CN109232977B - 一种含有活性基团的磷杂菲衍生物阻燃剂及其制备方法 - Google Patents
一种含有活性基团的磷杂菲衍生物阻燃剂及其制备方法 Download PDFInfo
- Publication number
- CN109232977B CN109232977B CN201811060511.7A CN201811060511A CN109232977B CN 109232977 B CN109232977 B CN 109232977B CN 201811060511 A CN201811060511 A CN 201811060511A CN 109232977 B CN109232977 B CN 109232977B
- Authority
- CN
- China
- Prior art keywords
- phosphaphenanthrene
- acrolein
- flame retardant
- abd
- dopo
- 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.)
- Active
Links
- LJUXFZKADKLISH-UHFFFAOYSA-N benzo[f]phosphinoline Chemical class C1=CC=C2C3=CC=CC=C3C=CC2=P1 LJUXFZKADKLISH-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000003063 flame retardant Substances 0.000 title claims abstract description 14
- 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 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims description 6
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims abstract description 16
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- ZKWPMZVVAJSYNI-UHFFFAOYSA-N prop-2-enal Chemical compound C=CC=O.C=CC=O ZKWPMZVVAJSYNI-UHFFFAOYSA-N 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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 5
- 239000012043 crude product Substances 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims 1
- 238000007259 addition reaction Methods 0.000 abstract description 4
- 125000003172 aldehyde group Chemical group 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 3
- -1 ABD compound Chemical class 0.000 abstract 1
- 238000010189 synthetic method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004821 distillation Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
-
- 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
- C07F9/6571—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 oxygen atoms as the only ring hetero atoms
- C07F9/657163—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 oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657172—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 oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/388—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to carbon and/or to hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
本发明公开了一种含有活性基团的磷杂菲衍生物阻燃剂，简称为ABD，ABD的结构式如下，其合成方法是：在有机溶剂体系中采用丙烯醛(Acrolein)和9,10‑二氢‑9‑氧杂‑10‑磷杂菲‑10‑氧化物(DOPO)为原料，0‑20℃条件下反应，在有机溶剂中实现DOPO中的P‑H键与丙烯醛中的醛基和双键同时进行加成反应，脱除溶剂后并通过热水洗涤提纯，分离出产物，烘干后获得ABD化合物。
Description
技术领域
本发明涉及一种含有活性基团的磷杂菲衍生物阻燃剂及其制备方法，是一种新型的磷杂菲衍生物阻燃剂，属于利用化学合成方法制备阻燃助剂的技术领域。
背景技术
近些年来，磷杂菲DOPO化合物由于其优异的阻燃性能和改变分子的物理性质在环氧树脂中得到广泛应用。磷杂菲DOPO的衍生物比如DOPO-HQ、2DOPO-2NH2、2DOPO-2PhOH、DOPO-ITA、DOPO-MA等化合物也被陆续开发,并应用在环氧树脂中，赋予了环氧树脂优异的阻燃性能和物理性能。
在《新型阻燃剂制造与应用》中提到磷杂菲衍生物2DOPO-2NH2、2DOPO-2PhOH，其合成方法是DOPO中的P-H键与羰基加成后的产物。在《新型阻燃剂制造与应用》中提到磷杂菲衍生物DOPO-MA、DOPO-ITA，其合成方法是DOPO中的P-H键与双键加成后的产物。
本发明的磷杂菲衍生物，制备方法简单，不需要在加热条件下即可反应，且只需要一步反应，0-20℃时，DOPO中的P-H键即可与丙烯醛中的双键和醛基同时进行加成反应，反应速率快，无副产物，产率高，提纯方法简单，获得产物还含有可活性基团，化学结构中磷含量更高。
发明内容
