CN104926850A - Iodotrimethylsilane preparation method - Google Patents
Iodotrimethylsilane preparation method Download PDFInfo
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- CN104926850A CN104926850A CN201510421040.8A CN201510421040A CN104926850A CN 104926850 A CN104926850 A CN 104926850A CN 201510421040 A CN201510421040 A CN 201510421040A CN 104926850 A CN104926850 A CN 104926850A
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- iodine
- iodotrimethylsilane
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- hexamethyldisiloxane
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Abstract
The invention provides an iodotrimethylsilane preparation method. The preparation method comprises the following steps that superfine aluminum power and half hexamethyldisiloxane are put in a reaction flask, elementary substance iodine and half hexamethyldisiloxane are put in a constant pressure dropping funnel, vacuumizing and nitrogen replacing are performed on a reaction system, and all the steps are repeated for three times; stirring is started, the temperature rises to 60 DEG C, and hexamethyldisiloxane solutions of the iodine are dropwise added; after dropwise adding is finished, the outer temperature rises to 130 DEG C for backflow, and therefore after being cooled, steam enters the constant pressure dropping funnel to dissolve the undissolved iodine in the constant pressure dropping funnel; after the iodine is dissolved completely and dropwise added in the reaction system, reaction is performed for 2 hours until the reaction is complete; heating is stopped, the temperature is cooled below 30 DEG C, a reaction device is changed into a distillation device to collect main distillate fractions, and then colorless liquid iodotrimethylsilane competitive products are obtained.
Description
Technical field
The present invention relates to a kind of preparation method of Iodotrimethylsilane, belong to the field of chemical synthesis.
Background technology
Iodotrimethylsilane is widely used at pharmaceutical synthesis and organic synthesis field; in pharmaceutical synthesis, the protection reagent of the functional group such as Iodotrimethylsilane Chang Zuowei hydroxyl, is especially used widely in forth generation cynnematin is as the building-up process of cefepime, cefpirome.Iodotrimethylsilane character is active, and the oxygen in atmosphere easily and in air reacts and goes bad, and limits it and preserves, uses.
The synthetic method of Iodotrimethylsilane has kind more than 10, more practical and be easy to the reaction that industrialized synthetic method is hexamethyldisiloxane and iodine and aluminium powder, and the reaction of hexamethyldisilane and iodine.The Iodotrimethylsilane sold in the market contains a lot of lower boiling impurity (as tetramethylsilane and dimethyl diiodo-silane), and this impure product is unfavorable for the synthesis of cynnematin, also likely forms the side effect after medication.
Application number be 200810018420.7 Chinese invention patent describe a kind of synthetic method of Iodotrimethylsilane, the method with hexamethyldisilane and smart iodine for raw material, reaction generates Iodotrimethylsilane crude product, copper powder is added again by Iodotrimethylsilane crude product, reflux, then distills the Iodotrimethylsilane that can obtain refining.The method purification step, copper powder consumption is large, is unfavorable for the reduction of production cost; Particularly breakneck chemical and the high-risk operation such as need of production sodium Metal 99.5 potassium of hexamethyldisilane, and the price of hexamethyldisilane is far above hexamethyldisiloxane, causes the production cost of the method very high.
Application number be 200610097774.6 Chinese invention patent describe a kind of synthetic method of Iodotrimethylsilane, aluminium powder, hexamethyldisiloxane and iodine first react by the method in a kettle., distillation, obtain Iodotrimethylsilane crude product, again Iodotrimethylsilane crude product is placed in still kettle, adds copper powder, heat up, collect cut, be refining Iodotrimethylsilane.The method yield is low, and the thick yield of reaction only has 84.25%, and refining yield only has 78.49%, and the total recovery namely utilizing the method to prepare Iodotrimethylsilane sterling only has 84.25% × 78.49%=66.13%; Purification step, copper powder consumption is large, is unfavorable for the reduction of production cost.The method operation steps comprises and adds smart iodine in batches, because iodine has higher vapour pressure, easily distils, and irritant smell, easily sublimates after distillation, toxic and corrodibility, so this step operates both contaminate environment also serious harm operator.Iodine and aluminium powder are all solids, and the reaction of solid and solid is slow and unstable, and the aluminium triiodide solid that iodine and aluminium powder reaction generate covers the surface of iodine and aluminium powder, hinders further reaction, yield in this way very low.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of preparation method of Iodotrimethylsilane, and this preparation method can obtain highly purified Iodotrimethylsilane, and the method yield is very high, operational safety, production cost are very low.
An object of the present invention is to provide a kind of preparation method of Iodotrimethylsilane, described preparation method with hexamethyldisiloxane, aluminium powder and iodine for reaction raw materials; Be dissolved in hexamethyldisiloxane by iodine in reaction process, react in the mode dripped, described aluminium powder is superfine aluminium power.
