Method for condensing a mixture of oxygen-containing compounds

Abstract

A method for at least partial condensation of an oxygen-containing compound mixture, comprising the following steps: (a) providing a vapor-phase oxygen-containing compound mixture obtained from fragmentation of an aqueous solution of carbohydrates; (b) performing at least partial condensation on the vapor-phase oxygen-containing compound mixture to provide a condensate; and (c) mixing an antifoaming agent with the condensate. The method is provided.

Description

Technical Field

[0001] The present invention relates to a method and an apparatus for at least partially condensing a mixture of oxygen-containing compounds to provide a condensate.

Background Art

[0002] Biomass is particularly important as a feedstock because of its potential to supplement and possibly replace oil as a feedstock for the production of commercial chemicals. In recent years, various technologies for utilizing biomass have been investigated.

[0003] Carbohydrates make up a large proportion of biomass, and various strategies are being established for their effective use as feedstocks for the production of commercial chemicals. These strategies include various fermentation-based methods, catalyst-based methods, pyrolysis, thermolytic fragmentation, and other methods such as hydrocracking, hydroformylation, or acid-catalyzed dehydration.

[0004] The conversion of biomass by the pyrolysis process is desirable because high volumetric production rates can be achieved and because these types of methods can convert a wide range of substrates to a narrow range of products. However, current pyrolysis methods typically have problems when incorporated into an industrial environment. In such an environment, for example, there is a situation where the high efficiency and long-term stability of these methods are desired for industrial applicability.

[0005] One pyrolysis method for converting carbohydrates, particularly saccharides, into commercially important chemicals is "thermolytic fragmentation". Another process step may follow this method. This may also be referred to as "hydrous thermolysis" or "carbohydrate cracking".

[0006] Examples of chemicals produced from biomass include alternative natural gas, biofuels such as ethanol and biodiesel, food browning materials, and commercial chemicals such as diols (ethylene glycol and propylene glycol), acids (lactic acid, acrylic acid, and levulinic acid), and a wide range of other important chemical intermediates (epichlorohydrin, isoprene, furfural, and syngas).

[0007] Accordingly, new uses for C1-C3 oxygenated compound products are being developed, and an increase in demand for these products is expected. Such oxygenated compound products can be used, for example, to produce ethylene glycol and propylene glycol (see, e.g., WO2016 / 001169 (Patent Document 1)) or to capture hydrogen sulfide (see, e.g., WO2017 / 064267 (Patent Document 2)) by subjecting the oxygenated compound product to hydrogenation. However, many other uses are also conceivable.

[0008] Fragmentation of carbohydrates forms a composition consisting mainly of C1-C3 oxygenated compounds. The main C1 oxygenated compound is formaldehyde, which is undesirable in many products due to its high toxicity / carcinogenicity and has also been confirmed to act as a catalyst poison (see, e.g., US2016 / 002137 (Patent Document 3)). The main C2 oxygenated compound is glycolaldehyde, which is a desirable product as it can be converted into useful chemicals such as ethylene glycol, glycolic acid, and methyl vinyl glycolate (methyl 2-hydroxy-3-butanoate). The mixture of oxygenated compounds resulting from carbohydrate fragmentation is useful in many different applications, but the toxicity of formaldehyde can be a problem in some cases. Therefore, the production of compositions that are free of or have greatly reduced levels of formaldehyde is highly desirable. US2016 / 002137 (Patent Document 3) discloses a method for removing formaldehyde by reactive distillation, but this method adds an extra process step.

[0009] WO02 / 40436 (Patent Document 4) discloses a method for producing glycolaldehyde by hydrothermal decomposition. This method involves preparing an aqueous sugar solution; atomizing this aqueous sugar solution; introducing the atomized aqueous sugar solution into a reactor heated between 500 °C and 600 °C to produce a vaporous pyrolysis product; cooling the vaporous pyrolysis product in a condenser to obtain a liquid condensate; collecting the liquid condensate in a storage tank to produce a glycolaldehyde-rich liquid; and filtering this glycolaldehyde-rich liquid.

[0010] It would be desirable to provide an alternative or improved method and / or apparatus for producing a mixture of oxygen-containing compounds obtained from the fragmentation of an aqueous solution of a carbohydrate. It would also be desirable to make the above production suitable for an industrial scale.

Prior Art Documents

Patent Documents

[0011]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Patent Document 5

Patent Document 6

Patent Document 7

Patent Document 8

Summary of the Invention

[0012] In one aspect, a method for at least partial condensation of a mixture of oxygen-containing compounds is provided, the method comprising the following steps: (a) Providing a gaseous oxygen-containing compound mixture obtained from fragmentation of an aqueous solution of a carbohydrate; (b) Performing at least partial condensation on the gaseous oxygen-containing compound mixture to provide a condensate; and (c) Mixing an anti-foaming agent with the condensate; comprising.

[0013] In one aspect, the following steps: (a) Providing a gaseous oxygen-containing compound mixture obtained from fragmentation of an aqueous solution of a carbohydrate; (b) Performing at least partial condensation on the gaseous oxygen-containing compound mixture to provide a condensate; and (c) Mixing an anti-foaming agent with the condensate; A composition prepared by a method comprising is provided.

[0014] In one aspect, the following steps: (a) Providing a gaseous oxygen-containing compound mixture obtained from fragmentation of an aqueous solution of a carbohydrate; (b) Performing at least partial condensation on the gaseous oxygen-containing compound mixture to provide a condensate; and (c) Mixing an anti-foaming agent with the condensate; A condensate prepared by a method comprising is provided.

[0015] In one aspect, an apparatus configured to at least partially condense an oxygen-containing compound mixture is provided, the apparatus comprising: (a) A fragmentation reactor configured to fragment an aqueous solution of a carbohydrate to provide a gaseous oxygen-containing compound mixture; (b) A condenser configured to at least partially condense the gaseous oxygen-containing compound mixture to provide a condensate; and (c) A unit configured to mix an anti-foaming agent with the condensate; comprising.

[0016] Aspects of the present invention will be described by way of example with reference to the accompanying drawings. The accompanying drawings show only examples of aspects of the present invention and should not be regarded as limiting its scope, since other alternative aspects are possible in the present invention.

Brief Description of the Drawings

[0017]

Figure 1

Figure 2

[0018] [Detailed Description of the Invention] Method As described herein, in one aspect, a method for at least partial condensation of an oxygen-containing compound mixture is provided, the method comprising the following steps: (a) providing a gaseous oxygen-containing compound mixture obtained from fragmentation of an aqueous solution of a carbohydrate; (b) performing at least partial condensation on the gaseous oxygen-containing compound mixture to provide a condensate; and (c) mixing an antifoaming agent with the condensate; and comprising.

[0019] The inventors have found that performing at least partial condensation on the gaseous oxygen-containing compound mixture to provide a condensate also forms a significant amount of bubbles along with this condensate. In an industrial-scale process, the bubbles are a problem for condensers and / or units downstream of this condenser, which are typically not configured to handle bubbles.

[0020] The inventors have also found that by mixing an antifoaming agent with the condensate to reduce or suppress the bubbles, a method for producing an oxygen-containing compound mixture obtained from fragmentation of an aqueous solution of a carbohydrate suitable for industrial-scale production can be provided.

[0021] In one aspect, the method is a continuous process, which is usually preferred for industrial scale methods.

[0022] Step (a) - providing a gas-phase oxygen-containing compound mixture obtained from the fragmentation of an aqueous solution of a carbohydrate.

[0023] As described herein, the method requires, as step (a), providing a gas-phase oxygen-containing compound mixture obtained from the fragmentation of an aqueous solution of a carbohydrate.

[0024] The fragmentation of the aqueous solution of the carbohydrate can be achieved by any suitable means. In one aspect, the fragmentation of the aqueous solution of the carbohydrate is pyrolytic fragmentation. In one aspect, the fragmentation of the aqueous solution of the carbohydrate is pyrolysis. The fragmentation of the aqueous solution of the carbohydrate can be carried out by any suitable method. In one aspect, the fragmentation of the aqueous solution of the carbohydrate is carried out as described in WO2020 / 016209 (Patent Document 5) or as described in WO2017 / 216311 (Patent Document 6).

