2-Phenylacetic acid
Phenylacetic acid
CAS: 103-82-2
Molecular Formula: C8H8O2
2-Phenylacetic acid - Names and Identifiers
| Name | Phenylacetic acid |
| Synonyms | phenylacetate à-tolylic acid a-Tolylic Acid α-tolylic acid Phnylaceticacid benzenaceticacid Phenylacetic acid alpha-Toluic acid Phenoxacetic acid Benzeneacetic acid alpha-Tolylic acid 2-Phenylacetic acid sodium phenylacetate PhenylaceticAcidC8H8O2 ammonium phenylacetate PhenylaceticAcidPuriss PHENYLACETICACID,REAGENT calcium bis(phenylacetate) 2-oxo-3-phenylpropanoic acid |
| CAS | 103-82-2 |
| EINECS | 203-148-6 |
| InChI | InChI=1/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10) |
2-Phenylacetic acid - Physico-chemical Properties
| Molecular Formula | C8H8O2 |
| Molar Mass | 136.15 |
| Density | 1.081g/mLat 25°C(lit.) |
| Melting Point | 76-78°C(lit.) |
| Boling Point | 265°C(lit.) |
| Flash Point | 132°C |
| JECFA Number | 1007 |
| Water Solubility | 15 g/L (20 ºC) |
| Vapor Presure | 1 mm Hg ( 97 °C) |
| Vapor Density | ~4 (vs air) |
| Appearance | neat |
| Specific Gravity | 1.081 |
| Color | Leaflets on distillation in vac; plates, tablets from pet ether |
| Odor | disagreeable odor of geranium |
| Merck | 14,7268 |
| BRN | 1099647 |
| pKa | 4.28(at 18℃) |
| PH | 3.7(1 mM solution);3.17(10 mM solution);2.66(100 mM solution) |
| Storage Condition | Store at RT. |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.5120 (estimate) |
| Physical and Chemical Properties | White patchy, shiny crystals. Special odor. melting point 76.5 ℃ boiling point 265.5 ℃ relative density 1.091 solubility slightly soluble in cold water, soluble in ethanol, ether and acetone, also soluble in sodium carbonate and ammonia solution. |
| Use | Is an important raw material for the synthesis of medicines, pesticides and spices |
2-Phenylacetic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
| UN IDs | UN 3335 |
| WGK Germany | 1 |
| RTECS | AJ2430000 |
| FLUKA BRAND F CODES | 13 |
| TSCA | Yes |
| HS Code | 29163400 |
| Toxicity | LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
2-Phenylacetic acid - Upstream Downstream Industry
2-Phenylacetic acid - Nature
Open Data Verified Data
white flake-like, shiny crystals. Flammable. Special odor. The relative density was 1. 091. Melting point 76.5 °c. Boiling point 265.5 °c. Slightly soluble in cold water, soluble in ethanol, ether and acetone, also soluble in sodium carbonate and ammonia solution.
Last Update：2024-01-02 23:10:35
2-Phenylacetic acid - Preparation Method
Open Data Verified Data
with toluene as raw material, through chlorine to generate benzyl chloride, by cyanation to generate phenylacetonitrile, and then by hydrolysis, acidification to obtain phenylacetic acid, the product by static stratification, vacuum dehydration, filtration, drying, finished product.
Last Update：2022-01-01 10:43:31
2-Phenylacetic acid - Use
Open Data Verified Data
It is used to improve the total yield of penicillin G in the penicillin production process, and is also used as a raw material for spices, pesticides and plant growth regulators.
Last Update：2022-01-01 10:43:30
2-Phenylacetic acid - Safety
Open Data Verified Data
- This product has strong toxicity to bacteria, and the oral LD50 of mice is 100 ~ 150mg/kg. In the human body can be detoxified by glucuronic acid. Bactericidal than bromophenylacetic acid is strong, weaker than O-bromophenylacetic acid.
- The bag is packed in plastic bag, and each bag is 25kg. According to the provisions of the storage and transportation of chemicals.
Last Update：2022-01-01 10:43:31
2-Phenylacetic acid - Reference Information
| FEMA | 2878 | PHENYLACETIC ACID |
| LogP | 0.811 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| content analysis | after the sample is dried in a sulfuric acid dryer for 3 hours, 500mg is accurately weighed and dissolved in 25ml of 50% ethanol solution with 0.1mol/L sodium hydroxide solution and phenolphthalein test solution (TS-167) as indicator. Then titrate to pink with 0.1mol/L sodium hydroxide solution. 0.1mol/L sodium hydroxide solution per ml is equivalent to phenylacetic acid (C8H8O2)13.62mg. |
| toxicity | GRAS(FEMA). LD50 2250mg/kg (rat, oral). |
| usage limit | FEMA(mg/kg): soft drink 1.8; Cold drink 5.3; Candy 5.9; Baked food 12; Pudding 27; Gum candy 5.4~11; Wine 0.10; Syrup 0.10. Moderate limit (FDA § 172.515,2000). |
| use | is an important raw material for synthetic medicines, pesticides and spices GB 2760-1996 regulations are allowed to use edible spices. It is mainly used to prepare cream, chocolate, peach, strawberry, vanilla bean, honey and beer and other flavors. It is also used for tobacco (especially Havana cigar) flavors. Phenylacetic acid is an intermediate in organic synthesis of medicines, pesticides, spices, etc. It is used in the production of penicillin, dibazole and other drugs in the pharmaceutical industry. Phenylacetic acid is chlorinated and esterified to obtain α-chlorophenyl ethyl acetate, which is used in the production of Inaba Fengsan and Ethyl Inaba Fengsan. These two pesticides are broad-spectrum organophosphorus pesticides. Phenylacetic acid itself is also a pesticide plant growth stimulating hormone. Phenylacetic acid is widely found in grapes, strawberries, cocoa, green tea, honey, etc. Phenylacetic acid has a sweet honey taste at low concentrations, and still has a sweet taste below 1ppm. It is an important spice component. Phenylacetic acid also has a strong bactericidal effect. Used in the perfume, pharmaceutical industry, and also used as plant growth hormone is the most commonly used acid perfume. It is a spice for preparing artificial civet balm. It is the main body of honey essence. It can also be used for hair essence and soap essence. It can also be used in appropriate amounts in edible flavors and tobacco flavors. Phenylacetic acid is an intermediate of the fungicide Benzouling, the insecticide Daofengsan, the rodenticide diphtherone, and chlorderone. |
| production method | the preparation method is to hydrolyze phenylacetonitrile by acid, I .e. 70% sulfuric acid is put into a reaction kettle, phenylacetonitrile is added dropwise under stirring, reacted at 130 ℃ for 2 hours, diluted with water, stratified, separated from ammonium bisulfate solution, and dehydrated at 120~130 ℃ to obtain the product. Phenylacetic acid can also be basic hydrolyzed with phenylacetonitrile, I .e. adding phenylacetonitrile with caustic soda solution at 115 ℃, reacting at 125~133 ℃ for 3h, refluxing at 120~124 ℃ for 3h, then cooling, diluting with water, neutralizing with hydrochloric acid until pH = 6.5~7, flocs are precipitated, activated carbon is added for decolorization, the filtrate is adjusted to pH = 2~3, cooled to 5 ℃, and crystallized, filter the dried product. It is obtained by hydrolysis of phenylacetonitrile. 52.6kg of 70% sulfuric acid is added to the reaction pot, stirred and heated to about 100 ℃, phenylacetonitrile is slowly added dropwise, 40kg is dripped within 1h, then the temperature is raised to 130 ℃, and the heat preservation reaction is continued for 2h. Then 8kg of water was added, the hydrogen sulfate produced by the reaction was diluted, and the ammonium bisulfate mother liquor was separated into layers, and dehydrated under reduced pressure at 120-130 ℃ for 1h to obtain phenylacetic acid with a purity of 96-97% and a yield of 95-97%. The hydrolysis reaction of phenylacetonitrile can also be carried out in sodium hydroxide solution, refluxing at 100-104 ℃ for 6 hours until the oily liquid is reduced, cooling to 5 ℃, adding hydrochloric acid to adjust the pH to 1-2, filtering, The filter cake is washed with water, and dried at 40 ℃ to obtain phenylacetic acid. More than 90% domestic manufacturers use phenylacetonitrile hydrolysis to produce phenylacetic acid. The chemical plant of Wuhan University adopts the carbonyl synthesis process and uses chlorobenzyl carbonylation to produce phenylacetic acid, which is basically pollution-free, low cost and energy saving. Raw material consumption quota: toluene 2200 kg/t, liquid chlorine (99%)1500 kg/t, sodium cyanide 800 kg/t, sulfuric acid (98%)1500 kg/t, liquid alkali (30%)2500 kg/t. It is obtained by hydrolysis of benzyl cyanide and dilute sulfuric acid. |
| category | flammable liquid |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 2250 mg/kg; Oral-mouse LD50: 2250 mg/kg |
| explosive hazard characteristics | solvent vapor mixed with air can explode |
| flammability hazard characteristics | solvent flammable |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from oxidant storage and transportation |
| fire extinguishing agent | dry powder, carbon dioxide, sand, soluble foam |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:46
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Raw Materials for 2-Phenylacetic acid
Downstream Products for 2-Phenylacetic acid
Propiophenone
Phenylacetone
Phenylacetyl chloride
Amitriptylinehydrochloride
Cyproheptadine hydrochloride
P-cresyl phenylacetate
Phenylacetone
Phenylacetyl chloride
Amitriptylinehydrochloride
Cyproheptadine hydrochloride
P-cresyl phenylacetate