GB1054166A - - Google Patents
Info
- Publication number
- GB1054166A GB1054166A GB1054166DA GB1054166A GB 1054166 A GB1054166 A GB 1054166A GB 1054166D A GB1054166D A GB 1054166DA GB 1054166 A GB1054166 A GB 1054166A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tertiary
- specified
- phosphine
- tri
- dichlorosilane
- 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.)
- Active
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000003377 silicon compounds Chemical class 0.000 abstract 3
- 150000003512 tertiary amines Chemical class 0.000 abstract 3
- 101710178035 Chorismate synthase 2 Proteins 0.000 abstract 2
- 101710152694 Cysteine synthase 2 Proteins 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkyl pyridines Chemical class 0.000 abstract 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 2
- 150000003003 phosphines Chemical group 0.000 abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 2
- QOTVFAGFCXDHJR-UHFFFAOYSA-N 2-anilino-4-phenyliminonaphthalen-1-one Chemical compound C=1C(=NC=2C=CC=CC=2)C2=CC=CC=C2C(=O)C=1NC1=CC=CC=C1 QOTVFAGFCXDHJR-UHFFFAOYSA-N 0.000 abstract 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 abstract 1
- WWMYVQLEAVFYAP-UHFFFAOYSA-N 4-ethyl-3,5-dimethylpyridine Chemical compound CCC1=C(C)C=NC=C1C WWMYVQLEAVFYAP-UHFFFAOYSA-N 0.000 abstract 1
- ZFLFQVOTPBCADM-UHFFFAOYSA-N CC[SiH](Br)Br Chemical compound CC[SiH](Br)Br ZFLFQVOTPBCADM-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- HCIHJOTZGZSMLV-UHFFFAOYSA-N Lutinine Natural products O=C1C(=Nc2ccccc2)C=C(Nc3ccccc3)c4ccccc14 HCIHJOTZGZSMLV-UHFFFAOYSA-N 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- WHYRMRWGLUKQTI-UHFFFAOYSA-N chloro(diethoxy)silane Chemical compound CCO[SiH](Cl)OCC WHYRMRWGLUKQTI-UHFFFAOYSA-N 0.000 abstract 1
- SOYVLBDERBHIME-UHFFFAOYSA-N chloro(diethyl)silicon Chemical compound CC[Si](Cl)CC SOYVLBDERBHIME-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- FSUCAIIDBUYEFT-UHFFFAOYSA-N dichloro(ethoxy)silane Chemical compound CCO[SiH](Cl)Cl FSUCAIIDBUYEFT-UHFFFAOYSA-N 0.000 abstract 1
- PFMKUUJQLUQKHT-UHFFFAOYSA-N dichloro(ethyl)silicon Chemical compound CC[Si](Cl)Cl PFMKUUJQLUQKHT-UHFFFAOYSA-N 0.000 abstract 1
- XNAFLNBULDHNJS-UHFFFAOYSA-N dichloro(phenyl)silicon Chemical compound Cl[Si](Cl)C1=CC=CC=C1 XNAFLNBULDHNJS-UHFFFAOYSA-N 0.000 abstract 1
- LEFPWWWXFFNJAA-UHFFFAOYSA-N dicyclohexylphosphorylcyclohexane Chemical compound C1CCCCC1P(C1CCCCC1)(=O)C1CCCCC1 LEFPWWWXFFNJAA-UHFFFAOYSA-N 0.000 abstract 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000012074 organic phase Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000010703 silicon Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 abstract 1
- 239000005052 trichlorosilane Substances 0.000 abstract 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 abstract 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 abstract 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-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
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/509—Preparation; Separation; Purification; Stabilisation by reduction of pentavalent phosphorus derivatives, e.g. -P=X with X = O, S, Se or -P-Hal2
-
- 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
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5435—Cycloaliphatic phosphonium compounds
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/395—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing phosphorus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,054,166. Tertiary phosphines. SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ N.V. May 14, 1965 [May 16, 1964], No. 20470/65. Addition to 1,025,570. Heading C2C. Tertiary phosphines are prepared by reacting a phosphoroxo compound of the formula wherein R 1 , R 2 and R 3 are similar or dissimilar substituted or unsubstituted hydrocarbon groups, either R 2 or R 3 optionally forming a ring with R 1 , with a silicon compound containing at least one Si-H bond and at least one Sihalogen bond in the