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Scalable synthesis of hydrogenated alpha styrene dimer

A technology for hydrogenating α-dimethylstyrene and dimer, which is applied in the directions of hydrocarbon copolymer adhesives, hydrogenation to hydrocarbons, carbon compound catalysts, etc.

Active Publication Date: 2020-08-28
VALVOLINE LICENSING & INTPROP LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Nickel is economical to use, poorly recyclable and has safety concerns when disposed of on a larger scale

Method used

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  • Scalable synthesis of hydrogenated alpha styrene dimer
  • Scalable synthesis of hydrogenated alpha styrene dimer
  • Scalable synthesis of hydrogenated alpha styrene dimer

Examples

Experimental program
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Embodiment 1

[0036] experiment process

[0037] In a one liter Hastelloy reactor with a turbine impeller, the catalyst is added. In some examples, isopropanol was added to the catalyst under nitrogen. To the resulting catalytic solution was added alpha dimethylstyrene dimer. The reaction mixture was stirred with a stirrer at a constant rate of 1,000 RPM. The reaction mixture was heated to the temperature and pressure shown in Table 1. The completion of the reaction was monitored by thin layer chromatography or NMR, and when hydrogen consumption was no longer indicated, the reaction mixture was filtered through a bed of celite under nitrogen. Products were also analyzed by nuclear magnetic resonance (NMR) or gas chromatography mass spectrometry (GCMS).

[0038] The results are shown in Table 1:

[0039]

[0040]

[0041] In some cases, the catalyst is supplied at 50% by weight in water and the % dry basis can be calculated. According to Table 1, at about 10Kg / cm 2 to about 11Kg...

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Abstract

A procedure for hydrogenation of alpha dimethyl styrene dimer that is scalable, economical, and safe is provided. These processes routinely provide greater than a 98% yield and require no purificationstep. The methods of producing hydrogenated alpha dimethyl styrene dimer comprising adding to a reactor under nitrogen a catalyst comprising Ru / C or Rh / C and an alpha dimethyl styrene dimer to form acatalyst and alpha dimethyl styrene dimer reaction mixture. The reaction mixture is then heated under pressure until hydrogenation of the alpha dimethyl styrene dimer is complete. To recover the hydrogenated alpha dimethyl styrene dimer, the reaction mixture is filtered through a celite bed under nitrogen.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to U.S. Provisional Patent Application Serial No. 62 / 597,149, filed December 11, 2017. technical field [0003] The present disclosure generally relates to processes for economically producing hydrogenated alpha dimethylstyrene. Background technique [0004] In 1999, a toroidal continuously variable transmission (T-CVT) car was introduced to the market, and a traction fluid for the T-CVT requires a high level of performance in terms of high traction coefficient of molecules and low-temperature fluidity. Tsubouchi et al. (LubricationScience 2004, 16(4), 393-403) reported parameters for designing molecular structures with high traction coefficients, including high molecular stiffness, large size, short alkylene chain length, high melting point and low molecular polarity for good traction coefficient. The industry uses specially designed traction fluids, such as hydrogenated alpha dimet...

Claims

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Application Information

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IPC IPC(8): C09D109/06C09J125/04C09J125/16C10G47/02
CPCC07C5/10C07C7/12B01D15/10C07C2523/46C07C2601/14G01N30/90G01N30/7206Y02P20/584C07C13/28G01N30/92
Inventor 拉杰库马尔·拉朱尔杰西·达姆巴舍尔
Owner VALVOLINE LICENSING & INTPROP LLC
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