Accession Number:

AD0370133

Title:

A NEW SYNTHESIS FOR 3-CHLORO-2,2',4,4',6,6'-HEXANITROBIPHENYL, PIPICL

Descriptive Note:

Technical rept.,

Corporate Author:

NAVAL ORDNANCE LAB WHITE OAK MD

Personal Author(s):

• Dacons, Joseph C.
• Kamlet, Mortimer J.

Report Date:

1966-01-18

Pagination or Media Count:

22.0

Abstract:

3-Chloro-2,2,4,4,6,6-hexanitrobiphenyl, PIPICL, was prepared by a three-step procedure from picryl chloride and m-chloro- or m-bromoanisole. The first step involved the formation of m-picrylanisole by means of a mixed Ullmann reaction. Using 90 nitric acid and 30 oleum, the picrylanisole was nitrated to 3-methoxy-2,2,4,4,6,6-hexanitrobiphenyl which was in turn converted to PIPICL by treatment with pyridine and phosphorus oxychloride. When m- bromoanisole was used in the Ullmann reaction, the overall yield for the three steps was about 59. The use of m-chloroanisole resulted in a lower yield in the first step and an overall yield of about 52. Several variations in procedure are given for the preparation of m-picrylanisole.

Descriptors:

• *EXPLOSIVES
• REACTION KINETICS
• PHYSICAL PROPERTIES
• SYNTHESIS(CHEMISTRY)
• CRYSTALLIZATION
• PURIFICATION
• CHLORIDES
• ETHERS
• CHLORINATION
• BROMIDES
• NITRATES
• NITRATION
• BIPHENYL
• THIN LAYER CHROMATOGRAPHY

Subject Categories:

• Organic Chemistry
• Ammunition and Explosives

Distribution Statement:

APPROVED FOR PUBLIC RELEASE