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Title: PHOTOCHEMICAL SYNTHESIS OF ORGANIC FLUORINE COMPOUNDS. Period covered: November 15, 1955 to November 14, 1956

Abstract

The purpose of this research work has been to synthesize organic and organo-metallic fluorine compounds with the major objective of obtaining monomers suitable for polymerization into elastomers, plastics, fluids and related material of high thermal and chemical stability. In conjunction with these aims, this Laboratory has synthesized two halogenated pentadienes. Several important four-membered fluorinated ring compounds have been synthesized and their cyclic ethers. To furnish adequate proof of structure and determine the position of unsaturation, the compounds have been halogenated. In the work on alcohols both 1,2-difluoro-2-chloroallyl alcohol and 1,1difluoro-2-bromoallyl alcohol have been synthesized, the first reported synthesis of a fluorinated allyl alcohol ontainable directly from a Grignard reagent. However, synthesis of trifluoroallyl alcohol has not been achieved. Attempts which have been made to synthesize monohydric and polyhydric alcohols indicate that the proposed routes are feasible. A variety of methods have been used in attempts to prepare alpha, bets-unsaturated ketones (Grignard, free-radical, preparation of alkyl lithium derivatives, Friedel-Crafts-type reactions, and preparation of an unsaturated acid) without success. Several of the ketones derived from the addition of a Grignard reagent to Kel-F Acids have been prepared. As intermediates to the preparation of ketones, two alkynes have been made. (auth)

Authors:
;
Publication Date:
Research Org.:
Colorado. Univ., Boulder
OSTI Identifier:
4315225
Report Number(s):
WADC-TR-56-590(Pt.I); AD-14217
NSA Number:
NSA-12-004101
DOE Contract Number:
AF33(616)-3266
Resource Type:
Technical Report
Resource Relation:
Other Information: Project title: RUBBER, PLASTIC, AND COMPOSITE MATERIALS. Task title: SYNTHESIS AND EVALUATION OF NEW POLYMERS. Orig. Receipt Date: 31-DEC-58
Country of Publication:
United States
Language:
English
Subject:
CHEMISTRY; ALCOHOLS; ALKENES; ALUMINUM CHLORIDES; CATALYSIS; CHEMICAL REACTIONS; CONFIGURATION; CYCLOALKANES; ELASTOMERS; ETHERS; FLUIDS; FRIEDEL-CRAFT REACTION; GRIGNARD REAGENTS; HALOGENATION; HALOGENS; KETONES; ORGANIC COMPOUNDS; ORGANIC FLUORINE COMPOUNDS; ORGANOMETALLICS; PHOTOCHEMISTRY; POLYMERIZATION; POLYMERS; PRODUCTION; RUBBER; STABILITY; TEMPERATURE

Citation Formats

Park, J.D., and Lacher, J.R.. PHOTOCHEMICAL SYNTHESIS OF ORGANIC FLUORINE COMPOUNDS. Period covered: November 15, 1955 to November 14, 1956. United States: N. p., 1956. Web.
Park, J.D., & Lacher, J.R.. PHOTOCHEMICAL SYNTHESIS OF ORGANIC FLUORINE COMPOUNDS. Period covered: November 15, 1955 to November 14, 1956. United States.
Park, J.D., and Lacher, J.R.. Wed . "PHOTOCHEMICAL SYNTHESIS OF ORGANIC FLUORINE COMPOUNDS. Period covered: November 15, 1955 to November 14, 1956". United States. doi:.
@article{osti_4315225,
title = {PHOTOCHEMICAL SYNTHESIS OF ORGANIC FLUORINE COMPOUNDS. Period covered: November 15, 1955 to November 14, 1956},
author = {Park, J.D. and Lacher, J.R.},
abstractNote = {The purpose of this research work has been to synthesize organic and organo-metallic fluorine compounds with the major objective of obtaining monomers suitable for polymerization into elastomers, plastics, fluids and related material of high thermal and chemical stability. In conjunction with these aims, this Laboratory has synthesized two halogenated pentadienes. Several important four-membered fluorinated ring compounds have been synthesized and their cyclic ethers. To furnish adequate proof of structure and determine the position of unsaturation, the compounds have been halogenated. In the work on alcohols both 1,2-difluoro-2-chloroallyl alcohol and 1,1difluoro-2-bromoallyl alcohol have been synthesized, the first reported synthesis of a fluorinated allyl alcohol ontainable directly from a Grignard reagent. However, synthesis of trifluoroallyl alcohol has not been achieved. Attempts which have been made to synthesize monohydric and polyhydric alcohols indicate that the proposed routes are feasible. A variety of methods have been used in attempts to prepare alpha, bets-unsaturated ketones (Grignard, free-radical, preparation of alkyl lithium derivatives, Friedel-Crafts-type reactions, and preparation of an unsaturated acid) without success. Several of the ketones derived from the addition of a Grignard reagent to Kel-F Acids have been prepared. As intermediates to the preparation of ketones, two alkynes have been made. (auth)},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Wed Oct 31 00:00:00 EST 1956},
month = {Wed Oct 31 00:00:00 EST 1956}
}

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  • The purpose of this research work has been to synthesize organic and organometallic fluorine compounds with the major objective of obtaining monomers suitable for polymerization into elastomers, plastics, fluids, and related material of high thermal and chemical stability. In conjunction with these aims, a number of diols and cyclic fluorosilanes has been synthesized. At the present time, the structures assigned to several of the synthesized fluorosilanes have not been verified. Further work in the preparations of cyclic didis involving the dimerization reaction of fluoroolefins with alkenes containing functional groups has produced intermediates with interesting fluorescent properties. Initial investigation has beenmore » made of obtaining a monomeric unit with fluorine substitution on the aromatic nucleus. (auth)« less
  • Elastomers of potential interest for high-temperature aircraft tires --- including butyl, silicone rubber, heatstabie'' polyurethane, and Viton A---were studied to determine tensile, wire-cord adhesion, and air-permeability properties at temperatures ranging up to 400 or 500 deg F, and properties of interest in tire development, such as internal friction and running temperature. Most promising wire adhesions were obtained with solicone rubber, which retained 63% of the 75 deg F adhesive strength at 450 deg F, compared with 9% for Hevea. Silicone rubber is the most highly permeable to air; Thiokoi ST, Vyram and butyl have the lowest air permeabilities. Nitrogen appearsmore » to be the most promising of the unreactive gases to use for inflation of high-temperature tires. Type of sulfur crosslink (mono-, di-, or tetrasulfide) had iittle effect on hightemperature propertaes of Hevea. Gamma-irradiation of vulcanized Hevea improved the high-temperature tensile strength. Balata had lower tensile strength than Hevea over the entire range of 73 to 400 deg F, Vyram N-7700 was about equivalent to Vyram N-5400. Polyether-type polyurethane had 400 deg F tensile strength of 60 psi vs. 515 for the --heat-stable'' polyester type. Teflon resin had a tensile strength of 3825 psi at 73 deg F and 980 psi at 600 deg F. Studies on effects of a 4-hour heat-agng at 400 deg F upon burst pressures of a nylon aircraft tire and of a wire tire are described. It is concluded that a 400 deg F tire will require were tirecord an place of organic fabrics used in present tires. A prototype aircraft tire successfully was constructed from silicone rubber and steel wire tirecord. Coating the wire tirecord and the bead wire with a thin layer of partially cured silicone rubber facilitated fabrication of the beads and plies. Experimental butadiene and acrylic polymers containing functional groups were prepared and their hngh-temperature properties were determined. Carboxyl as the functional group gave better results than hydroxyl or epoxy. Best properties at 400 deg F resulted from using a metal oxide--- particularly magnesium oxide or cadmium oxide ---with epoxy resin to cure the carboxy polymers, enabling 400 deg F tensile strengths as high as 1400 psi to be obtained. The advantages of the metal oxide cure ABSTRACTS were obtained with methacrylate rubber (copolymer of butadiene and methyi methacrylate) by curing with barium hydroxide octahydrate, which gave tensile strengths of 4025 psi at 73 deg F and 960 psi at 400 deg F when used in combi-nation with bis( alpha , alpha - dimethylbenzyl) peroxide. In this manner the advantageous high-temperature properties of the metal oxide cure were realized with improved processability compared with the carboxy polymers. It was found that butadiene copolymers can be vulcanized by heat alone at 500 deg F, a GR-S--carbon black mix giving a tensile of 2450 psi: but this crosslinking could only partially be inhibited. Salicylate esters were the most effective inhibi-tors. (auth)« less
  • The literature concerning organic compounds containing Ga has been surveyed, and the properties of all organometallic and organic coordination compounds of Ga are summarized. An annotated bibliography of all references is provided. (auth)