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(12) Patent Application Publication (10) Pub. No.: US 2009/0018300 A1 Bloom Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2009/0018300 A1 Bloom Et Al US 2009001 8300A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2009/0018300 A1 Bloom et al. (43) Pub. Date: Jan. 15, 2009 (54) MONOMERS AND POLYMERS FROM Related U.S. Application Data BODERVED CARBON (60) Provisional application No. 60/949,091, filed on Jul. (75) Inventors: Paul D. Bloom, Decatur, IL (US); 11, 2007. Padmesh Venkitasubramanian, Publication Classification Decatur, IL (US) (51) Int. Cl. Correspondence Address: COSH 5/00 (2006.01) K&L GATES LLP (52) U.S. Cl. ........................................................ 52.7/102 HENRY W. OLVER BUILDING 535 SMITHFIELD STREET (57) ABSTRACT PITTSBURGH, PA 15222 (US) The present disclosure provides compositions including bio based monomers derived from biological sources for the Syn (73) Assignee: Archer-Daniels-Midland thesis of polymers from bioderived carbon. The monomers Company, Decatur, IL (US) and resulting polymers are comparable to petroleum derived monomers and polymers, but have a carbon isotope ratio (21) Appl. No.: 12/169,248 characteristic of bioderived materials. Methods for synthesiz ing polymers having 100% biobased materials are also dis (22) Filed: Jul. 8, 2008 closed. 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These methods require the measurement of variations in isotopic abundance between CROSS REFERENCE TO RELATED biobased products and petroleum derived products, for APPLICATIONS example, by liquid Scintillation counting, accelerator mass 0001. The application claims the priority benefit of U.S. spectrometry, or high precision isotope ratio mass spectrom Provisional Patent Application 60/949,091, filed Jul. 11, etry. Isotopic ratios of the isotopes of carbon, such as the 2007, the disclosure of the entirety of which is incorporated 'C/°C carbon isotopic ratio or the ''C/°C carbon isotopic by this reference. ratio, can be determined using isotope ratio mass spectrom etry with a high degree of precision. Studies have shown that TECHNICAL FIELD isotopic fractionation due to physiological processes, such as, 0002 The present disclosure provides compositions com for example, CO transport within plants during photosynthe prising biobased monomers derived from biological sources sis, leads to specific isotopic ratios characteristic of natural or for the synthesis of polymers from bioderived carbon. The bioderived compounds. Petroleum and petroleum derived monomers and resulting polymers may be comparable to products have a different carbon isotopic ratio than bio petroleum derived monomers and polymers, but have a car derived products, for example, due to different chemical pro bon isotope ratio characteristic of bioderived materials. cesses and isotopic fractionation during the generation of Methods for synthesizing polymers having up to 100% bio petroleum. In addition, radioactive decay of the unstable ''C based materials are also disclosed. carbon radioisotope leads to different isotope ratios in bio based products compared to petroleum products. Biobased BACKGROUND content of a product may be verified by ASTM International 0003 Acrylate esters may be produced commercially Radioisotope Standard Method D6866. ASTM International from petrochemical sources. For example, in industry, acrylic Radioisotope Standard Method D6866 determines biobased acid is typically synthesized from acrolein through the cata content of a material based on the amount of biobased carbon lytic oxidation of the petroleum derived propylene. Alterna in the material or product as a percent of the weight (mass) of tively, acrylic acid may be industrially synthesized from pet the total organic carbon in the material or product. Both rochemically derived ethylene, carbon monoxide, and water. bioderived and biobased products will have carbon isotope These processes are industrially feasible due to the relatively ratios characteristic of a biologically derived composition, low price of the propylene and ethylene feedstock. Both pro whereas petroleum derived products will have carbon isotope pylene and ethylene are industrial by-products of gasoline ratios characteristic of compositions derived from petro manufacturing, for example, as by-products of fluid cracking chemical sources. of gas oils or steam cracking of hydrocarbons. 0008. The olefin metathesis reaction has become a power 0004. The world's supply of petroleum is being depleted at ful weapon for the coupling of carbon-carbon double bonds. an increasing rate. Eventually, demand for petrochemical Drs. Grubbs, Schrock, and Chauvin shared the 2005 Nobel derived products may outstrip the Supply of available petro Prize in Chemistry for the development of the olefin metathe leum. When this occurs, the market price of petroleum and, consequently, petroleum derived products will likely sis reaction. The generally accepted mechanism for the olefin increase, making products derived from petroleum more metathesis reaction involves a metal carbene acting as a cata expensive and less desirable. As the available supply of petro lyst to metathesize two alkenes into a new alkene through a leum decreases, alternative sources and, in particular, renew metallocyclobutane intermediate. The newly synthesized alk able sources of comparable products will necessarily have to ene contains one methylene carbon from each of the two be developed. starting alkenes. Olefin metathesis catalysts developed by 0005. In an effort to diminish dependence on petroleum Schrock, Grubbs, and others are commercially available, products the United States government enacted the Farm making the olefin metathesis reaction a viable and useful Security and Rural Investment Act of 2002, section 9002 (7 strategy in organic chemistry. Examples of commercially U.S.C. S8102), hereinafter “FRISA', which requires federal available olefin metathesis catalysts include the “Schrock agencies to purchase biobased products for all items costing catalyst” (i.e., |Mo(=CHMe, Ph)(=N-Ar)(OCMe(CF).) over S10,000. In response, the United States Department of , the “1st generation Grubb’s catalyst” (i.e., Ru(=CHPh) Agriculture (“USDA) has developed Guidelines for Desig Cl(PCy), and the "2nd generation Grubb's catalyst” (i.e. nating Biobased Products for Federal Procurement (7 C.F.R. Ru(=CHPh)ClPCys(N,N'-diaryl-2-imidazolidinyl) S2902) to implement FRISA, including the labeling of bio (Me-methyl, Ph phenyl, Ar-aryl, and Cy-cyclohexyl). based products with a “U.S.D.A. Certified Biobased Product” 0009 Olefins, for example, acrylate esters, may be used label. for the synthesis of polymers, for example, by free radical 0006. As used herein, the term “bioderived' means chain polymerization or by ring-opening metathesis polymer derived from or synthesized by a renewable biological feed ization (“ROMP) of cyclic olefins with diacrylates. For stock, Such as, for example, an agricultural, forestry, plant, example, ring-opening metathesis polymerization of cyclic bacterial, or animal feedstock. As used herein, the term “bio olefins with diacrylates for the synthesis of A.B-alternating based means a product that is composed, in whole or in co-polymers are generally described in U.S. Patent Applica significant part, of biological products or renewable agricul tion Publication Nos. 2003/02363.67 and 2003/0236377; and tural materials (including plant, animal and marine materials) Choi et al., in Angewandte Chemie, International Edition, or forestry materials.
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