CN102718789A - Preparation process of trimethylsilylimidazole - Google Patents
Preparation process of trimethylsilylimidazole Download PDFInfo
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- CN102718789A CN102718789A CN2012101871640A CN201210187164A CN102718789A CN 102718789 A CN102718789 A CN 102718789A CN 2012101871640 A CN2012101871640 A CN 2012101871640A CN 201210187164 A CN201210187164 A CN 201210187164A CN 102718789 A CN102718789 A CN 102718789A
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- tsim
- reaction
- temperature
- preparation technology
- chlorosilane
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- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 21
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052753 mercury Inorganic materials 0.000 claims abstract description 6
- 238000005516 engineering process Methods 0.000 claims description 17
- 239000005051 trimethylchlorosilane Substances 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 16
- 238000000605 extraction Methods 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 150000002460 imidazoles Chemical class 0.000 claims description 8
- 238000013019 agitation Methods 0.000 claims description 5
- 238000004458 analytical method Methods 0.000 claims description 5
- 210000003298 dental enamel Anatomy 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 238000005070 sampling Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- -1 amine nitrogenous compound Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- 238000001816 cooling Methods 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Abstract
The invention discloses a preparation process of trimethylsilylimidazole. The preparation process includes the specific steps of (1) reaction: firstly, placing chlorotrimethylsilane into a mixing tank, secondly, adding imidazole in batch under the condition of mixing within three hours, performing reaction under a -200-0mm mercury column and controlling the temperature below 60 DEG C; and (2) rectification: placing qualified liquid into a rectification column, extracting the chlorotrimethylsilane from the column at the temperature lower than or equal to 92 DEG C, and then extracting the trimethylsilylimidazole by cooling. By the aid of the process, reaction can be performed at the normal temperature, the concentration of hydrogen chloride in a system is reduced to approximately approach zero content, and reaction inhibition caused by the hydrogen chloride is avoided.
Description
Technical field
The present invention relates to a kind of TSIM preparation technology.
Background technology
At present TSIM preparation technology adopts the hexamethyldisilazane synthesis method more, promptly under the reflux condition in two steps: one, esterification (vitriol oil) reaction, two, sulfuric ester synthesizes TSIM with the imidazoles direct reaction.Its shortcoming is: 1. technical process is long, needs preparation raw material hexamethyldisilazane, and facility investment is big, operates wayward.2. operating environment is poor, pollutes to weigh, and the ammonia of generation can cause equipment corrosion.3. there is by product ammonium sulfate to generate, causes product purity to descend.4. temperature is crossed when hanging down after the final product condensation, can cause return line to stop up, and material reaction is not thorough simultaneously.
The greatest problem of former technology is in reaction process, to have side reaction, and the result makes that operation is wayward, and technical process is long, and product yield significantly reduces, and cuts purity and descends.
Summary of the invention
The present invention is directed to the problem in the background technology; Researched and developed a kind of TSIM preparation technology, purpose is: in technology, add chlorine hydride absorbent, hydrogen cloride concentration in the reduction system; Reaction can be carried out at a lower temperature smoothly voluntarily, prevents the generation of inhibited reaction.
Technical solution of the present invention:
TSIM preparation technology, concrete steps are:
1, reaction: at first in stirring tank, drop into tri-methyl-chlorosilane, portion-wise addition imidazoles under agitation requires in 3 hours, to add and accomplishes then; Be reflected at-carry out under 200～0mm mercury column, temperature is controlled at below 60 ℃; The hydrogen chloride gas that reaction produces is absorbed through resorber and obtains >=30% concentrated hydrochloric acid through pressurization and cryogenic unit after agent absorbs; After finishing, reaction stops to stir the sampling fluid analysis.
2, rectifying: qualified liquid is dropped in the rectifying tower still extraction tri-methyl-chlorosilane in≤92 ℃ of towers, the extraction product TSIM of lowering the temperature then.
