CN105566388A - Method for synthesizing trimethylphosphine oxide - Google Patents
Method for synthesizing trimethylphosphine oxide Download PDFInfo
- Publication number
- CN105566388A CN105566388A CN201510969228.6A CN201510969228A CN105566388A CN 105566388 A CN105566388 A CN 105566388A CN 201510969228 A CN201510969228 A CN 201510969228A CN 105566388 A CN105566388 A CN 105566388A
- Authority
- CN
- China
- Prior art keywords
- tmpo
- trimethylphosphine oxide
- mixed solvent
- chloride
- add
- 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.)
- Granted
Links
- LRMLWYXJORUTBG-UHFFFAOYSA-N dimethylphosphorylmethane Chemical compound CP(C)(C)=O LRMLWYXJORUTBG-UHFFFAOYSA-N 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title abstract description 15
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 86
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 63
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 238000003756 stirring Methods 0.000 claims abstract description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011777 magnesium Substances 0.000 claims abstract description 9
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 9
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 8
- 239000012046 mixed solvent Substances 0.000 claims description 37
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000010189 synthetic method Methods 0.000 claims description 13
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 12
- 229960003280 cupric chloride Drugs 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- 238000011049 filling Methods 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 3
- 229940050176 methyl chloride Drugs 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000001816 cooling Methods 0.000 abstract description 3
- 239000003999 initiator Substances 0.000 abstract description 3
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 239000011259 mixed solution Substances 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5304—Acyclic saturated phosphine oxides or thioxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
The invention discloses a method for synthesizing trimethylphosphine oxide and belongs to the field of compound preparation. The method includes: under nitrogen protection, allowing chloromethane and magnesium chips to react in the mixed solution of toluene and tetrahydrofuran by using bromoethane as initiator so as to obtain methylmagnesium chloride; directly adding trichlorine into the methylmagnesium chloride, which needs not to be purified, after cooling, stirring under low temperature to allow for reaction, extracting after the reaction is completed, and performing vacuum refinery distillation and cooling crystallization to obtain the trimethylphosphine oxide. The method has the advantages that the purity of the obtained trimethylphosphine oxide is above 99.5%, the yield of the trimethylphosphine oxide reaches 95%, and the solvent used by the method is easy to recycle.
Description
Technical field
The present invention relates to compou nd synthesis field, particularly a kind of synthetic method of trimethylphosphine oxide (TMPO).
Background technology
Trimethylphosphine oxide (TMPO) is very important midbody compound, and its application widely.Prepare the method long reaction time of trimethylphosphine oxide (TMPO), solvent not easily recycling at present, and productive rate is lower, product purity is low, in addition, use ether for solvent security poor.
Summary of the invention
In order to make up the deficiencies in the prior art, the invention provides a kind of synthetic method of safe and reliable trimethylphosphine oxide (TMPO), the inventive method temperature of reaction is low, the reaction times is short, solvent is easy to reclaim and productive rate is high.
Technical scheme of the present invention is:
A synthetic method for trimethylphosphine oxide (TMPO), comprises step:
1) preparation of methylmagnesium-chloride
Under protection of inert gas, mixed solvent 30-60mL is added in the reaction vessel filling 1mol magnesium chips, and add monobromethane 0.5-1.5mL, after being heated to 40-60 DEG C, 0.2-0.3mol methyl chloride is slowly passed in reaction vessel, logical complete, start and stir and continue to add mixed solvent 400-500mL; Keep 45-50 DEG C, continue to pass into 0.68-0.82mol methyl chloride, after having led to, at 40-60 DEG C, stir 1-3 hour, obtain methylmagnesium-chloride; Described mixed solvent is the mixed solvent of toluene and tetrahydrofuran (THF), and the volume ratio of toluene and tetrahydrofuran (THF) is 1:1-3:1;
2) preparation of trimethylphosphine oxide (TMPO)
When step 1) gained reaction solution is cooled to 0-10 DEG C, add 1-3g anhydrous cupric chloride, then slowly instill 0.3-0.35mol phosphorus oxychloride, drip off rear stirring 1-3 hour, then add 150-250mL water and 7-13mL massfraction is the hydrochloric acid of 35%, leave standstill after 1-3 hour, separate magnesium chloride water liquid, oil reservoir underpressure distillation, when most of liquid is distilled out of, decrease temperature crystalline, filtration drying obtains trimethylphosphine oxide (TMPO).
Preferably, in described mixed solvent, the volume ratio of toluene and tetrahydrofuran (THF) is 2:1.
Preferably, described rare gas element is nitrogen.Using nitrogen as protection gas, cost is low and security is high.
Preferably, step 2) in, in time steaming the liquid of 3/4-4/5, decrease temperature crystalline.Now decrease temperature crystalline, separate out product at most, and product purity is the highest.
The invention discloses a kind of synthetic method of trimethylphosphine oxide (TMPO), belong to field of compound preparation.First the present invention by methyl chloride and magnesium chips under nitrogen protection, is that initiator for reaction obtains methylmagnesium-chloride with monobromethane in toluene and tetrahydrofuran (THF) mixed solvent; This step products therefrom, without the need to purifying, after cooling, adds trichlorine phosphine oxide directly in above-mentioned steps gains, low temperature reacts, and reacts complete, extraction, oil reservoir rectification under vacuum, decrease temperature crystalline obtain trimethylphosphine oxide (TMPO) product, and purity is more than 99.5%, and yield reaches 95%; And solvent for use of the present invention is easy to recycle.
Beneficial effect of the present invention is:
1, in building-up process of the present invention, step 1) reaction is complete, does not need through purification process, directly adds trichlorine phosphine oxide, enter step 2), reduce purification step, increase yield.
2, the present invention adopts the mixed solvent of toluene and tetrahydrofuran (THF), and both volume ratios are 1:1-3:1, uses this mixed solvent, and reaction conditions is gentle, and yield is high, and this mixed solvent is easy to recycling.
3, using monobromethane as initiator, consumption is few, and velocity of initiation is fast.
4, mixed solvent adds in batches, improves yield largely, and the yield of the inventive method trimethylphosphine oxide (TMPO) reaches 95%.
5, purification of products method is simple, and product purity is up to 99.5%.
Embodiment
Embodiment 1
A synthetic method for trimethylphosphine oxide (TMPO), comprises step:
1) preparation of methylmagnesium-chloride
Under nitrogen protection, in the reaction vessel filling 1mol magnesium chips, add mixed solvent 50mL, and add monobromethane 1mL, after being heated to 50 DEG C, in reaction vessel, slowly pass into 15g methyl chloride, logically to finish, start and stir and continue to add mixed solvent 450mL; Keep 45-50 DEG C, continue to pass into 35g methyl chloride, after having led to, stir 2 hours at 50 DEG C, obtain methylmagnesium-chloride; Described mixed solvent is the mixed solvent of toluene and tetrahydrofuran (THF), and the volume ratio of toluene and tetrahydrofuran (THF) is 2:1;
2) preparation of trimethylphosphine oxide (TMPO)
When step 1) gained reaction solution is cooled to 5 DEG C, add 2g anhydrous cupric chloride, then slowly instill 51g phosphorus oxychloride, drip off rear stirring 2 hours (keeping temperature 5 DEG C in dropping process), then add 200mL water and 10mL massfraction is the hydrochloric acid of 35%, leave standstill after 2 hours, separate magnesium chloride water liquid, oil reservoir underpressure distillation, when 4/5 liquid is distilled out of, decrease temperature crystalline, filtration drying obtains 29.1g trimethylphosphine oxide (TMPO), productive rate is 95.0%, and purity is 99.5%.
Embodiment 2
1) preparation of methylmagnesium-chloride
Under nitrogen protection, in the reaction vessel filling 1mol magnesium chips, add mixed solvent 50mL, and add monobromethane 1mL, after being heated to 50 DEG C, in reaction vessel, slowly pass into 15g methyl chloride, logically to finish, start and stir and continue to add mixed solvent 450mL; Keep 45-50 DEG C, continue to pass into 35g methyl chloride, after having led to, stir 2 hours at 50 DEG C, obtain methylmagnesium-chloride; Described mixed solvent is the mixed solvent of toluene and tetrahydrofuran (THF), and the volume ratio of toluene and tetrahydrofuran (THF) is 2:1;
2) preparation of trimethylphosphine oxide (TMPO)
When step 1) gained reaction solution is cooled to 5 DEG C, add 2g anhydrous cupric chloride, then slowly instill 51g phosphorus oxychloride, drip off rear stirring 2 hours (keeping temperature 5 DEG C in dropping process), then add 200mL water and 10mL massfraction is the hydrochloric acid of 35%, leave standstill after 2 hours, separate magnesium chloride water liquid, oil reservoir underpressure distillation, when 3/4 liquid is distilled out of, decrease temperature crystalline, filtration drying obtains 29.0g trimethylphosphine oxide (TMPO), productive rate is 94.7%, and purity is 99.5%.
Embodiment 3
A synthetic method for trimethylphosphine oxide (TMPO), comprises step:
1) preparation of methylmagnesium-chloride
Under nitrogen protection, in the reaction vessel filling 1mol magnesium chips, add mixed solvent 50mL, and add monobromethane 1mL, after being heated to 50 DEG C, in reaction vessel, slowly pass into 15g methyl chloride, logically to finish, start and stir and continue to add mixed solvent 450mL; Keep 45-50 DEG C, continue to pass into 35g methyl chloride, after having led to, stir 2 hours at 50 DEG C, obtain methylmagnesium-chloride; Described mixed solvent is the mixed solvent of toluene and tetrahydrofuran (THF), and the volume ratio of toluene and tetrahydrofuran (THF) is 2:1;
2) preparation of trimethylphosphine oxide (TMPO)
When step 1) gained reaction solution is cooled to 5 DEG C, add 2g anhydrous cupric chloride, then slowly instill 51g phosphorus oxychloride, drip off rear stirring 2 hours (keeping temperature 5 DEG C in dropping process), then add 200mL water and 10mL massfraction is the hydrochloric acid of 35%, leave standstill after 2 hours, separate magnesium chloride water liquid, oil reservoir underpressure distillation, when 2/3 liquid is distilled out of, decrease temperature crystalline, filtration drying obtains 28.3g trimethylphosphine oxide (TMPO), productive rate is 92.3%, and purity is 99.1%.
Embodiment 4
A synthetic method for trimethylphosphine oxide (TMPO), comprises step:
1) preparation of methylmagnesium-chloride
Under nitrogen protection, in the reaction vessel filling 1mol magnesium chips, add mixed solvent 50mL, and add monobromethane 0.5mL, after being heated to 50 DEG C, in reaction vessel, slowly pass into 12g methyl chloride, logically to finish, start and stir and continue to add mixed solvent 500mL; Keep 45-50 DEG C, continue to pass into 38g methyl chloride, after having led to, stir 3 hours at 43 DEG C, obtain methylmagnesium-chloride; Described mixed solvent is the mixed solvent of toluene and tetrahydrofuran (THF), and the volume ratio of toluene and tetrahydrofuran (THF) is 3:1;
2) preparation of trimethylphosphine oxide (TMPO)
When step 1) gained reaction solution is cooled to 0 DEG C, add 2.5g anhydrous cupric chloride, then slowly instill 52g phosphorus oxychloride, drip off rear stirring 2 hours (keeping temperature 0 DEG C in dropping process), then add 150mL water and 8mL massfraction is the hydrochloric acid of 35%, leave standstill after 2 hours, separate magnesium chloride water liquid, oil reservoir underpressure distillation, when 4/5 liquid is distilled out of, decrease temperature crystalline, filtration drying obtains 28.7g trimethylphosphine oxide (TMPO), productive rate is 93.7%, and purity is 99.5%.
