Dimethyl fumarate
Dimethyl fumarate
CAS: 624-49-7
Molecular Formula: C6H8O4
Dimethyl fumarate - Names and Identifiers
| Name | Dimethyl fumarate |
| Synonyms | 624-49-7 Dimethylfumarate Dimethyl fumarate DIMETHYL FUMARATE dimethyl (2E)-but-2-enedioate 2-Butenedioic acid (E)-, dimethyl ester |
| CAS | 624-49-7 |
| EINECS | 210-849-0 |
| InChI | InChI=1/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+ |
Dimethyl fumarate - Physico-chemical Properties
| Molecular Formula | C6H8O4 |
| Density | 1.124g/cm3 |
| Melting Point | 102-105℃ |
| Boling Point | 193°C at 760 mmHg |
| Flash Point | 91.1°C |
| Solubility | Soluble in ethyl acetate, chloroform, acetone and alcohols, slightly soluble in ether, slightly soluble in water. |
| Vapor Presure | 0.475mmHg at 25°C |
| Appearance | White crystal or crystalline powder |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.435 |
| MDL | MFCD00064438 |
| Physical and Chemical Properties | Melting point 102-105°C boiling point 192-193°C |
| Use | Widely used in food, food, feed, tobacco, leather and clothing and other anti-mildew and fresh |
Dimethyl fumarate - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R21 - Harmful in contact with skin R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
Dimethyl fumarate - Upstream Downstream Industry
Dimethyl fumarate - Introduction
It has an ester fragrance. Easy to sublimate, slightly soluble in water, soluble in ethanol. It is stable to light and heat, basically unchanged for 72 hours under ultraviolet and sunlight, and does not decompose after heating at 110 ℃ for 2 hours. Mechanism of action: it can smoothly penetrate the cell membrane of microorganisms, inhibit the division of microbial cells, and inhibit the respiration of microorganisms by inhibiting the enzyme activity of the tricarboxylic acid cycle (TCAC) phosphate hexose pathway (HMP) and glycolysis pathway (EMP), so as to achieve antibacterial effect and effectively control the growth and reproduction of microorganisms.
Last Update：2022-10-16 17:27:21
Dimethyl fumarate - Functional profile
1. Character: white scaly
Dimethyl maleate
Dimethyl maleate
Crystal, slightly spicy taste, soluble in alcohol, ether, chloroform and other solvents, slightly soluble in water.
Second, the mechanism of action: the antibacterial activity of dimethyl fumarate is the molecular state of dimethyl fumarate, in the molecular state of dimethyl fumarate can successfully penetrate the cell membrane of microorganisms, enter the cell, so as to play its antibacterial effect, dimethyl fumarate effectively enters the microbial body through both contact and fumigation pathways, inhibiting microbial cell division, and through the tricarboxylic acid cycle (TCAC) through the hexosyl phosphate pathway (HMP) inhibition of the enzyme activity of the glycolysis pathway (EMP) to inhibit microbial respiration, so that the growth and reproduction of microorganisms are effectively controlled.
Three, antibacterial spectrum and effect: Many mold has a special inhibitory effect, and has the ability to resist fungi.
Characteristics: it is a new type of fungicide developed in the United States in the Eighties. It is named "mildew enemy" and has low toxicity (2240mg/kg for oral administration of LD rats), good chemical stability, long action time, wide pH range and other characteristics, can inhibit a variety of mold, yeast and bacteria, especially for Clostridium botulinum and Aspergillus flavus has a good inhibitory effect.
Five, use: the antibacterial activity of dimethyl fumarate is not affected by the pH value; And has insecticidal activity, also has the effect of killing and fumigation, widely used in food, beverage, feed, Chinese herbal medicine, cosmetics, fish, meat, vegetables, fruits and other mildew-proof, antiseptic, insect-proof, fresh-keeping
Last Update：2024-04-10 22:29:15
Dimethyl fumarate - Test
On January 29, 2009, the EU member states adopted a draft resolution "to ensure that consumer products containing dimethyl fumarate are not placed on the European market", which entered into force on May 1, 2009. The draft specifies that if the content of dimethyl fumarate in the consumer product or its components exceeds 0.1 mg/kg, or the product itself has declared its content of dimethyl fumarate, will be recognized as "dimethyl fumarate containing" products, which will be banned from entering the EU market circulation and sale.
