Green synthesis method for 1,2-bi(trialkyl siloxy) cyclohexene

A trialkylsiloxy, green synthesis technology, applied in the periodic table group 4/14 element compounds, silicon organic compounds, chemical instruments and methods, etc. The problem of high temperature of sodium sand can achieve the effect of obvious raw material cost advantage, environmental friendliness and less dosage

Active Publication Date: 2018-11-23
SHANGYU NHU BIOCHEM IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The above-mentioned synthetic route takes adipic acid or its derivatives as the starting material to have the following defects: the unit consumption of toluene is very large; a large amount of high-risk waste salt (sodium is excessive, containing a small amount of sodium in the waste salt) is produced; sodium sand is beaten in toluene The temperature (≥100°C) is relatively high, and dropping trimethylchlorosilane (bp57.3°C) with a low boiling point, volatile, easy to decompose, and st

Method used

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  • Green synthesis method for 1,2-bi(trialkyl siloxy) cyclohexene
  • Green synthesis method for 1,2-bi(trialkyl siloxy) cyclohexene
  • Green synthesis method for 1,2-bi(trialkyl siloxy) cyclohexene

Examples

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Embodiment 1

[0070] Example 1: Synthesis of 1,2-bis(trimethylsiloxy)cyclohexene

[0071] (1) In a four-neck flask with a reflux device, drop into a toluene azeotrope (containing about 30 wt% of silicon ether) containing hexamethyldisiloxane (silicon ether) (25.0 g in pure form, about 0.1539 mol), and heat up Reflux at 100°C to carry out rectification to divide water, and toluene returns to the system. When anhydrous is distilled, add 15.0 g of concentrated sulfuric acid (concentration 98.5%, about 0.1506 mol) dropwise, continue the reaction to carry out rectification and divide water, and toluene returns to the system middle. After 3 hours of reflux reaction, when anhydrous distilled out, GC detected the reaction solution, and when the silicon ether remained <0.5% (GC apparent content), stop the reaction, cool down to room temperature for standby, and simultaneously calculate the bis(trimethyl Silicon) sulfate concentration is about 37.59wt%, about 0.1491mol.

[0072] (2) In a four-necke...

Embodiment 2～10

[0073] Examples 2-10: Synthesis of 1,2-bis(trimethylsiloxy)cyclohexene

[0074] Examples 2-10 were synthesized with reference to the process of Example 1, and the differences in process conditions are shown in Table 1.

[0075] Table 1: Process conditions and synthesis results of Examples 1 to 10

[0076]

[0077]

Embodiment 11

[0078] Example 11: Synthesis of 1,2-bis(triethylsilyloxy)cyclohexene

[0079] (1) In a four-neck flask with a reflux device, drop into a toluene azeotrope (containing about 38.57 wt% of silicon ether) containing hexaethyldisiloxane (silicon ether) (37.68 g in pure form, about 0.1528 mol), Heat up to 120°C and reflux to carry out rectification of water, and toluene is refluxed in the system. in the system. After 3 hours of reflux reaction, when anhydrous distilled out, GC detected the reaction solution, and when the silyl ether remained <0.5% (GC apparent content), the reaction was stopped, and the temperature was lowered to room temperature for use. At the same time, the concentration of bis(triethylsilyl)sulfate was calculated to be about 44.80 wt%, about 0.1490 mol.

[0080] (2) In a four-necked bottle with a reflux device, put in 6.2g (0.1546mol) of calcium powder and 100g of toluene, and add bis(triethylsilicon)sulfate toluene solution dropwise to control the rate of add...

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Abstract

The invention relates to a green synthesis method for 1,2-bi(trialkyl siloxy) cyclohexene. The method comprises the step of causing 1,2-cyclohexanone, bi(trialkyl silicon) sulphate and reactive metalreact in an inert solvent, thereby acquiring 1,2-bi(trialkyl siloxy) cyclohexene. The bi(trialkyl silicon) sulphate is prepared according to the steps of preparing hexalkyl disiloxane by dehydrating by-product trialkyl silanol in consequent reaction and then continuing to react with concentrated sulfuric acid. The environmental issue of siloxane effluent is completely solved through the recyclingof silicon protecting group; the produced solid waste has a single component and can be prepared into byproduct for sale after simple treatment; the emission of three wastes is less; the technology isenvironment-friendly.

Description

technical field [0001] The invention relates to the field of fine chemicals, in particular to a green synthesis method of 1,2-bis(trialkylsiloxy)cyclohexene. Background technique [0002] 1,2-bis(trialkylsiloxy)cyclohexene is a key intermediate in the synthesis of biotin, and trialkylsiloxy is the oxygen protecting group on the cyclohexane ring. Its structural formula is as (I): [0003] [0004] Among them, R 1 ~R 6 Each independently denoted as C 1 ~C 4 of alkyl. [0005] When R1~R6 in 1,2-bis(trialkylsiloxy)cyclohexene are all methyl groups, 1,2-bis(trimethylsiloxy)cyclohexene has the following preparation method: CN 104592284 A discloses the one-step synthesis of 1,2-bis(trimethylsiloxy)cyclohexene from diethyl adipate, sodium, toluene and trimethylchlorosilane. (1971, P236-253) basically the same synthetic method. Although the yield of CN104592284 A reaches 83%, which has industrial significance, the amount of trimethylchlorosilane needed for the synthesis of...

Claims

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Application Information

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IPC IPC(8): C07F7/18C07F7/08
CPCC07F7/0834C07F7/188Y02P20/55
Inventor 刘祥洪吕国锋田金金乔胜超杭姣陈凯
Owner SHANGYU NHU BIOCHEM IND
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