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TRIMETHYL CITRATE

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CAS:1587-20-8
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TRIMETHYL CITRATE Basic information
Description Reference
Product Name:TRIMETHYL CITRATE
Synonyms:2,3-propanetricarboxylicacid,2-hydroxy-trimethylester;3-Hydroxy-3-methoxycarbonylpentanedioic acid, dimethyl ester;Trimethyl 2-hydroxy-1,2,3-propanetricarboxylate;METHYL CITRATE;CITRIC ACID TRIMETHYL ESTER;1,2,3-Propanetricarboxylic acid, 2-hydroxy-, trimethyl ester;TRIMETHYL CITRATE;2-Hydroxy-1,2,3-propanetricarboxylic acid trimethyl ester
CAS:1587-20-8
MF:C9H14O7
MW:234.2
EINECS:216-449-2
Product Categories:Miscellaneous;Functional Materials;Hydroxycarboxylic Acid Esters (Plasticizer);Plasticizer;C8 to C9;Carbonyl Compounds;Esters
Mol File:1587-20-8.mol
TRIMETHYL CITRATE Structure
TRIMETHYL CITRATE Chemical Properties
Melting point 75-78 °C
Boiling point 176 16mm
density 1.3363 (rough estimate)
vapor pressure 1.3hPa at 20℃
refractive index 1.4455 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Sparingly), Methanol (Slightly)
form Solid
pka10.43±0.29(Predicted)
color White to Off-White
Odorat 100.00 %. ethereal fruity
Odor Typeethereal
Water Solubility 53.2g/L at 20℃
BRN 1796169
LogP0.7 at 20℃
CAS DataBase Reference1587-20-8(CAS DataBase Reference)
EPA Substance Registry System1,2,3-Propanetricarboxylic acid, 2-hydroxy-, trimethyl ester (1587-20-8)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
HS Code 29181500
MSDS Information
ProviderLanguage
SigmaAldrich English
TRIMETHYL CITRATE Usage And Synthesis
DescriptionTrimethyl citrate is an ester of citric acid. It is a kind of non-toxic plasticizer1. Trimethyl citrate is one of the constituents of Dioscorea opposita2. The IC50 value for monoamine oxidase-B of trimethyl citrate was studied. It has various applications3: it can do the main flame retardant candle flame color, its melting point and can fully meet the flammability requirements of candle products. It can be used for the synthesis of pharmaceutical and pesticide. It can act as the main raw material for the production of citric acid hydrochloride, citric acid hydrochloride as well as the synthetic hot melt adhesive. It can also be used as the methyl methacrylate polymer a blowing agent, a stabilizer acrylamide, polyamide adhesive initiators, PVC plasticizers. It can also be used as solvent for household and II cleaner, film-former4.
Reference
  1. Huang, Li, L. I. Chun-Lian, and H. U. Qing-Guo. "Study on Catalytic Synthesis of Trimethyl Citrate by Solid Acid." Liaoning Chemical Industry (2012).
  2. https://www.sigmaaldrich.com/catalog/product/aldrich/27502?lang=en&region=US
  3. www.zhonglanindustry.com/product/trimethyl-citrate
  4. https://www.lookchem.com/Trimethyl-citrate/
Chemical PropertiesColorless crystals. M.P. 79℃. B.P. 287℃. (decomposes). Slightly soluble in water, soluble in alcohol and oils.
UsesTrimethyl Citrate is a reagent used in the preparation of citrate-ciprofloxacin conjugates which has antibacterial activity.
Preparation Trimethyl citrate is produced by direct esterification of Citric acid with Methanol using the old-fashioned method with 3% sulfuric acid and reflux to complete the esterification.
General DescriptionTrimethyl citrate is one of the constituents of Dioscorea opposita. The IC50 value for monoamine oxidase-B of trimethyl citrate was studied.
Flammability and ExplosibilityNot classified
Synthesis
Methanol

67-56-1

Citric acid

77-92-9

TRIMETHYL CITRATE

1587-20-8

(i) Synthesis of trimethyl citrate Citric acid (9.00 g, 46.8 mmol) was dissolved in anhydrous methanol and thionyl chloride (20.50 mL, 0.28 mol) was added slowly and dropwise at 0 °C and under nitrogen protection. The reaction mixture was stirred at 0 °C for 1 h, then warmed to room temperature and continued stirring overnight. Upon completion of the reaction, the volatile components were removed by distillation under reduced pressure. The resulting solid residue was recrystallized using a hexane/ethyl acetate solvent mixture to give 10.80 g of white crystalline trimethyl citrate in 98% yield. 1H NMR (acetone-d6, 200 MHz): δ 2.85 (dd, 4H, J1 = 15.4 Hz, J2 = 27.2 Hz); 3.60 (s, 6H); 3.72 (s, 3H); 4.50 (br.s, 1H). 13C NMR (acetone-d6): calculated value: M+ = 234.21.

References[1] Molecules, 2006, vol. 11, # 4, p. 263 - 271
[2] Patent: WO2007/14471, 2007, A1. Location in patent: Page/Page column 30
[3] Patent: US2013/89611, 2013, A1. Location in patent: Paragraph 0133-0135
[4] Molecules, 2018, vol. 23, # 9,
[5] RSC Advances, 2014, vol. 4, # 100, p. 57297 - 57307
TRIMETHYL CITRATE Preparation Products And Raw materials
Raw materialsMethanol-->Citric acid
Preparation ProductsCitrazinic acid
Tag:TRIMETHYL CITRATE(1587-20-8) Related Product Information
Triethyl citrate TRIMETHYL CITRATE tris(2-ethylhexyl) 2-(acetyloxy)propane-1,2,3-tricarboxylate STEARYL CITRATE n-Butyryl tri-n-hexyl citrate Tributyl citrate CITRIC ACID TRIALLYL ESTER CITRIC ACID TRI-N-PROPYL ESTER TRIS(2-ETHYLHEXYL)CITRATE Triethyl acetyl citrate Acetyl tributyl citrate Trihexyl O-acetylcitrate Citric acid TRI-N-AMYL CITRATE TRIISOOCTYL CITRATE COSTAUSOL(TM) SALOR-INT L160326-1EA TRI(N-OCTYLDECYL)ACETYL CITRATE

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