GB827366A - Improvements in or relating to organoperoxy compounds - Google Patents
Improvements in or relating to organoperoxy compoundsInfo
- Publication number
- GB827366A GB827366A GB3460255A GB3460255A GB827366A GB 827366 A GB827366 A GB 827366A GB 3460255 A GB3460255 A GB 3460255A GB 3460255 A GB3460255 A GB 3460255A GB 827366 A GB827366 A GB 827366A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tert
- silane
- compounds
- butylperoxy
- titanium
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 229910000077 silane Inorganic materials 0.000 abstract 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 3
- 239000010936 titanium Substances 0.000 abstract 3
- 229910052719 titanium Inorganic materials 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 150000002432 hydroperoxides Chemical class 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 239000010703 silicon Chemical group 0.000 abstract 2
- 229910052710 silicon Chemical group 0.000 abstract 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 abstract 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract 1
- 239000012190 activator Substances 0.000 abstract 1
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- -1 amino- Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000007514 bases Chemical class 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 229910001507 metal halide Inorganic materials 0.000 abstract 1
- 150000005309 metal halides Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000004756 silanes Chemical class 0.000 abstract 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- HRGTUZTWTRKVRP-UHFFFAOYSA-N trimethyl(1,2,3,4-tetrahydronaphthalen-1-ylperoxy)silane Chemical compound C1=CC=C2C(OO[Si](C)(C)C)CCCC2=C1 HRGTUZTWTRKVRP-UHFFFAOYSA-N 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 239000008096 xylene Substances 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0894—Compounds with a Si-O-O linkage
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention comprises organoperoxy compounds of the formula RnX(OOR1)m where X is titanium or silicon (see Group IV(a)), R and R1 are alkyl, cycloalkyl or aryl and R may also be hydrogen, n is 0, 1, 2 or 3, m is 1, 2, 3 or 4 and m+n is 4. They are prepared by reacting the metal halide, alkoxide or amino- or hydroxy-compound with an organic hydroperoxide. In the examples: (10) titanium tetra-isopropoxide is condensed with tert.-butyl hydroperoxide in benzene; and (11) titanium tetrachloride is condensed with tert.-butyl hydroperoxide in pentane, in both cases giving a solid containing 30-31% Ti.ALSO:The invention comprises organoperoxy compounds, useful for the polymerization of ethylenically-unsaturated compounds, having the formula RnX(OOR1)m wherein X is silicon or titanium, R and R1 are alkyl, cycloalkyl or aryl and R may also be hydrogen, n is 0, 1, 2 or 3, m is 1, 2, 3 or 4, and m+n is 4. The silanes are prepared by condensing a halo-, amino-, alkoxy- or hydroxysilane with an organic hydroperoxide; in the case of a halosilane, a basic compound such as pyridine or ammonia is preferably present. Reaction occurs rapidly in an inert diluent such as a lower alkane or ether at temperatures from 0 DEG C. to room temperature. Compounds which may be polymerized or copolymerized by these peroxides include styrene, acrylates, vinyl esters, vinyl chloride and vinylidene chloride. The examples describe the preparation of (1) and (2) trimethyl (tert.-butyl- and tert.-amyl-peroxy)silane; (3) trimethyl-(1,1-dimethylbenzylperoxy)silane; (4) diethyl-di-(tert.-butylperoxy)silane; (5) methyl tri-(tert.-butylperoxy)-silane; (6) and (9) tetra-(tert.-butylperoxy)-silane; (7) diphenyl di-(tert.-butylperoxy)-silane; (8) trimethyl - (1,2,3,4 - tetrahydro - 1 - naphthylperoxy)silane; and also the polymerization of styrene in bulk using several of the above compounds, and of methyl methacrylate in bulk and in solution in xylene and pentane, in one case using diethyl-aniline as activator, and, in another, in the presence of titanium tetrachloride.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE553106D BE553106A (en) | 1955-12-02 | ||
| GB3460255A GB827366A (en) | 1955-12-02 | 1955-12-02 | Improvements in or relating to organoperoxy compounds |
| FR1189882D FR1189882A (en) | 1955-12-02 | 1956-11-29 | Organoperoxy compounds, their manufacturing process and polymerization process using |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3460255A GB827366A (en) | 1955-12-02 | 1955-12-02 | Improvements in or relating to organoperoxy compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB827366A true GB827366A (en) | 1960-02-03 |
Family
ID=10367688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3460255A Expired GB827366A (en) | 1955-12-02 | 1955-12-02 | Improvements in or relating to organoperoxy compounds |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE553106A (en) |
| FR (1) | FR1189882A (en) |
| GB (1) | GB827366A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3450686A (en) * | 1964-12-31 | 1969-06-17 | Monsanto Co | Polymerization of ethylene utilizing an organoperoxysilane as the catalyst |
| EP0009070A1 (en) * | 1978-09-25 | 1980-04-02 | Argus Chemical Corporation | t-Octyl silicon peroxides and their use for crosslinking polyethylenes |
-
0
- BE BE553106D patent/BE553106A/xx unknown
-
1955
- 1955-12-02 GB GB3460255A patent/GB827366A/en not_active Expired
-
1956
- 1956-11-29 FR FR1189882D patent/FR1189882A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3450686A (en) * | 1964-12-31 | 1969-06-17 | Monsanto Co | Polymerization of ethylene utilizing an organoperoxysilane as the catalyst |
| EP0009070A1 (en) * | 1978-09-25 | 1980-04-02 | Argus Chemical Corporation | t-Octyl silicon peroxides and their use for crosslinking polyethylenes |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1189882A (en) | 1959-10-07 |
| BE553106A (en) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Steudel et al. | Reactions of Monohaloörganosilanes and Magnesium in Tetrahydrofuran | |
| GB1536468A (en) | Organosilicon compounds | |
| CN106699938B (en) | Under a kind of effect of alkali without ligand atom transfer radical polymerization method | |
| Seyferth et al. | The preparation of polymerizable silanes containing organometallic substituents in the side-chains | |
| GB795772A (en) | Organosilanes | |
| RO82690B (en) | Process for obtaining a catalyst used for alpha-olefins polymerization | |
| GB827366A (en) | Improvements in or relating to organoperoxy compounds | |
| US2530367A (en) | Disproportionation of alkoxysilanes | |
| GB969074A (en) | Polymerization catalyst | |
| GB733571A (en) | Improvements in and relating to organoethynyl organosilanes | |
| GB741094A (en) | Improvements in and relating to organoethynyl hydrolyzable organosilanes | |
| GB573906A (en) | Process for the production of organo substituted silicon compounds | |
| US2997497A (en) | Organo-silicon peroxides and their preparation | |
| JPS5655405A (en) | Polymerization of ethylene | |
| GB733570A (en) | Improvements in and relating to hexaorganoethynyl silicon derivatives | |
| US2894968A (en) | Preparation of organosilicon compounds | |
| US3657302A (en) | Process for the preparation of organosilicon compounds having hydrogen directly bonded to silicon | |
| US3471539A (en) | Method for preparing triorganotin halides and bis(triorganotin) oxides | |
| US3397241A (en) | Process for the economical preparation of br3 organoboron compounds | |
| KR920000793A (en) | Olefin Polymerization Catalyst and Polymerization Method | |
| US3395167A (en) | Preparation of silalactones | |
| US3839382A (en) | Process for the preparation of organochlorostannanes | |
| US3355476A (en) | Organosilicon compounds made from styrenes | |
| US3419592A (en) | Method for making organosiloxane hydrides | |
| US3180882A (en) | Process for producing cyanoalkylsilanes |