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Vanillin CAS 121-33-5

Molecular Formula: C8H8O3

Formula Weight: 152.15

ZSpharmac: Vanillin Supplement

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Product Name: Vanillin
CAS No: 121-33-5
Purity: 99%

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Basic Info

Product Name:Vanillin
Other Names:3-Methoxy-4-Hydroxybenzaldehyde
CAS:121-33-5
Place of Origin:Shandong, China
Brand Name:ZSpharmac
Type:Cosmetic Raw Materials
Appearance:White to Pale Yellow Crystalline Powder
EINECS No.:204-465-2
Storage:2-8°C
Provide:Vanillin MSDS;
Vanillin COA

What is Vanillin?

Vanillin is frequently referred to as vanilla powder, vanillin, vanillin powder, vanilla essence, vanillin, an essential flavor extracted from the rutaceae plant vanilla bean, and is among one of the most effective ranges of synthetic seasonings. It is a crucial raw material for the prep work of delicious chocolate, ice cream, eating gum, cakes as well as cigarette tastes. Naturally found in vanilla vessels, in addition to in clove oil, oakmoss oil, Peruvian balsam, turmeric, and also benzoin.

Vanillin has a strong as well as one-of-a-kind vanilla bean fragrance, stable aroma, and also is not easily volatile at greater temperature levels. It is conveniently affected by light, progressively oxidizes in the air, as well as is very easy to change shade when it comes across antacids or alkaline materials. The aqueous option responds with ferric chloride to create a blue-violet option. It can be utilized in several everyday fragrance formulas, but it is mostly made use of in food tastes. Especially it is widely made use of in sweet, delicious chocolate, drinks, gelato, and alcohol, as well as it is likewise really valuable in tobacco tastes. IFRA has no restrictions. Nevertheless, it is simple to trigger staining, so treatment must be taken when using it in white fragranced products.

Vanillin is additionally an essential edible flavor, used as a foundation seasoning, used in almost all tastes, and is widely utilized in the food sector. As a food flavor, it is extensively made use of in bread, cream, gelato, brandy, and so on. The enhancement amount is 0.01-0.04%, and in candy, it is 0.02-0.08%. It is just one of one of the most secondhand spices in baked goods and is used in chocolate, cookies, cakes, desserts as well as gelato. For far better result, liquify in warm water prior to usage. The optimum usage is 220mg/kg for baked items and 970mg/kg for delicious chocolate. It is extensively made use of in cosmetic essences as fixatives, planners and conditioners. It is also an essential seasoning agent for drinks as well as foods. Additionally utilized in the manufacture of pharmaceutical L-dopa (L-dopa), methyldopa and so forth. It can also be used as a brightener for nickel and also chromium metal plating.

Vanillin Property

Melting point 

81-83 °C(lit.)

Boiling point 

170 °C15 mm Hg(lit.)

density 

1.06

vapor density 

5.3 (vs air)

vapor pressure 

>0.01 mm Hg ( 25 °C)

refractive index 

1.4850 (estimate)

Fp 

147 °C

storage temp. 

2-8°C

solubility 

methanol: 0.1 g/mL, clear

pka

pKa 7.396±0.004(H2O I = 0.00 t = 25.0±1.0) (Reliable)

form 

Crystalline Powder

color 

White to pale yellow

PH

4.3 (10g/l, H2O, 20℃)

Water Solubility 

10 g/L (25 ºC)

Vanillin Uses

  1. Vanillin is used as food taste, daily chemical taste and pharmaceutical intermediate.
  2. Vanillin is an excellent spice for acquiring powdery and also soy fragrances. Usually made use of as a foundation scent. Can be commonly made use of in almost all scent kinds, such as violet, turf orchid, sunflower, oriental scent. It can be combined with jasmine aldehyde, isoeugenol benzyl ether, coumarin, musk, and so on as a fixative, modifier and also mixture, and also can likewise be used to cover halitosis. It is also commonly used in edible and also cigarette tastes, as well as the dose is also large. It is a must-use flavor in vanilla bean, cream, delicious chocolate, as well as toffee tastes.
  3. Vanillin is an edible seasoning that is permitted to be made use of in my country. It can be made use of as a fixative and is the major basic material for the prep work of vanilla-type flavors. It can also be straight made use of for flavoring of biscuits, cakes, sweets, drinks as well as other foods. The dose is based upon normal manufacturing demands, usually 970mg/kg in delicious chocolate; 270mg/kg in chewing gum; 220mg/kg in cakes and also biscuits; 200mg/kg in sweet; 150mg/kg in condiments ~ 95mg/kg in cold beverages.
  4. Vanillin is a crucial artificial seasoning, extensively made use of in everyday chemical products for food, cigarette and also wine. It is utilized in a large quantity in the food sector. It is utilized to prepare flavors such as vanilla, delicious chocolate as well as lotion. The dose can get to 25-30%. Directly made use of in biscuits as well as cakes, the dose is 0.1-0.4%, cool beverages 0.01-0.3%, sweet 0.2-0.8%, especially dairy items. For analytical chemistry, screening healthy protein azaindene, phloroglucinol and tannic acid. In the pharmaceutical sector, it is made use of to generate the antihypertensive medication methyldopa, the catechol medicine dopa, along with the white naetine and also dijianjing, and so on.
  5. Vanillin was made use of as a common reagent for organic analysis.
  6. Vanillin is the standard for healthy protein, azaindene, phloroglucinol, tannin, iron ion, chlorine, flavor as well as fragrance from benzoic acid, and also methoxyl group by natural trace analysis.

