- Direct Enzymatic Synthesis of Fatty Amines from Renewable Triglycerides and Oils
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Fatty amines represent an important class of commodity chemicals which have broad applicability in different industries. The synthesis of fatty amines starts from renewable sources such as vegetable oils or animal fats, but the process has multiple drawbacks that compromise the overall effectiveness and efficiency of the synthesis. Herein, we report a proof-of-concept biocatalytic alternative towards the synthesis of primary fatty amines from renewable triglycerides and oils. By coupling a lipase with a carboxylic acid reductase (CAR) and a transaminase (TA), we have accomplished the direct synthesis of multiple medium and long chain primary fatty amines in one pot with analytical yields as high as 97 %. We have also performed a 75 mL preparative scale reaction for the synthesis of laurylamine from trilaurin, obtaining 73 % isolated yield.
- Bevinakatti, Han,Citoler, Joan,Finnigan, William,Turner, Nicholas J.
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- A biocatalytic cascade for the conversion of fatty acids to fatty amines
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Fatty amine synthesis from renewable sources is an energetically-demanding process involving toxic metal catalysts and harsh reaction conditions as well as selectivity problems. Herein we present a mild, biocatalytic alternative to the conventional amination of fatty acids through a one-pot tandem cascade performed by a carboxylic acid reductase (CAR) and a transaminase (ω-TA). Saturated and unsaturated fatty acids, with carbon chain lengths ranging from C6 to C18, were successfully aminated obtaining conversions of up to 96%.
- Citoler, Joan,Derrington, Sasha R.,Galman, James L.,Bevinakatti, Han,Turner, Nicholas J.
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supporting information
p. 4932 - 4935
(2019/09/30)
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- Selective Transformations of Triglycerides into Fatty Amines, Amides, and Nitriles by using Heterogeneous Catalysis
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The use of triglycerides as an important class of biomass is an effective strategy to realize a more sustainable society. Herein, three heterogeneous catalytic methods are reported for the selective one-pot transformation of triglycerides into value-added chemicals: i) the reductive amination of triglycerides into fatty amines with aqueous NH3 under H2 promoted by ZrO2-supported Pt clusters; ii) the amidation of triglycerides under gaseous NH3 catalyzed by high-silica H-beta (Hβ) zeolite at 180 °C; iii) the Hβ-promoted synthesis of nitriles from triglycerides and gaseous NH3 at 220 °C. These methods are widely applicable to the transformation of various triglycerides (C4–C18 skeletons) into the corresponding amines, amides, and nitriles.
- Jamil, Md. A. R.,Siddiki, S. M. A. Hakim,Touchy, Abeda Sultana,Rashed, Md. Nurnobi,Poly, Sharmin Sultana,Jing, Yuan,Ting, Kah Wei,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-ichi
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p. 3115 - 3125
(2019/04/26)
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- NOVEL LIPIDS AND LIPID NANOPARTICLE FORMULATIONS FOR DELIVERY OF NUCLEIC ACIDS
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Compounds are provided having the following structure: (I) or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5, R6, R7, R8, R9, L1, L2, a, b, c, d and e are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.
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Page/Page column 74
(2016/05/02)
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- A protic ionic liquid catalyzed strategy for selective hydrolytic cleavage of tert-butyloxycarbonyl amine (N-Boc)
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A simple, mild and efficient strategy for selective hydrolytic cleavage of the N-tert-butyloxycarbonyl (Boc) group is devised using a protic ionic liquid as an efficient catalyst. The deprotection reaction proceeded well for N-Boc protected aromatic, heteroaromatic, aliphatic compounds, and chiral amino acid esters and peptides. A wide range of labile protecting groups such as tert-butyl ester, tert-butyl ether, benzyloxycarbonyl (Cbz), TBDMS, O-Boc and S-Boc remained unaffected under the reaction conditions. This journal is
- Majumdar, Swapan,De, Jhinuk,Chakraborty, Ankita,Roy, Dipanwita,Maiti, Dilip K.
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p. 3200 - 3205
(2015/02/03)
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- Fe5C2 nanoparticles: A facile bromide-induced synthesis and as an active phase for Fischer-Tropsch synthesis
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Iron carbide nanoparticles have long been considered to have great potential in new energy conversion, nanomagnets, and nanomedicines. However, the conventional relatively harsh synthetic conditions of iron carbide hindered its wide applications. In this
- Yang, Ce,Hou, Yanglong,Zhao, Huabo,Ma, Ding
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p. 15814 - 15821,8
(2020/08/24)
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- A novel reduction of azides to amines with tellurium metal in near-critical water
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Tellurium metal in near-critical water (275°C) provides a novel and efficient method for the reduction of azides, producing amines in good yields.
