光引发剂 BP / 二苯甲酮 CAS 119-61-9
导言
二苯甲酮 is a chemical that has both a carbonyl group and a hydroxyl group in its structure. Its chemical formula can be written as (C6H5)2CO or Ph2CO. It has a white colour and is soluble in organic solvents, and it is soluble in organic solvents. In the process of chemical synthesis, benzophenone is an essential substance since it is used as a precursor for all other diarylketones.
Benzophenone has a relative density of 1.1146, a refractive index of 1.6077, and a melting point between 47 and 49 degrees Celsius. Benzophenone crystals with prisms are colourless and emit a pleasant rose scent. In contrast to water and other organic solvents like chloroform, it dissolves in ether and alcohol. It is a free radical photoinitiator, and free radical UV curing systems are where it finds the majority of its use. Such systems include adhesives, inks, and coatings. In the creation of organic pigments, drugs, fragrances, and pesticides, free radical photoinitiators are also utilised as intermediates. It is primarily used in the pharmaceutical industry to make diphenhydramine hydrochloride and bicyclic piperidine benztropine hydrobromide. This substance, which is frequently used to provide a sweet, sour flavour to soap and perfume, is a styrene polymerization inhibitor and scent fixative. During storage and shipping, the items must be protected from the sun, heat, and moisture, and the temperature must not go beyond 45 degrees Celsius.
Chemical Reactivity
- Benzophenon does not react with water.
- Benzophenon rarely reacts with common materials. I can attack some plastics.
- Benzophenon is highly stable during transportation.
- Benzophenone does not act as a neutriliizng agent for acids and caustics.
- There are no pertinent polymerization and inhibitor polymerization reactions in benzophenone’s presence.
Basic Description
A solid that is white in colour and smells like flowers. When placed in water, may float or sink.
Exposure abilities
In addition to its usage in the synthesis of organic compounds, benzophenone is utilised in the UV curing of inks and coatings, as an intermediate, as an aroma fixative in perfumes, flavours, and soaps, in the production of medicines, and in the development of insecticides.
Purification Techniques of Benzophenone
It can be stored safely on BaO or P2O5 after being crystallised from MeOH, EtOH, cyclohexane, or pet ether, dried in a stream of warm air, and then stored. Furthermore, it is cleaned up by zone melting and sublimation.
Applications of Benzophenone
In printing industry
Benzophenone is a photo initiator that may be utilised in the printing industry for UV (ultraviolet) curing applications such inks, imaging, and transparent coatings. Products with fragrances and colours, such soaps and perfumes, are protected against the damaging effects of ultraviolet (UV) radiation by benzophenone.
The printing industry makes extensive use of benzophenone as a photo initiator for UV-curing applications such as inks, imaging, and transparent coatings. Because it acts as a UV blocker, it protects packaging polymers and the contents they contain from the damaging effects of the sun.
As sunscreens
The most recent development in the cosmetics market is sunscreen cosmetics. Today’s sunscreens almost universally include the ingredient benzophenone. Highs are frequently produced using substances like benzophenone that protect the skin from damage. In recent years, the amount of benzophenone used in cosmetics has significantly increased. Benzophenone is now used in lipsticks, lotions, and hair conditioners since a recent research found that fluorescence is also a harmful source of UV radiation. Additionally, the perfume fixative component, which is extensively used in a range of scents and soap flavours, may give a sweet spice flavour.
AvoTriplex is a UVA-absorbing technology made by Banana Boat. This technique uses benzophenone as its foundation, but it also includes a stabiliser to stop the benzophenone from deteriorating in sunlight. The composition of the benzophenone sunscreen comprises both an enhancer and a stabiliser, which may cooperate to increase the effectiveness of the sunscreen. In biological research, benzophenones are widely used as photophysical probes, particularly for identifying and mapping peptide-protein interactions.
As UV blocker
As a UV blocker, benzophenone can also be used to protect plastic packaging against photodegradation of the polymers or the contents. Producers may utilise transparent plastic or glass to package their products due of its utilisation (such as a PETE water bottle). In its absence, the container would have to be opaque or black.
In perfumes
Benzophenone gives “sweet-woody-geranium-like overtones” when employed as a flavouring or perfume component.
In food items
Benzophenone In addition to its principal function in the creation of vanilla, butter, and a number of other flavours, this molecule may also be utilised as a fixative. It is appropriate for use in a variety of low-grade flavours, including roses, bay leaves, sweet curd, shy flowers, lily of the valley, sunflower, orchid, hawthorn blossoms, incense, and Wei Oriental flavour, among others, because of its weak sweetness and fragrant character. It is used to enhance the flavours of almonds, berries, fruit, butter, nuts, peaches, vanilla beans, and other foods. It is also used as an antioxidant in soaps.
Uses for photosensitive resins, coatings and adhesives
A precursor that is utilised in the production of UV absorbers, pesticides, medicines, and scents is called benzophenone. In the pharmaceutical business, it is utilised in the production of bicyclic piperidines, examples of which include diphenhydramine hydrochloride and benzotropine hydrobromide. This chemical stops odours from developing while also preventing the polymerization of styrene. Because it has such a lovely scent, it may be found in a wide variety of soaps and perfumes.
It is a component of UV absorbers, pigments, pharmaceuticals, and chemicals, and it is also used in the flavouring of soap. Additionally, it is used as a quick-curing agent at low temperatures for fluorine rubber, and it is used in the production of fluorine rubber. It is possible that manufacturers may benefit from using containers made of transparent glass or plastic.
