CN107936057B - 一种二芳基磷氯化合物的制备方法 - Google Patents
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- -1 diaryl phosphorus chlorine Chemical compound 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011574 phosphorus Substances 0.000 claims abstract description 17
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 17
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 7
- 239000011701 zinc Substances 0.000 claims abstract description 7
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 claims description 5
- YFXAQACLGBPKCQ-UHFFFAOYSA-N NCC(C=C1)=CC=C1[P] Chemical compound NCC(C=C1)=CC=C1[P] YFXAQACLGBPKCQ-UHFFFAOYSA-N 0.000 claims description 3
- PIAHJQSBEOUKNB-UHFFFAOYSA-N NCC1=C(C=CC=C1)[P] Chemical compound NCC1=C(C=CC=C1)[P] PIAHJQSBEOUKNB-UHFFFAOYSA-N 0.000 claims description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052756 noble gas Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 11
- 239000003446 ligand Substances 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 238000012805 post-processing Methods 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 238000004821 distillation Methods 0.000 abstract 1
- 239000003863 metallic catalyst Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000004679 31P NMR spectroscopy Methods 0.000 description 4
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 4
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DFHSDSOKUONELB-UHFFFAOYSA-N C1=CC(=CC=C1CN)P(Cl)Cl Chemical compound C1=CC(=CC=C1CN)P(Cl)Cl DFHSDSOKUONELB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- MKRZFOIRSLOYCE-UHFFFAOYSA-L zinc;methanesulfonate Chemical compound [Zn+2].CS([O-])(=O)=O.CS([O-])(=O)=O MKRZFOIRSLOYCE-UHFFFAOYSA-L 0.000 description 2
- UYAADBLIRXSMHB-UHFFFAOYSA-N C1(=CC=CC=C1)PC1=CC=CC=C1.[Cl] Chemical compound C1(=CC=CC=C1)PC1=CC=CC=C1.[Cl] UYAADBLIRXSMHB-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- GJMMXPXHXFHBPK-UHFFFAOYSA-N [P].[Cl] Chemical compound [P].[Cl] GJMMXPXHXFHBPK-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
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- 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
- C07F9/52—Halophosphines
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种二芳基磷氯化合物的制备方法，属于有机合成领域。该方法以三芳基磷为起始原料，三氟甲烷磺酸锌为催化剂，与三氯化磷反应后经蒸馏得到芳基磷氯化合物。本发明与现有技术相比反应收率高，后处理简单，特别适合带有取代基的二芳基磷氯化合物的制备，更适合工业化生产。制得的芳基磷氯化合物可用于合成金属催化剂的配体，应用于有机光电材料及医药等领域。
Description
技术领域
本发明属于有机合成领域，涉及一类有机磷化合物的合成方法，尤其涉及二芳基磷氯化合物的制备方法。
背景技术
有机磷配体参与的金属催化偶联反应在合成OLED功能材料、高分子聚合物、药物分子以及生物活性化合物中有着非常广泛的用途。有机磷配体的结构和性质为调节过渡金属络合物催化剂性能、实现适应各种不同反应需要的多样性催化剂的合成提供了良好的基础。在磷配体的设计和合成方面，芳基磷氯化合物作为重要的有机中间体，对于磷配体结构的多样性起着至关重要的作用。
目前，二苯基磷氯化合物的制备方法通常是由苯和三氯化磷在无水三氯化铝和吡啶催化作用下反应生成苯基二氯化磷，然后PhPCl2在无水AlCl3作用下发生歧化反应得到Ph2PCl，该路线的收率仅为35％，而且需要使用较大量的三氯化铝，后处理繁琐，产生废料较多。对于含有取代基的二芳基磷氯化合物，一般是通过芳基格氏试剂与二氯化(二甲氨基)磷反应，然后再与氯化氢气体反应得到相应的二芳基磷氯化合物。反应需要用到氯化氢气体，限制了其在产业化中的应用。专利JPH0352894A报道了一种通过二芳基磷氧化合物与三氯化磷反应制备二芳基磷氯化合物的方法，但是二芳基磷氧化合物的合成比较繁琐。鉴于该类化合物在有机磷化学中的重要地位，探索更加高效、实用的二芳基磷氯化合物的合成方法十分必要。
发明内容
本发明目的在于提供一种收率高、后处理简单、适合工业化生产二芳基磷氯化合物的新制备方法。
为实现本发明目的，本发明反应路线如下：
本发明反应步骤如下：
在惰气保护下，向干燥反应器中加入三芳基磷、溶剂四氯化碳以及三氟甲烷磺酸锌，然后在0～10℃条件下向体系中滴加三氯化磷，滴加完毕后升温至60～80℃反应，反应结束后停止反应。反应液经硅藻土过滤，滤液常压蒸出溶剂后，再减压蒸馏得到二芳基磷氯化合物；
本发明涉及的三芳基磷为三苯基磷、三(2-甲基苯基)磷、三(4-甲基苯基)磷或者三(3,5-二甲基苯基)磷。
本发明涉及的二芳基磷氯化合物为二苯基氯化磷、二(2-甲基苯基)氯化磷、二(4-甲基苯基)氯化磷或者二(3,5-二甲基苯基)氯化磷。
本发明所述的三芳基磷与三氯化磷的摩尔比为2-2.2:1，所述的三芳基磷与三氟甲烷磺酸锌的摩尔比为1:0.01-0.1。
本发明有益效果在于：以三芳基磷和三氯化磷为起始原料，利用三氟甲烷磺酸锌作为催化剂发生反歧化反应生成二芳基磷氯化合物，改变了传统工艺中当量级三氯化铝的使用，特别是对于带有取代基的二芳基磷氯化合物，避免了对设备要求较高的氯化氢气体的使用。该反应条件温和，产生废料少，生成二芳基磷氯化合物的收率在90％以上，特别适合带有取代基的二芳基磷氯化合物的制备，更适合工业化生产。制得的芳基磷氯化合物可用于有机合成及作为农药、医药和染料中间体等领域。
具体实施方式
为更好地对本发明进行详细说明，举实例如下：
实施例1二苯基氯化磷的合成
向干燥反应器中加入三苯基磷(1mol,262g)、1L四氯化碳以及三氟甲烷磺酸锌(0.01mol,3.7g)，然后在0-10℃条件下向体系中滴加三氯化磷(0.5mol,69g)，滴加完毕后升温至60℃反应12小时，停止反应。反应液经硅藻土过滤，滤液常压蒸出溶剂后，再减压蒸馏得到二苯基氯化磷307g，收率93％；31P NMR(162MHz,CDCl3),δ:80.5；1HNMR(400MHz,CDCl3):7.65-7.68(m,4H),7.42-7.45(m,6H)。
实施例2二(2-甲基苯基)氯化磷的合成
向干燥反应器中加入三(2-甲基苯基)磷(1mol,304g)、1L四氯化碳以及三氟甲烷磺酸锌(0.1mol,36.2g)，然后在0-10℃条件下向体系中滴加三氯化磷(0.5mol,69g)，滴加完毕后升温至80℃反应10小时，停止反应。反应液经硅藻土过滤，滤液常压蒸出溶剂后，再减压蒸馏得到二(2-甲基苯基)氯化磷343g，收率92％；31P NMR(162MHz,CDCl3):66.9；1HNMR(400MHz,CDCl3):7.40-7.43(m,2H),7.21-7.25(m,2H),7.10-7.17(m,4H),2.41(s,6H)。
实施例3二(4-甲基苯基)氯化磷的合成
向干燥反应器中加入三(4-甲基苯基)磷(1.1mol,334g)、1L四氯化碳以及三氟甲烷磺酸锌(0.05mol,18.5g)，然后在0-10℃条件下向体系中滴加三氯化磷(0.5mol,69g)，滴加完毕后升温至60℃反应12小时，停止反应。反应液经硅藻土过滤，滤液常压蒸出溶剂后，再减压蒸馏得到二(4-甲基苯基)氯化磷339g，收率91％；31P NMR(162MHz,CDCl3),δ:81.6；1H NMR(400MHz,CDCl3)7.58(d,J＝8.1Hz,4H),7.34(d,J＝8.1Hz,4H),2.46(s,6H)。
实施例4二(3,5-二甲基苯基)氯化磷的合成
向干燥反应器中加入三(3,5-二甲基苯基)磷(1mol,346g)、1L四氯化碳以及三氟甲烷磺酸锌(0.01mol,3.7g)，然后在0-10℃条件下向体系中滴加三氯化磷(0.5mol,69g)，滴加完毕后升温至60℃反应12小时，停止反应。反应液经硅藻土过滤，滤液常压蒸出溶剂后，再减压蒸馏得到二(3,5-二甲基苯基)氯化磷390g，收率94％；31P NMR(162MHz,CDCl3),δ:81.9；1H NMR(400MHz,CDCl3)7.26(s,2H),7.22(s,2H),7.03(s,2H),2.33(s,12H)。
Claims (2)
1.一种二芳基磷氯化合物的制备方法，其特征在于，通过如下步骤实现：在惰气保护下，向干燥反应器中加入三芳基磷、溶剂四氯化碳以及三氟甲烷磺酸锌，然后在0~10 ºC条件下向体系中滴加三氯化磷，滴加完毕后升温至60 ~80 ºC反应，反应结束后停止反应；反应液经硅藻土过滤，滤液常压蒸出溶剂后，再减压蒸馏得到二芳基磷氯化合物；
所述的三芳基磷为三苯基磷、三（2-甲基苯基）磷、三（4-甲基苯基）磷或者三（3,5-二甲基苯基）磷；
所述的二芳基磷氯化合物为二苯基氯化磷、二（2-甲基苯基）氯化磷、二（4-甲基苯基）氯化磷或者二（3,5-二甲基苯基）氯化磷。
2.如权利要求1所述的二芳基磷氯化合物的制备方法，其特征在于，所述的三芳基磷与三氯化磷的摩尔比为2-2.2 : 1，所述的三芳基磷与三氟甲烷磺酸锌的摩尔比为1 : 0.01-0.1。
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4521347A (en) * | 1982-05-03 | 1985-06-04 | Hoechst Aktiengesellschaft | Process for preparing chlorophenylphosphanes |
| US4708824A (en) * | 1984-06-30 | 1987-11-24 | Hoechst Aktiengesellschaft | Process for the preparation of chloro(phenyl)phospines |
| WO1998014455A1 (de) * | 1996-09-30 | 1998-04-09 | Basf Aktiengesellschaft | Verfahren zur herstellung von phenylchlorphosphinen |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4521347A (en) * | 1982-05-03 | 1985-06-04 | Hoechst Aktiengesellschaft | Process for preparing chlorophenylphosphanes |
| US4708824A (en) * | 1984-06-30 | 1987-11-24 | Hoechst Aktiengesellschaft | Process for the preparation of chloro(phenyl)phospines |
| WO1998014455A1 (de) * | 1996-09-30 | 1998-04-09 | Basf Aktiengesellschaft | Verfahren zur herstellung von phenylchlorphosphinen |
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