[0025] In the context of the present invention, pyrolytic fragmentation means the selective decomposition of carbohydrates to an oxygenated compound mixture, brought about by heating the carbohydrates to an intermediate temperature (400 - 600 °C) under inert conditions and using a very short residence time. To minimize selectivity to polymerization products or permanent gases, the heating rate used is very fast (> 1000 °C / second), and the residence time is short (< 1 second). One of the important compounds formed from the pyrolytic fragmentation of carbohydrates is glycolaldehyde (hydroxyacetaldehyde). Glycolaldehyde is the smallest known compound containing both a hydroxy group and a carbonyl group, and can also be referred to as a sugar compound. It is highly reactive and is a useful platform chemical for the production of other chemicals such as ethylene glycol and glycolic acid. It is also known to be an unstable molecule at elevated temperatures. See, for example, EP0158517B1 (Patent Document 7), which recommends low-temperature vacuum distillation for purifying glycolaldehyde.

[0026] In the pyrolytic fragmentation of carbohydrates, a composition mainly consisting of C1 - C3 oxygenated compounds (i.e., the vapor-phase oxygenated compound mixture) is formed. In addition to the main product, glycolaldehyde, which is a C2 oxygenated compound, the products obtained by fragmentation (e.g., pyrolysis) of carbohydrates also contain various amounts of C1 - C3 oxygenated compounds such as formaldehyde, glyoxal, pyruvaldehyde, and acetol, as well as small amounts of larger molecules. The presence of formaldehyde, a C1 oxygenated compound, is often undesirable, and in some applications, the removal of formaldehyde is necessary. The presence of larger (and heavier) molecules in the condensate of the pyrolysis products is also undesirable. Typically, a significant amount of resources can be consumed during the fractionation by distillation of a condensed oxygenated compound mixture such as a glucose-based pyrolysis product. This separation can produce an oxygenated compound syrup rich in glycolaldehyde but free of high-boiling by-products.

[0027] In one aspect, a pyrolytic fragmentation step is incorporated into the method. In one aspect, the present invention includes a step of pyrolytic fragmentation of an aqueous solution of a carbohydrate to provide the gas-phase oxygen-containing compound mixture of step (a). In one aspect, step (b) is performed on the gas-phase oxygen-containing compound mixture directly obtained from the pyrolytic fragmentation of the aqueous solution of the carbohydrate.

[0028] In one aspect, the pyrolytic fragmentation of the aqueous solution of the carbohydrate to provide the gas-phase oxygen-containing compound mixture includes adding the aqueous solution of the carbohydrate to a pyrolytic fragmentation reactor.

[0029] In one aspect, the aqueous solution of the carbohydrate is added to the pyrolytic fragmentation reactor at a rate of at least 0.001 kg / h, or at least 0.01 kg / h, or at least 0.1 kg / h, or at least 1 kg / h, or at least 2 kg / h, or at least 5 kg / h, or at least 8 kg / h, or at least 10 kg / h, or at least 12 kg / h, or at least 15 kg / h.

[0030] In one aspect, the aqueous solution of the carbohydrate is added to the pyrolytic fragmentation reactor at a rate of 150 kg / h or less, or 140 kg / h or less, or 130 kg / h or less, or 120 kg / h or less, or 110 kg / h or less, or 100 kg / h or less, or 90 kg / h or less, or 80 kg / h or less, or 70 kg / h or less, or 60 kg / h or less.

[0031] In one aspect, the aqueous solution of the carbohydrate is added to the pyrolytic fragmentation reactor at a rate from 0.001 kg / h to 150 kg / h, or from 0.01 kg / h to 140 kg / h, or from 0.1 kg / h to 130 kg / h, or from 1 kg / h to 120 kg / h, or from 2 kg / h to 110 kg / h, or from 5 kg / h to 100 kg / h, or from 8 kg / h to 90 kg / h, or from 10 kg / h to 80 kg / h, or from 12 kg / h to 70 kg / h, or from 15 kg / h to 60 kg / h.

[0032] In one aspect, the thermal fragmentation of an aqueous solution of carbohydrates to provide a vapor-phase oxygen-containing compound mixture involves adding a flushing gas to the thermal fragmentation reactor. The flushing gas can comprise or consist of a fluidizing gas. Those skilled in the art are familiar with the function of the fluidizing gas and will understand that the fluidizing gas can be used to fluidize the heat medium particles (e.g., sand) in the fragmentation reactor.

[0033] In one aspect, the flushing gas is inert. In one aspect, the flushing gas may contain air or nitrogen or steam. Suitable flushing gases are known to those skilled in the art.

[0034] The carbohydrate of the aqueous solution of carbohydrates can be any suitable carbohydrate. In one aspect, the carbohydrate of the aqueous solution of carbohydrates is selected from monosaccharides, disaccharides, and mixtures thereof. In one aspect, the carbohydrate of the aqueous solution of carbohydrates is at least monosaccharides. In one aspect, the carbohydrate of the aqueous solution of carbohydrates is selected from the group consisting of sucrose, xylose, arabinose, mannose, tagatose, galactose, glucose, fructose, inulin, amylopectin (starch). In one aspect, the carbohydrate of the aqueous solution of carbohydrates is at least glucose. In one aspect, the aqueous solution of carbohydrates is sugar syrup.

[0035] In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 20% by weight of monosaccharides based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 30% by weight of monosaccharides based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 40% by weight of monosaccharides based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 50% by weight of monosaccharides based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 60% by weight of monosaccharides based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 70% by weight of monosaccharides based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 80% by weight of monosaccharides based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 90% by weight of monosaccharides based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 95% by weight of monosaccharides based on the total amount of the carbohydrate.

[0036] In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 20% by weight of glucose based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 30% by weight of glucose based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 40% by weight of glucose based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 50% by weight of glucose based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 60% by weight of glucose based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 70% by weight of glucose based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 80% by weight of glucose based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 90% by weight of glucose based on the total amount of the carbohydrate. In one aspect, the carbohydrate in the aqueous solution of carbohydrate contains at least 95% by weight of glucose based on the total amount of the carbohydrate.

[0037] The aqueous solution of carbohydrate may contain carbohydrate in any suitable amount. From one perspective, the aqueous solution of carbohydrate contains carbohydrate in an amount of at least 10% by weight based on this aqueous solution. From one perspective, the aqueous solution of carbohydrate contains carbohydrate in an amount of at least 20% by weight based on this aqueous solution. From one perspective, the aqueous solution of carbohydrate contains carbohydrate in an amount of at least 30% by weight based on this aqueous solution. From one perspective, the aqueous solution of carbohydrate contains carbohydrate in an amount of at least 40% by weight based on this aqueous solution. From one perspective, the aqueous solution of carbohydrate contains carbohydrate in an amount of at least 50% by weight based on this aqueous solution. From one perspective, the aqueous solution of carbohydrate contains carbohydrate in an amount of at least 60% by weight based on this aqueous solution. From one perspective, the aqueous solution of carbohydrate contains glucose in an amount of at least 10% by weight based on this aqueous solution. From one perspective, the aqueous solution of carbohydrate contains glucose in an amount of at least 20% by weight based on this aqueous solution. From one perspective, the aqueous solution of carbohydrate contains glucose in an amount of at least 30% by weight based on this aqueous solution. From one perspective, the aqueous solution of carbohydrate contains glucose in an amount of at least 40% by weight based on this aqueous solution. From one perspective, the aqueous solution of carbohydrate contains glucose in an amount of at least 50% by weight based on this aqueous solution. From one perspective, the aqueous solution of carbohydrate contains glucose in an amount of at least 60% by weight based on this aqueous solution.

[0038] For the aqueous solution of carbohydrate, the upper limit of carbohydrate is defined by the solubility of each carbohydrate. For both carbohydrates, namely disaccharides and monosaccharides, and for any of the saccharides (especially glucose), an upper limit of 95% by weight, for example 96, 97, 98, 99% by weight, can be assumed based on the aqueous solution.

