Ortho-phenylphenol

Adam-Gibbs Model for the Supercooled Dynamics in the Ortho-Terphenyl Ortho-Phenylphenol Mixture. 

Sodium ortZ/o-phenylphenate see also ortho-Phenylphenol)... 

Ortho-phenylphenol, 2.8% o-benzyl-p-chlorophenol, 2.7% xylenols, 1.5% ethyl alcohol, 1.85%... 

Ortho- and/ i ra-phenylphenols are commercially significant biphenyl derivatives that do not involve biphenyl as a starting material. Both are produced as by-products from the hydrolysis of chlorobenzene [108-90-7] with aqueous sodium hydroxide (68). o-Phenylphenol, ie, l,l-biphenyl-2-ol [90-43-7], particularly as its sodium salt, is widely used as a germicide or fungicide. Pi ra-phenylphenol [92-69-3] with formaldehyde forms a resin used in surface coatings. 

In 1988, the United States consumption of monochlorobenzene was 120 million kilograms 42% for the production of nitrochlorobenzenes, 28% for solvent uses, and the remaining 30% for other appHcations such as diphenyl ether, ortho- and i ra-phenylphenols, sulfone polymers, and diphenyldichlorosilane, an intermediate for specialty siHcones. 

Other apphcations for monochlorobenzene include production of diphenyl-ether, ortho- and i ra-phenylphenol, 4,4 -dichlorodiphenylsulfone, which is a primary raw material for the manufacture of polysulfones, diphenyldichlorosilane, which is an intermediate for specialty siUcones, Grignard reagents, and in dinitrochlorobenzene and catalyst manufacture. 

The palladium-catalyzed arylation of 2-phenylphenols and naphthols shows an interesting feature of arylation of C-H bonds, leading to the formation of an (aryl)(aryloxy)palladium(n) intermediate.65,65a,65b The phenolates are suitable as precoordinating groups. The reaction of 2-hydroxybiphenyl with an excess of iodobenzene occurs regioselectively at the two ortho-positions of phenyl group under palladium catalysis (Equation (57)). In the case of 1-naphthol, the peri-position is phenylated (Equation (58)). 

Alkyl aryl ketones are known to be arylated at the a-position of the alkyl groups, via the corresponding enolates, by treatment with aryl halides in the presence of palladium catalysts [4, 9]. The ortho arylation of alkyl aryl ketones is also possible. For example, in the reaction of benzyl phenyl ketones with bromobenzenes, the arylation first occurs at the benzylic position the ortho positions are then arylated via C-H bond cleavage (Eq. 8) [15]. The ortho arylation is believed to occur after coordination of the enol oxygen to ArPd(II), which is followed by ortho palladation as in the reaction of 2-phenylphenols shown in Scheme 2. 

SYNS o-BIPHENYLOL (l,l -BIPHENYL)-2-OL o-DIPHENYLOL DOWCIDE 1 DOWCIDE 1 ANTIMICROBIAL 2-HYDROXYBIFENYL (CZECH) o-HYDROXYBIPHENYL 2-HYDROXYBIPHENYL o-HYDROXYDIPHENYL 2-HYDROXYDIPHENYL KIWI LUSTR 277 NCI-C50351 OPP ORTHO-HYDROXYDIPHENYL ORTHOPHENYL-PHENOL ORTHOXENOL o-PHENYLPHENOL 2-PHENYL-PHENOL PREVENTOL O EXTRA REMOL TRF TETROSIN OE TORSITE TUMESCAL OPE USAF EK-2219 o-XENOL... 

SODIUM, (2-BIPHENYLYLOXY)- SODIUM 2-HYDROXYDIPHENYL SODIUM ORTHO PHENYLPHENATE SODIUM o-PHENYLPHENATE SODIUM 2-PHENYLPHENATE SODIUM o-PHENYLPHENOL SODIUM o-PHENYLPHENOLATE... 

