol. This compound pops up in more places than many realize. Yeasts can pump it out during fermentation, which means wineries and breweries end up dealing with it as much as labs do. Over the years, I’ve come across plenty of vintners who have struggled with this aromatic compound, wishing they could just tune the dial on its intensity.

What Does It Actually Do?

4-Vinylphenol’s main claim to fame comes from how it changes the flavor and scent of drinks. Brettanomyces yeast cranks it out from natural ferulic acid in grape skins and barley husks. Even a little can take a delicate Chardonnay and give it a sharp medicinal tang. That’s not always welcome. Brewers face the same challenge with wheat beers, though some styles chase a hint of clove or spice because of it. People working in quality control watch for its presence like hawks.

On the flip side, this compound finds work in labs and factories. Chemists run with 4-vinylphenol when making resins and specialty plastics. The double bond opens the path to clever reactions. I’ve watched polymer chemists use it to add rigidity or tweak chemical resistance in a finished product. It isn’t as common as other monomers, but in certain coatings and adhesives, it holds real value.

Researchers also lean on it while studying enzyme activity. Enzymes in plants and microbes clip ferulic acid from cell walls, and 4-vinylphenol steps in as a handy marker during experiments. Its distinct aroma doesn’t just give a clue in the lab—sometimes it leads researchers down new paths discovering which bugs or strains break things down and at what speed. Tracing this compound helped labs understand spoilage in drinks, but also led to better fermentation control in biotech and agriculture.

Why It Matters Right Now

Anyone thinking about food safety or consumer satisfaction stumbles across 4-vinylphenol eventually. Modern drinks cover a huge market. A bad batch—blamed on the wrong yeast, slipshod storage, or dodgy sanitizing—spells trouble for brands and producers. In my experience with small breweries, a sudden vinyl-like note in a flagship beer calls for more than just tweaking recipes. It means revisiting sanitation routines, tracking yeast sources, and testing lots more often.

Beyond taste and aroma, this compound brings up bigger questions about chemical safety and workplace exposure. Industrial processes with aromatic monomers must keep emissions in check. At certain doses, these chemicals irritate skin and lungs—a lesson that gets hammered in during safety briefings on the production floor. Regulatory agencies in Europe and the US have published exposure limits and recommend standard protective protocols. Personally, I’ll never forget how fast my nose picks it up in an unventilated lab space.

Looking for Solutions

For drinks, better yeast selection and careful fermentation help keep flavors on track. Breweries lean on rapid lab testing and strict cleanliness. Some are turning to non-traditional microbes or refining their malting to cut down the ferulic acid pool. In polymer science, green chemistry pushes for new building blocks with fewer health or environmental risks, but for now, 4-vinylphenol stays in the mix for certain uses.

I find it’s a classic case: chemistry shapes both the flavor in a bottle and the backbone of an advanced material. Shining a light on 4-vinylphenol means spotting where tradition meets technology, and remembering that even one little molecule changes the story in a big way.

What are the safety precautions when handling 4-Vinylphenol?

Why Precaution Matters With 4-Vinylphenol

Working in labs taught me that chemicals with hard-to-pronounce names tend to demand attention, and 4-vinylphenol fits the bill. This compound plays a part in research and industry, but treating it like just another bottle on a shelf can land someone in trouble. Inhalation, skin contact, and accidental ingestion each open the door to real risks—think skin burns, irritated lungs, even long-term toxicity with repeated mishandling.

Personal Protection Counts

Gloves aren’t optional. I reach for nitrile gloves—latex sometimes breaks down with harsher organics, so nitrile keeps my skin protected. For the eyes, regular glasses don’t cut it. Tight-fitting goggles shield against splashes. A lab coat does more than mark someone as a scientist; sleeves and thick cotton keep spills off skin and street clothes. In high-hazard situations, adding a face shield offers peace of mind.

Ventilation Makes a Difference

Cracking open a window won’t help with chemical fumes. Before the cap comes off 4-vinylphenol, a certified fume hood needs to be running. I’ve learned to test airflow with a piece of paper before trusting it. Good ventilation means vapors and dust exit the workspace, keeping airways clear. Relying on open-air handling piles on the risk without reward.

Handling and Storage: Respect the Rules

Walking through chemical storage areas shows how labels matter. 4-vinylphenol stays in a tight-sealing, chemical-resistant container. I check expiration dates and make sure it sits far from heat, ignition sources, or reactive chemicals. At room temperature, it’s already volatile, so minimizing time outside storage is part of my routine.