[0039] The inventors have found that at least partial condensation of the vapor-phase oxygenated compound mixture derived from biomass has a particularly strong tendency to form a significant amount of bubbles. From one perspective, the vapor-phase oxygenated compound mixture is derived from biomass. From one perspective, the aqueous solution of carbohydrates is derived from biomass. From one perspective, the carbohydrates in the aqueous solution of carbohydrates are derived from biomass. From one perspective, the biomass is selected from plant biomass, animal biomass, or a combination thereof. Non-limiting examples of biomass include wood, wood residues, forest residues, agricultural residues (e.g., straw, hay, corn, wheat, sugarcane bagasse, and green agricultural waste), agro-industrial waste (e.g., sugarcane bagasse, beets, and rice husks), animal waste (e.g., cattle waste for fertilizer and livestock scraps), industrial waste (e.g., black liquor from paper making), sewage sludge, municipal waste, and food processing waste, etc.

[0040] As will be understood by those skilled in the art, the vapor-phase oxygenated compound mixture can vary depending on the properties of the aqueous solution of carbohydrates (carbohydrate feedstock) and the fragmentation conditions, and has a mass ratio of each component (e.g., the mass ratio of glycolaldehyde to formaldehyde).

[0041] From one perspective, the vapor-phase oxygenated compound mixture contains C1-C3 oxygenated compounds. From one perspective, the vapor-phase oxygenated compound mixture contains at least 40% by weight of C1-C3 oxygenated compounds based on the total weight of the vapor-phase oxygenated compound mixture. From one perspective, the vapor-phase oxygenated compound mixture contains at least 50% by weight of C1-C3 oxygenated compounds based on the total weight of the vapor-phase oxygenated compound mixture. From one perspective, the vapor-phase oxygenated compound mixture contains at least 60% by weight of C1-C3 oxygenated compounds based on the total weight of the vapor-phase oxygenated compound mixture. From one perspective, the vapor-phase oxygenated compound mixture contains at least 70% by weight of C1-C3 oxygenated compounds based on the total weight of the vapor-phase oxygenated compound mixture.

[0042] There is no upper limit at which the present invention ceases to function. However, an upper limit of 90% by weight of C1-C3 oxygen-containing compounds, based on the total weight of the vapor-phase oxygen-containing compound mixture, is possible for any of the lower limits described above.

[0043] In one aspect, the vapor-phase oxygen-containing compound mixture consists essentially of C1-C3 oxygen-containing compounds. In one aspect, the vapor-phase oxygen-containing compound mixture consists substantially of C1-C3 oxygen-containing compounds.

[0044] Step (b) - subjecting the vapor-phase oxygen-containing compound mixture to at least partial condensation to provide a condensate: As described herein, the method according to the present invention requires step (b) of subjecting the vapor-phase oxygen-containing compound mixture to at least partial condensation to provide a condensate.

[0045] The method includes partial condensation of the vapor-phase oxygen-containing compound mixture. "Partial condensation" means that a part of the vapor-phase oxygen-containing compound mixture is condensed in the condensation step to provide a condensate. When the condensation is partial condensation, the resulting condensate may also be referred to as a "partially condensed condensate". The method includes completely condensing the vapor-phase oxygen-containing compound mixture to provide a condensate. "Complete condensation" means that substantially all of the vapor-phase oxygen-containing compound mixture is condensed in the condensation step to provide a condensate. When the condensation is complete condensation, the resulting condensate may also be referred to as a "completely condensed condensate". As will be understood by those skilled in the art, partial condensation and complete condensation can result in condensates of different compositions.

[0046] In one aspect, a method for complete condensation of an oxygen-containing compound mixture is provided, the method comprising the following steps: (a) providing a vapor-phase oxygen-containing compound mixture obtained from fragmentation of an aqueous solution of a carbohydrate; (b) subjecting the vapor-phase oxygen-containing compound mixture to complete condensation to provide a completely condensed condensate; and (c) mixing an antifoaming agent with the condensate. includes

[0047] As those skilled in the art will understand, the gas-phase oxygen-containing compound mixture may have a ratio of glycolaldehyde to formaldehyde that varies depending on the properties of the aqueous solution of the carbohydrate (carbohydrate feed) and the fragmentation conditions.

[0048] In one aspect, the gas-phase oxygen-containing compound mixture has a mass ratio of glycolaldehyde to formaldehyde from 2:1 to 18:1. In one aspect, the gas-phase oxygen-containing compound mixture has a mass ratio of glycolaldehyde to formaldehyde from 3:1 to 18:1. In one aspect, the gas-phase oxygen-containing compound mixture has a mass ratio of glycolaldehyde to formaldehyde from 4:1 to 18:1. In one aspect, the gas-phase oxygen-containing compound mixture has a mass ratio of glycolaldehyde to formaldehyde from 5:1 to 18:1. In one aspect, the gas-phase oxygen-containing compound mixture has a mass ratio of glycolaldehyde to formaldehyde from 2:1 to 15:1. In one aspect, the gas-phase oxygen-containing compound mixture has a mass ratio of glycolaldehyde to formaldehyde from 3:1 to 15:1. In one aspect, the gas-phase oxygen-containing compound mixture has a mass ratio of glycolaldehyde to formaldehyde from 4:1 to 15:1. In one aspect, the gas-phase oxygen-containing compound mixture has a mass ratio of glycolaldehyde to formaldehyde from 5:1 to 15:1. In one aspect, the gas-phase oxygen-containing compound mixture has a mass ratio of glycolaldehyde to formaldehyde from 2:1 to 10:1. In one aspect, the gas-phase oxygen-containing compound mixture has a mass ratio of glycolaldehyde to formaldehyde from 3:1 to 10:1. In one aspect, the gas-phase oxygen-containing compound mixture has a mass ratio of glycolaldehyde to formaldehyde from 4:1 to 10:1. In one aspect, the gas-phase oxygen-containing compound mixture has a mass ratio of glycolaldehyde to formaldehyde from 5:1 to 10:1.

[0049] As those skilled in the art will understand, the composition of the condensate can vary depending on whether partial or complete condensation has occurred or not. For example, if partial condensation occurs in step (b), the mass ratio of each component in the gas-phase oxygen-containing compound mixture (e.g., the ratio of glycolaldehyde to formaldehyde) may be different from the mass ratio of each component in the condensate. In contrast, if complete condensation occurs in step (b), the mass ratio of each component in the gas-phase oxygen-containing compound mixture (e.g., the ratio of glycolaldehyde to formaldehyde) may be substantially the same as the mass ratio of each component in the condensate.

[0050] From one perspective, the condensate has a mass ratio of glycolaldehyde to formaldehyde of at least 5:1. From one perspective, the condensate has a mass ratio of glycolaldehyde to formaldehyde of at least 10:1. From one perspective, the condensate has a mass ratio of glycolaldehyde to formaldehyde of at least 15:1. From one perspective, the condensate has a mass ratio of glycolaldehyde to formaldehyde of at least 20:1. From one perspective, the condensate has a mass ratio of glycolaldehyde to formaldehyde of at least 30:1. From one perspective, the condensate has a mass ratio of glycolaldehyde to formaldehyde of at least 40:1. From one perspective, the condensate has a mass ratio of glycolaldehyde to formaldehyde of at least 50:1. From one perspective, the condensate has a mass ratio of glycolaldehyde to formaldehyde of at least 60:1. From one perspective, the condensate has a mass ratio of glycolaldehyde to formaldehyde of at least 70:1. From one perspective, the condensate has a mass ratio of glycolaldehyde to formaldehyde of at least 80:1. From one perspective, the condensate has a mass ratio of glycolaldehyde to formaldehyde of at least 90:1. From one perspective, the condensate has a mass ratio of glycolaldehyde to formaldehyde of at least 100:1.

[0051] In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde of 500:1 or less. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde of 400:1 or less. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde of 300:1 or less. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde of 200:1 or less. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde of 180:1 or less. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde of 160:1 or less. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde of 150:1 or less. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde of 140:1 or less. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde of 130:1 or less. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde of 120:1 or less. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde of 110:1 or less. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde of 100:1 or less.

[0052] In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 10:1 to 200:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 10:1 to 180:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 10:1 to 160:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 10:1 to 150:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 10:1 to 140:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 10:1 to 130:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 10:1 to 120:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 10:1 to 110:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 10:1 to 100:1.

[0053] In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 30:1 to 200:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 30:1 to 180:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 30:1 to 160:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 30:1 to 150:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 30:1 to 140:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 30:1 to 130:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 30:1 to 120:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 30:1 to 130:1. In one aspect, the condensate has a mass ratio of glycolaldehyde to formaldehyde from 30:1 to 100:1.

[0054] The process parameters necessary to effect at least partial condensation of the present invention can be readily determined by one of ordinary skill in the art. The important parameters are the composition of the vapor phase oxygenate mixture, the temperature of at least partial condensation, and the pressure of at least partial condensation. Generally, the composition of the vapor phase oxygenate mixture is defined by the fragmentation process. Similarly, the pressure of at least partial condensation can typically be defined by the requirements of the upstream process. Therefore, the temperature of at least partial condensation is the parameter that is typically controlled to achieve the required separation. If the pressure is not defined by matters to be considered in the upstream process and can be freely controlled, in principle, this can be used as an alternative control parameter (with the temperature fixed). However, for most practical applications, control of the temperature of at least partial condensation is more suitable. In any case, the matters to be considered for the use of pressure as a control parameter are the same as those described below for temperature.

[0055] In one aspect, the condensate is condensed at a temperature from 0 to 150 °C. In one aspect, the condensate is condensed at a temperature from 10 to 150 °C. In one aspect, the condensate is condensed at a temperature from 20 to 150 °C. In one aspect, the condensate is condensed at a temperature from 30 to 150 °C. In one aspect, the condensate is condensed at a temperature from 30 to 130 °C. In one aspect, the condensate is condensed at a temperature from 0 to 90 °C. In one aspect, the condensate is condensed at a temperature from 5 to 90 °C. In one aspect, the condensate is condensed at a temperature from 30 to 90 °C. In one aspect, the condensate is condensed at a temperature from 40 to 90 °C. In one aspect, the condensate is condensed at a temperature from 30 to 70 °C. In one aspect, the condensate is condensed at a temperature from 40 to 60 °C.

[0056] In one aspect, a method for at least partial condensation of an oxygen-containing compound mixture is provided, the method comprising the steps of: (a) providing a gaseous oxygen-containing compound mixture obtained from fragmentation of an aqueous solution of carbohydrates; and (b) performing at least partial condensation on the gaseous oxygen-containing compound mixture to provide a condensate, wherein the condensate is condensed at a temperature from 0 to 150 °C; and (c) mixing an antifoaming agent with the condensate; comprising.

[0057] From one perspective, the condensate emerging from the condenser has a temperature ranging from 0 to 150 °C. From one perspective, the condensate emerging from the condenser has a temperature ranging from 10 to 150 °C. From one perspective, the condensate emerging from the condenser has a temperature ranging from 20 to 150 °C. From one perspective, the condensate emerging from the condenser has a temperature ranging from 30 to 150 °C. From one perspective, the condensate emerging from the condenser has a temperature ranging from 0 to 90 °C. From one perspective, the condensate emerging from the condenser has a temperature ranging from 5 to 90 °C. From one perspective, the condensate emerging from the condenser has a temperature ranging from 40 to 90 °C. From one perspective, the condensate emerging from the condenser has a temperature ranging from 30 to 70 °C. From one perspective, the condensate emerging from the condenser has a temperature ranging from 40 to 60 °C.

[0058] From one perspective, a method for at least partial condensation of an oxygen-containing compound is provided, the method comprising the following steps: (a) providing a gaseous oxygen-containing compound mixture obtained from the fragmentation of an aqueous solution of a carbohydrate; and (b) performing at least partial condensation on the gaseous oxygen-containing compound mixture to provide a condensate, wherein the condensate produced by this at least partial condensation has a temperature ranging from 0 to 150 °C; and (c) mixing an antifoaming agent with the condensate; comprising.

[0059] As described herein, an intermediate step may be performed on the oxygen-containing compound mixture prior to step (b). For example, an initial partial condensation may be performed on the oxygen-containing compound mixture prior to the partial condensation step (b). From one perspective, step (b) is performed on an oxygen-containing compound mixture directly obtained from the fragmentation of an aqueous solution of a carbohydrate. This intermediate step may be selected, for example, depending on the composition of the oxygen-containing compound mixture directly obtained from the fragmentation of an aqueous solution of a carbohydrate. As will be understood by those skilled in the art, the composition of the oxygen-containing compound mixture directly obtained from the fragmentation of an aqueous solution of a carbohydrate depends, inter alia, on the composition of the aqueous solution of the carbohydrate and the fragmentation process parameters.

[0060] In one aspect, the implementation of at least partial condensation of the vapor-phase oxygen-containing compound mixture involves passing (or introducing into a condenser) an input stream containing the vapor-phase oxygen-containing compound mixture through a condenser to provide a condensate and an output stream. When using partial condensation, the output stream may contain a partially condensed vapor phase. In one aspect, the input stream contains a flushing gas. The condensate and the output stream exit the condenser, for example, at or near the top of the condenser.

[0061] Downstream of the condenser, one or more environmentally problematic components (e.g., components from the output stream) can be removed from the gas phase using a catalyst. The inventors have found that bubbles can weaken or destroy the catalyst. By using an antifoaming agent, the catalyst can be protected from the bubbles such that its performance is maintained.

[0062] In one aspect, the output stream exiting the condenser has a temperature from 0 to 50 °C. In one aspect, the output stream exiting the condenser has a temperature from 0 to 40 °C. In one aspect, the output stream exiting the condenser has a temperature from 0 to 30 °C. In one aspect, the output stream exiting the condenser has a temperature from 0 to 20 °C. In one aspect, the output stream exiting the condenser has a temperature from 10 to 20 °C.

[0063] In one aspect, the implementation of at least partial condensation of the vapor-phase oxygen-containing compound mixture involves supplying an input stream containing the vapor-phase oxygen-containing compound mixture and a flushing gas into a condenser to provide a condensate and an output stream, where the output stream contains the flushing gas.

[0064] In one aspect, the implementation of at least partial condensation of the vapor-phase oxygen-containing compound mixture involves recycling at least a portion of the output stream containing the flushing gas into the input stream. The inventors have found that recycling of the output stream in an industrial-scale process can result in the generation of a significant amount of bubbles. However, with the use of an anti-foaming agent, the present invention enables such recycling in an industrial-scale process while reducing the generated bubbles to a reduced level (e.g., an acceptable or minimum amount of bubbles).

[0065] In one aspect, the implementation of at least partial condensation of the vapor-phase oxygen-containing compound mixture involves dividing the condensate into at least a condensate product stream and a condensate recycle stream.

[0066] In one aspect, the mass ratio of the condensate recycle stream to the condensate product stream is from 5:1 to 50:1. In one aspect, the mass ratio of the condensate recycle stream to the condensate product stream is from 10:1 to 30:1. In one aspect, the mass ratio of the condensate recycle stream to the condensate product stream is from 10:1 to 20:1.

[0067] In one aspect, the implementation of at least partial condensation of the vapor-phase oxygen-containing compound mixture involves adding the condensate recycle stream to a condenser.

[0068] In one aspect, the condensate is cooled. In one aspect, the condensate recycle stream is cooled before adding the condensate recycle stream to the condenser. The inventors have found that adding the condensate (e.g., the condensate recycle stream) to the condenser promotes the condensation of the vapor-phase oxygen-containing compound mixture.

[0069] In one aspect, the condensate recycle stream added to the condenser has a temperature from 0 to 50 °C. In one aspect, the condensate recycle stream added to the condenser has a temperature from 0 to 40 °C. In one aspect, the condensate recycle stream added to the condenser has a temperature from 0 to 30 °C. In one aspect, the condensate recycle stream added to the condenser has a temperature from 0 to 20 °C. In one aspect, the condensate recycle stream added to the condenser has a temperature from 10 to 20 °C. In this regard, the temperature at which the condensate recycle stream is added to the condenser may mean the temperature of the condensate recycle stream entering the condenser.

[0070] In one aspect, the condensate recycle stream is added to the condenser at or near the top of the condenser. By doing so, the condensate will flow through the condenser under gravity. In one aspect, the condensate recycle stream is added at or near the bottom of the condenser.

