DE1118781B - Process for the preparation of organic compounds containing phosphorus and silicon - Google Patents
Process for the preparation of organic compounds containing phosphorus and siliconInfo
- Publication number
- DE1118781B DE1118781B DEN16250A DEN0016250A DE1118781B DE 1118781 B DE1118781 B DE 1118781B DE N16250 A DEN16250 A DE N16250A DE N0016250 A DEN0016250 A DE N0016250A DE 1118781 B DE1118781 B DE 1118781B
- Authority
- DE
- Germany
- Prior art keywords
- silicon
- hours
- organic compounds
- preparation
- compounds containing
- 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.)
- Pending
Links
- 229910052710 silicon Inorganic materials 0.000 title claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 5
- 239000011574 phosphorus Substances 0.000 title claims description 5
- 150000002894 organic compounds Chemical class 0.000 title claims description 4
- 239000010703 silicon Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000003003 phosphines Chemical group 0.000 claims description 3
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical group S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 150000004756 silanes Chemical class 0.000 claims description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 description 8
- VZZJVOCVAZHETD-UHFFFAOYSA-N diethylphosphane Chemical compound CCPCC VZZJVOCVAZHETD-UHFFFAOYSA-N 0.000 description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UFHILTCGAOPTOV-UHFFFAOYSA-N tetrakis(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)C=C UFHILTCGAOPTOV-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- QRHCILLLMDEFSD-UHFFFAOYSA-N bis(ethenyl)-dimethylsilane Chemical compound C=C[Si](C)(C)C=C QRHCILLLMDEFSD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- QDASGLPLQWLMSJ-UHFFFAOYSA-N dichloro-ethenyl-phenylsilane Chemical compound C=C[Si](Cl)(Cl)C1=CC=CC=C1 QDASGLPLQWLMSJ-UHFFFAOYSA-N 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GQMIGIPYQLWEAU-UHFFFAOYSA-N diethyl(sulfido)phosphanium Chemical compound CCP(=S)CC GQMIGIPYQLWEAU-UHFFFAOYSA-N 0.000 description 1
- WERMRYHPOOABQT-UHFFFAOYSA-N dimethoxy-bis(prop-2-enyl)silane Chemical compound C=CC[Si](OC)(CC=C)OC WERMRYHPOOABQT-UHFFFAOYSA-N 0.000 description 1
- ZDSFBVVBFMKMRF-UHFFFAOYSA-N dimethyl-bis(prop-2-enyl)silane Chemical compound C=CC[Si](C)(C)CC=C ZDSFBVVBFMKMRF-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- JLHMVTORNNQCRM-UHFFFAOYSA-N ethylphosphine Chemical compound CCP JLHMVTORNNQCRM-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- AKRQMTFHUVDMIL-UHFFFAOYSA-N tetrakis(prop-2-enyl)silane Chemical compound C=CC[Si](CC=C)(CC=C)CC=C AKRQMTFHUVDMIL-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- -1 triethyldodecenylsilane Chemical compound 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 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
- C07F9/5004—Acyclic saturated phosphines
- C07F9/5009—Acyclic saturated phosphines substituted by B, Si, P or a metal
-
- 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
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5304—Acyclic saturated phosphine oxides or thioxides
- C07F9/5308—Acyclic saturated phosphine oxides or thioxides substituted by B, Si, P or a metal
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/5406—Silicon-containing compounds containing elements other than oxygen or nitrogen
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)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Die Erfindung behandelt die Herstellung neuer Phosphor und Silicium enthaltender organischer Verbindungen. The invention deals with the preparation of new phosphorus and silicon containing organic compounds.
Die Verbindungen werden dadurch erhalten, daß man sekundäre Phosphine, Phosphinsulfide oder
-oxyde der allgemeinen Formel
R2 The compounds are obtained by adding secondary phosphines, phosphine sulfides or oxides of the general formula
R 2
R1 —Ρ —ΗR 1 -Ρ -Η
IlIl
(Y)
mit ungesättigten Silanen der allgemeinen Formel(Y)
with unsaturated silanes of the general formula
An — Si \— Z — C = CH — R4/4_n A n - Si \ - Z - C = CH - R 4 / n 4 _
umsetzt. Hierin bedeuten R1, R2, R3 und R4 Alkyl-, Cycloalkyl-, Aryl-, Alkaryl- und/oder Aralkylreste, R3 und R4 auch Wasserstoff, Y Schwefel oder Sauerstoff oder Null, A die gleichen Gruppen wie R1 und/oder Alkoxyreste und/oder Halogenatome, Z eine unverzweigte oder verzweigte Kohlenwasserstoffkette mit null bis zehn Gliedern und η — 0 bis 3.implements. Here, R 1 , R 2 , R 3 and R 4 denote alkyl, cycloalkyl, aryl, alkaryl and / or aralkyl radicals, R 3 and R 4 also denote hydrogen, Y sulfur or oxygen or zero, A denote the same groups as R. 1 and / or alkoxy radicals and / or halogen atoms, Z an unbranched or branched hydrocarbon chain with zero to ten members and η - 0 to 3.
Die Addition erfolgt schon ohne Katalysatoren. Zur Verkürzung der Reaktionszeit ist es jedoch vorteilhaft, einen Katalysator, wie radikalbildende Azoverbindungen oder Peroxyde, zu verwenden. Hierbei wird bei mäßig erhöhter Temperatur gearbeitet, vorteilhaft bei 60 bis 120° C. Besonders günstig ist die Verwendung von UV-Bestrahlung, da schon bei kurzer Bestrahlungszeit bei Zimmertemperatur und darunter eine quantitative AdditionThe addition takes place even without catalysts. However, it is to shorten the response time advantageous to use a catalyst such as radical-forming azo compounds or peroxides. This is done at a moderately elevated temperature, advantageously at 60 to 120 ° C. Particularly The use of UV irradiation is favorable, since even a short irradiation time at room temperature and below it a quantitative addition
2525th
3030th
von Phosphor und Silicium enthaltendenof phosphorus and silicon containing
organischen Verbindungenorganic compounds
Anmelder:Applicant:
Koppers Company, Inc.,
Pittsburgh, Pa. (V. St. A.)Koppers Company, Inc.,
Pittsburgh, Pa. (V. St. A.)
Vertreter: Dr. W. Schalk, Dipl.-Ing. P. Wirth,Representative: Dr. W. Schalk, Dipl.-Ing. P. Wirth,
Dipl.-Ing. G. E. M. DannenbergDipl.-Ing. G. E. M. Dannenberg
und Dr. V. Schmied-Kowarzik, Patentanwälte,and Dr. V. Schmied-Kowarzik, patent attorneys,
Frankfurt/M., Große Eschenheimer Str. 39Frankfurt / M., Große Eschenheimer Str. 39
DipL-Chem. Dr. Heinz Niebergall, Frankfurt/M.,
ist als Erfinder genannt wordenDipL-Chem. Dr. Heinz Niebergall, Frankfurt / M.,
has been named as the inventor
erfolgt. Auch tertiäre Amine wirken katalytisch auf die Reaktion.he follows. Tertiary amines also have a catalytic effect on the reaction.
Die Additionsreaktion kann in oder ohne inerte Lösungsmittel, wie Paraffine, Cycloparaffine, Aromate, Äther und cyclische Äther, erfolgen.The addition reaction can take place in or without inert solvents, such as paraffins, cycloparaffins, aromatics, Ethers and cyclic ethers.
An die Verbindungen, in denen der Phosphor noch dreiwertig vorliegt, können Schwefel oder Sauerstoff angelagert werden, wobei die entsprechenden Phosphinsulfide oder -oxyde entstehen. Dies erfolgt entweder direkt durch Behandlung mit Schwefel oder Luft oder anderen Oxydationsmitteln in Gegenwart oder Abwesenheit von inerten Lösungsmitteln.Sulfur or oxygen can be added to the compounds in which the phosphorus is still trivalent are deposited, whereby the corresponding phosphine sulfides or oxides are formed. this happens either directly by treatment with sulfur or air or other oxidizing agents in the presence or absence of inert solvents.