Spill and Exposure Response

Spills happen—rushing never pays off. For a small spill, good practice includes covering with absorbent material and cleaning up with gloves and goggles on. Used materials drop straight into a hazardous waste bag, never into the regular trash. If 4-vinylphenol hits skin, the affected area gets rinsed with cool running water for at least 15 minutes before seeking medical help. Inhalation calls for a quick move to fresh air, alerting a supervisor, and—if there’s any doubt—getting checked out.

Training and Information

One lesson reinforced over the years: workplace rules exist for a reason. Everyone handling 4-vinylphenol goes through safety training. Safety Data Sheets (SDS) must stay nearby. Relying on last month’s memory rather than reviewing current protocols leaves too much to chance. Regular refreshers keep skills sharp, and open communication means issues get flagged before accidents happen.

Toward Safer Labs and Workplaces

Tough standards and habits didn’t appear overnight. Seeing the consequences of casual handling—wasted material, ruined experiments, sometimes real injury—shapes how I treat substances like 4-vinylphenol. Encouraging a speak-up environment, reviewing best practices together, and investing in quality gear all work together to cut risks. Every precaution on this list represents someone’s hard lesson learned, and no job benefits from shortcuts with safety.

What is the chemical structure of 4-Vinylphenol?

Breaking Down the Chemistry

To get a clear picture of 4-vinylphenol, it's worth imagining molecules as something tangible, like pieces of a jigsaw. This compound comes from phenol, a structure lots of folks meet in chemistry class. Picture a benzene ring with an attached -OH group. Now, in 4-vinylphenol, a vinyl group takes up a spot opposite that hydroxyl group—the para position. The result: C8H8O. It looks like this: a hexagonal benzene with an -OH on one carbon, and on the directly opposite carbon, a two-carbon vinyl group, -CH=CH2. That’s about as stripped-down and raw as a molecule can get without losing its quirky properties.

Everyday Impact: More Than Just Aromatics

I once helped a friend review a batch of wine and beer for off-flavors in a small tasting room. In that crowd, anyone mentioning “vinyl” triggered a near-universal cringe—4-vinylphenol carries a medicinal, plastic note. What’s wild is that just a whiff alerts professionals to the workings of wild yeast, namely Brettanomyces and certain bacteria that transform precursors in grapes and grains into this aromatic oddball. The presence of 4-vinylphenol can ruin a vintage, or in the right dose, lend intrigue.

Studies from places like the American Society of Brewing Chemists show how brewers test for this compound to keep beer from tasting like sticking plasters. Scientists discovered that the vinyl group loves to take on new transformations—turning into polymers or reacting with light, making researchers in materials science perk up. These quirks push the molecule beyond the dinner table and straight into the lab.

Why Structure Matters For Function

Chemistry explains why a subtle change sparks big results. When a vinyl group shares space with a phenol, it sets up possibilities for reactions. Sunlight, heat, and other chemicals see an opportunity, and chemists exploit that for plastic production, coatings, even adhesives. In the food industry, watching for 4-vinylphenol means protecting product flavor and quality. Rigid wine regulations across Europe now outline safe levels, led by years of research on its molecular fingerprint.

Room for Solutions

Problems crop up when natural processes run unchecked. Anyone growing grapes, managing a brewery, or bottling organic compounds knows that yeast contamination flips a product’s profile fast. Advanced labs install sensors built around the structure of 4-vinylphenol, which grab and isolate the molecule for early detection. This helps avoid the heartbreak of ruined batches. Some wineries embrace gentle filtration and controlled fermentations. Training in yeast management, proper sanitation, and rigorous checks can help keep this compound from sabotaging end products.

Outside of beverages, scientists see promise: tweaking the vinyl group or the phenol’s position steers material properties, opening doors for green chemistry and bioplastics. Researchers reference studies like those published in Polymer Chemistry, which detail how minute structural variations drive performance in sustainable materials. One solution is to design better catalysts that guide these molecules down desirable chemical paths—using what’s already present in nature, rather than brute-force synthesis strategies that create toxic waste.

Experience From the Lab and Beyond

Years of handling samples in both research and quality control remind me how a single molecular tweak echoes through industries. Getting curious about molecular structure often leads to smarter choices in agriculture, production, and sustainability. For students or professionals working with chemicals, a strong grasp on what each part of a molecule does makes all the difference. In the story of 4-vinylphenol, structure shapes flavor, safety, and future materials in ways that blend hard science with real life.

