CN115677752A - Safe and efficient ethylene silicon synthesis method - Google Patents
Safe and efficient ethylene silicon synthesis method Download PDFInfo
- Publication number
- CN115677752A CN115677752A CN202210813793.3A CN202210813793A CN115677752A CN 115677752 A CN115677752 A CN 115677752A CN 202210813793 A CN202210813793 A CN 202210813793A CN 115677752 A CN115677752 A CN 115677752A
- Authority
- CN
- China
- Prior art keywords
- chloroethyltrichlorosilane
- solvent
- methoxyethanol
- ammonia gas
- ethylene silicon
- 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.)
- Pending
Links
- ZYJKUXGOCSWXQO-UHFFFAOYSA-N ethene;silicon Chemical compound [Si].C=C ZYJKUXGOCSWXQO-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000001308 synthesis method Methods 0.000 title claims abstract description 9
- FLPXNJHYVOVLSD-UHFFFAOYSA-N trichloro(2-chloroethyl)silane Chemical compound ClCC[Si](Cl)(Cl)Cl FLPXNJHYVOVLSD-UHFFFAOYSA-N 0.000 claims abstract description 35
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 239000000047 product Substances 0.000 claims abstract description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000706 filtrate Substances 0.000 claims abstract description 20
- 239000000725 suspension Substances 0.000 claims abstract description 20
- 238000001035 drying Methods 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 13
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- 239000012188 paraffin wax Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 238000003786 synthesis reaction Methods 0.000 abstract description 11
- 230000015572 biosynthetic process Effects 0.000 abstract description 10
- 239000000463 material Substances 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 4
- 239000011230 binding agent Substances 0.000 abstract description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 239000007767 bonding agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- ARLJCLKHRZGWGL-UHFFFAOYSA-N ethenylsilicon Chemical compound [Si]C=C ARLJCLKHRZGWGL-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- -1 tertiary amine quaternary ammonium salt Chemical class 0.000 description 1
Abstract
The invention discloses a safe and efficient ethylene silicon synthesis method, which comprises the steps of adding chloroethyl trichlorosilane A and methoxy ethanol B into a solvent S at normal temperature, introducing ammonia gas C, and stirring for 5-20 hours to obtain a white suspension product D; the mol ratio of the chloroethyltrichlorosilane A to the methoxyethanol B is 1; the mol ratio of the chloroethyltrichlorosilane A to the ammonia gas C is 1; step S2: standing the white suspension product D, filtering, washing with a solvent S, and collecting filtrate; and distilling the collected filtrate under reduced pressure to remove the solvent S, and finally drying under reduced pressure to obtain the ethylene silicon product E. The invention takes chloroethyl trichlorosilane and methoxyethanol as reaction bottom materials and ammonia gas as acid-binding agent, can realize the high-efficiency and high-yield synthesis of the ethylene silicon with the yield of more than 85 percent, simultaneously solves the problems of low synthesis yield or difficult separation of the current ethylene silicon, and is convenient and easy to separate and purify the ethylene silicon.
Description
Technical Field
The invention belongs to the technical field of preparation of agricultural medicaments, and relates to a safe and efficient ethylene silicon synthesis method.
Background
As is well known, ethylene silicon is a plant fruit ripener, which can realize the ripening of plant fruits by releasing ethylene, and with the trend of agricultural modernization, ethylene silicon is an agricultural medicament with huge economic use value. However, the ethylene silicon reagent has no mass industrial production at home, needs to be imported from abroad, and fundamentally has no practical industrial synthesis technology related to ethylene silicon at home. From the viewpoint of chemical synthesis, the synthesis method of vinyl silicon is available in many ways, and the most direct method is direct synthesis by using chloroethyl trichlorosilane and methoxyethanol as raw materials, but the method has low yield which is lower than 50%, and the synthesis process in the way can be accompanied with spontaneous release of ethylene and has the possibility of explosion, so the method has no practical industrial use value. In addition, there is a report in the literature that tertiary amine is introduced as an acid binder in the above reaction, and the yield of the reaction can be greatly improved by the improvement, and the safety hazard of ethylene release can be avoided, but the disadvantage of difficulty in separating tertiary amine and tertiary amine quaternary ammonium salt still exists, so that a green and safe synthesis process with high yield and difficulty in separating is required to be sought.
Disclosure of Invention
The invention aims to provide a safe and efficient ethylene silicon synthesis method aiming at the defects of the prior art.
The ethylene silicon synthesis method of the invention specifically comprises the following steps:
step S1: at normal temperature, adding chloroethyl trichlorosilane A and methoxyethanol B into a solvent S, introducing ammonia gas C, and stirring for 5-20 hours to obtain a white suspension product D;
step S2: standing the white suspension product D, filtering, washing with a solvent S, and collecting filtrate; and distilling the collected filtrate under reduced pressure to remove the solvent S, and finally drying under reduced pressure to obtain the ethylene silicon product E.
Preferably, the molar ratio of the chloroethyltrichlorosilane A to the methoxyethanol B is 1; preferably 1; more preferably 1.
Preferably, the molar ratio of the chloroethyltrichlorosilane A to the ammonia gas C is 1; preferably 1; more preferably 1.
Preferably, the weight ratio of the reaction materials (chloroethyltrichlorosilane A and methoxyethanol B) to the solvent S is 0.4-0.8: 1, preferably 0.5 to 0.6:1.
preferably, the solvent S is one or a mixture of benzene, toluene, xylene, pentane, hexane, paraffin and cyclohexane.
The invention has the beneficial effects that:
the invention takes chloroethyl trichlorosilane and methoxy ethanol as reaction bottom materials and ammonia gas as acid bonding agent, can realize the synthesis of ethylene silicon with high efficiency and high yield, the yield is more than 85 percent, simultaneously solves the problems of low synthesis yield or difficult separation of the current ethylene silicon, and the separation and purification of ethylene silicon are very convenient, simple and easy.
Detailed Description
As described above, in view of the deficiencies of the prior art, the present inventors have long studied and extensively practiced to provide the technical solutions of the present invention, which are mainly based on at least: the invention takes chloroethyl trichlorosilane and methoxy ethanol as reaction bottom materials and ammonia gas as acid bonding agent, can realize the synthesis of ethylene silicon with high efficiency and high yield, the yield is more than 85 percent, and simultaneously solves the problems of low synthesis yield or difficult separation of the current ethylene silicon.
The invention provides a safe and efficient ethylene silicon synthesis method, which comprises the following steps:
step S1: at normal temperature, adding chloroethyl trichlorosilane A and methoxyethanol B into a solvent S, introducing ammonia gas C, and stirring for 5-20 hours to obtain a white suspension product D;
step S2: standing the white suspension product D, filtering, washing with a solvent S, and collecting filtrate; and distilling the collected filtrate under reduced pressure to remove the solvent S, and finally drying under reduced pressure to obtain the ethylene silicon product E.
Preferably, the molar ratio of the chloroethyltrichlorosilane A to the methoxyethanol B is 1; preferably 1; more preferably 1;
preferably, the molar ratio of the chloroethyltrichlorosilane A to the ammonia gas C is 1; preferably 1; more preferably 1;
preferably, the weight ratio of the reaction materials (chloroethyltrichlorosilane A and methoxyethanol B) to the solvent S is 0.4-0.8: 1, preferably 0.5 to 0.6:1.
preferably, the solvent S is one or a mixture of benzene, toluene, xylene, pentane, hexane, paraffin and cyclohexane.
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail below with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and do not limit the invention.
In addition, the technical features involved in the embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
Example 1
150ml of toluene solution was added to the reactor at room temperature, 30g of chloroethyltrichlorosilane (0.15 mol) was added, 38g of methoxyethanol (0.5 mol) was added, 8.5g of ammonia gas (0.5 mol) was introduced, and the reaction was stirred for 15 hours to obtain a white suspension product.
Standing the above suspension, filtering, washing with toluene for three times, and collecting the filtrate. Distilling the collected filtrate under reduced pressure at 40-50 deg.C and 13-15 mmHg to remove toluene as solvent, and drying at 60 deg.C and 0.02-0.03 mmHg under reduced pressure to obtain 44g of ethylene silicon product with purity of about 98.7%.
Example 2
150ml of a hexane solution was added to a reactor at room temperature, 30g of chloroethyltrichlorosilane (0.15 mol) was added thereto, 36g of methoxyethanol (0.47 mol) was added thereto, 8.5g of ammonia gas (0.5 mol) was introduced thereinto, and the reaction was stirred for 15 hours to obtain a white suspension as a product.
The suspension was allowed to stand, filtered, washed three times with hexane and the filtrate was collected. Distilling the collected filtrate under reduced pressure at 40-50 deg.C and 13-15 mmHg to remove hexane as solvent, and drying under reduced pressure at 60 deg.C and 0.02-0.03 mmHg to obtain 42.7g of ethylene silicon product with purity of 95.8%.
Example 3
At room temperature, adding benzene solution, 0.1mol of chloroethyl trichlorosilane and 0.6mol of methoxyethanol into a reactor, wherein the weight ratio of chloroethyl trichlorosilane A and methoxyethanol B to the benzene solution is 0.4:1, introducing 0.3mol of ammonia gas, and stirring for reaction for 10 hours to obtain a white suspension product.