Das allgemeine Reaktionsschema kann wie folgt formuliert werden:The general reaction scheme can be formulated as follows:
R3 R*R 3 R *
ι ιι ι
R2 R 2
Α. —Si—\—Z —C=CH/4_« + (4 —η) R1 —P-H-Α. —Si - \ - Z —C = CH / 4 _ «+ (4 —η) R 1 —PH-
(Y)(Y)
R3 R*R 3 R *
R1 R 1
n-Si-I —Z —CH-CH-P —R2 n - Si - I - Z - CH - CH - P - R 2
15,2 g Diäthylphosphin und 10,13 g Dimethyldivinylsilan wurden in einem verschlossenen Gefäß unter Stickstoffatmosphäre 30 Stunden mit UV-Licht bestrahlt.15.2 g of diethylphosphine and 10.13 g of dimethyldivinylsilane were in a sealed vessel irradiated with UV light for 30 hours under a nitrogen atmosphere.
109 748/468109 748/468
Beim Destillieren im Vakuum von 3 mm Hg gingen ps ρ i ς η ϊ 17When distilling in a vacuum of 3 mm Hg, ps ρ i ς η ϊ 17
von 155 bis 160° C 20,2 g einer öligen, farblosen " p from 155 to 160 ° C 20.2 g of an oily, colorless " p
Flüssigkeit über, die folgende Formel besaß: 3,70 g (C2 H5 O)3 Si · C H2 C H2 · P (C2 H5)2 wurdenLiquid over which had the following formula: 3.70 g (C 2 H 5 O) 3 Si · CH 2 CH 2 · P (C 2 H 5 ) 2 were
jyfe " '" " ,mit 0,42 g pulverisiertem Schwefel verrührt (Stick-jyf e "'"", mixed with 0.42 g of powdered sulfur (stick
: 5. stoffatmpsphäre). Der Schwefel löste sich unter : 5. Substance atmosphere). The sulfur dissolved
C+TJ «-υ ruciriiru nm Wärmeentwicklung. Die Mischung wurde dann kurzC + TJ «-υ ruciriiru nm heat development. The mixture then became short
M2^. UH2-UH2MUH2UH2-^iIt2 auf 10Qo q erhitzt und destilliert. Man erhielt einM 2 ^. UH 2 -UH 2 MUH 2 UH 2 - ^ iIt 2 heated to 10Q oq and distilled. One received a
farbloses Öl der Formel
: Me " "
Ausbeute: 80% der Theorie. io (C2H5O)3Si · CH2CH2 · P(C2H5J2 colorless oil of the formula
: Me ""
Yield: 80% of theory. io (C 2 H 5 O) 3 Si • CH 2 CH 2 • P (C 2 H 5 J 2
CgCg
Kp.2 = 145 bis 1480C. Ausbeute: 3,12 g = 100%
23 g Diäthylphosphin wurden mit 17,5 g Divinyl- der Theorie. ..
dichlorsilan 24 Stunden mit UV-Licht bestrahlt (in 15Kp 2 = 145 to 148 0 C. Yield:. 3.12 g = 100% 23 g Diäthylphosphin were mixed with 17.5 g divinyl of theory. ..
dichlorosilane irradiated with UV light for 24 hours (in 15
einer Stickstoffatmosphäre). Das hierbei entstehende Beispiel 8a nitrogen atmosphere). The resulting example 8
Öl wurde im Vakuum bei 2 mm Hg destilliert. Von 12 8 g Trimethyka-tf-dimethyl-vinylsilanOil was distilled in vacuo at 2 mm Hg. From 12 8 g of trimethyka-tf-dimethyl-vinylsilane
139 bis 140,50C 2mm Hg gingen 38,6 g einer ^c(CVO -CVi(CVt ϊ139 to 140.5 0 C 2mm Hg went 38.6 g of a ^ c (CVO -CVi (CVt ϊ
viskosen, farblosen Flüssigkeit der Formel (uh3j3mu(uh3j — uü(uh3jviscous, colorless liquid of the formula (uh 3 j 3 mu (uh 3 j - uü (uh 3 j
■ -Q 20 wurden mit 9,0 g Diäthylphosphin 24 Stunden mit■ -Q 20 were with 9.0 g of diethylphosphine for 24 hours
UV-Licht bestrahlt. Das Reaktionsprodukt würdeUV light irradiated. The reaction product would
Ft P cu rn ς; cvs cvi PPt X Stunde auf 150°C erHtzt Das Addukt blieb in Ft P cu rn ς; cvs cvi PPt X hour heated to 150 ° C The adduct remained in
Ht2^-UH2UH2-M-UH2UH2FUt2 Form eines farblosen öles zurück. Ausbeute etwaHt 2 ^ -UH 2 UH 2 -M-UH 2 UH 2 FUt 2 form a colorless oil . Yield about
80«/» der Theorie.
Cl 2580 «/» the theory.
Cl 25
über. Ausbeute: 85 % der Theorie. Beispiel9above. Yield: 85% of theory. Example9
2,5 g Diäthylphosphinsulfid, (C2H5)2P(S)H, wur-2.5 g diethylphosphine sulfide, (C 2 H 5 ) 2 P (S) H, was
Beispiel 3 den mit 3,8 g Triäthoxyvinylsüan 24 Stunden mitExample 3 with 3.8 g of triethoxyvinylsuane for 24 hours
UV-Licht bestrahlt. Das Reaktionsprodukt wurde beiUV light irradiated. The reaction product was at
6,4 g Tetraallylsilan wurden mit 24,8 g Diphenyl- 30 2 Torr destilliert. Zwischen 137 und 140° C gingen
phosphin in einer Stickstoffatmosphäre in Gegenwart dabei 5,5 g des Adduktes
von 0,3 g Azodiisobutyronitril 12 Stunden auf 80? C, „6.4 g of tetraallylsilane were distilled with 24.8 g of diphenyl 30 2 torr. Between 137 and 140 ° C phosphine went in a nitrogen atmosphere in the presence of 5.5 g of the adduct
from 0.3 g of azodiisobutyronitrile 12 hours to 80? C, "
dann 24 Stunden auf 160° C erhitzt.then heated to 160 ° C. for 24 hours.
Das Reaktionsprodukt erstarrte zu einer farblosen ,,„„,, r„ rw prr „.The reaction product solidified to a colorless """" r " rw prr ".
Fettsubstanz. 35 (U2H5O)3M-UH2—UH2-P(U2H5J2 Fatty substance. 35 (U 2 H 5 O) 3 M-UH 2 -UH 2 -P (U 2 H 5 J 2
r, . . , ., in Form eines farblosen Öles über. Ausbeute: 87 0Zor,. . ,., in the form of a colorless oil above. Yield: 87 0 zo
BelsPie14 derTheorie.
28 g Dimethyldiallylsilan wurden mit 36 g Diäthyl- Bels P ie14 of the theory.
28 g of dimethyldiallylsilane were mixed with 36 g of diethyl
phosphin vermischt und 48 Stunden bei Zimmer- Beispiel 10phosphine mixed and 48 hours for Zimmer example 10
temperatur (Stickstoifatmosphäre) mit einer ultra- 40 25,4 g Triäthyldodecenylsilantemperature (nitrogen atmosphere) with an ultra-40 25.4 g triethyldodecenylsilane
violetten Lampe belichtet. Die Destillation führte zur (C H ) Si(CH.) CH = CHexposed violet lamp. The distillation led to (CH) Si (CH.) CH = CH
^tonÄ ?neJ /iskoseQ ™sfSkeit CKp.4 = 170 bis ^^ ^ 9,0 g3Diäthylphosphin 24 Stunden mit ^ to n Ä ? ne J / iskoseQ ™ s fS keit CKp. 4 = 170 to ^^ ^ 9.0 g 3 diethylphosphine 24 hours with
171° C) der folgenden Formel UV-Licht bestrahlt. Das Reaktionsprodukt wurde im171 ° C) of the following formula is irradiated with UV light. The reaction product was im
(C Hg)2 Si [(CHj)3 P (C2 H5)2]2 Vakuum bei 2 Torr 1 Stunde auf 200° C erhitzt. EsHeated (C Hg) 2 Si [(CHj) 3 P (C 2 H 5 ) 2 ] 2 vacuum at 2 torr at 200 ° C for 1 hour. It
Ausbeute· 62 g = 97<Vo der Theorie. bHeb ein farbloses Öl zurück, das die FormelYield · 62 g = 97 <Vo of theory. bTake back a colorless oil that has the formula
(CH3)3Si(CH2)10CH2CH2P(C2H5)2 (CH 3 ) 3 Si (CH 2 ) 10 CH 2 CH 2 P (C 2 H 5 ) 2
ü e 1 s ρ 1 e l 3 besaß. Ausbeute nahezu quantitativ.
4,75 g Vinyltriäthoxysilan wurden mit 2,25 g Diäthylphosphin vermischt und 24Stunden (Stickstoff- 50 Beispiel 11
atmosphäre) mit einer ultravioletten Lampe bestrahlt. 21,8 g Triäthylstyrilsilan
Die Destillation führte zur Bildung einer farblosen ' ^ττ r,H_r,„ „.._, „.
viskosen Flüssigkeit der Formel CeHs CH = Cii Sl(C2Hs)3 ü e 1 s ρ 1 el 3 possessed. Almost quantitative yield.
4.75 g of vinyltriethoxysilane were mixed with 2.25 g of diethylphosphine and dried for 24 hours (nitrogen 50 Example 11
atmosphere) irradiated with an ultraviolet lamp. 21.8 g of triethylstyrilsilane
The distillation led to the formation of a colorless' ^ ττ r , H _ r , "" .._, ".
viscous liquid of the formula C e H s CH = Cii Sl ( C 2 H s) 3
(C Vt a\ <Ji. cvt cvi .T>ic Vt ^ wurden mit 9,0 g Diäthylphosphin 24 Stunden mit (C Vt a \ <Ji. Cvt cvi .T> ic Vt ^ were treated with 9.0 g of diethylphosphine for 24 hours
(U2H5U)3M UH2UH2 P(U2H5J2 55 UV-Licht bestrahlt. Das Reaktionsprodukt wurde im(U 2 H 5 U) 3 M UH 2 UH 2 P (U 2 H 5 J 2 55 irradiated with UV light. The reaction product was in the
Kp.lo = 123 bis 124° C. Ausbeute: 6,9 g = 98°/o Vakuum bei 2 Torr 1 Stunde auf 200° C erhitzt. DasBp. Lo = 123 to 124 ° C. Yield: 6.9 g = 98% vacuum at 2 torr heated to 200 ° C. for 1 hour. That
der Theorie. Addukt blieb in Form eines Öles zurück. Ausbeutethe theory. Adduct remained in the form of an oil. yield
„ . . , - nahezu quantitativ.". . - almost quantitative.
8,85 g Diallyldimethoxysilan wurden mit 9,0 g Di- 6o B e i s ρ ι e 1 128.85 g of diallyldimethoxysilane were mixed with 9.0 g of di- 6o B e i s ρ ι e 1 12
äthylphosphin vermischt und 30 Stunden (Stickstoff-... . 3,8 g Triäthoxyvinylsüan wurden mit 3,72 g Di-ethylphosphine mixed and 30 hours (nitrogen -.... 3.8 g triethoxyvinylsüan were mixed with 3.72 g di-
atmosphäre) mit einer ultravioletten Lampe belichtet. phenylphosphin 36 Stunden mit UV-Licht bestrahlt.atmosphere) exposed to an ultraviolet lamp. phenylphosphine irradiated with UV light for 36 hours.
Die Destillation führte zur Bildung von 14,1 g einer Die Destillation im Vakuum bei 2 mm Hg ergab 5,9 gDistillation resulted in the formation of 14.1 g of a. Distillation in vacuo at 2 mm Hg gave 5.9 g
farblosen viskosen Flüssigkeit der Formel eines zwischen 178 und 179° C übergehenden farb-colorless, viscous liquid with the formula of a color-
[(C2H5)2P(CH2)3]2Si(OCH3)2 6s losen öles der Formel [(C 2 H 5 ) 2 P (CH 2 ) 3 ] 2 Si (OCH 3 ) 2 6s loose oil of the formula
Kp.3 = 182 bis 184aC. Ausbeute: 14,1 g = 79% (C2H5O)3SiCH2CH2P(C2Hg)2 Bp 3 = 182 to 184 a C. Yield: 14.1 g = 79% (C 2 H 5 O) 3 SiCH 2 CH 2 P (C 2 Hg) 2
der Theorie. Ausbeute: 78,5% der Theorie.the theory. Yield: 78.5% of theory.
4,06 g Phenylvinyldichlorsilan wurden mit 1,8 g Diäthylphosphin 30 Stunden mit UV-Licht bestrahlt. Das Reaktionsprodukt wurde bei 2 mm Hg destilliert, wobei zwischen 126 und 127,5° C 5,0 g des farblosen Öles der Formel4.06 g of phenylvinyldichlorosilane were irradiated with 1.8 g of diethylphosphine with UV light for 30 hours. The reaction product was distilled at 2 mm Hg, with 5.0 g of the colorless between 126 and 127.5 ° C Formula oils
Cl
(C2 H6)2 PCH2C H2 — Si C6 H5 Cl
(C 2 H 6 ) 2 PCH 2 CH 2 -Si C 6 H 5
Cl
übergingen. Ausbeute: 85% der Theorie.Cl
passed over. Yield: 85% of theory.
1,36 g Tetravinylsilan wurden mit 7,44 g Diphenylphosphin 48 Stunden mit UV-Licht bestrahlt. Schon nach 2 Stunden Bestrahlungsdauer begann die Ausscheidung eines Festproduktes. Nach 15 Stunden war schon fast alles erstarrt. Das Reaktionsprodukt wurde 30 Minuten bei 2 Torr auf 290° C erhitzt, der Rückstand aus Benzol umkristallisiert und mit Äther nachgewaschen. Die weiße Festsubstanz hatte einen Schmelzpunkt von 208 bis 211° C und die Formel1.36 g of tetravinylsilane and 7.44 g of diphenylphosphine were irradiated with UV light for 48 hours. Nice After 2 hours of irradiation, a solid product began to precipitate. After 15 hours it was Almost everything has already frozen. The reaction product was heated to 290 ° C. for 30 minutes at 2 torr, the residue recrystallized from benzene and washed with ether. The white solid had one Melting point from 208 to 211 ° C and the formula
[(CeH5)2P· CH2CH2],Si
Ausbeute: 5,1 g = 58% der Theorie.[(C e H 5 ) 2 P • CH 2 CH 2 ], Si
Yield: 5.1 g = 58% of theory.
1,36 g Tetravinylsilan wurden mit 3,6 g Diäthylphosphin 48 Stunden mit UV-Licht bestrahlt. Das Reaktionsprodukt wurde danach bei 2 mm Hg destilliert. Zwischen 224,5 und 228° C gingen 4,5 g des farblosen öligen Adduktes1.36 g of tetravinylsilane and 3.6 g of diethylphosphine were irradiated with UV light for 48 hours. That The reaction product was then distilled at 2 mm Hg. Between 224.5 and 228 ° C, 4.5 g of des went colorless oily adduct
[(C2H5)2P-CH2CH2]4Si
über. Ausbeute: 91°/» der Theorie.[(C 2 H 5 ) 2 P-CH 2 CH 2 ] 4 Si
above. Yield: 91% of theory.
Die Verfahrensprodukte können als Bioeide, Textilhilfsmittel, Stabilisatoren, Inhibitoren, Antioxydantien, Schmiermittel, Schmiermittelzusätze, Hydrauliköle, Antischaummittel, Weichmacher, Vulkanisationsbeschleuniger sowie zum Hydrophobieren und Flammfestmachen von Gegenständen Verwendung finden.The process products can be used as organic silk, textile auxiliaries, Stabilizers, inhibitors, antioxidants, lubricants, lubricant additives, hydraulic oils, Antifoam agents, plasticizers, vulcanization accelerators as well as for hydrophobing and flame retarding of objects find use.
