CN114409692B - Method for preparing hexamethyldisilazane - Google Patents
Method for preparing hexamethyldisilazane Download PDFInfo
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- CN114409692B CN114409692B CN202210022226.6A CN202210022226A CN114409692B CN 114409692 B CN114409692 B CN 114409692B CN 202210022226 A CN202210022226 A CN 202210022226A CN 114409692 B CN114409692 B CN 114409692B
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- molecular sieve
- titanium
- hexamethyldisilazane
- titanium silicalite
- preparation
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000010936 titanium Substances 0.000 claims abstract description 33
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000002808 molecular sieve Substances 0.000 claims abstract description 25
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims abstract description 14
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims abstract description 12
- UGACIEPFGXRWCH-UHFFFAOYSA-N [Si].[Ti] Chemical compound [Si].[Ti] UGACIEPFGXRWCH-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052786 argon Inorganic materials 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims description 19
- 239000011148 porous material Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000012495 reaction gas Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- PZIBOVBPVADPBS-UHFFFAOYSA-J S(=O)(=O)([O-])[O-].[Si+4].S(=O)(=O)([O-])[O-] Chemical compound S(=O)(=O)([O-])[O-].[Si+4].S(=O)(=O)([O-])[O-] PZIBOVBPVADPBS-UHFFFAOYSA-J 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000005051 trimethylchlorosilane Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- -1 silane amine compound Chemical class 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 102100034095 5'(3')-deoxyribonucleotidase, cytosolic type Human genes 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- XLUBVTJUEUUZMR-UHFFFAOYSA-B silicon(4+);tetraphosphate Chemical compound [Si+4].[Si+4].[Si+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XLUBVTJUEUUZMR-UHFFFAOYSA-B 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
A method for preparing hexamethyldisilazane, comprising the steps of: the trimethylsilane reacts with ammonia in the presence of a titanium silicalite molecular sieve (TS-1) catalyst, wherein the titanium silicalite molecular sieve is filled in a reactor, and argon carries a mixture consisting of the trimethylsilane and nitrogen to pass through the titanium silicalite molecular sieve. The method adopts the titanium-silicon molecular sieve catalyst which is easy to prepare, low in price and capable of being recycled, avoids expensive platinum metal catalyst in the prior art, avoids strict requirements on equipment, greatly reduces manufacturing cost, does not generate three wastes, and has the advantages of easy separation of products, high conversion rate and high purity.
Description
Technical Field
The invention relates to a preparation method of a silane amine compound, in particular to a preparation method of hexamethyldisilazane.
Background
Hexamethyldisilazane (HMDS) is an important organosilicon compound and has wide application in the fields of organosilicon chemistry and organic synthesis. HMDS has important application value in the fields of gas chromatography analysis, semiconductor industry photo-etching, rubber industry, surface treating agent, organic synthesis, medicine industry and the like.
HMDS belongs to volatile organic compounds, is colorless transparent liquid, is nontoxic, has slightly amine smell, has the density of 0.770-0.780 g/cm < 3 > at 25 ℃, the refractive index of 1.408 and the boiling range of 125-127 ℃. At present, the synthesis method of HMDS mainly comprises the following steps:
trimethylsilane reacts with ammonia under the catalysis of Pt or Pd. The reaction formula is as follows:
2(CH 3 ) 3 SiH+NH 3 →(CH 3 ) 3 SiNHSi(CH 3 ) 3 +2H 2
trimethyl chlorosilane (TMS) is used as a raw material, ammonia gas is introduced to react under the condition of inert solvent, and then the raw material is rectified to obtain the catalyst. The reaction formula is as follows:
2(CH 3 ) 3 SiCl+NH3→(CH 3 ) 3 SiNHSi(CH 3 ) 3 +2NH 4 Cl
NH 4 Cl+NaOH→NaCl+NH 3 .H 2 O
there are a number of side reactions in this process:
2(CH 3 ) 3 SiCl+H 2 O→(CH 3 ) 3 SiOSi(CH 3 ) 3 +2HCl
HMDS+2H 2 O→(CH 3 ) 3 SiOSi(CH 3 ) 3 +NH 3 .H 2 O
hexamethyldisiloxane is used as a raw material, and reacts with concentrated sulfuric acid to generate silicon sulfate, the silicon sulfate reacts with hydrogen chloride to generate trimethylchlorosilane, and ammonia gas is introduced to prepare HMDS.