Arylations of phenols with palladium catalysts are preparatively valuable mainly when using substituted 2-phenylphenols, since otherwise difficult to separate mixtures of oligoarylated products were obtained [43]. The problem was addressed by the application of rhodium catalysts. Thus, the use of P(lPr)2(OAr) (21) as a co-catalyst allowed for the selective ortho-arylation ofa variety of 2-substituted phenols such as 18 with the aryl bromide 19 in good to excellent yields (Scheme 9.10) [44]. 

It has beeia found by Britton that when an aryl or alkyl-substituted aromatic halohydrocarbon is hydrolyzed at a relatively high temperature, i.e., 30(MOO C, in the absence of copper, there is formed a substituted phenol in which the hydroxyl group is in a position that is ortho or para to the (Higinal position of the halogen, together with a certain amount of the expected phenol. For example, both o-phenylphenol and p-phenyl-phenol are prepared from o-chlorobiphenyl. 

After the phenoxide solU tion is discharged from the autoclave, it is extracted with chlorobenzene to remove all alkaii-insoluble material, viz., diphenyl ether and phenyl xenyl etter. The reaction mass is then acidified with hydrochloric acid to neutralize excess caustic and to liberate the phenols. The aqueous layer is put through a steaming-out tower to recover all dissolved phenol. The phenol layer is distilled to recover phenol, following which distillation is continued to rescover ortho- and para-phenylphenols which are further purified for sale. 

The first product of the interesting pentaphenylation is o-phenylphenol (50). It was found that o-phenylphenol (50) undergoes not only monophenylation, but also diphenylation on treatment with iodobenzene at the C-2 positions to give 51 and 52 by the use of PdCb and CS2CO3. The fact that the monoarylated product 51 (25 %) and the diarylated product 52 (62 %) were obtained by the treatment of 2-phenylphenol (50) with 4 equivalents of iodobenzene shows that the arylation of benzene ring is faster than the arylation of ortho carbon of phenol under these conditions [16]. Similarly, when the reaction of bromobenzene with 50 in xylene was stopped after a short time, 2-(biphenyl-2-yl)phenol (51) was obtained in high yield, but 2,6-diphenylphenol was not formed [15]. 

See o-Dichiorobenzene Orthohydroxybenzoic acid. See Saiicyiic acid Orthohydroxydiphenyl. See o-Phenylphenol Ortho Orthocid. See Captan Orthophaitan. See N-Trichloromethylthio phthaiimide... 

Novolak phenolics are made with acid catalysts and ortho- or para-substituted phenols. Molecular weight is controlled by the molar ratio of phenol and formaldehyde, which is always greater than 1. The terminal phenol groups are not metholylated. Alcohol-soluble novolak phenolics derived from o- or p-cresol are used to make novolak epoxy resins. Oil-soluble novolak phenolics made with a substituted phenol, such as p-phenylphenol, are used with dr3ung oils to make varnishes, such as marine spar varnish (see PHENOLIC Resins). 

The reaction of formaldehyde with unsubstituted phenols leads to either soluble or cross-linked resins since condensation occurs at either ortho or para positions. Monosubstituted [35] (ortho or para) phenols give cross-linking with difficulty but phenols doubly substituted in ortho or para positions yield only low molecular weight products. If only one ortho or para position is available on the phenol then the phenol cannot produce resins and reacts with difficulty with aldehydes [33]. Sometimes cresols and phenol are blended together to obtain fully cured resins. In addition to phenol, the other important phenols that are used to give phenolic resins are o-cresol, mixed cresols, / -/e/ r-butylphenol (from isobutylene and phenol), p-phenylphenol (by-product from phenol manufacture), resorcinol, and cardanol (from cashew nutshell liquid). 

The structure of the enzymatically synthesized poly(p-phenylphenol) was analyzed by FT-IR and CP/MAS CNMR spectrometry [114]. The IR spectrum of the polymer indicates that the substitutions on the aromatic ring were at positions 1, 2, 4, and 6 with respect to phorolic-OH. Hienoxy ether linkage was not observed in the spectrum. In CP/MAS CNMR spectrum of the polymer, aU the aromatic signals were broader than those ci the monomer. The major NMR signal at 128 ppm shows that an ortho-substituted product... 

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