13039-42-4

Upstream product

• 112-61-8 Methyl stearate 
• 57-50-1 Sucrose 
• 135363-34-7 3-stearoyl-5-methyl-1,3,4-thiadiazole-2(3H)-thione 
• 65439-62-5 3-stearoylthiazolidine-2-thione 
• 112-76-5 Stearoyl chloride 
• 638-08-4 stearic anhydride 
• 57-11-4 stearic acid 

Relevant academic research and scientific papers

Self-organizing properties of monosubstituted sucrose fatty acid esters: The effects of chain length and unsaturation

Three families of mono-substituted sucrose fatty acid esters were prepared by enzymatic and classical synthetic procedures, and their self-assembly and self-organizational properties were investigated by thermal polarised light microscopy, differential scanning calorimetry and X-ray diffraction. The properties were evaluated as a function of the fatty acid chain length. For the lower homologues of the series columnar liquid-crystalline stacking structures were found, whereas for the higher homologues, lamellar phases predominated. A model for the columnar stacking arrangement, consisting of a unique arrangement of the molecules which could lead to the creation of multiple internal ion channels between the hydrophobic interior and the hydrophilic exterior of the columns, is suggested.

Efficient Solvent-Free Synthesis of Sucrose Esters via Sand-Milling Pretreatment on Solid–Liquid Mixtures

A general and efficient method, involving sand-milling pretreatment and base-catalyzed transesterification of sucrose and fatty acid methyl ester (FAME), was presented for the solvent-free synthesis of sucrose esters. A metastable homogeneous paste with a solid particle size of 13 μm (D50) was obtained by milling at 1000 rpm for 1 h. This reaction mixture generated a total SE yield of 88.2% with a methyl stearate (MS) conversion of 91.4% using K2CO3 as a catalyst at 135?°C for 3 h at a stirring rate of 500 rpm, while those without milling (D50, 153 μm) yielded a total sucrose fatty acid esters (SE) of 49.3% with a MS conversion of 83.1% under the same reaction conditions. The reaction kinetics revealed that the reaction mixture with milling pretreatment displays a shorter induction time and a faster reaction rate for the formation of SE. The promotion of the solvent-free synthesis of SE in the current study could be attributed to the reduction of solid particle sizes and the increased compatibility of solid–liquid phases. We believe that this strategy could be used as a general way for strengthening other heterogeneous reactions in the organic synthesis.

A sucrose fatty acid ester preparation method and its milk beverage composition

The invention provides a preparation method of sucrose fatty acid ester. The preparation method comprises the following steps: A) performing a reflux reaction of sucrose and alkyl ester in the presence of an alkali catalyst in a solvent mixture to produce a product mixture; B) adding a saturated sodium chloride solution to the product mixture, adjusting pH to 6.6-7.2, adding an alcohols extractant for extraction, and performing liquid separation to obtain an organic phase; and C) performing reduced-pressure concentration and evaporation to dryness to obtain sucrose fatty acid ester. The invention belongs to the technical field of industrial chemistry and provides the preparation method which is simple in steps and mild in reaction condition. High-purity low-substitution-degree sucrose fatty acid ester is prepared through the method and is good in performance. The environmental benefit is good.

Regioselective formation of 6-O-acylsucroses and 6,3′-di-O-acylsucroses via the stannylene acetal method

Regioselective formation of 6-O-acylsucroses and 6,3′-di-O-acylsucroses in one pot with good yields was achieved for the first time by a typical acylation method of sucrose via its dibutylstannylene acetal. Pure monoesters at OH-6 and diesters at OH-6,3′ obtained by these procedures were readily isolated by simple column chromatography, thus overcoming the main difficulties associated with regioselectivity, efficiency, and isolation techniques for the practical preparation. Explanations for the regioselectivities observed during this stannylene acetal-mediated reaction were also proposed based on the structures of the stannylene acetal in solution and the intramolecular migration of stannylenes.

Shape dependence in the formation of condensed phases exhibited by disubstituted sucrose esters

We report on the self-organizing properties of sucrose esters that are di-(1′,6′, 1′,6, and 6,6′)-substituted with aliphatic chains of identical or different chain lengths and levels of saturation. For the materials possessing two saturated aliphatic chains, the compounds exhibited thermotropic lamellar smectic A phases. A remarkable new phase transition was observed for the di-octadecanoyl homologue in which one smectic A phase transformed into another with a continuous change in layer spacing, but with a discontinuous change in the correlation length. The incorporation of long cis-unsaturated chains led to increased cross-sectional areas of the chains relative to the sucrose head groups and, hence, columnar phases were observed.

Sucrose esterification under Mitsunobu conditions: Evidence for the formation of 6-O-acyl-3′,6′-anhydrosucrose besides mono and diesters of fatty acids

A series of sucrose monoesters and homogeneous or mixed diesters, which have various chain lengths and saturation levels, were prepared under Mitsunobu conditions with good regioselectivity. Among the anhydro derivatives arising from competitive intramolecular etherification, 3′,6′-anhydrosucrose 6-O-monoesters, which have never been reported, were identified.

Transesterification of Sucrose in Organic Medium: Study of Acyl Group Migrations

The tendency of the acyl groups located on the glucose part of sucrose fatty acid esters to undergo intramolecular migrations in organic medium and the regioselectivity of some transesterifications of sucrose were investigated by HPLC, in situ NMR spectroscopy and preparative methods. Extensive acylation on secondary positions of the glucose moiety followed by migrations is general for base catalysed transesterification. The stability of 3- and 6-O-acyl derivatives, two isomers being thermodynamically favored compared to others, was studied in a series of conditions. It is shown that the presence of water catalyzes the migration of the ester at OH-3 towards OH-6 in organic basic medium, whereas the ester at OH-6 appears more stable under either acidic or basic conditions.

Regioselective synthesis of sucrose monoesters as surfactants

A highly regioselective conversion of sucrose into 6-O-acyl derivatives is reported. First sucrose was transformed into the dibutyltin acetal, thus enhancing the nucleophilicity at the C-6 oxygen and restricting the subsequent acylation reaction. The surface activity properties of the sucrose monoesters obtained were determined and compared with those of commercially available ionic and non-ionic surfactants.

A new synthesis of 6-O-acylsucroses and of mixed 6,6'-di-O-acylsucroses

Various 6-O-acylsucroses were synthesized in good yields from unprotected sucrose in N,N-dimethylformamide and the appropriate 3-acylthiazolidine-2-thiones 6 or 3-acyl-5-methyl-1,3,4-thiadiazole-2(3H)-thiones 7.A selective ionization of the free sugar by

A new chemoenzymatic synthesis of 6'-O-acylsucroses

6'-O-acylsucroses were synthesized for the first time in two steps, including a new chemical selective acylation of free sucrose followed by an enzymatic hydrolysis of the 6-O-acylated by-products.