KR930007960A - 알릴포스핀 또는 비닐포스핀의 제조 방법 - Google Patents
알릴포스핀 또는 비닐포스핀의 제조 방법 Download PDFInfo
- Publication number
- KR930007960A KR930007960A KR1019920020039A KR920020039A KR930007960A KR 930007960 A KR930007960 A KR 930007960A KR 1019920020039 A KR1019920020039 A KR 1019920020039A KR 920020039 A KR920020039 A KR 920020039A KR 930007960 A KR930007960 A KR 930007960A
- Authority
- KR
- South Korea
- Prior art keywords
- phosphine
- dialkylphosphine
- vinyl
- dialkylphosphino
- allyl
- Prior art date
Links
- SCESWTHQFQXGMV-UHFFFAOYSA-N ethenylphosphane Chemical compound PC=C SCESWTHQFQXGMV-UHFFFAOYSA-N 0.000 title claims abstract 7
- 238000000034 method Methods 0.000 title claims 18
- QHJWOSHIGFDANE-UHFFFAOYSA-N prop-2-enylphosphane Chemical compound PCC=C QHJWOSHIGFDANE-UHFFFAOYSA-N 0.000 title claims 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract 20
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract 10
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims abstract 6
- 150000003254 radicals Chemical class 0.000 claims abstract 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000001294 propane Substances 0.000 claims abstract 3
- -1 allyl halides Chemical class 0.000 claims 8
- 229920002554 vinyl polymer Polymers 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical group BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims 3
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical group BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 claims 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- 239000001099 ammonium carbonate Substances 0.000 claims 2
- 235000012501 ammonium carbonate Nutrition 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 claims 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- OKMVYXTWPPPSIM-UHFFFAOYSA-N dicyclopentylphosphane Chemical compound C1CCCC1PC1CCCC1 OKMVYXTWPPPSIM-UHFFFAOYSA-N 0.000 claims 1
- IWQIEVOJUWFMSB-UHFFFAOYSA-N dihexylphosphane Chemical compound CCCCCCPCCCCCC IWQIEVOJUWFMSB-UHFFFAOYSA-N 0.000 claims 1
- BYYQOWAAZOHHFN-UHFFFAOYSA-N dioctylphosphane Chemical compound CCCCCCCCPCCCCCCCC BYYQOWAAZOHHFN-UHFFFAOYSA-N 0.000 claims 1
- HOWGUJZVBDQJKV-UHFFFAOYSA-N docosane Chemical compound CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940038384 octadecane Drugs 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- DZMOLBFHXFZZBF-UHFFFAOYSA-N prop-2-enyl dihydrogen phosphate Chemical compound OP(O)(=O)OCC=C DZMOLBFHXFZZBF-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 235000017550 sodium carbonate Nutrition 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 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
-
- 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
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5086—Preparation; Separation; Purification; Stabilisation from phosphonium salts as starting materials
-
- 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
- C07F9/5013—Acyclic unsaturated phosphines
-
- 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
- C07F9/5027—Polyphosphines
-
- 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
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5059—Preparation; Separation; Purification; Stabilisation by addition of phosphorus compounds to alkenes or alkynes
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
알릴포스핀 및 비닐포스핀은 각각 알릴할라이드 또는 비닐할라이드와 포스핀의 반응에 의해 제조된다. 바람직하게 포스핀이 2차 포스핀이므로 알킬리알킬포스핀 또는 디알킬비닐포스핀이 형성된다. 부가적으로 유리 라디칼 조건하에서 알릴디알킬포스핀을 디알킬포스핀과 반응시켜 1, 3-비스-(디알킬포스피노)프로판을 산출할 수 있다.
유리 라디칼 조건하에서 디알킬비닐포스핀을 디알킬포스핀과 부가적으로 반응시켜 1, 2-비스-(디알킬포스피노)-에탄을 산출할 수 있다. 이들 화합물은 비덴테이트 리간드로서 유용하다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (18)
- 포스핀을 알릴할라이드 또는 비닐할라이드와 반응시켜 각각 알릴포스포늄 염 또는 비닐포스포늄 염을 형성하고, 이어서 염기로 처리하여 포스포늄 염을 알릴포스핀 또는 비닐포스핀 염기로 전환시키는 것으로 구성되는 알릴포스핀 또는 비닐포스핀의 제조 방법.
- 제1항에 있어서, 2차 포스핀이 알릴할라이드와 반등되는 방법.
- 제1항에 있어서, 2차 포스핀이 비닐할라이드와 반등되는 방법.
- 제2항에 있어서, 알릴할라이드 포스핀이 알릴브로마이드인 방법.
- 제3항에 있어서, 비닐할라이드 포스핀이 비닐브로마이드인 방법.
- 제1내지 5항 중의 어느 한 항에 있어서, 포스핀은 디이소부틸프로핀, 디시클로핵실포스핀, 디-n-헥실포스핀, 디시클로펜틸 포스핀 또는 디-n-옥틸포스핀인 방법.
- 제6항에 있어서, 염기는 탄산나트륨, 탄산수소나트륨, 탄산 암모늄 또는 탄산 수소 암노늄인 방법.
- 제1내지 5항 및 7항 중의 어느 한 항에 있어서, 반응은 비극성유기 용매에서 수행되는 방법.
- 제8항에 있어서, 반응은, 비점이 원하는 알릴포스핀 또는 비닐포스핀의 비점보다 약 20내지 30℃가 더 높은 비극성유기 용매에서 수행되는 방법.
