18470-76-3

Usage

Uses

Used in Chemical Synthesis:
N-Decylsuccinic anhydride is used as a building block for the synthesis of various chemical products, such as surfactants, emulsifiers, and corrosion inhibitors. Its unique structure allows it to be a key component in creating these compounds.
Used in Industrial Applications:
In the industrial sector, N-Decylsuccinic anhydride is utilized in the production of cosmetic ingredients and pharmaceutical intermediates. Its surface-active properties make it suitable for these applications, enhancing the performance of the final products.
Used in Lubricant and Plasticizer Production:
N-DECYLSUCCINIC ANHYDRIDE also serves as a raw material in the manufacture of lubricants and plasticizers, where its chemical structure contributes to the desired properties of these materials.
Used as a Reagent in Organic Synthesis:
N-Decylsuccinic anhydride may be employed as a reagent in organic synthesis, facilitating various chemical reactions that lead to the formation of new compounds.
Used as a Crosslinking Agent in Polymer Formulation:
Furthermore, it can be used as a crosslinking agent in the formulation of polymers, where it helps to create a network structure that enhances the polymer's properties.

InChI:InChI=1/C14H24O3/c1-2-3-4-5-6-7-8-9-10-12-11-13(15)17-14(12)16/h12H,2-11H2,1H3

Upstream product

• 5077-84-9 dodecane-1,1,2-tricarboxylic acid 
• 201230-82-2 carbon monoxide 
• 51758-19-1 β-tridecanolactone 
• 2855-19-8 Decyl-oxiran 

Downstream Products

• 2530-33-8 Decylsuccinic acid 
• 68386-65-2 2-[(2,4-Dichloro-phenylcarbamoyl)-methyl]-dodecanoic acid 
• 68386-67-4 2-(p-Tolylcarbamoyl-methyl)-dodecanoic acid 
• 68386-64-1 2-[(4-Chloro-phenylcarbamoyl)-methyl]-dodecanoic acid 
• 68386-68-5 2-[(4-Methoxy-phenylcarbamoyl)-methyl]-dodecanoic acid 
• 68386-63-0 2-Phenylcarbamoylmethyl-dodecanoic acid 
• 87458-73-9 decylbutanediperoxoic acid 

Relevant academic research and scientific papers

Succinic anhydrides from epoxides

Catalysts and methods for the double carbonylation of epoxides are disclosed. Each epoxide molecule reacts with two molecules of carbon monoxide to produce a succinic anhydride. The reaction is facilitated by catalysts combining a Lewis acidic species with a transition metal carbonyl complex. The double carbonylation is achieved in single process by using reaction conditions under which both carbonylation reactions occur without the necessity of isolating or purifying the product of the first carbonylation.

Catalytic double carbonylation of epoxides to succinic anhydrides: Catalyst discovery, reaction scope, and mechanism

The first catalytic method for the efficient conversion of epoxides to succinic anhydrides via one-pot double carbonylation is reported. This reaction occurs in two stages: first, the epoxide is carbonylated to a β-lactone, and then the β-lactone is subsequently carbonylated to a succinic anhydride. This reaction is made possible by the bimetallic catalyst [(CITPP)Al(THF)2]+[Co(CO)4]- (1; CITPP = meso-tetra(4-chlorophenyl)porphyrinato; THF = tetrahydrofuran), which is highly active and selective for both epoxide and lactone carbonylation, and by the identification of a solvent that facilitates both stages. The catalysis is compatible with substituted epoxides having aliphatic, aromatic, alkene, ether, ester, alcohol, nitrile, and amide functional groups. Disubstituted and enantiomerically pure anhydrides are synthesized from epoxides with excellent retention of stereochemical purity. The mechanism of epoxide double carbonylation with 1 was investigated by in situ IR spectroscopy, which reveals that the two carbonylation stages are sequential and non-overlapping, such that epoxide carbonylation goes to completion before any of the intermediate β-lactone is consumed. The rates of both epoxide and lactone carbonylation are independent of carbon monoxide pressure and are first-order in the concentration of 1. The stages differ in that the rate of epoxide carbonylation is independent of substrate concentration and first-order in donor solvent, whereas the rate of lactone carbonylation is first-order in lactone and inversely dependent on the concentration of donor solvent. The opposite solvent effects and substrate order for these two stages are rationalized in terms of different resting states and rate-determining steps for each carbonylation reaction.

Catalytic carbonylation of β-lactones to succinic anhydrides

A well-defined,highly active and selective catalyst for the synthesis of succinic anhydrides from CO and β-lactones is reported. At 200 psi of CO, the catalyst [(N,N′-bis(3,5-di-tert-butylsalicylidene)phenylenediamino)Al(THF)2][Co(CO)4] carbonylates β-propiolactones to succinic anhydrides in high yield. (R)-β-Butyrolactone is carbonylated to (S)-methylsuccinic anhydride with clean inversion of stereochemistry, while cis-2,3-dimethyl-β-propiolactone yields exclusively trans-2,3-dimethylsuccinic anhydride. These data are consistent with a mechanism involving nucleophilic attack by [Co(CO)4]- on the β carbon of the lactone, followed by CO insertion and anhydride formation. Copyright