CN103641710A - Synthesis method for trimesoyl chloride - Google Patents
Synthesis method for trimesoyl chloride Download PDFInfo
- Publication number
- CN103641710A CN103641710A CN201310646526.2A CN201310646526A CN103641710A CN 103641710 A CN103641710 A CN 103641710A CN 201310646526 A CN201310646526 A CN 201310646526A CN 103641710 A CN103641710 A CN 103641710A
- Authority
- CN
- China
- Prior art keywords
- trimethylsilyl chloride
- pyromellitic trimethylsilyl
- synthetic method
- reaction
- sulfur oxychloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000001308 synthesis method Methods 0.000 title abstract 3
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims abstract description 32
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000004821 distillation Methods 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 20
- 238000010189 synthetic method Methods 0.000 claims description 12
- -1 benzyl triethyl ammonium ammonium halide Chemical class 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical group C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 9
- 239000012535 impurity Substances 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 5
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000036632 reaction speed Effects 0.000 abstract 1
- 238000009413 insulation Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method for trimesoyl chloride. The synthesis method comprises the following steps of reacting trimesic acid with thionyl chloride in the premise of a catalyst; performing distillation to remove the thionyl chloride after reaction, and performing distillation under reduced pressure to obtain the trimesoyl chloride. According to the method, the thionyl chloride is used as a reaction raw material as well as a solvent, and the mixing of other solvent impurities is avoided, so that pollution is reduced; process equipment is simple and low in energy consumption and cost; particularly, the whole process is high in reaction speed, fewer impurities are produced, the purity of a distilled product is 99.5 percent high, the yield is over 95 percent, and the product has good economic benefits, and is easy to industrially produce.
Description
Technical field
The invention belongs to organic synthesis field, be specifically related to a kind of synthetic method of pyromellitic trimethylsilyl chloride.
Technical background
Pyromellitic trimethylsilyl chloride is a kind of important chemical feedstocks, main as producing various polyamide-based reverse osmosis membranes, thereby is applied to the aspects such as highly purified and gas delivery of sea water desaltination, water.Along with developing rapidly of polymer chemistry and materials chemistry, become gradually one of popular in the world research field.
Pyromellitic trimethylsilyl chloride adopts phosgene or triphosgene to react and produce with trimesic acid more at present.< < fine chemistry industry > > (08 phase in 2005) has reported one piece of < < Preparation of Trimesoyl Chloride from Trimesoyl Acid Using Triphosgene > >, this technique is introduced, triphosgene is solid Poison, and can also decompose and produce highly toxic product phosgene, hazardness is very large.< < fuel and chemical industry > > have reported the development > > of one piece of < < pyromellitic trimethylsilyl chloride in (in January, 1991), introduced with sulfur oxychloride and the synthetic pyromellitic trimethylsilyl chloride of trimesic acid, yield is 85～89%, purity after refining is higher, but its yield is on the low side.Also have data introduction to take trimesic acid as raw material, react preparation with phosphorus oxychloride (or phosphorus pentachloride), yield is 90%, but this method impurity is many and difficult separated, and yield is on the low side.
According to data introduction, Japan has developed with 1,3,5-trichlorobenzene as raw material, under uviolizing, 65 ℃, 98～490KPa condition, reacts generate pyromellitic trimethylsilyl chloride in sodium hydroxide, ethanol with cobalt-carbonyl, and its yield is 85.5%.The direct method of du pont company exploitation is under 200 ℃, 17MPa pressure, the reaction under nickelous chloride exists of sym-trimethylbenzene and sulfur oxychloride, resultant of reaction again with sulfurous gas effect, obtain pyromellitic trimethylsilyl chloride.Above technique relates to ultraviolet ray and High Temperature High Pressure, and high to processing unit requirement, energy consumption is high, and corresponding production cost is also high.
Summary of the invention
For the deficiencies in the prior art, the object of this invention is to provide a kind of synthetic method of pyromellitic trimethylsilyl chloride, whole procedure is to being safe from harm property of environment; Processing unit of the present invention is simple, energy consumption is little, cost is low, and especially fast, impurity is few in reaction, and product purity is high, and purity is higher than 99.5%, and yield reaches more than 95%, good in economic efficiency, is easy to suitability for industrialized production.
The synthetic method of pyromellitic trimethylsilyl chloride of the present invention, comprises the following steps:
(1) by trimesic acid and sulfur oxychloride under catalyst action, reaction;
(2) reacted rear first distillation and removed sulfur oxychloride, then underpressure distillation obtains pyromellitic trimethylsilyl chloride.
