US2994714A - Trinitroethyl acrylate - Google Patents

Trinitroethyl acrylate Download PDF

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Publication number
US2994714A
US2994714A US286603A US28660352A US2994714A US 2994714 A US2994714 A US 2994714A US 286603 A US286603 A US 286603A US 28660352 A US28660352 A US 28660352A US 2994714 A US2994714 A US 2994714A
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Prior art keywords
trinitroethyl
compound
acrylate
new
trinitroethyl acrylate
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Expired - Lifetime
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US286603A
Inventor
Robert H Saunders
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    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B25/00—Compositions containing a nitrated organic compound
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
    • C07C205/40—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups and esterified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton

Definitions

  • the new compound of the invention is a liquid at room temperature. It is of particular interest as a polymerizable, high explosive monomer. It has further utility as an intermediate in the preparation of fl-trinitroethyl-ytrinitrobutyrate, a new explosive compound disclosed and claimed in my co-pending application Serial No. 286,601 filed May 7, 1952.
  • the new compound was prepared by reacting acrylyl chloride with trinitroethanol.
  • the invention is illustrated by the following example, but is not limited thereto.
  • Example 181 grams of trinitroethanol and a slight excess of acrylyl chloride were heated for 3 hours at 57 C., then 2,994,714 Patented Aug. 1, 1961 distilled at a low pressure to remove the excess chloride.
  • the crude material which was probably contaminated with trinitroethanol, had a boiling point range of 7090 C. at /2 mm. pressure.
  • the compound has the following formula:
  • the pure compound has an oxygen balance of -31. It has an impact sensitivity of 45, as determined with the Bureau of Mines impact machine, this figure being the distance in centimeters a 2 kilogram weight was required t6 fall in order to produce shots.
  • Trinitroethyl acrylate having the following structural formula:

Description

United States Patent 2,994,714 TRINITROETHY L A'CRYLATE Robert H. Saunders, West Chester, Pa., assignor, by mesne assignments, to the United States of America as represented by the Secretary of the Navy No Drawing. Filed May 7, 1952, Ser. No. 286,603 1 Claim. (Cl. 260486) This invention relates to a new explosive compound, trinitroethyl acrylate.
The new compound of the invention is a liquid at room temperature. It is of particular interest as a polymerizable, high explosive monomer. It has further utility as an intermediate in the preparation of fl-trinitroethyl-ytrinitrobutyrate, a new explosive compound disclosed and claimed in my co-pending application Serial No. 286,601 filed May 7, 1952.
It is an object of the invention to provide a new compound, trinitroethyl acrylate.
The new compound was prepared by reacting acrylyl chloride with trinitroethanol.
The invention is illustrated by the following example, but is not limited thereto.
Example 1.81 grams of trinitroethanol and a slight excess of acrylyl chloride were heated for 3 hours at 57 C., then 2,994,714 Patented Aug. 1, 1961 distilled at a low pressure to remove the excess chloride. The crude material, which was probably contaminated with trinitroethanol, had a boiling point range of 7090 C. at /2 mm. pressure.
The compound has the following formula:
The pure compound has an oxygen balance of -31. It has an impact sensitivity of 45, as determined with the Bureau of Mines impact machine, this figure being the distance in centimeters a 2 kilogram weight was required t6 fall in order to produce shots.
It is thus seen that there has been provided a new explosive compound having utility as a polymerizable, high explosive monomer and as an intermediate in the preparation o-f S-tn'nitroethyl- -trinitrobutyrate.
What is claimed is:
Trinitroethyl acrylate having the following structural formula:
No references cited.
US286603A 1952-05-07 1952-05-07 Trinitroethyl acrylate Expired - Lifetime US2994714A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US286603A US2994714A (en) 1952-05-07 1952-05-07 Trinitroethyl acrylate

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Application Number Priority Date Filing Date Title
US286603A US2994714A (en) 1952-05-07 1952-05-07 Trinitroethyl acrylate

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US2994714A true US2994714A (en) 1961-08-01

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US286603A Expired - Lifetime US2994714A (en) 1952-05-07 1952-05-07 Trinitroethyl acrylate

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3248420A (en) * 1962-04-09 1966-04-26 Aerojet General Co Process for making the acetates of trinitro-aza-alkylnitrates

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3248420A (en) * 1962-04-09 1966-04-26 Aerojet General Co Process for making the acetates of trinitro-aza-alkylnitrates

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