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TRANS-BUTENEDIOIC ACID

Fumaric acid

CAS: 110-17-8

Molecular Formula: C4H4O4

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TRANS-BUTENEDIOIC ACID - Names and Identifiers

Name Fumaric acid
Synonyms Fumaric acid
ACIDUM FUMARICUM
RARECHEM AL BO 0142
TRANS-BUTENEDIOIC ACID
TRANS-2-BUTENEDIOIC ACID
trans-2-Butenedioic acid
TRANS-2-BUTEN-1,4-DIOIC ACID
TRANS-BUTENEDICARBOXYLIC ACID
TRANS-1,2-ETHYLENEDICARBOXYLIC ACID
TRANS-1,2-ETHYLENTRICARBOXYLIC ACID
CAS 110-17-8
EINECS 203-743-0
InChI InChI=1/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
InChIKey VZCYOOQTPOCHFL-OWOJBTEDSA-N

TRANS-BUTENEDIOIC ACID - Physico-chemical Properties

Molecular FormulaC4H4O4
Molar Mass116.07
Density1.62
Melting Point298-300 °C (subl.) (lit.)
Boling Point137.07°C (rough estimate)
Flash Point230 °C
JECFA Number618
Water Solubility0.63 g/100 mL (25 ºC)
Solubility Soluble in DMSO, water, insoluble in fat-soluble organic solvents
Vapor Presure1.7 mm Hg ( 165 °C)
AppearanceWhite powder or colorless crystal
ColorWhite
Merck14,4287
BRN605763
pKa3.02, 4.38(at 25℃)
PH3.19(1 mM solution);2.57(10 mM solution);2.03(100 mM solution);
Storage ConditionStore below +30°C.
StabilityStable at room temperature. Decomposes at around 230 C. Incompatible with strong oxidizing agents, bases, reducing agents. Combustible.
SensitiveEasily absorbing moisture
Explosive Limit40%
Refractive Index1.5260 (estimate)
MDLMFCD00002700
Physical and Chemical PropertiesCharacteristics of monoclinic colorless needle-like or lobular Crystal, fruit sour taste.
solubility: slightly soluble in water, ether and acetic acid, soluble in ethanol. Almost insoluble in chloroform.
UseFor the manufacture of Unsaturated Polyester Resin, pesticides, acid and amino acids

TRANS-BUTENEDIOIC ACID - Risk and Safety

Hazard SymbolsXi - Irritant
Irritant
Risk Codes36 - Irritating to the eyes
Safety Description26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
UN IDsUN 9126
WGK Germany1
RTECSLS9625000
TSCAYes
HS Code29171900
ToxicityLD50 orally in Rabbit: 9300 mg/kg LD50 dermal Rabbit 20000 mg/kg

TRANS-BUTENEDIOIC ACID - Upstream Downstream Industry

Raw MaterialsBenzene
Charcoal
Thiourea
Maleic acid
Maleic anhydride
Downstream ProductsL(+)-Aspartic acid
Dimethyl fumarate

