63648-81-7Relevant academic research and scientific papers
Tin(IV)-functionalised polymer supports; non-toxic and practical reagents for regioselective acetylation of sucrose
Macindoe, Wallace M.,Williams, Andrew,Khan, Riaz
, p. 17 - 25 (1996)
Polymer-supported butyltin(IV) reagents have been surveyed for regioselectivity in acetylation of sucrose. Polymer-supported butyltin(IV) dichloride 8 catalysed the acetylation of sucrose to give a 59% yield of 6-O-acetyl sucrose 3, the precursor of sucralose. The yield is close to that of a previously reported process involving dibutyltin(IV) oxide (Bu2SnO). The spent polymeric resin could readily be regenerated and can be subsequently used in further synthetic reactions.
Monotin organic compound, preparation method and application thereof
-
Paragraph 0101-0112, (2021/05/08)
The invention provides a single tin organic compound which is used for synthesizing sucrose-6-carboxylic ester, and the compound is a compound represented by the following formula (1), R , R and R respectively and independently represent straight-chain or branched-chain saturated alkyl groups of C1-C8, straight-chain or branched-chain unsaturated alkyl groups of C2-C8, substituted or unsubstituted saturated cycloalkyl groups of C3-C8, substituted or unsubstituted unsaturated cycloalkyl groups of C3-C8, or aryl groups or substituted aryl groups of C6-C12; and R4 represents a straight chain or branched chain saturated alkyl group of C1 to C6 or an aryl group or a substituted aryl group of C6 to C12. According to the single-tin organic compound, in the process of synthesizing sucrose-6-carboxylic ester, metering and feeding can be accurately carried out, meanwhile, the recovery rate of a catalyst is increased, follow-up chlorination side reactions are reduced, the reaction is fast, energy consumption is small, and the yield in unit volume is higher.
Sucrose-6-ester production equipment and production method
-
Paragraph 0084-0093, (2021/05/29)
The invention provides sucrose-6-ester production equipment and a production method. The equipment comprises a shell, a film scraping device and a base, the film scraping device is arranged on the base, and the shell covers the outer sides of the film scraping device and the base; the shell is provided with a reaction liquid feeding hole and a condensed water outlet; the base is provided with a carboxylic ester feeding pipe, a reaction product discharging pipe and a reaction channel connected with the carboxylic ester feeding pipe; the film scraping device comprises a temperature control device, a rotating pipe and a plurality of scraping pieces arranged on the inner wall of the rotating pipe, and the outer edges of the scraping pieces abut against the outer wall of the temperature control device. The rotating pipe can rotate around the temperature control device, so that the scraper blade can scrape reaction liquid which enters from the reaction liquid feeding hole and flows down along the outer wall of the temperature control device into a liquid film on the outer wall of the temperature control device, and the liquid film is separated into evaporation residual liquid and water vapor. According to the invention, the integrated design of a separation device and a reaction device is realized, the volume of production equipment is reduced, the occupied area is saved, the yield of sucrose-6-ester is improved, and the production cost is greatly saved.
Preparation method of sucrose-6-acetate
-
Paragraph 0009-0013, (2019/04/17)
The invention relates to a synthesis method of sucrose-6-acetate. The synthesis method comprises the following steps: (1) adding sucrose into an organic solvent DMF (Dimethyl Formamide), heating to 80to 85 DEG C for dissolving, then cooling to 75 DEG C, adding an alkaline solvent and an organic tin compound, and refluxing and reacting with water for 5 to 8 hours, wherein the reflux temperature iscontrolled to be 70 to 75 DEG C; (2) cooling a reactant to -10 DEG C or below, dropwise adding acetic anhydride in the reactant under a stirring condition, and reacting for 3 hours; (3) adding an appropriate amount of water in a reaction solution, extracting the organic tin compound by using a non-polar organic solvent, recycling and reusing after concentrating, and carrying out vacuum distillation on a residual extracted solution for removing the organic solvent, thus obtaining a sucrose-6-acetate solution. A preparation method disclosed by the invention has the following advantages that through the technology disclosed by the invention, the reaction time is reduced, generation of side reaction is reduced, the cost is low, the energy consumption is reduced, and the yield of the sucrose-6-acetate is up to 91 percent.
Recrystallization method of sucrose-6-acetate and applications thereof
-
Paragraph 0027-0029; 0051, (2017/09/01)
The invention discloses a recrystallization method of sucrose-6-acetate, and applications thereof. The recrystallization method comprise following steps: a solvent is added into a sucrose-6-acetate mixture obtained via sucrose esterification; and stirring, dissolving, filtering, and drying are carried out so as to obtain sucrose-6-acetate, wherein the solvent is a mixture of a nitrile solvent and an ether solvent. The recrystallization method is capable of increasing sucrose-6-acetate purity, and reducing adverse influences on subsequent chlorination.