dimethyl fumarate (DMF) is commonly used as an antiseptic and antifungal product, and is commonly used in the production, storage and transportation of leather, footwear and textiles. However, since last October, the EU has reported cases of skin allergy, acute eczema and burns caused by consumer exposure to shoes and leather couches containing dimethyl fumarate, it has received extensive attention. The EU has also carried out research and analysis, and eventually issued the above draft and limit standards. Before the adoption of the EU draft, France and Belgium had taken specific measures to ban the import and sale of shoes and seats containing dimethyl fumarate. Spain has also introduced regulations that prohibit any products that come into contact with the skin and contain dimethyl fumarate. Moreover, since the end of last year, many batches of Chinese products have been detained by France and other countries because of the excessive content of dimethyl fumarate.
dimethyl fumarate is widely used in domestic products. A lot of shoes, leather furniture and home textiles and other products will be put into the moisture-proof bag containing this ingredient in the package for moisture and mildew prevention. In Zhejiang province, the leather products of Wenzhou, Haining and other places are traditional foreign trade export products, only in Wenzhou, the export of footwear products reached 0.276 billion US dollars in 2008. Textiles are Zhejiang's export advantage products, about 40 billion of the annual export volume. These exports account for a considerable share of the EU market. More worrying is that, according to the data, because dimethyl fumarate has low toxicity, strong antibacterial ability, many kinds of antibacterial, not affected by the environment and other characteristics, is also widely used in food, food, feed, cosmetics, tobacco and other anti-mildew and fresh, therefore, the EU to all containing dimethyl fumarate consumer goods ban, is bound to bring great adverse effects to the relevant industries in our province.
In the face of the huge challenge of the ban, the inspection Quarantine Department reminded the relevant export enterprises to make timely adjustments and switch to more environmentally friendly and healthy moisture-proof and mildew-proof products to meet the requirements of the draft, and actively communicate with foreign customers to reduce the impact of the draft on the export of products. In the near future, the inspection Quarantine department will also strengthen the inspection and supervision of relevant enterprises within the jurisdiction, to avoid unqualified products to the EU, resulting in greater economic and reputation losses.
Last Update：2024-04-10 22:29:15
Dimethyl fumarate - Synthetic Methods
1, sulfuric acid catalyzed synthesis of DMF
drying agent without dimethyl fumarate
sulfuric acid as a catalyst is a classical synthesis method, the product yield can reach 92% [4,8,9], although this method is simple and high yield, but, due to the corrosion of sulfuric acid, will cause side reactions, and there are three waste pollution and other shortcomings.
2. Synthesis of DMF catalyzed by p-toluenesulfonic acid
The yield of DMF synthesized with toluene sulfonic acid as catalyst was about 67%. P-toluenesulfonic acid is a kind of organic acid, although it is less corrosive to equipment and three wastes, it is not easy to cause side reactions, the product is good in color, cheap and easy to obtain, easy to store and transport and use, the dosage is small, the activity is high, but the yield is relatively low disadvantage.
3. Resin-catalyzed synthesis of DMF
strong acid cation exchange resin as early as the 50's of the 20th century began to be used in some esterification reaction, the resulting ester color is low, the post-treatment is convenient, can be reused, non-corrosive to equipment, does not produce three wastes, extremely industrial use value. The yield of DMF was 91.4% using strong acid ion exchange resin as catalyst.
4. Synthesis of DMF catalyzed by solid superacid
The synthesis of dimethyl fumarate catalyzed by solid superacid superacid is stronger than that of 100% sulfuric acid. Solid superacid has the advantages of non-corrosive equipment, no environmental pollution, no fear of water, high temperature resistance, high reactivity, good selectivity, easy manufacture, easy separation in the reaction system, not easy to poisoning, etc, at the same time can be reused, so it has a certain industrial application value.
5, ferric chloride catalyzed synthesis of DMF
dimethyl fumarate testing services available with the pairwise test
synthesis of dimethyl fumarate catalyzed by crystalline ferric chloride crystalline ferric chloride (FeCI3 · 6H2O) is a cheap and easily available compound, using it to catalyze the synthesis of dimethyl fumarate, corrosion is small, three waste pollution is light, easy to operate, has a certain application value, the favorable application conditions are: when the catalyst 0.8g, fumaric acid 58g, methanol 20ml, that is, the molar ratio of 0.06: 1: 10, reflux 4H, A white crystalline product was obtained with a yield of 61.7% [13] 〕.
6. Synthesis of DMF catalyzed by Heteropoly acid
Heteropoly acid is a polybasic acid formed by the condensation of two or more inorganic oxygen-containing acids, moreover, its acidity and hydroreducibility can be systematically adjusted over a wide range by changing the constituent elements. It has high catalytic activity and selectivity for many reactions, and non volatile, thermal stability, less pollution, can greatly reduce the corrosion of equipment, can be regenerated and reused.
7, rare earth compounds catalyzed synthesis of DMF
rare earth compounds are easily available and rich in resources in our country. The development and utilization of rare earth compounds is of great economic value. Li Xiaoli, etc., using three neodymium oxide (Nd2O3) catalytic synthesis of dimethyl fumarate, when 15g fumaric acid, 30ml methanol, three neodymium oxide dosage of 3%, reflux 4H, the product yield of 90% [15] 〕.
8, BF3 ·(C2H5)2O catalyzed synthesis of DMF
boron trifluoride (BF3) is a strong electron acceptor, a strong Lewis acid, which can form a complex with the carboxyl group in the electron donating carboxylic acid, so that the carbon in the carboxyl group has more positive charge, however, since BF3 is a gas, it is often used to catalyze the progress of an esterification reaction by forming a ceratine salt with an alcohol, an aldehyde, or the like.
9, fumarate esterification method. DMF was directly synthesized from fumaric acid and methanol in the presence of catalyst. The catalysts include boron trifluoride, ferric chloride hexahydrate (FeCl3 · 6H2O), sulfuric acid or phosphoric acid, and the yield is as high as 92%. Cationic resin catalyst can also be used, using Catalytic distillation technology, esterification reaction at 80-85 deg C for 5H.
10, isomeric esterification of maleic acid. Maleic acid and methanol in the catalyst, isomerization, esterification to get DMF, Catalyst HCl-H2SO4 and phosphotungstic acid. When HCl-H2SO4 is used as the catalyst, the reaction is actually carried out in two steps, that is, HCl catalyzed isomerization reaction and H2SO4 catalyzed esterification reaction. Maleic acid was refluxed with concentrated hydrochloric acid and water for 30min to obtain 91% fumaric acid; Fumaric acid was refluxed with methanol and concentrated sulfuric acid for 12h to obtain 91.9% product. Phosphotungstic acid is a composite catalyst that catalyzes both isomerization and esterification. Maleic acid and methanol were refluxed for 4H in the presence of Phosphotungstic acid to obtain 89.4% of the product. (3) the oxidation and esterification of sugar aldehyde. Using furfural as raw material, the synthesis was carried out in two steps. Firstly, the furfural is oxidized to fumaric acid with KClO3 under the catalysis of V2O5, the reaction temperature is 95 ℃-105 ℃, the reaction time is 7h, the yield is 81.5%; Then fumaric acid is heated and refluxed with methanol in the presence of concentrated sulfuric acid, DMF was obtained with a reaction time of 10H. The yield was 86.0%. (4) hydrolysis and isomerization of maleic anhydride. Using maleic anhydride as raw material, and methanol under the action of catalyst to produce DMF. The catalysts were concentrated hydrochloric acid, hydrochloric acid-phosphoric acid, ferric chloride hexahydrate, P-toluenesulfonic acid and thiourea. Hydrochloric acid-Phosphoric acid is a composite catalyst, the first hydrolysis, esterification reaction, get dimethyl maleate, the latter in bromine and light in the next isomerization to get the product; Using thiourea as catalyst, maleic anhydride is first hydrolyzed and isomerized to give fumaric acid, which is esterified in the presence of sulfuric acid to give the product.
example: a 9.8 mL flask was charged with 0.1g (8.1 mol) of maleic anhydride, 0.2 mL (1.5 mol) of methanol, and mL of concentration calculation, and the mixture was heated under reflux for h. Then 12ml (0.3mol) excess methanol was added dropwise, and after dropping for 0.5H, reflux was continued for 2H. After completion of the reaction, methanol was distilled off, after being slightly cooled, 30ml of ethanol was added, and the solid was dissolved by heating. After cooling, crystals were precipitated. The two products were recrystallized once with ethanol and water respectively to obtain 12.3g of product, with a yield of 86.2% and a melting point of 103-104 ℃.