TRANS-BUTENEDIOIC ACID - Reference

Reference
Show more
1. TUKHVATSHIN MARAT, Zhang Qian, Qu Yanqin, Zheng Deyong, Yang Jiangfan, Ye Naixing. Analysis of Organic Acid Components in White Tea Processing [J]. Fujian Tea, 2019,41(03):11-12.
2. Dailin, Xu Yuanyuan, Xiong Bo, et al. Accumulation Characteristics of Ascorbic Acid, Glutathione and Organic Acid in Huangguoan Fruit [J]. Journal of Zhejiang Agriculture, 2018, v.30;No.189(08):75-82.
3. Li Biao, Li Chengjie, Chen Shuangyang, etc. Optimization of Cooking Process of Lentinus edodes Soup and Study on Non-volatile Flavor Compounds [J]. Journal of Food Science and Technology, 36(1).
4. Wang Siwei, Liu Yanping, Wang Xiaonan, et al. Determination of 10 Organic Acids in Fresh Litchi Pulp Based on High Performance Liquid Chromatography-Triple Quadrupole Tandem Mass Spectrometry [J]. Journal of Pesticide Science, 2019(3).
5. Ma Ning, Wang Chaofan, Fang Dong Road, et al. Flavor Changes of Flammulina velutipes Packed with Polyethylene Film during Cold Storage [J]. China Agricultural Sciences, 2019, 52(08):146-159.
6. Zhang Yapeng, Zhu Hongxia, Liu Xin, Fan Tianyi, Liu Huan, Wang Fang, Deng Li. Mechanism and Kinetic Analysis of Fumaric Acid Adsorption by D201 Resin [J]. Ion Exchange and Adsorption, 2020,36(04):346-356.
7. Duan Yunfei, Wu Guangbin, Ye Hong, Chen Zhaohua, Zhang Shen, Chen Fahe. Simultaneous Determination of Seven Organic Acids in Postharvest Lotus Fruit by HPLC [J]. Food Science, 2021,42(04):175-180.
8. [IF = 4.411] Cuihua Chen et al."Quality Evaluation of Apocyni Veneti Folium from Different Habitats and Commercial Herbs Based on Simultaneous Determination of Multiple Bioactive Constituents Combined with Multivariate Statistical Analysis." Molecules 2018 Mar;23(3):5
9. [IF = 3.757] Yuchen Wang et al."Metabolic profile of ginkgo kernel juice fermented with lactic aicd bacteria: A potential way to degrade ginkgolic acids and enrich terpene lactones and phenolics." Process Biochem. 2019 Jan;76:25
10. [IF = 7.312] Jiabao Gu et al."Fabrication of magnetic dual Z-scheme heterojunction materials for efficient photocatalytic performance: The study of ternary novel MIL-88A(Fe)/BiOBr/SrFe12O19 nanocomposite." Sep Purif Technol. 2022 May;289:120778
11. [IF = 9.423] Yi Li et al."Blockage of citrate export prevents TCA cycle fragmentation via Irg1 inactivation." Cell Rep. 2022 Feb;38:110391
12. [IF = 6.576] Rui Wang et al."Quality Characteristics and Inhibitory Xanthine Oxidase Potential of 21 Sour Cherry (Prunus Cerasus L.) Varieties Cultivated in China." Front Nutr.2021; 8: 796294

TRANS-BUTENEDIOIC ACID - Nature

Open Data Verified Data

monoclinic crystals are colorless, needle-like or lobular crystals with a sour taste of fruit. Melting point 287 ℃,290 ℃ sublimation, relative density of 1. 635. Slightly soluble in water, ether and acetic acid, soluble in ethanol. Almost insoluble in chloroform.

Last Update：2024-01-02 23:10:35

TRANS-BUTENEDIOIC ACID - Preparation Method

Open Data Verified Data
  1. cis-acid isomerization method cis-acid is heated to 145-260 ° C. Under the action of thiourea catalyst and isomerized to form anti-acid. The product is then filtered, washed and dried.
  2. the fermentation method uses liquid paraffin as the raw material and Candida as the strain for deep fermentation, and then obtains the fumaric acid product through multi-step processes such as separation, decolorization, crystallization and drying. Fumaric acid can also be obtained from the fermentation of sweet potato and starch.
  3. furfural method using furfural as raw material, obtained by sodium chlorate oxidation.
Last Update：2022-01-01 10:32:03

TRANS-BUTENEDIOIC ACID - Standard

Authoritative Data Verified Data

This product is fumaric acid. The content of C4h404 shall not be less than 99.0% calculated as anhydrous.

Last Update：2024-01-02 23:10:35

TRANS-BUTENEDIOIC ACID - Trait

Authoritative Data Verified Data
  • This product is white or off-white particles or crystalline powder, odorless.
  • This product is dissolved in ethanol, slightly soluble in water or ether, and almost insoluble in dichloromethane.
Last Update：2022-01-01 11:27:14

TRANS-BUTENEDIOIC ACID - Use

Open Data Verified Data

It is mainly used as a raw material for unsaturated resins and alkyd resins. The adhesive can be produced by polymerization with vinyl acetate. It can also be used as a raw material for medicine. Used in the food and beverage industry as a sour agent.

Last Update：2022-01-01 10:32:03

TRANS-BUTENEDIOIC ACID - Differential diagnosis

Authoritative Data Verified Data
  1. take about 0.5g of this product, Add 10ml of water, heat and boil, drop the bromine test solution, and the color of the bromine test solution will disappear.
  2. appropriate amounts of the present product and the fumaric acid reference product were taken, respectively dissolved and diluted with the mobile phase under the item of related substances to prepare a solution containing about lOug per 1 ml as a test solution and a reference solution. According to the chromatographic conditions under the item of related substances, 10ul of the test solution and the reference solution are taken and injected into the human liquid chromatograph respectively, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the control solution.
  3. The infrared absorption spectrum of this product should be consistent with that of fumaric acid reference substance (General rule 0402).
Last Update：2022-01-01 11:27:15

TRANS-BUTENEDIOIC ACID - Safety

Open Data Verified Data
  • This product is non-toxic. Rabbit oral LD505000mg/kg, mouse intraperitoneal injection of LD50200mg/kg.
  • with woven bag lined with plastic bag, each net weight of 25kg, can also be packed with cardboard barrel lined with plastic bag, net weight of 30kg or 50kg per barrel. Store in a cool and dry place.
Last Update：2022-01-01 10:32:04

TRANS-BUTENEDIOIC ACID - Exam

Authoritative Data Verified Data

maleic acid and related substances

take an appropriate amount of this product, accurately weigh it, add mobile phase to dissolve and quantitatively dilute to prepare a solution containing about 1 mg per 1 ml, as a test solution; Take an appropriate amount of fumaric acid and maleic acid, precision weighing, adding mobile phase dissolution and quantitative dilution to prepare 1ug of mixed solution per 1 ml, as a reference solution. Test according to high performance liquid chromatography (General 0512). Silica gel bonded with eighteen alkyl silane was used as the filler, and water (adjusted to pH 3.0 with phosphoric acid)-acetonitrile (85:15) was used as the mobile phase, and the detection wavelength was 210nm. Take 10ul of reference solution and inject human Liquid Chromatograph. The resolution of fumaric acid peak and maleic acid peak should be greater than 2. 5. The sample solution and the reference solution are respectively injected into the liquid chromatograph, and the chromatogram is recorded to 3 times of the retention time of the fumaric acid peak. Calculated by peak area according to external standard method, the content of maleic acid shall not exceed 0.1%, other single impurities shall not exceed 0.1% by Peak area of fumaric acid peak in reference solution, and the total amount of impurities shall not exceed 0.2%.

moisture

take this product, according to the moisture determination method (General 0832 first method 1), the water content shall not exceed 0.5%.

ignition residue

take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.

Heavy metals

The residue left under the item of ignition residue shall be inspected according to law (General rule 0821 second law), and the content of heavy metal shall not exceed 10 parts per million.

Last Update：2022-01-01 11:27:15

TRANS-BUTENEDIOIC ACID - Content determination

Authoritative Data Verified Data

take this product about l. Add 50ml of methanol, slowly heat in a hot water bath to dissolve, add several drops of phenolphthalein indicator solution, and titrate with sodium hydroxide titration solution (0.5mol/L), every 1 ml of sodium hydroxide titration solution (0. 5mol/L) equivalent to 29.02mg C4H40 4.

Last Update：2022-01-01 11:27:16

TRANS-BUTENEDIOIC ACID - Category

Authoritative Data Verified Data

pharmaceutical excipients, pH regulators and effervescent agents.

Last Update：2022-01-01 11:27:16

TRANS-BUTENEDIOIC ACID - Storage

Authoritative Data Verified Data

sealed storage.