Preparation of Vanillin

report one,
The synthetic procedure of stable isotope-labeled Vanillin is as follows:

Under ice-salt bath, dissolve 1.52g Vanillin, 360mg methanol-D4 and 2.62g triphenylphosphine in 10mL tetrahydrofuran solution, slowly dropwise (preferably one drop every 2s) azodiisopropyl ester in tetrahydrofuran solution (2.02g/5mL) ), the temperature was kept at 0~5 ℃, continued stirring for 60min after the dropwise addition, TLC (thin layer chromatography) spot plate monitoring, after the reaction was completed, the tetrahydrofuran solvent was removed by spinning off, and the column chromatography was separated to obtain formazan with a yield of 98%. The base vanillin-D3 is the product, and the obtained product has a chemical purity of 99.5% and an isotopic abundance of 99.9%.

report two,
In a 1-liter autoclave, 100.0 g (0.66 mol) of ortho-vanillin, 350 ml of ethyl acetate, and 6.0 g of 10% palladium on carbon were added. Start stirring at 400 rmp, replace the air in the kettle with nitrogen, and then replace the nitrogen with hydrogen. After the reaction was completed, the palladium carbon was filtered off, the solvent was recovered, and 89.4 g of 6-methylguaiacol (content 99.8%) was obtained by distillation under reduced pressure, and the yield was 98.0%. MS(EI), m/s, 138(M+, 89), 123.1(100), 95.2(19), 77.2(22), 67(13), 65(10), 39.2(9). 1H NMR (500 MHz, CDCI3) δ, 2.66 (3H, s, CH3), 3.88 (3H, s, OCH3), 5.68 (1H, s, OH), 6.70-6.78 (3H, m, ArH).

55.2g (0.40mol) of 6-methylguaiacol was added to the reaction flask 1, then 80.0g of 20% aqueous sodium hydroxide solution was added to dissolve it, and 62.2g (50%w of glyoxylic acid) was added to the reaction flask 2 /w, 0.42mol) solution and 80.0g of 20% aqueous sodium hydroxide solution; the reaction solutions of the two reaction flasks were combined, and 41.6g of 20% aqueous sodium hydroxide solution was added until the pH of the reaction system was 12.0. The reaction was carried out at 30°C for 12h. The total amount of the reaction mixture was 319.0 g, and by liquid phase analysis, 4-hydroxy-3-methoxy-5-methylmandelate was 20.8%, and the yield was 84.6%.

Into a 1-liter autoclave, 361.4 g of the synthesized reaction solution (containing 77.34 g of 4-hydroxy-3-methoxy-5-methylmandelate) and 6.2 g of catalyst CuO were added. Start stirring at 400 rmp, replace the air in the kettle with nitrogen, and then replace nitrogen with oxygen. The oxygen pressure is maintained at 0.15 MPa, and the reaction is carried out at 80 ° C for 6 h. After the reaction, the catalyst was filtered out, and the reaction solution was acidified to pH 3-4 with 50% aqueous sulfuric acid solution, and extracted with chloroform; chloroform was recovered and distilled to obtain 57.7 g of 5-methyl vanillin (content 99.5%) in a yield of 57.7 g. 87.5%.

