CN106317118A - Synthesis method of hexa(4-hydroxyl oxethyl) cyclotriphosphazene - Google Patents
Synthesis method of hexa(4-hydroxyl oxethyl) cyclotriphosphazene Download PDFInfo
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- CN106317118A CN106317118A CN201610698487.4A CN201610698487A CN106317118A CN 106317118 A CN106317118 A CN 106317118A CN 201610698487 A CN201610698487 A CN 201610698487A CN 106317118 A CN106317118 A CN 106317118A
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- ring
- oxethyl
- hydroxyl
- phosphonitrile
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- DZKXDEWNLDOXQH-UHFFFAOYSA-N 1,3,5,2,4,6-triazatriphosphinine Chemical compound N1=PN=PN=P1 DZKXDEWNLDOXQH-UHFFFAOYSA-N 0.000 title abstract 6
- 238000001308 synthesis method Methods 0.000 title abstract 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical compound OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 claims description 27
- 229910052698 phosphorus Inorganic materials 0.000 claims description 20
- 239000011574 phosphorus Substances 0.000 claims description 19
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 16
- 210000005252 bulbus oculi Anatomy 0.000 claims description 16
- 208000035126 Facies Diseases 0.000 claims description 15
- XCJXQCUJXDUNDN-UHFFFAOYSA-N chlordene Chemical group C12C=CCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl XCJXQCUJXDUNDN-UHFFFAOYSA-N 0.000 claims description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 10
- 230000006837 decompression Effects 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 10
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 10
- 239000012312 sodium hydride Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 238000010189 synthetic method Methods 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 8
- -1 methoxyl group Chemical group 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 239000012153 distilled water Substances 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 238000010025 steaming Methods 0.000 claims description 2
- 230000001335 demethylating effect Effects 0.000 abstract description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 2
- 239000011734 sodium Substances 0.000 abstract description 2
- 229910052708 sodium Inorganic materials 0.000 abstract description 2
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 238000010791 quenching Methods 0.000 abstract 1
- 230000000171 quenching effect Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000003063 flame retardant Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 4
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical class CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
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- 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 synthesis method of hexa(4-hydroxyl oxethyl) cyclotriphosphazene. The synthesis method comprises the following steps: taking phosphonitrilic chloride trimer as a raw material and reacting the phosphonitrilic chloride trimer and sodium alcoholate to obtain hexa(4-methoxyl oxethyl) cyclotriphosphazene as an intermediate; and reacting the hexa(4-methoxyl oxethyl) cyclotriphosphazene with boron trichloride under the condition of ice bath, after reaction is finished, adding water to carry out quenching reaction, and further treating to obtain the hexa(4-hydroxyl oxethyl) cyclotriphosphazene. The synthesis method of the hexa(4-hydroxyl oxethyl) cyclotriphosphazene has the beneficial effects that demethylating reaction is carried out by the boron trichloride, reaction conditions are gentle, carbonyl and double bonds in molecules are not affected, and demethylating is relatively thorough. The synthesis method is low in cost, simple and convenient to operate and short in reaction time, and the purity and the yield of obtained products are high.
Description
Technical field
The invention belongs to chemosynthesis technical field, particularly relate to the conjunction of a kind of six (4-hydroxyl-oxethyl) ring three phosphonitrile
One-tenth method.
Background technology
Fire retardant be a class for improving the additive of macromolecular material combustibility, of many uses in life.Ring three
Phosphazene derivative is the chemical combination in the molecule obtained after hexachlorocyclotriph,sphazene nucleo philic substitution reaction containing "-P=N-" structure
Thing.As fire retardant, ring three phosphazene derivative has the advantage that chlorine atom is replaced by Halogen group after, without halogen, green
Environmental protection；Rich in two kinds of first ropes of N, P, cooperative flame retardant efficiency is high；Easily functional modification, kind is many.Therefore, ring three phosphazene derivative
As fire retardant, there is good market prospect, be one of the developmental research direction of following fire retardant.