Last Update：2022-01-01 11:27:16

TRANS-BUTENEDIOIC ACID - Reference Information

FEMA2488 | FUMARIC ACID
LogP-4.02 at 20℃
NIST chemical information Information provided by: webbook.nist.gov (external link)
EPA chemical information Information provided by: ofmpub.epa.gov (external link)
acidity regulator fumaric acid is an important organic chemical raw material, an intermediate of fine chemical products, and an important derivative of maleic anhydride. it is widely used in the fields of food, coatings, resins and plasticizers. In the food industry, fumaric acid is used as a sour agent, which can be used in refreshing beverages, western-style wine, cold drinks, concentrated fruit juice, canned fruits, pickles, and ice cream. Acidic substances used as gas-producing agents for solid beverages have good bubble durability and fine product organization.
use: fumaric acid is a food acidity regulator, acidifier, antioxidant additive, pickling accelerator and edible spice allowed by GB2760-1996 regulations in China. 1. matters needing attention in use
(1) this product has strong buffering effect to keep the aqueous solution at about pH 3.0, and plays an important role in antibacterial and antiseptic.
(2) This product has astringent taste and is one of the most fortified solid acids in sour taste. Because of its low solubility in water, it is less used. However, its low water absorption rate helps to extend the shelf life of powder products.
(3) After this product becomes sodium fumarate, it has better water solubility and flavor. 2. scope of use and usage
(1) China's "hygienic standard for the use of food additives" (GB2760-1996) stipulates that the maximum usage for carbonated beverages is 0.3 g/kg; Juice drinks and raw flour wet products are 0.6 g/kg.
(2) reference for practical use:
① used for noodles, bread and steamed bread, add them when making noodles, and the dosage is 3 g/kg for noodles; Bread and steamed bread are about 1 g/kg.
② for jam and jelly, the maximum dosage is 3 g/kg. Alone or in combination with tartaric acid and its salts to keep the pH 2.8~3.5.
③ It is used for refreshing drinks, cold drinks, concentrated fruit juice, canned fruits (peach, orange), etc., and is mostly used in combination with other organic acids. When combined with citric acid, its dosage is 20% ~ 30% of citric acid.
④ 2~5 g/kg (combined with succinic acid) for wine preparation and pickled vegetables.
⑤ when this product is used as acidic substance of solid beverage gas generating agent, the product bubbles are durable and delicate.
fig. 1 is a physical picture of food additive fumaric acid.
Chemical reaction The molecular structure of fumaric acid contains a conjugated maleoyl group, and the two ends of the ethylene double bond are connected to a carbonyl group, and the chemical properties are very active. Diels-Alder reactions can be carried out; polymerization reactions (self-polymerization and copolymerization); addition reactions such as acylation, amidation, halogenation, hydrogenation, hydration or dehydration, alkylation, free radical reactions, nucleophilic reactions; isomerization reaction, Heat to 250~300 ℃ to convert to maleic acid; esterification reaction; acylation reaction, only diacyl chloride can be generated, not monobilyl chloride; oxidation and reduction reaction, oxidation with potassium permanganate to generate exosartaric acid; decomposition and decarboxylation reactions and sulfonation reactions.
content analysis accurately weigh about 1g of the sample, move it into a 250ml conical flask, add methanol, 50ml, and slowly heat the sample in a steam bath to dissolve the sample. After cooling, add several drops of phenolphthalein test solution (TS-167) and titrate with 0.5mol/L sodium hydroxide until it appears light red for more than 30s. At the same time, blank test is carried out and necessary correction is made. 0.5mol/L sodium hydroxide is equivalent to 29.02mg of fumaric acid (C4H4O4) per mL.
toxicity ADI does not make special regulations (FAO/WHO,2001). LD50 10700mg/kg (rat, oral). Can be safely used in food (FDA, 172.350,2000).
usage limit GB 2760-96: carbonated beverage, 0.3 g/kg; Juice beverage, raw wet flour products, 0.6 g/kg; Chewing gum 8.0 g/kg. It is also a permitted edible spice. FAO/WHO(1984): jam, jelly and orange peel jelly 3 g/kg (only or combined with tartaric acid and its salts to keep Ph 2.8~3.5). FEMA.(mg/kg): soft drink 50; Baked food 1300; Pudding 3600.
use used as mordant
used to make unsaturated polyester resin, pesticide, sour agent and amino acid, etc.
used as sour agent, mostly combined with citric acid. It can be used for raw flour wet products and fruit juice drinks with a maximum usage of 0.6 g/kg; It can also be used for carbonated drinks with a maximum usage of 0.3 g/kg.
