24555-16-6

Basic information

• Product Name: CITRIC ACID ANHYDRIDE
• Synonyms: CITRIC ACID ANHYDRIDE;Citric anhydride
• CAS NO: 24555-16-6
• Molecular Formula: C₆H₆O₆
• Molecular Weight: 174.10824
• Mol File: 24555-16-6.mol

Chemical Properties

• Boiling Point: 520.8±35.0 °C(Predicted)
• Appearance: /
• Density: 1.734±0.06 g/cm3(Predicted)
• PKA: 4.03±0.10(Predicted)
• CAS DataBase Reference: CITRIC ACID ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: CITRIC ACID ANHYDRIDE(24555-16-6)
• EPA Substance Registry System: CITRIC ACID ANHYDRIDE(24555-16-6)

Safety Data

• Hazardous Substances Data: 24555-16-6(Hazardous Substances Data)

Usage

Uses

Used in the Food and Beverage Industry:
Citric acid anhydride is used as a preservative, flavor enhancer, and acidulant for its ability to maintain freshness, improve taste, and provide a tangy flavor to food and beverages.
Used in the Pharmaceutical Industry:
Citric acid anhydride is used as a precursor in the synthesis of pharmaceutical compounds, contributing to the development of new drugs and medications.
Used in the Cosmetic Industry:
Citric acid anhydride is used in the formulation of cosmetic products, serving as a chelating agent, pH adjuster, and emulsifier to enhance product stability, texture, and efficacy.
Used in the Detergent and Cleaning Products Industry:
Citric acid anhydride is used as a builder in detergents and cleaning products, improving their cleaning performance and providing additional benefits such as stain removal and deodorization.
Used in the Production of Bio-based Materials:
Citric acid anhydride is used as a building block in the synthesis of bio-based materials, contributing to the development of sustainable and eco-friendly alternatives to petroleum-based products.
Used in the Synthesis of Organic Compounds:
Citric acid anhydride is used as a versatile building block in the synthesis of various organic compounds, enabling the creation of new chemical entities with potential applications in various industries.

Synthetic route

acetic anhydride (108-24-7) + citric acid (77-92-9) → citric acid anhydride (24555-16-6)

Conditions	Yield
at 52℃;	90%

citric acid (77-92-9) → citric acid anhydride (24555-16-6)

Conditions	Yield
With acetic anhydride; acetic acid at 38℃; for 20h;
With acetic anhydride; acetic acid at 40℃; for 20h; Inert atmosphere;

citric acid anhydride (24555-16-6) + butan-1-ol (71-36-3) → Citroflex-4 (77-94-1)

Conditions	Yield
With titanium(IV) isopropylate at 230℃; for 6h; Inert atmosphere;	97%

citric acid anhydride (24555-16-6) + hexan-1-ol (111-27-3) → tri(n-hexyl) citrate (16544-70-0)

Conditions	Yield
With titanium(IV) isopropylate at 230℃; for 6h; Inert atmosphere;	97%

citric acid anhydride (24555-16-6) + 2-Ethylhexyl alcohol (104-76-7) → tris(2-ethylhexyl)propane-1,2,3-tricarboxylate (7147-34-4)

Conditions	Yield
With titanium(IV) isopropylate at 230℃; for 6h; Inert atmosphere; Large scale;	97%

citric acid anhydride (24555-16-6) + 7-methyl-1-octanol (2430-22-0) → tri-isononyl citrate

Conditions	Yield
With titanium(IV) isopropylate at 230℃; for 6h; Inert atmosphere; Large scale;	97%

citric acid anhydride (24555-16-6) + pentan-1-ol (71-41-0) → tri(n-pentyl) citrate (70289-34-8)

Conditions	Yield
With titanium(IV) isopropylate at 230℃; for 6h; Inert atmosphere;	97%

citric acid anhydride (24555-16-6) + benzylamine (100-46-9) + diazomethyl-trimethyl-silane (18107-18-1) → C13H15NO6 + citric acid mono-benzylamide

Conditions	Yield
Stage #1: citric acid anhydride; benzylamine In acetonitrile at 20℃; for 2h; Stage #2: diazomethyl-trimethyl-silane In methanol; diethyl ether at 20℃; for 0.5h;

citric acid anhydride (24555-16-6) + benzylamine (100-46-9) → C13H15NO6 + citric acid mono-benzylamide

Conditions	Yield
In acetonitrile at 20℃; for 2h;

citric acid anhydride (24555-16-6) + n-octyl β-D-glucopyranoside (29836-26-8) → C20H32O12(2-)*2Na(1+)

Conditions	Yield
Stage #1: citric acid anhydride; n-octyl β-D-glucopyranoside With acetic acid at 90℃; for 2h; Stage #2: With sodium hydroxide In ethanol; water pH=8;	96 %Chromat.

citric acid anhydride (24555-16-6) + n-dodecyl-b-D-glucopyranoside (59122-55-3) → C24H40O12(2-)*2Na(1+)

Conditions	Yield
Stage #1: citric acid anhydride; n-dodecyl-b-D-glucopyranoside With acetic acid at 90℃; for 2h; Stage #2: With sodium hydroxide In ethanol; water pH=8;	95 %Chromat.

citric acid anhydride (24555-16-6) + n-decyl β-D-glucopyranoside (58846-77-8) → C22H36O12(2-)*2Na(1+)

Conditions	Yield
Stage #1: citric acid anhydride; n-decyl β-D-glucopyranoside With acetic acid at 90℃; for 2h; Stage #2: With sodium hydroxide In ethanol; water pH=8;	96 %Chromat.

(3R,3'S,5'R)-3,3'-dihydroxy-β,κ-carotene-6'-one + citric acid anhydride (24555-16-6) → C52H68O15

Conditions	Yield
With pyridine; dmap In dichloromethane at 25 - 40℃; for 5h; Inert atmosphere; Darkness;	2.02 g

citric acid anhydride (24555-16-6) + capsorubin (470-38-2) → C52H68O16

Conditions	Yield
With dmap; triethylamine In dichloromethane at 15 - 40℃; for 5h; Inert atmosphere; Darkness;	1.03 g

citric acid anhydride (24555-16-6) + (3S,3'S)-astaxanthin (472-61-7) → C52H64O16

Conditions	Yield
With dmap; triethylamine In dichloromethane at 15 - 40℃; for 5h; Darkness; Inert atmosphere;	3.28 g

citric acid anhydride (24555-16-6) + zeaxanthin (144-68-3, 3309-19-1, 24502-92-9, 29472-68-2, 31272-50-1, 31272-53-4, 57820-80-1, 60046-54-0, 60497-64-5, 60497-65-6, 72002-36-9, 72580-10-0, 100347-92-0, 100347-97-5, 136656-95-6, 136733-98-7, 136733-99-8, 136734-01-5, 136734-02-6) → C52H68O14

Conditions	Yield
With dmap In dichloromethane at 5 - 40℃; for 5h; Inert atmosphere; Darkness;	2.92 g

citric acid anhydride (24555-16-6) + lutein (127-40-2) → lutein

Conditions	Yield
With dmap; Progesterone; triethylamine In dichloromethane at 15 - 40℃; for 5h; Inert atmosphere; Darkness;	2.37 g

Upstream product

• 77-92-9 citric acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 70289-34-8 tri(n-pentyl) citrate 
• 7147-34-4 tris(2-ethylhexyl)propane-1,2,3-tricarboxylate 
• 16544-70-0 tri-n-hexyl citrate 
• 77-94-1 Citroflex-4 

Relevant articles and documents

Synthesis of Alkyl Monoglucoside Citric Monoester and Properties of Its Sodium Salt

A series of disodium alkyl monoglucoside citric monoesters (AG-EC) were synthesized with an indirect method using glucosides, lauryl/decyl/octyl alcohol and citric acid. The structure and composition of the synthesized surfactants were defined by Fourier transform infrared spectroscopy (FTIR) and liquid chromatography–mass spectrometry (LC/MS). The surface properties, foaming ability and wetting ability were investigated. AG-EC surfactants exhibited excellent water solubility which eliminated the defect of long-chain alkyl glucoside. All three surfactants showed high surface activities. AG12-EC and AG10-EC showed remarkable foaming abilities in distilled water and hard water. Aqueous solutions of AG-EC surfactants spread slowly on a parafilm surface.

Cu-metal-organic framework supported on chitosan for efficient condensation of aromatic aldehydes and malononitrile

In this study, a novel copper-based metal-organic framework (Cu-MOF)-immobilized modified chitosan (CS-CA), CS-CA/Cu-MOF, has been constructed easily and applied as an extremely efficient and economic mesoporous catalyst for the Knoevenagel condensation between aromatic aldehydes with malononitrile under mild reaction conditions. The resultant catalyst is characterized via various techniques including FTIR, XRD, FE-SEM, EDX, TEM, BET and STA analyses. The CS-CA/Cu-MOF was reused eight times without a noteworthy decrease in the catalytic activity. The use of CS-CA/Cu-MOF results in outstanding catalytic activity, high recyclability, very short reaction time at 25 °C, and an easy work-up process for the Knoevenagel condensation.

IMMOBILIZED LIGANDS FOR THE REMOVAL OF METAL IONS AND METHODS THEREOF

Disclosed are immobilized dimercapto succinate compounds (immobilized dithiol compounds), a method to synthesize these immobilized dithiol compounds, and a method of using the immobilized dithiol compounds to remove metals, such as lead, cadmium and mercury from an aqueous solution. Also disclosed are immobilized mono- and tren-citrate compounds (immobilized citrate compounds), a method to synthesize these solid-supported compounds, and a method of using the immobilized citrate compounds to remove trivalent metals, such as iron and aluminum from an aqueous solution.