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Brassylic Acid: Chemical Intermediate from High-Erucic Oils

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Brassylic Acid: Chemical Intermediate from High-Erucic Oils 3989 Purchased by the U.S. Department of Agriculture for official use. Reprinted from I&EC PRODUCT RESEARCH & DEVELOPMENT. Vol. 16. Page 95. March 1977 Copyright 1977 by the American Chemical Society and reprinted by permission of the copyright owner Brassylic Acid: Chemical Intermediate from High-Erucic Oils Kenneth D. Carlson- and Virgil E. Sohns Northern Regional Research Center. Agricultural Research Service. U.S. Department of Agriculture. Peoria. Illinois 61604 R. Beltron Perkins. Jr., and Everett L. Huffman Southern Research Institute. Birmingham. Alabama 35205 Techniques and information derived from laboratory studies of a two-stage cleavage of erucic acid with ozone and oxygen have been translated to a small pilot-scale operation to produce brassylic acid (72-82% yield) of high purity (99 %) with pelargonic acid as a coproduct. The initial ozonolysis phase is yield-limiting while the sec­ ond stage oxidation of ozonolysis intermediates appears to be quantitative. A preliminary cost estimate has been prepared for production of polYJTler-grade brassylic acid from Crambe abyssinica seed oil. The effects of bye product credit and crambe oil cost on the net cost-to-make brassylic acid are illustrated. Introduction In general, the properties of nylon 1313 are similar to those Aliphatic dibasic acids are versatile chemical intermediates. commercial engineering polyamides. nylon 11, 12.610. and 612 Bifunctionality, from which their importance arises. permits (Chern. Eng.. 1969; Chern. Week. 1971; Mod. Plast., 1970), the acids or their derivatives to undergo various reactions for Probably the most straightforward method of producing the preparation or modification of certain polymers. Only a brassylic acid involves oxidative ozonolysis of erucic acid few long-chain a,w-alkanedioic acids have gained commercial (cis-13-docosenoic) (Blackmore and Szatkowski, 1959; Greene importance (Pryde and Cowan. 1972). most notably adipic et aI., 1967; Greiner. 1970; Grynberg et aI., 1970; Holde and Zadek, 1923; Mirchandani and Simonsen, 1927; Nieschlag et (Co), azelaic (Cg), sebacic (C w), and dodecanedioic (C1:!l. Both adipic and dodecanedioic are derived from petroleum feed­ aI., 1967b; Verkade et al.. 1926). Erucic acid has been avail- stocks, whereas azelaic and sebacic are made from vegetable oils. Dibasic acids and their derivatives supply important CH:l(CH.l)7CH=CH(CH~)11CO~H 0" [ .] "d --- IntermedIates markets as plasticizers, lubricants, and hydraulic fluids; in ErUClC aCI alkyd resins, polyurethanes, and polyamides; as monomers for certain copolymers. ~ CH:I(CH2hC02H + H02C(CH2h IC02H First prepared and characterized in the last half of the Pelargonic acid Brassylic acid nineteenth century (Pryde and Cowan, 1972), brassylic acid able from imported rapeseed oil and occurs to the extent of (1,13-tridecanedioic) is the 13-carbon relative of these com­ 55-60% in the seed oil of Crarnbe abyssinica. a domestic in­ mercially important acids. Selected esters of brassylic acid are dustrial crop being promoted by the U.S. Department of Ag­ excellent low-temperature plasticizers for poly(vinyl chloride) riculture (Nieschlag and Wolff, 1971: Tallent, 1972), The (Nieschlag et al.• 1964; 1967a; 1967c; 1969). Reportedly. esters ultimate yield of brassylic acid from erucic acid depends upon of brassylic acid are suitable as lubricants over a wide tem­ conversion efficiencies attwo distinctstages ofthe reaction­ perature range (Critchley, 1962), and the macrocyclic ester. ozonolysis and oxidation. Evaluation of the two stages indi­ ethylene brassylate. has been prepared as a synthetic musk cates that ozonolysis is more important than oxidation in (Chern. Week. 1965; Emery Industries, 1965; Vonasek and determining the final product yield. We also found excellent Trepkova. 1963). Brassylic acid also serves as the dicarboxvlic correlation between bench-scale and small pilot-scale syn­ acid monomer for preparing such polyamides as nylon 1:313 theses of brassylic acid. and nylon 61.3 (Chern. Eng. News, 1972; Greene et al., 1967; Kestler, 1968; Perkins et al., 1969). The inherent low-moisture absorption of these nylons makes them suitable for uses re­ Bench-Scale Studies quiring retention of strength, toughness, abrasion resistance, Ozonolysis. First, consider laboratory ozonolysis experi­ and electrical properties under varying conditions of humidity. ments. Because esters are more easily analyzed by GLC than Ind. Eng. Chern.. Prod. Res. Dev.• Vol. 16. No.1. 1977 9S 9A Hnnannl Istd.j 13A[ -91 :~/'/f l J8=8 8 "u :f""/~~ln·,, ." "- "'- 40 \ \ $'/ft/ '", ~ '. u m A 1 ll... ...11 __a_a_""_:l ._~ o" 60 100 140 30 60 90 120 150 190 220 ­ ~20L n.e, Ilia '" "'- ~[ Figure 1. Product assay as a function of time for the two stages of "" bench-scale oxidative ozonolvsis of methvl erucate (ME) in acetic acid (aliquots hydrogenated bef~re GLC an~ysis). 8He ~) 91, B 131'£ ~~ I \t __LJ l,,- - ~ 10 20 30 R.I••tin na. ~~ Figure 3. GLC of products of ozonolysis of methyl erucate in acetic I...A...A 22E acid. (A) Aldehyde products from hydrogenation of ozonolysis in­ termediates. 12E = methyllaurate, 20E =methyl eicosanoate. (B) --------------- Products from thermal cleavage (glc without hydrogenation) of ozo­ ~ ~l - nolysis intermediates. SHC =octane. 10 20 30 40 50 Rltll1l0D Tuu Figure 2. GLC of products of oxidative ozonolysis of methyl erucate genated (Pd/C). and analyzed in turn by GLC for methyl in acetic acid. (A) Aldehyde products at end of ozonolysis (after hy­ erucate, aldehydes, and acids. The maximum yield of al­ drogenation). (B) Acid products at end of oxidation. dehydes in this run (80-85%) was assumed to occur at 140 min when ozone appeared in the effluent gases and the disap­ pearance of methyl erucate (ME) ceased. In a separate ex­ are the corresponding acids, methyl erucate rather than erucic periment (K. D. Carlson. unpublished), aldehyde yields de­ acid was ozonized, thereby providing bifunctional interme­ creased on continued exposure to ozone after similar indica­ diates with one ester group. Also, the ozonolysis intermediates tions that the reaction was complete. Over-ozonization is to were hydrogenated over Pd/C, and yields of the major alde­ be avoided if maximum yields are expected. In Figure 1 re­ hyde products-nonanal (9A) (see Nomenclature) and methyl sidual "ME" at 140 min is actually methyl behenate (the 12-formyldodecanoate (13AE)-were then determined by saturated analog of methyl erucate) that was present in the GLC (3% OV-101 on Gaschrom Q). This procedure enabled substrate and not resolved from the methyl erucate under our us to isolate the ozonolysis step to evaluate its influence on the GLC conditions. The aldehyde product distribution (ozono­ ultimate yield of brassylic acid. Ozonolysis was controlled by lysis stage of Figure 1) is shown in Figure 2A. monitoring effluent gases from the reactor with an ozone Oxidation, For the run illustrated in Figure I, the oxidation meter, and flow rates of ozone-in-oxygen (2-3%, 40-50 mg/l.) stage was carried out at two temperatures. 65 ± 5 °C for the were adjusted so that ozone absorpion was complete in the first 90 min and 96-100 °C for the remaining time. We found reaction medium until all double bonds were cleaved. The no exotherm at either temperature in these bench-scale oxi­ substrate solutions were 0.67 M in methyl erucate. dations (20 g substrate). Yields of pelargonic (9Ac) and 12­ Preliminary experiments (K. D. Carlson. unpublished) carbomethoxydodecanoic (13AcE) acids reach a maximum evaluated effects of different solvents, temperatures. and at 2.5 h (83-86%) and then remain constant. Since additional ozone exposure times frem which a process evolved that could oxidation beyond 225 min does not lower the yields. we con­ be used efficiently in the pilot plant. Reductive ozonolytic clude that the acids (Figure 2B) are stable to these oxidation cleavage of methyl erucate in glacial acetic acid at 20-24 °C conditions. Direct conversion ofthe aldehydes to acids is ap­ proceeded cleanly. Yields of9A (88-91%) and 13AE (81-85%) parent from the relative product yields at the end of each stage were reproducible and significantly higher than in inert or (Figure ll. and therefore acid yields depend upon aldehyde mixed solvents (K. D. Carlson, unpublished), and it was ap­ and aldehyde precursor yields in the unreduced ozonolysis parent that acetic acid was a good solvent for scale-up studies. products. The ozonolysis step is most difficult and product We next defined the ozonolysis end point in this solvent both losses are more likely to occur during this step than during for maximum conversion of erucic acid and for product yield. subsequent oxidation. Probably one factor responsible for this Similar information was needed for the oxidation stage, i.e., fact is the thermal lability of intermediates during ozonolysis conversion of ozonolysis intermediates to brassylic acid. (Pryde and Cowan. 1971). This lability is illustrated in Figure Figure 1 shows the productdistribution as a function oftime 3. Hydrogenation of the ozonolysis products before GLC for ozonolysis and subsequent oxidation in glacial acetic acid. analysis gives the usual distribution of aldehydes (Figure 3A, Aliquots were removed during the reaction sequence, hydro- 89% yield of9A, 81% yield of 13AE). but direct GLC analysis 96 Ind. Eng. Chern., Prod. Res. Dev.. Vol. 16, No.1, 1977 116 \ \ B A\ ;-0 115 o a6~. 3)c/ ............. \ ........................ - ;;.. ~ \ 114 '\ 111' ,,, ...e fp 11320C :00 9;! 9; ;!! ~ . ~\ -: __ ~~~":t~,._"_. __._ 113 \. 1120~--J.--1Ol...O--'---20l."O-...L-.....,.30~O-...L--4J..OO-..J,..../ Time. Sec Figure 4. (A) Cooling curve for purified brassylic acid. (B) Freezing point of brassylic acid as a function of purity; 0, calibration data: X, pilot-scale data. OlDIE OITSEJI Figure 6. Pilot-scale reactor for ozonolysis-{)xidation. CKiltOll Brassylic acid of >98% purity was recrystallized from toluene to a constant freezing point (113.8 °C, five recrystallizations). After known amounts of pelargonic acid were added to two CIUGE !IISSTllC samples of this presumably pure brassylic acid.
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