Adding a certain compound to certain chemical reactions, such as: 112-70-9, 1-Tridecanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Recommanded Product: 112-70-9, blongs to alcohols-buliding-blocks compound. Recommanded Product: 112-70-9
EXAMPLE 3 [00079] The following Example describes the condensation esterification of DDDA using methanesulfonic acid catalyst and the preparation of DDDA diester using a mixture of 50 mole % Telomer alcohol-L and 50 mole % Exxal 13. [00080] A 500 mL round bottom flask was charged with 69.06 g DDDA (MW 230.3, 0.3 mole), 130.41 g Telomer alcohol-L (average molecular weight?414, 0.315 mole), 62.37 g Exxal 13 tridecyl alcohol from Exxon (FW?198, 0.315 mole), 0.29 g methanesulfonic acid (MW 96.1, 0.003 mole), and 100 g mixed xylenes. The reaction flask was fitted with an 8 Vigreux column topped with a Dean-Stark trap and condenser. The reaction was heated to reflux to drive off water, which was separated in the Dean-Stark trap, xylene overflow being returned to the reaction flask. The reaction was followed by water removal and by periodic sampling and titration for acid number. [00081] After 10 and ½ hours reaction time, the acid number had decreased to 1.6 mg KOH/g, and the reaction was considered to be complete. [00082] The reaction product was brown. The reaction product was washed, at 70-80 C., with 330 g of 0.2% aqueous sodium hydroxide. Phases were inverted, with a brown aqueous phase on top and the denser ester phase on the bottom. The lower ester phase was very cloudy. After separating the caustic wash, the ester phase was washed three times with 300 mL portions of warm water. The acid number was 0.56 mg KOH/g. [00083] The crude ester was sparged with nitrogen and heated from room temperature to a temperature of 210-220 C. over a period of 90 minutes to remove xylene, water, and other low boilers. [00084] The yield was 215.72 g of a waxy tan solid having an acid number 0.75 mg KOH/g. [00085] The same basic procedure as above was used to prepare other partially fluorinated esters, listed in Table 5. In all cases, the non-fluorinated alcohol was Exxal 13, tridecyl alcohol from Exxon. Due to difficulty obtaining reliable F elemental analysis, ester end groups were also analyzed by 1H NMR. The chemical shift region between 3.5 and 4.5 ppm downfield of tetramethylsilane reveals the CH2 protons attached to the ester oxygen. In the case of Rf, these CH2 protons are cleanly separated and downfield from the CH2 protons of Rh. The relative molar amounts of Rf and Rh can be calculated from the integrals of these two groups. Where elemental analysis and NMR disagree, the NMR method is believed to be more reliable. Table 5. Partially fluorinated esters prepared by condensation esterification using methanesulfonic acid catalyst[TABLE-US-00006] Mole fractionAcid PartiallypartiallynumberWt % FWt %Prepara- Fluorinatedfluorinated(mg(elementalF (bytionDiacidalcoholalcoholKOH/g)analysis)NMR) 9AdipicTelomer0.0250.341.922.6 alcohol-L10AdipicTelomer0.0250.292.253.2 alcohol11AzelaicTelomer0.02501.831.66 Alcohol-L12C14Telomer0.0250.271.391.28 diacidalcohol-L13CorfreeTelomer0.02501.231.39 M1alcohol-L14CorfreeTelomer0.0250.61.321.49 M1alcohol-L15DDDAPoly HEPO0.0250.14.17 alcohol16DDDATelomer0.025 alcohol17DDDATelomer0.0250.552.12.4 alcohol18DDDATelomer0.0250.131.862 alcohol19DDDATelomer0.0230.100 alcohol20DDDATelomer0.024000 alcohol21DDDATelomer0.0250.181.872.1 alcohol-L22DDDATelomer0.1250.243.019.47 alcohol-L23DDDATelomer0.050.2 4.06 alcohol-L24DDDATelomer0.0250.181.821.92 alcohol-L25DDDATelomer0.250.316.6817.3 alcohol-L26DDDATelomer0.50.75134.634.3 alcohol-L27DDDATelomer0.0250.272.363.4 ethoxylate alcohol28SebacicTelomer0.0250.21.581.63 alcohol-L29SubericTelomer0.0250.260.721.91 alcohol-L [00086] FIG. 4 shows the wear and friction performance of a low-F-content material (?2% F), sample 18 in Table 5, in 150N oil. This low-F-content material was completely soluble even at 20% by weight concentration (0.4 wt. percent F). FIG. 5 compares the anti-wear performance of this low-F material to a similar non-fluorinated diester, ditridecyl dodecanedioate (Hatcol 2907, from Hatco), showing the significant improvement in wear performance from only a very small amount of F incorporation. [00087] Anti-wear and friction reducing performance of different chain length diesters from C6 to C14 was compared. All of these non-symmetric, partially fluorinated diesters imparted some benefits, with the longer chain diacids giving the greater benefits. Therefore, the preferred number of carbon atoms in the backbone is 9 or more or the wear scar by the BOCLE test as described herein is less than about 0.75 when the additive is present at about 0.2% fluorine.
The synthetic route of 112-70-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; E. I. du Pont de Nemours and Company; US6734320; (2004); B2;,
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