As light activator
In addition to its many other applications, it is utilised as a light activator in the production of ultraviolet (UV) goods, pharmaceutical intermediates, perfumes, and light stabilisers.
As initiator
Initiator for UV-curable resins, inks, and coatings; intermediate in the production of light-pigment, fragrance, medication, and insecticide.
As an indicator
When working with toluene, benzene, THF, acetonitrile, and other chemicals, benzophenone is frequently used as an indicator. If a lovely blue colour appears after addition, the substance can be distilled and used. Benzophenone is best stored in sodium, but the precise mechanism by which this colour is produced is unknown. The following non-English literature on chemical reaction mechanics possibly include the explanation: Because its oxygen atoms absorb electrons from sodium to produce a dark blue carbonyl radical with a stable electrical state, benzophenone is used as an indicator of anaerobic conditions. It is often employed.
With the addition of benzophenone, the solution took on a more blue appearance, indicating that there was less oxygen available and serving as an unconscious cue to drink less water. Whether the solution becomes blue throughout the procedure depends on the amount of benzophenone and the solvent used. It is advised to use common desiccants like potassium carbonate, sodium sulphate, sodium hydroxide, and others to pre-treat the sample because THF (300ml) contains a significant amount of water and takes more than 6 hours to reflux. The duration of the reflux is directly inversely correlated to the volume of solvent used in the method; the larger the volume, the longer the reflux duration.
Synthesis
Benzophenone is produced when copper catalyses the oxidation of diphenylmethane with air.
The hydrolysis of the produced diphenyldichloromethane follows the laboratory reaction of benzene with carbon tetrachloride. Additionally, it is created using the Friedel-Crafts acylation of benzene with benzoyl chloride while using a catalyst made of Lewis acid (for example, aluminium chloride). This was the starting point for the first synthesis since the reaction of benzene and phosgene produces benzoyl chloride quickly. Another method of synthesis makes use of the catalyst palladium(II)/oxometalate. With two groups on either side, an alcohol is converted into a ketone during this process.
Another method for producing benzophenone involves the pyrolysis of anhydrous calcium benzoate, however this method is less well-known.
Safety Standards
It is said to as “basically harmless” due to the fact that it poses very little to no risk to anyone. In spite of the fact that the FDA has maintained its position that benzophenone does not provide a risk to public health when used as it was intended, the drug is still prohibited from use as an addition in food in the United States. It is well knowledge that benzophenone chemicals can exert a pharmacological effect on living organisms. The chemical connection between benzophenone and B-DNA has been deduced at the molecular level. It is possible that some of benzophenone’s therapeutic potential might be attributed to the fact that it acts as a DNA photosensitizer—a function that relies on the substance’s interaction with DNA and the subsequent transfer of energy to the molecule through the use of light.
Exposure Standards
In the event that the following conditions are satisfied, benzophenone may be directly added to human food in the capacity of a synthetic flavouring and adjuvant: a) they are used in the smallest amount necessary to produce their intended effect, and otherwise in accordance with all principles of good manufacturing practise; and b) they contain one or more of the ingredients listed below, either alone or in combination with other flavourings and adjuvants: a. ethyl acetate, ethyl benzyl benzoate, benzyl acetate, and benzyl alcohol.
Benzophenone Derivatives
There are over 300 benzophenones that are found in nature, and each one has a special mix of structural characteristics and biological function. They are being studied because they might produce cutting-edge medications. Two widely found substituted benzophenones in sunscreens are oxybenzone and dioxybenzone. A well-known and often employed substituted benzophenone is octibenzone. Benzophenone compounds, which structurally resemble a potent photosensitizer, have come under harsh criticism for their use. In Michler’s ketone, dimethylamino substituents are present in each of the para locations. PEEK high-strength polymer is made from derivatives of benzophenone.
Carcinogenicity Test
According to research conducted on the lifetime carcinogenicity of the skin in mice and rabbits, it was found that there was no evidence of an increase in the frequency of tumours in the animals that were treated. The skin of Swiss female mice and New Zealand White rabbits, both male and female, was treated topically with varying concentrations of benzophenone over a period of either 120 or 180 weeks (0.02 mL twice weekly). Even though each rabbit was evaluated once a week, neither the survival rate nor the number of tumours increased during the course of the experiment. When compared to animals who were not given medicine, mice that were given benzophenone did not grow a greater number of tumours overall, nor did they develop a greater number of individual tumours. The mice that were treated with benzophenone had three skin tumours, one of which was squamous cell carcinoma and the other two were squamous cell papillomas. However, the control animals also developed three skin tumours (one carcinoma and toe papillomas).
结论
Benzophenone has a melting point of 48.1 degrees Celsius and appears as a white, crystalline solid. It smells rose-like and also has a hint of geranium. It is possible to produce this chemical by reacting either benzene and benzoyl chloride with aluminium chloride or benzene and carbon tetrachloride. Oxidation of diphenylmethane can also result in the formation of benzophenone. It is also used as a fixative and is commonly used in flower arrangements. The printing industry makes regular use of benzophenone as a photo initiator in UV-curing applications such as inks, imaging, and transparent coatings. This practise is common in the printing industry. Because it acts as a UV blocker, it stops the photodegradation of the packaging polymers as well as the contents of the packages. It protects some things, including soaps and scents, from the sun’s ultraviolet rays. It is beneficial for manufacturers to package their goods in see-through materials like plastic or glass.
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