US4116993A
Expired / Lapsed
US
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Process for producing aromatic-containing silicone compounds
Assignee: General Electric Co
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Filing: 1977-07-05
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Granted: 1978-09-26
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Expires: 1997-07-05
Abstract
Abstract An improved process for producing an aromatic containing silicon compound comprising reacting an aromatic organic compound of the formula RX a with a silicon compound of the formula R b ' Si Z 4-b in the presence of molar quantities of Mg and from 0.5 to up to 1 mole of a promoter which is preferably tetrahydrofuran per mole of the aromatic compound where R is preferably phenylene, X is chloro, a is 2, R' is preferably methyl, Z is alkoxy of 1 to 8 carbon atoms and b is equal to 2.
Inventors
- 👤 Ben Alfred Bluestein
- 👤 E. Robert Evans
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 09:11
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/12; C07F7/121; C07F7/122; C07F7/18; C07F7/1804; C07F7/1872; C07F7/1876
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
190 words
An improved process for producing an aromatic containing silicone compound comprising (a) reacting a aromatic organic compound of the formula, RX a with a silicone compound of the formula, R b ' Si Z 4-b in the presence of molar quantities of Mg and from 0.5 up to 1 mole of a promoter per mole of the aromatic compound which is tetrahydrofuran wherein a portion of the reactants are added to the reaction chamber and then adding from 0.1 to 1% by weight of the total reactants of Cu 2 Cl 2 as a coupler and then after a reaction period of time of 1 to 5 hours there is mixed into the reaction mixture the remaining portion of the reactants; and (b) distilling out the desired product where R is selected from the class consisting of monovalent and divalent mononuclear and binuclear aryl radicals, X is chlorine, a is a whole number that varies from 1 to 4, R' is a radical selected from the class consisting of monovalent hydrocarbon radicals. Z is selected from the class consisting of halogen and hydrocarbonoxy radicals and b varies 0 to 3.
Claim 2
Dependent Claim
190 words
An improved process for producing an aromatic containing silicone compound comprising (a) reacting a aromatic organic compound of the formula, RX a with a silicone compound of the formula, R b ' Si Z 4-b in the presence of molar quantities of Mg and from 0.5 up to 1 mole of a promoter per mole of the aromatic compound which is tetrahydrofuran wherein a portion of the reactants are added to the reaction chamber and then adding from 0.1 to 1% by weight of the total reactants of Cu 2 Cl 2 as a coupler and then after a reaction period of time of 1 to 5 hours there is mixed into the reaction mixture the remaining portion of the reactants; and (b) distilling out the desired product where R is selected from the class consisting of monovalent and divalent mononuclear and binuclear aryl radicals, X is chlorine, a is a whole number that varies from 1 to 4, R' is a radical selected from the class consisting of monovalent hydrocarbon radicals. Z is selected from the class consisting of halogen and hydrocarbonoxy radicals and b varies 0 to 3.
Claim 3
Dependent Claim
34 words
The process of claim 1 wherein the reaction in step (a) is carried out at a temperature in the range of 100°-200° C for a period of time varying from 7 to 24 hours.
Claim 4
Dependent Claim
22 words
The process of claim 2 wherein the reaction is carried out at a temperature in the range of 100° to 160° C.
Claim 5
Dependent Claim
22 words
The process of claim 3 wherein there is present at least one mole of Mg for every mole of the aromatic compound.
Claim 6
Dependent Claim
20 words
The process of claim 4 comprising initiating the reaction in step (a) by adding a crystal of an iodine compound.
Claim 7
Dependent Claim
20 words
The process of claim 1 wherein further comprising adding to the initial reaction mixture a crystal of an iodine compound.
Claim 8
Dependent Claim
29 words
The process of claim 1 wherein the second portion of the reactants are added to reaction mixture after a period of reaction time varying from 1 to 5 hours.
Claim 9
Dependent Claim
15 words
The process of claim 1 wherein in the aromatic compound the R radical is phenylene.
Claim 10
Dependent Claim
11 words
The process of claim 8 wherein the aromatic compound is p-dichlorobenzene.
Claim 11
Dependent Claim
34 words
The process of claim 9 wherein in the silicon compound R' is methyl, Z is a radical selected from the class consisting of alkoxy radicals and phenoxy radicals of 1 to 8 carbon atoms.
Claim 12
Dependent Claim
9 words
The process of claim 10 wherein b is 2.
Claim 13
Dependent Claim
23 words
The process of claim 11 wherein the desired reaction product has the formulas, ##STR2## wherein R, R' and Z is as previously defined.
Claim 14
Dependent Claim
18 words
The process of claim 12 wherein the desired product is obtained in at least 50% by weight yield.
Claim 15
Dependent Claim
216 words
An improved process for producing a compound of the formula, ##STR3## in at least 50% yield comprising (a) first adding and reacting a portion of the following ingredients which comprise an aromatic organic compound of the formula, RX a with a silicon compound of the formula, R b ' Si Z 4-b in the presence of at least 2 moles of Mg per mole of the aromatic organic compound and from 0.5 to up to 1 mole of the catalytic promoter tetrahydrofuran per mole of the aromatic organic compound with from 0.1 to 1% by weight of the total reactants of Cu 2 Cl 2 (b) heating the reaction mixture in the range of 100° C to 160° C and (c) then after the reaction has been initiated adding the remaining portion of the ingredients after a period of time varying from 1 to 5 hours from the initial start of the reaction for a total reaction time varying from 7 to 24 hours and (d) distilling out the desired reaction product where R is a phenylene radical, a is 2 such that the aromatic organic compound is p-dichlorobenzene and wherein R' is methyl, Z is selected from the class consisting of alkoxy and phenoxy radicals of 1 to 8 carbon atoms and b is 2.
Claim 16
Dependent Claim
216 words
An improved process for producing a compound of the formula, ##STR3## in at least 50% yield comprising (a) first adding and reacting a portion of the following ingredients which comprise an aromatic organic compound of the formula, RX a with a silicon compound of the formula, R b ' Si Z 4-b in the presence of at least 2 moles of Mg per mole of the aromatic organic compound and from 0.5 to up to 1 mole of the catalytic promoter tetrahydrofuran per mole of the aromatic organic compound with from 0.1 to 1% by weight of the total reactants of Cu 2 Cl 2 (b) heating the reaction mixture in the range of 100° C to 160° C and (c) then after the reaction has been initiated adding the remaining portion of the ingredients after a period of time varying from 1 to 5 hours from the initial start of the reaction for a total reaction time varying from 7 to 24 hours and (d) distilling out the desired reaction product where R is a phenylene radical, a is 2 such that the aromatic organic compound is p-dichlorobenzene and wherein R' is methyl, Z is selected from the class consisting of alkoxy and phenoxy radicals of 1 to 8 carbon atoms and b is 2.
References Cited (Backward Citations)
US3053872A
Cited
US3202634A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-09-25 | 1982-03-27 | 1982-09-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-09-25 | 1986-03-27 | 1986-09-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-09-25 | 1990-03-27 | 1990-09-26 | $7700.00 | Window Closed / Lapsed |