Patent US4310699A successfully refreshed from Google Patents.
US4310699A
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Process for synthesizing bis (phenylglyoxyloyl)benzenes usable for manufacturing polyphenylquinoxaline resins
Assignee: IFP Energies nouvelles
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Filing: 1980-05-23
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Granted: 1982-01-12
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Expires: 2000-05-23
Abstract
Abstract Bis (phenylglyoxyloyl) benzenes are manufactured by a method comprising the reaction of terephthalic or isophthalic aldehyde first with a low proportion of an alkali metal cyanide in a solvent, and then with benzaldehyde; the resultant product is oxidized to the desired bis (phenylglyoxyloyl) benzene.
Inventors
- 👤 Guy Rabilloud
- 👤 Bernard Sillion
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 00:54
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/0683; C08G73/0694; C07; C07C; C07C45/00; C07C45/27; C07C45/29; C07C45/292; C07C45/296; C07C45/298; C07C49/00; C07C49/76; C07C49/782; C07C49/784; C08G6/00
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
139 words
A process for preparing a bis-benzoin having the formula ##STR6## said process comprising the steps of: (a) reacting terephthalic or isophthalic aldehyde with an alkali metal cyanide in a molar ratio of cyanide to aldehyde of from 0.3:1 to 1:1 the reaction being effected in a C 1-4 monoalcohol solvent, the amount of solvent being from 1 to 6 liters per mole of said aldehyde; (b) adding to the resultant reaction mixture from step (a) from 3.5 to 6 moles of benzaldehyde per mole of terephthalic or isophthalic aldehyde used in step (a), at a temperature of from 0° to 30° C.; and (c) heating the resultant reaction mixture from step (b) at a temperature of from 50° to 150° C., and recovering the resultant precipitated bis-benzoin; whereby the recovered bis-benzoin is produced in high yield and high purity.
Claim 2
Dependent Claim
139 words
A process for preparing a bis-benzoin having the formula ##STR6## said process comprising the steps of: (a) reacting terephthalic or isophthalic aldehyde with an alkali metal cyanide in a molar ratio of cyanide to aldehyde of from 0.3:1 to 1:1 the reaction being effected in a C 1-4 monoalcohol solvent, the amount of solvent being from 1 to 6 liters per mole of said aldehyde; (b) adding to the resultant reaction mixture from step (a) from 3.5 to 6 moles of benzaldehyde per mole of terephthalic or isophthalic aldehyde used in step (a), at a temperature of from 0° to 30° C.; and (c) heating the resultant reaction mixture from step (b) at a temperature of from 50° to 150° C., and recovering the resultant precipitated bis-benzoin; whereby the recovered bis-benzoin is produced in high yield and high purity.
Claim 3
Dependent Claim
13 words
A process according to claim 1, wherein said C 1-4 monoalcohol is methanol.
Claim 4
Dependent Claim
22 words
A process according to claim 1, wherein in step (a), the molar ratio of cyanide to aldehyde is from 0.6:1 to 1:1.
Claim 5
Dependent Claim
38 words
In a process for preparing 1,4-bis(phenylglyoxyloyl)benzene or 1,3-bis(phenylglyoxyloyl)benzene, which comprises preparing a bis-benzoin of the formula ##STR7## and oxidizing the bis-benzoin to the corresponding bis(phenylglyoxyloyl)benzene, the improvement which comprises preparing said bis-benzoin by the process of claim 1.
Claim 6
Dependent Claim
14 words
A process according to claim 4, wherein the alkali metal cyanide is potassium cyanide.
Claim 7
Dependent Claim
40 words
A process according to claim 4, wherein the operating time of step (b), effected at 0°-30° C., is from 0.5 to 5 hours, and the operating time of step (c), effected at 50°-150° C., is from 3 to 10 hours.
Claim 8
Dependent Claim
13 words
A process according to claim 4, wherein said C 1-4 monoalcohol is methanol.
Claim 9
Dependent Claim
22 words
A process according to claim 4, wherein in step (a), the molar ratio of cyanide to aldehyde is from 0.6:1 to 1:1.
Claim 10
Dependent Claim
14 words
A process according to claim 1, wherein the alkali metal cyanide is potassium cyanide.
Claim 11
Dependent Claim
40 words
A process according to claim 1, wherein the operating time of step (b), effected at 0°-30° C., is from 0.5 to 5 hours, and the operating time of step (c), effected at 50°-150° C., is from 3 to 10 hours.
Claim 12
Dependent Claim
22 words
A process according to claim 4, wherein the said bis-benzoin is oxidized with an oxidizing agent comprising copper acetate and ammonium nitrate.
References Cited (Backward Citations)
US4024067A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-01-11 | 1985-07-13 | 1986-01-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-01-11 | 1989-07-13 | 1990-01-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-01-11 | 1993-07-13 | 1994-01-12 | $7700.00 | Window Closed / Lapsed |