Last Update：2024-04-10 22:29:15
Dimethyl fumarate - Health hazards
The Ministry of Health and other departments announced that the second batch of non-edible substances that may be illegally added in food have dimethyl fumarate. Its main harm is: it is scientifically proved that "mycophenolate" is easy to hydrolyze to methanol, corrosive damage to human intestinal tract and internal organs, and allergic damage to skin, which is extremely harmful. In addition, long-term consumption will have great side effects on the liver and kidney, especially for the growth and development of children will cause great harm.
DMF uses and hazards: DMF has a wide range of microorganisms, efficient antibacterial, bactericidal effect, has been widely used in food, feed, tobacco, leather and clothing and other anti-mildew and preservation. DMF can cause health damage. According to clinical trials, DMF can be inhaled through the esophagus to produce corrosive damage to the human intestinal tract and internal organs; And when the substance comes into contact with the skin, it will cause contact dermatitis pain, including itching, irritation, redness and Burns; Great harm to human health. Therefore, the presence of DMF is a serious threat.
worst hit areas: cakes, moon cakes and spicy food. Commonly known as "mycophenolate", the main role of anti-corrosion, insect. It is actually an industrial disinfectant, in the national standards can only be used for building materials, plastic products and bamboo and other industrial products, never allowed to use in food. However, due to the good anti-mildew effect, some illegal manufacturers will add it to the food, not only can make the food not easy to mildew, long shelf life, and bright color. But it is harmful to the human body, will damage the intestines, internal organs and cause allergies, especially for children's growth and development will cause great harm.
Last Update：2024-04-10 22:29:15
Dimethyl fumarate - Precautions
storage and transportation
storage
Protect from light, heat, waterproof, moisture
instruction requirements
& rarr; After May, 2009, products containing dimethyl fumarate are prohibited from being put on the market or marketed, products containing dimethyl fumarate that have been put on the market or are on the market should be withdrawn;
& rarr; The content of dimethyl fumarate in the product or product part should not exceed 0.1 mg/kg(0.1ppm);
Drying agent and anti-mildew agent sachets containing dimethyl fumarate shall not be used in & rarr; Products and packaging.
On 15, restrictions on the manufacture, placement on the market and use of articles) item 61 of the list of substances, the decree is implemented 20 days after the date of publication of the official journal of the European Union and requires member states to translate it into their national law. This portends that the previous EU Directive 2012/EU extending the effective date of dimethyl fumarate will become obsolete at the same time as the effective date of (EU)No 412, I .e, EU-wide restriction of dimethyl fumarate. Dimethyl fumarate (DMF) should not exceed 0.1mg/kg[4] in products or product parts in the EU market.
production and sales
Foreign countries producing dimethyl fumarate are the United States, Japan, Germany and so on. The output in USA is 4000t/Y, Japan is 8000t/Y,
China did not develop dimethyl fumarate in the 80 s, and in 1990, a 200t/Y production line was built in Tianshui, Gansu province. After that, Jiangsu, Jiangxi, Shandong and Shaanxi provinces all had equipment, but the scale was not large, china's total output is about 800-1000t/Y.
China has tens of thousands of food, beverage, feed production plants, more than one hundred thousand soy sauce plants and a large area of fruits and vegetables production base, the country's annual demand for mold preservative in more than 40,000 tons. As a new generation of fungicide, dimethyl fumarate has a wide range of applications, a large market capacity and a very bright future.
health hazard
suspension of use of footwear articles containing dimethyl fumarate
DMF uses and hazards: DMF has a wide range of microorganisms, efficient antibacterial, bactericidal effect, has been widely used in food, feed, tobacco, leather and clothing and other anti-mildew and preservation. DMF can cause health damage. According to clinical trials, DMF can be inhaled through the esophagus to produce corrosive damage to the human intestinal tract and internal organs; And when the substance comes into contact with the skin, it will cause contact dermatitis pain, including itching, irritation, redness and Burns; Great harm to human health. Therefore, the presence of DMF is a serious threat.
