KR960010667A - 설폰화 포스핀, 이의 제조방법 및 촉매계 성분으로서의 이의 용도 - Google Patents
설폰화 포스핀, 이의 제조방법 및 촉매계 성분으로서의 이의 용도 Download PDFInfo
- Publication number
- KR960010667A KR960010667A KR1019950031280A KR19950031280A KR960010667A KR 960010667 A KR960010667 A KR 960010667A KR 1019950031280 A KR1019950031280 A KR 1019950031280A KR 19950031280 A KR19950031280 A KR 19950031280A KR 960010667 A KR960010667 A KR 960010667A
- Authority
- KR
- South Korea
- Prior art keywords
- sulfuric acid
- solution
- acid
- water
- alkyl
- Prior art date
Links
- 150000003003 phosphines Chemical class 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 title claims 9
- 239000003054 catalyst Substances 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract 13
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract 5
- 229960002645 boric acid Drugs 0.000 claims abstract 5
- 235000010338 boric acid Nutrition 0.000 claims abstract 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000002184 metal Substances 0.000 claims abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract 3
- 239000007983 Tris buffer Substances 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims abstract 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 239000003795 chemical substances by application Substances 0.000 claims abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract 2
- 239000000243 solution Substances 0.000 claims 5
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- -1 alkyl radical Chemical group 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 239000002841 Lewis acid Substances 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 239000004327 boric acid Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 238000006277 sulfonation reaction Methods 0.000 claims 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 claims 2
- YKGBNAGNNUEZQC-UHFFFAOYSA-N 6-methyl-n,n-bis(6-methylheptyl)heptan-1-amine Chemical compound CC(C)CCCCCN(CCCCCC(C)C)CCCCCC(C)C YKGBNAGNNUEZQC-UHFFFAOYSA-N 0.000 claims 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical group [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims 1
- 239000003799 water insoluble solvent Substances 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
-
- 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
- C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
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)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
본 발명은 다음 일반식의 설폰화 포스핀에 관한 것이다.
상기 식에서, R은 탄소수 1 내지4의 알킬 라디킬 또는 사이클로헥실 라디칼이며, M은 수소, 1가 금속, 화학적 당량의 다가 금속 또는 암모늄 이온이거나, 알킬 치화되거나 아릴 치환된 암모늄 이온이고, x는 1,2 또는 3 이며, n은 0또는 1이다.
이러한 화합물은 비설폰화 출발물질을 발연 황산 또는 황산과 오르토붕산의 무수 혼합물로 설포화시켜 수득한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 다음 일반식의 설포화 포스핀.상기 식에서, R은 탄소수 1내지 4의 알킬 라디칼 또는 사이클로헥실 라디칼이며, M은 수소, 1가 금속, 화학적 당량의 다가 금속 또는 암모늄 이온이거나, 알킬 치환되거나 아릴 치환된 암모늄 이온이고, x는 1, 2 또는 3이며, n은 0또는 1이다.
- 트리스(o-톨릴)포스핀 또는 트리스(o-메톡시)포스핀 똔느 이들 화합물 중의 하나의 유도체(여기서, 1또는 2개의 아릴 라디칼은 칸소수 1내지 4의 알킬 라디칼 또는 사이클로헥실 라디칼로 대체된다)를 황산.오르토붕산의 무수계 또는 설폰화제로서의 발연 황산과 반응시킴을 포함하는, 제1항에서 청구한 설폰화 포스핀의 제조방법.
- 제2항에 있어서, 설폰화가 황산/오르토붕산의 무수계를 이용하여 20내지 350℃, 특히 20 내지 170℃에서 수행되는 방법.
- 제2항에 있어서, 설폰화가 황산 중의 삼산화황의 용액, 특히, 용액을 기준으로 하여, 20내지 65중량%의 삼산화황을 포함하는 용액을 사용하여 수행되는 방법.
- 제4항에 있어서, 황산 중의 산산화황의 용액이 루이스산(Lewis acid)을 포함하는 방법.
- 제5항에 있어서, 루이스산이 붕산인 방법.
- 제3항 또는 제6항에 있어서, 붕산이 P(Ⅲ) 1몰당 1mol이상 존재하느 방법.
- 제2항 내지 제7항 주으이 어느 한 항에 있어서, 설폰화 화합물로 물로 희석시키고, 생성된 수용액을 수불용성 유기용매 중의 수불용성 아민의 용액(여기서, 아민은 황산의 화학적 당량당 0.5내지 3mol의 양으로 사용된다)으로 추출한 다음, 유기상을 분리시키고, 염기의 수용액과 긴밀하게 접촉시킨 다음, 수용성 염기를 분리시키고, 이로부터 설폰화 아릴포스핀을 분리시키는 방법.
- 제8항에 있어서, 트리이소옥틸아민이 수불용성 아민으로서 사용되는 방법.
- 제8항에 또는 제9항에 있어서, 톨루엔이 수불용서 용매로서 사용되는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4435189A DE4435189A1 (de) | 1994-09-30 | 1994-09-30 | Neue sulfonierte Phosphine, Verfahren zu ihrer Herstellung und ihre Verwendung als Bestandteil von Katalysatorsystemen |
| DEP4435189.5 | 1994-09-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR960010667A true KR960010667A (ko) | 1996-04-20 |
| KR100353331B1 KR100353331B1 (ko) | 2003-01-06 |
Family
ID=6529758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950031280A KR100353331B1 (ko) | 1994-09-30 | 1995-09-22 | 설폰화 포스핀 및 이의 제조방법 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US5663426A (ko) |
| EP (1) | EP0704450B1 (ko) |
| JP (1) | JP2769803B2 (ko) |
| KR (1) | KR100353331B1 (ko) |
| CN (1) | CN1051557C (ko) |
| AT (1) | ATE189223T1 (ko) |
| DE (2) | DE4435189A1 (ko) |
| ES (1) | ES2143573T3 (ko) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6307087B1 (en) * | 1998-07-10 | 2001-10-23 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| US7223879B2 (en) * | 1998-07-10 | 2007-05-29 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| US6160168A (en) * | 1999-02-25 | 2000-12-12 | Bayer Aktiengesellschaft | Triphenylphosphine mono and dimethoxy tri-sodium sulphonates |
| DE19918284C1 (de) * | 1999-04-22 | 2000-12-14 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung von sulfonierten Arylphosphinen |
| CA2509522C (en) * | 2002-12-09 | 2013-05-07 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| ATE477262T1 (de) * | 2005-09-15 | 2010-08-15 | Dow Global Technologies Inc | Verfahren zur monosulfonierung aromatischer phosphine und daraus entwickeltes zwitterionisches produkt |
| CA2708369C (en) * | 2007-12-12 | 2017-04-04 | Massachusetts Institute Of Technology | Ligands for transition-metal-catalyzed cross-couplings, and methods of use thereof |
| WO2009091669A1 (en) * | 2008-01-15 | 2009-07-23 | Dow Global Technologies Inc. | Sulfonated organophosphine compounds and use in hydroformylation processes |
| EP2231683B1 (en) * | 2008-01-15 | 2016-03-23 | Dow Global Technologies LLC | Sulfonated organophosphine compounds and use thereof in hydroformylation processes |
| WO2009091671A1 (en) * | 2008-01-15 | 2009-07-23 | Dow Global Technologies Inc. | Sulfonated organophosphine compounds and use thereof in hydroformylation processes |
| KR20220056486A (ko) * | 2020-10-28 | 2022-05-06 | 한화솔루션 주식회사 | 설폰화 아릴 포스핀의 제조방법 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB231306A (en) * | 1924-03-08 | 1925-04-02 | Moir Buchanan Centrifugal Proc | Improvements in or relating to means for the manufacture, centrifugally, of pipes, columns and other hollow articles |
| US4248802A (en) | 1975-06-20 | 1981-02-03 | Rhone-Poulenc Industries | Catalytic hydroformylation of olefins |
| FR2338253A1 (fr) | 1976-01-13 | 1977-08-12 | Rhone Poulenc Ind | Procede d'hydrocyanation de composes organiques insatures comportant au moins une double liaison ethylenique |
| US4835202A (en) * | 1987-11-20 | 1989-05-30 | Ciba-Geigy Corporation | (Hydroxyphenyl) phosphine stabilized compositions |
| DE3942791A1 (de) * | 1989-12-23 | 1991-06-27 | Hoechst Ag | Sulfonierte propylphenylphosphane, ihre herstellung und verwendung |
| US5481049A (en) * | 1993-03-30 | 1996-01-02 | Mitsubishi Chemical Corporation | Process for producing alkadienols |
| TW248563B (ko) * | 1993-06-29 | 1995-06-01 | Hoechst Ag |
-
1994
- 1994-09-30 DE DE4435189A patent/DE4435189A1/de not_active Withdrawn
-
1995
- 1995-09-21 ES ES95114851T patent/ES2143573T3/es not_active Expired - Lifetime
- 1995-09-21 DE DE59507687T patent/DE59507687D1/de not_active Expired - Lifetime
- 1995-09-21 EP EP95114851A patent/EP0704450B1/de not_active Expired - Lifetime
- 1995-09-21 AT AT95114851T patent/ATE189223T1/de not_active IP Right Cessation
- 1995-09-22 KR KR1019950031280A patent/KR100353331B1/ko not_active IP Right Cessation
- 1995-09-27 JP JP7249843A patent/JP2769803B2/ja not_active Expired - Lifetime
- 1995-09-28 CN CN95118209A patent/CN1051557C/zh not_active Expired - Fee Related
- 1995-10-02 US US08/538,190 patent/US5663426A/en not_active Expired - Fee Related
-
1997
- 1997-02-18 US US08/801,150 patent/US5780674A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US5780674A (en) | 1998-07-14 |
| ATE189223T1 (de) | 2000-02-15 |
| CN1132208A (zh) | 1996-10-02 |
| JPH08176168A (ja) | 1996-07-09 |
| KR100353331B1 (ko) | 2003-01-06 |
| JP2769803B2 (ja) | 1998-06-25 |
| EP0704450A1 (de) | 1996-04-03 |
| DE4435189A1 (de) | 1996-04-04 |
| DE59507687D1 (de) | 2000-03-02 |
| CN1051557C (zh) | 2000-04-19 |
| EP0704450B1 (de) | 2000-01-26 |
| ES2143573T3 (es) | 2000-05-16 |
| US5663426A (en) | 1997-09-02 |
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