Wherein:
In step (1), the mol ratio of trimesic acid and sulfur oxychloride is 1:3.5～1:10, trimesic acid reacts mol ratio with the theory of sulfur oxychloride be 1:3, but sulfur oxychloride is simultaneously as solvent, so selecting both mol ratios is 1:3.5～1:10, can can accelerate speed of reaction again by sufficient reacting, and mol ratio while surpassing 1:10 solvent sulfur oxychloride too many, increased the energy expenditure of distilation steps, both wasted time and energy, increased again unit consumption, cost is increased, so reasonably proportioning is 1:3.5～1:10, wherein sulfur oxychloride is reaction raw materials and solvent, the present invention does not need additionally to add solvent, do not sneak into other solvent impurity, reduced the generation of polluting.
In step (1), temperature of reaction is 60～80 ℃, and the time is 5～15 hours.
In step (1), catalyzer is organic amine or quaternary ammonium salt phase transfer catalyst.
Catalyzer is preferably one or more the mixture in triphenylphosphine oxide, DMF, N,N-dimethylacetamide, benzyl triethyl ammonium ammonium halide or benzyl tributyl ammonium halide in step (1).The present invention is through creative experiments, and the preferred catalyzer of above suitable body series has advantages of that consumption is few, catalytic efficiency is high, easy separation and noresidue.Catalyst levels is 0.1%～3% of trimesic acid quality.
In step (2), distillation temperature is 120 ℃, and underpressure distillation pressure is-0.095MPa that temperature is 172～183 ℃.
In sum, the present invention has the following advantages:
(1) sulfur oxychloride is that reaction raw materials is used as again solvent, does not sneak into other solvent impurity, has reduced the generation of polluting.
(2) processing unit of the present invention is simple, energy consumption is little, cost is low, and the reaction of especially whole technique is quick, and impurity is few, and the product purity that distillation obtains is high, and content is greater than 99.5%, and yield reaches more than 95%, good in economic efficiency, is easy to suitability for industrialized production.
Embodiment
Below in conjunction with embodiment, the present invention will be further described.
Embodiment 1
In reaction flask, add 50g trimesic acid, 0.05g catalyzer, then add 125g sulfur oxychloride, stir, be heated to 60 ℃, insulation reaction 14 hours, is warming up to 90 ℃, insulated and stirred is 1 hour again, then be distilled to 120 ℃ and remove sulfur oxychloride, then underpressure distillation (pressure is-0.095MPa that temperature is 180 ℃) obtains product 60.71g, chromatogram content is 99.67%, and yield is 96.04%.
Embodiment 2
In reaction flask, add 50g trimesic acid, 1.5g catalyzer, adds 283g sulfur oxychloride, stir, be heated to 65 ℃, insulation reaction 12 hours, is warming up to 90 ℃, insulated and stirred is 1 hour again, then be distilled to 120 ℃ and remove sulfur oxychloride, then underpressure distillation (pressure is-0.095MPa that temperature is 172 ℃) obtains product 61.62g, chromatogram content is 99.58%, and yield is 97.48%.
Embodiment 3
In reaction flask, add 100g trimesic acid, 0.2g catalyzer, adds 200g sulfur oxychloride, stir, be heated to 70 ℃, insulation reaction 10 hours, is warming up to 92 ℃, insulated and stirred is 1 hour again, then be distilled to 120 ℃ and remove sulfur oxychloride, then underpressure distillation obtains (pressure is-0.095MPa that temperature is 183 ℃) to product 121.32g, chromatogram content is 99.74%, and yield is 95.96%.
Embodiment 4
In reaction flask, add 100g trimesic acid, 0.3g catalyzer, adds 200g sulfur oxychloride, stir, be heated to 70 ℃, insulation reaction 5 hours, is warming up to 90 ℃, insulated and stirred is 1 hour again, then be distilled to 120 ℃ and remove sulfur oxychloride, then underpressure distillation (pressure is-0.095MPa that temperature is 175 ℃) obtains product 120.63g, chromatogram content is 99.81%, and yield is 95.41%.
Embodiment 5
In reaction flask, add 200g trimesic acid, 1g catalyzer, adds 397g sulfur oxychloride, stir, be heated to 80 ℃, insulation reaction 10 hours, is warming up to 90 ℃, insulated and stirred is 1 hour again, then be distilled to 120 ℃ and remove sulfur oxychloride, then underpressure distillation (pressure is-0.095MPa that temperature is 178 ℃) obtains product 246.33g, chromatogram content is 99.86%, and yield is 97.42%.
Claims (8)
1. a synthetic method for pyromellitic trimethylsilyl chloride, is characterized in that: comprise the following steps:
(1) by trimesic acid and sulfur oxychloride under catalyst action, reaction;
(2) reacted rear first distillation and removed sulfur oxychloride, then underpressure distillation obtains pyromellitic trimethylsilyl chloride.
2. the synthetic method of pyromellitic trimethylsilyl chloride according to claim 1, is characterized in that: in step (1), temperature of reaction is 60～80 ℃, and the time is 5～15 hours.