Standing the suspension, filtering, washing with benzene for three times, and collecting filtrate. Distilling the collected filtrate under reduced pressure at 40-50 deg.C and 13-15 mmHg to remove solvent hexane, and drying under reduced pressure at 60 deg.C and 0.02-0.03 mmHg to obtain the product.
Example 4
At room temperature, adding a xylene solution, 0.1mol of chloroethyl trichlorosilane and 0.4mol of methoxy ethanol into a reactor, wherein the weight ratio of chloroethyl trichlorosilane A to methoxy ethanol B to the xylene solution is 0.8:1, introducing 0.6mol of ammonia gas, and stirring for reaction for 12 hours to obtain a white suspension product.
Standing the suspension, filtering, washing with xylene for three times, and collecting filtrate. Distilling the collected filtrate under reduced pressure at 40-50 deg.C and 13-15 mmHg to remove hexane as solvent, and drying under reduced pressure at 60 deg.C and 0.02-0.03 mmHg to obtain the final product.
Example 5
At room temperature, adding a pentane solution, 0.1mol of chloroethyl trichlorosilane and 0.33mol of methoxyethanol into a reactor, wherein the weight ratio of chloroethyl trichlorosilane A and methoxyethanol B to the pentane solution is 0.5:1, introducing 0.33mol of ammonia gas, and stirring and reacting for 20 hours to obtain a white suspension product.
The suspension was allowed to stand, filtered, washed three times with pentane and the filtrate collected. Distilling the collected filtrate under reduced pressure at 40-50 deg.C and 13-15 mmHg to remove hexane as solvent, and drying under reduced pressure at 60 deg.C and 0.02-0.03 mmHg to obtain 42.7g of vinyl silicon product.
Example 6
At room temperature, adding cyclohexane solution, 0.1mol of chloroethyl trichlorosilane and 0.3mol of methoxy ethanol into a reactor, wherein the weight ratio of chloroethyl trichlorosilane A to methoxy ethanol B to the cyclohexane solution is 0.6: and (1) introducing 0.5mol of ammonia gas, and stirring to react for 5 hours to obtain a white suspension product.
The suspension was allowed to stand, filtered, washed three times with cyclohexane and the filtrate was collected. Distilling the collected filtrate under reduced pressure at 40-50 deg.C and 13-15 mmHg to remove solvent hexane, and drying under reduced pressure at 60 deg.C and 0.02-0.03 mmHg to obtain the product.
Claims (9)
1. A safe and efficient ethylene silicon synthesis method is characterized by comprising the following steps:
step S1: at normal temperature, adding chloroethyl trichlorosilane A and methoxyethanol B into a solvent S, introducing ammonia gas C, and stirring for 5-20 hours to obtain a white suspension product D; the mol ratio of the chloroethyltrichlorosilane A to the methoxyethanol B is 1; the molar ratio of the chloroethyltrichlorosilane A to the ammonia gas C is (1);
step S2: standing the white suspension product D, filtering, washing with a solvent S, and collecting filtrate; and distilling the collected filtrate under reduced pressure to remove the solvent S, and finally drying under reduced pressure to obtain the ethylene silicon product E.
2. The method according to claim 1, wherein the molar ratio of chloroethyltrichlorosilane A to methoxyethanol B in step S1 is 1.
3. The method according to claim 2, wherein the molar ratio of chloroethyltrichlorosilane A to methoxyethanol B in step S1 is 1.
4. The method according to claim 1, wherein the molar ratio of the chloroethyltrichlorosilane A to the ammonia gas C in step S1 is 1.
5. The method according to claim 4, wherein the molar ratio of the chloroethyltrichlorosilane A to the ammonia gas C in step S1 is 1.
6. The method according to claim 5, wherein the molar ratio of chloroethyltrichlorosilane A to ammonia gas C in step S1 is 1.
7. The process according to claim 1, wherein the weight ratio of the total amount of chloroethyltrichlorosilane A and methoxyethanol B in step S1 to solvent S is from 0.4 to 0.8:1.
8. the process according to claim 7, wherein the weight ratio of the total amount of chloroethyltrichlorosilane A and methoxyethanol B in step S1 to solvent S is from 0.5 to 0.6:1.
9. the method according to claim 1, 7 or 8, wherein the solvent S in step S1 is one or more of benzene, toluene, xylene, pentane, hexane, paraffin and cyclohexane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210813793.3A CN115677752A (en) | 2022-07-11 | 2022-07-11 | Safe and efficient ethylene silicon synthesis method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210813793.3A CN115677752A (en) | 2022-07-11 | 2022-07-11 | Safe and efficient ethylene silicon synthesis method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115677752A true CN115677752A (en) | 2023-02-03 |
Family
ID=85060581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210813793.3A Pending CN115677752A (en) | 2022-07-11 | 2022-07-11 | Safe and efficient ethylene silicon synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115677752A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH528209A (en) * | 1970-10-06 | 1972-09-30 | Agripat Sa | Plant-growth regulating agents - contg haloethyl -silane compounds |
| US4111974A (en) * | 1977-01-28 | 1978-09-05 | Ciba-Geigy Corporation | Process for the production of alkoxy-β-halogenoethylsilanes |
| CN102924497A (en) * | 2012-10-09 | 2013-02-13 | 湖北兴发化工集团股份有限公司 | Method for preparing saturated hydrocarbyl alkoxy silane |
| CN105111231A (en) * | 2015-09-09 | 2015-12-02 | 成都硅宝科技股份有限公司 | Alpha-silane coupling agent and application thereof |
| CN105254658A (en) * | 2015-09-15 | 2016-01-20 | 湖北兴发化工集团股份有限公司 | Preparation method for methyl trialkoxy silane |
-
2022
- 2022-07-11 CN CN202210813793.3A patent/CN115677752A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH528209A (en) * | 1970-10-06 | 1972-09-30 | Agripat Sa | Plant-growth regulating agents - contg haloethyl -silane compounds |
| US4111974A (en) * | 1977-01-28 | 1978-09-05 | Ciba-Geigy Corporation | Process for the production of alkoxy-β-halogenoethylsilanes |
| CN102924497A (en) * | 2012-10-09 | 2013-02-13 | 湖北兴发化工集团股份有限公司 | Method for preparing saturated hydrocarbyl alkoxy silane |
| CN105111231A (en) * | 2015-09-09 | 2015-12-02 | 成都硅宝科技股份有限公司 | Alpha-silane coupling agent and application thereof |
| CN105254658A (en) * | 2015-09-15 | 2016-01-20 | 湖北兴发化工集团股份有限公司 | Preparation method for methyl trialkoxy silane |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN113321688B (en) | Bifunctional catalyst and method for preparing cyclic carbonate and polycarbonate by using same in external loop reaction process | |
| CN111004212A (en) | Method for preparing nicotine | |
| CN109096122B (en) | Process for preparing spermidine | |
| CN101538191B (en) | Synthetic method of high-purity propofol | |
| CN108148089B (en) | Preparation method of tetra (dimethylamino) titanium | |
| CN115677752A (en) | Safe and efficient ethylene silicon synthesis method | |
| CN110452269B (en) | Method for preparing tenofovir by using microreactor | |
| CN104530090A (en) | Pyridine derivative preparing method | |
| CN108948117B (en) | Synthetic method of obeticholic acid | |
| CN106831405B (en) | Preparation method of 2, 2-difluoroacetyl fluoride and derivatives thereof | |
| CN111944855B (en) | Method for synthesizing (R) -1- (4- (benzyloxy) -3-nitrophenyl) -2-bromoethanol | |
| CN111217690B (en) | Preparation method of propafenone hydrochloride and intermediate 2' -hydroxy dihydrochalcone thereof | |
| JP4131575B2 (en) | Production method of benzophenone imine | |
| CN107903346B (en) | Binuclear rare earth catalyst, preparation method thereof and polymerization method of syndiotactic polystyrene | |
| CN116273185B (en) | Immobilized bifunctional catalyst and method for preparing cyclic carbonate in outer loop reaction process | |
| CN110339858B (en) | Bi for synthesizing methyl phenyl carbonate2O3-PbO-SBA-15 catalyst, preparation method and application | |
| CN114133412B (en) | Preparation method of chiral 1, 2-bis [ (2-methoxyphenyl) phenylphosphinyl ] ethane | |
| CN111185241B (en) | Metal catalyst and preparation method and application thereof | |
| CN112125846B (en) | Preparation method of 1, 7-di (9-acridinyl) heptane | |
| CN115181093B (en) | Preparation method of Sunvozertinib intermediate | |
| CN115160110B (en) | Method for synthesizing bisphenol Z | |
| CN112694436B (en) | Method for synthesizing arecoline | |
| CN115181060B (en) | Clean production process for producing 2-amino-3-chloro-5-trifluoromethyl pyridine | |
| CN110183355B (en) | Refining method of high-purity o-chloro mandelonitrile | |
| CN110407667B (en) | Preparation method of alkoxy aluminum |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |