CAS no.: 77-93-0
EC / List no.: 201-070-7
Triethyl citrate is an ester of citric acid.
Triethyl citrate is a colorless, odorless liquid used as a food additive (E number E1505) to stabilize foams, especially as whipping aid for egg white.
Triethyl citrate is also used in pharmaceutical coatings and plastics.
Triethyl citrate is also used as a plasticizer for polyvinyl chloride (PVC) and similar plastics.
Triethyl citrate is used in the following products:
cosmetics and personal care products,
perfumes and fragrances,
air care products, w
ashing & cleaning products,
polishes and waxes,
biocides (e.g. disinfectants, pest control products)
and coating products.
Other release to the environment of this substance is likely to occur from:
indoor use (e.g. machine wash liquids/detergents,
automotive care products,
paints and coating or adhesives,
fragrances and air fresheners) and outdoor use.
A continuous reactive distillation process is proposed for the synthesis of triethyl citrate from citric acid and ethanol in the presence of macroporous Amberlyst 15 ion-exchange resin catalyst.
Triethyl citrate design, developed using ASPEN Plus simulation software, is based on laboratory kinetic and thermodynamic studies and pilot-scale reactive distillation experiments.
Pilot-scale experiments were carried out in a 5-m glass reactive distillation column; catalyst effectiveness was then determined from ASPEN Plus simulation of pilot-scale experiments using a user-written reaction kinetic module based on activity coefficients.
Because citric acid esterification kinetics are slow, complete conversion could not be obtained in the pilot-scale column.
Using parameters determined from simulation of a pilot-scale column experiment, design of a reactive distillation column to completely convert citric acid to triethyl citrate was carried out.
Optimum column performance occurs at low reflux ratios (L/D < 0.1) to avoid water reintroduction and at moderately elevated pressure (2.5 bar) to increase temperature and enhance kinetic rates without leading to product degradation.
The effect of ethanol feed position and values of reflux and boilup ratios were also examined.
A large number of reactive stages is required because of the slow reaction of diethyl citrate to triethyl citrate.
As a final step, the design of a complete commercial-scale process to produce 25 million lbs/y triethyl citrate, with the reactive distillation column as the core component, was carried out.
Three different process schemes were examined.
In the first scheme, only a reactive distillation column is used.
The second uses a prereactor followed by a reactive distillation column.
In the third and preferred scheme, a prereactor followed by a simple distillation column to remove water is placed ahead of the reactive distillation column.
In each configuration, triethyl citrate product yield is maintained above 98.5 wt %, with the main byproduct being diethyl citrate.
Comparison of stream compositions and equipment design parameters is provided for the three schemes considered.
Triethyl citrate is an ester of Citric Acid.
Connect Chemicals is offering different grades of this product suitable for industrial as well as food and pharma applications.
Applications
Triethylcitrate is used as plasticizer in e.g. adhesives, inks, sealants, plastics and coatings.
Here it does primarily reduce hardness of polymers and can be further used to regulate viscosity.
In the personal care industry Triethyl citrate used as solvent or diluent as well as a fixative for perfumes.
As an active ingredient Triethyl citrate can be also used in deodorants.
Triethyl citrate is produced by the process of esterification of citric acid with ethanol.
Triethyl citrate naturally present in small amounts in wine and is easily metabolized by the human body.
In cosmetics, this ingredient is often used in deodorants formulated as an alternative to aluminum salts.
Due to its ability to inhibit the enzymatic breakdown of sweat components, Triethyl citrate an excellent active ingredient in combating body odor.
Triethyl citrate also exhibits antibacterial properties.
Organically authorized.
Triethyl citrate acts as a plasticizer for polyvinylchloride and plastics.
Triethyl citrate also useful in pharmaceutical coatings.
Triethyl citrate employed as a dye entrapment for the preparation of emission membrane filters for contact fluorescence imaging.
Triethyl citrate also employed in fabrication of green nanocomposites from cellulose acetate.
Triethyl citrate finds application as a pseudo-emulsifier in e-cigarette juices.
Further, Triethyl citrate functions like Lecithin and utilized in food products.
In addition to this, Triethyl citrate acts as a carrier reagent and sequestrant.
Formula C12H20O7
Melting point -55°
Flash Point 176°(348°F)
Refractive Index 1.4420
Solubility Miscible with water,
alcohol and diethyl ether.
Formula Weight2 76.29
Boiling Point 126-127°/1mm
Density 1.137
Storage & Sensitivity Ambient temperatures.
Triethyl Citrate (CAS 77-93-0) is an ester of citric acid with several industrial and consumer applications.
Triethyl citrate produced via fermentation of ethanol and natural citric acid.
This colorless, odorless liquid is often used as a food additive where it acts as both a flavoring agent and a foam stabilizer, principally as a whipping enhancer for organic egg whites during processing.
In the cosmetics and personal care sector, triethyl citrate is used as a perfume fixer and as a film for hair sprays and nail polish.
Triethyl citrate also an active ingredient in many deodorants.
Triethyl citrate readily biodegradable and considered to have low toxicity prior to degradation.
The manufacture of certain pharmaceutical coatings and plastics involves use of triethyl citrate, where Triethyl citrate acts as a plasticizer for natural resins and cellulose derivatives.
Polyvinyl chloride (PVC) is one example.
Triethyl citrate has been used as a pseudo-emulsifier in e-cigarette juices.
Triethyl citrate functions as a stabilizer in much the same way that lecithin does in many food products, but with the possibility of vaporization which lends itself to this unique application.
As manufactured, triethyl citrate is stable under normal use conditions.
Contact with strong oxidizing agents should be avoided, as should exposure to extreme heat, open flames, or other potential sources of ignition.
Triethyl citrate is an ester of citric acid.
Triethyl citrate a colorless, odorless liquid used as a food additive.
Triethyl citrate stabilizes foams, especially as an egg white whisking aid.
Triethyl citrate also used in pharmaceutical coatings and plastics.
Triethyl citrate is also used as a plasticizer for polyvinyl chloride and similar plastics.
Triethyl citrate is a balance of ethyl alcohol and citric acid.
Triethyl citrate used in coatings and plastics in the pharmaceutical industry.
According to the FDA Select Committee, generally recognized as safe foodstuffs, triethyl citrate salts citrate are generally considered safe when used in normal amounts.
Triethyl citrate (TEC) is the triethyl ester of citric acid.
Triethyl citrate formed by the esterification of citric acid where ethyl groups from the ethanol replace all three of the carboxyl groups in the citric acid.
Triethyl citrate occurs naturally as a component of plant and animal tissues.
Commercial sources of Triethyl citrate are produced from the reaction of citric acid and ethyl alcohol (ethanol), both of which are
fermentation products from the microbial digestion of a carbon substrate.
Citric acid is also produced from the fungal
Triethyl Citrate (TEC) is a non-phthalate cosmetic ingredient for skin care.
Triethyl Citrate is a versatile cosmetic ingredient with excellent skincare properties manufactured from nature-derived agro resources.
Triethyl citrate non-toxic, eco-friendly and bio-degradable made from 100 % renewable carbon source.
The ingredient is suitable for several applications such as personal care, health care, food and beverage, industrial applications, cleaners and detergents.
Acetyl Triethyl Citrate is produced via the reaction of citric acid triethyl ester with acetic acid anhydride (80±C; H2SO4 and Acetyl Tributyl Citrate is pro- duced via the reaction of tri-n-butyl citrate with acetic anhy- dride (acetylation).
According to another source, Acetyl Triethyl Citrate and Acetyl Tributyl Citrate are produced via the esteri cation and acetylation of citric acid
Triethyl citrate is a colorless, odorless, citric acid derivative used as a stabilizing food additive and pharmaceutical and polymer plasticizer.
Citric acid esters are commonly obtained by direct esterification of citric acid and alcohols (e. g. ethanol, butanol), using acid catalysts.
The process occurs in a series-parallel reaction scheme, where the monoalkyl citrate is initially obtained, followed by the formation of the diester, and finally Trialkyl citrate.
In the case of reacting with ethanol; methyl, diethyl and triethyl citrate (TEC) are the reaction products.
The Citric acid that is the raw material for these esters is produced by fermentation.
The downstream processing for its purification is complex and depending on the separation technology, it may require precipitation with calcium, extraction with amines or solvents, chromatographic separation, evaporation and several crystallization steps.
All these processes are energy intensive and make citric acid an expensive raw material for the production of commodities such as the plasticizers.
Alternatively, this work evaluated the production of TEC from a calcium salt usually obtained during the precipitation process.
Calcium citrate is a fine-white solid, insoluble in water and in ethanol.
Triethyl citrate production was carried out by an acidification process of the calcium salt in an alcoholic medium using sulfuric acid.
During the process, a first reaction step of ion exchange mechanism occurred (reaction between sulfuric acid and calcium citrate to produce calcium sulfate and citric acid in solution), and then the simultaneous esterification of the dissolved citric acid occurred.
The latter reaction is catalyzed by the sulfuric acid remaining in the reaction mixture.
The experimental study was carried out using the Box-Benhken method where three variables were considered:
Temperature, ethanol to calcium salt molar ratio, and sulfuric acid loading.
Experiments were carried out in agitated test tubes under isothermal conditions.
To reproduce a batch experiment, for each experimental condition, several tubes were loaded with identical initial compositions, but removed from the isothermal system at different times.
This allowed to obtain a kinetic profile to follow reaction performance.
After calcium sulfate removal, the reacting media was sampled and analyzed by using liquid chromatography.
Results indicated that TEC can be obtained directly from the calcium salt, avoiding the purification of citric acid for the traditional esterification route.
A kinetic model of the process was established and it can be used for process up-scaling.
Triethyl citrate may enhance antimicrobial activity.
Addition of Triethyl citrate improves the texture of pasta when microwaved, facilitates low temperature drying without cracking, and reduces cooking moisture losses.
Triethyl citrate is also used as a flavoring agent, a solvent, and in food coatings, food contact materials and food packaging .
In general, it serves as a carrier solvent and a sequestrant
The Codex Alimentarius General Standard for Food Additives (GSFA) Provisions for TEC include use in dried and/or heat coagulated egg products, liquid egg products, and in water-based flavored drinks, including “sport,” “energy,” or “electrolyte” drinks .
Non-food uses of Triethyl citrate are as a plasticizer, an agglutinant, and a sequestrant.
Applications include in toys, pharmaceutical and medical products, cigarettes, printing ink coatings, cosmetics, perfumes and lacquers.
Triethyl citrate known as an environmentally friendly, non-toxic plasticizer that can replace the highly persistent plasticizers such as phthalates .
Triethyl citrate also used as a fragrance carrier , an antioxidant, and is an active ingredient in deodorant products.
Triethyl citrate is used in the following products:
cosmetics and personal care products, perfumes and fragrances, air care products, washing & cleaning products, polishes and waxes, biocides (e.g. disinfectants, pest control products) and coating products.
Other release to the environment of this substance is likely to occur from:
indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.
Other release to the environment of this substance is likely to occur from:
outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Triethyl citrate can be found in complex articles, with no release intended:
vehicles and machinery, mechanical appliances and electrical/electronic products (e.g. computers, cameras, lamps, refrigerators, washing machines).
Triethyl citratee can be found in products with material based on:
plastic (e.g. food packaging and storage, toys, mobile phones), stone, plaster, cement, glass or ceramic (e.g. dishes, pots/pans, food storage containers, construction and isolation material) and metal (e.g. cutlery, pots, toys, jewellery).
IUPAC names:
1,2,3-Propanetricarboxylic acid, 2-hydroxy-, 1,2,3-triethyl ester
1,2,3-Propanetricarboxylic acid, 2-hydroxy-, triethyl ester
2-Hydroxy-1,2,3-propanetricarboxylic acid, delta triethyl ester
2-Hydroxy-1,2,3-propanetricarboxylic acid, triethyl ester
Citric acid, triethyl ester
citric acid, triethyl ester
Citroflex 2
Ethyl citrate
Eudraflex
Hydragen CAT
Triaethylcitrat
Triethyl 2-hydroxy-1,2,3-propanetricarboxylate
Triethyl citrate
Triethylester kyseliny citronove
synonyms:
1,2,3-Propanetricarboxylic acid, 2-hydroxy-, triethyl ester
201-070-7
2OV1XQVO2&1VO2
3083
77-93-0
8Z96QXD6UM
Citrate de triéthyle
Citric acid triethyl ester
Citric acid, triethyl ester
ethyl citrate