Embodiment 5
A synthetic method for trimethylphosphine oxide (TMPO), is characterized in that, comprises step:
1) preparation of methylmagnesium-chloride
Under nitrogen protection, in the reaction vessel filling 1mol magnesium chips, add mixed solvent 40mL, and add monobromethane 1.5mL, after being heated to 60 DEG C, in reaction vessel, slowly pass into 15g methyl chloride, logically to finish, start and stir and continue to add mixed solvent 400mL; Keep 45-50 DEG C, continue to pass into 36g methyl chloride, after having led to, stir 2 hours at 48 DEG C, obtain methylmagnesium-chloride; Described mixed solvent is the mixed solvent of toluene and tetrahydrofuran (THF), and the volume ratio of toluene and tetrahydrofuran (THF) is 2:1;
2) preparation of trimethylphosphine oxide (TMPO)
When step 1) gained reaction solution is cooled to 8 DEG C, add 1.8g anhydrous cupric chloride, then slowly instill 52g phosphorus oxychloride, drip off rear stirring 2 hours (keeping temperature 8 DEG C in dropping process), then add 180mL water and 12mL massfraction is the hydrochloric acid of 35%, leave standstill after 2 hours, separate magnesium chloride water liquid, oil reservoir underpressure distillation, when 4/5 liquid is distilled out of, decrease temperature crystalline, filtration drying obtains 28.88g trimethylphosphine oxide (TMPO), productive rate is 94.3%, and purity is 99.5%.
Comparative example 1
Only be with the difference of embodiment 1: the mixed solvent of toluene and tetrahydrofuran (THF) is replaced with simple tetrahydrofuran (THF) as solvent.This comparative example obtains trimethylphosphine oxide (TMPO) 24.8g, and purity is 96.5%, and yield is 81.2%.
Comparative example 2
Only be with the difference of embodiment 1: the mixed solvent of toluene and tetrahydrofuran (THF) is replaced with simple ether as solvent.This comparative example obtains trimethylphosphine oxide (TMPO) 24.1g, and purity is 95.7%, and yield is 78.7%.
Comparative example 3
Only be with the difference of embodiment 1: do not use catalyzer anhydrous cupric chloride; This comparative example obtains trimethylphosphine oxide (TMPO) 18.1g, and purity is 95.2%, and yield is 59.1%.
Claims (4)
1. a synthetic method for trimethylphosphine oxide (TMPO), is characterized in that, comprises step:
1) preparation of methylmagnesium-chloride
Under protection of inert gas, mixed solvent 30-60mL is added in the reaction vessel filling 1mol magnesium chips, and add monobromethane 0.5-1.5mL, after being heated to 40-60 DEG C, 0.2-0.3mol methyl chloride is slowly passed in reaction vessel, logical complete, start and stir and continue to add mixed solvent 400-500mL; Keep 45-50 DEG C, continue to pass into 0.68-0.82mol methyl chloride, after having led to, at 40-60 DEG C, stir 1-3 hour, obtain methylmagnesium-chloride; Described mixed solvent is the mixed solvent of toluene and tetrahydrofuran (THF), and the volume ratio of toluene and tetrahydrofuran (THF) is 1:1-3:1;
2) preparation of trimethylphosphine oxide (TMPO)
When step 1) gained reaction solution is cooled to 0-10 DEG C, add 1-3g anhydrous cupric chloride, then slowly instill 0.3-0.35mol phosphorus oxychloride, drip off rear stirring 1-3 hour, then add 150-250mL water and 7-13mL massfraction is the hydrochloric acid of 35%, leave standstill after 1-3 hour, separate magnesium chloride water liquid, oil reservoir underpressure distillation, when most of liquid is distilled out of, decrease temperature crystalline, filtration drying obtains trimethylphosphine oxide (TMPO).
2. the synthetic method of trimethylphosphine oxide (TMPO) as claimed in claim 1, it is characterized in that: in described mixed solvent, the volume ratio of toluene and tetrahydrofuran (THF) is 2:1.
3. the synthetic method of trimethylphosphine oxide (TMPO) as claimed in claim 1, is characterized in that: described rare gas element is nitrogen.
