ACETAMINOPHEN IMPURITY K
4-Aminophenol
CAS: 123-30-8
Molecular Formula: C6H7NO
ACETAMINOPHEN IMPURITY K - Names and Identifiers
| Name | 4-Aminophenol |
| Synonyms | AZOL CITOL PARANOL CERTINAL C.I. 76550 4-Aminophenol P-Aminophenol AMINOPHENOL-4 P-Amino phenol para aminophenol 4-Hydroxyaniline Para-aminophenol P-HYDROXYANILINE C.I. Oxidation Base 6 4-Amino-1-hydroxybenzene ACETAMINOPHEN IMPURITY K 1-amino-4-hydroxybenzene 4-Amino phenol |
| CAS | 123-30-8 |
| EINECS | 204-616-2 |
| InChI | InChI=1/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 |
| InChIKey | PLIKAWJENQZMHA-UHFFFAOYSA-N |
ACETAMINOPHEN IMPURITY K - Physico-chemical Properties
| Molecular Formula | C6H7NO |
| Molar Mass | 109.13 |
| Density | 1.29 |
| Melting Point | 188 °C |
| Boling Point | 284 °C |
| Flash Point | 189 °C |
| Water Solubility | 1.5 g/100 mL (20 ºC) |
| Solubility | water: slightly soluble |
| Vapor Presure | 0.4 hPa (110 °C) |
| Appearance | Crystalline Powder |
| Color | White to cream |
| Merck | 14,462 |
| BRN | 385836 |
| pKa | 5.48, 10.30(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable, though may discolour in air. Incompatible with acids, chloroformates, strong oxidizing agents. |
| Sensitive | Air & Light Sensitive |
| Refractive Index | 1.5444 (estimate) |
| Physical and Chemical Properties | Character white or light yellow-brown crystal. melting point 186~187 ℃ boiling point 110 ℃ solubility: slightly soluble in water and ethanol, insoluble in benzene and chloroform, and quickly brown when dissolved in alkali. |
| Use | For the production of vulcanized blue FBG, weak acid yellow 5G and other dyes, the manufacture of paracetamol, antoamine and other drugs, also used in the preparation of developer, antioxidant, etc |
ACETAMINOPHEN IMPURITY K - Risk and Safety
| Risk Codes | R20/22 - Harmful by inhalation and if swallowed. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R68 - Possible risk of irreversible effects R40 - Limited evidence of a carcinogenic effect |
| Safety Description | S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/37 - Wear suitable protective clothing and gloves. S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S28A - |
| UN IDs | UN 2512 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | SJ5075000 |
| FLUKA BRAND F CODES | 8 |
| TSCA | Yes |
| HS Code | 28402090 |
| Hazard Class | 6.1 |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 375 mg/kg LD50 dermal Rabbit > 10000 mg/kg |
ACETAMINOPHEN IMPURITY K - Upstream Downstream Industry
| Raw Materials | 4-Nitrophenol 4-Nitrophenol Sodium metabisulfite Sulfuric acid Sulfuric acid Iron Iron Iron Hydrochloric acid Hydrochloric acid |
| Downstream Products | 4-Acetamidophenol |
ACETAMINOPHEN IMPURITY K - Nature
Open Data Verified Data
white, yellow or pink crystals or crystalline powders. Insoluble in benzene and chloroform. Change to purple in light or open air. It can burn when exposed to open fire. Toxic and corrosive gases are decomposed by heat.
Last Update：2024-01-02 23:10:35
ACETAMINOPHEN IMPURITY K - Preparation Method
Open Data Verified Data
The p-nitrophenol may be reduced by adding iron in hydrochloric acid.
Last Update：2022-01-01 09:27:06
ACETAMINOPHEN IMPURITY K - Use
Open Data Verified Data
It is used as an analytical reagent, an antioxidant, an oil additive, a dye, a medicine, and a photographic developer.
Last Update：2022-01-01 09:27:06
ACETAMINOPHEN IMPURITY K - Safety
Open Data Verified Data
rat oral LD50:375mg/kg; Mouse oral LD50: 420mg/kg. Irritating. Can be absorbed through the respiratory tract and skin poisoning. The staff should be protected and the working environment should be well ventilated. Store in a cool, ventilated warehouse.
Last Update：2022-01-01 09:27:06
ACETAMINOPHEN IMPURITY K - Reference Information
| Decomposition | 284 °C |
| LogP | -0.09-0.04 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Aminophenol | Aminophenol is also called hydroxyaniline and aminohydroxybenzene. There are 3 isomers, namely o-aminophenol, m-aminophenol, and p-aminophenol (4-aminophenol). In 1874, Baeyer and others first produced p-aminophenol. Due to the different relative positions of hydroxyl and amino groups, the physical and chemical properties of the three are also different. This product is weakly alkaline, weakly acidic and highly reducible. Because it has two groups of amino and phenol at the same time, it has the commonality of both. It is very unstable in air and daylight, especially in humid air, which is sensitive to oxygen, especially the ortho and para positions are more likely to be oxidized to deepen the color, mainly the formation of aminophenoxazine derivatives after oxidation. The main use of aminophenol is as a dye intermediate and photographic developer. Can produce acid dyes, direct dyes, sulfide dyes, azo dyes, mordant dyes and fur dyes. M-aminophenol and p-aminophenol are raw materials for medicine, herbicides, fungicides, pesticides and heat-sensitive pigments. O-aminophenol is also used as an inhibitor of metal alkaline corrosion, hair dye, rubber anti-aging agent, antioxidant, stabilizer, petroleum additive, catalyst for organic reaction, chemical reagent (m-aminophenol is gold and silver verification reagent), intermediates for organic synthesis, etc. |
| p-aminophenol | p-aminophenol is a fine chemical product intermediate commonly used in China at present. it is used to synthesize weak acid yellow 6G, weak acid light yellow 5G, vulcanized dark blue 3R, vulcanized blue CV, vulcanized brilliant green GB, vulcanized red brown B3R, vulcanized reduced black CLG, etc. Used in the pharmaceutical industry to synthesize paracetamol, Antoine, etc. It is also used to prepare products such as developers, antioxidants and petroleum additives. p-aminophenol, also known as 4-aminophenol, p-hydroxyaniline, 4-amino-1-hydroxybenzene, 4-hydroxyaniline, has two types: those precipitated from water, ethanol and ethyl acetate are α-type, white to light yellow orthorhombic flake crystals; those precipitated from acetone are biconical crystals. Strong reducibility, easy to be oxidized by air, gray-brown in light and in the air, especially in wet air. The melting point is 189.6~190.2 ℃, and it can be sublimated without decomposition at 110 ℃(1.467 × 103Pa). Boiling point 284 (decomposition). Slightly soluble in benzene, chloroform and petroleum ether, soluble in ethanol, ether and water. Solubility in water: 1.1 at 0.0 ℃, 3.01 at 59.0 ℃, 6.44 at 77.0 ℃, 10.09 at 86.7 ℃, 19.53 at 96.6 ℃, and 33.42 at 102.0 ℃. It quickly turns brown after dissolving in lye. Reacts with inorganic acids to form water-soluble salts. The aqueous solution is purple when it meets ferric chloride or sodium hypochlorite. This product is oxidized with silver oxide in ether to form quinone imine, and when oxidized with lead dioxide or silver nitrate, p-benzoquinone is generated. React with excess chlorine to produce polychloroquinone. When sulfonated with fuming sulfuric acid, 4-aminophenol-2-sulfonic acid is produced. Under mild conditions, when acylated with acetic anhydride, N-acetylphenol is formed. Reacts with sodium nitrite and can be diazotized. Rat oral LD501270mg/kg. p aminophenol is mainly used to make paracetamol, an antipyretic and analgesic drug. Manufacture vulcanized dye vulcanized new blue FBL, vulcanized blue CV, vulcanized brilliant green GB, vulcanized red brown B3R, vulcanized reduced black CLG, vulcanized dark blue 3R, fur dye fur brown P, etc. It is used to synthesize polymer stabilizer 4-hydroxydiphenylamine, N,N′-diphenyl -1, 4-phenylenediamine, N-(4-hydroxyphenyl)-2-naphthylamine, etc. Photographic developer N-methyl p-aminophenol and the like can also be manufactured. |
