Krieble

Submitted by Charles A. Burkhard and Robert H. Krieble Checked by William S. TATLOCKf and Eugene G. Rochowf... 

Krieble, R.H. (1962) Anaerobic Curing Sealant Having Extended Shelf life , US Patent 3,043,820, Rocky Hill, Connecticut. 

Phenol. The manufacture of phenol by the oxidation of benzene is described by Denton (21) and by Simons and McArthur (107). The literature on phenol by the oxidation of cumene is partly covered in the reports of Frank (33), Hawkins (43), and Kharasch (57), mentioned earlier. A brief description and flow sheet of the process is given in Chemical Engineering (16). The patents in this field are mainly held by The Distillers Co., Ltd., Hercules Powder Co., and Allied Chemical and Dye Corp. In this phenol process large amounts of acetone are obtained as a coproduct. It should also be noted that the process may be directed to the production of cumene hydroperoxide and a,a dimethylbenzyl alcohol. Krieble (61) and Kenyon and Boehmer (55) describe the preparation of phenol by the chlorination and sulfonation processes. 

Smith, Ber. 64, 427 (1931), Resolution of df-form Feist, Arch. Pharm. 247, 226 (1909). Synthesis of (-form using cotton fibers Bredig, Gerstner, Biochem. Z. 250, 414 (1932). Asymmetric synthesis Krieble, Wieland, J. Am. 

The author wishes to acknowledge the outstanding contribution to this work of Dr. Christine Cardin, who has provided all the structural data on which this paper relies so heavily. He would also like to thank the coworkers cited in the references for their hard work and many helpful discussions, Dr. Paul R. Raithby for the provision of diffractometer time in the early years and for helpful discussions, the EPSRC, the Krieble fund, and the Reading University Research Endowment Fund for support. 

Vernon Krieble, then a professor at Trinity College in Hartford, Connecticut. Their first use was as threadlocking sealants, to lock nuts on threaded fasteners as a replacement for metal lock washers, and to lock threaded fasteners in tapped holes in metal parts. They were the first products termed sealants to have a viscosity lower than that of water. Today, such anaerobic adhesives and sealants are used in almost all mechanical equipment that is subject to vibration. 

Vernon Krieble, chairman of the Chemistry Department at Trinity College in Hartford, Connecticut, learned about the product through his son, Robert Krieble, who was employed at General Electric. Vernon Krieble found a chemical solution to the problem by using cumene hydroperoxide (I) (see Section XII for all structures) as the initiator and packaging in half-filled oxygen-permeable polyethylene bottles [8]. He licensed the GE patent and in 1954 founded the American Sealants Corporation, which later became Loctite Corporation [9]. At the present time anaerobic adhesives and sealants are manufactured or sold on every continent by more than a dozen companies. Applications in virtually every industry, and technological iimovation, as measured by patent activity, continue unabated. 

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