Sucrose-6-acetate synthesis method
-
Paragraph 0026; 0027, (2017/03/14)
The invention discloses a synthesis method of sugar cane-6-acetic acid ester. The synthesis method of the sugar cane-6-acetic acid ester comprises the following steps: in a mixed solvent of water and dimethyl formamide, mixing and dissolving sugar cane and an acid-binding agent at the temperature of 0-5 DEG C; dropwise adding a dimethyl formamide solution of acetic anhydride at 0-5 DEG C under a stirring condition, and reacting for 4-6 hours; after the reaction is finished, carrying out reduced pressure distillation for removing the water and dimethyl formamide solvents, adding a mixed solvent of acetone and methyl alcohol, recrystallizing, filtering, washing and drying, thus obtaining the sugar cane-6-acetic acid ester product. The synthesis method of the sugar cane-6-acetic acid ester has the advantages that acetic anhydride is used for doing sugar cane-6 hydroxyl in a new reaction system, so that an expensive and toxic reagent is not used, cost is low, and environmental friendliness is realized; reaction is carried out at a low temperature, so that product quality and yield can be improved, and the yield can be 72-85%.
A one-pot synthesis of synthetic trichloro-6-acetate method
-
Paragraph 0040; 0043; 0044, (2017/02/09)
The invention discloses a method for synthesizing sucralose-6-acetate by using a one-pot method. The method comprises the following steps of: adding saccharose, trimethyl orthoacetate and a sulfonated bamboo charcoal catalyst in a reaction vessel to carry out hydroxyl protection reaction on the C-6 position of the saccharose, after the reaction is ended completely, adding a phthalate-based cationic dimeric surfactant as shown in the formula (I) to carry out a chlorination reaction, after the reaction is ended, extracting by using ethyl acetate, decoloring by using active carbon, concentrating and crystallizing to obtain a sucralose-6-acetate product, wherein R in the formula (I) is alkyl, allyl or benzyl from C1 to C10. The method has the characteristics of simplicity in process operation, good technical performance, few three wastes, convenience for aftertreatment and recyclable reaction system so as to be an economical and practical environment friendly technology.
Probing substrate promiscuity of amylosucrase from neisseria polysaccharea
Daude, David,Champion, Elise,Morel, Sandrine,Guieysse, David,Remaud-Simeon, Magali,Andre, Isabelle
, p. 2288 - 2295 (2013/08/23)
The amylosucrase from Neisseria polysaccharea (NpAS) naturally catalyzes the synthesis of a variety of products from sucrose and shows signs of plasticity of its active site. To explore further this promiscuity, the tolerance of amylosucrase towards different donor and acceptor substrates was investigated. The selection of alternate donor substrates was first made on the basis of preliminary molecular modeling studies. From 11 potential donors harboring selective derivatizations that were experimentally evaluated, only p-nitrophenyl-α-D-glucopyranoside was used by the wild-type enzyme, and this underlines the high specificity of the -1 subsite of NpAS for glucosyl donor substrates. The acceptor substrate promiscuity was further explored by screening 20 hydroxylated molecules, including D- and L-monosaccharides as well as polyols. With the exception of one compound, all were successfully glucosylated, and this showcases the tremendous plasticity of the +1 subsite of NpAS, which is responsible for acceptor recognition. The products obtained from the transglucosylation reactions of three selected acceptors were characterized, and they revealed original structures and enzyme enantiopreference, which were more particularly analyzed by insilico docking analyses.
Low Temperature, Single Solvent Process for the Production of Sucrose-6-Ester
-
Page/Page column 8, (2011/04/25)
A method for the preparation of a sucrose-6-ester is disclosed. In a first step of the method, sucrose in a polar aprotic solvent is reacted with an organotin-based acylation promoter. The water of reaction is removed at a temperature that does not exceed about 80° C. In one aspect, the water is removed by distillation of part of the polar aprotic solvent at reduced pressure. In a second step, a carboxylic acid anhydride is added. In one aspect, the resulting reaction mixture is maintained at a temperature of 10° C. or less for a period of time sufficient to produce a sucrose-6-ester. The sucrose-6-ester can be converted to sucralose.
Process for the production of sucrose-6-ester
-
Page/Page column 9, (2011/04/25)
A process for the production of sucrose-6-ester is disclosed. The process includes, in order, the steps of: (a) providing a first reaction mixture including sucrose, a reaction vehicle, and an organotin-based acylation promoter;(b) removing water from the first reaction mixture to afford a second reaction mixture that is substantially free from water; and(c) adding a carboxylic acid anhydride to the second reaction mixture to afford a third reaction mixture, thereby producing a sucrose-6-ester;wherein:during step (b), the removing of water includes distillation of water with the reaction vehicle using an apparatus supplying a heat flux of from 500 to 25,000 BTU/hrft2 (1577 to 78865 W/m2) selected from the group consisting of wiped film evaporators, agitated thin film evaporators, falling film evaporators and rising film evaporators.