Production Method of Vanillin

Vanillin can be prepared from lignin contained in sulphurous pulping waste liquor from paper mills. Generally, the waste liquid contains 10% to 12% of solids, of which 40% to 50% is calcium lignosulfonate. First, concentrate the waste liquid to a solid content of 40%-50%, add 25% NaOH of the amount of lignin, heat it to 160-175°C (about 1.1-1.2MPa), and oxidize it with air for 2 hours, and the conversion rate can generally reach 8% to 11% of lignin. The oxide is extracted with benzene to extract vanillin, and the benzene is recovered by steam distillation; sodium bisulfite is added to the oxide to generate bisulfite, which is then separated from impurities, and then decomposed with sulfuric acid to obtain crude vanillin. The finished product is obtained by distillation under reduced pressure and recrystallization.

Trichloroacetaldehyde method guaiacol and trichloroacetaldehyde are heated to 27 ℃ in the presence of soda ash or potassium carbonate to condense to form 3-methoxy-4-hydroxyphenyltrichloromethyl methanol. Famolin was removed by steam distillation. In the presence of caustic soda, use nitrobenzene as an oxidant and heat to 150 ℃ to oxidatively crack to obtain vanillin; Cu-CuO-CoCl2 can also be used as a catalyst for air oxidation at 100 ℃, and after the reaction, benzene is used to extract vanillin, The finished product is obtained by distillation under reduced pressure and recrystallization.
In the glyoxylic acid method, guaiacol, sodium hydroxide solution and sodium carbonate are sequentially added to the glyoxylic acid solution, and 3-methoxy-4-hydroxyphenyl glycolic acid is formed by condensation at 30-33 °C. After extracting the unreacted guaiacol with a solvent, adding sodium hydroxide solution, heating to 100°C in the presence of nitrobenzenesulfonic acid and calcium hydroxide for oxidative cracking to obtain vanillin. After neutralization of the oxidized product, vanillin is extracted with dichloroethane, and the crude product is purified by vacuum distillation and recrystallization to obtain the finished product. Nitroso method: Add 166kg of 30% hydrochloric acid and 200kg of water into the reaction kettle, and after cooling to 10°C, add 61.5kg of dimethylaniline dropwise within 2h, the temperature does not exceed 25%, and then continue to stir for 20min. After cooling to 6 ℃, add dropwise a 25% aqueous solution prepared by 75 kg of sodium nitrite, and keep stirring at 7~10 ℃ for 1 h. Filter out p-nitrosodimethylaniline hydrochloride, then add a certain amount of ethanol and concentrated hydrochloric acid to dilute the solid to obtain p-nitrosodimethylaniline.
Condensation of guaiacol and p-nitrosodimethylaniline: dissolve 26kg of urotropine in 34kg of water, add a mixture of 126kg of guaiacol and 63kg of ethanol, and store in a high-level tank for later use. The mixed Chemical 550kg of the above-mentioned p-nitrosodimethylaniline hydrochloride and ethanol was added to the reactor, and after being heated to 28°C, a metal salt catalyst was added, and then guaiac was added dropwise when being heated to 35~36°C. The temperature of the phenol mixture (3~3.5h) was kept at 40~43℃, and the stirring reaction was continued for 1h after the dropwise addition. Then add 100kg of water at 40°C to dilute, and stir for 15min. The content of vanillin in the condensate should be above 11%.
Using benzene as a solvent, the above-mentioned condensed liquid is continuously extracted in countercurrent in a rotating disk liquid-liquid extraction tower. The benzene extract contains a large amount of hydrochloric acid, which is first washed with water, and then neutralized to Ph=4 with alkali; benzene is recovered by distillation with a rising film evaporator, and then steamed for 1 hour to remove residual benzene; then evaporated under reduced pressure water, and finally the crude vanillin is quickly distilled at 120-150°C (666.6Pa), and the freezing point is about 70°C. The crude product was dissolved in toluene at 70°C, filtered and cooled to 18-20°C, filtered with suction and washed with a small amount of toluene to obtain vanillin. Then carry out the second vacuum distillation, collect the fractions at 130-140°C (266.6-399.9Pa) and dissolve them in dilute ethanol at 60-70°C, slowly cool to 16-18°C to crystallize (1h) . Filter by centrifuge and wash with a little dilute ethanol. Finally, at 50 ~ 60 ℃, hot air drying for 12h to obtain the finished product. According to guaiacol, the yield can reach more than 65%.

Using p-hydroxybenzaldehyde as raw material, vanillin was prepared by monobromination and methoxylation. Add 16g (0.131mol) of p-hydroxybenzaldehyde and 90mL of solvent to a 250mL flask, add 6.8mL (0.131mol) of liquid bromine after dissolving, and heat to 40~45℃ for 6h reaction. The solvent was suctioned under reduced pressure, the residue was boiled with water, filtered while hot, the filtrate was crystallized by cooling, filtere

d, and dried to obtain white crystals of 3-bromo-4-hydroxy-benzaldehyde with a melting point of 123-124°C and a yield of 90%.

