Unlock instant, AI-driven research and patent intelligence for your innovation.

D-glucaro-6,3-lactone monoester and a process for the preparation thereof

A technology of glucaric acid, -C3-C10, applied in the field of preparation of it, can solve the problems of unsuitable yield and selectivity feasible technology, low yield and purity of the final product, unsatisfactory, etc.

Pending Publication Date: 2020-12-04
BASF SE
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A disadvantage in the preparation of D-glucaro-6,3-lactone monoester is the formation of the diester as one of the by-products
The prior art for selectively obtaining D-glucaro-6,3-lactone monoester is unsatisfactory due to the low yield and purity of the final product
Furthermore, the relatively high yields and selectivities of undesired products such as diesters and acids make feasible techniques unsuitable

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • D-glucaro-6,3-lactone monoester and a process for the preparation thereof
  • D-glucaro-6,3-lactone monoester and a process for the preparation thereof
  • D-glucaro-6,3-lactone monoester and a process for the preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0473] 1. A method for preparing D-glucaric acid-6,3-lactone monoester, comprising the following steps:

[0474] (A) make D-glucaric acid-6,3-lactone and at least one alcohol of general formula (I) in at least one inorganic acid or at least one Lewis acid or at least one carboxylic acid or at least one The reaction in the presence of sulfonic acid:

[0475] R 1 -OH (I),

[0476] in

[0477] R 1 Indicates unsubstituted linear or branched C 1 -C 20 alkyl, or

[0478] Unsubstituted linear or branched C 2 -C 20 alkenyl, or

[0479] Unsubstituted or branched C 3 -C 10 Cycloalkyl, or

[0480] Unsubstituted or branched C 3 -C 10 cycloalkenyl, or

[0481] unsubstituted C 1 -C 10 Alkylene-C 3 -C 10 Cycloalkyl, or

[0482] unsubstituted C 1 -C 10 Alkylene-C 3 -C 10 cycloalkenyl, or

[0483] -(CH 2 CH 2 O) n H, where n is an integer from 1 to 20, or

[0484] -(CH 2 ) n YR 2 ,

[0485] Where n is an integer of 1-20,

[0486] Y means O or S; and

[0487] ...

Embodiment

[0595] The following chemicals were purchased from Sigma Aldrich:

[0596] D-glucaro-6,3-lactone

[0597] Alcohols of general formula (I): decyl alcohol, dodecanol, myristyl alcohol, octanol and cetyl alcohol

[0598] Polar aprotic solvents: 2 alkyl

[0599] Acid Catalyst: Aluminum Methanesulfonate

[0600] Molecular sieve

[0601] General procedure for the synthesis of D-glucaro-6,3-lactone monoester:

[0602] D-glucaric acid-6,3-monolactone (96.1% purity, 0.65mol, 131g), alcohol (1.0 equivalent, 0.65mol), aluminum methanesulfonate (0.1 equivalent, 0.065mol, 20.4g), optionally molecular sieve and two Alkanes (360 g) were added to the reaction flask. The mixture was stirred at 50-80°C until the reaction was complete. The reaction mass was added to 200 mL of 5% aqueous sodium bicarbonate and the organic layer was separated. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated to give a crude product. The crude product is...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

Presently claimed invention relates to D-glucaro-6, 3-lactone monoester products and a process for the preparation of the same by reaction of D-glucaro-6, 3-lactone with at least one alcohol in the presence of at least one mineral acid or at least one Lewis acid or at least one carboxylic acid or at least one sulfonic acid.

Description

[0001] field of invention [0002] The present invention relates to a monoesterification product obtained from D-glucaro-6,3-lactone and alcohol and a method for preparing it. [0003] Background of the invention [0004] Glucaric acid is obtained by oxidizing sugars such as glucose with nitric acid. The sodium salt of glucaric acid is used in dishwasher detergents. The sodium salt of glucaric acid acts as a chelating agent for calcium and magnesium ions in hard water to make the detergent more effective. The use of the sodium salt of glucaric acid has replaced the environmentally problematic phosphate in most detergents. [0005] Glucaric acid forms two lactone isomers—(1,4) and (3,6)D-glucarolactone. D-glucaric acid-6,3-lactone acid has excellent stability in aqueous solution and will not be hydrolyzed to the corresponding dibasic acid. [0006] [0007] Ethyl, propyl, butyl and pentyl monoesters of D-glucaric acid were synthesized by Zinner et al. [Chem Ber 1956, 1503...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33
CPCC07D307/33
Inventor D·奥尔曼A·罗伊B·蒂斯伯格T·鲍德斯坦R·穆莱
Owner BASF SE