Six (4-hydroxyl-oxethyl) ring three phosphonitrile is a kind of special aliphatic ring three phosphazene derivative, because containing in its structure
There are six activity hydroxies, are usually implemented as heat-resisting, the modifying agent of flame retardant polyurethane material and prepare six arm star polymer
Polyhydroxy initiator.Six (4-hydroxyl-oxethyl) ring three phosphonitrile can obtain with sodium alkoxide substitution reaction with chlordene ring three phosphorus eyeball.Synthesis
Being demethylating reaction in place of reaction key, demethylating reaction has a lot of reagent selective, and 3 aspects should be noted that below: 1) divide
There is sensitive group in son, strong acid, highly basic and high temperature can cause serious side reaction；2) Polymethoxylated compound requires cracking first
Base location and quantity；3) control reacted in building-up process and the yield of target product.Patent CN102766168 reports
Use Boron tribromide to carry out demethylating reaction, six (4-methoxy ethoxy) ring three phosphonitrile demethylation is generated six (4-hydroxyl second
Epoxide) ring three phosphonitrile, but its response time is relatively long, and also product purity and yield are relatively low.
Summary of the invention
The purpose of the present invention is that and overcomes above-mentioned deficiency, it is provided that the synthesis of a kind of six (4-hydroxyl-oxethyl) ring three phosphonitrile
Method and preparation method thereof.
For reaching above-mentioned purpose, the present invention implements according to techniques below scheme:
The synthetic method of a kind of six (4-hydroxyl-oxethyl) ring three phosphonitrile, comprises the following steps:
(1) sodium hydride and oxolane are joined in reaction bulb, drip the most while stirring dissolved with methoxyl group second
The tetrahydrofuran solution of alcohol, reacts 40min at ambient temperature；
(2) under condition of ice bath, it is slowly added to the tetrahydrofuran solution dissolved with chlordene ring three phosphorus eyeball, is 40 ~ 45 DEG C of bars in temperature
20 ~ 23h is reacted under part；
(3) being filtered by the reactant liquor of gained in step (2), obtain filtrate, the oxolane in filtrate is removed in decompression distillation；
(4) add appropriate dichloromethane, and use distilled water wash, until aqueous phase is neutrality, separate organic facies, and steaming of reducing pressure
Evaporate except the dichloromethane in organic facies, obtain six (4-methoxy ethoxy) ring three phosphorus eyeball；
(5) six (4-methoxy ethoxy) ring three phosphonitrile obtained in step (4) is dissolved in appropriate dichloromethane, at ice
Under the conditions of bath, it is slowly added to add the dichloromethane solution of boron chloride, stirs 40 ~ 60min；
(6) it is directly added into appropriate shrend to go out reaction, stands, the water that decompression is distilled off in organic facies, obtain six (4-hydroxyl second
Epoxide) ring three phosphonitrile.
Further, sodium hydride is 1.0:1 with the mol ratio of methyl cellosolve.
Further, methyl cellosolve is 6.5:1 ~ 7.0:1 with the mol ratio of chlordene ring three phosphorus eyeball.
Further, in step (5), the mol ratio of boron chloride and six (4-methoxy ethoxy) ring three phosphonitrile is 1.0:1
~1.8:1。
Compared with prior art, the invention have the benefit that
The present invention uses boron chloride to carry out demethylating reaction, and reaction condition is gentle, does not affect the carbonyl in molecule and double bond, de-
Methyl is the most thorough.This synthetic method low cost, easy and simple to handle, the response time is shorter, and products obtained therefrom purity and yield are higher.
Detailed description of the invention
Below in conjunction with specific embodiment, the invention will be further described, the illustrative examples invented at this and explanation
It is used for explaining the present invention, but not as a limitation of the invention.
Embodiment 1
The synthetic method of a kind of six (4-hydroxyl-oxethyl) ring three phosphonitrile, comprises the following steps: sodium hydride and oxolane are added
Enter in reaction bulb, drip the tetrahydrofuran solution dissolved with methyl cellosolve, sodium hydride and first the most while stirring
The mol ratio of ethoxy-ethanol is 1.0:1, reacts 40min at ambient temperature；Under condition of ice bath, it is slowly added to dissolved with chlordene ring
The tetrahydrofuran solution of three phosphorus eyeballs, methyl cellosolve is 6.5:1 with the mol ratio of chlordene ring three phosphorus eyeball, is 40 DEG C of conditions in temperature
Lower reaction 20h；Being filtered by the reactant liquor of gained, obtain filtrate, the oxolane in filtrate is removed in decompression distillation；Add appropriate
Dichloromethane, and use distilled water wash, until aqueous phase is neutrality, separate organic facies, and distillation of reducing pressure is removed in organic facies
Dichloromethane, obtain six (4-methoxy ethoxy) ring three phosphorus eyeball；By obtained six (4-methoxy ethoxy) ring three phosphorus
Nitrile is dissolved in appropriate dichloromethane, under condition of ice bath, is slowly added to add the dichloromethane solution of boron chloride, tri-chlorination
The mol ratio of boron and six (4-methoxy ethoxy) ring three phosphonitrile is 1.0:1, stirs 60min；It is directly added into appropriate shrend to go out
Reaction, stands, and the water that decompression is distilled off in organic facies obtains six (4-hydroxyl-oxethyl) ring three phosphonitrile.
Embodiment 2
The synthetic method of a kind of six (4-hydroxyl-oxethyl) ring three phosphonitrile, comprises the following steps: sodium hydride and oxolane are added
Enter in reaction bulb, drip the tetrahydrofuran solution dissolved with methyl cellosolve, sodium hydride and first the most while stirring
The mol ratio of ethoxy-ethanol is 1.0:1, reacts 40min at ambient temperature；Under condition of ice bath, it is slowly added to dissolved with chlordene ring
The tetrahydrofuran solution of three phosphorus eyeballs, methyl cellosolve is 7.0:1 with the mol ratio of chlordene ring three phosphorus eyeball, is 42 DEG C of conditions in temperature
Lower reaction 22h；Being filtered by the reactant liquor of gained, obtain filtrate, the oxolane in filtrate is removed in decompression distillation；Add appropriate
Dichloromethane, and use distilled water wash, until aqueous phase is neutrality, separate organic facies, and distillation of reducing pressure is removed in organic facies
Dichloromethane, obtain six (4-methoxy ethoxy) ring three phosphorus eyeball；By obtained six (4-methoxy ethoxy) ring three phosphorus
Nitrile is dissolved in appropriate dichloromethane, under condition of ice bath, is slowly added to add the dichloromethane solution of boron chloride, tri-chlorination
The mol ratio of boron and six (4-methoxy ethoxy) ring three phosphonitrile is 1.5:1, stirs 50min；It is directly added into appropriate shrend to go out
Reaction, stands, and the water that decompression is distilled off in organic facies obtains six (4-hydroxyl-oxethyl) ring three phosphonitrile.
Embodiment 3
The synthetic method of a kind of six (4-hydroxyl-oxethyl) ring three phosphonitrile, comprises the following steps: sodium hydride and oxolane are added
Enter in reaction bulb, drip the tetrahydrofuran solution dissolved with methyl cellosolve, sodium hydride and first the most while stirring
The mol ratio of ethoxy-ethanol is 1.0:1, reacts 40min at ambient temperature；Under condition of ice bath, it is slowly added to dissolved with chlordene ring
The tetrahydrofuran solution of three phosphorus eyeballs, methyl cellosolve is 6.8:1 with the mol ratio of chlordene ring three phosphorus eyeball, is 45 DEG C of conditions in temperature
Lower reaction 20h；Being filtered by the reactant liquor of gained, obtain filtrate, the oxolane in filtrate is removed in decompression distillation；Add appropriate
Dichloromethane, and use distilled water wash, until aqueous phase is neutrality, separate organic facies, and distillation of reducing pressure is removed in organic facies
Dichloromethane, obtain six (4-methoxy ethoxy) ring three phosphorus eyeball；By obtained six (4-methoxy ethoxy) ring three phosphorus
Nitrile is dissolved in appropriate dichloromethane, under condition of ice bath, is slowly added to add the dichloromethane solution of boron chloride, tri-chlorination
The mol ratio of boron and six (4-methoxy ethoxy) ring three phosphonitrile is 1.8:1, stirs 45min；It is directly added into appropriate shrend to go out
Reaction, stands, and the water that decompression is distilled off in organic facies obtains six (4-hydroxyl-oxethyl) ring three phosphonitrile.
Technical scheme is not limited to the restriction of above-mentioned specific embodiment, every does according to technical scheme
The technology deformation gone out, within each falling within protection scope of the present invention.
Claims (4)
1. the synthetic method of one kind six (4-hydroxyl-oxethyl) ring three phosphonitrile, it is characterised in that comprise the following steps:
(1) sodium hydride and oxolane are joined in reaction bulb, drip the most while stirring dissolved with methoxyl group second
The tetrahydrofuran solution of alcohol, reacts 40min at ambient temperature；
(2) under condition of ice bath, it is slowly added to the tetrahydrofuran solution dissolved with chlordene ring three phosphorus eyeball, is 40 ~ 45 DEG C of bars in temperature
20 ~ 23h is reacted under part；
(3) being filtered by the reactant liquor of gained in step (2), obtain filtrate, the oxolane in filtrate is removed in decompression distillation；
(4) add appropriate dichloromethane, and use distilled water wash, until aqueous phase is neutrality, separate organic facies, and steaming of reducing pressure
Evaporate except the dichloromethane in organic facies, obtain six (4-methoxy ethoxy) ring three phosphorus eyeball；
(5) six (4-methoxy ethoxy) ring three phosphonitrile obtained in step (4) is dissolved in appropriate dichloromethane, at ice
Under the conditions of bath, it is slowly added to the dichloromethane solution of boron chloride, stirs 40 ~ 60min；
(6) it is directly added into appropriate shrend to go out reaction, stands, the water that decompression is distilled off in organic facies, obtain six (4-hydroxyl second
Epoxide) ring three phosphonitrile.
The synthetic method of six (4-hydroxyl-oxethyl) the most according to claim 1 ring three phosphonitrile, it is characterised in that sodium hydride
It is 1.0:1 with the mol ratio of methyl cellosolve.
The synthetic method of six (4-hydroxyl-oxethyl) the most according to claim 1 ring three phosphonitrile, it is characterised in that methoxyl group
Ethanol is 6.5:1 ~ 7.0:1 with the mol ratio of chlordene ring three phosphorus eyeball.
The synthetic method of six (4-hydroxyl-oxethyl) the most according to claim 1 ring three phosphonitrile, it is characterised in that step
(5) in, the mol ratio of boron chloride and six (4-methoxy ethoxy) ring three phosphonitrile is 1.0:1 ~ 1.8:1.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610698487.4A CN106317118B (en) | 2016-08-22 | 2016-08-22 | A kind of synthetic method of six (4- hydroxyl-oxethyls) ring, three phosphonitrile |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610698487.4A CN106317118B (en) | 2016-08-22 | 2016-08-22 | A kind of synthetic method of six (4- hydroxyl-oxethyls) ring, three phosphonitrile |
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| CN106317118B CN106317118B (en) | 2018-06-26 |
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|---|---|---|---|---|
| CN100999445A (en) * | 2006-01-09 | 2007-07-18 | 北京赛科药业有限责任公司 | Demethyl method of aryl methyl ether |
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| CN102766168A (en) * | 2012-08-09 | 2012-11-07 | 西安近代化学研究所 | Synthetic method of 6(4-hydroxyl ethyoxyl) cyclotriphophazene |
| CN102838579A (en) * | 2011-06-20 | 2012-12-26 | 昆明制药集团股份有限公司 | Method for preparing 1,3,6,7-tetrahydroxy xanthone |
| CN103483409A (en) * | 2013-09-24 | 2014-01-01 | 北京满格医药科技有限公司 | Synthetic method for preparing nelarabine |
| CN104311599A (en) * | 2014-09-24 | 2015-01-28 | 中国兵器工业集团第五三研究所 | Preparation method of hexa(4-methoxyphenoxyl)cyclotriphosphazene |
| CN105085267A (en) * | 2014-05-21 | 2015-11-25 | 天津国际生物医药联合研究院 | Synthetic method for salvianolic acid A |
-
2016
- 2016-08-22 CN CN201610698487.4A patent/CN106317118B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100999445A (en) * | 2006-01-09 | 2007-07-18 | 北京赛科药业有限责任公司 | Demethyl method of aryl methyl ether |
| CN102838579A (en) * | 2011-06-20 | 2012-12-26 | 昆明制药集团股份有限公司 | Method for preparing 1,3,6,7-tetrahydroxy xanthone |
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