Worst hit areas: cakes, moon cakes and spicy foods. Commonly known as "mycophenolate", the main role of anti-corrosion, insect. It is actually an industrial disinfectant, in the national standards can only be used for building materials, plastic products and bamboo and other industrial products, never allowed to use in food. However, due to the good anti-mildew effect, some illegal manufacturers will add it to the food, not only can make the food not easy to mildew, long shelf life, and bright color. But it is harmful to the human body, will damage the intestines, internal organs and cause allergies, especially for children's growth and development will cause great harm.
disabling regulations
DMF background:
EU meeting to ban the use of dimethyl fumarate
On December 16, 2008, AQSIQ issued the 4th risk warning notice of 2008, pointing out that the European Commission's non-food rapid warning system issued a consumer warning on a lying-down sofa produced by a Chinese enterprise. Due to the use of DMF-containing mildewproofing agents in the sofa, there is a risk of skin irritation in the consumer. France signed a decree on December 4, 2008, which prohibits the import and marketing of chair and footwear products containing DMF, it is also required that all seat and footwear products containing a detectable amount of DMF in the product or package be recycled. Belgium has also issued legislation prohibiting the import and marketing of all articles and products containing DMF. Spain has enacted measures to ban the use of DMF in all skin-accessible consumer products.
Response: This EU resolution regulates a wide range of products, including all products in the EU market, so the resolution will affect the export industry.
At the same time, the EU regulation is very strict: the market or sale of products containing DMF is prohibited, and the recall of products containing DMF that have been put on the market or sold on the market is required, its content limit is 0.1mg/kg. Therefore, the export enterprises should pay close attention to ensure that the export products meet the requirements of the EU DMF ban, in order to avoid losses.
Can proceed from the following aspects:
1, the overall response of the supply chain, all material suppliers are required not to intend to use DMF, also can not cause pollution in the process. To reduce risk, DMF is added to the non-use of hazardous substances guarantee signed by the supplier. Proof of material not containing DMF may be requested if necessary;
2, enterprises should establish a hazardous substance control system, in order to be durable, low-cost response to relevant regulatory requirements; For incoming materials and shipments should be implemented sampling, especially moisture-proof bags and other high-risk products to implement strict sampling, ensure compliance;
3, the establishment of a sound traceability system, do a good job of product identification. When there is an excessive situation, you can lock in the problem product range, in order to minimize the loss.
Product Standard
1, "DMF" refers to the chemical Dimethyl fumarate, IUPAC (International Union of Pure and Applied Chemistry) named Dimethyl (E)-butenedioate,CAS (chemical substance registration number) number: 624-49-7,EINECS (European inventory information system for existing commercial chemicals) No: 210-849-0.
2. "product" means any product as defined in Article 2(a) of Directive 2001/95/EC;
3. "products containing dimethyl fumarate" means the following products or product parts:
(I) the rate of presence of dimethyl fumarate is stated, as in one or more small bags; Or
(ii) a concentration of dimethyl fumarate greater than 0.1 mg/kg of weight of the product or part of the product;
4, "put on the market" refers to the first time in the Community market sales;
5, "on the market" refers to the process of commercial activities to provide for distribution in the Community market, consumption or use, whether paid or unpaid. The National leather quality supervision and inspection center (Zhejiang) began to focus on prospective research in 2008 to deal with the technical measures of trade technology, in the second half of 2008 has taken the lead in providing this testing technology services. Since 2008, China's leather products used in Europe containing DMF mildewproofing agent suspected consumer allergy incidents, mainly related to products including chairs and shoes, the end of in France, spain banned the import of chairs containing DMF, and last month EU countries passed a decision to ban the import of DMF.
