2,2-Bis(4-hydroxyphenyl)-propa
4,4'-Isopropylidenediphenol
CAS: 80-05-7
Molecular Formula: C15H16O2
2,2-Bis(4-hydroxyphenyl)-propa - Names and Identifiers
| Name | 4,4'-Isopropylidenediphenol |
| Synonyms | BPA Bisphenol-A Bisphenol A diphenylolpropane 4,4'-Isopropylidenediphenol 2,2-Bis(hydroxyphenyl)propane 2,2-Bis(4-hydroxyphenyl)-propa 2,2-Bis(4-hydroxyphenyl)propane 2,2-Bis (4-hydroxyphenol) propane Tetrabromobisphenol A Allyl Ether 4,4'-(1-Methylethylidene)bisphenol 2,2-Bis(4,4'-hydroxyphenyl)propane 4,4'-(1-methylethylidene)bisphenol 4,4'-(1-methylethylidene)bis-pheno 4,4'-(1-methylethylidene)bis-Phenol |
| CAS | 80-05-7 |
| EINECS | 201-245-8 |
| InChI | InChI=1/2C6H6O2.C3H8/c2*7-5-1-2-6(8)4-3-5;1-3-2/h2*1-4,7-8H;3H2,1-2H3 |
| InChIKey | IISBACLAFKSPIT-UHFFFAOYSA-N |
2,2-Bis(4-hydroxyphenyl)-propa - Physico-chemical Properties
| Molecular Formula | C15H16O2 |
| Molar Mass | 228.29 |
| Density | 1.195 |
| Melting Point | 158-159°C(lit.) |
| Boling Point | 220°C4mm Hg(lit.) |
| Flash Point | 227 °C |
| Water Solubility | <0.1 g/100 mL at 21.5 ºC |
| Solubility | Soluble in alkali solution, ethanol, acetone, acetic acid, ether and benzene, slightly soluble in carbon tetrachloride, almost insoluble in water. |
| Vapor Presure | <1 Pa (25 °C) |
| Appearance | Small white particles |
| Color | Clear light yellow to light orange |
| Odor | Phenol like |
| Merck | 14,1297 |
| BRN | 1107700 |
| pKa | 10.29±0.10(Predicted) |
| Storage Condition | Store below +30°C. |
| Refractive Index | 1.5542 (estimate) |
| MDL | MFCD00002366 |
| Physical and Chemical Properties | Character: White needle crystal or flaky powder. Micro-band phenol odor. melting point 155~158 ℃ boiling point 250~252 ℃ relative density 1.195 flash point 79.4 ℃ soluble in ethanol, acetone, ether, benzene and dilute alkali solution, micro-soluble in carbon tetrachloride, almost insoluble in water. |
| Use | It is used as an important raw material for polymer synthetic materials, and also used for anti-aging agents, plasticizers, pesticide fungicides, etc. |
2,2-Bis(4-hydroxyphenyl)-propa - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R37 - Irritating to the respiratory system R41 - Risk of serious damage to eyes R43 - May cause sensitization by skin contact R62 - Possible risk of impaired fertility R52 - Harmful to aquatic organisms |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S46 - If swallowed, seek medical advice immediately and show this container or label. S39 - Wear eye / face protection. S36/37 - Wear suitable protective clothing and gloves. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 2 |
| RTECS | SL6300000 |
| TSCA | Yes |
| HS Code | 29072300 |
| Toxicity | LC50 (96 hr) in fathead minnow, rainbow trout: 4600, 3000-3500 mg/l (Staples) |
2,2-Bis(4-hydroxyphenyl)-propa - Upstream Downstream Industry
| Downstream Products | 4,4'-(4,4'-isopropylidenediphenoxy)bis-(phthalic anhydride) Polycarbonate Phenolic Resin Tetrabromobisphenol A |
2,2-Bis(4-hydroxyphenyl)-propa - Reference
| Reference Show more | 1. Jia, Xiaohe, et al. "Design, preparation, surface recognition properties, and characteristics of icariin molecularly imprinted polymers." Cogent Chemistry 1.1 (2015): 1059597. 2. Liu, Mengyue, et al. "A high throughput screening method for endocrine disrupting chemicals in tap water and milk samples based on estrogen receptor α and gold nanoparticles." Analytical Methods 12.2 (2020): 200-204.DOI https://doi.org/10.1039/C9AY02179E |
2,2-Bis(4-hydroxyphenyl)-propa - Nature
Open Data Verified Data
White needle crystal or flaky powder. Flammable. Micro-band phenol odor. Boiling point 250~252 deg C. The pure product has a melting point of 155-158 °c. Industrial melting point 150 N152. Relative density 1.195, flash point 79.4. Soluble in ethanol, acetone, ether, benzene and dilute alkali solution, micro-soluble in carbon tetrachloride, almost insoluble in water.
