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Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA

Butylated hydroxyanisole

CAS: 25013-16-5

Molecular Formula: C11H16O2

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Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA - Names and Identifiers

Name Butylated hydroxyanisole
Synonyms BHA
BOA
Vertac
antioxyne b
Butyl Hydroxyanisole
2-butyl-6-methoxyphenol
tert-butylhydroxyanisole
Butylated hydroxyanisole
Butylated hydroxy anisole
tert-butyl-4-methoxyphenol
tert-butyl-4-hydroxyanisole
tert-BUTYLHYDROXYANISOLE TECH
2(3)-tert-Butyl-4-hydroxyanisole
2(3)-t-Butylhydroquinone monomethyl ether BHA
butylhydroxyanisole standard(mixture of isomers)
tert-Butyl-4-hydroxyanisole (mixture of 2- and 3-isomer)
Butylated hydroxyanisoleBHA2(3)-tert-Butyl-4-methoxyphenol3(2)-tert-Butyl-4-hydroxyanisole
Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA
CAS 25013-16-5
EINECS 246-563-8
InChI InChI=1/C11H16O2/c1-3-4-6-9-7-5-8-10(13-2)11(9)12/h5,7-8,12H,3-4,6H2,1-2H3
InChIKey WYEIRNDSZQKIDQ-UHFFFAOYSA-N

Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA - Physico-chemical Properties

Molecular FormulaC11H16O2
Molar Mass180.24354
Density0.9976 (rough estimate)
Melting Point58-60°C(lit.)
Boling Point264-270°C
Flash Point>230°F
Water Solubility<0.1 g/100 mL at 18.5 ºC
Solubility Insoluble in water, soluble in oil, ethanol, glycerin, propylene glycol
Vapor Presure0.004mmHg at 25°C
Vapor Density6.2 (vs air)
AppearanceWhite to yellowish crystalline or waxy solid
ColorWhite to pale yellow
Merck14,1547
Storage Condition2-8°C
StabilityStable, combustible. Incompatible with oxidizing agents, ferric salts. Degrades on long exposure to sunlight.
SensitiveEasily absorbing moisture
Refractive Index1.4910 (estimate)
MDLMFCD01779059
Physical and Chemical PropertiesWhite to yellowish crystalline or waxy solid, with slight special odor. The melting range was 48-63 ℃. Boiling point 264~270 ℃(97709). Long-term storage with yellow-brown. Can be compressed into a cylinder weighing several grams. Insoluble in water. Soluble in ethanol (25g/100ml,25 ℃), glycerol (1g/100ml,25 ℃), lard (50g/100ml,50 ℃), corn oil (30g/100ml,25 C), peanut oil (40g/100ml,25 C) and propylene glycol (50g/100ml,25 C). The antioxidant effect of 3-BHA was 1.5~2 times stronger than that of 2-BHA. The antioxidant effect of 0.02% was increased by 0.01% than that of 10%, but the effect was decreased when the dosage was more than 0.02%.
UseUsed as a food antioxidant

Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA - Risk and Safety

Hazard SymbolsXn - Harmful
Harmful
Risk CodesR22 - Harmful if swallowed
R40 - Limited evidence of a carcinogenic effect
R36/37/38 - Irritating to eyes, respiratory system and skin.
R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
Safety DescriptionS36/37 - Wear suitable protective clothing and gloves.
S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection.
S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. 
S29 - Do not empty into drains.
UN IDs2811
WGK Germany2
RTECSSL1945000
TSCAYes
HS Code29093090
ToxicityLD50 in mice, rats (mg/kg): 2000, 2200 orally (Lehman)

Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA - Upstream Downstream Industry

Raw MaterialsHydroquinone
Phosphoric acid
Dimethyl sulfate
tert-Butanol
Zinc

Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA - Reference

Reference
Show more
1. Chen Xiaoli, Wang Shuhui, Zhu Junxiang, et al. Study on the stability of fucoxanthin in water and oil model systems [J]. Food Industry Science and Technology, 2016, 37(14).
2. Xu Binen, Huang Linyan, Yang Cuiping, et al. Extraction and separation of isoflavones from Douchi and their ability to scavenge DPPH free radicals [J]. Journal of Guizhou University of Traditional Chinese Medicine, 2020, v.42; no.195 (03):95-98 107.
3. Wang Fangmei, zhangxin, Gu Panpan, et al. Study on Oxidation Stability and Shelf Life Forecast of Xinjiang Melon Seed Oil [J]. Food and Fermentation Industry, 2019, 45(05):168-173.
4. Li Huantong, Xu Zewen, Guo Xiaomin, et al. Study on Antioxidation of Rosemary Extract to Perilla Seed Oil [J]. Food Science and Technology, 2020, v.45;No.341(03):223-228.
5. Wang Liang, Gu Panpan, Wang Fangmei, et al. Study on Oxidation Stability of Black Fruit and Wolfberry Seed Oil [J]. China Oil, 44(10).

Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA - Nature

Open Data Verified Data

white or yellowish waxy crystalline powder with specific phenolic odor and pungent odor. It is quite stable to heat, and the color becomes darker for a long time, and it is more stable under weak alkaline conditions. Soluble in ethanol (25g/lOOmL,25 ℃), propylene glycol (50g/lOOmL,25 ℃), lard (50g/lOOmL,25 ℃), corn oil (30g/lOOmL,25 degrees C) and some vegetable oils, etc., do not dissolve in water.

Last Update：2024-01-02 23:10:35

Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA - Preparation Method

Open Data Verified Data

It is prepared by diazotization in the presence of sulfuric acid, filtration, hydrolysis and distillation with p-aminovanisole and sodium sulfite as raw materials. Alternatively, the solvent benzene, tert-butyl alcohol and p-hydroxyanisole are successively added to the reaction kettle for heating and dissolution, reacted under the action of a catalyst, and washed, distilled and recrystallized to obtain a finished product.

Last Update：2022-01-01 10:08:44

Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA - Introduction

A pungent odor with a specific phenolic odor. Leather aroma, insoluble in water, soluble in oil, ethanol, glycerin, propylene glycol. It is quite stable to heat and is not easy to destroy under weakly alkaline conditions.
Last Update：2022-10-16 17:15:17

Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA - Use

Open Data Verified Data

fat-soluble antioxidant. Used as a food antioxidant, can hinder the oxidation of fat food, delay the time of food start spoilage. Its maximum amount in food should not exceed 0.2g/kg in terms of fat. When the dosage was 0. 02%, the antioxidant effect was 0.01% higher than that of 10%, but decreased when the dosage was more than 0. 02%. Butylated hydroxyanisole mixed with other fat-soluble antioxidants such as butylated hydroxytoluene, the effect is better. It can also be used as an antioxidant in cosmetics, which can play an antioxidant role in acids, hydroquinone, methylthioamino acids, lecithin and sulfurized dipropionic acid. It can also be used as an antioxidant for feed.

Last Update：2022-01-01 10:08:44

Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA - Safety

Open Data Verified Data

mouse, rat oral LD50:2000mg/kg, 2200mg/kg.