[0071] In one aspect, the condenser includes a packing material. The packing material increases the contact area between the recycled condensate, the defoaming agent (if applicable), and the vapor-phase oxygen-containing compound mixture (e.g., the input stream) within the condenser. Those skilled in the art will know suitable packing materials.

[0072] In one aspect, the vapor-phase oxygen-containing compound mixture (or input stream) is filtered before at least partial condensation of the vapor-phase oxygen-containing compound mixture is carried out.

[0073] Step (c) - Step of mixing the defoaming agent and the condensate: As described herein, the method requires step (c) of mixing the defoaming agent and the condensate.

[0074] In the context of the present invention, the defoaming agent is understood to be one that eliminates existing bubbles, or prevents the formation of bubbles, or both eliminates existing bubbles and prevents the formation of bubbles. Therefore, in the context of the present invention, the defoaming agent is understood to be one that can do one or both of eliminating existing bubbles and preventing the formation of bubbles.

[0075] In one aspect, combining the defoaming agent and the condensate includes adding the defoaming agent to the condensate. In one aspect, combining the defoaming agent and the condensate includes continuously or intermittently adding the defoaming agent to the condensate.

[0076] In one aspect, combining the defoaming agent and the condensate includes adding the condensate to the defoaming agent. For example, the defoaming agent can be contained in a container to which the condensate is added.

[0077] In one aspect, combining the defoaming agent and the condensate includes combining the defoaming agent and the condensate in a condenser. In one aspect, combining the defoaming agent and the condensate includes adding the defoaming agent to the condenser.

[0078] In one aspect, combining the defoaming agent and the condensate includes adding a condensate recycle stream to the condensate.

[0079] In one aspect, combining the defoaming agent and the condensate includes adding the defoaming agent to the condensate recycle stream to form a mixture and adding this mixture to the condenser.

[0080] In one aspect, the mixture is divided into a plurality of streams. In one aspect, each of these plurality of streams is added to each part of the condenser. In one aspect, at least a portion of the mixture (e.g., by one stream) is added to the condenser at or near the top of the condenser. In one aspect, at least a portion of the mixture (e.g., by one stream) is added into the condenser onto the packing. In one aspect, at least a portion of the mixture (e.g., by one stream) is added to the condenser at or near the bottom of the condenser. In one aspect, at least a portion of the mixture (e.g., by one stream) is added into the condenser under the packing. When referring to "top", "bottom", "above", "below", it is with respect to gravity.

[0081] In one aspect, at least a portion of the mixture applied to the condenser flows countercurrently to the flow of the gas-phase oxygen-containing compound mixture within the condenser.

[0082] In one aspect, the mixture applied to the condenser has a temperature from 0 to 50 °C. In one aspect, the mixture applied to the condenser has a temperature from 0 to 40 °C. In one aspect, the mixture applied to the condenser has a temperature from 0 to 30 °C. In one aspect, the mixture applied to the condenser has a temperature from 0 to 20 °C. In one aspect, the mixture applied to the condenser has a temperature from 10 to 20 °C. In this regard, the temperature at which the mixture is applied to the condenser may mean the temperature of the mixture entering the condenser.

[0083] Antifoaming agent In one aspect, the antifoaming agent is added to the condensate at a rate of at least 0.0000001 mL / h, or at least 0.000001 mL / h, or at least 0.00001 mL / h, or at least 0.0001 mL / h, or at least 0.001 mL / h, or at least 0.01 mL / h, or at least 0.1 mL / h, or at least 1 mL / h, or at least 1.2 mL / h, or at least 1.5 mL / h.

[0084] In one aspect, the antifoaming agent is added to the agglomerate at a rate of 200 mL / h or less, or 100 mL / h or less, or 50 mL / h or less, or 20 mL / h or less, or 10 mL / h or less, or 8 mL / h or less, or 6 mL / h or less, or 5 mL / h or less, or 4 mL / h or less, or 3.8 mL / h or less.

[0085] In one aspect, the defoaming agent is added to the aggregates at a rate from 0.0000001 mL / h to 200 mL / h, or from 0.000001 mL / h to 100 mL / h, or from 0.00001 mL / h to 50 mL / h, or from 0.0001 mL / h to 20 mL / h, or from 0.001 mL / h to 10 mL / h, or from 0.01 mL / h to 8 mL / h, or from 0.1 mL / h to 6 mL / h, or from 1 mL / h to 5 mL / h, or from 1.2 mL / h to 4 mL / h, or from 1.5 mL / h to 3.8 mL / h.

[0086] In one aspect, in the mixed defoaming agent and condensate, the mass ratio of the defoaming agent to the condensate is at least 1:1000000, or at least 1:800000, or at least 1:500000, or at least 1:200000, or at least 1:100000, or at least 1:80000, or at least 1:50000, or at least 1:25000, or at least 1:20000, or at least 1:18000.

[0087] In one aspect, in the mixed defoaming agent and condensate, the mass ratio of the defoaming agent to the condensate is 1:1 or less, or 1:2 or less, or 1:4 or less, or 1:6 or less, or 1:8 or less, or 1:10 or less, or 1:12 or less, or 1:14 or less, or 1:16 or less, or 1:18 or less.

[0088] In one aspect, in the mixed defoaming agent and condensate, the mass ratio of the defoaming agent to the condensate is from 1:1000000 to 1:1, or from 1:800000 to 1:2, or from 1:500000 to 1:4, or from 1:200000 to 1:6, or from 1:100000 to 1:8, or from 1:80000 to 1:10, or from 1:50000 to 1:12, or from 1:25000 to 1:14, or from 1:20000 to 1:16, or from 1:18000 to 1:18.

[0089] In one aspect, the antifoaming agent has a surface tension of 70 mN / m or less, or 60 mN / m or less, or 50 mN / m or less, or 40 mN / m or less, or 35 mN / m or less, or 30 mN / m or less, or 25 mN / m or less, or 20 mN / m or less, or 15 mN / m or less, or 10 mN / m or less, or 5 mN / m or less at 20°C.

[0090] In one aspect, the antifoaming agent has a surface tension between 20 mN / m and 30 mN / m at 20°C.

[0091] The surface tension can be measured by any suitable method, such as using a surface tensiometer. In one aspect, the surface tension is measured using a Wilhelmy plate tensiometer, a Du Noüy ring tensiometer, or a bubble pressure tensiometer.

[0092] In one aspect, the antifoaming agent contains one or more active ingredients. As will be understood by those skilled in the art, the "active ingredient(s)" of the antifoaming agent is the part of the antifoaming agent that causes its defoaming effect.

[0093] In one aspect, the antifoaming agent consists essentially of, consists of, or substantially contains the above-mentioned one kind of active ingredient.

[0094] In one aspect, the total active ingredient content of the antifoaming agent is at least 0.0000001% by weight, or at least 0.000001% by weight, or at least 0.00001% by weight, or at least 0.0001% by weight, or at least 0.001% by weight, or at least 0.01% by weight, or at least 0.1% by weight, or at least 0.2% by weight, or at least 0.3% by weight, or at least 0.4% by weight based on the total weight of the antifoaming agent.

[0095] In one aspect, the defoaming agent has a total active ingredient content of up to 100% by weight. In one aspect, the defoaming agent has a total active ingredient content of 95% by weight or less, or 90% by weight or less, or 80% by weight or less, or 70% by weight or less, or 60% by weight or less, or 50% by weight or less, or 40% by weight or less, or 30% by weight or less, or 25% by weight or less, or 20% by weight or less, based on the total weight of the defoaming agent.

[0096] In one aspect, the defoaming agent has a total active ingredient content of from 0.0000001% by weight to 100% by weight, or from 0.0000001% by weight to 95% by weight, or from 0.000001% by weight to 90% by weight, or from 0.00001% by weight to 80% by weight, or from 0.0001% by weight to 70% by weight, or from 0.001% by weight to 60% by weight, or from 0.01% by weight to 50% by weight, or from 0.1% by weight to 40% by weight, or from 0.2% by weight to 30% by weight, or from 0.3% by weight to 25% by weight, or from 0.4% by weight to 20% by weight, based on the total weight of the defoaming agent.