Fumaric acid is used to produce unsaturated polyester resin. This type of resin is characterized by good chemical corrosion resistance and heat resistance; the copolymer of Fumaric acid and ethylene acetate is a good adhesive The copolymer with styrene is the raw material for making glass fiber reinforced plastic. The plasticizer made from Fumaric acid is non-toxic and can be used for vinyl acetate latex in contact with food. This product is an intermediate of fine chemicals such as medicine and optical bleaching agents. It is used in the production of antidote dimercaptosuccinic acid in the pharmaceutical industry. Fumaric acid is neutralized with sodium carbonate to obtain sodium butenene ([17013-01-3]), and then replaced with ferrous sulfate to obtain ferric fumarate, which is a drug for the treatment of small red blood cell anemia. As a food additive-sour agent, this product is used for refreshing beverages, fruit candy, jelly, ice cream, etc. It is mostly used with sour agent citric acid, and the monosodium salt made by the reaction of fumaric acid and sodium hydroxide is also used as sour condiment, and also used as an intermediate of synthetic resin and mordant.
food sour agent, antibacterial, anti-corrosion important role; acidity regulator, acidifier, anti-thermal oxidation additives, pickling accelerator, spices. When used as a solid beverage gas-producing agent, the bubbles are durable and delicate; fine chemical intermediates such as medicine and optical bleach. For the production of antidote dimercaptosuccinate sodium and blood-rich iron for the treatment of small red blood cell anemia. It is also used to produce unsaturated polyester resin.
Standard lye for calibration. Thorium is separated from cerium, lanthanum, praseodymium and rubidium. Synthetic resin. Mordant. Antioxidant.
Production method There are many methods in the industry to produce fumaric acid. Its main source is the oxidation of benzene (or butene) to maleic acid (or maleic anhydride) in the presence of a catalyst, which is obtained by isomerization. Benzene (or 80% butene) is oxidized with excess air in a fluidized bed or fixed bed reactor to produce maleic anhydride, which is absorbed into maleic acid by the circulating acid liquid. After decolorization and filtration, maleic acid is isomerized under the action of thiourea catalyst, and the reactants are filtered, washed, and dried to obtain fumaric acid. The isomerization catalyst also uses ammonium persulfate-ammonium bromide mixture or metal salt, amine salt, mercaptan and 10-20% hydrochloric acid. Carbohydrates such as sucrose, glucose, and maltose can also be fermented by Blackroot bacteria to produce fumaric acid. With the method of sugar fermentation, 1t product consumes 8t of grain, which is economically uneconomical. Domestic research uses liquid paraffin instead of grain fermentation, and uses liquid wax with high C16-C18 content as carbon source. After 80-88h fermentation, the liquid wax conversion rate is about 50% and the extraction rate is above 50%. The furfural method uses furfural as raw material and is obtained by oxidation of sodium chlorate.
Benzene (or 80% butene) and excess air are absorbed by circulating acid in a fluidized bed or fixed bed reactor to generate maleic acid; then after decolorization and filtration, maleic acid is catalyzed by thiourea It is converted into fumaric acid, and the reactants are filtered, washed and dried to obtain the finished product. Products can also be made by furfural liquid phase oxidation. 58.5gKClO3 powder, appropriate amount of V2O5/MoO3(0.8:1) catalyst and 100mL 0.5mol/L hydrochloric acid solution were added into a 250mL flask. furfural was added dropwise at a speed of 1 mL/min under constant stirring and 110 ℃, and the reaction was continued for 2 hours after adding. Then cool to room temperature, filter, and recover the filtrate. The filter cake is crushed in 100mL distilled water, filtered to obtain crude fumaric acid, and recrystallized by dilute hydrochloric acid to obtain the finished product.
spontaneous combustion temperature 375°C
toxic substance data information provided by: pubchem.ncbi.nlm.nih.gov (external link)
Last Update：2024-04-09 02:00:06
TRANS-BUTENEDIOIC ACID
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View History
TRANS-BUTENEDIOIC ACID
METHYL 2-([(4-METHYLPHENYL)SULFONYL]AMINO)-2-PHENYLACETATE
CHROMIUM(III) NITRATE NONAHYDRATE FOR AN
Raw Materials for TRANS-BUTENEDIOIC ACID
Benzene
Charcoal
Thiourea
Maleic acid
Maleic anhydride
Downstream Products for TRANS-BUTENEDIOIC ACID
L(+)-Aspartic acid
Dimethyl fumarate
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