- 제8항에 있어서, 반응은 테트라데칸, 핵사데칸, 옥타데칸, 도코산, 또는 아이코산에서 수행되는 방법.
- 제1내지 5, 7, 9 및 10항 중의 어느 한 항에 있어서, 알릴할라이드 또는 비닐할라이드의 첨가후, 염기의 첨가전에 물이 반응혼합물에 첨가되는 방법.
- 제11항에 있어서, 염기는 탄산 수소 나트륨인 방법.
- 제1내지 5, 7, 9, 10 및 12항 중의 어느 한 항에 있어서, 아세토니트릴이 또한 반응 혼합물에 존재하는 방법.
- 제13항에 있어서, 얻어진 알릴포스핀 또는 비닐포스핀은 유리 라디칼 조건하에서 포스핀과의 부가적인 반응에 적용되는 방법.
- 제1 내지 5, 7, 9, 10 및 12 내지 14항 중의 어느 한 항에 있어서, 디알킬포스핀이 알릴브로마이드와 반응하여 알릴디알킬포스핀을 형성하고, 이는 유리 라디칼 조건하에서 디알킬포스핀과 부가적으로 반응하여 1, 3-비스-(디알킬포스피노)프로판을 형성하는 방법.
- 제16항에 있어서, 알릴브로마이드와 반응된 디알킬포스핀이 알릴디알킬포스핀과 반응된 디알킬포스핀과 동일한 것이어서, 대칭 1, 3-비스-(디알킬포스피노)프로판이 형성되는 방법.
- 제1 내지 5, 7, 9, 10 및 12 내지 14항 중의 어느 한 항에 있어서, 디알킬포스핀이 비닐브로마이드와 반응하여 디알킬비닐포스핀을 형성하고, 이는 유리라디칼 조건하에서 디알킬포스핀과 부가적으로 반응하여 1, 2-비스-(디알킬포스피노)에탄을 형성하는 방법.
- 제17항에 있어서, 비닐브로마이드와 반응된 디알킬포스핀이 디알킬비닐포스핀과 반응된 디알킬포스핀과 동일한 것이어서, 대칭 1, 2-비스-(디알킬포스피노)에탄이 형성되는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002054546A CA2054546A1 (en) | 1991-10-30 | 1991-10-30 | Method of preparing a phosphine compound |
| CA2,054,546 | 1991-10-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR930007960A true KR930007960A (ko) | 1993-05-20 |
| KR100250872B1 KR100250872B1 (ko) | 2000-05-01 |
Family
ID=4148669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019920020039A KR100250872B1 (ko) | 1991-10-30 | 1992-10-29 | 알릴포스핀 또는 비닐포스핀의 제조 방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5250736A (ko) |
| EP (1) | EP0539677B1 (ko) |
| JP (1) | JPH05222075A (ko) |
| KR (1) | KR100250872B1 (ko) |
| AT (1) | ATE159024T1 (ko) |
| CA (1) | CA2054546A1 (ko) |
| DE (1) | DE69222613D1 (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3467307B2 (ja) * | 1994-03-31 | 2003-11-17 | 信越化学工業株式会社 | ホスホニウム塩の製造方法 |
| US6455720B1 (en) * | 2000-06-28 | 2002-09-24 | Takasago International Corporation | 2,2(diarlyl)vinylphosphine compound, palladium catalyst thereof, and process for producing arylamine, diaryl, or arylalkyne with the catalyst |
| WO2006020639A2 (en) * | 2004-08-12 | 2006-02-23 | Sigma-Aldrich Co. | Stabilized borane-tetrahydrofuran complex |
| US7750168B2 (en) * | 2006-02-10 | 2010-07-06 | Sigma-Aldrich Co. | Stabilized deuteroborane-tetrahydrofuran complex |
| US9707551B2 (en) | 2013-01-23 | 2017-07-18 | Hokko Chemical Industry Co., Ltd. | Reaction catalyst for cross-coupling and method for manufacturing aromatic compound |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3010999A (en) * | 1960-05-20 | 1961-11-28 | Monsanto Chemicals | Ethylenically unsaturated phosphorus compounds |
| US3389183A (en) * | 1965-06-07 | 1968-06-18 | Procter & Gamble | Process for the preparation of tertiary phosphines |
| DE2407461C2 (de) * | 1974-02-16 | 1983-03-03 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Alkylphosphinen |
-
1991
- 1991-10-30 CA CA002054546A patent/CA2054546A1/en not_active Abandoned
-
1992
- 1992-08-11 US US07/927,998 patent/US5250736A/en not_active Expired - Fee Related
- 1992-08-18 EP EP92114056A patent/EP0539677B1/en not_active Expired - Lifetime
- 1992-08-18 AT AT92114056T patent/ATE159024T1/de not_active IP Right Cessation
- 1992-08-18 DE DE69222613T patent/DE69222613D1/de not_active Expired - Lifetime
- 1992-10-26 JP JP4309810A patent/JPH05222075A/ja active Pending
- 1992-10-29 KR KR1019920020039A patent/KR100250872B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR100250872B1 (ko) | 2000-05-01 |
| US5250736A (en) | 1993-10-05 |
| CA2054546A1 (en) | 1993-05-01 |
| ATE159024T1 (de) | 1997-10-15 |
| EP0539677B1 (en) | 1997-10-08 |
| DE69222613D1 (de) | 1997-11-13 |
| JPH05222075A (ja) | 1993-08-31 |
| EP0539677A1 (en) | 1993-05-05 |
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| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| LAPS | Lapse due to unpaid annual fee |