Un article de Wikipédia, l'encyclopédie libre. Unlike vinyl-β-ionol, which is a precursor used for synthesizing vitamin A and β-carotene, it is possible to react vinylpseudoionol as precursor for preparing lycopene under these standard conditions only with poor yields and with low E/Z selectivities to give the corresponding C15 -phosphonium salts. The process according to the invention is carried out in particular at from 20 to 120° C., preferably at 60 to 100° C., in a conventional way. Un sel de phosphonium est un sel contenant l'ion phosphonium (PH4+), comme l'iodure de phosphonium (PH4+I−). The phosphonium structure is converted to phosphine oxide as the result of this reaction. Phosphonium Phosphonium; Systematic name. EP 382 067 describes a process in which C15 -phosphonium salts of lower alkanoic acids are prepared as intermediates because the salts which are mentioned of strong acids always give poor E/Z selectivities and, in the subsequent preparation of lycopene, low yields (byproducts). is Cn H2n+1 --SO3.crclbar. Analysis revealed 50.7 g (90.4%) of 3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl-triphenylphosphonium methanesulfonate consisting of 39.8 g (71.0%) of all-E isomer, 5.69 g (10.1%) of 6Z isomer and 5.22 g (9.3%) of 2Z isomer. As a rule, the C15 -phosphonium salts for synthesizing carotenoids are prepared from vinylcarbinols by reaction with triphenylphosphine and a strong acid such as HCl or H2 SO4 in protic solvents (see, for example, J. Chem. Le composé Ph3PBr2 issu de la réaction entre la triphénylphosphine et le dibrome est appelé bromure de bromotriphénylphosphonium ou dibromotriphénylphosphorane (à présent défini comme « phosphorane ») ou simplement dibromure de triphénylphosphine. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.) InChI=1S/H3P/h1H3/p+1 Key: XYFCBTPGUUZFHI … The E isomer/Z isomers ratio is accordingly 3.4:1. Phosphonium ionic liquids have great promise because previous studies have shown that they have high electrochemical stability. Soc., 1965, 2019-2026). : 124-64-1. © 2004-2020 FreePatentsOnline.com. The salt obtained in this way is immediately suitable for Wittig reaction with 2,7-dimethyl-2,4,6-octatrienedial to prepare lycopene, it being possible to dispense with additional steps such as anion exchange or enrichment of the E component by additional crystallization. Privacy Policy Price. Image. (Phosphonium Salt Prep) Examples: Example 1. The residue was taken up in 25 ml of methanol and extracted once with 100 ml, and four times with 50 ml each time, of heptane. The solution contained 53.5 g (84.0%) of 3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl-triphenylphosphonium p-toluenesulfonate consisting of 41.5 g (65.2%) of all-E isomer, 6.39 g (10.0%) of 6Z isomer and 5.59 g (8.8%) of 2Z isomer. with a triarylphosphine in the presence of a sulfonic acid of the formula Cn H2n+1 --SO3 H or CF3 --SO3 H. where n is as defined above, in a solvent. Une étude[1] a montré qu'en partant d'un dérivé de l'alcool benzylique pour la synthèse d'un acétate de phosphonium, l'arène pouvant porter des groupes activants : Le groupe acétate de phosphonium n'a pas d'impact sur la réaction de Wittig qui suit. Phosphonium Trimethylphosphine Organophosphorus compound … Substance Name: Phosphonium, triphenyl(phenylmethyl)-, salt with 1,1,2,2,3,3,4,4,4-nonafluoro-N-methyl-1-butanesulfonamide (1:1) RN: 332350-93-3 Un sel de phosphonium est un sel contenant l'ion phosphonium (PH 4 +), comme l'iodure de phosphonium (PH 4 + I −). In addition, to obtain a high E/Z ratio in the lycopene, it is necessary to remove (Z) contributions to the phosphonium salt by crystallization. See more » Tetraphenylphosphonium chloride. Product #. 3,7,11-Trimethyl dodeca-2,4,6,10-tetraen-1-yl phosphonium salts. : … Example 1 of EP 372 067 was reproduced several times as stated in the publication. The solution contained 49.2 g (85.6%) of 3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl-triphenylphosphonium ethanesulfonate consisting of 38.8 g (67.5%) of all-E isomer, 5.62 g (9.8%) of 6Z isomer and 4.76 g (8.3%) of 2Z isomer. New!! BASF Aktiengesellschaft (Ludwigshafen, DE). Synonyms. The residue, consisting of 3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl-triphenylphosphonium methanesulfonate, was taken up in 100 ml of toluene, which was then likewise distilled off under 50 mbar, to remove the last residues of acetic acid. Reactive groups are categories of chemicals that typically react in similar ways because they are similar in their chemical structure. Name: Phosphonium, tetrakis(hydroxyethyl)-, sulfate (2:1) (salt) IUPAC Systematic Name: Bis(tetrakis(hydroxymethyl) phosphonium) sulfate (salt) Synonym: Octakis(hydroxyethyl) phosphonium sulfate; 1RPS Tetrakis(hydroxyethyl) phosphonium chloride. Les sels de phosphonium sont en général stables, et peuvent souvent être purifiés par recristallisation dans l'éthanol. The salts of the alkanoic acids must be converted back into the chlorides (anion exchange) in an elaborate procedure before the subsequent Wittig reaction. Les phosphines (R3P) peuvent réagir avec des dihalogènes (X2) pour former des halogénures de phosphonium (R3PX2). The phosphonium salt of the formula I is preferably in the all-E form. In 1995, the US EPA ratified it with zero toxicity and awarded it with US Green Chemical prize due to its properties of high efficacy, low toxicity and low rudimental. Before enrichment of the E isomer, the C15-phosphonium salt was obtained in a yield of 70 to 80% with an E/Z ratio of 2.4-2.6:1. It is an object of the present invention to provide a process for preparing phosphonium salts, which in one step results in 3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-ylphosphonium salts which have a high E content and which give high E/Z selectivities on further reaction to lycopene. Le dibromure et le dichlorure sont disponibles dans le commerce comme réactifs pour halogénation, comme l'halogénation des alcools et des phénols[2]. 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