23130-42-9Relevant academic research and scientific papers
A potentially general approach to aliphatic ester-derived PVC plasticizers with suppressed migration as sustainable alternatives to DEHP
Pan, Siyu,Hou, Delong,Chang, Jinming,Xu, Zhou,Wang, Songhang,Yan, Sunxian,Zeng, Qi,Wang, Zhonghui,Chen, Yi
, p. 6430 - 6440 (2019)
The safety of flexible polyvinyl chloride (PVC) materials is now being questioned, partially due to allegations that di-(2-ethylhexyl) phthalate (DEHP), the dominant PVC plasticizer, is an endocrine disruptor and a probable carcinogen. As sustainable alternatives, aliphatic ester-derived plasticizers feature low cytotoxicity, biodegradability, and renewability, but they can only partially replace DEHP in PVC formulations because they have a strong tendency to migrate. Here, using epoxidized fatty acid methyl esters and aliphatic diesters as representatives, we demonstrate that covalently attaching one short ester at each α-position of aliphatic esters via Claisen condensation with judiciously selected dialkyl carbonate significantly suppresses their migration from the PVC matrix. In certain scenarios, the engineered plasticizers even migrate at a rate comparable to, or improved beyond that of DEHP. This approach harnesses the α-proton, a structural feature shared by all aliphatic esters, and dialkyl carbonate, an established "green chemical", thus providing a potentially general and green route towards DEHP alternatives with unprecedented performance that may contribute to sustainability of the old and oft-maligned PVC industry.
Monomers and their polymers derived from saturated fatty acid methyl esters and dimethyl carbonate
Kolb, Nicolai,Meier, Michael A. R.
, p. 2429 - 2435 (2012)
In this study, we exploit the alpha-acidity of saturated fatty acid methyl esters (FAMEs) for the direct conversion of these renewable raw materials to malonate derivatives. After deprotonation with sodium hydride in dimethyl carbonate (DMC) as reactive solvent, the ester enolates react with DMC to give the desired products with up to 80% isolated yield. These malonate derivatives, bearing a long aliphatic chain with chain lengths of C6-C 16, were then polymerized to yield polyesters and polyamides. The polyesters were obtained by copolymerization with 1,6-hexanediol and titanium isopropoxide as a catalyst. For the polyamides, 1,6-hexanediamine was used with 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a catalyst. The obtained polyesters are highly viscous and tacky materials with low melting points and a molecular weight range of 9-17 kDa. The polyamides, on the other hand, are high melting polymers with molecular weights from 7-15 kDa.
Preparation method and application of bifurcated halogenated alkyl chain compounds
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Paragraph 0148; 0149; 0150; 0151, (2018/11/26)
The invention discloses a preparation method and an application of bifurcated halogenated alkyl chain compounds. The method comprises the following steps: reacting bromoalkane with dimethyl malonate to obtain single-branch dimethyl malonate; reacting bromoalkane with the obtained single-branch dimethyl malonate to obtain two-branch dimethyl malonate; carrying out selective hydrolysis decarboxylation on the two-branch dimethyl malonate to obtain a hydrolysate; reducing the hydrolysate to obtain primary alcohol; carrying out a bromination reaction on the primary alcohol to obtain a brominated product; reacting the brominated product with ethylene oxide to obtain carbon chain-extended primary alcohol compounds; and carrying out a halogenation reaction on the carbon chain-extended primary alcohol compounds to obtain the bifurcated halogenated alkyl chain compounds with R being a corresponding halogen atom. The method has the advantages of low cost, high yield, simplicity in operation, andeasiness in realization of industrialization. Alkyl chains with different bifurcated lengths are introduced to an organic conjugated polymer, so the pi-pi piling distance between polymers is effectively reduced, the mobility of the polymer is improved.
Catalyst activity and selectivity in the isomerising alkoxycarbonylation of methyl oleate
Christl, Josefine T.,Roesle, Philipp,Stempfle, Florian,Wucher, Philipp,Goettker-Schnetmann, Inigo,Mueller, Gerhard,Mecking, Stefan
supporting information, p. 17131 - 17140 (2014/01/06)
The synthesis of unsymmetrical diphosphine ligands (3 a-g) with an o-tolyl backbone and tert-butyl, adamantyl, cyclohexyl and isopropyl substituents on the phosphorus moiety is described (1,2-(CH2PR2) (PR′2)C6H
