GB1025570A - Process for the preparation of phosphines - Google Patents
Process for the preparation of phosphinesInfo
- Publication number
- GB1025570A GB1025570A GB2996163A GB2996163A GB1025570A GB 1025570 A GB1025570 A GB 1025570A GB 2996163 A GB2996163 A GB 2996163A GB 2996163 A GB2996163 A GB 2996163A GB 1025570 A GB1025570 A GB 1025570A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphine
- methyl
- phospholine
- phenyl
- tri
- 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.)
- Expired
Links
- 150000003003 phosphines Chemical class 0.000 title abstract 2
- PGQBTYVHYDZYGW-UHFFFAOYSA-N 3,4-dimethyl-3,4-dihydro-2H-phosphole Chemical compound CC1C=PCC1C PGQBTYVHYDZYGW-UHFFFAOYSA-N 0.000 abstract 2
- OJZDWCDQNYUXQP-UHFFFAOYSA-N 4-methyl-1-phenyl-2,3-dihydrophosphole Chemical compound C1CC(C)=CP1C1=CC=CC=C1 OJZDWCDQNYUXQP-UHFFFAOYSA-N 0.000 abstract 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- PTLIZOFGXLGHSY-UHFFFAOYSA-N dibutylphosphane Chemical compound CCCCPCCCC PTLIZOFGXLGHSY-UHFFFAOYSA-N 0.000 abstract 2
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052710 silicon Inorganic materials 0.000 abstract 2
- 239000010703 silicon Substances 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- SLESMSCUKLYOGC-UHFFFAOYSA-N 1-[bis[(2-methoxyphenyl)methyl]phosphorylmethyl]-2-methoxybenzene Chemical compound COC1=CC=CC=C1CP(=O)(CC=1C(=CC=CC=1)OC)CC1=CC=CC=C1OC SLESMSCUKLYOGC-UHFFFAOYSA-N 0.000 abstract 1
- MOKNNLQTEKLAGF-UHFFFAOYSA-N 1-[butyl(methoxy)phosphoryl]butane Chemical compound CCCCP(=O)(OC)CCCC MOKNNLQTEKLAGF-UHFFFAOYSA-N 0.000 abstract 1
- CHCRMOGCMYMMKR-UHFFFAOYSA-N 1-[butyl(phenylcarbamoyl)phosphanyl]-N-phenylformamide Chemical compound C1(=CC=CC=C1)NC(=O)P(CCCC)C(NC1=CC=CC=C1)=O CHCRMOGCMYMMKR-UHFFFAOYSA-N 0.000 abstract 1
- VGSVITFVAXDZAL-UHFFFAOYSA-N 1-bis(2-methylphenyl)phosphoryl-2-methylbenzene Chemical compound CC1=CC=CC=C1P(=O)(C=1C(=CC=CC=1)C)C1=CC=CC=C1C VGSVITFVAXDZAL-UHFFFAOYSA-N 0.000 abstract 1
- PEFHKNCJNXTCFM-UHFFFAOYSA-N 1-dibutylphosphanyl-N-phenylformamide Chemical compound C(CCC)P(C(NC1=CC=CC=C1)=O)CCCC PEFHKNCJNXTCFM-UHFFFAOYSA-N 0.000 abstract 1
- KEOJOAVYGLGAIM-UHFFFAOYSA-N 1-diethoxyphosphorylbutane Chemical compound CCCCP(=O)(OCC)OCC KEOJOAVYGLGAIM-UHFFFAOYSA-N 0.000 abstract 1
- CKSRDWCMIXKUAQ-UHFFFAOYSA-N 1-diphenylphosphanyl-n-phenylformamide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(=O)NC1=CC=CC=C1 CKSRDWCMIXKUAQ-UHFFFAOYSA-N 0.000 abstract 1
- NGQKYTFERHBEEM-UHFFFAOYSA-N 1-hydroxy-3,4-dimethyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CC1CP(O)(=O)C=C1C NGQKYTFERHBEEM-UHFFFAOYSA-N 0.000 abstract 1
- NGWDJEVARHOLGV-UHFFFAOYSA-N 3,4-dimethyl-N-phenyl-2,3-dihydrophosphole-1-carboxamide Chemical compound CC1=CP(CC1C)C(NC1=CC=CC=C1)=O NGWDJEVARHOLGV-UHFFFAOYSA-N 0.000 abstract 1
- YMKWWHFRGALXLE-UHFFFAOYSA-N 4-methyl-1-phenyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound C1CC(C)=CP1(=O)C1=CC=CC=C1 YMKWWHFRGALXLE-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- GRFZHWRXXAUCLB-UHFFFAOYSA-M [I-].C1(=CC=CC=C1)[P+]1(C=CCC1)C Chemical compound [I-].C1(=CC=CC=C1)[P+]1(C=CCC1)C GRFZHWRXXAUCLB-UHFFFAOYSA-M 0.000 abstract 1
- BHUMZHDFNOXAMC-UHFFFAOYSA-N [methoxy(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(OC)C1=CC=CC=C1 BHUMZHDFNOXAMC-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical compound CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000004696 coordination complex Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 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
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 abstract 1
- IIOSDXGZLBPOHD-UHFFFAOYSA-N tris(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC IIOSDXGZLBPOHD-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 229910052725 zinc Inorganic materials 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
Phosphines (including ones with phosphorus in a ring) are prepared by reacting a phosphoro compound <FORM:1025570/C2/1> where R1, R2 and R3 each represents alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkaryl or aralkyl optionally substituted by alkoxy or amino, R2 and R3 may also represent -OQ, where Q is hydrogen, alkyl, aryl or a salt-forming atom or group, and either R2 or R3 may represent with R1 a saturated or unsaturated tetracarbon bridge which may be hydrocarbyl-substituted, at elevated temperature with an organic or inorganic, monomeric or polymeric silane having at least one hydrogen atom bound to silicon, or with a silicon tetrahalide together with hydrogen in the presence of a metal or metal complex hydrogenation catalyst. Specified catalysts are Na, K, Ca, Mg, Al, Zn, Cu, Pd and cobaltcarbonyls. Temperatures of 100-300 DEG C. are preferred. An inert solvent may be used. Pressures up to 200 atm. are mentioned. An inert gas may be present. In examples: triphenyl phosphine is prepared from triphenyl phosphine oxide; tri-o-tolyl phosphine from tri-o-tolyl phosphine oxide; 1-phenyl-3-methyl phospholine from 1-oxo-1- phenyl-3-methyl phospholine; tri-o-anisyl phosphine from tri - o - anisyl phosphine oxide; dibutyl phosphine from methyl dibutylphosphinate; diphenyl phosphine from methyl diphenylphosphinate; 3,4-dimethyl phospholine from 1-oxo-1-hydroxy - 3,4 - dimethyl phospholine; butylphosphine from n-butyl phosphonic acid or diethyl butylphosphonate. 1 - Phenyl - 1 - methyl phospholinium iodide is prepared from 1-phenyl-3-methyl phospholine and methyl iodide (Example 6). Dibutyl phenylcarbamoylphosphine, diphenyl phenylcarbamoylphosphine, 3,4 - dimethyl - 1 - phenylcarbamoylphospholine and bis-(phenylcarbamoyl) butyl phosphine are prepared by the action of phenyl isocyanate on dibutylphosphine, diphenyl phosphine, 3,4-dimethylphospholine and butylphosphine respectively (Examples 8-12).
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 |
|---|---|
| GB1025570A true GB1025570A (en) | 1966-04-14 |
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 Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1054166D Active GB1054166A (en) | 1962-07-31 |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB1025570A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4835202A (en) * | 1987-11-20 | 1989-05-30 | Ciba-Geigy Corporation | (Hydroxyphenyl) phosphine stabilized compositions |
| FR2910474A1 (en) * | 2006-12-21 | 2008-06-27 | Rhodia Recherches & Tech | Preparation of prim. phosphine compounds from phosphonate compounds,involves reduction with organo-hydrogen-siloxane in presence of catalyst, e.g. titanium isopropoxide |
| 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04340118A (en) * | 1990-06-05 | 1992-11-26 | Seiko Epson Corp | Computer |
-
0
- GB GB1054166D patent/GB1054166A/en active Active
-
1963
- 1963-07-29 GB GB2996163A patent/GB1025570A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4835202A (en) * | 1987-11-20 | 1989-05-30 | Ciba-Geigy Corporation | (Hydroxyphenyl) phosphine stabilized compositions |
| FR2910474A1 (en) * | 2006-12-21 | 2008-06-27 | Rhodia Recherches & Tech | Preparation of prim. phosphine compounds from phosphonate compounds,involves reduction with organo-hydrogen-siloxane in presence of catalyst, e.g. titanium isopropoxide |
| WO2008080833A1 (en) * | 2006-12-21 | 2008-07-10 | Rhodia Operations | Method of preparation of a 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1054166A (en) |
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