本发明采用丙烯醛(Acrolein)和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)为原料，通过DOPO中的P-H键与丙烯醛中的醛基和双键同时进行加成反应，制备的一种含有活性基团的磷杂菲衍生物，简称为ABD。
ABD分子式如下：
ABD的制备采用丙烯醛(Acrolein)和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)为原料，在有机溶剂中反应,通过蒸馏方法除去有机溶剂获得ABD粗产物，并将ABD在70-100℃热水中洗涤提纯，获得ABD产物。
所用合成原料：丙烯醛、9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物；有机溶剂包括：四氢呋喃、甲苯、二甲苯、氯仿、乙二醚、丙酮。
合成工艺
在有机溶剂体系中：将丙烯醛和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物按照一定的比例加入到有机溶剂中，其中丙烯醛和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物的摩尔比为1:2.0-1:4.0，有机溶剂的质量为所用9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物质量的4-8倍，反应温度在0-20℃，搅拌条件下反应1-3小时，有机溶剂为四氢呋喃、甲苯、二甲苯、氯仿、乙二醚、丙酮中的一种，通过蒸馏方法除去有机溶剂获得ABD粗产物。
将ABD粗产物加入到热水中，保持温度在70-100℃，搅拌洗涤，通过分液漏斗等方法分离出产物，烘干后获得产物ABD，产率在99％以上，纯度98％以上。
有益效果
(1)本发明的含有活性基团的磷杂菲衍生物，其结构与磷杂菲衍生物2DOPO-2NH2、DOPO-MA相比，结构中磷含量更高；与磷杂菲衍生物DOPO-MA相比，还含有一个活性基团羟基，可以作为一种聚氨酯的反应性阻燃剂；
(2)本发明的含有活性基团的磷杂菲衍生物，制备方法简单，不需要在加热条件下即可反应，且只需要一步反应，0-20℃时，DOPO中的P-H键即可与丙烯醛中的双键和醛基同时进行加成反应，反应速率快，无副产物，产率高，且提纯方法简单，处理效率高，有效降低了成本，有利于产业化放大生产。
附图说明
附图1制得的ABD的核磁氢谱图；
附图2制得的ABD的红外谱图。
具体实施方式
实施例1
将5.6g(0.1mol)丙烯醛(Acrolein)和43.2g(0.2mol)9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)加入到装有175二甲苯的三口烧瓶中，在室温条件下，温度为0℃时，快速搅拌，反应3小时，反应结束后，减压蒸馏，除去二甲苯，在三口烧瓶中加入热水，保持温度70℃，通过分液漏斗分离出产物，烘干后，得到产物，经与标准谱图比对，即为目标产物，产率99％，纯度99.5％。
实施例2
将5.6g(0.1mol)丙烯醛(Acrolein)和54g(0.25mol)9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)加入到装有270g四氢呋喃的三口烧瓶中，在室温条件下，温度为5℃时，快速搅拌，反应2小时，反应结束后，常压蒸馏，除去四氢呋喃，在三口烧瓶中加入热水，保持温度80℃，通过分液漏斗分离出产物，烘干后，得到产物，经与标准谱图比对，即为目标产物，产率99.5％，纯度99％。
实施例3
将5.6g(0.1mol)丙烯醛(Acrolein)和64.8g(0.3mol)9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)加入到装有380g氯仿的三口烧瓶中，在室温条件下，温度为15℃时，快速搅拌，反应1小时，反应结束后，减压蒸馏，除去氯仿，在三口烧瓶中加入热水，保持温度90℃，通过分液漏斗分离出产物，烘干后，得到产物，经与标准谱图比对，即为目标产物，产率99.7％，纯度98.5％。
实施例4
将5.6g(0.1mol)丙烯醛(Acrolein)和86.4g(0.4mol)9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)加入到装有690g丙酮的三口烧瓶中，在室温条件下，温度为20℃时，快速搅拌，反应1小时，反应结束后，减压蒸馏，除去丙酮，在三口烧瓶中加入热水，保持温度100℃，通过分液漏斗分离出产物，烘干后，得到产物，经与标准谱图比对，即为目标产物，产率99.8％，纯度98％。
Claims (4)
1.一种含有活性基团的磷杂菲衍生物阻燃剂的制备方法，其特征在于，所述阻燃剂的分子结构式为：
该方法是：在有机溶剂中将丙烯醛(Acrolein)和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)搅拌混合在0-20℃下反应1-3小时，脱除溶剂后得到ABD粗产物；再将粗产物加入到热水中，保持温度在70-100℃，洗涤、分离，烘干后获得ABD。
2.根据权利要求1所述的含有活性基团的磷杂菲衍生物阻燃剂的制备方法，其特征在于，所述的丙烯醛和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物的摩尔比为1:2.0-1:4.0。
3.根据权利要求1所述的含有活性基团的磷杂菲衍生物阻燃剂的制备方法，其特征在于，所述的有机溶剂的质量为所用9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物质量的4-8倍。
4.根据权利要求1所述的含有活性基团的磷杂菲衍生物阻燃剂的制备方法，其特征在于，所述的有机溶剂为四氢呋喃、甲苯、二甲苯、氯仿、乙二醚、丙酮中的一种。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811060511.7A CN109232977B (zh) | 2018-09-12 | 2018-09-12 | 一种含有活性基团的磷杂菲衍生物阻燃剂及其制备方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811060511.7A CN109232977B (zh) | 2018-09-12 | 2018-09-12 | 一种含有活性基团的磷杂菲衍生物阻燃剂及其制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109232977A CN109232977A (zh) | 2019-01-18 |
| CN109232977B true CN109232977B (zh) | 2020-11-13 |
Family
ID=65067533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811060511.7A Active CN109232977B (zh) | 2018-09-12 | 2018-09-12 | 一种含有活性基团的磷杂菲衍生物阻燃剂及其制备方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109232977B (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112442212A (zh) * | 2019-08-28 | 2021-03-05 | 广东广山新材料股份有限公司 | 一种含磷的反应型阻燃剂及其制备方法和应用 |
| CN112442073A (zh) * | 2019-08-28 | 2021-03-05 | 广东广山新材料股份有限公司 | 一种含磷的反应型阻燃剂及其制备方法和应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610362A (zh) * | 2015-01-28 | 2015-05-13 | 中国科学技术大学 | 一种含有磷杂菲基团的阻燃二元醇及其制备方法 |
| CN106366128A (zh) * | 2015-07-24 | 2017-02-01 | 中山台光电子材料有限公司 | 膦菲类化合物及其制备方法和应用 |
| CN107400193A (zh) * | 2017-08-04 | 2017-11-28 | 武汉工程大学 | 一种新型dopo型化合物在ep中的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI359151B (en) * | 2008-07-02 | 2012-03-01 | Chang Chun Plastics Co Ltd | Phosphorus-containing compounds and their preparat |
-
2018
- 2018-09-12 CN CN201811060511.7A patent/CN109232977B/zh active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610362A (zh) * | 2015-01-28 | 2015-05-13 | 中国科学技术大学 | 一种含有磷杂菲基团的阻燃二元醇及其制备方法 |
| CN106366128A (zh) * | 2015-07-24 | 2017-02-01 | 中山台光电子材料有限公司 | 膦菲类化合物及其制备方法和应用 |
| CN107400193A (zh) * | 2017-08-04 | 2017-11-28 | 武汉工程大学 | 一种新型dopo型化合物在ep中的应用 |
Non-Patent Citations (2)
| Title |
|---|
| "ＤＯＰＯ及其衍生物的合成和阻燃性能研究进展";万元俊;《高分子通报》;20171130(第11期);45-52页 * |
| "基于DOPO的阻燃剂合成及其对不同高分子材料的阻燃效率";Christoph Klinkowski等;《中国材料进展》;20130331;第32卷(第3期);144-154页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109232977A (zh) | 2019-01-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110510605B (zh) | 一种富氮基团功能化石墨烯、制备方法及应用 | |
| CN109232977B (zh) | 一种含有活性基团的磷杂菲衍生物阻燃剂及其制备方法 | |
| KR101115412B1 (ko) | 하이드록시클로로퀸의 신규 제조방법 | |
| CN111233947A (zh) | 一类呋喃糖环状磷酸酯阻燃剂的结构及其制备方法 | |
| CN109096122B (zh) | 制备亚精胺的方法 | |
| CN108586514B (zh) | 一种二异丙胺硅烷合成方法 | |
| WO2021120896A1 (zh) | 一种降冰片烷二甲胺的制备方法 | |
| CN114853658B (zh) | 一种9-(4-溴苯基)咔唑的合成方法 | |
| KR101965572B1 (ko) | 열가소성 폴리우레탄 제조용 난연 다이올 합성방법, 열가소성 폴리우레탄 제조용 난연 다이올 및 이에 따른 열가소성 폴리우레탄 | |
| CN111646964A (zh) | 一种碱催化的合成2h-吡喃-2-酮衍生物新方法 | |
| KR20190029233A (ko) | 디메틸올부탄알의 분리방법 및 이를 이용한 트리메틸올프로판의 제조방법 | |
| CN111635431B (zh) | 一种苯基膦酸二苯酯的制备方法 | |
| CN111675591B (zh) | 一种苯并菲化合物的合成方法 | |
| CN110935435B (zh) | 一种用于制备环状多元醇的催化剂及其应用 | |
| CN103342715A (zh) | 一种含有胺丙基的有机肟基硅化合物的制备方法 | |
| CN109305985B (zh) | 二甲基乙烯基氯硅烷的合成方法 | |
| KR20130133315A (ko) | 물에 안정한 루이스 산을 이용한 소르비톨로부터 아이소소바이드의 제조방법 | |
| CN113105506A (zh) | 一种磷杂菲衍生物阻燃剂及其制备方法 | |
| CN111574532A (zh) | 一种多相催化制备二氧化双环戊二烯的方法 | |
| US6124492A (en) | Process for preparing bis(3-t-butyl-4-hydroxyphenyl-2,4-di-t-butylphenyl)resorcinol diphosphate | |
| CN114057791B (zh) | 一种耐水解亚磷酸酯配体和制备方法及其催化烯烃氢甲酰化反应制备线性醛的用途 | |
| KR101671770B1 (ko) | 마이크로파를 이용한 5-아세트옥시메틸푸르푸랄의 신규한 제조방법 | |
| KR102088961B1 (ko) | 에폭시 반응성 희석제 및 그 제조방법 | |
| CN112778099B (zh) | 一种合成3,6,9,12,15-五氧杂二十八烷-1-醇的方法 | |
| RU2797603C1 (ru) | Способ получения 1-бромметил-4-хлорметилбензола |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |