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Fumaric acid

Acidity regulator Physical and chemical properties Chemical reaction Side Effects Content analysis Toxicity Usage limit Standards for Use of Food Additives Chemical properties Uses Production method

CAS No.110-17-8
Chemical Name:Fumaric acid
Synonyms:FA;TMEDA;U-1149;fumaric;NSC-2752;FEMA 2488;Fumarsure;boleticacid;FUMARSAEURE;Boletic acid
CBNumber:CB5852804
Molecular Formula:C4H4O4
Formula Weight:116.07
MOL File:110-17-8.mol
Fumaric acid Property
Melting point : 298-300 °C (subl.)(lit.)
density : 1.62
vapor pressure : 1.7 mm Hg ( 165 °C)
FEMA : 2488
Fp : 230 °C
Water Solubility : 0.63 g/100 mL (25 ºC)
Merck : 14,4287
BRN : 605763
Stability:: Stable at room temperature. Decomposes at around 230 C. Incompatible with strong oxidizing agents, bases, reducing agents. Combustible.
CAS DataBase Reference: 110-17-8(CAS DataBase Reference)
NIST Chemistry Reference: Fumaric acid(110-17-8)
Safety
Hazard Codes : Xi
Risk Statements : 36
Safety Statements : 26
RIDADR : UN 9126
WGK Germany : 1
RTECS : LS9625000
Hazardous Substances Data: 110-17-8(Hazardous Substances Data)

Fumaric acid Chemical Properties,Usage,Production

Acidity regulator
Fumaric acid is an important kind of organic chemical raw materials as well as the intermediate of fine chemical products. Meanwhile, it is also an important kind of derivatives of maleic anhydride, being widely used in food, coatings, resins and plasticizers. In the food industry, fumaric acid, used as souring agent, can be applied to soft drinks, western-style wine, cold drinks, fruit juice concentrate, canned fruit, pickles and ice cream. As an acidic substance used as solid beverage gas production agent, it has excellent bubble durability with delicate product organization.
Application: Fumaric acid is a kind of food-purpose acidity regulators permitted for application by the Chinese GB2760-1996. It can also be used as acidifier, antioxidant additives, preservatives and edible spices.
1.    Precautions for application
(1) This product has a strong buffering effect, being able to maintain the pH of the aqueous solution at 3.0 with essential functions in antibacterial, anti-corrosion aspects.
(2) This product has astringency, being a solid acid with one of the strongest acidity. Because of its low solubility in water, it has little applications. However, due to its low water absorption property, it helps to extend the shelf life of powder products.
(3) This product, after becoming the sodium fumarate, can have better water-soluble property and flavor.
2. The scope and amount of application
 (1) Chinese "Food Additive Use of Health Standards" (GB2760-1996) provides: for carbonated drinks, the maximum usage amount is 0.3g / kg; for juice drinks, dumpling products, the value is 0.6g / kg.
(2) The reference for the actual practice:
① used for noodles, bread and bread, and added upon knead dough, the usage amount, noodles: 3g / kg; bread: about 1g / kg.
② it can be used for jams and jellies with the maximum amount being 3g/kg. Administrate alone or in combination with tartaric acid and its salts, maintain the pH at 2.8 to 3.5.
③ it can be applied to soft drinks, cold drinks, fruit juice concentrates, canned fruit (peach, orange). It is mostly combined with other organic acids with the usage amount being 20% to 30% of that of citric acid.
④ for the preparation of wine and pickles for: 2 ~ 5 g / kg (combined with succinate).
⑤ This product, when used as the acidic substance of solid beverage gas production agents, can make the product have long-lasting bubble and be delicate.
Physical and chemical properties
Fumaric acid is naturally presented in Corydalis, mushrooms and fresh beef. Product precipitated from the water is monoclinic needle-like, prismatic or leaf-like white crystalline or crystalline powder. It is odorless with a special and strong sour, which is about 1.5 times that of the citric acid. It has a melting point 287 ° C, the boiling point of 290 ° C with subjecting to sublimation at temperature above 200 ° C. When being heated to 230 ° C, it will lose water and become maleic anhydride. Its co-boiling with water can produce DL-malic acid. It is soluble in ethanol, slightly soluble in water and ether, but insoluble in chloroform. The pH value of the 3% aqueous solution is 2.0 to 2.5 with a strong buffering performance, in order to maintain the pH of the aqueous solution at around 3.0. This product is non-toxic; rat-oral LD50: 8000mg / kg.
Chemical reaction

The molecular structure of fumaric acid contains conjugated maleic acid group with both ends of ethylene double bonds being connected with a carbonyl group. Its chemical properties are very lively. It can undergo Diels-Alder reaction; polymerization (self-polymerization and copolymerization); acylation, amidation, halogenation, hydrogenation, hydration or dehydration, alkylation, free radical reaction and nucleophilic reaction; isomerization: when being heated to 250 ~ 300 ° C, it can be converted into maleic acid; esterification reaction; acyl halogenation reaction, can only generate diacid chloride, not able to produce acyl chloride; oxidation and reduction reaction; oxidation with potassium permanganate can generate racemic tartaric acid; decomposition, decarboxylation reaction and sulfonation reaction.
This information was provided by Chemicalbook Editor (2015-09-02).

Side Effects
Fumaric acid is related to malic acid, and, like malic acid , it is involved in the production of energy (in the form of adenosine triphosphate [ATP]) from food.
Fumaric acid Side Effects: Kidney disorders have been reported in people taking fumaric acid esters, possibly due to taking large amounts too quickly.9 , 10 Most studies have reported gastrointestinal upset and skin flushing as common side effects; some have also found decreased white blood cell counts with prolonged use.
Content analysis
Accurately weigh about 1g of sample and transfer into 250ml Erlenmeyer flask; add 50 mL of methanol with slowly heating on the steam bath to dissolve the sample. After cooling, add a few drops of phenolphthalein test solution (TS-167); use 0.5mol / L sodium hydroxide for titration to until it appears light red, and last for more than 30 s. At the same time, perform a blank test, and make the necessary correction. Each mL of 0.5mol / L sodium hydroxide is equivalent to 290.02 mg of fumaric acid (C4H4O4).
Toxicity
ADI does not make special provision (FAO / WHO, 2001).
LD50: 10700 mg / kg (rat, oral).
It can be safely used in food (FDA, §172.350, 2000).
Usage limit
GB 2760-96: carbonated beverages, 0.3 g / kg; fruit juice beverages, raw noodle products, 0.6 g / kg; chewing gum 8.0 g / kg. It is also allowable edible flavor.
FAO / WHO (1984): jam and jelly, orange peel jelly: 3g / kg (amount when used alone or used in combination with tartaric acid and its salts so the pH is maintained 2.8 ~ 3.5).
FEMA (Mg / kg): soft drinks 50; baked goods 1300; puddings 3600.
Standards for Use of Food Additives
Name    Food allowed to be added as additives    Function of additive    Maximal allowable usage amount(g/kg)    Maximal allowable residue(g/kg)
Fumaric acid    Food    Edible spices    The amount of each spice ingredients used for formulation of fragrance should not exceed the maximal allowable amount of maximal allowable residue provided in GB2760.    
Fumaric acid    Carbonate drinking    Acidity regulator    0.3   
Fumaric acid    Fruit and vegetables (meat) drink    Acidity regulator    0.6   
Fumaric acid   
Raw noodle products (such as noodles, dumpling wrapper, wonton wrapper and Shumai wrapper)    Acidity regulator    0.6   
Fumaric acid    Gum candy    Acidity regulator    8.0   
Chemical properties
It appears as monoclinic colorless needle-like or lobular crystals with fruit sour. It is slightly soluble in water, ether and acetic acid, soluble in ethanol but almost insoluble in chloroform.
Uses
1. It can be used as mordant
2. It can be used for the manufacturing of unsaturated polyester resin, pesticides, sour agents and amino acids
3. It can be used as sour agent, mostly used in combination with citric acid. It can be applied to raw noodles products and fruit juice drinking with the maximum usage amount of 0.6g / kg; it can also be used for carbonated drinks with the maximum usage amount of 0.3g / kg.
4. Fumaric acid is used for the production of unsaturated polyester resin. This kind of resin is characterized by excellent resistance to chemical corrosion as well as heat resistance; the copolymer of fumaric acid and vinyl acetate is a kind of excellent adhesive. Its copolymer with styrene copolymer is the raw material for the manufacture of glass fiber. The plasticizer of the fumaric acid is non-toxic and can be applied to the vinyl acetate latex contact with food. This product is the intermediate of pharmaceutical and optical bleaching agents and other fine chemicals. Neutralization of fumaric acid with sodium carbonate can generate sodium fumarate ([17013-01-3]), and then replaced with ferrous sulfate to get iron fumarate, being the drug Fersamal used for the treatment of small red blood cell anemic. The product, as a food additive - sourness agent, used in soft drinks, fruit sugar, jelly, ice cream with most of them used in combination with sourness agent, citric acid. The monosidum salt made from the reaction between fumaric acid and sodium hydroxide can also used as sour seasoning, also used as the intermediate of synthetic resin and mordant.
5. It can be used as acidity regulator of food with strong effect of anti-bacterial and anti-corrosive. It can also be used as acidizing agent, anti-thermal oxidation additives, curing accelerators, spices. When being used as the acid substance of solid beverage gas production agent, the resultant bubble is long-lasting and delicate; it can also applied to fine chemical intermediates of medicine and optics bleaching agents. It is used for the production of antidote, sodium dimercaptosuccinate and the drug Fersamal that used for the treatment of small red blood cell anemia. In addition, it is also used for the production of unsaturated polyester resin.
6. It can be used for calibration of standard alkaline solution. It can be used for separation of thorium from cerium, lanthanum, praseodymium and rubidium. It can be applied to synthetic resin. It can also be used as mordant and antioxidant.
Production method
There are many ways to produce fumaric acid in industry. Its main source is through the oxidation of benzene (or butylene) to generate maleic acid (or maleic anhydride) in the presence of the catalyst, followed by isomerization. Send the benzene (or 80% butene) together with excess air into a fluidized bed or fixed bed reactor for oxidation reaction to generate maleic anhydride. The recycled acid was absorbed into maleic acid. Then after going through decolorization filtering, maleic acid is subject to isomerization under the action of the thiourea catalyst. The reactant undergoes filtration, washing and drying to obtain fumaric acid.
Ammonium persulfate-ammonium bromide mixtures or metal salts, amine salts, mercaptans and 10-20% hydrochloric acid can be used as the isomerization catalyst.
Carbohydrates such as sucrose, glucose, maltose, after undergoing fermentation by Rhizopus nigrocans can also used for manufacturing of fumaric acid. With the method of sugar fermentation, 1t products need to consume 8 ton of grain, which is quite uneconomical. Domestic research has taken liquid paraffin instead of food fermentation, using the liquid wax with high C16-C18 content as carbon source, after 80-88 h of fermentation, can obtain a conversion rate of liquid wax of about 50% and extraction rate of 50% or more. Furfural way: take furfural as the raw material; go through sodium chlorate oxidation to obtain it. For details: supply 58.5 g of KClO3 powder to a 250 mL flask; add an appropriate amount of V2O5 / MoO3 (0.8: 1) catalyst and 100 mL of a 0.5 mol/L hydrochloric acid solution. Under continuous stirring at 110 °C, add dropwise of 20 mL of furfural at a speed of 1 mL/min. After the completion of dropping, continue the reaction for 2h and then cool to room temperature; filter, and the filtrate is recovered. The filter cake is placed in 100mL distilled water, crushed, filtered to get the crude fumaric acid, followed by dilute hydrochloric acid recrystallization to get the finished product.
Chemical Properties
white powder or colourless crystals
Usage
Occurs in many plants. Essential to vegetable and tissue respiration. Used as an antioxidant.
Definition
ChEBI: A butenedioic acid in which the C2C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.
General Description
A colorless crystalline solid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Combustible, though may be difficult to ignite. Used to make paints and plastics, in food processing and preservation, and for other uses.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Fumaric acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Fumaric acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. Partial carbonization and formation of maleic anhydride occur at 446° F (open vessel).
Health Hazard
Inhalation of dust may cause respiratory irritation. Compound is non-toxic when ingested. Prolonged contact with eyes or skin may cause irritation.
Fumaric acid Preparation Products And Raw materials
Raw materials
Ammonium bromide Maleic acid Maleic anhydride Mineral oil D(+)-Sucrose Maltose Benzene Sodium chlorate wax liquid butene Isomerization catalyst Activated carbon Thiocarbamide
Preparation Products
FUMARONITRILE Fumaryl chloride Ferrous fumarate Benzylfumarate L-Aspartic acid D-Tartaric acid DL-Malic acid L-Alanine Disodium fumarate NEBRACETAM 1-Boc-4-(4-methoxycarbonylphenyl)piperazine Diethyl fumarate Dimethyl fumarate 4-[4-(tert-Butoxycarbonyl)piperazino]benzoic acid SEMOTIADIL BROMOSUCCINIC ACID 6-Methylcoumarin Succinic acid
Fumaric acid Suppliers      Global( 369)Suppliers     
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Tianjin Ji Ping Jia Chemical Co., Ltd. 18622448868022-58558203jpjchem@163.comCHINA 497 62
Shanghai Kangtuo Chemical Co., Ltd. 021-69185553 69185552021-69186006kangtuochem@163.comCHINA 5177 55
Shanghai Boyle Chemical Co., Ltd. Mr Qiu:021-50182298(Demestic market) Miss Xu:021-50180596(Abroad market)+86-21-57758967sales@boylechem.comCHINA 2221 55
J & K SCIENTIFIC LTD. 400-666-7788 +86-10-82848833+86-10-82849933jkinfo@jkchemical.com;market6@jkchemical.comCHINA 96839 76
Meryer (Shanghai) Chemical Technology Co., Ltd. +86-(0)21-61259100(Shanghai) +86-(0)755-86170099(ShenZhen) +86-(0)10-59487313(Beijing)+86-(0)21-61259102(Shanghai) +86-(0)755-86170066(ShenZhen) +86-(0)10-88580358(Beijing)sh@meryer.comCHINA 40406 62
Alfa Aesar 400-610-6006; 021-67582000021-67582001/03/05saleschina@alfa-asia.comCHINA 30330 84
TAIYUAN RHF CO.,LTD. +86 351 7031519+86 351 7031519sales@RHFChem.comCHINA 2366 56
TCI (Shanghai) Development Co., Ltd. 800-988-0390021-67121385sales@tcishanghai.com.cnCHINA 22834 81
Beijing dtftchem Technology Co., Ltd. 13651141086; 86(10)60275028、6027582086 (10) 60270825dtftchem@sina.comCHINA 1450 62
BeiJing Hwrk Chemicals Limted 4006990298;010-57411839;0757-86311057;021-51691807010-87653215;0757-86311057;021-55236763sales@hwrkchemical.comCHINA 12647 55
 
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