Alcohol phthalates

Results The data in Table II offer the opportunity to compare phthalates of four different eight-carbon alcohols. The performance differences are perhaps greater than would be expected from such simple variations in skeletal makeup. The most notable differences are in volatility and low temperature properties, but other minor differences also exist. Greater linearity leads to increased efficiency (as measured by the 100% modulus), lower volatility, better flexibility at low temperatures, and better resistance to soapy water. In most circumstances, the linear alcohol phthalates are quite similar to straight chain phthalates. This is to be expected in view of the close similarity of structures. (The true value of a plasticizer system must, of course, consider not only oerformance but price. Thus, high efficiency can sometimes be a disadvantage when costs on a pound volume basis are calculated. In other words, a less efficient plasticizer often gives the lowest compound pound volume cost.)... 

The general conclusions drawn in considering the octyl phthalates hold equally well for the decyl phthalates. Here, however, the linear alcohol phthalate is even closer in performance to the straight chain alcohol phthalate. Both the straight chain and the linear product are somewhat less compatible than the conventional oxo phthalate but have higher efficiency, lower volatility, and better flexibility at low temperatures. 

In summary, it can be said that even-numbered linear oxo phthalates are superior in performance to the corresponding conventional oxo phthalates, and in most respects, closely approach the performance of the completely straight chain alcohol phthalates. Odd-numbered linear alcohols produce phthalates which impart some unique combinations of performance properties to vinyl that were previously available only by using composites of several plasticizers. 

As the decade ended, a new monohydric alcohol phthalate based on mixed C7-C9-C11 straight chain and single methyl branched alcohols was introduced by Monsanto Co. The alcohols are produced by the oxo process from straight chain alpha olefins. The phthalate competed directly with 610P, especially in the automotive upholstery market where it gained rapid acceptance. 

As the seventies got underway, the premium price on the GP linear phthalates decreased to where these plasticizers also began to capture a share of the general purpose plasticizer market, particularly if improved low temperature flexibility was important. The phthalate of the Cn fraction of the linear C7-C9-C11 alcohols was introduced by Monsanto and found acceptance in high temperature wire and cable where it competes with branched chain DTDP. In Europe, linear alcohol phthalates based on alcohol blends made by oxonation of cracked wax olefins gained acceptance. These differed from the U.S. linear alcohol blends in having both odd and even carbon chain lengths. 

The use of hydrocarbon plasticizers as partial replacements for monohydric alcohol phthalates may tend to decrease as a result... 

Asbestos, mineral fibre, resins, acetal styrene, alcohols, phthalates, methyl ethyl ketone, toluene, phenol, isocyanates... 

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. 

Chem. Descrip. Linear CjC, alcohol phthalate CAS 68515-42-4 EINECS/ELINCS 271-084-6 Uses Plasticizer for PVC for imitation leather, elec, cables, conveyor belts, coil coatings, profiles, gaskets, tubing Features Enhanced low temp, performance low fogging UV stable Properties Hazen 50 max. clear liq. pract. odorless sol. in common org. soivs. misc. with most of the plasticizers used in processing PVC insol. in water dens. 0.965-0.978 ml (20 C) vise. 43-51 mPa-s-(20 C) acid no. 0.07 max. ref. index 1.480-1.486 (20 C) 99.5% min. ester content 0.1% max. water Diplast 0 [LonzaSpA]... 

Alcohols Phthalate esters Af.Af-dimethyl acetamide Other nitrogenous compounds... 

Phthalates, made by - esterification of phthalic acid anhydride with two moles of an alcohol (C7-C13), are the laigest-volume plasticizers for PVC. The alcohols are predominantly of petrochemical origin (e.g., ethylhexanol). However, straight-chain alcohols, such as octanol (- caprylic alcohol) or decanol (- capric alcohol), which can be derived from RR, are also used. Esters of these have better low-temperature performance and a lower viscosity than the branched-alcohol phthalates. Their lower volatility has led to their application in flexible PVC, especially in the automotive industry, to avoid fogging , which is the unwanted condensation of plasticizers on the windshield. These properties often compensate for their higher price. Do-decanol is employed in phthalates, where good high-temperature performanee is demanded. 

If, however, the sodium hydroxide is removed by allowing it to react with excess of an ester of high boiling point, such as ethyl succinate or ethyl phthalate, super-dry ethyl alcohol may be obtained ... 

If the perfectly anhydrous alcohols are required, the redistilled alcohol may be treated with the appropriate alkyl phthalate or succinate as already detaUed under Ethyl alcohol (5). 

MC.-Octyl alcohol methyl n-hexyl carbinol CH3CH(OH)(CHj)jCH3 = CgH,OH is converted by heating with phthalic anhydride into sec.-octyl hydrogen phthalate ... 

The latter upon decomposition with dilute hydrochloric acid yields laevo sec.-octyl hydrogen phthalate the crystalline brucine salt, when similarly treated, affords the dextro sec.-octyl hydrogen phthalate. These are reerystallised and separately hydrolysed with sodium hydroxide solution to yield pure I- and d-sec.-octyl alcohols ... 

Alcohol B.P. M.P, 3 5-Dinitro-benzoate p-Nilro- bemoate Phenyl- urethane a-Naph- thyl- urethane Hydrogen 3-nitro- phthalate other Derivatives... 

Chlorine Ammonia, acetylene, alcohols, alkanes, benzene, butadiene, carbon disulflde, dibutyl phthalate, ethers, fluorine, glycerol, hydrocarbons, hydrogen, sodium carbide, flnely divided metals, metal acetylides and carbides, nitrogen compounds, nonmetals, nonmetal hydrides, phosphorus compounds, polychlorobi-phenyl, silicones, steel, sulfldes, synthetic rubber, turpentine... 

ALCOHOLS,HIGHERALIPHATIC - SURVEY AND NATURALALCOHOLSMANUFACTURE] (Voll) Diisodecyl phthalate [68515-49-1]... 

By far the largest volume synthetic alcohol is 2-ethylexanol [104-76-7] CgH gO, used mainly in production of the poly(vinyl chloride) plasticizer bis(2-ethylhexyl) phthalate [117-81-7], commonly called dioctyl phthalate [117-81-7] or DOP (see Plasticizers). A number of other plasticizer... 

Aldehydes fiad the most widespread use as chemical iatermediates. The production of acetaldehyde, propionaldehyde, and butyraldehyde as precursors of the corresponding alcohols and acids are examples. The aldehydes of low molecular weight are also condensed in an aldol reaction to form derivatives which are important intermediates for the plasticizer industry (see Plasticizers). As mentioned earlier, 2-ethylhexanol, produced from butyraldehyde, is used in the manufacture of di(2-ethylhexyl) phthalate [117-87-7]. Aldehydes are also used as intermediates for the manufacture of solvents (alcohols and ethers), resins, and dyes. Isobutyraldehyde is used as an intermediate for production of primary solvents and mbber antioxidants (see Antioxidaisits). Fatty aldehydes Cg—used in nearly all perfume types and aromas (see Perfumes). Polymers and copolymers of aldehydes exist and are of commercial significance. 

Absolutes. Absolutes are prepared from concretes by further processing to remove materials that can cause solubihty problems in perfumes. This is done by dissolution in alcohol, filtering, and removal of the solvent, usually at reduced pressures. The resulting products are viscous, oily materials which may be diluted with low odor substances such as diethyl phthalate. 

Uses. Phthabc anhydride is used mainly in plasticizers, unsaturated polyesters, and alkyd resins (qv). PhthaUc plasticizers consume 54% of the phthahc anhydride in the United States (33). The plasticizers (qv) are used mainly with poly(vinyl chloride) to produce flexible sheet such as wallpaper and upholstery fabric from normally rigid polymers. The plasticizers are of two types diesters of the same monohydric alcohol such as dibutyl phthalate, or mixed esters of two monohydric alcohols. The largest-volume plasticizer is di(2-ethylhexyl) phthalate [117-81-7] which is known commercially as dioctyl phthalate (DOP) and is the base to which other plasticizers are compared. The important phthahc acid esters and thek physical properties are Hsted in Table 12. The demand for phthahc acid in plasticizers is naturally tied to the growth of the flexible poly(vinyl chloride) market which is large and has been growing steadily. 

Commodity Phthalate Esters. The family of phthalate esters are by far the most abundandy produced woddwide. Both orthophthaUc and terephthahc acid and anhydrides are manufactured. The plasticizer esters are produced from these materials by reaction with an appropriate alcohol (eq. 1) terephthalate esterification for plasticizers is performed more abundandy in the United States. Phthalate esters are manufactured from methanol (C ) up to Qyj alcohols, although phthalate use as PVC plasticizers is generally in the range to The lower molecular weight phthalates find use in nitrocellulose the higher phthalates as synthetic lubricants for the automotive industries. 

DiisononylPhthalate andDiisodeeylPhthalate. These primary plasticizers are produced by esterification of 0x0 alcohols of carbon chain length nine and ten. The 0x0 alcohols are produced through the carbonylation of alkenes (olefins). The carbonylation process (eq. 3) adds a carbon unit to an alkene chain by reaction with carbon monoxide and hydrogen with heat, pressure, and catalyst. In this way a Cg alkene is carbonylated to yield a alcohol a alkene is carbonylated to produce a C q alcohol. Due to the distribution of the C=C double bond ia the alkene and the varyiag effectiveness of certain catalysts, the position of the added carbon atom can vary and an isomer distribution is generally created ia such a reaction the nature of this distribution depends on the reaction conditions. Consequendy these alcohols are termed iso-alcohols and the subsequent phthalates iso-phthalates, an unfortunate designation ia view of possible confusion with esters of isophthaUc acid. 

Plasticizer Efficiency. This is a measure of the concentration of plasticizer required to impart a specified softness to PVC. Such a softness of material may be measured as a British Standard Softness (BSS) or a Shore hardness (Pig. 1). Por a given acid constituent of plasticizer ester, ie, phthalate, adipate, etc, plasticizer efficiency decreases as the carbon number of the alcohol chain increases, eg, for phthalate esters efficiency decreases in the order DBP > DIHP > DOP > DINP > DIDP > DTDP. An additional six parts per hundred in PVC of DIDP rather than DOP is required to give a hardness of Shore 80 when ah. other formulation ingredients remain constant. The consequence of this depends on the overall formulation and product costs. In addition to size of the carbon number of the alcohol chain, the amount of branching is also significant the more linear isomers are of greater efficiency. 

Choice of the acid constituent can also be significant. For equivalent alcohol constituents, phthalate and adipate esters are approximately equivalent but both are considerably more efficient than the trimeUitate equivalent. 

Ahyl alcohol undergoes reactions typical of saturated, aUphatic alcohols. Ahyl compounds derived from ahyl alcohol and used industriahy, are widely manufactured by these reactions. For example, reactions of ahyl alcohol with acid anhydrides, esters, and acid chlorides yield ahyl esters, such as diahyl phthalates and ahyl methacrylate reaction with chloroformate yields carbonates, such as diethylene glycol bis(ahyl carbonate) addition of ahyl alcohol to epoxy groups yields products used to produce ahyl glycidyl ether (33,34). 

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