Last Update：2024-01-02 23:10:35
2,2-Bis(4-hydroxyphenyl)-propa - Preparation Method
Open Data Verified Data
phenol and acetone are condensed in the presence of a catalyst, washed with water, crystallized and filtered to obtain a crude product. After recrystallization, centrifugal separation, drying, to obtain the finished product.
Last Update：2022-01-01 10:42:06
2,2-Bis(4-hydroxyphenyl)-propa - Introduction
There is a slight smell of phenol. Decompose at about 260 ℃. It's irritating.
Last Update：2022-10-16 17:28:57
2,2-Bis(4-hydroxyphenyl)-propa - Use
Open Data Verified Data
used in the manufacture of a variety of polymer materials, such as epoxy resin, polycarbonate, polysulfone and phenolic unsaturated resin. It is also used in the manufacture of PVC heat stabilizer, rubber antioxidant, agricultural fungicide, paint, ink antioxidant and plasticizer.
Last Update：2022-01-01 10:42:05
2,2-Bis(4-hydroxyphenyl)-propa - Safety
Open Data Verified Data
- it is less toxic than phenols and belongs to low toxic substance. Rat oral LD50 4200mg/kg. Poisoning will feel bitter, Head Pain, the skin, respiratory tract, cornea irritation symptoms. Operators should wear protective equipment, production equipment should be sealed, and the operation site should be well ventilated.
- It is packed in a wooden barrel, an iron drum or a hemp bag lined with a plastic bag, with a net weight of 25kg or 30kg per barrel (bag). It shall be fire-proof, waterproof and explosion-proof in storage and transportation. It should be kept in a dry and ventilated place. According to the general provisions of the storage and transportation of chemicals.
Last Update：2022-01-01 10:42:06
2,2-Bis(4-hydroxyphenyl)-propa - Reference Information
| LogP | 3.4 at 21.5℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| important organic chemical raw materials | bisphenol A is an important organic chemical raw materials, can be used to produce polycarbonate (Polycarbonate (PC) plastic for making baby bottles), epoxy resin (usually used for the inner coating of some food and beverage cans), polyester resin, Polysulfone Resin, Polyphenylene ether resin, unsaturated Polyester Resin and other polymer materials. It can also be used in the production of PVC stabilizers, plasticizers, flame retardants, plastic antioxidants, heat stabilizers, rubber antioxidants, ultraviolet absorbers, agricultural fungicides, pesticides, coatings and other fine chemical products. bisphenol A is an important derivative of phenol and acetone, which contains two phenolic functional groups and is condensed from two molecules of phenol and one molecule of acetone. The catalyst of this reaction is an acidic catalyst, commercially available catalysts include sulfuric acid, hydrogen chloride and ion exchange resins. The industrial application of these different types of catalysts constitutes the different stages of development of bisphenol A technology. |
| bisphenol A alternatives how safe is Bisphenol S | bisphenol A is a widespread concern mainly due to the detection of bisphenol A in polycarbonate baby bottles and is banned by the EU. The harm of bisphenol A is mainly reflected in its physiological toxicity, which may lead to endocrine disorders, and has a certain degree of carcinogenicity. This is often used in hard food packaging materials, as well as the pharmaceutical field of bisphenol A polycarbonate, the impact is relatively larger, and for the use of structural components, coatings and other fields of epoxy resin, the physiological toxicity of bisphenol A does not cause much impact. Therefore, if we are looking for a substitute for bisphenol A, the main purpose is to solve the safety problem when polycarbonate is used in the field of food and medicine. manufacturers have responded to consumer concerns about the safety of BPA after several studies found it could block chemically mimicking estrogen and potentially harm the brain and reproductive development of fetuses, infants and children, so in 2012 the U. S. Food and Drug Administration issued a restraining order. bisphenol A is a starting material for the production of polycarbonate plastics. The remaining bisphenol A in the plastic container may penetrate into the liquid and then enter the body. Bisphenol S is a good alternative to bisphenol A because it is resistant to leaching. This idea works if people want to be less poisoned by chemicals, it does not cause any harm. but now Bisphenol S will also run out of plastic products. Nearly 81% of Americans have detected Bisphenol S in their urine. Once this substance enters the human body, it does the same damage to cells as bisphenol A. In 2013, an experiment was conducted by ACTH Watson at the University of Texas Medical Branch in Galveston, where one in every million Bisphenol S concentrations could interfere with normal cell function and could lead to metabolic disorders such as diabetes and obesity, asthma, birth defects and even cancer. "It's true that the manufacturer has no bisphenol A on the label," Watson said. But they didn't tell you that bisphenol S, which is added instead of bisphenol A, will also have the same effect on the human body. It seems a little mean. |