How should 4-Vinylphenol be stored?

Practical Lessons Learned in the Lab

Storing 4-Vinylphenol isn’t just another step to check off a list. Ask anyone who’s worked with volatile chemicals, and most will agree that carelessness only brings trouble—lost research, ruined samples, maybe a blown-up fume hood. Over the years, I’ve seen enough cracked vials and yellowed liquids to know: this compound reacts to sloppy storage. Even exposure to air or light brings out the worst in it.

In my early days, I kept a sample near an open bench. The odor stuck around for hours, and more than one lab mate complained. Later, I learned why 4-Vinylphenol belongs behind tightly sealed lids—it escapes into the air, it stings your nose, and it loves to oxidize. The next time, I followed the protocol: segregated it in cool, dry storage, and the problems vanished.

What Makes 4-Vinylphenol So Touchy?

This phenolic compound packs a punch. It usually arrives as a colorless to yellow liquid, but it doesn’t wait long to show a darker face. Air and moisture help it break down. That breakdown not only changes its properties but can also make it more hazardous. I’ve looked at safety data sheets (SDS) for dozens of chemicals, and 4-Vinylphenol keeps popping up with warnings against air, sunlight, and any hint of flame.

Health risks don’t fade in storage. Short-term exposure brings irritation to eyes and skin. Vapors hurt breathing. Even low-level contamination makes a difference in the lab, especially for those hoping to run clean experiments or keep odors manageable.

Getting Storage Right: Safety and Quality Go Together

The answer isn’t complex—just careful. Always pick bottles made from glass or compatible plastics with tight seals. Choose small vials if you’ll only use the contents in tiny volumes. Avoiding wide-mouthed containers limits the surface area that air can hit. Brown glass cuts out most light, slowing down degradation. If you look at real-world incidents, broken containers or loose lids usually lead to spoiled batches and wasted money.

Find a spot for storage out of direct light, away from lab benches and traffic. Temperatures should stay low. Standard practice in research and industrial settings keeps compounds like this in dedicated chemical refrigerators. No freezers near food—even trace contamination leads to unexpected problems nobody wants in a shared workplace.

Don’t ignore proper labeling. Labels mark the date received, the source, and hazard warnings. Every year or so, check your chemicals. If 4-Vinylphenol’s sitting for too long, it could turn or even leak. Disposal rules matter, too. From firsthand experience, trying to pour leftovers into a sink brings consequences. Work with a recognized chemical waste program; dumping it will only harm the environment and break the rules.

Building Safer Lab Habits

Everyone handles mistakes, but some can be avoided with a little attention upfront. 4-Vinylphenol rewards diligence and punishes shortcuts. In my own work, setting aside five minutes for storage saves hours of cleanup later. Good habits get reinforced by training, sharing war stories, and working together to keep chemicals under control.

Safe storage for 4-Vinylphenol isn’t a luxury—it's a foundation for any lab or facility that uses it. Understanding the risks, choosing the right containers, and following disposal rules go a long way. Safety and sample quality both benefit, and a well-run lab feels the difference.

What are the potential health hazards of 4-Vinylphenol exposure?

What is 4-Vinylphenol?

4-Vinylphenol turns up in places where refining or processing of plastics and resins happens. Factories, labs, or sites that handle styrene or certain food additives let out 4-Vinylphenol as part of their standard processes. The compound also shows up as a product of wood smoke or grilled foods. Most people will never hear about it, yet the risks demand closer attention, especially for workers who spend their days near it.

Direct and Long-Term Effects

Even short stints around 4-Vinylphenol can lead to a scratchy throat, breathing problems, or skin irritation. Anyone working in a chemical plant knows the hot, raw feeling after a spill or bad ventilation day. If inhaled, the fumes sting the eyes and make the chest feel heavy. Repeated contact toughens the skin, sometimes cracks it open, then waits for infection to set in. Over time, the real danger grows in the lungs, the liver, and the nervous system.

The compound acts as both an irritant and a disruptor. Studies in lab animals show changes in liver tissue and signs of nerve injury after repeat exposure. Human data feels hard to pin down, since real-world exposure doesn’t happen in a lab. But history tells that chemicals similar to 4-Vinylphenol—styrene, for instance—can raise cancer risk, slow brain response, and hurt the immune system. The World Health Organization and EPA agree: handling vinyl compounds means playing with fire when it comes to long-term health.

Invisible Hazards at Work

Older factories and research sites often use outdated air filters or plastic shields, which don’t keep out fumes. Managers may ignore ventilation needs or warn about spills only after the fact. Workers get exposed during accidents, equipment cleaning, or badly sealed storage tanks. Farm workers can also get a hit from pesticide drift, since vinyl compounds show up in some sprays. Anyone grinding old plastic, working with synthetic rubber, or fixing up pipes faces more risk.

Weighing the Evidence

Peer-reviewed studies published by environmental health journals show increased biomarkers for liver stress and inflammation in people working near 4-Vinylphenol. Monitoring data collected after chemical fires in urban areas found detectable levels in blood, tied to headaches and lasting fatigue. Epidemiologists point out that the compound breaks down to phenol, a toxin known to damage organs over years. Though no clear dose-threshold exists for human safety, countries like Germany and Japan recommend tough standards for workplace exposure—far stricter than U.S. federal law.

Protecting Health in Real-World Settings

Employers should set up regular blood testing for workers exposed to 4-Vinylphenol. Better on-site air monitors cut the guessing game. Factory ventilation and sealed storage tanks beat out relying on masks and gloves alone. Shutting down and cleaning up equipment before workers open it stops most sudden exposures. People living near factories need fresh data about local air and soil levels, plus honest reporting by plant operators. Local governments should track cancer and respiratory illness rates among neighbors over time and push companies to shift toward safer alternatives.

Moving Forward

Nobody wants to see the next big health crisis born out of neglect or wishful thinking. Policymakers should tighten rules, while companies invest in smarter safety. From my own days around factories in the Midwest, small upgrades—a new fan, better suit, honest training—made a difference workers could feel. Awareness, stricter standards, and a mix of personal and engineering controls go a long way to cut harm. No one can dodge every risk, but we owe it to workers and neighbors to seek out safer paths wherever possible.

4-Vinylphenol
4-Vinylphenol
4-Vinylphenol
Names
Preferred IUPAC name 4-Ethenylphenol
Other names 4-Ethenylphenol
4-Hydroxystyrene
p-Ethenylphenol
p-Hydroxystyrene
para-Vinylphenol
Pronunciation /ˈfɔːr-vaɪˌnɪlˈfiːnɒl/
Identifiers
CAS Number 2628-17-3
Beilstein Reference 1209229
ChEBI CHEBI:51435
ChEMBL CHEMBL48670
ChemSpider 11847271
DrugBank DB08220
ECHA InfoCard InChIKey=IMRVYINLGBKYMO-UHFFFAOYSA-N
EC Number 4.1.1.44
Gmelin Reference Gmelin Reference: 82761
KEGG C06505
MeSH D014807
PubChem CID 7489
RTECS number SG3150000
UNII 6N9FDQ2F6V
UN number UN2431
Properties
Chemical formula C8H8O
Molar mass 120.15 g/mol
Appearance Colorless to pale yellow liquid
Odor sweet; phenolic
Density 1.045 g/mL at 25 °C
Solubility in water slightly soluble
log P 1.98
Vapor pressure 0.187 mmHg (at 25°C)
Acidity (pKa) 10.0
Basicity (pKb) 12.45
Magnetic susceptibility (χ) -60.0·10⁻⁶ cm³/mol
Refractive index (nD) 1.578
Viscosity 2.93 mPa·s (25 °C)
Dipole moment 1.51 D
Thermochemistry
Std molar entropy (S⦵298) 313.8 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) 45.5 kJ/mol
Std enthalpy of combustion (ΔcH⦵298) -3255 kJ/mol
Hazards
GHS labelling GHS02, GHS07
Pictograms GHS02,GHS07
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements Precautionary statements for 4-Vinylphenol are: "P210, P261, P280, P305+P351+P338, P337+P313, P403+P233, P501
NFPA 704 (fire diamond) 2-2-0
Flash point Flash point: 113°C
Autoignition temperature 490 °C
Explosive limits 4.2–5.6%
Lethal dose or concentration LD50 (oral, rat): 1630 mg/kg
LD50 (median dose) LD50 (median dose): Rat oral 900 mg/kg
NIOSH RN0133
PEL (Permissible) Not established
REL (Recommended) 100-500 mg
IDLH (Immediate danger) Unknown
Related compounds
Related compounds Phenol
Styrene
4-Ethylphenol
4-Vinylcyclohexanol