3. the synthetic method of pyromellitic trimethylsilyl chloride according to claim 1, is characterized in that: in step (1), the mol ratio of trimesic acid and sulfur oxychloride is 1:3.5～1:10.
4. the synthetic method of pyromellitic trimethylsilyl chloride according to claim 1, is characterized in that: in step (1), catalyzer is organic amine or quaternary ammonium salt phase transfer catalyst.
5. the synthetic method of pyromellitic trimethylsilyl chloride according to claim 4, it is characterized in that: in step (1), catalyzer is triphenylphosphine oxide, N, the mixture of one or more in dinethylformamide, N,N-dimethylacetamide, benzyl triethyl ammonium ammonium halide or benzyl tributyl ammonium halide.
6. the synthetic method of pyromellitic trimethylsilyl chloride according to claim 1, is characterized in that: catalyst levels is 0.1%～3% of trimesic acid quality.
7. the synthetic method of pyromellitic trimethylsilyl chloride according to claim 1, is characterized in that: in step (2), distillation temperature is 120 ℃.
8. according to the synthetic method of the pyromellitic trimethylsilyl chloride described in claim 1 or 7, it is characterized in that: in step (2), underpressure distillation pressure is-0.095MPa, and temperature is 172～183 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310646526.2A CN103641710A (en) | 2013-12-04 | 2013-12-04 | Synthesis method for trimesoyl chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310646526.2A CN103641710A (en) | 2013-12-04 | 2013-12-04 | Synthesis method for trimesoyl chloride |
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| CN103641710A true CN103641710A (en) | 2014-03-19 |
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| CN201310646526.2A Pending CN103641710A (en) | 2013-12-04 | 2013-12-04 | Synthesis method for trimesoyl chloride |
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| CN (1) | CN103641710A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348049A (en) * | 2015-12-14 | 2016-02-24 | 山东凯盛新材料有限公司 | Method for compounding 1-(2-Chloroethoxy)propane |
| CN105523902A (en) * | 2015-12-14 | 2016-04-27 | 山东凯盛新材料有限公司 | Preparation method of 1-(2-chloroethoxy)propane |
| CN105523901A (en) * | 2015-12-14 | 2016-04-27 | 山东凯盛新材料有限公司 | Synthetic method of 1-(2-chloroethoxy)propane |
| CN109553527A (en) * | 2018-12-07 | 2019-04-02 | 杭州盛弗泰新材料科技有限公司 | A kind of preparation method of pyromellitic trimethylsilyl chloride |
| CN109610157A (en) * | 2018-09-18 | 2019-04-12 | 杭州创屹机电科技有限公司 | A kind of preparation method of antibacterial and deodorant hemp fiber base cloth for artificial leather |
| CN115505460A (en) * | 2022-10-10 | 2022-12-23 | 深圳市中兴恒熙环保有限公司 | Method for extracting waste grease from kitchen waste |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348049A (en) * | 2015-12-14 | 2016-02-24 | 山东凯盛新材料有限公司 | Method for compounding 1-(2-Chloroethoxy)propane |
| CN105523902A (en) * | 2015-12-14 | 2016-04-27 | 山东凯盛新材料有限公司 | Preparation method of 1-(2-chloroethoxy)propane |
| CN105523901A (en) * | 2015-12-14 | 2016-04-27 | 山东凯盛新材料有限公司 | Synthetic method of 1-(2-chloroethoxy)propane |
| CN109610157A (en) * | 2018-09-18 | 2019-04-12 | 杭州创屹机电科技有限公司 | A kind of preparation method of antibacterial and deodorant hemp fiber base cloth for artificial leather |
| CN109610157B (en) * | 2018-09-18 | 2021-04-20 | 杭州创屹机电科技有限公司 | Preparation method of antibacterial and deodorant fibrilia primary backing cloth for artificial leather |
| CN109553527A (en) * | 2018-12-07 | 2019-04-02 | 杭州盛弗泰新材料科技有限公司 | A kind of preparation method of pyromellitic trimethylsilyl chloride |
| CN115505460A (en) * | 2022-10-10 | 2022-12-23 | 深圳市中兴恒熙环保有限公司 | Method for extracting waste grease from kitchen waste |
| CN115505460B (en) * | 2022-10-10 | 2023-08-15 | 深圳市中兴恒熙环保有限公司 | Method for extracting waste grease from kitchen waste |
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Address after: Double Yang Zichuan District 255190 Shandong city of Zibo Province Applicant after: SHANDONG KAISHENG NEW MATERIALS CO., LTD. Address before: Double Yang Zichuan District 255190 Shandong city of Zibo Province Applicant before: Shandong Kaisheng New Materials Co.,Ltd. |
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Application publication date: 20140319 |