The present invention relates to a novel solid presentation form of a phenol derivative, characterized by a rounded portion and a flat portion. The compositions thus obtained have advantageous properties suitable for the storage, handling and flow of the compounds. The present invention also relates to a process for preparing these solids, and to the use thereof, in particular in the polymer and agri-food industries.

The present invention relates to a novel solid presentation form of a phenol derivative, characterized by a rounded portion and a flat portion. The compositions thus obtained have advantageous properties suitable for the storage, handling and flow of the compounds. The present invention also relates to a process for preparing these solids, and to the use thereof, in particular in the polymer and agri-food industries.

The present disclosure provides a method for isolating dialkylene phenolic glycol ether (DPGE) from a mixture that includes DPGE and glycosylated phenol impurities. The method includes adding a source of an alkali metal to the mixture to form a phenolic glycol product having an alkali phenolic salt formed from a reaction between the alkali metal and the glycosylated phenol impurities; and separating the DPGE from the alkali phenolic salt in the phenolic glycol product through a thin film evaporation process to produce a dialkylene phenolic glycol ether product. The disclosure also includes a phenolic glycol product that includes DPGE; water; glycosylated phenol impurities; a source of alkali metal; and an alkali phenolic salt formed from a reaction between the alkali metal and the glycosylated phenol impurities.

The present disclosure provides a method for isolating dialkylene phenolic glycol ether (DPGE) from a mixture that includes DPGE and glycosylated phenol impurities. The method includes adding a source of an alkali metal to the mixture to form a phenolic glycol product having an alkali phenolic salt formed from a reaction between the alkali metal and the glycosylated phenol impurities; and separating the DPGE from the alkali phenolic salt in the phenolic glycol product through a thin film evaporation process to produce a dialkylene phenolic glycol ether product. The disclosure also includes a phenolic glycol product that includes DPGE; water; glycosylated phenol impurities; a source of alkali metal; and an alkali phenolic salt formed from a reaction between the alkali metal and the glycosylated phenol impurities.

Disclosed is a method that reforms flare gas or other raw natural gas source, using air without steam, to directly produce dimethyl ether (DME), a direct diesel substitute. The method first reforms an air-natural gas mixture at ambient atmospheric pressures, and then compresses the resulting CO-hydrogen-nitrogen gas mixture to 100-2,000 psi, and feeds it through a combined reactor which reacts the gas mixture directly into DME. The nitrogen is returned to the atmosphere. DME is an excellent diesel fuel, and can be used to displace significantly costlier and dirtier petroleum-based diesel fuel, while solving a critical problem with flaring or other wasted natural gas. For example, the roughly 120 billion cubic feet per year that was flared in North Dakota in 2014 could be converted into over 3 million tons of DME using the disclosed method.

A unique design for a mobile system that reforms flare gas or natural gas, using air without steam, to directly produce dimethyl ether (DME), a diesel substitute, is disclosed. The system first reforms the air-methane mixture at ambient atmospheric pressures, and then compresses the resulting CO-hydrogen-nitrogen gas mixture to up to 600 psi, and feeds it through a combined reactor which reacts the gas mixture directly into dimethyl ether. The nitrogen is returned by the system back to the atmosphere. DME is an excellent diesel fuel, and can be used to displace significantly costlier and dirtier petroleum-based diesel fuel, while solving a critical problem with flaring. For example, the over 120 billion cubic feet per year that is currently flared in North Dakota could be converted into over 3 million tons of DME.

With respect to reduced coenzyme Q10, there has been no report about the presence of crystal polymorphism, and it has been considered that a conventionally obtained crystal form is only one form. The present invention relates to a reduced coenzyme Q10 crystal having an endothermic peak indicating melting at 542 C. during temperature rise at a rate of 5 C./min by differential scanning calorimetry (DSC), and/or to a reduced coenzyme Q10 crystal showing characteristic peaks at diffraction angles (20.2) of 11.5, 18.2, 19.3, 22.3, 23.0 and 33.3 by powder X-ray (CuK) diffraction. The crystal form is a novel reduced coenzyme Q10 crystal which has a higher melting point and a lower solubility in a solvent, and is more excellent in stability than the conventionally known reduced coenzyme Q10 crystal.

With respect to reduced coenzyme Q10, there has been no report about the presence of crystal polymorphism, and it has been considered that a conventionally obtained crystal form is only one form. The present invention relates to a reduced coenzyme Q10 crystal having an endothermic peak indicating melting at 542 C. during temperature rise at a rate of 5 C./min by differential scanning calorimetry (DSC), and/or to a reduced coenzyme Q10 crystal showing characteristic peaks at diffraction angles (20.2) of 11.5, 18.2, 19.3, 22.3, 23.0 and 33.3 by powder X-ray (CuK) diffraction. The crystal form is a novel reduced coenzyme Q10 crystal which has a higher melting point and a lower solubility in a solvent, and is more excellent in stability than the conventionally known reduced coenzyme Q10 crystal.

The present invention provides a stabilization method, a preservation method and the like method of reduced coenzyme Q.sub.10, which is useful as functional nutritive foods, specific health foods and the like. Furthermore, the present invention provides a method for efficiently obtaining reduced coenzyme Q.sub.10 of high quality and by a method suitable for a commercial production. It is possible to handle and stably preserve reduced coenzyme Q.sub.10 under a condition that oxidation by a molecular oxygen is inhibited by contacting reduced coenzyme Q.sub.10 with, an ascorbic acid and citric acid or a related compound thereof, and thus a stabilized composition is obtained. Moreover, reduced coenzyme Q.sub.10 is converted into a crystalline state in such a condition that the formation of oxidized coenzyme Q.sub.10 as a byproduct is minimized by crystallizing reduced coenzyme Q.sub.10 in the presence of ascorbic acid or a related compound thereof etc., and thus a reduced coenzyme Q.sub.10 crystal of high quality is produced. Furthermore, by successively crystallizing the generated reduced coenzyme Q.sub.10 in the presence of ascorbic acid or related compound thereof after reducing oxidized coenzyme Q.sub.10 to reduced coenzyme Q.sub.10 using ascorbic acid or a related compound thereof, operations are simplified and minimized, and thus reduced coenzyme Q.sub.10 of high quality is produced.

The present invention provides a stabilization method, a preservation method and the like method of reduced coenzyme Q.sub.10, which is useful as functional nutritive foods, specific health foods and the like. Furthermore, the present invention provides a method for efficiently obtaining reduced coenzyme Q.sub.10 of high quality and by a method suitable for a commercial production. It is possible to handle and stably preserve reduced coenzyme Q.sub.10 under a condition that oxidation by a molecular oxygen is inhibited by contacting reduced coenzyme Q.sub.10 with, an ascorbic acid and citric acid or a related compound thereof, and thus a stabilized composition is obtained. Moreover, reduced coenzyme Q.sub.10 is converted into a crystalline state in such a condition that the formation of oxidized coenzyme Q.sub.10 as a byproduct is minimized by crystallizing reduced coenzyme Q.sub.10 in the presence of ascorbic acid or a related compound thereof etc., and thus a reduced coenzyme Q.sub.10 crystal of high quality is produced. Furthermore, by successively crystallizing the generated reduced coenzyme Q.sub.10 in the presence of ascorbic acid or related compound thereof after reducing oxidized coenzyme Q.sub.10 to reduced coenzyme Q.sub.10 using ascorbic acid or a related compound thereof, operations are simplified and minimized, and thus reduced coenzyme Q.sub.10 of high quality is produced.