And (3) reacting hexamethyldisiloxane with phosphorus pentoxide or phosphoric acid to prepare silicon phosphate, and then introducing ammonia gas to prepare HMDS. The reaction formula is as follows:
3(CH 3 ) 3 SiOSi(CH 3 ) 3 +2H 3 PO 4 →2[(CH 3 ) 3 SiO] 3 P(O)+3H 2 O
2[(CH 3 ) 3 SiO] 3 P(O)+9NH 3 →3(CH 3 ) 3 SiNHSi(CH 3 ) 3 +2(NH 4 ) 3 PO 4
the HMDS is prepared by directly introducing ammonia gas to react with silicon sulfate generated by the reaction of hexamethyldisiloxane and concentrated sulfuric acid. The reaction formula is as follows:
(CH 3 ) 3 SiOSi(CH 3 ) 3 +H 2 SO 4 →(Me 3 Si) 2 SO 4 +H 2 O
(Me 3 Si) 2 SO 4 +3NH 3 →(CH 3 ) 3 SiNHSi(CH 3 ) 3 +(NH 4 ) 2 SO 4
the first method is mostly adopted abroad, the yield is high, the product purity is high, but the requirements on equipment are strict, and the cost is high due to the use of a noble metal catalyst. At present, the latter methods are mainly adopted for domestic production of HMDS, a large amount of inert solvents are adopted in the second method, and finally rectification and separation are needed, the reaction is exothermic, a large amount of NH4Cl particles can be generated, a kettle type intermittent synthesis technology is needed, continuous production is not facilitated, and side reactions can also occur; the third method is similar to the second method; the latter methods have low yield of HMDS, are complex and cumbersome to operate, can generate a large amount of three wastes, and are not beneficial to environmental protection.
TS-1: the titanium-silicon molecular sieve belongs to Pentasil type hetero-atom molecular sieve, is orthorhombic, has a three-dimensional pore canal structure represented by ZSM-5, consists of Z-shaped channels and elliptic straight channels intersected with the Z-shaped channels, is obtained by partially replacing silicon atoms in a pure silicon molecular sieve framework with titanium atoms, has special oxidation-reduction performance due to the introduction of metallic titanium, and shows high-efficiency catalytic property in a mild catalytic system. Such new generation of shape-catalyzing materials is regarded as novel catalysts (which are non-toxic) in the green chemistry field.
The reaction scheme for preparing HMDS by trimethylsilyl amination is as follows:
2(CH 3 ) 3 SiH+NH 3 →(CH 3 ) 3 SiNHSi(CH 3 ) 3 +2H 2
disclosure of Invention
In order to overcome the defects in the prior art, the invention provides a method for preparing hexamethyldisilazane by using a titanium silicalite molecular sieve as a catalyst. The method does not generate three wastes, has high conversion rate and high product purity, can recycle the catalyst, and avoids using noble metal (Pt or Pd) as the catalyst.
The invention aims at realizing the following technical scheme:
a method for preparing hexamethyldisilazane, comprising the steps of:
trimethylsilane is reacted with ammonia in the presence of a titanium silicalite molecular sieve (TS-1) catalyst.
According to the preparation method, the catalyst titanium silicalite molecular sieve is filled in a reactor, and the argon carries a mixture consisting of trimethylsilane and nitrogen to pass through the titanium silicalite molecular sieve.
According to the preparation method of the invention, the generated hexamethyldisilazane is cooled to be liquid at the outlet of the reactor and is separated from the reaction gas mixture.
According to the preparation method of the invention, the molar ratio of the trimethylsilane to the ammonia is 5:1-2:1.
according to the preparation method of the invention, the reaction temperature is 120-240 ℃.
According to the preparation method of the invention, the reaction time is 1-60min.
According to the preparation method of the invention, the titanium silicalite molecular sieve is selected from the group consisting of titanium silicalite with a ratio of 30:1-90:1, preferably 30.
According to the preparation method of the invention, the specific surface area of the titanium silicalite molecular sieve is 300-500m 2 /g, preferably 360m 2 /g。
According to the preparation method of the invention, the pore diameter of the titanium silicalite molecular sieve is 0.55-0.60nm, preferably 0.56-0.58nm.
According to the preparation method of the invention, before the reaction starts, argon is introduced in advance to purge the reactor so as to remove air.
According to the preparation method of the invention, the reaction occurs in a tubular reactor, and a water condensation device is connected to the tail of the tubular reactor.
The invention has the beneficial effects that:
the preparation method adopts the titanium-silicon molecular sieve catalyst which is easy to prepare, low in cost and capable of being recycled, avoids expensive platinum metal catalyst in the prior art, avoids strict requirements on equipment, greatly reduces the manufacturing cost, does not generate three wastes, and has the advantages of easy separation of products, high conversion rate and high purity.
Detailed Description
The preparation method of the present invention will be described in further detail with reference to specific examples. It is to be understood that the following examples are illustrative only and are not to be construed as limiting the scope of the invention. All techniques implemented based on the above description of the invention are intended to be included within the scope of the invention.
The experimental methods used in the following examples are all conventional methods unless otherwise specified; the reagents, materials, etc. used in the examples described below are commercially available unless otherwise specified.
The titanium silicalite molecular sieves used in the examples were purchased from Yao-shi chemical products Inc. of Wuxi, we used three different Si/Ti ratios of TS-1 for the tests, the specific parameters being as follows.
DNT-1：
Ratio of silicon to titanium (Si/Ti) =30
Specific surface area (m) 2 /g)＝360
Pore diameter (nm) =0.56-0.58
DNT-2：
Ratio of silicon to titanium (Si/Ti) =60
Specific surface area (m) 2 /g)＝360
Pore diameter (nm) =0.56-0.58
DNT-3：
Ratio of silicon to titanium (Si/Ti) =90
Specific surface area (m) 2 /g)＝360
Pore diameter (nm) =0.56-0.58
Examples
500g of titanium silicalite molecular sieve (TS-1) is filled into a sleeve with the length of about 1000mm and the inner diameter of about 50mm, the sleeve is heated to the reaction temperature by a thermostat in a jacket (shown in the following table), argon is introduced into the sleeve for 1 to 2 minutes through a feed inlet, air in the reactor is discharged, then small gas cylinders containing trimethylsilane and liquid ammonia are respectively placed on an electronic scale, specified amounts of trimethylsilane (50 g) and ammonia (6 g) are respectively introduced into the sleeve through the feed inlet, after that, a valve of the gas cylinders is closed, argon is introduced from the feed inlet, the titanium silicalite molecular sieve is flushed by the argon carrying a mixture (the mol ratio of reactants is 2:1), a water condenser is arranged at the tail end of the reactor tube, hexamethyldisilazamine (HMDS) generated after the mixed gas passes through the titanium silicalite molecular sieve is condensed into liquid by the water condenser, and then the liquid is collected by a receiver, and unreacted gas is continuously flushed for a period of time (shown in the following table).
The reaction time of the mixture in the reactor in the above examples may be generally 1 to 60 minutes, and the longer the reaction time, the higher the yield, the more time the reaction is sufficient, and the yield can be up to 100% (based on trimethylsilane). The following table gives yield and purity information for different si/ti ratios, different temperatures, different residence time products.
TABLE 1 reaction at 120 ℃ (Si/Ti=90)
TABLE 2 reaction at 120 ℃ (Si/Ti=60)
TABLE 3 reaction at 120 ℃ (Si/Ti=30)
Table 4 reaction at 180 ℃ (Si/Ti=30)
Table 5 reaction at 240 ℃ (Si/Ti=30)
The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiment. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. A method for preparing hexamethyldisilazane, comprising the steps of:
trimethylsilane reacts with ammonia in the presence of a titanium silicalite molecular sieve TS-1 as a catalyst,
the catalyst titanium silicalite molecular sieve TS-1 is filled in a reactor, argon carries a mixture composed of trimethylsilane and ammonia gas, passes through the titanium silicalite molecular sieve,
the reaction temperature is 120-240 ℃,
the silicon-titanium ratio of the titanium-silicon molecular sieve is 30:1-90:1.
2. the process according to claim 1, wherein the hexamethyldisilazane is obtained by cooling the hexamethyldisilazane to a liquid at the outlet of the reactor and separating the hexamethyldisilazane from the reaction gas mixture.
3. The preparation method according to claim 1, wherein the molar ratio of the trimethylsilane to the ammonia gas is 5:1-2:1.
4. the preparation method according to claim 1, wherein the reaction time is 1 to 60 minutes.
5. The preparation method according to claim 1, wherein the silicon-titanium ratio of the titanium-silicon molecular sieve TS-1 is 30:1.
6. The preparation method according to claim 1, wherein the specific surface area of the titanium silicalite molecular sieve TS-1 is 300-500m 2 /g。
7. The preparation method according to claim 1, wherein the pore diameter of the titanium silicalite TS-1 is 0.55-0.60nm.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4115427A (en) * | 1976-09-01 | 1978-09-19 | Dynamit Nobel Aktiengesellschaft | Method of preparing silicon-nitrogen compounds |
| CN101602013A (en) * | 2008-06-12 | 2009-12-16 | 中国石油化工股份有限公司 | The method of modifying of TS-1 titanium-silicon molecular sieve catalyst |
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- 2022-01-10 CN CN202210022226.6A patent/CN114409692B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4115427A (en) * | 1976-09-01 | 1978-09-19 | Dynamit Nobel Aktiengesellschaft | Method of preparing silicon-nitrogen compounds |
| CN101602013A (en) * | 2008-06-12 | 2009-12-16 | 中国石油化工股份有限公司 | The method of modifying of TS-1 titanium-silicon molecular sieve catalyst |
Non-Patent Citations (1)
| Title |
|---|
| Dehydrocoupling of Ammonia and Silanes Catalyzed by Dimet hyltitanocene;Hua Qin Liu et al.;《Organometallics》;第11卷;822-827页 * |
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