presence of a tertiary amine. Specified substituents in R 1 , R 2 and R 3 are amino and alkoxy groups. The reaction is effected at elevated temperatures, preferably between 70‹ and 250‹ C., and preferably in the presence of an inert organic solvent, e.g. naphthalene, benzene, toluene, glycol diethyl ether, diethylene glycol dimethyl ether and diphenyl ether and a pressure of from 20 to 200 atm. gauge or more may be used. The silicon compound is preferably used in an amount such that 0À7-1À5 hydrogen atoms bound to silicon are available for each oxygen atom bound to phosphorus and preferably 0À8-1À7 mols. of tertiary amine are used per mole of phosphine oxide. Specified silicon compounds are phenyl dichlorosilane, ethyl dibromo silane, ethyl dichlorosilane, diethyl chlorosilane, ethoxy dichlorosilane, diethoxy chlorosilane and mono-, di- and tri-ehlorosilanes, and specified tertiary amines are trimethyl-, triethyl- or triisopropyl-amine, dimethyl aniline, pyridine and alkyl pyridines such as lutinine, α- or #-collidine, picoline and 3,5-dimethyl-4-ethyl pyridine. Specified tertiary phosphine products are triphenyl-, tricyclohexyl-, tri-n-butyl- and tri-p-methoxyphenyl phosphines. In one of the examples a mixture of tricyclohexyl phosphine oxide, triethylamine and trichlorosilane is refluxed in benzene, NaOH solution is added and the organic phase is separated and mixed with CS 2 to form a tricyclohexyl phosphine/CS 2 adduct from which the free phosphine may be obtained by adding an alcohol, e.g. methanol.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES80694A DE1193942B (en) | 1962-07-31 | 1962-07-31 | Process for the production of tertiary phosphines |
| DES82798A DE1198819B (en) | 1962-12-11 | 1962-12-11 | Process for the production of primary and secondary phosphines |
| DES83481A DE1191812B (en) | 1963-01-29 | 1963-01-29 | Process for the production of phosphines |
| DES83857A DE1198820B (en) | 1963-02-22 | 1963-02-22 | Process for the production of tertiary phosphines |
| DES91131A DE1203773B (en) | 1964-05-16 | 1964-05-16 | Process for the production of tertiary phosphines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1054166A true GB1054166A (en) |
Family
ID=27512284
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1054166D Active GB1054166A (en) | 1962-07-31 | ||
| GB2996163A Expired GB1025570A (en) | 1962-07-31 | 1963-07-29 | Process for the preparation of phosphines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2996163A Expired GB1025570A (en) | 1962-07-31 | 1963-07-29 | Process for the preparation of phosphines |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB1025570A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5630155A (en) * | 1990-06-05 | 1997-05-13 | Seiko Epson Corporation | Portable computer system with mechanism for accumulating mechanical energy for powering the system |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4835202A (en) * | 1987-11-20 | 1989-05-30 | Ciba-Geigy Corporation | (Hydroxyphenyl) phosphine stabilized compositions |
| FR2910474B1 (en) * | 2006-12-21 | 2009-03-06 | Rhodia Recherches & Tech | PROCESS FOR PREPARING PRIMARY PHOSPHINE |
| FR2932181A1 (en) * | 2008-06-05 | 2009-12-11 | Rhodia Operations | Reduction of a functional group containing phosphorus atom in a substrate, comprises placing the substrate in the presence of a siloxane type compound associated with a base catalyst of a metal element |
| CN110343133A (en) * | 2019-07-03 | 2019-10-18 | 闫福全 | A kind of method of reduction method production triphenylphosphine |
-
0
- GB GB1054166D patent/GB1054166A/en active Active
-
1963
- 1963-07-29 GB GB2996163A patent/GB1025570A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5630155A (en) * | 1990-06-05 | 1997-05-13 | Seiko Epson Corporation | Portable computer system with mechanism for accumulating mechanical energy for powering the system |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1025570A (en) | 1966-04-14 |
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