Isononyl alcohol

Part I Specialty Chemical Monographs http //www. upltd. com Isononol. See Isononyl alcohol Isononyl acetate... 

Hydroformylation is also used for the manufacture of isononyl alcohol and other long-chain alcohols. Isononyl alcohol is made by first hydroformylating 1-octene to isononaldehyde and then hydrogenating the latter. The long-chain alcohols ( 10 to 20 carbon atoms) are used... 

Polygas Olefins. Refinery propylene and butenes are polymerized with a phosphoric acid catalyst at 200°C and 3040—6080 kPa (30—60 atm) to give a mixture of branched olefins up to used primarily in producing plasticizer alcohols (isooctyl, isononyl, and isodecyl alcohol). Since the olefins are branched (75% have two or more CH groups) the alcohols are also branched. Exxon, BASE, Ruhrchemie (now Hoechst), ICl, Nissan, Getty Oil, U.S. Steel Chemicals (now Aristech), and others have all used this olefin source. 

Other Dimer Olefins. Olefins for plasticizer alcohols are also produced by the dimerization of isobutene [115-11-7] 4 8 codimerization of isobutene and / -butene [25167-67-3]. These highly branched octenes lead to a highly branched isononyl alcohol [68526-84-1] product. BASE, Ruhrchemie, ICl, Nippon Oxocol, and others have used this source. 

The propylene-based chemicals, n- and isobutanol and 2-ethyl-1-hexanol [104-76-7] (2-EH) dominate the product spectmm. These chemicals represent 71% of the world s total oxo chemical capacity. In much of the developed world, plasticizers (qv), long based on 2-EH, are more often and more frequendy higher molecular weight, less volatile Cg, and C q alcohols such as isononyl alcohol, from dimerized normal butenes isodecanol, from propylene trimer and 2-propyl-1-heptanol, from / -butenes and aldol addition. Because of the competition from the higher molecular weight plasticizer alcohols,... 

Isomorphic monomers, 19 762 Isoniazid, 25 798 Isonicotinic hydrazide, 21 103 Isonitrile complexes, platinum, 19 656 Isonitrile-nitrile rearrangement, 21 149 Isononanoic acid, physical properties, 5 35t Isononyl alcohol, properties of commercial, 2 12t... 

CH3C00(CH2)2CH(CH3)CH2C(CH3)3, C11H22O2, Mr 186.29, does not occur in nature. Commercial isononyl acetate contains small amounts of by-products. It is a colorless liquid with a woody-fruity odor and is prepared from diisobutene by the 0x0 synthesis, followed by hydrogenation to the alcohol and acetylation. It is used in household perfumery. 

Mitsubishi Kasei introduced a process to manufacture isononyl alcohol, an important PVC (polyvinyl chloride) plasticizer, via the hydroformylation of octenes (a mixture of isomers produced by dimerization of the C4 cut of naphtha cracker or FCC processes).95 First a nonmodified rhodium complex exhibiting high activity and selectivity in the formation of the branched aldehyde is used. After the oxo reaction, before separation of the catalyst, triphenylphosphine is added to the reaction mixture and the recovered rhodium-triphenylphosphine is oxidized under controlled conditions. The resulting rhodium-triphenylphosphine oxide with an activity and selectivity similar to those of the original complex, is recycled and used again to produce isononanal. 

Alcohol Standards. The alcohols chiefly used are the acetylene derivates 1-butanol, 2-ethylbutanol, 1-hexanol, 2-ethylhexanol, and isononyl alcohol produced from octene by the oxo synthesis. 

Butanol 2-ethyl butanol 1-Hexand 2-ethyl hexancl Isononyl alcohol... 

The next development in plasticizer range monohydric alcohols in the sixties was isononyl alcohol. This branched chain oxo alcohol and its ester (DINP) were commercialized in 1968 by Exxon Chemical Co. DINP offered better overall performance than DOP for most uses, as well as significant compound volume cost advantages. As a result, it has grown rapidly in the marketplace as a general purpose (GP) plasticizer. 

Application The Dimersol-X process transforms butenes to octenes, which are ultimately used in the manufacture of plasticizers via iso-nonanol (isononyl alcohol) and diisononyl phthalate units. 

C9H19OOC(CH2)4COOC9H19], A low-volatility plasticizer based on isononyl alcohol. Combustible. 

Baylectrol 4200 1,2-Benzenedlcarboxylic acid, diisononyl ester CCRIS 6195 Diisononyl phthalate DINP DINP2 DINP3 EINECS 2494)79-5 Enj 2065 ENJ 2065 HSDB 4491 Isononyl alcohol, phthalate (2 1) JAY-DINP Jayflex DINP Palatinol DN Palatinol N Phthalic acid, diisononyl ester Phthalisocizer DINP Sansocizer DINP Vesfinol 9 Vestinol NN Vinylcizer 90 Witamol 150. 

C9 Isononyl alcohol, n-butenes dimer derived alcohols... 

In its present commercial form, Dimersol X produces octenes with a low branching index. This product quality allows higher reaction rates in subsequent hydroformylation units engaging octenes. It also leads to less branched isononyl alcohols and better plasticizer quahty for PVC formulation. Furthermore, it should be noticed that Dimersol tmit operation is quite flexible. The catalyst rate can be adjusted to the feed rate to maintain conversion and selectivity. As stated earlier, contamination of the feed can be accommodated partly by an increase in the catalyst injection rate. This contrasts with units using heterogeneous catalysts, where contamination of the feed can be irreversible and purity of the feed has to be higher. 

Polymer plasticization can be achieved either through internal or external incorporation of the plasticizer into the polymer. Internal plasticization involves copolymerization of the monomers of the desired polymer and that of the plasticizer so that the plasticizer is an integral part of the polymer chain. In this case, the plasticizer is usually a polymer with a low Tg. The most widely used internal plasticizer monomers are vinyl acetate and vinylidene chloride. External plasticizers are those incorporated into the resin as an external additive. Typical low-molecular-weight external plasticizers for PVC are esters formed from the reaction of acids or acid anhydrides with alcohols. The acids include ortho- and iso-or terephthalic, benzoic, and trimellitic acids, which are cyclic or adipic, azeleic, sebacic, and phosphoric acids, which are linear. The alcohol may be monohydric such as 2-ethylhexanol, butanol, or isononyl alcohol or polyhydric such as ethylene or propylene glycol. The structures of some plasticizers of PVC are shown in Table 9.1. 

Trimellitates are the esters of trimellitic anhydride (1,2,4-benzenetricarboxy-lic acid anhydride) and are noted for their low volatility. The most frequently used are trioctyl trimellitate (TOTM) and tri-isononyl trimellitate (TINTM). They are included in plastics which have to function at high temperatures for long periods and for PVC cable insulation in combination with phthalates. Phosphorous oxychloride reacts with various aliphatic and aromatic alcohols and phenols (triphenylphosphate) to produce triesters. Tricresyl phosphate was patented as a plasticizer for PVC in 1933, but was later found to be highly toxic and replaced. In addition to their role as plasticizers, phosphate esters, particularly triphenyl phosphate, function as flame retardants. 

---