[0097] In one aspect, the one or more active ingredients are each independently selected from alcohols, ethers, carboxylic acids, esters, silicones (e.g., organosilicones), silicas, oils (e.g., vegetable oils or mineral oils), waxes, and acrylates. In one aspect, the one or more active ingredients are each independently selected from alcohols and silicones.

[0098] In one aspect, when the one or more active ingredients are each selected from alcohols, the defoaming agent may substantially contain, consist essentially of, or consist of one or more active ingredients.

[0099] In one aspect, when the one or more active ingredients are selected from silicones, the defoamer may contain at least 0.0000001 wt%, or at least 0.000001 wt%, or at least 0.00001 wt%, or at least 0.0001 wt%, or at least 0.001 wt%, or at least 0.01 wt%, or at least 0.1 wt%, or at least 1 wt%, or at least 5 wt% of silicones (multiple possible) based on the total weight of the defoamer.

[0100] In one aspect, when the one or more active ingredients are each selected from silicones, the defoamer may contain 100 wt% or less, or 95 wt% or less, or 90 wt% or less, or 80 wt% or less, or 70 wt% or less, or 60 wt% or less, or 50 wt% or less, or 40 wt% or less, or 30 wt% or less, or 20 wt% or less of silicones (multiple possible) based on the total weight of the defoamer.

[0101] In one aspect, when the one or more active ingredients are each selected from silicones, the defoamer may contain from 0.0000001 wt% to 100 wt%, or from 0.0000001 wt% to 95 wt%, or from 0.000001 wt% to 90 wt%, or from 0.00001 wt% to 80 wt%, or from 0.0001 wt% to 70 wt%, or from 0.001 wt% to 60 wt%, or from 0.01 wt% to 50 wt%, or from 0.1 wt% to 40 wt%, or from 1 wt% to 30 wt%, or from 5 wt% to 20 wt% of silicones (multiple possible) based on the total weight of the defoamer.

[0102] In one aspect, the defoamer contains an aqueous solution. In one aspect, the defoamer contains an aqueous solution of one or more active ingredients.

[0103] In one aspect, the defoamer contains an emulsion. In one aspect, the defoamer contains a silicone-containing emulsion.

[0104] In one aspect, the alcohol is selected from primary alcohols. In one aspect, the alcohol is selected from secondary alcohols. In one aspect, the alcohol is selected from tertiary alcohols.

[0105] In one aspect, the alcohol is selected from C1-C12 alcohols. In one aspect, the alcohol is selected from C1-C10 alcohols. In one aspect, the alcohol is selected from C1-C8 alcohols. In one aspect, the alcohol is selected from C1-C6 alcohols. In one aspect, the alcohol is selected from C1-C4 alcohols. In one aspect, the alcohol is selected from propanol. In one aspect, the alcohol is selected from 1-propanol and 2-propanol. In one aspect, the alcohol is 2-propanol.

[0106] In one aspect, the alcohol is selected from polyalkylene glycols. In one aspect, the alcohol is polyethylene glycol.

[0107] In one aspect, the silicone is selected from polydimethylsiloxane.

[0108] Other process steps The method of the present invention may include one or more further distinct steps. These one or more further distinct steps can be before, after or intermediate to the steps described herein.

[0109] In one aspect, the method includes a further step of recovering a condensate (e.g., at least a portion thereof, e.g., the condensate product stream). In one aspect, the condensate is recovered by distillation. In one aspect, the condensate is recovered by solvent extraction.

[0110] Composition In one aspect, there is provided a composition prepared by the method described herein. The composition includes a condensate and an antifoaming agent.

[0111] Condensate In one aspect, condensates prepared by the methods described herein are provided.

[0112] Apparatus As described herein, in one aspect, an apparatus configured to at least partially condense an oxygen-containing compound mixture is provided, the apparatus comprising: (a) a fragmentation reactor configured to fragment an aqueous solution of carbohydrate to provide a vapor-phase oxygen-containing compound mixture; (b) a condenser configured to at least partially condense the vapor-phase oxygen-containing compound mixture to provide a condensate; and (c) a unit configured to mix an anti-foaming agent with the condensate. Including.

[0113] In one aspect, the apparatus is configured to at least partially condense an oxygen-containing compound mixture by performing the methods described herein.

[0114] Suitable types of fragmentation reactors are known to those skilled in the art. In one aspect, the fragmentation reactor is a pyrolysis fragmentation reactor. In one aspect, the fragmentation reactor is a pyrolysis fragmentation reactor. In one aspect, the fragmentation reactor is a fluidized bed reactor. In one aspect, the fluidized bed reactor is selected from a bubbling bed reactor, a turbulent bed reactor, and a riser type reactor.

[0115] In one aspect, the fragmentation reactor includes one or more of a feed inlet, a product outlet, a riser, and a fluidizing gas inlet.

[0116] Suitable condensers are known to those skilled in the art. In one aspect, the condenser is selected from a water-cooled condenser, an air-cooled condenser, and an evaporative condenser. In one aspect, the condenser is a cooling tower.

[0117] In one aspect, the apparatus includes a separator configured to separate particulate matter from a vapor-phase oxygen-containing compound mixture. The separator may be a filter. The particulate matter may be dust, for example, dust from a fragmentation reactor. The particulate matter may include heat transfer medium particles or fragments thereof from a fragmentation reactor in terms of the use of heat transfer medium particles.

[0118] As described herein, the present invention includes partially condensing a vapor-phase oxygen-containing compound mixture to provide a condensate and / or completely condensing a vapor-phase oxygen-containing compound mixture to provide a condensate. In one aspect, the apparatus may include a single condenser. When the apparatus includes a single condenser, the condenser may be used for complete condensation of the vapor-phase oxygen-containing compound mixture in step (b). In one aspect, the apparatus may include a plurality of condensers. When the apparatus includes a plurality of condensers, these condensers may be used for multiple partial condensations of the vapor-phase oxygen-containing compound mixture in step (b).

[0119] Any suitable unit configured to mix the defoaming agent and the condensate may be used.

[0120] In one aspect, the unit includes a dispenser configured to dispense the defoaming agent. In one aspect, the dispenser is configured to dispense the defoaming agent continuously or intermittently. In one aspect, the dispenser is configured to dispense the defoaming agent continuously or intermittently at a predetermined rate. A suitable rate for dispensing the condensate can be readily determined by those skilled in the art. In one aspect, the dispenser is provided to the condenser. In one aspect, the dispenser is provided to each condenser.

[0121] In one aspect, the unit includes a container containing the defoaming agent. In one aspect, the condenser and the container are arranged to be in fluid communication. In one aspect, each condenser and the container are arranged to be in fluid communication. By doing so, the condensate from the condenser can flow into the container containing the defoaming agent so as to be mixed with the defoaming agent.

[0122] The present invention will be described with reference to the following non-limiting examples.

Example

[0123] Example 1 - Effect of Antifoaming Agents on Foaming in Pyrolyzed Glucose Fragmentation Condensates 250 mL of condensate obtained from pyrolyzed glucose fragmentation was obtained. This condensate contained 8.3 g / L of glyoxal, 12.8 g / L of pyruvaldehyde (methylglyoxal), 89.3 g / L of glycolaldehyde, 15.2 g / L of formaldehyde, and 3.8 g / L of acetol (hydroxyacetone) in water.

[0124] 250 mL of this condensate was mixed with 12.5 mL of 2-propanol. The resulting mixture contained 5% by volume of 2-propanol based on the total volume of the mixture. 50.0 mL of this mixture was added to a 100 mL graduated cylinder equipped with a stopper. The height of the liquid (i.e., the height before shaking, see below) was recorded. The 50.0 mL of this mixture in the graduated cylinder was shaken 30 times in total for 10 seconds. The total height of the liquid and the bubbles was recorded. The height of the bubbles at 5 minutes after shaking was calculated as the difference between the total height at 5 minutes after shaking and the height of the liquid (before shaking).

[0125] The above experiment was repeated using 1% by volume of 2-propanol (instead of 5% by volume of 2-propanol) based on the total volume of the mixture.

[0126] Also, the above experiment was repeated using 20 ppmv of Silfoam SE47 (i.e., 0.002% by weight of Silfoam SE47) (instead of 5% by volume of 2-propanol) based on the total volume of the mixture. Silfoam SE47 is an oil-in-water emulsion based on polydimethylsiloxane and auxiliaries and had an active ingredient concentration of 17% by weight.

