US4479905A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Nitration process
Assignee: Ethyl Corp
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Filing: 1983-09-19
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Granted: 1984-10-30
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Expires: 2003-09-19
Abstract
Abstract A mixture of aliphatic primary monohydric alcohol and alkoxyalkanol is continuously nitrated by reaction with a nitric-sulfuric acid mixture at -10° to 15° C. to yield an organic nitrate mixture containing substantial amounts of alkoxyalkyl nitrate useful as a cetane improver in diesel fuel.
Inventors
- 👤 Gordon G. Knapp
- 👤 Marguerite S. Baylerian
- 👤 Paul D. Seemuth
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 14:45
CPC Classifications
C; C10; C10L; C10L10/00; C10L10/12; C07; C07C; C07C201/00; C07C201/02; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/23; C10L1/231
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
277 words
Continuous process for making an organic nitrate mixture containing a substantial amount of an alkoxyalkyl nitrate, said process comprising: (A) forming an alcohol mixture of (i) about 50-95 wt % of a primary alcohol containing 4 to about 12 carbon atoms and (ii) about 5-50 wt % of an alkoxyalkanol having the structure R'--O R"--.sub.n OH wherein R' is an alkyl group containing 1-12 carbon atoms, R" is a divalent aliphatic hydrocarbon group containing 2-4 carbon atoms and n is an integer from 1-4; (B) forming an acid mixture consisting essentially of about 10-25 weight percent HNO 3 and 50-75 weight percent H 2 SO 4 , the balance being water; (C) concurrently feeding said alcohol mixture and said acid mixture to a reaction zone forming a nitration mixture, said feeding being at a ratio such that (i) the moles of HNO 3 is at least 1.05 times the combined moles of said primary alcohol and said alkoxyalcohol in said alcohol mixture fed to said reaction zone and (ii) the moles of H 2 SO 4 is at least 0.55 times the total moles of water, said primary alcohol and said alkoxyalcohol in the combined alcohol mixture--acid mixture feed, said feeding being at a rate which provides an average residence time in said reaction zone of about 3-10 minutes, said nitration mixture being maintained at a temperature of about -10° C. to 15° C.; (D) removing said nitration mixture from said reaction zone at a rate which maintains a substantially constant nitration mixture volume in said reaction zone; (E) separating an organic nitrate mixture from said organic nitrate mixture containing a substantial amount of an alkoxyalkyl nitrate.
Claim 2
Dependent Claim
277 words
Continuous process for making an organic nitrate mixture containing a substantial amount of an alkoxyalkyl nitrate, said process comprising: (A) forming an alcohol mixture of (i) about 50-95 wt % of a primary alcohol containing 4 to about 12 carbon atoms and (ii) about 5-50 wt % of an alkoxyalkanol having the structure R'--O R"--.sub.n OH wherein R' is an alkyl group containing 1-12 carbon atoms, R" is a divalent aliphatic hydrocarbon group containing 2-4 carbon atoms and n is an integer from 1-4; (B) forming an acid mixture consisting essentially of about 10-25 weight percent HNO 3 and 50-75 weight percent H 2 SO 4 , the balance being water; (C) concurrently feeding said alcohol mixture and said acid mixture to a reaction zone forming a nitration mixture, said feeding being at a ratio such that (i) the moles of HNO 3 is at least 1.05 times the combined moles of said primary alcohol and said alkoxyalcohol in said alcohol mixture fed to said reaction zone and (ii) the moles of H 2 SO 4 is at least 0.55 times the total moles of water, said primary alcohol and said alkoxyalcohol in the combined alcohol mixture--acid mixture feed, said feeding being at a rate which provides an average residence time in said reaction zone of about 3-10 minutes, said nitration mixture being maintained at a temperature of about -10° C. to 15° C.; (D) removing said nitration mixture from said reaction zone at a rate which maintains a substantially constant nitration mixture volume in said reaction zone; (E) separating an organic nitrate mixture from said organic nitrate mixture containing a substantial amount of an alkoxyalkyl nitrate.
Claim 3
Dependent Claim
15 words
A process of claim 1 wherein R" is the group --CH 2 CH 2 --.
Claim 4
Dependent Claim
9 words
A process of claim 2 wherein n is 1.
Claim 5
Dependent Claim
11 words
A process of claim 3 wherein R' contains 2-4 carbon atoms.
Claim 6
Dependent Claim
27 words
A process of claim 4 wherein said acid mixture consists essentially of about 15-25 weight percent HNO 3 and 60-75 weight percent H 2 SO 4 .
Claim 7
Dependent Claim
40 words
A process of claim 5 wherein said ratio of said mixture to said alcohol mixture is such that 1.1-1.5 moles of HNO 3 are fed to said reaction zone for each mole of the total primary alcohol and alkoxyalcohol feed.
Claim 8
Dependent Claim
13 words
A process of claim 6 wherein said primary alcohol contains 5-10 carbon atoms.
Claim 9
Dependent Claim
11 words
A process of claim 7 wherein said alkoxyalkanol is 2-ethoxy ethanol.
Claim 10
Dependent Claim
18 words
A process of claim 8 wherein said alcohol mixture consists essentially of about 20-40 weight percent 2-ethoxy ethanol.
Claim 11
Dependent Claim
25 words
A process of claim 9 wherein said acid mixture is about 18-22 weight percent HNO 3 and 65-70 weight percent H 2 SO 4 .
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-10-30 | 1988-04-30 | 1988-10-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-30 | 1992-04-30 | 1992-10-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-30 | 1996-04-30 | 1996-10-30 | $7700.00 | Window Closed / Lapsed |