- Wang, Lei,Li, Pinhua,Chen, Jianhui,Yan, Jincan
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p. 1807 - 1813
(2007/10/03)
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- Amino group-containing thiols and method for production thereof
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These amino group-containing mono- or dithiols are represented by formula (I). In order to prepare them, ethylene sulfide is reacted with at least one compound of formula (II), the average number of moles of ethylene sulfide added corresponding to the total m+n, and possibly the compound of formula (I) as obtained is further reacted with ethylene sulfide in order to increase the value of m+n. R1 stands for a straight or branched alkyl or alkenyl group having 10 to 30 carbon atoms; R2 stands for a straight or branched alkyl or alkenyl group having 10 to 30 carbon atoms, or a —(CH2—CH2—S)n—H group; m and n, which are identical or different, each represent 0 or an integer in the range of 1 to 10 and satisfy 1.62 stands for a hydrogen atom in which case R2 in formula (I) will represent —(CH2—CH2—S)n—H, or a straight or branched alkyl or alkenyl group having 10 to 30 carbon atoms, in which case it will remain unchanged in the compound of the formula (I).
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- Catalysts for alkoxylation reactions
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Catalysts producing a sharply peaked alkoxylation distribution during the alkoxylation of organic materials comprise mixtures of BF3 and metal alkyls or metal alkoxides, SiF4 and metal alkyls or metal alkoxides, or mixtures of these catalysts.
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- Methods of alkoxylation
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Catalysts comprising mixtures of HF and metal alkoxides and mixed metal alkoxides produce a sharply peaked alkoxylation distribution during the alkoxylation of organic materials.
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- Kinetics of the Reaction of Alkylamines with 7,7,8,8-Tetracyanoquinodimethane (TCNQ) in Organic Solvents
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The following sequence of substitution reactions was studied spectrophotometrically in organic solvents: where R = butyl, octyl, dodecyl, and hexadecyl.The production of 7-(alkylamino)-7,7,8-tricyanoquinodimethanes proceeds via the formation of the anion radical of TCNQ (TCNQ anion radical) whose rate of appearance was found to be a function of the chain length of R, reaching a maximum for octylamine.The formation of TCNQ anion radical was sensitive to the solvent polarity and electron-donor power and was associated with a small enthalpy and a highly negative entropy of activation.Above a certain the rate of disappearance of TCNQ anion radical was independent of the amine concentration, and the reaction had a much higher enthalpy and entropy of activation.The occurrence of tautomerism precluded an investigation of the conversion of 7-(octylamino)-7,8,8-tricyanoquinodimethane into 7,7-bis(octylamino)-8,8-dicyanoquinodimethane.A study of the reaction of octylamine with 7-morpholino-7,8,8-tricyanoquinodimethane (which does not exist in tautomeric forms) showed that the second substitution step proceeds with the same mechanism as the first one.The only difference between the two compounds (TCNQ and its monosubstituted morpholino derivative) is one of reactivity.
- Seoud, Omar A. El,Ribeiro, Francisco P.,Martins, Abilio,Brotero, Paula P.
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p. 5099 - 5102
(2007/10/02)
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- Catalysts for alkoxylation reactions
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Catalysts and a method of using said catalysts for the alkoxylation of a variety of materials is disclosed. Catalysts so described produce alkoxylates having a very sharp alkoxylate distribution. The catalysts are supported and unsupported dialkoxy and dialkyl metal fluorides and halides and alkyl metal difluorides and dihalides.
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- N-SUBSTITUTED ISONAPHTHALIMIDES. FORMATION AND REACTION WITH AMINES
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N-Substituted isonaphthalimides and N-substituted naphthalimides, as considered previously, are formed in the reaction of 1,8-naphthaloyl chloride with primary amines.The reaction of N-substituted isonaphthalimides with sterically unhindered amines leads to the N,N'-substituted diamides of 1,8-naphthalenedicarboxylic acid.In the case of sterically hindered amines it results in isomerization to the N-substituted naphthalimides.The thermolysis of the N,N'-substituted diamides of 1,8-naphthalenedicarboxylic acid leads to amines and N-substituted naphthalimides.
- Ganin, E. V.,Makarov, V. F.,Nikitin, V. I.
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p. 2209 - 2215
(2007/10/02)
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