In one embodiment of the invention, described preparation method is specially: be placed in reaction flask by the hexamethyldisiloxane of superfine aluminium power and half, and the hexamethyldisiloxane of iodine and half is placed in constant pressure funnel, and reaction system vacuumizes, change rare gas element, three times so repeatedly.Start stirring, be warming up to 60 DEG C, drip the hexamethyl two silica-based oxygen alkane solution of iodine.Dropwise, outer temperature is warming up to 130 DEG C of backflows, enters constant pressure funnel and dissolve undissolved iodine in constant pressure funnel after steam is cooled.After iodine all dissolves and is added dropwise to reaction system, find that reaction reacts completely for 1-2 hour.Stop heating, be cooled to less than 30 DEG C, change reaction unit into water distilling apparatus, collect main distillate fraction, namely obtain the Iodotrimethylsilane fine work of colourless liquid.
In a preferred embodiment of the invention, the molar ratio of hexamethyldisiloxane, iodine and aluminium powder is 1:1.5:1.1 ~ 2; Be preferably 1:1.5:1.6 further.
In another preferred embodiment of the present invention, described superfine aluminium power is the aluminium powder of more than granularity 300 order; Be preferably the aluminium powder between 325 order ~ 800 orders further.
In another preferred embodiment of the present invention, described rare gas element is nitrogen.
Equation of the present invention is as follows:
Reaction mechanism of the present invention is as follows:
In the present invention,
One of innovative point of the present invention: in Iodotrimethylsilane molecule, SiI key is very weak, causes it to be easily fuming in atmosphere variable color, so reaction system is nitrogen.
Innovative point two of the present invention: initiated dissolving in system and added iodine, all solid iodines add constant pressure addition in advance, dissolving iodine with the silica-based oxygen ether of raw material hexamethyl two and product Iodotrimethylsilane is added drop-wise in reaction flask with iodine solution, such operation ensures that iodine is free from environmental pollution and does not also endanger operator, and speed of response is fast, yield is high, avoids all shortcomings in batches adding iodine of document.
Innovative point three of the present invention: adopt superfine aluminium power first, find that speed of response is very fast, and reaction is very thorough, reaction yield is far away higher than common aluminium powder; And Late Cambrian: aluminium powder is thinner, and speed of response is faster, and yield is higher.
Innovative point four of the present invention: expensive iodine is inexcessive, and cheap aluminium powder is excessive, and the Iodotrimethylsilane of generation need not be refined, straight run distillation, and purity is just up to 99.3%.
Embodiment
Further will illustrate the present invention below.It is pointed out that following explanation is only illustrating the technical scheme that application claims is protected, any restriction not to these technical schemes.The content that protection scope of the present invention is recorded with appended claims is as the criterion.
embodiment 1:
Superfine aluminium power (325 order) 8.6 g are added, hexamethyl two silica-based oxygen ether 16.2 g in 250 mL four-hole bottles.One deck rectifying column filler glass spring is first added in constant pressure funnel, then iodine 76.2 g and hexamethyl two silica-based oxygen ether 16.2 g, reaction system vacuumizes, and changes nitrogen, three times so repeatedly.Start stirring, be warming up to 60 DEG C, drip the silica-based oxygen ethereal solution of hexamethyl two of iodine.Dropwise, outer temperature is warming up to 130 DEG C of backflows, enters constant pressure funnel and dissolve undissolved iodine in constant pressure funnel after steam is cooled.After iodine all dissolves and is added dropwise to reaction system, then react and react completely for 1.5 hours.Stop heating, be cooled to less than 30 DEG C, change reaction unit into water distilling apparatus, collect main distillate fraction 104-106 DEG C, obtain 77.3 g colourless liquids, yield 96.6 %, the purity of Iodotrimethylsilane is 99.3%.
Distill complete, be cooled to 140 DEG C, add 80 mL p-Xylol, be cooled to about 60 DEG C, add the aqueous sodium hydroxide solution of 20%, measure solution pH value and regulate PH=6, have a large amount of white precipitate to produce, filter to obtain white aluminium-hydroxide powder, the rate of recovery is close to quantitative.
By filtrate separatory, under condition of ice bath, the aqueous phase vitriol oil regulates PH=1-2.Stir the hydrogen peroxide of lower slowly dropping 30%.Leave standstill, layering.Upper strata is for connecing subdiaphanous water layer, and lower floor is the iodine be precipitated out.Suction filtration obtains fine particle shape iodine, dry, and the rate of recovery is close to quantitative.
embodiment 2:
Superfine aluminium power (800 order) 8.6 g are added, hexamethyl two silica-based oxygen ether 16.2 g in 250 mL four-hole bottles.One deck rectifying column filler glass spring is first added in constant pressure funnel, then iodine 76.2 g and hexamethyl two silica-based oxygen ether 16.2 g, reaction system vacuumizes, and changes nitrogen, three times so repeatedly.Start stirring, be warming up to 60 DEG C, drip the silica-based oxygen ethereal solution of hexamethyl two of iodine.Dropwise, outer temperature is warming up to 130 DEG C of backflows, enters constant pressure funnel and dissolve undissolved iodine in constant pressure funnel after steam is cooled.After iodine all dissolves and is added dropwise to reaction system, then react and react completely for 1 hour.Stop heating, be cooled to less than 30 DEG C, change reaction unit into water distilling apparatus, collect main distillate fraction 104-106 DEG C, obtain 79.6 g colourless liquids, yield 99.5 %, the purity of Iodotrimethylsilane is 99.6%.
The recovery of aluminium hydroxide and thick iodine is with embodiment 1.
embodiment 3:
Common aluminium powder (40 order) 8.6 g are added, hexamethyl two silica-based oxygen ether 16.2 g in 250 mL four-hole bottles.One deck rectifying column filler glass spring is first added in constant pressure funnel, then iodine 76.2 g and hexamethyl two silica-based oxygen ether 16.2 g, reaction system vacuumizes, and changes nitrogen, three times so repeatedly.Start stirring, be warming up to 60 DEG C, drip the silica-based oxygen ethereal solution of hexamethyl two of iodine.Dropwise, outer temperature is warming up to 130 DEG C of backflows, enters constant pressure funnel and dissolve undissolved iodine in constant pressure funnel after steam is cooled.After iodine all dissolves and is added dropwise to reaction system, then react and react completely for 3 hours.Stop heating, be cooled to less than 30 DEG C, change reaction unit into water distilling apparatus, collect the cut 100-150 DEG C containing product Iodotrimethylsilane, obtain 64.9 g red liquids, yield 81.2 %, the purity of Iodotrimethylsilane is 83.3%.
The recovery of aluminium hydroxide and thick iodine is with embodiment 1.
embodiment 4:
Add common aluminium powder (40 order) 8.6 g in 250 mL four-hole bottles, hexamethyl two silica-based oxygen ether 32.4 g, starts stirring, is warming up to 60 DEG C, adds iodine 76.2 g in batches, and outer temperature is warming up to 140 DEG C of backflows, then reacts and react completely for 4 hours.Stop heating, be cooled to less than 30 DEG C, change reaction unit into water distilling apparatus, collect the cut 100-150 DEG C containing product Iodotrimethylsilane, obtain 59.4 g red liquids, yield 74.2 %, the purity of Iodotrimethylsilane is 73.3%.
The recovery of aluminium hydroxide and thick iodine is with embodiment 1.
embodiment 5:
Add superfine aluminium power (800 order) 8.6 g in 250 mL four-hole bottles, hexamethyl two silica-based oxygen ether 32.4 g, starts stirring, is warming up to 60 DEG C, adds iodine 76.2 g in batches, and outer temperature is warming up to 140 DEG C of backflows, then reacts and react completely for 4 hours.Stop heating, be cooled to less than 30 DEG C, change reaction unit into water distilling apparatus, collect the cut 100-150 DEG C containing product Iodotrimethylsilane, obtain 65.7 g red liquids, yield 82.1%, the purity of Iodotrimethylsilane is 78.2%.
The recovery of aluminium hydroxide and thick iodine is with embodiment 1.
embodiment 6:
Superfine aluminium power (200 order) 8.6 g are added, hexamethyl two silica-based oxygen ether 16.2 g in 250 mL four-hole bottles.One deck rectifying column filler glass spring is first added in constant pressure funnel, then iodine 76.2 g and hexamethyl two silica-based oxygen ether 16.2 g, reaction system vacuumizes, and changes nitrogen, three times so repeatedly.Start stirring, be warming up to 60 DEG C, drip the silica-based oxygen ethereal solution of hexamethyl two of iodine.Dropwise, outer temperature is warming up to 130 DEG C of backflows, enters constant pressure funnel and dissolve undissolved iodine in constant pressure funnel after steam is cooled.After iodine all dissolves and is added dropwise to reaction system, then react and react completely for 1 hour.Stop heating, be cooled to less than 30 DEG C, change reaction unit into water distilling apparatus, collect main distillate fraction 104-106 DEG C, obtain 71.5g colourless liquid, yield 89.4%, the purity of Iodotrimethylsilane is 92.4%.