| ion exchange resin method | the industrial production of bisphenol A generally uses phenol and acetone as raw materials, preparation by catalytic condensation in acidic medium. Sulfuric acid, hydrochloric acid or strongly acidic cation exchange resins are commonly used as catalysts. Among the above three processes, the sulfuric acid method belongs to the elimination process of hydrochloric acid and ion exchange resin. However, the ion exchange resin method is the mainstream of bisphenol A production process development in the future because of little pollution. The bisphenol a production process by ion exchange resin method was first industrialized by the United States Carbon Company in the early 60 s of last century. The process is characterized by the strong acid cation exchange resin as catalyst, with mercapto compounds as co-catalyst, phenol and acetone according to the ratio of 10:1 in the reactor, reaction at 75 deg C to produce bisphenol A, the product distillation to remove low boiling point components sent to the crystallizer, cooling crystallization separation and purification. The investment cost of this method is low, and the cation exchange resin is used as the catalyst in the synthesis reaction, which can save the nickel base alloy or glass lining resistant to hydrochloric acid. Washing was performed with phenol at the same time, without additional reagents. The recrystallized fine adduct slurry was washed in a separator with pure fresh phenol, and the mother liquor was used as the washing liquid for the first crystallization, and the mother liquor was returned to use after being treated. Thus, in this process, only a small amount of wastewater containing very low amount of phenol and acetone is used to reduce wastewater treatment. In addition, the solid waste material, the exhaust gas, is used as an internal fuel in the process, and no additional treatment is required. This method is a continuous process, easy to open and stop, product quality is high and stable, flexible operation, the same device can produce different levels of products. The deficiency is that the ion exchange resin is filled with large one-time, the single-pass conversion rate of acetone is low, and the acetone recovery device is required. The advantages of ion exchange resin method are no corrosion, little pollution, The catalyst is easy to separate, the product quality is high, the operation is simple, but the catalyst is expensive, and the requirement of the raw material phenol is high. In recent years, this method has been widely used in newly-built facilities abroad. In China, Wuxi Resin plant imported facilities from Poland in the late 80 s of the last century also adopted this method to produce bisphenol A, which has narrowed the gap with the world's advanced level, solve the difficulties encountered in the development of epoxy resin raw materials, so that domestic epoxy resin in the fierce market competition for a place. |
| Application | is an important raw material for the synthesis of polycarbonate, epoxy resin, high temperature polyester, also used as PVC stabilizer, plastic antioxidant, bisphenol A is a widely used product, which is widely used in the production of epoxy resin, polycarbonate, polyester resin, Polyphenylene ether resin and Polysulfone Resin. It can also be used as polyvinyl chloride stabilizer, plastic antioxidant, ultraviolet absorber, agricultural fungicide, rubber antioxidant and so on. It can also be used as an antioxidant and plasticizer for paints and inks. used in organic synthesis, also used as raw materials for the manufacture of epoxy resin and polycarbonate resin used as an important raw material for polymer synthetic materials, also used for anti-aging agent, plasticizer, pesticide, fungicide, etc. |
| production method | results from the condensation of phenol and acetone in an acidic medium. When sulfuric acid is used as the catalyst, the acid concentration is 72.5-76.3% and the reaction temperature is about 40 °c. The reaction is carried out in a stirred tank, which can be produced by a batch process, or an apparatus for continuous production can be arranged. The product is neutralized, dissociated and separated to obtain crude bisphenol A, which is refined by xylene-water extraction method to obtain a finished product. Sulfuric acid method requires less equipment, simple process, but the product quality is poor, high consumption of raw materials, "three wastes" more, only suitable for small and medium-sized intermittent production. In order to obtain a good quality of polymerization grade bisphenol A, a commonly used industrial process is a process using hydrogen chloride gas as a catalyst. Acetone was mixed with phenol, and the reaction was carried out under normal pressure using dry hydrogen chloride as catalyst. The reaction was carried out at 50-60 ° C. For 8-9H, and the concentration of hydrogen chloride in the gas phase was maintained above 96%. In addition to the formation of bisphenol A, the reaction also produces some isomers, trihydroxy or monohydroxy by-products. These small amounts of impurities do not affect the use in the manufacture of epoxy resins. However, when used in the manufacture of polycarbonate, it must be refined. Hooke process is under pressure distillation and extraction crystallization to refine bisphenol A, so that the product cost is reduced. Raw material consumption quota: phenol 940kg/t, acetone 320kg/t, sulfuric acid (98%)500kg/t. |
| spontaneous combustion temperature | 510°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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Downstream Products for 2,2-Bis(4-hydroxyphenyl)-propa
4,4'-(4,4'-isopropylidenediphenoxy)bis-(phthalic anhydride)
Polycarbonate
Phenolic Resin
Tetrabromobisphenol A
Polycarbonate
Phenolic Resin
Tetrabromobisphenol A