4. the synthetic method of trimethylphosphine oxide (TMPO) as described in any one of claim 1-3, is characterized in that: step 2) in, in time steaming the liquid of 3/4-4/5, decrease temperature crystalline.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510969228.6A CN105566388B (en) | 2015-12-22 | 2015-12-22 | A kind of synthetic method of trimethylphosphine oxide (TMPO) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510969228.6A CN105566388B (en) | 2015-12-22 | 2015-12-22 | A kind of synthetic method of trimethylphosphine oxide (TMPO) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105566388A true CN105566388A (en) | 2016-05-11 |
| CN105566388B CN105566388B (en) | 2017-12-19 |
Family
ID=55877075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510969228.6A Active CN105566388B (en) | 2015-12-22 | 2015-12-22 | A kind of synthetic method of trimethylphosphine oxide (TMPO) |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105566388B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000069866A1 (en) * | 1999-05-19 | 2000-11-23 | Cytec Technology Corp. | Preparation of alkylarylphosphines or their oxides or sulfides |
| CN101863922A (en) * | 2010-06-04 | 2010-10-20 | 天津师范大学 | Preparation method of polyether aromatic phosphine oxide midbody monomer with three functional groups |
| CN103159796A (en) * | 2011-12-12 | 2013-06-19 | 深圳市有为化学技术有限公司 | Preparation method of acyl phosphine oxide compound |
| CN103788129A (en) * | 2014-01-20 | 2014-05-14 | 清华大学 | Preparation method of trialkyl phosphine oxide |
-
2015
- 2015-12-22 CN CN201510969228.6A patent/CN105566388B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000069866A1 (en) * | 1999-05-19 | 2000-11-23 | Cytec Technology Corp. | Preparation of alkylarylphosphines or their oxides or sulfides |
| CN101863922A (en) * | 2010-06-04 | 2010-10-20 | 天津师范大学 | Preparation method of polyether aromatic phosphine oxide midbody monomer with three functional groups |
| CN103159796A (en) * | 2011-12-12 | 2013-06-19 | 深圳市有为化学技术有限公司 | Preparation method of acyl phosphine oxide compound |
| CN103788129A (en) * | 2014-01-20 | 2014-05-14 | 清华大学 | Preparation method of trialkyl phosphine oxide |
Non-Patent Citations (1)
| Title |
|---|
| 张章等: "有机磷萃取剂的合成研究进展", 《湿法冶金》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105566388B (en) | 2017-12-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103951582A (en) | Preparation method of acetoacetanilide compound | |
| CN103524345A (en) | Product separation process for preparing methyl acrylate from methyl acetate | |
| CN104910178A (en) | Method for preparing piperacillin acid | |
| CN101805366A (en) | Method for preparing tri(3-trimethoxysilylpropyl) isocyanurate | |
| CN101696191B (en) | Purifying method of N-vinyl-Epsilon-caprolactam | |
| CN111393331B (en) | Preparation method of glycocyamine | |
| CN1680374A (en) | Novel synthesis and crystallization of piperazine ring-containing compounds | |
| CN103483577B (en) | A kind of preparation method of glycidyl capped allyl alcohol polyethenoxy ether | |
| CN103664866A (en) | Method for purifying glycolide | |
| CN105440012A (en) | Lenalidomide and lenalidomide intermediate preparation method | |
| CN105566388A (en) | Method for synthesizing trimethylphosphine oxide | |
| CN109232184B (en) | Method for improving optical purity of L-isopulegol through chiral resolution | |
| CN108752184B (en) | Preparation method of SGLT2 inhibitor intermediate | |
| CN104529746B (en) | A kind of method of catalyst compounded synthesis of dimmer acid | |
| CN113603602B (en) | Method for preparing beta-aminopropionic acid with high selectivity | |
| CN102718654A (en) | Preparation method of a-cyclopentyl methyl mandelate | |
| CN104277027A (en) | Preparation method of (R)-propylene carbonate | |
| CN111072450B (en) | Synthesis method of allyl alcohol derivative | |
| CN107602408B (en) | Synthesis method of acetamino diethyl malonate | |
| CN105541611A (en) | Method for preparing aceto acetoxy ethyl methacrylate | |
| CN101781212B (en) | Method for synthesizing 2-hydroxymethyl acrylate compound | |
| CN107162983B (en) | Synthesis and refining method of methimazole | |
| CN111303045A (en) | Production process of 2-ethoxy-4, 6-difluoropyrimidine | |
| CN103483283A (en) | Synthesis method for antioxidant 1790 | |
| CN117229266B (en) | Method for synthesizing ramosetron racemate and salt thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |