2-hydroxypropane-1,2,3-tricarboxylate
Citric acid
CAS: 77-92-9
Molecular Formula: C6H8O7
2-hydroxypropane-1,2,3-tricarboxylate - Names and Identifiers
| Name | Citric acid |
| Synonyms | BETZ 0623 BETZ 6251 Citric acid Citric acid anhydrous Citric acid anhydride BUFFER CONCENTRATE, PH 9.00 BUFFER CONCENTRATE, PH 8.00 BUFFER CONCENTRATE, PH 7.00 2-hydroxypropane-1,2,3-tricarboxylate 2-Hydroxy-1,2,3-propanetricarboxylic acid BORIC ACID-POTASSIUM CHLORIDE-SODIUM HYDROXIDE BUFFER Citric acid, anhydrous, USP Grade 1,2,3-Propanetricarboxylic acid, 2 hydroxy-citric acid, anhydrous, USP Grade |
| CAS | 77-92-9 |
| EINECS | 201-069-1 |
| InChI | InChI=1/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/p-3 |
| InChIKey | KRKNYBCHXYNGOX-UHFFFAOYSA-N |
2-hydroxypropane-1,2,3-tricarboxylate - Physico-chemical Properties
| Molecular Formula | C6H8O7 |
| Molar Mass | 192.12 |
| Density | 1.67 g/cm3 at 20 °C |
| Melting Point | 153-159 °C (lit.) |
| Boling Point | 248.08°C (rough estimate) |
| Flash Point | 100 °C |
| JECFA Number | 218 |
| Water Solubility | soluble in Water (1174g/L at 10°C, 1809g/L at 30°C, 3825g/L at 80°C). |
| Solubility | Soluble in water 750g/L (20°C), ethanol, ether, insoluble in benzene, slightly soluble in chloroform |
| Vapor Presure | <0.1 hPa (20 °C) |
| Vapor Density | 7.26 (vs air) |
| Appearance | White crystalline powder |
| Color | White |
| Odor | Odorless |
| Maximum wavelength(λmax) | ['λ: 260 nm Amax: 0.20', , 'λ: 280 nm Amax: 0.10'] |
| Merck | 14,2326 |
| BRN | 782061 |
| pKa | 3.14(at 20℃) |
| PH | 3.24(1 mM solution);2.62(10 mM solution);2.08(100 mM solution); |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with bases, strong oxidizing agents, reducing agents, metal nitrates. |
| Sensitive | Hygroscopic |
| Explosive Limit | 8%, 65°F |
| Refractive Index | 1.493~1.509 |
| MDL | MFCD00011669 |
| Physical and Chemical Properties | Relative density 1.542, melting point 153 ℃ (water loss), refractive index 1.493~1.509 colorless translucent crystals or white particles, or white crystalline powder, often containing a molecule of crystal water, odorless, extremely sour taste, soluble in water, alcohol and ether. Its calcium salt is more soluble in cold water than hot water, and this property is often used to identify and isolate citric acid. Anhydrous citric acid can be obtained by controlling the appropriate temperature during crystallization. The aqueous solution was acidic. It is slightly weathered in dry air and deliquescent in moist air. Above 175 deg C and carbon dioxide free water. |
| Use | Used as experimental reagents, chromatographic analysis reagents and biochemical reagents, also used in the preparation of buffer. It is used in the food industry in particular as an acidifying agent, a PH buffering agent, and together with other compounds as a preservation agent. In the detergent industry, it is an ideal substitute for phosphate. Boiler chemical cleaning pickling agent, boiler chemical cleaning rinsing agent. It is mainly used as a sour agent for food, and is also used for the preparation of medical coolants and detergents? |
2-hydroxypropane-1,2,3-tricarboxylate - Risk and Safety
| Risk Codes | R41 - Risk of serious damage to eyes R36/37/38 - Irritating to eyes, respiratory system and skin. R36/38 - Irritating to eyes and skin. R37/38 - Irritating to respiratory system and skin. R34 - Causes burns R36 - Irritating to the eyes R35 - Causes severe burns R61 - May cause harm to the unborn child R60 - May impair fertility |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S37/39 - Wear suitable gloves and eye/face protection S24/25 - Avoid contact with skin and eyes. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36 - Wear suitable protective clothing. S53 - Avoid exposure - obtain special instructions before use. |
| UN IDs | UN 1789 8/PG 3 |
| WGK Germany | 1 |
| RTECS | GE7350000 |
| FLUKA BRAND F CODES | 9 |
| TSCA | Yes |
| HS Code | 2918 14 00 |
| Toxicity | LD50 in mice, rats (mmol/kg): 5.0, 4.6 i.p. (Gruber, Halbeisen) |
2-hydroxypropane-1,2,3-tricarboxylate - Upstream Downstream Industry
2-hydroxypropane-1,2,3-tricarboxylate - Nature
Open Data Verified Data
citric acid is divided into two types: anhydrous and monohydrate. Translucent crystals or white fine powder crystals. Odorless, with strong sour taste. Dry or heated to 40~50 ℃ to become anhydrous, anhydrous weathering in dry air, micro deliquescence. 75 ℃ soft. 100 ℃ melting. Relative densities were 542(-hydrate) and 1.67 (anhydrous). Readily soluble in water (monohydrate 209g]lOOmL,25 °c; Anhydrous 59. 2G/lOOmL,20 °c; 1% solution pH 2.31) and ethanol, soluble in ether. Natural products are found in citrus fruits such as lemon. The powder and air can form an explosive mixture. In case of open flame, high heat or contact with oxidant, there is a risk of combustion explosion.
Last Update：2024-01-02 23:10:35
2-hydroxypropane-1,2,3-tricarboxylate - Preparation Method
Open Data Verified Data
sugar, molasses, starch, starch residue or glucose as raw material, through fermentation, separation, purification.
Last Update：2022-01-01 09:29:46
2-hydroxypropane-1,2,3-tricarboxylate - Use
Open Data Verified Data
citric acid has a strong chelating effect, which can complex Fe3 + and weaken the Promoting Effect of Fe3 + on corrosion. Can remove iron, copper and other metal oxide scale, easy to operate, safe, suitable for a variety of materials. Since the molecule does not contain c1-it will not cause stress corrosion of the equipment, used as a cleaning agent, citric acid than hydrochloric acid on steel corrosion rate is small. Citric acid is mainly used to remove rust and has poor solubility in calcium, magnesium and silicon scale, so it is mainly used for cleaning newly built large-scale devices. Citric acid can not remove calcium and magnesium scale and silicate scale, however, citric acid and amino sulfonic acid, glycolic acid or formic acid mixed use, can be used to clean the rust and calcium and magnesium scale citric acid and EDTA mixture, can be used to clean the heat exchanger. The corrosion inhibitor added in the citric acid cleaning solution is mainly thiourea, the dosage is 0. 1%, and 0.06% thiourea can also be mixed with other corrosion inhibitors. In addition, it can also be used in the field of medicine, sodium citrate salt can prevent blood coagulation, calcium salt can be used as the acid solution of the stomach, barium salt is toxic.
Last Update：2022-01-01 09:29:47
2-hydroxypropane-1,2,3-tricarboxylate - Safety
Open Data Verified Data
mice and rats were intraperitoneally injected with LD50: 5.0 mmol/kg, 4.6mmol/kg. Concentrated citric acid solution has a stimulating effect on the mucosa. Store in a cool, ventilated warehouse. Keep away from fire and heat source. The container is sealed. Should be stored separately from the oxidant.
Last Update：2022-01-01 09:29:47
2-hydroxypropane-1,2,3-tricarboxylate - Reference Information
| FEMA | 2306 | CITRIC ACID |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | anhydrous citric acid is a natural ingredient in animals and plants and an intermediate product of physiological metabolism, one of the most widely used organic acids in chemical industry and other fields. It is colorless transparent or translucent crystals, or granular, granular powder, odorless, although there is a strong sour taste, but pleasant, slightly after astringent. It is gradually weathered in warm air and slightly deliquescent in humid air. |
| natural distribution | citric acid is widely distributed in nature, existing in plants such as lemon, citrus, pineapple, gooseberry, raspberry, grape juice and other fruits and animal bones, muscles, blood. Synthetic citric acid is sugar, molasses, starch, grape and other sugar-containing substances produced by fermentation, can be divided into anhydrous and hydrate two. Pure citric acid is colorless transparent crystal or white powder, odorless, has an attractive sour taste. The translucent colorless crystals obtained from the hot concentrated aqueous solution were anhydrous and had a melting point of 153 °c. The translucent colorless crystals obtained from the cold water solution were monohydrate with a density of 1.542. Softening at 75 °c and melting at about 100 °c. A water substance may lose water in dry air. Is a strong organic acid. Soluble in water, ethanol and ether. Used in the manufacture of drugs, soda, candy, etc., but also used as a metal detergent, mordant, etc. A wide variety of fruits and vegetables, especially citrus fruits, contain more citric acid, especially lemon and lime-they contain a lot of citric acid, after drying, the content can reach 8% (about 47g/L in fruit juice). In citrus fruits, the content of citric acid is between 0.005 mol/L for Orange and grape and 0.30 mol/L for lemon and lime. This content varies with the growth of different cultivars and plants. |
| History of discovery | The Discovery of citric acid began in the 8th-century with the Iranian aldrant Jabier. 1784 C.W. Scheler first isolated citric acid by crystallization from lemon juice. It is prepared by adding milk of lime to the juice of fruit to form a calcium citrate precipitate. natural citric acid is widely distributed in nature, in plants such as lemon, citrus, pineapple and other fruits and animal bones, muscle, blood are contained. Originally found in California, Italy, and the West Indies. Italy ranks first in production. The production of citric acid by fermentation began at the end of the 19th century. In 1893, Weemer discovered that Penicillium can produce citric acid from sugars. However, the industrial use of microorganisms to produce citric acid was not on the agenda until the First World War hindered the export of lemon in Italy. 1913b. Zahosky reported that Aspergillus niger could produce citric acid. In 1916, Tom and Corey were tested with Aspergillus, and it was confirmed that most Aspergillus such as Aspergillus sojae, Aspergillus oryzae, Aspergillus Wenshi, Trichoderma viride and Aspergillus Niger have the ability to produce citric acid, and the acid production ability of Aspergillus niger is stronger. For example, Aspergillus niger was used as the test strain to ferment in 15% sucrose medium, and the absorption rate of sugar reached 55%. The first plant in the world for the production of citric acid by Aspergillus niger shallow-dish fermentation was built by fizea Co. Then Belgium, Britain, Germany, the Soviet Union and so on have studied the successful fermentation production of citric acid. In this way, the method of extracting natural citric acid from citrus is gradually replaced by fermentation. citric acid was produced by shallow-dish fermentation before 1950. A large-scale production of citric acid by submerged fermentation was carried out in the laboratory of Myers, USA in 1952. Since then, the submerged fermentation method was gradually established. Submerged Fermentation has the advantages of short cycle, high yield, labor saving, small footprint, easy to achieve instrument control and continuous, this manufacturing technology is still the most important manufacturing method. In this technique, Aspergillus niger is cultured in a medium containing sucrose or glucose to produce citric acid. Sources of sugars include corn steep liquor, molasses fermentation broth, hydrolysates of corn flour, or other inexpensive sugar solutions. After the mold is removed, calcium hydroxide is added to the remaining solution to react the citric acid to form a calcium citrate precipitate. After the precipitate is separated, sulfuric acid is added to obtain citric acid. |
| application in the food industry | anhydrous citric acid is known as the first edible acid, china's GB2760-1996 regulations for the allowed use of food acidity regulator. In the food industry, it is widely used as a sour agent, a solubilizer, a buffer, an antioxidant, a deodorizing agent, a chelating agent, and the like, and the specific uses thereof are numerous. According to statistics at home and abroad, the consumption of citric acid in the beverage industry accounts for 75% ~ 80% of the total citric acid production. Citric acid is one of the natural ingredients of fruit juice, not only can give fruit flavor but also solubilization, Buffering, antioxidant and other effects, so that the sugar, flavor, pigment and other ingredients in the beverage blend and coordinate to form a harmonious taste and aroma, can increase the anti-microbial antiseptic effect. Therefore, it is widely used in the formulation of various fruit-type soft drinks, for example, fruit-type soft drinks generally have an acid addition of between 0.10% and 0.25%. For non-co2-filled beverages, such as water, fruit juices, sugars, acids, colors, flavor mixtures, citric acid is used to adjust the pH to a certain acidity such that the titrated acidity of the product is between 0.25% and 0.40%. For the pulp type solid beverage powder, the addition amount of citric acid can be increased to 1.5% ~ 5.0%. In recent years, with the continuous improvement of living standards of urban and rural people, the demand for various beverages has increased greatly. It can be predicted that the consumption of citric acid in beverage industry will increase greatly in the future. 2. Jam and jelly the effect of citric acid in jam and jelly is similar to that in beverages, mainly adjusting the pH of the product and imparting a sour taste to the product, the pH having to be adjusted to a very narrow range optimum for the coagulation of pectin. Depending on the type of pectin used, the pH may be limited between 3.0 and 3.4. In the production of jam, the flavor can be improved and the defects of sucrose crystallization can be prevented. 3. Candy citric acid added to the candy can increase the sour taste and prevent the oxidation of various components and the precipitation of sucrose crystals. Generally sour candy may contain 2% citric acid. After boiling the sugar, citric acid is added along with the color and flavor during the cooling of the sugar paste. Citric acid can adjust the sour taste and enhance the gel strength in the production of pectin soft candy. Anhydrous citric acid is used for chewing gum and powder food. 4. Frozen food citric acid has the characteristics of chelating and pH adjustment, It can enhance the antioxidant effect and inactivate the enzyme, and can more reliably ensure the stability of frozen food. Citric acid, alone or in combination with isoascorbic acid, helps to extend the shelf life of frozen fish and shellfish. It can inactivate enzymes that can cause fish spoilage and shellfish deterioration and chelate trace elements. Seafood is generally soaked in 0.25% citric acid and 0.2% isoascorbic acid solution before freezing, which is beneficial to the preservation and cold storage. For fresh pork preservation, prevent corruption also has the effect. Citric acid can also inhibit the deterioration of the color and aroma of frozen fruits, which is also a manifestation of the inhibition of the enzymes in the fruit and the prevention of the oxidation of trace elements, such: 0.1% to 0.3% citric acid is effective in combination with 0.001% to 0.002% isoascorbic acid. |
| application in the pharmaceutical industry | effervescence is a popular drug delivery system for oral ingredients, citric acid reacts with sodium carbonate or aqueous sodium bicarbonate to produce large amounts of CO2 (I. E., effervescence) and sodium citrate, which allows the active ingredients in the drug to rapidly dissolve and enhance taste. For example, laxatives and analgesics have a solubilizing effect. Citric acid syrup is Fever patients with a cool drink, with flavor, cooling, detoxification effect. citric acid is widely used in various nutritional oral liquids, etc., buffering pH 3.5~4.5, maintaining the stability of active ingredients, strengthening the effect of preservatives. The combination of citric acid and fruit flavor gives people a favorite flavor to mask the bitter taste of drugs, especially traditional Chinese medicine. Adding 0.02% citric acid in liquid ingredients can form a complex of trace iron and copper, delay the degradation of active ingredients. The use of 0.1% ~ 0.2% citric acid in the chewing tablet can improve the flavor of the tablet and make it have a lemon flavor. |
| application in industry | 1. Metal purification The citric acid-based metal purification formula can effectively remove the oxides formed on the surface of ferrous and non-ferrous metals, as a weak organic acid, it can cause slight damage to the metal surface layer, however, as a metal ion chelating agent, it accelerates the migration of metal oxides. In many steel pickling systems, in order to eliminate metal oxide stress cracks and to minimize the corrosion brittleness of high strength steel, citric acid is used to remove rust instead of inorganic strong acid. in boilers, heaters, superheater tubes and non-clean reactors and stainless steel equipment, citric acid is generally used for pre-washing and purification to remove iron and copper oxides, especially where the presence of chloride is not permitted. The purification reaction of citric acid solution should be carried out under the condition of higher than 37.8 ℃, and the purification time below 37.8 ℃ should be correspondingly prolonged, and the amount of citric acid used and the working conditions should be adjusted by increasing or decreasing the estimated amount of precipitation. citric acid is a highly efficient chelating cleaning agent, which is effective for calcium, magnesium, iron, chromium, copper and other dirt. It is widely used in the cleaning of various metal surfaces. in recent years, citric acid is suitable for the chemical treatment of metal purification, and is also suitable for the pollution-free ashing of waste solvents, the citric acid molecules are burned into CO2 and water vapor in the ash and the valuable metals can be recovered from the ash, and the toxic or radioactive elements can be fully enclosed for chemical treatment. 2. sodium citrate can increase the decontamination performance, accelerate the biodegradation in many household detergent products, and can be used as a substitute for phosphate, which is widely used in washing powder and detergent, sodium citrate is effective in enhancing the cleaning effect of the detergent together with the aluminosilicate. Technical grade 50% citric acid solution is used as the starting material in these products. In non-synthetic detergent solutions, citric acid is also used in cleaning agents for hot water extraction of carpet, baths and softeners for textiles due to its buffering effect and ability to chelate trace metals. Soilless cultivation of agronomy The use of trace element plant nutrient solution in soilless culture abroad has been very common, in the domestic also began to develop. In order to remove some excess elements such as copper, zinc, manganese and chromium in the soil, Citric acid is generally used to chelate such elements. The use of citric acid instead of phosphate can achieve satisfactory results. Mineral and pigment applications citric acid has dispersion efficiency, it can reduce the viscosity of some important slurry raw material. In mining such as phosphate rock powder in the hydraulic transport of viscosity problems often become the main reason for the expansion of clay, the use of citric acid treatment can control the expansion, so that the slurry raw material easy to transport. Citric acid can also reduce the precipitation of the concentrated raw meal of titanium dioxide, making it easy to handle and transport as a whole. Citric acid can also be used as a dispersant for low-grade sizing, paint and textile raw material processing, and titanium dioxide. |
| Klinefelter cycle | citric acid is an important compound in the physiological conversion of fats, proteins and sugars to carbon dioxide. These chemical reactions are central to almost all metabolism and provide energy for higher organisms. Hans Adolf Krebs was awarded the 1953 Nobel Prize in Physiology or Medicine for his discovery of this series of reactions. This series of reactions is referred to as the "citric acid cycle", "tricarboxylic acid cycle", or "Kjeldahl cycle". |
| solubility in water | 10 ℃-54.0%;20 ℃-59.2%;30 ℃-64.3%;40 ℃-68.6%;50 ℃-70.9%;60 ℃-73.5%;70 ℃-76.2%;80 ℃-78.8%;90 ℃-81.4%;100 ℃-84.0% |
| Use | is mainly used as a acidulant in food, and also used in the preparation of pharmaceutical cooling agents, detergent additives used as experimental reagents, Chromatographic Reagents and biochemical reagents, also used in the preparation of buffer. It is used in the food industry in particular as an acidifying agent, a PH buffering agent, and together with other compounds as a preservation agent. In the detergent industry, it is an ideal substitute for phosphate. Boiler chemical cleaning pickling agent, boiler chemical cleaning rinsing agent. Mainly used for food acid, also used for the preparation of medicine cooling agent, detergent with citric acid is the most functional, the most widely used acid agent. High solubility, strong chelating ability to metal ions, can be used for all kinds of food, according to the production needs of appropriate use. In addition, this product can also be used as antioxidant Synergist, compound potato starch bleach synergist and preservative. It is widely used as an acidulant and a pharmaceutical additive for foods and beverages. Can also be used as cosmetics, metal cleaning agents, mordant, non-toxic plasticizer and Boiler Scale Inhibitor of raw materials and additives. Its main salt products are sodium citrate, calcium and ammonium salts, etc., sodium citrate is blood anticoagulant, ferric ammonium citrate can be used as blood medicine. used as analytical reagent with citric acid. |
| production method | This product is mainly produced by fermentation, and its raw materials can be molasses, sucrose, sweet potato, petroleum hydrocarbons and other carbohydrates. Generally, fungi are used for fermentation production, and can be divided into two categories: surface fermentation and submerged fermentation according to the fermentation method. Surface fermentation is an early production method, and some Penicillium or Aspergillus niger is used as the strain; the submerged fermentation method also uses Aspergillus niger as the strain to generate small spherical filamentous aggregates during the fermentation process. The growing and thin filamentous cells should be avoided, and the fermentation condition is pH 1.5-2.8, at the same time, sterile air should be introduced and stirred, and the fermentation is completed to remove Silk cells and residual solid waste. The filtrate is neutralized with calcium carbonate to obtain calcium citrate, and then neutralized with concentrated sulfuric acid to obtain crude citric acid, the product is refined, concentrated and crystallized by ion exchange resin. The yield of submerged fermentation was about 80%. citric acid can be extracted from fruits such as lemon and orange, and can also be synthesized by using oxaloacetic acid and ketene as raw materials. However, the current industrial production method at home and abroad is fermentation. The fermentation methods include solid fermentation, shallow fermentation and submerged fermentation. In China, more than 80% of citric acid is made from dry potato powder by submerged fermentation with Aspergillus niger, neutralization of calcium carbonate, acidolysis with sulfuric acid, refining, concentration, crystallization and drying. (1) fermentation the sweet potato powder is prepared into 18% ~ 22% slurry, and the fermentation tank which has been steam sterilized (0.2MPa,40~60min) is given. Heat to 110 °c for 20min with steam, Liquefaction was performed with 0.05% amylase. Fermentation was carried out by inoculation with Aspergillus Niger after cooling to 35 °c. The fermentation temperature was 36~38 ℃ in the early stage and 34~36 ℃ in the late stage. The aeration rate was 1:(0.1~0.2); The pH value was not less than 2.5; The fermentation period was 96H. The acid production level was 10% ~ 14%, and the conversion rate was 95%. (2) after completion of neutralization and fermentation, the fermentation broth was heated to 80 ° C. To kill mold, and then submitted to plate-and-frame pressure filtration to obtain a clear solution. The filtrate was neutralized to pH 5.0-5.5 by adding calcium carbonate powder at 80 ° C. And incubated for 0.5 hours. The calcium citrate is then obtained by vacuum suction filtration and washing with hot water at 80 °c. (3) acid hydrolysis and refining under constant stirring, calcium citrate is added to water or dilute acid, and then sulfuric acid is slowly added until the pH value is 1.8, heated to 90 ° C., and the end point is determined by double tube method. Then add the amount of citric acid 1%~ 3% of the activated carbon, insulation 0.5h, put the suction filter barrel to dry, and 90 deg C hot water to the residual acid below 0.5%, washing water (ie dilute acid) for the next acid solution. Finally, ion exchange was carried out with a 732 cation resin to remove various cations. (4) concentration, crystallization and drying the clear liquid after ion exchange contains about 15% to 20% of citric acid. At 55~60 0C: vacuum concentration to a relative density of 1.335~1.340, put into the crystallization pot. Aqueous crystals were precipitated by cooling to 36.6 ° C. Or lower with frozen brine. After the crystals were separated, they were washed with a small amount of distilled water until the content of sulfuric acid was below 200 × 10 ° C., and finally dried by hot air at 35 ° C. To obtain a finished product. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:15
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