The recovery of aluminium hydroxide and thick iodine is with embodiment 1.
embodiment 7:
Superfine aluminium power (1000 order) 8.6 g are added, hexamethyl two silica-based oxygen ether 16.2 g in 250 mL four-hole bottles.One deck rectifying column filler glass spring is first added in constant pressure funnel, then iodine 76.2 g and hexamethyl two silica-based oxygen ether 16.2 g, reaction system vacuumizes, and changes nitrogen, three times so repeatedly.Start stirring, be warming up to 60 DEG C, drip the silica-based oxygen ethereal solution of hexamethyl two of iodine.Dropwise, outer temperature is warming up to 130 DEG C of backflows, enters constant pressure funnel and dissolve undissolved iodine in constant pressure funnel after steam is cooled.After iodine all dissolves and is added dropwise to reaction system, then react and react completely for 1 hour.Stop heating, be cooled to less than 30 DEG C, change reaction unit into water distilling apparatus, collect main distillate fraction 104-106 DEG C, obtain 70.1g colourless liquid, yield 87.6%, the purity of Iodotrimethylsilane is 97.6%.
The recovery of aluminium hydroxide and thick iodine is with embodiment 1.
Claims (7)
1. a preparation method for Iodotrimethylsilane, described preparation method with hexamethyldisiloxane, aluminium powder and iodine for reaction raw materials; Be dissolved in hexamethyldisiloxane by iodine in reaction process, react in the mode dripped, described aluminium powder is superfine aluminium power.
2. the preparation method of Iodotrimethylsilane according to claim 1, it is characterized in that: described preparation method is specially: the hexamethyldisiloxane of superfine aluminium power and half is placed in reaction flask, the hexamethyldisiloxane of iodine and half is placed in constant pressure funnel, reaction system vacuumizes, change rare gas element, three times so repeatedly; Start stirring, be warming up to 60 DEG C, drip the hexamethyl two silica-based oxygen alkane solution of iodine; Dropwise, outer temperature is warming up to 130 DEG C of backflows, enters constant pressure funnel and dissolve undissolved iodine in constant pressure funnel after steam is cooled; After iodine all dissolves and is added dropwise to reaction system, find that reaction reacts completely for 1-2 hour; Stop heating, be cooled to less than 30 DEG C, change reaction unit into water distilling apparatus, collect main distillate fraction, namely obtain the Iodotrimethylsilane fine work of colourless liquid.
3. the preparation method of Iodotrimethylsilane according to claim 2, it is characterized in that, the molar ratio of hexamethyldisiloxane, iodine and aluminium powder is 1:1.5:1.1 ~ 2.
4. the preparation method of Iodotrimethylsilane according to claim 2, it is characterized in that, described rare gas element is nitrogen.
5. the preparation method of Iodotrimethylsilane according to claim 3, is characterized in that the molar ratio of hexamethyldisiloxane, iodine and aluminium powder is 1:1.5:1.6.
6. superfine aluminium power according to claim 1, is characterized in that described superfine aluminium power is the aluminium powder of granularity more than 300 orders.
7. superfine aluminium power according to claim 6, is characterized in that described superfine aluminium power be granularity is 325 order ~ 800 orders.
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Cited By (2)
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| CN105237559A (en) * | 2015-11-22 | 2016-01-13 | 青岛麦瑞特医药技术有限公司 | Trimethyliodosilane preparing method |
| CN105294752A (en) * | 2015-11-22 | 2016-02-03 | 青岛麦瑞特医药技术有限公司 | Trimethyliodosilane preparation method |
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| CN1962668A (en) * | 2006-11-27 | 2007-05-16 | 扬州三友合成化工有限公司 | Process for synthesizing iodotrimethylsilane |
| CN101230072A (en) * | 2008-02-04 | 2008-07-30 | 吴江信谊化工有限公司 | Preparation method of iodotrimethylsilane |
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2015
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| CN1962668A (en) * | 2006-11-27 | 2007-05-16 | 扬州三友合成化工有限公司 | Process for synthesizing iodotrimethylsilane |
| CN101230072A (en) * | 2008-02-04 | 2008-07-30 | 吴江信谊化工有限公司 | Preparation method of iodotrimethylsilane |
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Cited By (3)
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| CN105237559A (en) * | 2015-11-22 | 2016-01-13 | 青岛麦瑞特医药技术有限公司 | Trimethyliodosilane preparing method |
| CN105294752A (en) * | 2015-11-22 | 2016-02-03 | 青岛麦瑞特医药技术有限公司 | Trimethyliodosilane preparation method |
| CN105237559B (en) * | 2015-11-22 | 2017-09-29 | 陈红 | A kind of preparation method of Iodotrimethylsilane |
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