[0127] The above experiment was repeated even in the absence of 2-propanol.

[0128] Each of the above experiments was repeated three times, and the average height of the bubbles was calculated.

[0129] The results from the above experiments are shown in Figure 1. In Figure 1, the black bars represent the average difference between the height of the bubbles before shaking and the height of the bubbles immediately after shaking, and the white bars represent the average difference between the height of the bubbles before shaking and the height of the bubbles 5 minutes after shaking.

[0130] These results indicate that each of the antifoaming agents (2-propanol and Silfoam SE47) had an advantageous effect on the reduction and / or prevention of the height of the bubbles.

[0131] Example 2 - Layout of a continuous condensation process with an added antifoaming agent for producing pyrolyzed glucose fragmentation condensates A glucose syrup feed solution (60 wt% glucose and 40 wt% water based on the total weight of the feed solution) was subjected to pyrolytic fragmentation using the apparatus described in US10570078B2 (Patent Document 8). This included adding the glucose syrup feed solution into a fragmentation reactor. This pyrolytically fragmented the glucose syrup feed solution to produce a product gas 101 containing C1 - C3 oxygen-containing compounds (which includes a gas-phase oxygen-containing compound mixture). The product gas 101 may also contain a flushing gas, which may include the fluidization gas from the fragmentation reactor.

[0132] The product gas 101 was guided through a first indirect cooling heat exchanger and then through a filter to remove coarse particles, such as dust. In this specific example, the filter was a surface filtration device, although various other gas - solid filters (e.g., multicyclones) could also be used. Other cooling means could also be used. In some examples, the first indirect heat exchanger and the filter may not be used.

[0133] The product gas 101 exiting the filter was subjected to a condensation process as shown in Figure 2. This included feeding the filtered product gas 101 into a condenser 102 (a cooling tower in this example) containing a packing material 103. A portion of the product gas 101 flowing through the condenser 102 was condensed to produce condensate, which exited from the bottom of the condenser 102 under gravity. Typically, the remaining portion of the product gas 101 containing CO and CO2 (optionally and flushing gas) remained in the gaseous state and exited from the top of the condenser 102 through the gas outlet as a gas stream 104. The gas stream 104 exiting the gas outlet had a temperature from 10 to 20 °C, and the condensate exiting the condenser 102 had a temperature from 40 to 60 °C.

[0134] The condensate exiting the condenser 102 was guided to a pump 105 and then passed through an indirect plate heat exchanger 106. This cooled the condensate to a temperature from 10 to 20 °C. The condensate exiting the heat exchanger 106 was split into a condensate product stream 107A and a condensate recycle stream 107B. The mass ratio of the condensate recycle stream 107B to the condensate product stream 107A could be from 10:1 to 20:1 depending on the temperatures of the streams 107A and 107B and was 20:1 in this specific example. The condensate product stream 107A was collected.

[0135] An antifoaming agent 108 was added to the condensate recycle stream 107B. In this example, this was done before adding the condensate recycle stream 107B to the condenser 102 (as described below). The antifoaming agent was Silfoam SE47 as defined in Example 1.

[0136] A mixture of the condensate recycle stream 107B and the antifoaming agent 108 was added to the condenser 102.

[0137] Mixtures 107B, 108 may be split into at least two streams 109A, 109B. Each stream 109A, 109B may be added to condenser 102 at different parts of the condenser 102. For example, mixtures 107B, 108 may be added at or near the top of condenser 102 (as shown by stream 109A in FIG. 2), for example, on top of packing 103. For example, mixtures 107B, 108 may be added at or near the floor of the condenser (as shown by stream 109B in FIG. 2), for example, under packing 103.

[0138] Mixtures 107B, 108 (109A) added through the top of condenser 102 flowed downward through packing 103 under gravity. By doing so, mixtures 107B, 108 (109A) flowed countercurrently to product gas 101 and promoted effective and efficient condensation of product gas 101 in condenser 102 while preventing excessive foaming. Packing 103 in condenser 102 increased the contact surface between mixtures 107B, 108 (109A) and product gas 101. The packing was VFF Novalox-25-M AISI316, but it is clear that different packings may also be used. Condenser 102 and condensate recycle are operated continuously.

[0139] The amount of antifoaming agent 108 added to the agglomerator was approximately 0.2 mL per 1 kg of glucose syrup feed solution added to the pyrolytic fragmentation condenser. If antifoaming agent 108 is not used, an excessive amount of bubbles will be generated, which may overflow and / or block condenser 102 and / or other equipment, leading to performance degradation or equipment failure. The present invention addresses this problem.

[0140] It is apparent that the method of mixing the defoaming agent 108 with the condensate can be varied. It is also apparent that the condensation process can be carried out in a variety of different ways. For example, the method of recycling the condensate, as well as the nature of the equipment used and the way it is connected, can also be changed. For example, various other equipment such as filters and other unit operations can also be used. For example, alternative or additional cooling means can be used, for example, coolant can be added at the bottom of the condenser, under the packing material. It is also apparent that control and monitoring can be accomplished in a variety of different ways. In this specific example, the height of the liquid at the bottom of the condenser 102 was a controlled variable value. This can be achieved in a variety of ways, for example, by adjusting the amount of the mixtures 107B, 108 recycled to the condenser 102 (for example, by adjusting the flow rate of the mixtures 107B, 108 recycled to the condenser and / or the ratio of the flows 107A, 107B); and / or by adjusting the amount of the oxygen-containing compound mixture in the gas phase entering the condenser 102.

[0141] It is apparent to those skilled in the art that the unit operations, as well as any other features between the production of the fragmentation product 101 and the condensation process, can also be varied.

[0142] Various improvements and modifications of the present invention will be apparent to those skilled in the art without departing from the scope and spirit of the present invention. Although the present invention has been described in connection with specific preferred embodiments, it is to be understood that the invention as claimed should not be unduly limited to such specific embodiments. In fact, various improvements of the modes described for carrying out the present invention, which are apparent to those skilled in the chemical and related arts, are intended to be within the scope of the claims.

[0143] The aspects and modes described herein can be combined as known to those skilled in the art and at least as described below.

[0144] Aspect 1. A method of at least partially condensing an oxygen-containing compound mixture, comprising the following steps: (a) Providing a gaseous oxygen-containing compound mixture obtained from fragmentation of an aqueous solution of carbohydrates; (b) Performing at least partial condensation on the gaseous oxygen-containing compound mixture to provide a condensate; and (c) Mixing an antifoaming agent with the condensate; A method comprising the above steps.

[0145] Aspect 2. The method according to aspect 1, wherein the gaseous oxygen-containing compound mixture is derived from biomass.

[0146] Aspect 3. The method according to aspect 1 or 2, wherein the gaseous oxygen-containing compound mixture contains C1-C3 oxygen-containing compounds.

[0147] Aspect 4. The method according to any one of aspects 1 to 3, wherein the carbohydrate in the aqueous solution of carbohydrates is selected from monosaccharides, disaccharides, or mixtures thereof.

[0148] Aspect 5. The method according to any one of aspects 1 to 4, wherein the carbohydrate in the aqueous solution of carbohydrates is at least glucose.

[0149] Aspect 6. The method according to any one of aspects 1 to 5, wherein the carbohydrate in the aqueous solution of carbohydrates contains at least 40% by weight of monosaccharides based on the total amount of carbohydrates.

[0150] Aspect 7. The method according to any one of aspects 1 to 6, wherein the antifoaming agent contains one or more active ingredients independently selected from alcohols, ethers, carboxylic acids, esters, silicones, silicas, oils, waxes, and acrylates.

[0151] Aspect 8. The method according to aspect 7, wherein the one or more active ingredients are independently selected from alcohols, such as C1-C12 alcohols, or C1-C6 alcohols, or C1-C4 alcohols.

[0152] Aspect 9. The method according to aspect 7 or 8, wherein the defoaming agent substantially comprises, consists essentially of, or consists of the one or more active ingredients.

[0153] Aspect 10. The method according to aspect 7, wherein the one or more active ingredients are independently selected from silicones such as polydimethylsiloxanes.

[0154] Aspect 11. The method according to any one of aspects 7 to 10, wherein the defoaming agent has a total active ingredient content of from 0.0000001% by weight to 100% by weight, based on the total weight of the defoaming agent.

[0155] Aspect 12. The method according to any one of aspects 1 to 11, wherein mixing the defoaming agent and the condensate comprises adding the defoaming agent to the condensate.

[0156] Aspect 13. The method according to aspect 12, wherein the defoaming agent is added to the condensate at a rate of from 0.0000001 mL / h to 200 mL / h.

[0157] Aspect 14. The method according to any one of aspects 1 to 13, wherein the fragmentation of the aqueous solution of the carbohydrate for providing the gas-phase oxygen-containing compound mixture comprises adding the aqueous solution of the carbohydrate to a fragmentation reactor and subjecting the aqueous solution of the carbohydrate to pyrolytic fragmentation.

[0158] Aspect 15. The method according to any one of aspects 1 to 14, wherein in the mixed defoaming agent and condensate, the mass ratio of the defoaming agent to the condensate is from 1:1000000 to 1:1.

[0159] Aspect 16. The method according to any one of aspects 1 to 15, wherein in step (b), the gas-phase oxygen-containing compound mixture is at least partially condensed at a temperature from 0 to 150°C.

[0160] Aspect 17. The method according to any one of Aspects 1 to 16, wherein at least partial condensation of the vapor-phase oxygen-containing compound mixture is carried out by passing an input stream containing the vapor-phase oxygen-containing compound mixture through a condenser to provide the condensate and an output stream.

[0161] Aspect 18. The method according to Aspect 17, wherein at least partial condensation of the vapor-phase oxygen-containing compound mixture includes recycling at least a portion of the output stream into the input stream.

[0162] Aspect 19. The method according to Aspect 17 or 18, wherein at least partial condensation of the vapor-phase oxygen-containing compound mixture includes dividing the condensate into at least a condensate product stream and a condensate recycle stream, and adding the condensate recycle stream to the condenser.

[0163] Aspect 20. The method according to Aspect 19, wherein mixing the antifoaming agent and the condensate includes adding the antifoaming agent to the condensate recycle stream to provide a mixture and adding this mixture to the condenser.

[0164] Aspect 21. The method according to Aspect 20, wherein the mixture added to the condenser has a temperature from 0 to 30 °C.

[0165] Aspect 22. The method according to any one of Aspects 1 to 21, which is a continuous process.

[0166] Aspect 23. The method according to any one of Aspects 1 to 22, including a further step of recovering the condensate.

[0167] Aspect 24. The method according to any one of Aspects 1 to 23, wherein the fragmentation of the aqueous solution of the carbohydrate is thermal fragmentation.

[0168] Aspect 25. The method according to any one of Aspects 1 to 24, wherein step (b) is carried out on an oxygen-containing compound mixture directly obtained from the fragmentation of an aqueous solution of a carbohydrate.

[0169] Aspect 26. An apparatus configured to at least partially condense a mixture of oxygen-containing compounds, comprising: (a) A fragmentation reactor configured to fragment an aqueous solution of carbohydrates to provide a gaseous-phase mixture of oxygen-containing compounds; (b) A condenser configured to at least partially condense the gaseous-phase mixture of oxygen-containing compounds to provide a condensate; and (c) A unit configured to mix an anti-foaming agent with the condensate. The apparatus as described above.

[0170] Aspect 27. The apparatus according to Aspect 26, wherein the fragmentation reactor is selected from a pyrolysis fragmentation reactor and a fluidized bed reactor, such as a bubbling bed reactor, a turbulent bed reactor, or a riser reactor.

[0171] Aspect 28. The apparatus according to Aspect 26 or 27, wherein the fragmentation reactor includes a feed inlet, a product outlet, a riser, and a fluidization gas inlet.

[0172] Aspect 29. The apparatus according to any one of Aspects 26 to 28, further including a separator configured to separate particulate matter from the gaseous-phase mixture of oxygen-containing compounds.

Claims

1. A method for at least partially condensing a mixture of oxygen-containing compounds, comprising the following steps: (a) providing a gaseous-phase oxygen-containing compound mixture obtained from the fragmentation of an aqueous solution of carbohydrates; (b) performing at least partial condensation on the gaseous-phase oxygen-containing compound mixture to provide a condensate; (c) mixing an antifoaming agent with the condensate; The method as described above.

2. The method according to claim 1, wherein the gaseous-phase oxygen-containing compound mixture is derived from biomass.

3. The method according to claim 1 or 2, wherein the gaseous-phase oxygen-containing compound mixture contains C1-C3 oxygen-containing compounds.

4. The method according to any one of claims 1 to 3, wherein the carbohydrates in the aqueous solution of carbohydrates are selected from monosaccharides, disaccharides, or mixtures thereof.

5. The method according to any one of claims 1 to 4, wherein the carbohydrates in the aqueous solution of carbohydrates contain at least 40% by weight of monosaccharides based on the total amount of carbohydrates.

6. The method according to any one of claims 1 to 5, wherein the antifoaming agent contains one or more active ingredients independently selected from alcohols, ethers, carboxylic acids, esters, silicones, silicas, oils, waxes, and acrylates.

7. The method according to claim 6, wherein the antifoaming agent has a total active ingredient content of from 0.0000001% to 100% by weight based on the total weight of the antifoaming agent.

8. The method according to any one of claims 1 to 7, wherein mixing the antifoaming agent with the condensate includes adding the antifoaming agent to the condensate.

9. The method according to claim 8, wherein the antifoaming agent is added to the condensate at a rate of from 0.0000001 mL / h to 200 mL / h.

10. The method according to any one of claims 1 to 9, wherein the fragmentation of the aqueous solution of carbohydrates for providing the gaseous-phase oxygen-containing compound mixture includes adding the aqueous solution of carbohydrates to a fragmentation reactor and subjecting the aqueous solution of carbohydrates to pyrolytic fragmentation.

11. The method according to any one of claims 1 to 10, wherein in the mixed antifoaming agent and condensate, the mass ratio of the antifoaming agent to the condensate is from 1:1000000 to 1:

1.

12. The method according to any one of claims 1 to 11, wherein in step (b), the vapor-phase oxygen-containing compound mixture is at least partially condensed at a temperature from 0 to 150 °C.

13. The method according to any one of claims 1 to 12, wherein the at least partial condensation of the vapor-phase oxygen-containing compound mixture is carried out by passing an input stream containing the vapor-phase oxygen-containing compound mixture through a condenser to provide the condensate and an output stream.

14. The method according to claim 13, wherein the at least partial condensation of the vapor-phase oxygen-containing compound mixture includes recycling at least a portion of the output stream to the input stream.

15. The method according to claim 13 or 14, wherein the at least partial condensation of the vapor-phase oxygen-containing compound mixture includes dividing the condensate into at least a condensate product stream and a condensate recycle stream and adding the condensate recycle stream to the condenser.

16. The method according to claim 15, wherein mixing the antifoaming agent and the condensate includes adding the antifoaming agent to the condensate recycle stream to form a mixture and adding this mixture to the condenser.

17. The method according to any one of claims 1 to 16, wherein step (b) is carried out on an oxygen-containing compound mixture directly obtained from the fragmentation of an aqueous solution of carbohydrates.

18. An apparatus configured to at least partially condense an oxygen-containing compound mixture, (a) a fragmentation reactor configured to fragment an aqueous solution of carbohydrates to provide a vapor-phase oxygen-containing compound mixture; (b) a condenser configured to at least partially condense the vapor-phase oxygen-containing compound mixture to provide a condensate; and (c) a unit configured to mix an antifoaming agent and the condensate; The apparatus comprising the above.

19. The apparatus according to claim 18, wherein the fragmentation reactor is a pyrolysis fragmentation reactor; and a fluidized bed reactor, such as a bubbling bed reactor, a turbulent bed reactor, or a riser-type reactor.

20. The apparatus according to claim 18 or 19, wherein the fragmentation reactor includes a feed inlet; and a product outlet; a riser; and a fluidizing gas inlet.

21. The apparatus according to any one of claims 18 to 20, including a separator configured to separate particulate matter from the vapor-phase oxygen-containing compound mixture.

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