← Back to Patent Explorer
US4479905A Expired / Lapsed US ⏱️ 0.0 years remaining

Nitration process

Assignee: Ethyl Corp
•
Filing: 1983-09-19
•
Granted: 1984-10-30
•
Expires: 2003-09-19
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

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)

GB837044A Cited
US4251455A Cited
US4417903A Cited

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

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag