CN105237559A - Trimethyliodosilane preparing method - Google Patents
Trimethyliodosilane preparing method Download PDFInfo
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- CN105237559A CN105237559A CN201510814695.1A CN201510814695A CN105237559A CN 105237559 A CN105237559 A CN 105237559A CN 201510814695 A CN201510814695 A CN 201510814695A CN 105237559 A CN105237559 A CN 105237559A
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- Prior art keywords
- iodotrimethylsilane
- preparation
- elemental iodine
- anhydrous
- hexamethyldisiloxane
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- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 title claims abstract description 88
- 238000000034 method Methods 0.000 title claims abstract description 24
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 33
- 239000011630 iodine Substances 0.000 claims abstract description 33
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000004821 distillation Methods 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 238000010792 warming Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 4
- 238000005304 joining Methods 0.000 claims description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 2
- 229910052786 argon Inorganic materials 0.000 claims 1
- 239000001307 helium Substances 0.000 claims 1
- 229910052734 helium Inorganic materials 0.000 claims 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims 1
- 238000010992 reflux Methods 0.000 abstract description 7
- 229940055858 aluminum chloride anhydrous Drugs 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- 239000004411 aluminium Substances 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 238000013019 agitation Methods 0.000 description 7
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000010926 purge Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229940063656 aluminum chloride Drugs 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- -1 amino, hydroxyl Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960002100 cefepime Drugs 0.000 description 1
- HVFLCNVBZFFHBT-ZKDACBOMSA-N cefepime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1C[N+]1(C)CCCC1 HVFLCNVBZFFHBT-ZKDACBOMSA-N 0.000 description 1
- DKOQGJHPHLTOJR-WHRDSVKCSA-N cefpirome Chemical compound N([C@@H]1C(N2C(=C(C[N+]=3C=4CCCC=4C=CC=3)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 DKOQGJHPHLTOJR-WHRDSVKCSA-N 0.000 description 1
- 229960000466 cefpirome Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- UYZARHCMSBEPFF-UHFFFAOYSA-N diiodo(dimethyl)silane Chemical compound C[Si](C)(I)I UYZARHCMSBEPFF-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention discloses a trimethyliodosilane preparing method. The method comprises the steps of adding aluminum chloride anhydrous and hexamethyldisiloxane to a reaction container in the presence of protective gas, conducting stirring, increasing the temperature to 40-50 DEG C, then adding the iodine elementary substance, increasing bath temperature to 125-140 DEG C, conducting reflux reaction for 1-1.5 h, changing the device to be a distilling device, conducting atmospheric distillation, and collecting 106-107 DEG C cut fraction to obtain trimethyliodosilane. The method has the advantages that the yield of trimethyliodosilane is increased, purification is easy, conditions are mild, and large-scale production and popularization are facilitated.
Description
Technical field
The invention belongs to chemical field, particularly, relate to a kind of preparation method of Iodotrimethylsilane.
Background technology
Iodotrimethylsilane is at the protection reagent of the functional groups such as pharmaceutical synthesis and organic synthesis field Chang Zuowei amino, hydroxyl, sulfydryl; apply widely because the advantages such as its activity is high, reaction conditions is gentle make it have, especially at pharmaceutical synthesis as the application in the synthesis of cefepime, cefpirome.
At present, the synthetic method of Iodotrimethylsilane has multiple, and industrial conventional synthetic method is that hexamethyldisiloxane and iodine and aluminium powder react and prepare Iodotrimethylsilane.The Iodotrimethylsilane many employings aforesaid method sold in the market, Iodotrimethylsilane prepared by the method contains a lot of impurity such as lower boiling material (as tetramethylsilane and dimethyl diiodo-silane), these low-boiling point materials are difficult to be separated from the product of subsequent reactions cause product to be difficult to purifying, special in pharmaceutical synthesis, affect the quality of the product of medicine, even can have an impact to Drug safety.
In addition, preparation method's ubiquity yield of prior art Iodotrimethylsilane is low, the problem that purity is on the low side.Such as; the people such as MichaelE.Jung are at Org.Synth. (1979; 59; p35) a kind of preparation method of Iodotrimethylsilane is disclosed; the method comprises: under nitrogen protection; aluminium powder is joined in hexamethyl siloxane; then iodine is dripped at 60 DEG C in 55 minutes; to dropwise at about 140 DEG C reflux 1.5 hours; colorless fraction is collected in finally distillation; Iodotrimethylsilane, yield only has 82-88%, and the method is strict especially to operating the operational requirement that particularly iodine adds.
