22651-87-2

Basic information

• Product Name: cyclohexanecarboxylic anhydride
• Synonyms: cyclohexanecarboxylic anhydride;Bis(cyclohexanecarboxylic)anhydride;Einecs 245-146-8
• CAS NO: 22651-87-2
• Molecular Formula: C₁₄H₂₂O₃
• Molecular Weight: 238.32268
• EINECS: 245-146-8
• Mol File: 22651-87-2.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 156°C/0.7mmHg(lit.)
• Flash Point: 161.2°C
• Appearance: /
• Density: 1.082g/cm³
• Vapor Pressure: 2.82E-05mmHg at 25°C
• Refractive Index: 1.4740-1.4780
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: cyclohexanecarboxylic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: cyclohexanecarboxylic anhydride(22651-87-2)
• EPA Substance Registry System: cyclohexanecarboxylic anhydride(22651-87-2)

Safety Data

• Hazardous Substances Data: 22651-87-2(Hazardous Substances Data)

Usage

Description

Cyclohexanecarboxylic anhydride, also known as hexahydrophthalic anhydride, is a cyclic anhydride of cyclohexanecarboxylic acid. It is a colorless to light yellow liquid with a pungent odor and is recognized for its versatile applications across various industries.

Uses

Used in Chemical Production:
Cyclohexanecarboxylic anhydride is used as a key intermediate for the production of various chemicals, including agricultural chemicals and pharmaceuticals, due to its reactive nature and ability to form stable derivatives.
Used in Epoxy Resin Industry:
Cyclohexanecarboxylic anhydride is used as a curing agent for epoxy resins, enhancing their hardness and thermal stability, which is crucial for applications in coatings, adhesives, and composite materials.
Used in Plasticizer Industry:
It serves as a raw material in the production of plasticizers, which are additives that increase the flexibility and workability of plastics, making them suitable for a wide range of applications in the manufacturing of consumer goods and industrial products.
Used in Alkyd Resin Industry:
Cyclohexanecarboxylic anhydride is used as a component in alkyd resins, contributing to their properties such as adhesion, gloss, and chemical resistance, which are essential for use in paints and surface coatings.
Used in Manufacturing of Curing Agents:
As a hardener in the production of curing agents for epoxy resins, cyclohexanecarboxylic anhydride plays a critical role in the final properties of the cured epoxy systems, ensuring their performance in demanding environments.
It is important to handle cyclohexanecarboxylic anhydride with care due to its potential irritant and harmful effects on human health and the environment, highlighting the need for proper safety measures during its use and production.

InChI:InChI=1/C14H22O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h11-12H,1-10H2

Upstream product

• 65-85-0 benzoic acid 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 2043-61-0 cyclohexanecarbaldehyde 
• 535-80-8 3-chlorobenzoate 
• 98-89-5 Cyclohexanecarboxylic acid 
• 122-97-4 3-Phenyl-1-propanol 
• 60-12-8 2-phenylethanol 
• 100-51-6 benzyl alcohol 
• 100-49-2 cyclohexylmethyl alcohol 
• 108-24-7 acetic anhydride 
• 54829-34-4 Cyclohexanecarbothioic acid S-propyl ester 
• 54829-35-5 Cyclohexanecarbothioic acid S-isopropyl ester 
• 136-01-6 cyclohexanecarboxylic acid Na-salt 

Downstream Products

• 1565-74-8 (R)-1-phenyl-1-propanol 
• 613-87-6 (S)-1-phenyl-1-propanol 
• 150614-90-7 (dimethyl(phenyl)silyl)(cyclohexyl)methanone 
• 57794-08-8 (1S,2S)-trans-1,2-Cyclohexanediol 
• 1072-86-2 (1R,2R)-trans-1,2-cyclohexanediol 
• 1448438-60-5 C₁₃H₂₂O₃ 
• 1297270-24-6 3-cyclohexyl-4,5-diphenyl-4H-[1,2,4]triazole 
• 1329472-32-3 4-(4-bromophenyl)-3-cyclohexyl-5-phenyl-4H-[1,2,4]triazole 
• 59293-37-7 tetrahydro-1-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-cyclohexylcarbonyloxy-2(1H)-pyrimidinone 
• 89205-23-2 2-Cyclohexyl-5-(3,4,5-trimethoxy-phenyl)-oxazole-4-carboxylic acid amide 

Relevant articles and documents

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PPh3/Selectfluor-Mediated Transformation of Carboxylic Acids into Acid Anhydrides and Acyl Fluorides and Its Application in Amide and Ester Synthesis

By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can selectively react with a second carboxylic acid or fluoride to in situ yield the corresponding acid anhydrides or acyl fluorides. The developed protocol features commercially availabile reagents, no involvement of base, room temperature conditions, and simple experimental procedure. Additionally, various amides or esters are readily achieved, respectively, with the addition of amines or alcohols.

Nickel-Catalyzed Decarboxylative Alkenylation of Anhydrides with Vinyl Triflates or Halides

Decarboxylative cross-coupling of aliphatic acid anhydrides with vinyl triflates or halides was accomplished via nickel catalysis. This methodology works well with a broad array of substrates and features abundant functional group tolerance. Notably, our approach addresses the issue of safe and environmental installation of methyl or ethyl group into molecular scaffolds. The method possesses high chemoselectivity toward alkyl groups when aliphatic/aromatic mixed anhydrides are involved. Furthermore, diverse ketones could be modified with our strategy.