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Catalytic system for farnesene coupling and squalane preparation method

A farnesene coupling and catalytic system technology, applied in chemical instruments and methods, catalytic reactions, hydrogenation hydrocarbon production, etc., can solve the problems of low yield of target products, no industrial value, cumbersome post-treatment, etc., and achieve high reliability The effects of operability, simple separation, and optimization of the reaction system

Pending Publication Date: 2022-01-11
上海泰恒源化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Another problem is that the traditional catalytic system has a selectivity of less than 15% for polyisobutylene with a molecular weight of about 300, resulting in a very low yield of the target product
[0003] At the same time, with isoprene (Japanese patent open 2008-13477), farnesyl acetate (Chem Lett, 1985, 3, 315), farnesol (Tetrahedron Lett, 1990, 31, 4831), farnesyl bromide (Tetrahedron Lett , 1983, 24, 921) and other chemical synthesis methods as raw materials have been developed, but they have no industrial value because of harsh conditions and cumbersome post-treatment.

Method used

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  • Catalytic system for farnesene coupling and squalane preparation method
  • Catalytic system for farnesene coupling and squalane preparation method
  • Catalytic system for farnesene coupling and squalane preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0045] In a 50mL reaction flask, add NiCl 2 (PPh 3 ) 2 (320mg, 0.4893mmol), PPh 3 (256.7mg, 0.9787mmol), HCOONa (665.6mg, 9.7867mmol), replace the gas three times to ensure that the oxygen in the reaction bottle is excluded. N 2 Inject farnesene 6.0mL (24.4667mmol, 1mmolmL -1 ), and inject 18.52mL of isopropanol as a solvent, and replace the gas again to remove oxygen. The reaction was stirred at 70°C for 23h, and the polymerization was stopped. The reaction solution was filtered with celite, the filtrate was collected, and the solvent was drained to obtain a yellow-brown oil, weighing 4.7890 g. The GC-Mass analysis of the yellow-brown oil showed that the selectivity of squalene was 94%, and the yield was 90.0%.

Embodiment 2

[0047] In a 50mL reaction flask, add NiCl 2 (33.03mg, 0.2447mmol), PPh 3 (128.3mg, 0.4893mmol), Na 2 CO 3 (518.6mg, 4.893mmol), replace the gas three times to ensure that the oxygen in the reaction bottle is excluded. N 2 Inject farnesene 6.0mL (24.4667mmol, 1mmolmL -1 ), and inject 18.52mL tetrahydrofuran as a solvent, and replace the gas again to remove oxygen. The reaction was stirred at 85°C for 18h, and the polymerization was stopped. The reaction solution was filtered with diatomaceous earth, the filtrate was collected, and the solvent was drained to obtain a yellow-brown oil, weighing 4.1089 g. The GC-Mass analysis of the yellow-brown oil showed that the selectivity of squalene was 84%, and the yield was 60.8%.

Embodiment 3

[0049] In a 50mL reaction flask, add Pd(OAc) 2 (27.46mg, 0.1223mmol), PPh 3 (64.2mg, 0.2447mmol), Na 2 CO 3 (259.3mg, 2.4467mmol), replace the gas three times to ensure that the oxygen in the reaction bottle is excluded. N 2 Inject farnesene 6.0mL (24.4667mmol, 1mmolmL -1 ), and inject 18.52mL of isopropanol as a solvent, and replace the gas again to remove oxygen. The reaction was stirred at 60°C for 60h, and the polymerization was stopped. The reaction solution was filtered with diatomaceous earth, the filtrate was collected, and the solvent was drained to obtain a yellow-brown oil, weighing 3.9018 g. The GC-Mass analysis of the yellow-brown oil showed that the selectivity of squalene was 91%, and the yield was 71.0%.

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Abstract

The invention relates to a catalytic system for farnesene coupling and squalane preparation method. The methodcomprises the following steps: catalyzing farnesene to perform coupling reaction by adopting the catalytic system for coupling farnesene, so as to prepare squalene, then subjecting the squalene to catalytic hydrogenation reduction reaction to prepare squalane. Compared with the prior art, the method has the advantages that squalene is prepared by catalyzing coupling of farnesene through a catalytic system composed of transition metal, and then the squalane is obtained through hydrogen reduction; the method is simple and easy to synthesize, good in thermal stability and capable of being separated simply.

Description

technical field [0001] The invention relates to the field of chemical raw material preparation, in particular to a catalytic system for farnesene coupling and a squalane preparation method. Background technique [0002] Squalene exists in our sebum membrane, participates in the biosynthesis of cholesterol and various biochemical reactions in the human body, and promotes biological oxidation and metabolism of the body. Synthetic squalene can obtain colorless, odorless and non-toxic squalane product with isomeric linear alkane structure through catalytic hydrogenation. It is a colorless, odorless, stable and high-quality skin care ingredient. Synthetic squalane not only has moisturizing effect, but also repairs skin barrier, anti-aging oxidation, promotes formation and metabolism, antibacterial and antibacterial. Compared with natural squalane, it is cheaper and the synthesis process is simple. The traditional method of preparing squalane is to obtain saturated linear polyiso...

Claims

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Application Information

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IPC IPC(8): B01J27/128B01J31/02B01J31/22B01J31/24B01J31/30C07C2/04C07C11/21C07C5/03C07C9/22
CPCB01J31/2404B01J31/0268B01J31/30B01J27/128B01J31/2239C07C2/04C07C5/03B01J2231/4205B01J2531/824C07C11/21C07C9/22
Inventor 刘龙
Owner 上海泰恒源化学科技有限公司
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