12g (0.0597mol) of the above product, 45mL (0.230mol) of 28.24% sodium methoxide solution, 35mL DMF and 0.2g CuCl were added to a 250mL flask, and the reaction was carried out at 115°C for 1.5h. Then the solvent was extracted, the residue was acidified with 18% hydrochloric acid to Ph=4~5, extracted with hot benzene for 3 times, the water layer was separated, and the benzene layer was distilled under reduced pressure to remove the benzene to obtain a brown liquid. It was dissolved in hot dilute alcohol solution, cooled to precipitate white crystals, filtered and dried to obtain 8.3 g of vanillin, the melting point was 81-82°C, the purity was 99.5%, and the yield was 91.1%.

Company Profile and Corporate Culture

Company Profile:

ZhiShang Chemical is owned by ZhiShang Group is a professional new-type chemicals enterprise combined into research and development, production and sales .

The company’s competitive product is pharmaceutical raw materials and intermediates (especially carbohydrate derivatives Series), In recent years, the company has made a major breakthrough in food and feed additives, plant extraction, industrial chemicals industry .

The company insists on the spirit of “sincere management, strict quality control, customer as god” , get consistent high praise from customers at home and abroad.

Corporate Culture:

OUR MISSION
Help China Chemicals to benefit the happiness of human life
OUR VISSION
Become the most trusted chemical supplier in the world
OUR BUSINESS PHILOSOPHY
Striver – oriented, enrich employees, customer first, deep service, seek development
OUR VALUES
Be prepared for danger in times of peace, forge ahead actively, unity and cooperation, and be brave to fight

About Us

The production base is located in Zhangqiu chemical industry park and Tai’an high-tech chemical industry park. laboratory and workshop in strict accordance with the GMP standard and the product fit national ISO9001 and ISO2000 standards.

“Zhishang” products are exported to Europe, North and South America, the Middle East, Asia Pacific and Africa area, so as to establish a long-term and stable cooperation relationship with customer in the world.

Company Info
  • Business Type: Manufacturer
  • Product Range: Additive , Chemical Auxiliary & Catalyst , Organic Chemicals
  • Products/Service: Organic Intermediate,Inorganic Chemistry, APIs, Dyestuffs And Pigments, Fragrance And Spices, Food Additives
  • Total Employees: 51~100
  • Capital (Million US $): 10000000RMB
  • Year Established: 2016
Production Capacity
  • No. of Production Lines : 8
  • No. of QC Staff : 5 -10 People
  • OEM Services Provided : yes
  • Factory Size (Sq.meters) : 3,000-5,000 square meters
  • Certificate: ISO9001 , CE , GMP , API , MSDS
  • Factory Location : Diao Town Industry Park, Zhangqiu City, Jinan City, Shandong Province, China.

Service

Pre-Sales Service

* Prompt reply and 24 hours online, professional team to provide best price and high quality product.

* Sample testing support.

* Every batch of products will be tested to ensureits quality.

*The packing also can be according the customers` requirment.

*Any inquiries will be replied within 24 hours.

*we provide Commerical Invoice, Packing List, Bill of loading, COA , Health certificate and Origin certificate. If your markets have any special requirements, let us know.

 

After-Sales Service

*The fact of logistics information monitoring.

* Any questions about the product can be consulted at any time.

*Product has any problem can return.

FAQ

Do you accept sample order?

We will make samples before mass production, and after sample approved, we’ll begin mass production. Doing 100% inspection during production, then do random inspection before packing.

 

HOW TO CONFIRM THE PRODUCT QUALITY BEFORE PLACING ORDERS?

You can get free samples for some products,you only need to pay the shipping cost or arrange a courier to us and take the samples. You can send us your product specifications and requests,we will manufacture the products according to your requests.

What’s your MOQ?

Our MOQ is 1kg. But usually we accept less quantity such as 100g on the condition that sample charge is 100% paid.

Do you supply product report?

Yes. We’ll give you product analysis report before shipping.

  Is there a discount?

Different quantity has different discount.

Shipping

1. ≤50kg, Express delivery recommended, usually called as DDU service;

2. ≤500kg, Air shipping recommended, usually called as FOB, CFR, or CIF service;

3. >500kg, sea shipping recommended, usually called as FOB, CFR, or CIF service;

4. For high value products, please select air shipping and express delivery for safe.

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