Last Update：2024-04-10 22:29:15
Dimethyl fumarate - Use
dimethyl fumarate is abbreviated as DMF. It has low toxicity (LD_(50) rats oral 2240 mg/kg), high efficiency, broad-spectrum antibacterial characteristics, the mold has a special inhibitory effect. Can be applied to bread, feed, cosmetics, fish, meat, vegetables and fruits of mold. The antifungal effect of DMF for bread is much better than that of calcium propionate. According to domestic research, DMF has good antifungal ability, better than propionate, sorbic acid and benzoic acid and other acidic preservatives for feed, in the PDA medium containing 500~800 ppm, it has a complete inhibitory effect on many molds and bacteria.
Last Update：2024-04-09 21:21:28
Dimethyl fumarate - Supplementary Information
| fungicide | dimethyl fumarate is a new atmosphere-type fungicide. White powder crystals at room temperature, melting point 102~104 ℃, specific gravity 1.37, slightly soluble in water, soluble in ethyl acetate, chloroform and alcohol, sublimation, low toxicity, rats oral 50=2628mg/kg, the maximum non-acting dose of 50mg/kg, with a broad, efficient, low toxicity, low cost and other characteristics, in addition to a good antibacterial and bactericidal effect, but also have insecticidal effect. With contact sterilization and fumigation sterilization dual role. The use of this product is extremely safe, and there is no residue after human and animal metabolism. Several examples have shown that dimethyl fumarate can cause serious reactions such as skin burning or allergy through skin contact. In addition, this product is also irritating, should avoid contact with the eyes. Scope of Application: Anti-mildew of food. DMF used in bread, moon cake, cake and other food mold, preservation effect is good. The dosage was only 0.05%. Grain storage. The right amount of DMF directly added to rice, flour, shelf life of more than 200 days, but also the grain of red like the Valley steal, corn, Valley, Long Horn Valley steal, etc to kill, ensure the quality of grain storage. Anti-mildew of feed. Such as to DMF-based preparation of reducing mold King is a highly efficient feed fungicide. Fruit Preservation, especially the effect of citrus. Anti-mildew of silkworm cocoon. Anti-mildew and anti-cavity. |
| chemical properties | powder crystals. Melting point 103-104 °c, boiling point 193 °c. The relative density was 1.37. Soluble in ethyl acetate, chloroform, acetone and alcohols, ether-soluble, insoluble in water. Rat oral ld502.628 g/kg. |
| purpose | as a feed fungicide. |
| purpose | is widely used in food, food, feed, tobacco, leather and clothing and other anti-mildew and preservation |
| purpose | can volatilize slowly for a long time and effectively kill the growth of mold. |
| production method | (1) fumarate esterification method. DMF was directly synthesized from fumaric acid and methanol in the presence of catalyst. The catalysts include boron trifluoride, ferric chloride hexahydrate (FeCl3 · 6H2O), sulfuric acid or phosphoric acid, and the yield is as high as 92%. Cationic resin catalyst can also be used, using Catalytic distillation technology, esterification reaction at 80-85 deg C for 5H. (2) isomerization of maleic acid. Maleic acid and methanol in the catalyst, isomerization, esterification to get DMF, Catalyst HCl-H2SO4 and phosphotungstic acid. When HCl-H2SO4 is used as the catalyst, the reaction is actually carried out in two steps, that is, HCl catalyzed isomerization reaction and H2SO4 catalyzed esterification reaction. Maleic acid was refluxed with concentrated hydrochloric acid and water for 30min to obtain 91% fumaric acid; Fumaric acid was refluxed with methanol and concentrated sulfuric acid for 12h to obtain 91.9% product. Phosphotungstic acid is a composite catalyst that catalyzes both isomerization and esterification. Maleic acid and methanol were refluxed for 4H in the presence of Phosphotungstic acid to obtain 89.4% of the product. (3) the oxidation and esterification of sugar aldehyde. Using furfural as raw material, the synthesis was carried out in two steps. Firstly, the furfural is oxidized to fumaric acid with KClO3 under the catalysis of V2O5, the reaction temperature is 95 ℃-105 ℃, the reaction time is 7h, the yield is 81.5%; Then fumaric acid is heated and refluxed with methanol in the presence of concentrated sulfuric acid, DMF was obtained with a reaction time of 10H. The yield was 86.0%. (4) hydrolysis and isomerization of maleic anhydride. Using maleic anhydride as raw material, and methanol under the action of catalyst to produce DMF. The catalysts were concentrated hydrochloric acid, hydrochloric acid-phosphoric acid, ferric chloride hexahydrate, P-toluenesulfonic acid and thiourea. Hydrochloric acid-Phosphoric acid is a composite catalyst, first hydrolysis, esterification reaction, get dimethyl maleate, the latter in bromine and light on the isomerization to get the product; Using thiourea as a catalyst, maleic anhydride first undergoes hydrolysis isomerization reaction to obtain fumaric acid, which is esterified in the presence of sulfuric acid to obtain the product. Example: A 9.8 mL flask was charged with 0.1g (8.1 mol) of maleic anhydride, 0.2 mL (1.5 mol) of methanol, mL of concentration, and heated under reflux for h. Then 12ml (0.3mol) excess methanol was added dropwise, and after dropping for 0.5H, reflux was continued for 2H. After completion of the reaction, methanol was distilled off, after being slightly cooled, 30ml of ethanol was added, and the solid was dissolved by heating. After cooling, crystals were precipitated. The two products were recrystallized once with ethanol and water respectively to obtain 12.3g of product, with a yield of 86.2% and a melting point of 103-104 ℃. |
Last Update：2024-04-09 20:49:11
Dimethyl fumarate - Industrial use
purpose
dimethyl fumarate is a new atmosphere-type fungicide. White powder crystals at room temperature, melting point 102~104 ℃, specific gravity 1.37, slightly soluble in water, soluble in ethyl acetate, chloroform and alcohol, sublimation, low toxicity, rats oral 50=2628mg/kg, the maximum non-acting dose of 50mg/kg, with a broad, efficient, low toxicity, low cost and other characteristics, in addition to a good antibacterial and bactericidal effect, but also have insecticidal effect. With contact sterilization and fumigation sterilization dual role. The use of this product is extremely safe, and there is no residue after human and animal metabolism. Several examples have shown that dimethyl fumarate can cause serious reactions such as skin burning or allergy through skin contact. In addition, this product is also irritating, should avoid contact with the eyes. [3]
range
Anti-mildew of food. DMF used in bread, moon cake, cake and other food mold, preservation effect is good. The dosage was only 0.05%.
grain storage. The right amount of DMF directly added to rice, flour, shelf life of more than 200 days, but also the grain of red like the Valley steal, corn, Valley, Long Horn Valley steal, etc to kill, ensure the quality of grain storage.
mildew-proof feed. Such as to DMF-based preparation of reducing mold King is a highly efficient feed fungicide.
fruit preservation, especially the effect of citrus.
Anti-mildew of silkworm cocoon.
Anti-mildew and anti-cavity.
Industrial use
Product use dimethyl fumarate is a new type of fungicide developed in the United States in the 80 s, named "mildew enemy". With high efficiency, low toxicity (LD) rats to 2240mg/kg), many mold has a special inhibitory effect, and has anti-fungal ability, widely used in food, beverage, feed, Chinese herbal medicine, cosmetics, fish, meat, vegetables, fruits and other anti-mildew, anti-corrosion, anti-insect, preservation, according to reports, the United States to dimethyl fumarate for bread mold test, under the same conditions of storage of bread without mildew period, add calcium propionate bread for 16-30 days, and add dimethyl fumarate bread for 475 days, its efficacy is much better than calcium propionate. The results show that the eight kinds of common mold in food (such as Aspergillus flavus, Aspergillus niger, Penicillium, high Streptomyces, white mold, Fusarium moniliforme, etc.) it has obvious inhibitory effect, and the mold-proof effect for feed is better than that of the volatile solution prepared by propionic acid, sorbic acid and dimethyl benzoate, which is sprayed into the cabinet and the book cabinet, and also has a good mold-proof effect, fumaric acid diester is a kind of new fungicide in the development prospect, which is attracting the attention of food industry at home and abroad. Therefore, the development and production of dimethyl fumarate not only has practical significance but also has obvious economic and social benefits.
Last Update：2024-04-09 21:04:16
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Raw Materials for Dimethyl fumarate