The proportioning of said tri-methyl-chlorosilane and imidazoles is 3.0～3.2:0.9～1.1.
Said absorption agent is ammonia, amine nitrogenous compound or earth alkali metal.
Said stirring tank is the enamel stirring tank.
The volume of said stirring tank is 1m
3
Said step 1 temperature control is lowered the temperature with rate of addition or chuck cold water and is realized.
The tri-methyl-chlorosilane of said step 2 extraction recycles.
The reaction formula that TSIM prepares in the process is:
1, main reaction:
2, side reaction:
Beneficial effect of the present invention:
1. this technology makes and is reflected at normal temperature and can carries out, and hydrogen cloride concentration in the system is reduced almost reach 0 content, avoided the generation of reaction because of the hydrogenchloride inhibited reaction like this, thereby made 1. technical process shorten, and investment reduces; 2. reaction is easy to control, and process cost reduces; 3. yield significantly improves, and reduces production costs.
2. this programme feeds intake according to the scientific approach proportioning, reaches the effect of complete reaction.Distill out surplus materials and repeat to reuse the no waste generation.
Description of drawings
Accompanying drawing is a process flow diagram of the present invention.
Embodiment
Below in conjunction with accompanying drawing and embodiment the present invention is further specified.
Embodiment 1
1, reaction: at first at 1m
3Drop into tri-methyl-chlorosilane 600kg in the enamel stirring tank, under agitation add imidazoles then several times and amount to 180kg, require in 3 hours, to add and accomplish; Be reflected at-carry out under the 200mm mercury column, temperature is controlled at below 60 ℃, and temperature control is lowered the temperature with rate of addition or chuck cold water and realized.The hydrogen chloride gas that reaction produces obtains >=30% concentrated hydrochloric acid through pressurization and cryogenic unit after resorber is absorbed by ammonia; After finishing, reaction stops to stir the sampling fluid analysis.
2, rectifying: qualified liquid is dropped in the rectifying tower still, extraction tri-methyl-chlorosilane in≤92 ℃ of towers, tri-methyl-chlorosilane recycles; The extraction product TSIM of lowering the temperature then.
Above-mentioned reaction can produce the TSIM product of 343.2kg, and yield is 91.5%.
Embodiment 2
1, reaction: at first at 1m
3Drop into tri-methyl-chlorosilane 620kg in the enamel stirring tank, under agitation add imidazoles then several times and amount to 200kg, require in 3 hours, to add and accomplish; Be reflected at-carry out under 200～0mm mercury column, temperature is controlled at below 60 ℃, and temperature control is lowered the temperature with rate of addition or chuck cold water and realized.The hydrogen chloride gas that reaction produces obtains >=30% concentrated hydrochloric acid through pressurization and cryogenic unit after resorber is received by the amine aspiration; After finishing, reaction stops to stir the sampling fluid analysis.
2, rectifying: qualified liquid is dropped in the rectifying tower still, extraction tri-methyl-chlorosilane in≤92 ℃ of towers, tri-methyl-chlorosilane recycles; The extraction product TSIM of lowering the temperature then.
Above-mentioned reaction can produce the TSIM product of 380.3kg, and yield is 92.1%.
Embodiment 3
1, reaction: at first at 1m
3Drop into tri-methyl-chlorosilane 640kg in the enamel stirring tank, under agitation add imidazoles then several times and amount to 220kg, require in 3 hours, to add and accomplish; Be reflected at-carry out under 200～0mm mercury column, temperature is controlled at below 60 ℃, and temperature control is lowered the temperature with rate of addition or chuck cold water and realized.The hydrogen chloride gas that reaction produces obtains >=30% concentrated hydrochloric acid through pressurization and cryogenic unit after resorber is absorbed by earth alkali metal; After finishing, reaction stops to stir the sampling fluid analysis.
2, rectifying: qualified liquid is dropped in the rectifying tower still, extraction tri-methyl-chlorosilane in≤92 ℃ of towers, tri-methyl-chlorosilane recycles; The extraction product TSIM of lowering the temperature then.
Above-mentioned reaction can produce the TSIM product of 418.6kg, and yield is 92.3%.
Claims (7)
1. TSIM preparation technology, concrete steps are:
(1) reaction: at first in stirring tank, drop into tri-methyl-chlorosilane, portion-wise addition imidazoles under agitation requires in 3 hours, to add and accomplishes then; Be reflected at-carry out under 200～0mm mercury column, temperature is controlled at below 60 ℃; The hydrogen chloride gas that reaction produces is absorbed through resorber and obtains >=30% concentrated hydrochloric acid through pressurization and cryogenic unit after agent absorbs; After finishing, reaction stops to stir the sampling fluid analysis;
(2) rectifying: qualified liquid is dropped in the rectifying tower still extraction tri-methyl-chlorosilane in≤92 ℃ of towers, the extraction product TSIM of lowering the temperature then.
2. TSIM preparation technology as claimed in claim 1 is characterized in that: the proportioning of said tri-methyl-chlorosilane and imidazoles is 3.0～3.2:0.9～1.1.
3. TSIM preparation technology as claimed in claim 1 is characterized in that: said absorption agent is ammonia, amine nitrogenous compound or earth alkali metal.
4. TSIM preparation technology as claimed in claim 1 is characterized in that: said stirring tank is the enamel stirring tank.
5. like claim 1 or 4 described TSIM preparation technologies, it is characterized in that: the volume of said stirring tank is 1m
3
6. TSIM preparation technology as claimed in claim 1 is characterized in that: the control of said step (1) temperature is lowered the temperature with rate of addition or chuck cold water and is realized.
7. TSIM preparation technology as claimed in claim 1 is characterized in that: the tri-methyl-chlorosilane of said step (2) extraction recycles.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101871640A CN102718789A (en) | 2012-06-08 | 2012-06-08 | Preparation process of trimethylsilylimidazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101871640A CN102718789A (en) | 2012-06-08 | 2012-06-08 | Preparation process of trimethylsilylimidazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102718789A true CN102718789A (en) | 2012-10-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2012101871640A Pending CN102718789A (en) | 2012-06-08 | 2012-06-08 | Preparation process of trimethylsilylimidazole |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104496908A (en) * | 2014-12-24 | 2015-04-08 | 江苏康乐新材料科技有限公司 | Preparation method of carbonyl diimidazole |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4965366A (en) * | 1984-05-07 | 1990-10-23 | Ppg Industries, Inc. | Method for producing 1-(trisubstituted silyl)azoles |
| CN1498204A (en) * | 2001-03-16 | 2004-05-19 | Method for production of urea | |
| CN101613367A (en) * | 2009-07-22 | 2009-12-30 | 吉林新亚强生物化工有限公司 | The preparation method of trimethylethoxysilane |
-
2012
- 2012-06-08 CN CN2012101871640A patent/CN102718789A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4965366A (en) * | 1984-05-07 | 1990-10-23 | Ppg Industries, Inc. | Method for producing 1-(trisubstituted silyl)azoles |
| CN1498204A (en) * | 2001-03-16 | 2004-05-19 | Method for production of urea | |
| CN101613367A (en) * | 2009-07-22 | 2009-12-30 | 吉林新亚强生物化工有限公司 | The preparation method of trimethylethoxysilane |
Non-Patent Citations (1)
| Title |
|---|
| T. N. KOMAROVA ET AL.: "Synthesis and Structure of Silyl-Substituted Imidazol-2-ylidenes and Their Precursors", 《RUSSIAN JOURNAL OF GENERAL CHEMISTRY》, vol. 77, no. 6, 23 May 2007 (2007-05-23), pages 1002 - 1005 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104496908A (en) * | 2014-12-24 | 2015-04-08 | 江苏康乐新材料科技有限公司 | Preparation method of carbonyl diimidazole |
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| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
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Application publication date: 20121010 |