| Preparation method | p-nitrochlorobenzene is hydrolyzated in sodium hydroxide to form sodium p-nitrophenol, and after acidification, it is reduced with iron powder to obtain 4-aminophenol. sodium hydroxide is prepared into a solution with a concentration of 137~140g/L in an alkali mixing kettle, then it is added into the hydrolysis kettle, molten p-nitrochlorobenzene is added, heated to 152 ℃, the pressure in the kettle is 0.4~0.42MPa (gauge pressure), heating is stopped, the heat released by the hydrolysis reaction increases the temperature and pressure to 165 ℃, 0.6MPa (gauge pressure), and the reaction lasts for 3 hours, sampling analysis, make the oily distillate add water and 98% concentrated sulfuric acid into the first crystallization kettle, then press into the hydrolysate, cool to 50~55 ℃, add concentrated sulfuric acid, make the Congo red test paper purple, continue to cool to 30 ℃, and filter into the centrifuge for dehydration. add the last batch of p-aminophenol refined and filtered mother liquor into the reduction kettle, heat to 90 ℃, add iron powder and 30% hydrochloric acid, add iron powder and p-nitrophenol alternately in boiling state, and add cold refined filter mother liquor depending on the reaction (such as when overflowing the pot). Boiling reduction to the end point (reaction droplets on white filter paper, infiltration ring should be colorless). Add a certain amount of hot refined mother liquor, and add magnesium oxide until there are no iron ions in the reaction liquid. Let stand for 30 minutes, release the supernatant, and the lower iron mud is beaten with 98 ℃ crystallization filtration mother liquor, filtered, and the filtrate is injected into the second crystallization kettle. in the second crystallization kettle in 4 hours to 60~65 ℃, put into the third crystallization kettle in 4 hours to continue to cool to 25 ℃, maintain 30 minutes, centrifugal filtration. prepare sodium bisulfite solution with SO2 content of 4% ~ 5% in a refining kettle, add crystal filtered filter cake, stir for 1.5 hours, centrifuge filter, filter cake is dried by negative pressure air flow to obtain p-aminophenol finished product, and the refined mother liquor is recycled during reduction in the next batch. |
| toxicity and protection | toxic, p-aminophenol has the dual toxicity of aniline and phenol. It can be absorbed through the skin and cause dermatitis, which can cause methemoglobin and asthma. Its hydrochloride touches the skin and can cause severe itching or eczema. The cat subcutaneous injection of LD50 37mg/kg. |
| use | it is used to produce dyes such as blue sulfide FBG, weakly acidic light yellow 5G, paracetamol, antoin and other drugs, and also used to make developers, antioxidants, etc. used as analytical reagents this product is an intermediate of fine chemicals such as medicine and dyes. Used in the production of drug paracetamol, azo dyes, sulfide dyes, acid dyes, fur dyes, as well as developers, antioxidants and petroleum additives. It is widely used in the synthesis of medicines, dyes and other organic products, mainly used in the synthesis of paracetamol, antoone, vitamin B1, compound nicotinamide, etc. Used as raw material, antioxidant and developer for medicine and dyes Verification of gold, determination of copper, iron, magnesium, vanadium, nitrite and cyanate, antioxidant. |
| production methods | include iron powder reduction method, phenol nitrosation method, coupled reduction method, etc. 1. Iron powder reduction method is obtained by reduction of p-nitrophenol. Raw material consumption quota: nitrophenol (industrial product) 1388 kg/t, iron powder 1778 kg/t, 30% hydrochloric acid 200 kg/t. 2. Phenol nitrosation method is obtained by nitrosation, reduction and acid precipitation of phenol. 3. The coupling reduction method uses aniline as raw material and is obtained by diazotization, coupling and iron powder reduction. 4. Nitrobenzene catalytic hydrogenation method mostly uses platinum, palladium or both as catalysts, hydrogenated and reduced to phenylhydroxylamine in 10-20% sulfuric acid aqueous solution, and then transposed to p-aminophenol with a yield of 70-80%. Adding surfactants to the reaction system has a certain effect on improving the yield. 5. Nitrobenzene electrolytic reduction method Japan Mitsui East Pressure Fine Chemicals Company adopts electrolytic reduction of nitrobenzene in sulfuric acid solution and translocation of phenylhydroxylamine to p-aminophenol. In June 1977, the company built a 1000-ton/year device in Omuta Factory. |
| category | toxic substances |
| toxicity classification | highly toxic |
| acute toxicity | oral administration-rat LD50: 375 mg/kg; Abdominal cavity-mouse LDL0: 100 mg/kg |
| stimulation data | skin-rabbit 12.5 mg/24 hours mild; Eye-rabbit 100 mg mild |
| flammability hazard characteristics | open flame is combustible; heated decomposition; combustion releases toxic nitrogen oxide smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidants and food additives |
| fire extinguishing agent | carbon dioxide, foam, dry powder, sand, mist water. |
| occupational standard | STEL 1 mg/m3 |
| spontaneous combustion temperature | >250°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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Raw Materials for ACETAMINOPHEN IMPURITY K
Downstream Products for ACETAMINOPHEN IMPURITY K