Patent application CN1962668A discloses 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 Iodotrimethylsilane yield after refining only has about 65%.In the method, the aluminium triiodide that iodine and aluminium powder solid-solid reaction generate covers the surface of iodine and aluminium powder, hinders further reaction, yield in this way very low.Further, treating process uses and uses copper powder in a large number, and cost is higher and can produce extra industrial waste.
Therefore, in view of the importance of Iodotrimethylsilane in organic, pharmaceutical synthesis, this area needs that a kind of product yield is high, purity is high, the method preparing Iodotrimethylsilane of reaction conditions temperature badly.
Summary of the invention
The object of the invention is to overcome and above-mentionedly existingly prepare in the method for Iodotrimethylsilane that yield is low, purifying products is difficult and the defects such as complex process, provide a kind of high for product yield, purity is simple, the preparation method of the Iodotrimethylsilane of reaction conditions temperature.
The present inventor is found by research, the essence of the reaction of hexamethyldisiloxane and elemental iodine and aluminium powder be aluminium powder first and elemental iodine react and generate aluminium triiodide, then hexamethyldisiloxane and aluminium triiodide react and generate Iodotrimethylsilane.And aluminium powder adds a kind of very strong lytic reagent of elemental iodine as covalent halide series, large calorimetric can be released instantaneously in the reaction process generating aluminium triiodide, condition is difficult to control, cause the part Iodotrimethylsilane of raw material hexamethyldisiloxane and generation to decompose, such that yield is low, impurity increases.Commercially available aluminium triiodide is expensive and character unstable.The present inventor finds after hexamethyldisiloxane and aluminum chloride mixing, then add elemental iodine, can generate Iodotrimethylsilane rapidly, reaction does not need excessive temperature to cause, and reaction process is stablized, simple distillation can obtain highly purified Iodotrimethylsilane.In addition, add elemental iodine in batches, make stable reaction and continuous print moves to the direction of Iodotrimethylsilane, improve reaction yield further.
To achieve these goals, the invention provides a kind of preparation method of Iodotrimethylsilane, the method comprises the following steps:
Under shielding gas exists; aluminum trichloride (anhydrous), hexamethyldisiloxane are joined in reaction vessel; start stirring, be warming up to 40-50 DEG C, then add elemental iodine; elemental iodine has added rear bath temperature rise to 120-140 DEG C; reaction backflow 1-1.5 hour, device changes water distilling apparatus into, air distillation; collect 106-107 DEG C of cut, obtain Iodotrimethylsilane.
In the present invention, in order to improve yield and the atom utilization of reaction further, under preferable case, the mol ratio of the consumption of hexamethyldisiloxane, aluminum trichloride (anhydrous) and elemental iodine is 1:1.2-1.5:3-4.5; Under further preferable case, the mol ratio of the consumption of hexamethyldisiloxane, aluminum trichloride (anhydrous) and elemental iodine is 1:1.2-1.3:3.5-4.
In the present invention, contriver finds, the aluminum trichloride (anhydrous) of different-grain diameter is used all to have impact to the yield of reaction and reaction efficiency, such as, the median size of aluminum trichloride (anhydrous) is excessive, makes aluminum chloride and the too small long reaction time of elemental iodine contact area, the median size of aluminum trichloride (anhydrous) is too small, and then easily Particulate accumulation reaction is uneven, the problem such as cause aluminum trichloride (anhydrous) to react insufficient and the reaction times is long.Under preferable case, the median size of Aluminum chloride anhydrous of the present invention is 75-100 μm.Stable reaction, fast and product yield is high can be ensured at the aluminum trichloride (anhydrous) of above-mentioned scope.
In order to improve reaction yield further, under preferable case, described elemental iodine divides three times by feed hopper and adds, and total joining day is 15-25 minute.
In the present invention, suitable reaction vessel can be selected as required, such as there-necked flask, feed hopper, prolong, thermometer or mechanical stirring etc. can be assembled as required.Preferably under agitation react in the present invention, stirring means can adopt mechanical stirring or the magnetic agitation of this area routine.
In the present invention, excessive elemental iodine can be reclaimed by the ordinary method of this area.
Compared with prior art, the invention has the advantages that: 1. reaction is faster, and yield is higher; 2. impurity is few, without lower-boiling impurity generation, purifying is simple, and by simple distillation, product purity can reach more than 99%.
With regard to the beneficial effect that preparation method of the present invention brings, contriver infers the reaction mechanism of same experience aluminium triiodide in reaction process of the present invention, only to generate the activation energy of aluminium triiodide lower in the present invention, it is easier to react, condition more easily controls, and avoids and generates impurity to the further cracking of product and raw material.
Other features and advantages of the present invention are described in detail in embodiment part subsequently.
Embodiment
Below the specific embodiment of the present invention is described in detail.Should be understood that, embodiment described herein, only for instruction and explanation of the present invention, is not limited to the present invention.
Below will be described the present invention by embodiment.
Embodiment 1
A preparation method for Iodotrimethylsilane, the method comprises the following steps:
250ml there-necked flask, device feed hopper, nitrogen conduit and reflux condensing tube, open nitrogen purging, add aluminum trichloride (anhydrous) 17.3g (130mmol, median size is 85 μm) and hexamethyldisiloxane 16.2g (100mmol), start magnetic agitation, be warming up to 40 DEG C, then divided by feed hopper and add elemental iodine 88.8g (350mmol for three times, each 29.6g), each feed time is 5 minutes, elemental iodine has added rear bath temperature rise to 120 DEG C, reaction backflow 1 hour, device changes water distilling apparatus into, air distillation, collect 106-107 DEG C of cut, obtain Iodotrimethylsilane 39g, purity 99.8%, yield 97.4%.
Embodiment 2
A preparation method for Iodotrimethylsilane, the method comprises the following steps:
250ml there-necked flask, device feed hopper, nitrogen conduit and reflux condensing tube, open nitrogen purging, add aluminum trichloride (anhydrous) (120mmol, median size is 100 μm) and hexamethyldisiloxane 16.2g (100mmol), start magnetic agitation, be warming up to 45 DEG C, then divided by feed hopper and add elemental iodine 104.4g (400mmol for three times, each 33.8g), each feed time is 8 minutes, elemental iodine has added rear bath temperature rise to 125 DEG C, reaction backflow 1.2 hours, device changes water distilling apparatus into, air distillation, collect 106-107 DEG C of cut, obtain Iodotrimethylsilane 38.6g, purity 99.8%, yield 96.7%.
Embodiment 3
A preparation method for Iodotrimethylsilane, the method comprises the following steps:
250ml there-necked flask, device feed hopper, nitrogen conduit and reflux condensing tube, open nitrogen purging, add aluminum trichloride (anhydrous) (125mmol median size is 75 μm) and hexamethyldisiloxane 16.2g (100mmol), start magnetic agitation, be warming up to 50 DEG C, then divided by feed hopper and add elemental iodine 91.5g (360mmol for three times, each 30.5g), each feed time is 7 minutes, elemental iodine has added rear bath temperature rise to 130 DEG C, reaction backflow 1 hour, device changes water distilling apparatus into, air distillation, collect 106-107 DEG C of cut, obtain Iodotrimethylsilane 38.6g, purity 99.5%, yield 96.4%.
Embodiment 4
A preparation method for Iodotrimethylsilane, the method comprises the following steps:
250ml there-necked flask, device feed hopper, nitrogen conduit and reflux condensing tube, open nitrogen purging, add aluminum trichloride (anhydrous) (150mmol, median size is 150 μm) and hexamethyldisiloxane 16.2g (100mmol), start magnetic agitation, be warming up to 40 DEG C, then divided by feed hopper and add elemental iodine 76.2g (300mmol for three times, each 25.4g), each feed time is 5 minutes, elemental iodine has added rear bath temperature rise to 140 DEG C, reaction backflow 1.2 hours, device changes water distilling apparatus into, air distillation, collect 106-107 DEG C of cut, obtain Iodotrimethylsilane 38.0g, purity 99.4%, yield 94.9%.
Embodiment 5
A preparation method for Iodotrimethylsilane, the method comprises the following steps:
250ml there-necked flask, device feed hopper, nitrogen conduit and reflux condensing tube, open nitrogen purging, add aluminum trichloride (anhydrous) (140mmol, median size is 30 μm) and hexamethyldisiloxane 16.2g (100mmol), start magnetic agitation, be warming up to 45 DEG C, then divided by feed hopper and add elemental iodine 114.3g (450mmol for three times, each 38.1g), each feed time is 5 minutes, elemental iodine has added rear bath temperature rise to 135 DEG C, reaction backflow 1.5 hours, device changes water distilling apparatus into, air distillation, collect 106-107 DEG C of cut, obtain Iodotrimethylsilane 37.8g, purity 99.6%, yield 94.4%.
Comparative example 1
As the preparation method of the Iodotrimethylsilane of embodiment 1, difference is, does not add aluminum trichloride (anhydrous), obtains Iodotrimethylsilane 35.2g, purity 92.5%, yield 87.9%.
To sum up, method provided by the invention can improve the yield of Iodotrimethylsilane, and product purification is simple, mild condition, and speed of response is fast, simple, is particularly suitable for scale operation and Iodotrimethylsilane is prepared in popularization.
More than describe the preferred embodiment of the present invention in detail; but the present invention is not limited to the detail in above-mentioned embodiment, within the scope of technical conceive of the present invention; can carry out multiple simple variant to technical scheme of the present invention, these simple variant all belong to protection scope of the present invention.
It should be noted that in addition, each concrete technical characteristic described in above-mentioned embodiment, in reconcilable situation, can be combined by any suitable mode, in order to avoid unnecessary repetition, the present invention illustrates no longer separately to various possible array mode.In addition, also can carry out arbitrary combination between various different embodiment of the present invention, as long as it is without prejudice to thought of the present invention, it should be considered as content disclosed in this invention equally.
Claims (6)
1. a preparation method for Iodotrimethylsilane, is characterized in that, the method comprises the following steps:
Under shielding gas exists; aluminum trichloride (anhydrous), hexamethyldisiloxane are joined in reaction vessel; start stirring, be warming up to 40-50 DEG C, then add elemental iodine; elemental iodine has added rear bath temperature rise to 120-140 DEG C; reaction backflow 1-1.5 hour, device changes water distilling apparatus into, air distillation; collect 106-107 DEG C of cut, obtain Iodotrimethylsilane.
2. preparation method according to claim 1, is characterized in that, the mol ratio of the consumption of hexamethyldisiloxane, aluminum trichloride (anhydrous) and elemental iodine is 1:1.2-1.5:3-4.5.
3. preparation method according to claim 2, is characterized in that, the mol ratio of the consumption of hexamethyldisiloxane, aluminum trichloride (anhydrous) and elemental iodine is 1:1.2-1.3:3.5-4.
4. according to the preparation method in claim 1-3 described in any one, it is characterized in that, the median size of described aluminum trichloride (anhydrous) is 75-100 μm.
5. according to the preparation method in claim 1-3 described in any one, it is characterized in that, described elemental iodine divides three times by feed hopper and adds, and total joining day is 15-25 minute.
6. preparation method according to claim 1, is characterized in that, described shielding gas is one or more in helium, argon gas and nitrogen.
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| CN201510814695.1A CN105237559B (en) | 2015-11-22 | 2015-11-22 | A kind of preparation method of Iodotrimethylsilane |
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| CN201510814695.1A CN105237559B (en) | 2015-11-22 | 2015-11-22 | A kind of preparation method of Iodotrimethylsilane |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109836448A (en) * | 2019-04-08 | 2019-06-04 | 浙江海洲制药有限公司 | A method of preparing Iodotrimethylsilane |
| WO2021217048A1 (en) * | 2020-04-24 | 2021-10-28 | Entegris, Inc. | Method of preparing iodosilanes and compositions therefrom |
Citations (1)
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| CN104926850A (en) * | 2015-07-17 | 2015-09-23 | 山东博苑医药化学有限公司 | Iodotrimethylsilane preparation method |
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2015
- 2015-11-22 CN CN201510814695.1A patent/CN105237559B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104926850A (en) * | 2015-07-17 | 2015-09-23 | 山东博苑医药化学有限公司 | Iodotrimethylsilane preparation method |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109836448A (en) * | 2019-04-08 | 2019-06-04 | 浙江海洲制药有限公司 | A method of preparing Iodotrimethylsilane |
| WO2021217048A1 (en) * | 2020-04-24 | 2021-10-28 | Entegris, Inc. | Method of preparing iodosilanes and compositions therefrom |
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| CN105237559B (en) | 2017-09-29 |
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