CA2057252A1 - Process for the preparation of water-soluble diphosphines - Google Patents
Process for the preparation of water-soluble diphosphinesInfo
- Publication number
- CA2057252A1 CA2057252A1 CA2057252A CA2057252A CA2057252A1 CA 2057252 A1 CA2057252 A1 CA 2057252A1 CA 2057252 A CA2057252 A CA 2057252A CA 2057252 A CA2057252 A CA 2057252A CA 2057252 A1 CA2057252 A1 CA 2057252A1
- Authority
- CA
- Canada
- Prior art keywords
- water
- preparation
- integer
- alkyl
- carried out
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title abstract 5
- 238000002360 preparation method Methods 0.000 title abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- -1 biaryl compounds Chemical class 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F9/5054—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
- 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
A new process for the preparation of water-soluble diphosphines derived from biaryl compounds is disclosed. The process comprises treating biaryl compounds of the formula in which A is, for example, alkyl or cycloalkyl, R1 is, for example, hydrogen or alkyl or alkoxy radical having 1 to 14 carbon atoms, m is an integer from 0 to 5 and n is an integer from 0 to 4, with a solution of SO3 in sulfuric acid at a temperature from 0 to 60°C. The mixture, which is allowed to react at 20 to 60°C
over a period of 1 to 60 hours with vigorous stirring, is then diluted with water while maintaining a temperature of from 0 to 20°C and the product is isolated. The process is carried out under mild conditions, under which the formation of oxidation products, such as phosphine oxides, is largely suppressed. The process is economical and can be easily carried out industrially.
over a period of 1 to 60 hours with vigorous stirring, is then diluted with water while maintaining a temperature of from 0 to 20°C and the product is isolated. The process is carried out under mild conditions, under which the formation of oxidation products, such as phosphine oxides, is largely suppressed. The process is economical and can be easily carried out industrially.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4040314.9 | 1990-12-17 | ||
| DE4040314A DE4040314A1 (en) | 1990-12-17 | 1990-12-17 | METHOD FOR PRODUCING WATER-SOLUBLE DIPHOSPHANS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2057252A1 true CA2057252A1 (en) | 1992-06-18 |
| CA2057252C CA2057252C (en) | 1996-01-02 |
Family
ID=6420559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002057252A Expired - Fee Related CA2057252C (en) | 1990-12-17 | 1991-12-09 | Process for the preparation of water-soluble diphosphines |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0491240B1 (en) |
| JP (1) | JPH0774226B2 (en) |
| KR (1) | KR970002489B1 (en) |
| AT (1) | ATE124701T1 (en) |
| CA (1) | CA2057252C (en) |
| DE (2) | DE4040314A1 (en) |
| DK (1) | DK0491240T3 (en) |
| ES (1) | ES2077781T3 (en) |
| MX (1) | MX9102466A (en) |
| SG (1) | SG44833A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW248563B (en) * | 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 (en) | 1994-08-03 | 1996-02-29 | Basf Ag | Process for the preparation of aldehydes |
| DE19506279A1 (en) * | 1995-02-23 | 1996-08-29 | Hoechst Ag | Sulfonated diphosphines and a process for their preparation |
| CN114380672B (en) * | 2022-01-10 | 2024-05-28 | 青岛三力本诺新材料股份有限公司 | Method for preparing 1, 6-glyoxal by hydroformylation of 1, 3-butadiene |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK350383A (en) * | 1982-08-27 | 1984-02-28 | Hoffmann La Roche | phosphorus compounds |
| FR2549840B1 (en) * | 1983-07-28 | 1986-03-21 | Rhone Poulenc Sante | NOVEL SULPHONE CHIRAL PHOSPHINES, THEIR PREPARATION AND THEIR USE IN ASYMMETRIC CATALYSIS |
| FR2550202B1 (en) * | 1983-08-03 | 1986-03-21 | Rhone Poulenc Rech | PROCESS FOR THE PREPARATION OF SOR (M-SULFOPHENYL) PHOSPHINE |
| FR2561650B1 (en) * | 1984-03-26 | 1987-10-23 | Rhone Poulenc Rech | IMPROVEMENT IN THE PROCESS FOR THE PREPARATION OF SORF (M-SULFOPHENYL) PHOSPHINE BY CONTROLLED HYDROLYSIS AND DILUTION OF SULFONATE |
-
1990
- 1990-12-17 DE DE4040314A patent/DE4040314A1/en not_active Withdrawn
-
1991
- 1991-11-28 KR KR1019910021507A patent/KR970002489B1/en not_active IP Right Cessation
- 1991-12-05 SG SG1996008372A patent/SG44833A1/en unknown
- 1991-12-05 ES ES91120871T patent/ES2077781T3/en not_active Expired - Lifetime
- 1991-12-05 EP EP91120871A patent/EP0491240B1/en not_active Expired - Lifetime
- 1991-12-05 AT AT91120871T patent/ATE124701T1/en not_active IP Right Cessation
- 1991-12-05 DK DK91120871.8T patent/DK0491240T3/en active
- 1991-12-05 DE DE59105930T patent/DE59105930D1/en not_active Expired - Fee Related
- 1991-12-09 CA CA002057252A patent/CA2057252C/en not_active Expired - Fee Related
- 1991-12-10 JP JP3326114A patent/JPH0774226B2/en not_active Expired - Fee Related
- 1991-12-10 MX MX9102466A patent/MX9102466A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SG44833A1 (en) | 1997-12-19 |
| JPH0774226B2 (en) | 1995-08-09 |
| KR970002489B1 (en) | 1997-03-05 |
| CA2057252C (en) | 1996-01-02 |
| EP0491240A1 (en) | 1992-06-24 |
| DK0491240T3 (en) | 1995-08-21 |
| ATE124701T1 (en) | 1995-07-15 |
| MX9102466A (en) | 1992-06-01 |
| DE59105930D1 (en) | 1995-08-10 |
| EP0491240B1 (en) | 1995-07-05 |
| JPH04290889A (en) | 1992-10-15 |
| ES2077781T3 (en) | 1995-12-01 |
| DE4040314A1 (en) | 1992-06-25 |
| KR920012101A (en) | 1992-07-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |