KR920012101A - 수용성 디포스핀의 제조방법 - Google Patents
수용성 디포스핀의 제조방법 Download PDFInfo
- Publication number
- KR920012101A KR920012101A KR1019910021507A KR910021507A KR920012101A KR 920012101 A KR920012101 A KR 920012101A KR 1019910021507 A KR1019910021507 A KR 1019910021507A KR 910021507 A KR910021507 A KR 910021507A KR 920012101 A KR920012101 A KR 920012101A
- Authority
- KR
- South Korea
- Prior art keywords
- water
- solution
- reaction mixture
- aqueous
- different
- Prior art date
Links
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 title claims 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims 6
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 239000000243 solution Substances 0.000 claims 6
- 239000011541 reaction mixture Substances 0.000 claims 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- -1 biaryl compound Chemical class 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 238000006277 sulfonation reaction Methods 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- SZKMTZNASRXXCE-UHFFFAOYSA-N [2-[2-(diphenylphosphanylmethyl)phenyl]phenyl]methyl-diphenylphosphane Chemical group C=1C=CC=C(C=2C(=CC=CC=2)CP(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 SZKMTZNASRXXCE-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 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
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5054—Preparation; Separation; Purification; Stabilisation by a process in which the phosphorus atom is not involved
-
- 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
- C07F9/5027—Polyphosphines
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)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
Claims (7)
- 하기 일반식의 바이아릴 화합물을 0-60℃의 온도에서 황산에 용해시킨 삼산화황의 용액으로 처리하고, 혼합물을 20-60℃, 특히 20-30℃에서 1-60시간 동안 반응시키고, 온도를 0-20℃, 특히 0-10℃로 유지하면서 반응 혼합물을 물로 희석한 후 후작업 처리함을 특징으로 하는 수용성 디포스핀의 제조방법.상기 식중, A는 동일하거나 서로 상이하며, 각각 알킬, 사이클로알킬, 페닐, 톨릴 또는 나프틸 라디칼이고, R1은 동일하거나 서로 상이하며, 각각 수소 또는 탄소수 1-14의 알킬 사이클로아톡시 라디칼, 또는 융합 벤젠고리이며, m은 동일하거나 서로 상이하며, 0-5의 정수이고, n은 동일하거나 서로 상이하며, 0-4의 정수이다.
- 제1항에 있어서, 황산에 용해되어 있는 삼산화 황의 농도가 용액에 대하여 20-65중량%임을 특징으로 하는 제조방법.
- 제1항 또는 제2항에 있어서, 반응 혼합물을 20-30℃에서 반응시킴을 특징으로 하는 제조방법.
- 제1항 내지 제3항 중 어느 한 항에 있어서, 물로 희석시킨 반응 혼합물을 0-20℃, 특히 0-10℃로 유지하면서 알칼리 금속 수산화물 수용액으로 중화시키고, 침전된 알칼리 금속 황산염을 여거하며, 수용액을 온화한 조건하에서 농축시키고, 생성물 결정을 소량의 물에 용해시키며, 용액을 저급 알콜, 바람직하게는 C1-C4-알콜과 혼합하고, 여과하며, 온화한 조건하에서 용매를 제거하여 수용성 디포스핀을 분리함을 특징으로 하는 제조방법.
- 제1항 내지 제3항 중 어느 한 항에 있어서, 물로 희석시킨 반응 혼합물로 수-불용성 유기 용매에 용해시킨 수-불용성 아민의 용액으로 추출하고, 유기상을 제거하여 염기 수용액과 균질하게 접촉시키며, 제거된 수상으로부터 수용성 디포스핀을 분리함을 특징으로 하는 제조방법.
- 제1항 내지 4항 중 어느 한 항에 있어서, 설폰화 반응에 사용되는 하기 일반식(I)의 바이아릴 화합물은 하기 일반식(II)의 디리튬 화합물을 하기 일반식(III)의 할로겐화 디아릴알킬렌포스핀과 반응시켜 제조된 것임을 특징으로 하는 제조방법.상기 식중, A, R′. m 및 n은 상기 제1항에서 정의 바와 동일하고 X는 염소, 브롬 또는 요오드이다.
- 제1항에 따른, 2,2′비스(디페닐포스피노메틸)바이페닐의 설폰화 반응에 의해 얻어지는 생성물.※참고사항: 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4040314.9 | 1990-12-17 | ||
DE4040314A DE4040314A1 (de) | 1990-12-17 | 1990-12-17 | Verfahren zur herstellung wasserloeslicher diphosphane |
Publications (2)
Publication Number | Publication Date |
---|---|
KR920012101A true KR920012101A (ko) | 1992-07-25 |
KR970002489B1 KR970002489B1 (ko) | 1997-03-05 |
Family
ID=6420559
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019910021507A KR970002489B1 (ko) | 1990-12-17 | 1991-11-28 | 수용성 디포스핀의 제조방법 |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP0491240B1 (ko) |
JP (1) | JPH0774226B2 (ko) |
KR (1) | KR970002489B1 (ko) |
AT (1) | ATE124701T1 (ko) |
CA (1) | CA2057252C (ko) |
DE (2) | DE4040314A1 (ko) |
DK (1) | DK0491240T3 (ko) |
ES (1) | ES2077781T3 (ko) |
MX (1) | MX9102466A (ko) |
SG (1) | SG44833A1 (ko) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW248563B (ko) * | 1993-06-29 | 1995-06-01 | Hoechst Ag | |
US5536858A (en) * | 1994-02-12 | 1996-07-16 | Hoffmann-La Roche Inc. | Tetrasulfonated diphosphine compounds and metal complexes thereof for asymmetric catalytic reactions |
DE4427428A1 (de) | 1994-08-03 | 1996-02-29 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
DE19506279A1 (de) * | 1995-02-23 | 1996-08-29 | Hoechst Ag | Sulfonierte Diphosphane und ein Verfahren zu ihrer Herstellung |
CN114380672B (zh) * | 2022-01-10 | 2024-05-28 | 青岛三力本诺新材料股份有限公司 | 一种1,3-丁二烯氢甲酰化制备1,6-己二醛的方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK350383A (da) * | 1982-08-27 | 1984-02-28 | Hoffmann La Roche | Phosphorforbindelser |
FR2549840B1 (fr) * | 1983-07-28 | 1986-03-21 | Rhone Poulenc Sante | Nouvelles phosphines chirales sulfonees, leur preparation et leur emploi en catalyse asymetrique |
FR2550202B1 (fr) * | 1983-08-03 | 1986-03-21 | Rhone Poulenc Rech | Procede de preparation de tri(m-sulfophenyl) phosphine |
FR2561650B1 (fr) * | 1984-03-26 | 1987-10-23 | Rhone Poulenc Rech | Perfectionnement au procede de preparation de tri(m-sulfophenyl)phosphine par hydrolyse et dilution controlees du sulfonat |
-
1990
- 1990-12-17 DE DE4040314A patent/DE4040314A1/de not_active Withdrawn
-
1991
- 1991-11-28 KR KR1019910021507A patent/KR970002489B1/ko not_active IP Right Cessation
- 1991-12-05 AT AT91120871T patent/ATE124701T1/de not_active IP Right Cessation
- 1991-12-05 DK DK91120871.8T patent/DK0491240T3/da active
- 1991-12-05 EP EP91120871A patent/EP0491240B1/de not_active Expired - Lifetime
- 1991-12-05 DE DE59105930T patent/DE59105930D1/de not_active Expired - Fee Related
- 1991-12-05 SG SG1996008372A patent/SG44833A1/en unknown
- 1991-12-05 ES ES91120871T patent/ES2077781T3/es not_active Expired - Lifetime
- 1991-12-09 CA CA002057252A patent/CA2057252C/en not_active Expired - Fee Related
- 1991-12-10 MX MX9102466A patent/MX9102466A/es not_active IP Right Cessation
- 1991-12-10 JP JP3326114A patent/JPH0774226B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
DE4040314A1 (de) | 1992-06-25 |
MX9102466A (es) | 1992-06-01 |
ES2077781T3 (es) | 1995-12-01 |
JPH04290889A (ja) | 1992-10-15 |
EP0491240A1 (de) | 1992-06-24 |
JPH0774226B2 (ja) | 1995-08-09 |
DE59105930D1 (de) | 1995-08-10 |
EP0491240B1 (de) | 1995-07-05 |
DK0491240T3 (da) | 1995-08-21 |
SG44833A1 (en) | 1997-12-19 |
KR970002489B1 (ko) | 1997-03-05 |
CA2057252C (en) | 1996-01-02 |
ATE124701T1 (de) | 1995-07-15 |
CA2057252A1 (en) | 1992-06-18 |
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