Last Update：2022-01-01 10:08:45

Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA - Reference Information

FEMA2183 | BUTYLATED HYDROXYANISOLE
(IARC) carcinogen classification 2B (Vol. 40, Sup 7) 1987
EPA chemical information Information provided by: ofmpub.epa.gov (external link)
toxicity ADI 0~0.5(FAO/WHO,2001). LD50 2.2~5 g/kg (rat, oral). GRAS(FDA § 182.3169;2000). In 1981, Japan conducted a feeding test on rats for two years and found that there was cancer in the front stomach. It is no longer allowed in Japan.
usage limit GB 2760-96(g/kg): candy essence 0.1 edible fat, fried food, dried fish products, biscuits, instant noodles, instant noodles, canned nuts, cured meat products, 0.2%; Breakfast cereal 0.:(single use or combined with BHT); Gum gum base, GMP is limited. FAO/WHO(1984,mg/kg): General edible oil 200 (used alone or combined with BHT, TBHQ and gallate esters, gallate esters shall not exceed 100; Provisional); Margarine 100 (used alone or combined with BHT and gallate esters; Provisional); Milk fat 200 (used alone or combined with BHT and gallate esters, gallate esters shall not exceed 100, shall not be used for direct consumption, nor for the preparation of milk and its products). FDA § 172.110(mg/kg): dehydrated potato pieces, slices, breakfast cereals, sweet potato chips 50; Shortening stabilizer 200; Potato diced 10 (both based on the total amount of BHA and BHT). Active dry yeast 1000, drinks and sweets made from dry products 2, dry coated fruit cubes 32, solid drinks and sweets 90. FDA 172.515: Volatile Oil 0.5% Containing Aromatic Substances. FDA § 172.615: Gum Sugar 0.1%. FDA § 173.340: Defoamer 0.1%. FDA § 181.24: Mobility of food packaging 0.005N. FDA § 182.3169: 0.02% of the amount of fats and oils (including volatile oils) in food. USDA § 318.7: Dry sausage 0.003%, refined animal oil 0.01%, margarine 0.02% (combined with other antioxidants). USDA § 381.147: Poultry 0.01%, measured by fat. 4-EEC-HACSG .. shall not be used in infant food unless vitamin A is supplemented.
Use Antioxidant, the antioxidant effect of 3-BHA added to food is 1.5-2 times stronger than 2-BHA, but the mixture of the two has a certain synergy Therefore, a mixture containing a high proportion of 3-BHA has almost the same effect as pure 3-BHA. BHA can interact with the peroxide produced in the oxidation process of grease to cut off the chain reaction of automatic oxidation of grease and prevent grease from continuing to oxidize. BHA is mixed with other antioxidants and synergist citric acid, etc., and its antioxidant effect is more significant. In addition to antioxidant effect, BHA also has quite strong antibacterial power and anti-mildew effect. As a food additive, it is used as an antioxidant for oil, lard, salted fish shellfish, dried fish shellfish products, pretzel biscuits, fried potato slices, instant noodles, fried snacks, etc. Also used as feed additive and gasoline additive. 3-tert-butyl-4-hydroxyanisole (2-BHA) is also used as a biochemical reagent.
used as food antioxidant
this product is an oil-soluble antioxidant widely used at home and abroad. the antioxidant capacity of 3-BHA is l.5 ~ 2 times that of 2-BHA, and the mixture of the two has a certain synergistic effect. Mixed with other oxidants or combined with synergist citric acid, the antioxidant effect is more significant. China stipulates that it can be used for edible oils, fried foods, biscuits, instant noodles, quick-cooked rice, canned nuts, dried fish products and cured meat products, with a maximum usage of 0.2 g/kg (the maximum usage is based on fat); Mixed with BHT, the total amount shall not exceed 0.2 g/kg; When mixed with BHT and PG, the total amount of BHA and BHT shall not exceed 0.1 g/kg and PG shall not exceed 0.05 g/kg. This product also has quite strong antibacterial effect, and is effective against most bacteria and molds.
Butyl hydroxyanisole can be used as a feed antioxidant and also has an antibacterial effect. The amount of BHA 250mg/kg can inhibit the production of aflatoxin, 200mg/kg BHA can completely inhibit the growth of spores such as toxic enzymes and Aspergillus niger in food and feed.
butyl hydroxyanisole as fat soluble antioxidant, suitable for fat food and fat rich food. Due to its good thermal stability, it can be used under frying or baking conditions. In addition, butyl hydroxyanisole has a strong antioxidant effect on animal fats, but has a poor antioxidant effect on unsaturated plant fats. Butyl hydroxyanisole can stabilize the pigment of raw beef and inhibit the oxidation of ester compounds
production method (1) preparation of intermediate p-hydroxyanisole. It can be prepared by alkylation with hydroquinone as the raw material. Here, the synthesis method of p-aminoanisole as the raw material is given: p-aminoanisole and sodium nitrite (molar ratio 1:1:15) are added to the reaction kettle and diazotized in the presence of sulfuric acid. After the reaction is completed, keep the temperature and filter, and slowly add the filtrate to hot water for hydrolysis. The resulting p-hydroxyanisole is immediately extracted with steam, condensed and extracted with organic solvent benzene. The solvent is removed by concentrated distillation to obtain a product with an average yield of 84.7%. (2) Synthesis of BHA. Solvent benzene, tert-butanol and p-hydroxyanisole are successively added to the reaction kettle to heat and dissolve, then catalyst phosphoric acid or sulfuric acid is added, and reflux reaction is carried out under strong stirring at 80 ℃. After the reaction is completed, let the material stand and delaminate. The organic phase was washed with 10% sodium hydroxide solution and water until neutral. The solvent is removed by distillation, and then the finished product is recrystallized by ethanol.
1 preparation of intermediate p-hydroxyanisole p-aminoanisole and sodium nitrite are added to the reaction kettle according to 1:1.15, and diazotization is carried out in the presence of sulfuric acid; after the reaction is completed, heat preservation and filtration are carried out, and the filtrate is slowly dropped into hot water for hydrolysis; the generated p-hydroxyanisole is immediately extracted with steam, condensed and extracted with benzene; the solvent is removed to obtain the product, and the average yield is 84.7%. CH3OC6H4NH2 + NaNO2[H2SO4]→ CH3OC6H4N2HSO4[H2O]→ Synthesis of CH3OC6H4OH 2BHA Solvent benzene, tert-butanol and p-hydroxyanisole are successively added to the reaction kettle for heating and dissolution, then catalyst phosphoric acid or sulfuric acid is added, and reflux reaction is strongly stirred at 80 ℃; After the reaction is completed, the material is discharged and left to layer; The organic phase is washed with 10% sodium hydroxide solution and water to be neutral, the solvent is removed, and the finished product is obtained by recrystallization with ethanol.
Hydroquinone reacts with tert-butanol under the catalysis of phosphoric acid to generate 2-tert-butyl hydroquinone and 3-tert-butyl hydroquinone, and then reacts with dimethyl sulfate in the presence of zinc powder. Another method is made by reacting p-hydroxyanisole with tert-butanol at 80 ℃ with phosphoric acid or sulfuric acid as a catalyst. The reaction product is washed with water, washed with 10% sodium hydroxide solution, distilled under reduced pressure, and recrystallized to obtain the finished product.
It is obtained by reacting p-hydroxyanisole with phosphoric acid or sulfuric acid as a catalyst and tert-butanol at 80°C. Hydroquinone is reacted with tert-butanol to produce 2-tert-butanol hydroquinone, and then zinc powder is used as a catalyst to react with dimethyl sulfate to form a crystalline compound.
category toxic substances
toxicity classification poisoning
acute toxicity oral-rat LD50: 2000 mg/kg; Oral-mouse LD50: 1100 mg/kg
flammability hazard characteristics thermal decomposition discharges spicy and irritating smoke
storage and transportation characteristics warehouse ventilation and low temperature drying
fire extinguishing agent water, dry powder, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent
auto-ignition temperature 599 °F
toxic substance data information provided by: pubchem.ncbi.nlm.nih.gov (external link)
Last Update：2024-04-10 22:29:15
Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA
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Tel: 18301782025
Email: 3008007409@qq.com
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Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA
Raw Materials for Butylated hydroxyanisole,2(3)-t-Butyl-4-hydroxyanisole, 2(3)-t-Butylhydroquinone monomethyl ether, BHA
Hydroquinone
Phosphoric acid
Dimethyl sulfate
tert-Butanol
Zinc
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