Die Produkte, die noch 1 Chloratom oder eine Alkoxygruppe direkt am Siliciumatom gebundenThe products that still have 1 chlorine atom or an alkoxy group bonded directly to the silicon atom
2525th
30 enthalten, werden vorzugsweise als Kettenstopper bei der Hydrolyse und Kondensation von Diorganodichlorsilanen und Diorganodialkoxysilanen verwendet, während die Verbindungen, die noch 3 Chloratome oder Alkoxygruppen am Siliciumatom tragen, bei diesen Kondensationen als Vernetzer wirken. 30 are preferably used as chain stoppers in the hydrolysis and condensation of diorganodichlorosilanes and diorganodialkoxysilanes, while the compounds that still have 3 chlorine atoms or alkoxy groups on the silicon atom act as crosslinkers in these condensations.
Claims (3)
USA.-Patentschrift Nr. 2 843 615.Considered publications:
U.S. Patent No. 2,843,615.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEN16250A DE1118781B (en) | 1959-02-12 | 1959-02-12 | Process for the preparation of organic compounds containing phosphorus and silicon |
| GB479660A GB925721A (en) | 1959-02-12 | 1960-02-11 | Semiorganic compounds containing phosphorus and silicon |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEN16250A DE1118781B (en) | 1959-02-12 | 1959-02-12 | Process for the preparation of organic compounds containing phosphorus and silicon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1118781B true DE1118781B (en) | 1961-12-07 |
Family
ID=7340170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN16250A Pending DE1118781B (en) | 1959-02-12 | 1959-02-12 | Process for the preparation of organic compounds containing phosphorus and silicon |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1118781B (en) |
| GB (1) | GB925721A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5552020A (en) * | 1995-07-21 | 1996-09-03 | Kimberly-Clark Corporation | Tissue products containing softeners and silicone glycol |
| US5730839A (en) * | 1995-07-21 | 1998-03-24 | Kimberly-Clark Worldwide, Inc. | Method of creping tissue webs containing a softener using a closed creping pocket |
| US6156157A (en) * | 1995-07-21 | 2000-12-05 | Kimberly-Clark Worldwide, Inc. | Method for making soft tissue with improved bulk softness and surface softness |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1189441A (en) * | 1966-03-21 | 1970-04-29 | Albright & Wilson Mfg Ltd | Organic Compositions containing Oxidation Retarders |
| US4298541A (en) | 1979-02-12 | 1981-11-03 | Exxon Research & Engineering Co. | Trihydrocarbyl silyl-substituted alkyl diaryl phosphine transition metal complexes and their use as homogeneous catalysts |
| US4450299A (en) * | 1980-10-01 | 1984-05-22 | Exxon Research And Engineering Co. | Homogeneous hydroformylation catalysis with silyl substituted alkyl diaryl phosphine metal complexes |
| US4687874A (en) * | 1980-02-12 | 1987-08-18 | Exxon Research And Engineering Company | Selective hydroformylation process using alkyl diaryl phosphine rhodium carbonyl hydride catalysts |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2843615A (en) * | 1956-05-31 | 1958-07-15 | Gen Electric | Organophosphorus-silicon compositions |
-
1959
- 1959-02-12 DE DEN16250A patent/DE1118781B/en active Pending
-
1960
- 1960-02-11 GB GB479660A patent/GB925721A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2843615A (en) * | 1956-05-31 | 1958-07-15 | Gen Electric | Organophosphorus-silicon compositions |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5552020A (en) * | 1995-07-21 | 1996-09-03 | Kimberly-Clark Corporation | Tissue products containing softeners and silicone glycol |
| US5730839A (en) * | 1995-07-21 | 1998-03-24 | Kimberly-Clark Worldwide, Inc. | Method of creping tissue webs containing a softener using a closed creping pocket |
| US6156157A (en) * | 1995-07-21 | 2000-12-05 | Kimberly-Clark Worldwide, Inc. | Method for making soft tissue with improved bulk softness and surface softness |
Also Published As
| Publication number | Publication date |
|---|---|
| GB925721A (en) | 1963-05-08 |
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