Method for preparing 1,3-glycol monoether compound

A technology of diol monoethers and compounds, which is applied in the direction of ester reaction to prepare ethers, ether preparations, organic chemistry, etc., can solve the problems of cumbersome operation, hidden safety hazards, and expensive halogenated alkanes, and achieves mild reaction conditions, easy separation and purification, The effect of reducing production costs

Active Publication Date: 2010-05-12
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Prepare 1 with said method, there are following problems in 3-diol monoether compound: the first, reaction is carried out in non-aqueous organic polar solvent, all reactants will be carried out drying process before reaction, because various Different materials have different drying methods, so the operation is more cumbersome
Second, 1,3-diol reacts violently with sodium or sodium hydride, which is difficult to control, and at the same time generates flammable and explosive hydrogen, which has potential safety hazards; third, many halogenated alkanes are expensive, resulting in increased product costs; fourth, A large amount of polar solvent is used, which not only reduces the production efficiency, but also increases the burden and cost of recycling
The problem that this method exists is that yield is low, and the yield of some products is only 15%
The composition of the product of this method is complex and difficult to purify

Method used

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  • Method for preparing 1,3-glycol monoether compound
  • Method for preparing 1,3-glycol monoether compound
  • Method for preparing 1,3-glycol monoether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 2, the preparation of 2-dimethyl-3-methoxy-1-propanol

[0051] Under stirring, 10.4 g of 2,2-dimethyl-1,3-propanediol, 7.2 g of sodium hydroxide, 0.5 g of benzyltrimethylammonium chloride and 16.8 g of water were uniformly mixed, and the temperature was raised to 90°C. 18.9 g of dimethyl sulfate was added dropwise, and reacted at 90° C. for 3 hours after the drop was completed. The product was cooled, and the oil layer was separated, and the water layer was taken with dichloromethane benzene and combined with the oil layer. The dichloromethane was distilled off, distilled under reduced pressure, and the 58-75°C / 15mmHg fraction was collected to obtain 7.8 g of colorless and transparent 2,2-dimethyl-3-methoxy-1-propanol with a yield of 66%.

[0052] 1H NMR (CDCl3 / TMS) δ (ppm): 0.92 (s, 6H, CH3), 2.65 (t, 1H, OH), 3.24 (s, 2H, CH2), 3.34 (s, 3H, CH3), 3.44 ( s, 2H, CH2).

Embodiment 2

[0053] Example 2 2, the preparation of 2-dimethyl-3-ethoxyl-1-propanol

[0054] Under stirring, 5.2g of 2,2-dimethyl-1,3-propanediol, 3g of sodium hydroxide, 0.3g of benzyltriethylammonium chloride and 7.0g of water were uniformly mixed, and the temperature was raised to 60°C. 11.6 g of diethyl sulfate was added dropwise, and reacted at 60° C. for 5 hours after the drop was completed. The product was cooled, and the oil layer was separated, and the water layer was extracted with ether and combined with the oil layer. Distill off ether, distill under reduced pressure, collect fractions at 70-80°C / 15mmHg to obtain 4.2 g of colorless and transparent 2,2-dimethyl-3-ethoxy-1-propanol with a yield of 64%.

[0055] 1H NMR (CDCl3 / TMS) δ (ppm): 0.92 (s, 6H, CH3), 1.19 (t, 3H, CH3), 2.98 (t, 1H, OH), 3.29 (s, 2H, CH2), 3.44- 3.51 (m, 4H, CH2).

Embodiment 3

[0056] Example 3 Preparation of 2,2-diisobutyl-3-methoxy-1-propanol

[0057] Under stirring, 1.9g 2,2-diisobutyl-1,3-propanediol, 0.6g sodium hydroxide, 0.1g benzyltriethylammonium chloride, 1.4g water and 10ml benzene were mixed uniformly, and the temperature was raised to 60°C. 1.9 g of dimethyl sulfate was added dropwise and reacted at 60° C. for 5 hours after the drop was completed. Cool the product, separate the oil layer, evaporate the benzo and distill under reduced pressure, collect fractions at 120-125°C / 140Pa to obtain colorless and transparent 2,2-diisobutyl-3-methoxy-1-propanol 1.4 g, yield 69%.

[0058] 1H NMR (CDCl3 / TMS) δ(ppm): 0.91~0.95(m, 12H, CH3), 1.28(d, 4H, CH2), 1.66-1.72(m, 2H, CH), 2.79(t, 1H, OH ), 3.32 (S, 3H, CH3), 3.33 (S, 2H, CH2), 3.53 (d, 2H, CH2).

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Abstract

The invention relates to a simple, safe and economic method for preparing the compound of 1,3-diol single ether with general formula(I), including: making 1,3-diol with general formula(II) react withsulfate under the conditions of alkalinity, water or water / oil two-phase, existing or not existing the phase transfer catalyst, to prepare the compound of 1,3-diol single ether. In general formula (I) and (II), R1-R6 being same or different are selected from hydrogen, halogens, C1-C20 alkyl of linear or branched chain, C3-C20 cyclane , C6-C20 aryl, C7-C20 alkaryl and C7-C20 aralkyl, and two or more R1-R6 groups can link to generate saturated or unsaturated ring structure, which can be replaced with the group with the same definition of R1-R6. R7 is selected from C1-C20 alkyl of linear or branched chain, C3-C20 cyclane, C6-C20 aryl, C7-C20 alkaryl and C7-C20 aralkyl.

Description

technical field [0001] The invention relates to a method for preparing 1,3-diol monoether compounds. Background technique [0002] It is currently known that 1,3-diol monoether compounds can be used to synthesize a variety of esters, silicon ethers and thioether compounds. These compounds can be used as electron donor components of olefin polymerization catalysts and used in propylene polymerization reactions. , can obtain better hydrogen adjustment sensitivity, and improve the yield and isotacticity of the polymer (CN1446787A, CN 1480453A, CN 1490340A, CN 1542014A, US 6,822,109). [0003] The Williamson reaction is an important method for the synthesis of ethers. This method is to react alcohols with metal sodium or sodium hydride to produce sodium alkoxides, and react with halogenated hydrocarbons to generate corresponding ethers (Furniss B S, Hannaford AJ, Smith P W G, Tatchell A R . Vogel's Textbook of Practical Organic Chemistry, 5th ed, Addison Wesley Longman Limited,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/16C07C43/02
Inventor 赵思源谢伦嘉孙竹芳柯丽冯静张明森李天益
Owner CHINA PETROLEUM & CHEM CORP
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