Energy-efficient process for preparing one or more ethers
By integrating an open loop heat pump to recover heat from an overhead stream and transfer it to an H2O-containing stream, the process addresses energy inefficiencies and emissions in ether production, achieving efficient and sustainable ether production.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2025-09-18
- Publication Date
- 2026-03-26
AI Technical Summary
Existing processes for producing ethers are energy-intensive and generate high greenhouse gas emissions, particularly during product separation in fractionating columns, and recycling heated H2O-containing streams is challenging due to pressure differences.
Integrating an open loop heat pump to recover heat from an overhead stream and transfer it to an H2O-containing stream, which can be used for other chemical processes, reducing emissions and improving overall energy efficiency.
The process reduces greenhouse gas emissions and enhances energy efficiency by recovering heat for other chemical processes, allowing for the effective recycling of H2O-containing streams.
Abstract
Description
240190W001Energy-efficient process for preparing one or more ethersThe present invention relates to a process for preparing one or more ethers, wherein the process includes a heat transfer step for recovering heat.TECHNICAL FIELDThe present invention relates to a process for preparing one or more ethers, the process comprising a step of transferring heat from an overhead stream obtained from a fractionating column to an H2O-containing stream, obtaining a heated H2O-containing stream and a cooled overhead stream.INTRODUCTIONProduction of ethers can be conducted according to known processes by reacting an alcohol with an epoxide in the presence of a catalyst, wherein methanol, butanol and hexanol are most often used as alcohol and wherein ethylene oxide and propylene oxide are most often used as epoxide. As a catalyst, the corresponding alcoholate can be used, preferably as sodium salt. In a plant, monoethers as well as di-, tri-, and tetra-ethers can be produced accordingly.CN 1044472 C relates to a preparation method of tetraethylene glycol, the method including reacting ethylene oxide and raw material glycol in the presence of an alkaline catalyst (see claim 1). US 3935279 A relates to a process for the production of ethylene glycol ethers by the reaction of ethylene oxide with C1-C4 aliphatic alcohols.The known processes have the drawbacks of generating high emissions of greenhouse gases and of needing high amounts of energy, in particular for separating the products and by-products from each other in one or more fractionating columns. Thus, there was a need to provide a process being comparatively energy-efficient.Preparation of monoethers like ethylene glycol monobutyl ether, propylene glycol monobutyl ether, ethylene glycol monomethyl ether, and ethylene glycol monohexyl ether usually requires an H2O-containing stream having a pressure of about 16 bara as heat source. Therefore, it is difficult to recycle obtained heated H2O-containing stream back into the process, since it typically has a different pressure.240190W001- 2 -DETAILED DESCRIPTIONThus, it was a subject of the present invention to provide a process for preparing one or more ethers, wherein the process includes a heat transfer step for recovering heat.Surprisingly, it has been found that by integrating an open loop heat pump in the process for preparing one or more ethers, a portion of the heat can be recovered by heat transfer to an H2O-containing stream, which can be used for other chemical processes. Thus, it has been found that emissions of greenhouse gases can be reduced with the process of the present invention, and that in particular the overall energy efficiency can be improved.Thus, the present invention relates to a process for preparing one or more ethers, preferably two or more ethers, the process comprising(i) preparing a feed stream comprising an alcohol, an epoxide, and a catalyst;(ii) feeding the feed stream prepared in (i) into a reactor, and subjecting the feed stream to reaction conditions, obtaining a product stream comprising the one or more ethers, preferably two or more ethers;(iii) feeding the product stream obtained from (ii) into a first fractionating column, and separating the product stream into a first overhead stream, wherein the first overhead stream is preferably gaseous, and a first bottoms stream, wherein the first bottoms stream is preferably liquid;(iv) preparing a first H2O-containing stream, wherein the first H2O-containing stream is preferably liquid;(v) transferring heat from the first overhead stream obtained from (iii) to the first H2O-contain- ing stream prepared in (iv), obtaining a heated first H2O-containing stream, wherein the heated first H2O-containing stream is preferably gaseous, and a liquid first overhead stream.It is preferred that the one or more ethers are selected from the group consisting of ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, propylene glycol monobutyl ether, dipropylene glycol monobutyl ether, tripropylene glycol monobutyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, triethylene glycol monohexyl ether, and mixtures of two or more thereof.240190W001- 3 -It is preferred that the one or more ethers comprise a monoether, wherein the monoether is more preferably selected from the group consisting of ethylene glycol monobutyl ether, propylene glycol monobutyl ether, ethylene glycol monomethyl ether, ethylene glycol monohexyl ether, and mixtures of two or more thereof.It is preferred that the alcohol comprised in the feed stream prepared in (i) is selected from the group consisting of methanol, butanol, hexanol, and mixtures of two or more thereof.In the context of the present invention, indication of butane and hexane refers to n-butane and n-hexane, respectively, if not stated otherwise. Similarly, suffixes butyl and hexyl relate to n-bu- tyl and n-hexyl, respectively.It is preferred that the epoxide comprised in the feed stream prepared in (i) is selected from the group consisting of propylene oxide, ethylene oxide, and mixtures of two or more thereof.It is preferred that the catalyst comprised in the feed stream prepared in (i) comprises one or more of a methanolate, a butanolate, a hexylglycolate, and mixtures of two or more thereof, wherein the catalyst more preferably comprises, more preferably consists of, sodium methanolate, sodium butanolate, sodium hexylglycolate, and mixtures of two or more thereof.It is preferred that the reaction conditions according to (ii) comprise heating the feed stream to a temperature in the range of from 110 to 235 °C, more preferably in the range of from 115 to 230 °C.It is preferred that the reaction conditions comprise adiabatic conditions.It is preferred that the reactor comprises an inlet end and an outlet end.In the case wherein the reactor comprises an inlet end and an outlet end, it is preferred that the reaction conditions according to (ii) comprise a temperature at the inlet end in the range of from 110 to 185 °C, more preferably of from 115 to 180 °C.Further in the case wherein the reactor comprises an inlet end and an outlet end, it is preferred that the reaction conditions according to (ii) comprise a temperature at the outlet end of the reactor in the range of from 180 to 235 °C, more preferably of from 185 to 230 °C.Further in the case wherein the reactor comprises an inlet end and an outlet end, it is preferred that the reaction conditions according to (ii) comprise a pressure at the outlet end of the reactor240190W001- 4 - in the range of from 10 to 40 bara, more preferably in the range of from 15 to 35 bara, more preferably in the range of from 17 to 33 bara.It is preferred that the product stream obtained from (ii) is fed according to (iii) into the first fractionating column having a pressure in the range of from 400 to 1160 mbara, more preferably in the range of from 425 to 1125 mbara, more preferably in the range of from 450 to 1100 mbara.It is preferred that the first overhead stream obtained from (iii) has a temperature in the range of from 71 to 174 °C, more preferably in the range of from 100 to 169 °C, more preferably in the range of from 110 to 160 °C.It is preferred that the first overhead stream obtained from (iii) has a pressure in the range of from 400 to 1160 mbara, more preferably in the range of from 425 to 1125 mbara, more preferably in the range of from 450 to 1100 mbara.It is preferred that the first H2O-containing stream prepared in (iv) has a temperature in the range of from 66 to 169 °C, more preferably in the range of from 95 to 164 °C, more preferably in the range of from 105 to 155 °C.It is preferred that a difference of the temperature of the first overhead stream obtained from (iii) and the temperature of the first H2O-containing stream prepared in (iv) is in the range of from 5 to 20 K, more preferably of from 10 to 15 K.It is preferred that heat is transferred according to (v) with a heat exchanger.It is preferred that the liquid first overhead stream obtained from (v) has a temperature in the range of from 70 to 120 °C, more preferably in the range of from 90 to 110 °C, more preferably in the range of from 100 to 105 °C.It is preferred that the process further comprises(vi) feeding the first bottoms stream obtained from (iii) in a second fractionating column, and separating the first bottoms streams into a second overhead stream, wherein the second overhead stream is more preferably gaseous, and a second bottoms stream, wherein the second bottoms stream is more preferably liquid.In the case wherein the process further comprises feeding the first bottoms stream obtained from (iii) in a second fractionating column, and separating the first bottoms streams into a second overhead stream and a second bottoms stream according to (vi), it is preferred that the first240190W001- 5 - bottoms stream obtained from (iii) is fed according to (vi) into the second fractionating column having a temperature in the range of from 100 to 215 °C, more preferably in the range of from 120 to 205 °C, more preferably in the range of from 140 to 195 °C.Further in the case wherein the process further comprises feeding the first bottoms stream obtained from (iii) in a second fractionating column, and separating the first bottoms streams into a second overhead stream and a second bottoms stream according to (vi), it is preferred that the second overhead stream obtained from (vi) has a temperature in the range of from 85 to 145 °C, more preferably in the range of from 90 to 140 °C, more preferably in the range of from 95 to 135 °C.Further in the case wherein the process further comprises feeding the first bottoms stream obtained from (iii) in a second fractionating column, and separating the first bottoms streams into a second overhead stream and a second bottoms stream according to (vi), it is preferred that the second overhead stream obtained from (vi) has a pressure in the range of from 25 to 350 mbara, more preferably in the range of from 50 to 250 mbara, more preferably in the range of from 75 to 160 mbara.Further in the case wherein the process further comprises feeding the first bottoms stream obtained from (iii) in a second fractionating column, and separating the first bottoms streams into a second overhead stream and a second bottoms stream according to (vi), it is preferred that the process further comprises(vii) preparing a second H2O-containing stream, wherein the second H2O-containing stream is more preferably liquid,(viii) transferring heat from the second overhead stream obtained from (vi) to the second H2O- containing stream prepared in (vii), obtaining a heated second H2O-containing stream, wherein the heated second H2O-containing stream is more preferably gaseous, and a liquid second overhead stream.In the case wherein the process further comprises preparing a second H2O-containing stream according to (vii) and transferring heat from the second overhead stream obtained from (vi) to the second H2O-containing stream prepared in (vii), obtaining a heated second H2O-containing stream and a liquid second overhead stream according to (viii), it is preferred that the second H2O-containing stream prepared in (vii) has a temperature in the range of from 80 to 140 °C, more preferably in the range of from 85 to 135 °C, more preferably in the range of from 90 to 130 °C.240190W001- 6 -Further in the case wherein the process further comprises preparing a second H2O-containing stream according to (vii) and transferring heat from the second overhead stream obtained from (vi) to the second H2O-containing stream prepared in (vii), obtaining a heated second H2O-con- taining stream and a liquid second overhead stream according to (viii), it is preferred that a difference of the temperature of the second overhead stream obtained from (vi) and the temperature of the second H2O-containing stream prepared in (vii) is in the range of from 5 to 20 K, more preferably of from 10 to 15 K.Further in the case wherein the process further comprises preparing a second H2O-containing stream according to (vii) and transferring heat from the second overhead stream obtained from (vi) to the second H2O-containing stream prepared in (vii), obtaining a heated second H2O-con- taining stream and a liquid second overhead stream according to (viii), it is preferred that heat is transferred according to (viii) with a heat exchanger.It is preferred that the heated first H2O-containing stream obtained from (v) and the heated second H2O-containing stream obtained from (viii) independently from one another have a temperature in the range of from 66 to 169 °C, preferably in the range of from 85 to 164 °C, more preferably in the range of from 90 to 155 °C.It is preferred that the heated first H2O-containing stream obtained from (v) is gaseous, and that the process further comprises(ix) compressing the gaseous first H2O-containing stream obtained from (v), wherein the gaseous first H2O-containing stream obtained from (v) is more preferably compressed to a pressure in the range of from 2.6 to 7.1 bara, more preferably in the range of from 2.7 to 6.6 bara, more preferably in the range of from 3.0 to 5.0 bara, more preferably in the range of from 3.5 to 4.5 bara.It is preferred that the heated second H2O-containing stream obtained from (viii) is gaseous, and that the process further comprises(x) compressing the gaseous second H2O-containing stream obtained from (viii), wherein the gaseous second H2O-containing stream obtained from (viii) is more preferably compressed to a pressure in the range of from 2.6 to 7.1 bara, more preferably in the range of from 2.7 to 6.6 bara, more preferably in the range of from 3.0 to 5.0 bara, more preferably in the range of from 3.5 to 4.5 bara.It is preferred that the process further comprises240190W001- 7 -(xi) using the heated first H2O-containing stream obtained from (v) and the heated second H2O-containing stream obtained from (viii) independently from one another as direct or indirect heat source for a chemical process, wherein the chemical process is more preferably not for preparing one or more ethers, wherein the chemical process more preferably comprises preparing one or more of styrene and n-butylacrylate.In the case wherein the process further comprises using the heated first H2O-containing stream obtained from (v) and the heated second H2O-containing stream obtained from (viii) independently from one another as direct or indirect heat source for a chemical process according to (xi), it is preferred that using the heated first H2O-containing stream obtained from (v) and the heated second H2O-containing stream obtained from (viii) as direct heat source for a chemical process independently from one another comprises transferring heat from the heated first H2O- containing stream obtained from (v) and / or from the heated second H2O-containing stream obtained from (viii) to a process stream used in the chemical process.Further in the case wherein the process further comprises using the heated first H2O-containing stream obtained from (v) and the heated second H2O-containing stream obtained from (viii) independently from one another as direct or indirect heat source for a chemical process according to (xi), it is preferred that using the heated first H2O-containing stream obtained from (v) and the heated second H2O-containing stream obtained from (viii) as indirect heat source for a chemical process independently from one another comprises transferring heat from the heated first H2O- containing stream obtained from (v) and / or from the heated second H2O-containing stream obtained from (viii) to a stream comprising a heat transfer medium and transferring heat from the stream comprising a heat transfer medium to a process stream used in the chemical process.It is preferred that the heated H2O-containing stream obtained from (v) is not recycled into the process according to embodiment 1 , wherein the heated H2O-containing stream obtained from (v) is more preferably not recycled into a process for preparing one or more ethers.According to a first alternative, it is preferred that the alcohol comprised in the feed stream prepared in (i) is butanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, the catalyst comprised in the feed stream prepared in (i) is butanolate, wherein the one or more ethers more preferably comprise, more preferably consist of, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, and triethylene glycol monobutyl ether.240190W001- 8 -In the case wherein the alcohol comprised in the feed stream prepared in (i) is butanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is butanolate according to the first alternative, it is preferred that the first overhead stream obtained from (iii) comprises a portion of the alcohol, and that the first bottoms stream obtained from (iii) comprises a portion of the one or more ethers.Further in the case wherein the alcohol comprised in the feed stream prepared in (i) is butanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is butanolate according to the first alternative, it is preferred that the first overhead stream obtained from (iii) has a temperature in the range of from 110 to 160 °C, more preferably in the range of from 115 to 155 °C, more preferably in the range of from 120 to 145 °C.Further in the case wherein the alcohol comprised in the feed stream prepared in (i) is butanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is butanolate according to the first alternative, it is preferred that the first overhead stream obtained from (iii) has a pressure in the range of from 30 to 85 mbara, more preferably in the range of from 35 to 80 mbara, more preferably in the range of from 40 to 75 mbara.Further in the case wherein the alcohol comprised in the feed stream prepared in (i) is butanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is butanolate according to the first alternative, it is preferred that the second overhead stream obtained from (vi) comprises a first portion of the one or more ethers, wherein the second overhead stream obtained from (vi) preferably comprises ethylene glycol monobutyl ether, and wherein the second bottoms stream obtained from (vi) comprises a second portion of the one or more ethers, wherein the second bottoms stream obtained from (vi) more preferably comprises one or more of diethylene glycol monobutyl ether and triethylene glycol monobutyl ether.According to a second alternative, it is preferred that the alcohol comprised in the feed stream prepared in (i) is butanol, the epoxide comprised in the feed stream prepared in (i) is propylene oxide, and the catalyst comprised in the feed stream prepared in (i) is butanolate, wherein the one or more ethers preferably comprise, more preferably consist of, propylene glycol monobutyl ether, dipropylene glycol monobutyl ether, and tripropylene glycol monobutyl ether.240190W001- 9 -In the case wherein the alcohol comprised in the feed stream prepared in (i) is butanol, the epoxide comprised in the feed stream prepared in (i) is propylene oxide, and the catalyst comprised in the feed stream prepared in (i) is butanolate according to the second alternative, it is preferred that the first overhead stream obtained from (iii) comprises a portion of the alcohol, and wherein the first bottoms stream obtained from (iii) comprises a portion of the one or more ethers.Further in the case wherein the alcohol comprised in the feed stream prepared in (i) is butanol, the epoxide comprised in the feed stream prepared in (i) is propylene oxide, and the catalyst comprised in the feed stream prepared in (i) is butanolate according to the second alternative, it is preferred that the first overhead stream obtained from (iii) has a temperature in the range of from 110 to 145 °C, more preferably in the range of from 115 to 140 °C, more preferably in the range of from 120 to 135 °C.Further in the case wherein the alcohol comprised in the feed stream prepared in (i) is butanol, the epoxide comprised in the feed stream prepared in (i) is propylene oxide, and the catalyst comprised in the feed stream prepared in (i) is butanolate according to the second alternative, it is preferred that the first overhead stream obtained from (iii) has a pressure in the range of from 45 to 90 mbara, more preferably in the range of from 50 to 85 mbara, more preferably in the range of from 55 to 80 mbara.Further in the case wherein the alcohol comprised in the feed stream prepared in (i) is butanol, the epoxide comprised in the feed stream prepared in (i) is propylene oxide, and the catalyst comprised in the feed stream prepared in (i) is butanolate according to the second alternative, it is preferred that the second overhead stream obtained from (vi) comprises a first portion of the one or more ethers, wherein the second overhead stream obtained from (vi) more preferably comprises propylene glycol monobutyl ether, and wherein the second bottoms stream obtained from (vi) comprises a second portion of the one or more ethers, wherein the second bottoms stream obtained from (vi) more preferably comprises one or more of dipropylene glycol monobutyl ether and tripropylene glycol monobutyl ether.According to a third alternative, it is preferred that the alcohol comprised in the feed stream prepared in (i) is methanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is methanolate, wherein the one or more ethers more preferably comprise, more preferably consist of, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, and triethylene glycol monomethyl ether.240190W001- 10 -In the case wherein the alcohol comprised in the feed stream prepared in (i) is methanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is methanolate according to the third alternative, it is preferred that the first overhead stream obtained from (iii) comprises a first portion of the one or more ethers, wherein the first overhead stream obtained from (iii) more preferably comprises ethylene glycol monomethyl ether, and wherein the first bottoms stream obtained from (iii) comprises a second portion of the one or more ethers, wherein the first bottoms stream obtained from (iii) more preferably comprises one or more of diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, and tetraethylene glycol monomethyl ether.Further in the case wherein the alcohol comprised in the feed stream prepared in (i) is methanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is methanolate according to the third alternative, it is preferred that the first overhead stream obtained from (iii) has a temperature in the range of from 110 to 155 °C, more preferably in the range of from 115 to 150 °C, more preferably in the range of from 120 to 145 °C.Further in the case wherein the alcohol comprised in the feed stream prepared in (i) is methanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is methanolate according to the third alternative, it is preferred that the first overhead stream obtained from (iii) has a pressure in the range of from 0.35 to 0.95 bara, more preferably in the range of from 0.40 to 0.90 bara, more preferably in the range of from 0.45 to 0.85 bara.Further in the case wherein the alcohol comprised in the feed stream prepared in (i) is methanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is methanolate according to the third alternative, it is preferred that the second overhead stream obtained from (vi) comprises a first portion of the one or more ethers, wherein the second overhead stream obtained from (vi) more preferably comprises ethylene glycol monomethyl ether, and wherein the second bottoms stream obtained from (vi) comprises a second portion of the one or more ethers, wherein the second bottoms stream obtained from (vi) preferably comprises one or more of ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, and tetraethylene glycol monomethyl ether.According to a fourth alternative, it is preferred that the alcohol comprised in the feed stream prepared in (i) is hexanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is hexanolate, wherein the240190W001- 11 - one or more ethers more preferably comprise, more preferably consist of, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, and triethylene glycol monohexyl ether.In the case wherein the alcohol comprised in the feed stream prepared in (i) is hexanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is hexanolate according to the fourth alternative, it is preferred that the first overhead stream obtained from (iii) comprises a portion of the alcohol, and wherein the first bottoms stream obtained from (iii) comprises a portion of the one or more ethers.Further in the case wherein the alcohol comprised in the feed stream prepared in (i) is hexanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is hexanolate according to the fourth alternative, it is preferred that the first overhead stream obtained from (iii) has a temperature in the range of from 140 to 175 °C, more preferably in the range of from 145 to 170 °C, more preferably in the range of from 150 to 165 °C.Further in the case wherein the alcohol comprised in the feed stream prepared in (i) is hexanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is hexanolate according to the fourth alternative, it is preferred that the first overhead stream obtained from (iii) has a pressure in the range of from 930 to 1250 mbara, preferably in the range of from 955 to 1225 mbara, more preferably in the range of from 980 to 1200 mbara.Further in the case wherein the alcohol comprised in the feed stream prepared in (i) is hexanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is hexanolate according to the fourth alternative, it is preferred that the second overhead stream obtained from (vi) comprises a portion of the alcohol, and wherein the second bottoms stream obtained from (vi) comprises a second portion of the one or more ethers, wherein the second bottoms stream obtained from (vi) more preferably comprises one or more of ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, and triethylene glycol monohexyl ether.It is preferred that the process further comprises(xii) recycling at least a portion of the liquid first overhead stream obtained from (v) into the feed stream according to (i).It is preferred that the process is a continuous process.240190W001- 12 -Further, the present invention relates to a process, preferably a process according to any one of the embodiments disclosed herein, comprising a step of converting the one or more ethers obtainable or obtained by the process according to any one of the embodiments disclosed herein to obtain a product Q.In the context of the presently described process, a H2O-containing stream can be provided, in particular for recycling into the process itself and also for further use in other processes, whereby the H2O-containing stream can be provided in various pressure and temperature ranges, preferably as steam stream. This relates in particular to the heated first H2O-containing stream obtained from heat transfer according to (v), the gaseous third H2O-containing stream obtained from expanding according to (ix), the heated second H2O-containing stream obtained from heat transfer according to (viii), and the gaseous fifth H2O-containing stream obtained from expanding according to (x).With regard to said streams, it is preferable that they are present in gaseous form, i.e. as water vapor. The steam can also be obtained at low pressures, in particular in the vacuum. The steam obtained is preferably compressed further, as also described in the embodiments herein, for example according to process step (xi) as defined in embodiments 29 and 30. Compression of a gaseous H2O-containing stream can be carried out by means of one or more compressors, preferably a cascade of compressors. The compressors used can be displacer machines and / or turbomachines, for example screw compressors, centrifugal blowers, radial turbo compressors, such as integrally geared compressors, and / or axial turbo compressors. Compression preferably involves feeding water to spray off the steam downstream of a compressor, to increase the efficiency of compression. Preferably, the water is sprayed (atomized) in order to accelerate evaporation.The compressed steam can be fed into a steam network.The compressed steam can be used in the plant used for preparing one or more ethers or in neighboring plants for the (trace) heating of apparatus and pipelines (e.g. for frost protection in winter), preferably at a pressure in the range of 0.5 to 2.0 barg. Alternatively, the compressed steam can be used to heat evaporators and reactors in neighboring systems (e.g. to reduce the amount of steam drawn from the steam network). For example, it can be sufficient to compress the steam to 3 barg.According to a further aspect, the present invention relates to a process, preferably to the process as described above, which (further) comprises a step of converting the one or more ethers240190W001- 13 - obtainable by or obtained by the process described herein or a chemical material obtainable by or obtained by the process described herein to obtain a product Q. Yet further, the present invention relates to a process comprising a step of using the one or more ethers as described herein; and preferably converting the one or more ethers to obtain a product Q.Yet further, the present invention relates to a product Q, preferably a product Q according to any one of the embodiments described herein, obtained or obtainable by a process using a H2O- containing stream obtained from the described process, in particular using one or more of the heated first H2O-containing stream obtained from heat transfer according to (v), the gaseous third H2O-containing stream obtained from expanding according to (ix), the heated second H2O- containing stream obtained from heat transfer according to (viii), and the gaseous fifth H2O-con- taining stream obtained from expanding according to (x).Preferably, the product Q is selected from: building block or monomer; or polymer, preferably polymer A, polymer composition, preferably polymer composition A, or polymer product, preferably polymer product A; or industrial use polymer, industrial use surfactant, descaling compound, industrial use biocide, industrial use solvent, industrial use dispersant, composition thereof or formulation thereof; or agrochemical composition, agrochemical formulation auxiliary or agrochemically active ingredient; or active pharmaceutical ingredient or intermediate thereof, pharmaceutical excipient, animal feed additive, human food additive, dietary supplements, aroma chemical or aroma composition; or aqueous polymer dispersion, preferably polyurethane or polyurethane - poly(meth)acry- late hybrid polymer dispersion, emulsion, binder for paper and fiber coatings, UV-curable acrylic polymer for hot melts and coatings polyisocyanates, hyperbranched polyester polyol, polymeric dispersant for inorganic binder compositions, unsaturated polyester polyol or 100% curable composition; or cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter, further cosmetic ingredient or composition or formulation thereof; or polymer B, polymer composition B, coating composition, other functional composition, foil, molded body, coating or coated substrate.Regarding this process from which the product Q, is obtained, it is preferred: that the content of the one or more ethers and of compounds derived from the one or more ethers, calculated as sum of the molecular weights of the one or more ethers, in the product Q,240190W001- 14 - is 1 weight-% or more, preferably 2 weight-% or more, more preferably 5 weight-% or more, more preferably 15 weight-% or more, more preferably 30 weight-% or more, more preferably 40 weight-% or more, more preferably 60 weight-% or more, more preferably 80 weight-% or more, more preferably 90 weight-% or more, more preferably 95 weight-% or more; and / or that the content of the one or more ethers and of compounds derived from the one or more ethers, calculated as sum of the molecular weights of the one or more ethers, in the product Q is 100 weight-% or less, preferably 95 weight-% or less, more preferably 90 weight-% or less, more preferably 50 weight-% or less, more preferably 25 weight-% or less, more preferably 10 weight-% or less; wherein it is more preferred that the respective content is determined based on identity preservation and / or segregation and / or mass balance and / or book and claim chain of custody models, preferably based on mass balance, preferably the International Sustainability and Carbon Certification (ISCC) standard.The publication Prior Art Disclosure; Issue 684; paragraphs
[1000] to
[8005] ; ISSN: 2198-4786; published: February 12, 2024 will be regarded as Reference RF1 , which is incorporated herein by reference in its entirety. Preferably, the product Q is a product as described in Reference RF1 ; paragraphs
[1000] to
[8005] , Preferably, the process described herein is further a process for the production of a product.The converting step to obtain the product Q preferably comprises one or more step(s) as described below and can be performed by conventional methods well known to a person skilled in the art. The converting step preferably comprises one or more step(s) selected from: recycling, preferably depolymerizing, gasifying, pyrolyzing, and / or steam cracking; and / or purifying, preferably crystallizing, (solvent) extracting, distilling, evaporating, hydrotreating, absorbing, adsorbing and / or subjecting to ion exchanger; and / or assembling, preferably foaming, synthesizing, chemical conversion, chemically transforming, polymerizing and / or compounding; and / or forming, preferably foaming, extruding and / or molding; and / or finishing, preferably coating and / or smoothing.In addition, the one or more step(s) are described in detail in Reference RF1 ; paragraphs
[1000] to
[8005] ,The term “building block”, as used in the context of the product Q herein, comprises compounds, which are in a gaseous, liquid or solid state under standard conditions of 0°C and 0.1 MPa. Building blocks are typically used in chemical industry to form secondary products, which provide a higher structural complexity and / or higher molecular weight than the building block on which the secondary product is based. The building block is preferably selected from the group240190W001- 15 - consisting of hydrogen, carbon monoxide, carbon dioxid, ethylene oxide, ethylene glycols, syngas comprising a mixture of hydrogen and carbon monoxide, alkanes, alkenes, alkynes and aromatic compounds. The alkanes, alkenes, alkynes and aromatic compounds comprise in particular 1 to 12 carbon atoms, respectively.The term “monomer”, as used in the context of the product Q herein, comprises molecules, which can react with each other to form polymer chains by polymerization. The monomer is preferably selected from the group consisting of (meth)acrylic acid, salts of (meth)acrylic acid; in particular sodium, potassium and zinc salts; (meth)acrolein and (meth)acrylates. (Methacrylates comprising 1 to 22 carbon atoms are preferred, in particular comprising 1 to 8 carbon atoms. The terms (meth)acrylic acid, (meth)acrolein or (meth)acrylate relate to acrylic acid, acrolein or acrylate and also to methacrylic acid, methacrolein or methacrylate, where applicable. Further, the monomer can be selected from hexamethylenediamine (HMD) and adipic acid.The building block can further be an intermediate compound. The term “intermediate compound”, as used in the context of the product Q herein, comprises organic reagents, which are applied for formation of compounds with higher molecular complexity. The intermediate compound can be selected for example from the group consisting of phosgene, polyisocyanates and propylene oxide. The polyisocyanates are in particular aromatic di- and polyisocyanates, preferably toluene diisocyanate (TDI) and / or diphenylmethane diisocyanate (MDI).The building block and the monomer and typical converting step(s) to obtain the building block or monomer are described in more detail in paragraphs
[1000] to
[1012] of Reference RF1.The term “polymer A”, as used in the context of the product Q herein, comprises thermoplastic, e.g., polyamide or thermoplastic polyurethane, thermoset, e.g., polyurethane, elastomer, e.g., polybutadiene, or a copolymer or a mixture thereof and is defined in more detail in paragraphs
[2001] to
[2007] of Reference RF1.The term “polymer composition A”, as used in the context of the product Q herein, comprises all compositions comprising a polymer as described above and one or more additive(s), e.g. reinforcement, colorant, modifier and / or flame retardant, and is defined in more detail in paragraph
[2008] of Reference RF1.The term “polymer product A”, as used in the context of the product Q herein, comprises any product comprising the polymer A and / or polymer composition A as described above and is defined in more detail in paragraphs
[2009] and
[2010] of Reference RF1.The step(s) to obtain the polymer, preferably polymer A, polymer composition, preferably polymer composition A or polymer product, preferably polymer product A is / are described in more detail in paragraph
[2011] of Reference RF1.240190W001- 16 -The term “industrial use polymer”, as used in the context of the product Q herein, comprises rheology, polycarboxylate, alkoxylated polyalkylenamine, alkoxylated polyalkylenimine, poly- ether-based, dye inhibition and soil release cleaning polymers defined in more detail in paragraphs
[3035] to
[3044] of Reference RF1. The term “industrial use surfactant”, as used in the context of the product Q herein, comprises non-ionic, anionic and amphoteric industrial use surfactants defined in more detail in paragraphs
[3008] to
[3034] of Reference RF1. The term “industrial use descaling compound”, as used in the context of the product Q herein, comprises non-phosphate based builders (NPB) and phosphonates (CoP) described in more detail in paragraphs
[3001] to
[3005] of Reference RF1. The term “industrial use biocide”, as used in the context of the product Q herein, refers to a chemical compound that kills microorganisms or inhibits their growth or reproduction defined in more detail in paragraphs
[3006] to
[3007] of Reference RF1. The term “industrial use solvent”, as used in the context of the product Q herein, comprises alkyl amides, alkyl lactamides, alkyl esters, lactate esters, alkyl diester, cyclic alkyl diester, cyclic carbonates, aromatic aldehydes and aromatic esters defined in more detail in paragraphs
[3045] to
[3055] of Reference RF1. The term “industrial use dispersant”, as used in the context of the product Q herein, comprises anionic and non-ionic industrial use dispersants defined in more detail in paragraphs
[3056] to
[3058] of Reference RF1. The term “composition and / or formulation thereof” with reference to the industrial use polymers, industrial use surfactants, descaling compounds and / or industrial use biocides refers to industrial use compositions and / or institutional use products and / or fabric and home care products and / or personal care products defined in more detail in paragraph
[3059] of Reference RF1. The converting step(s) to obtain the industrial use polymer, industrial use surfactant, descaling compound and / or industrial use biocide are defined in more detail in paragraph
[3060] of Reference RF1. The converting steps to obtain the industrial use composition or formulation of the industrial use polymer, industrial use surfactant, descaling compound and / or industrial use biocide are defined in more detail in paragraph
[3061] of Reference RF1.The term “agrochemical composition”, as used in the context of the product Q herein, typically relates to a composition comprising an agrochemically active ingredient and at least one agrochemical formulation auxiliary. Examples of agrochemical compositions, active ingredients and auxiliaries are described in more detail in Reference RF1 , paragraph
[4001] ,The agrochemical composition may take the form of any customary formulation. The agrochemical compositions are prepared in a known manner, e.g. described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. The converting step(s) to obtain the agrochemically active ingredients and auxiliaries may be conducted240190W001- 17 - in analogy to the production step(s) of their analogues that are based on petrochemicals or other precursors that are not gained by recycling processes. In addition, conversion to compounds mentioned in sections “Polymer” and “Cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter, further cosmetic ingredient or compositions or formulations thereof” may be performed as described in these sections as well as the respective paragraphs in Reference RF1.The term active pharmaceutical ingredients and / or intermediates thereof, as used in the context of the product Q herein, comprises substances that provide pharmacological activity or other direct effect in the diagnosis, cure, mitigation, treatment, or prevention of disease, or to affect the structure or any function of the body. Intermediates thereof are isolated products that are generated during a multi-step route of synthesis of an active pharmaceutical ingredient. The term pharmaceutical excipients, as used in the context of the product Q herein, comprises compounds or compound mixtures used in compositions for various pharmaceutical applications, which are not substantially pharmaceutically active on itself. Active pharmaceutical ingredients and / or intermediates thereof and pharmaceutical excipients are defined in more detail in paragraph
[5001] of Reference RF1.The converting step(s) to obtain the active pharmaceutical ingredients and / or intermediates thereof and pharmaceutical excipients may comprise one or more synthesis steps and can be performed by conventional synthesis and techniques well known to a person skilled in the art.The terms animal feed additives, human food additives, dietary supplements, as used in the context of the product Q herein, comprises Vitamins, Pro-Vitamins and active metabolites thereof including intermediates and precursors, especially Vitamin A, B, E, D, K and esters thereof, like acetate, propionate, palmitate esters or alcohols thereof like retinol or salts thereof and any combinations thereof; Tetraterpenes, especially isoprenoids like carotenoids and xanthophylls including their intermediates and precursors as well as mixtures and derivates thereof, especially beta carotene, Canthaxanthin, Citranaxanthin, Astaxanthin, Zeaxanthin, Lutein, Lycopene, Apo-carotenoids, and any combinations thereof; organic acids, especially formic acid, propionic acid and salts thereof, such as sodium, calcium or ammonium salts, and any combinations thereof, such as but not limited to mixtures of formic acid and sodium formiate, propionic acid and ammonium propionate, formic acid and propionic acid, formic acid and sodium formiate and propionic acid, propionic acid and sodium propionate and formic acid and sodium formiate; glycerides of carboxylic acids and short and medium chain fatty acids, conjugated linoleic acids, such as omega-6 fatty acid (C18:2) methyl ester and 1 ,2-propandiol and beverage stabilizers, such as polyvinylpyrrolidone-polymer or polyvinylimidazole / polyvinylpyrrolidone-co- polymer. Animal feed additives, human food additives and dietary supplements are defined in more detail in paragraph
[5002] of Reference RF1.240190W001- 18 -The converting step(s) to obtain the animal feed additives, human food additives, dietary supplements may comprise one or more synthesis steps and can be performed by conventional synthesis and techniques well known to a person skilled in the art.The terms aroma chemical and aroma composition as used in the context of the product Q herein, comprise a volatile organic substance with a molecular weight between 70-250 g / mol comprising a functional group with a carbon skeleton of C5-C16 carbon atoms comprising linear, branched, cyclic, for example with a ring size of C5-C18, bicyclic or tricyclic aliphatic chains and but not necessarily one or more unsaturated structural elements like double bonds, triple bonds, aromatics or heteroaromatics and preferably the one or more additional functional groups are selected from alcohol, ether, ester, ketone, aldehyde, acetal, carboxylic acid, nitrile, thiol, amine. In one aspect, the aroma chemical is a terpene-based aroma chemical, for example selected from monoterpenes and monoterpenoids, sesquiterpenes and sesquiterpenoids, diterpenes, triterpenes or tetraterpenes. Aroma chemicals can be combined with further aroma chemicals to give an aroma composition. Aroma chemicals and aroma compositions are defined in more detail in paragraph
[5003] of Reference RF1.The converting step(s) to obtain the aroma chemical and aroma composition may comprise one or more synthesis steps and can be performed by conventional synthesis and techniques well known to a person skilled in the art.The term “aqueous polymer dispersion”, as used in the context of the product Q herein, comprises aqueous composition(s) comprising dispersed polymer(s) and is defined in more detail in the section
[6001] entitled “aqueous polymer dispersion” of Reference RF1. The dispersed polymers) may be selected from acrylic emulsion polymer(s), styrene acrylic emulsion polymer(s), styrene butadiene dispersion(s), aqueous dispersion(s) comprising composite particles, acrylate alkyd hybrid dispersion(s), polyurethane(s) (including UV-curable polyurethanes) and polyurethane - poly(meth)acrylate hybrid polymer(s). The term “emulsion polymer”, as used in the context of the product Q herein, comprises polymer(s) made by free-radical emulsion polymerization. Aqueous polyurethane dispersion(s) are defined in more detail in the section
[6002] entitled “Polyurethane dispersions” of Reference RF1. UV-curable polyurethane(s) is / are defined in more detail in the section
[6017] of Reference RF1. Polyurethane - poly(meth)acrylate hybrid polymer(s) is / are defined in more detail in the section
[6016] of Reference RF1.The term “polymeric dispersant”, as used in the context of the product Q herein, comprises preferably polymer(s) comprising polyether side chain, in particular polycarboxylate ether polymer(s) and polycondensation product(s) defined in more detail in paragraph
[6020] entitled “Polymeric dispersant” of Reference RF1.240190W001- 19 -The converting (polymerization) step(s) to obtain the aqueous polymer dispersion(s) comprising emulsion polymer(s) is / are defined in more detail in the section
[6003] entitled “Emulsion polymerization” of Reference RF1.The converting (polymerization) step(s) to obtain the aqueous polyurethane dispersion(s) is / are defined in more detail in the section
[6014] entitled “Process for the preparation of aqueous polyurethane dispersions” and section [6017)] entitled “Aqueous UV-curable polyurethane dispersions, their preparation and use and compositions containing them” of Reference RF1. Composition(s) and uses of aqueous polymer dispersion(s) and of polymeric dispersant(s) are defined in more detail in the following sections of Reference RF1 : section
[6004] entitled “Uses of aqueous polymer dispersions”, section
[6005] entitled “Binders for architectural and construction coatings” section
[6006] entitled “Binders for paper coating” section
[6007] entitled “Binders for fiber bonding” section
[6008] entitled “Adhesive polymers and adhesive compositions” section
[6015] entitled “Aqueous polyurethane dispersions suitable for use in coating compositions” section
[6016] entitled “Aqueous polyurethane - poly(meth)acrylate hybride polymer dispersions suitable for use in coating compositions” section
[6017] entitled “Aqueous UV-curable polyurethane dispersions, their preparation and use and compositions containing them” section
[6018] entitled “Inorganic binder compositions comprising polymeric dispersants and their use”
[6019] 100% curable coating compositionsUV-crosslinkable poly(meth)acrylate(s) and its / their uses are defined in more detail in section
[6009] entitled “UV-crosslinkable poly(meth)acrylates for use in UV-curable solvent-free hotmelt adhesives and their use for making pressure-sensitive self-adhesive articles” of Reference RF1.Polyisocyanate(s), composition(s) comprising them and their uses are defined in more detail in section
[6010] entitled “Polyisocyanates” of Reference RF1.Hyperbranched polyester polyol(s) and its / their uses are defined in more detail in section
[6011] entitled “Organic solvent based hyperbranched polyester polyols suitable for use in coating compositions” of Reference RF1. The converting step(s) to obtain the hyperbranched polyester polyols is / are defined in more detail in the section
[6012] entitled “Preparation of organic solvent based hyperbranched polyester polyols” of Reference RF1. Coating composition(s) comprising hyperbranched polyester polyol(s), polyisocyanate(s) and additive(s) and substrate(s) coated240190W001- 20 - therewith are defined in more detail in section
[6013] entitled “Organic solvent based two component coating compositions comprising hyperbranched polyester polyols and polyisocyanates’ of Reference RF1.Unsaturated polyester polyol(s), solvent-based coating composition(s) comprising said unsaturated polyester polyol(s) and substrate(s) for coating with said coating composition(s) are defined in more detail in section
[6018] entitled “Organic solvent based coating composition comprising unsaturated polyester polyols” of Reference RF1. 100% curable coating composition(s) is / are defined in more detail in section
[6019] of Reference RF1.Polymeric dispersant(s) for inorganic binder compositions is / are defined in more detail in section
[6020] of Reference RF1. The inorganic binder composition(s) comprising the polymeric dispersants and their use are defined in more detail in section
[6021] of Reference RF1. The converting step(s) to obtain the polymeric dispersant(s) are defined in more detail in section
[6020] of Reference RF1. The term “inorganic binder composition” comprising the polymeric dispersants), as used in the context of the product Q herein, comprises preferably in particular hydraulically setting compositions and compositions comprising calcium sulfate and is defined in more detail in section
[6021] of Reference RF1 entitled “Inorganic binder compositions comprising the polymeric dispersant and their use”. Specific building material formulation(s) comprising polymeric dispersant(s) or building product(s) produced by a building material formulation comprising a polymeric dispersant are disclosed in more detail in section
[6021] of Reference RF1.The term “cosmetic surfactant”, as used in the context of the product Q herein, comprises nonionic, anionic, cationic and amphoteric surfactants and is defined in more detail in paragraph
[7002] of Reference RF1. The term “emollient”, as used in the context of the product Q herein, refers to a chemical compound used for protecting, moisturizing, and / or lubricating the skin and is defined in more detail in paragraph
[7003] of Reference RF1. The term “wax”, as used in the context of the product Q herein, comprises pearlizers and opacifiers and is defined in more detail in paragraph
[7004] of Reference RF1. The term “cosmetic polymer”, as used in the context of the product Q herein, comprises any polymer that can be used as an ingredient in a cosmetic formulation and is defined in more detail in paragraph
[7005] of Reference RF1. The term “UV filter”, as used in the context of the product Q herein, refers to a chemical compound that blocks or absorbs ultraviolet light and is defined in more detail in paragraph
[7006] of Reference RF1. The term “further cosmetic ingredient”, as used in the context of the product Q herein, comprises any ingredient suitable for making a cosmetic formulation. Several sources disclose cosmetically acceptable ingredients. E. g. the database Cosing on the internet pages of the European Commission discloses cosmetic ingredients and the International Cosmetic Ingredient Die-240190W001- 21 - tionary and Handbook, edited by the Personal Care Products Council (PCPC), discloses cosmetic ingredients. The term “composition and / or formulation thereof” with reference to the cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter and / or further cosmetic ingredient refers to personal care and / or cosmetic compositions or formulations defined in more detail in paragraph
[7007] of Reference RF1. The converting step(s) to obtain the cosmetic surfactant, emollient, wax, cosmetic polymer, UV filter or further cosmetic ingredient is / are defined in more detail in paragraph
[7008] of Reference RF1.The terms “polymer B”, “polymer composition B”, “coating composition”, “other functional composition”, “foil”, “molded body”, “coating” and “coated substrate” are well known to the person skilled in the art and are defined in more detail from paragraph
[8000] to
[8005] of Reference RF1.The unit bara relates to an absolute pressure and the unit barg to a relative pressure, wherein 1 bar equals 105Pa.The present invention is further illustrated by the following set of embodiments and combinations of embodiments resulting from the dependencies and back-references as indicated. In particular, it is noted that in each instance where a range of embodiments is mentioned, for example in the context of a term such as "The process of any one of embodiments 1 to 4", every embodiment in this range is meant to be explicitly disclosed for the skilled person, i.e. the wording of this term is to be understood by the skilled person as being synonymous to "The process of any one of embodiments 1 , 2, 3 and 4". Further, it is explicitly noted that the following set of embodiments represents a suitably structured part of the general description directed to preferred aspects of the present invention, and, thus, suitably supports, but does not represent the claims of the present invention.1 . A process for preparing one or more ethers, preferably two or more ethers, the process comprising(i) preparing a feed stream comprising an alcohol, an epoxide, and a catalyst;(ii) feeding the feed stream prepared in (i) into a reactor, and subjecting the feed stream to reaction conditions, obtaining a product stream comprising the one or more ethers, preferably the two or more ethers;(iii) feeding the product stream obtained from (ii) into a first fractionating column, and separating the product stream into a first overhead stream, wherein the first overhead stream is preferably gaseous, and a first bottoms stream, wherein the first bottoms stream is preferably liquid;240190W001- 22 -(iv) preparing a first H2O-containing stream, wherein the first H2O-containing stream is preferably liquid;(v) transferring heat from the first overhead stream obtained from (iii) to the first H2O- containing stream prepared in (iv), obtaining a heated first H2O-containing stream, wherein the heated first H2O-containing stream is preferably gaseous, and a liquid first overhead stream.2. The process of embodiment 1 , wherein the one or more ethers are selected from the group consisting of ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, propylene glycol monobutyl ether, dipropylene glycol monobutyl ether, tripropylene glycol monobutyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, triethylene glycol monohexyl ether, and mixtures of two or more thereof.3. The process of embodiment 1 or 2, wherein the one or more ethers comprise a monoether, wherein the monoether is preferably selected from the group consisting of ethylene glycol monobutyl ether, propylene glycol monobutyl ether, ethylene glycol monomethyl ether, ethylene glycol monohexyl ether, and mixtures of two or more thereof.4. The process of any one of embodiments 1 to 3, wherein the alcohol comprised in the feed stream prepared in (i) is selected from the group consisting of methanol, butanol, hexanol, and mixtures of two or more thereof.5. The process of any one of embodiments 1 to 4, wherein the epoxide comprised in the feed stream prepared in (i) is selected from the group consisting of propylene oxide, ethylene oxide, and mixtures of two or more thereof.6. The process of any one of embodiments 1 to 5, wherein the catalyst comprised in the feed stream prepared in (i) comprises one or more of a methanolate, a butanolate, a hexylglycolate, and mixtures of two or more thereof, wherein the catalyst preferably comprises, more preferably consists of, sodium methanolate, sodium butanolate, sodium hexylglycolate, and mixtures of two or more thereof.7. The process of any one of embodiments 1 to 6, wherein the reaction conditions according to (ii) comprise heating the feed stream to a temperature in the range of from 110 to 235 °C, preferably in the range of from 115 to 230 °C.240190W001- 23 -8. The process of any one of embodiments 1 to 7, wherein the reaction conditions comprise adiabatic conditions.9. The process of any one of embodiments 1 to 8, wherein the reactor comprises an inlet end and an outlet end.10. The process of embodiment 9, wherein the reaction conditions according to (ii) comprise a temperature at the inlet end in the range of from 110 to 185 °C, preferably of from 115 to 180 °C.11. The process of embodiment 9 or 10, wherein the reaction conditions according to (ii) comprise a temperature at the outlet end of the reactor in the range of from 180 to 235 °C, preferably of from 185 to 230 °C.12. The process of any one of embodiments 9 to 11 , wherein the reaction conditions according to (ii) comprise a pressure at the outlet end of the reactor in the range of from 10 to 40 bara, preferably in the range of from 15 to 35 bara, more preferably in the range of from 17 to 33 bara.13. The process of any one of embodiments 1 to 12, wherein the product stream obtained from (ii) is fed according to (iii) into the first fractionating column having a pressure in the range of from 400 to 1160 mbara, preferably in the range of from 425 to 1125 mbara, more preferably in the range of from 450 to 1100 mbara.14. The process of any one of embodiments 1 to 13, wherein the first overhead stream obtained from (iii) has a temperature in the range of from 71 to 174 °C, preferably in the range of from 100 to 169 °C, more preferably in the range of from 110 to 160 °C.15. The process of any one of embodiments 1 to 14, wherein the first overhead stream obtained from (iii) has a pressure in the range of from 400 to 1160 mbara, preferably in the range of from 425 to 1125 mbara, more preferably in the range of from 450 to 1100 mbara.16. The process of any one of embodiments 1 to 15, wherein the first H2O-containing stream prepared in (iv) has a temperature in the range of from 66 to 169 °C, preferably in the range of from 95 to 164 °C, more preferably in the range of from 105 to 155 °C.240190W001- 24 -17. The process of any one of embodiments 1 to 16, wherein a difference of the temperature of the first overhead stream obtained from (iii) and the temperature of the first H2O-con- taining stream prepared in (iv) is in the range of from 5 to 20 K, preferably of from 10 to 15 K.18. The process of any one of embodiments 1 to 17, wherein heat is transferred according to(v) with a heat exchanger.19. The process of any one of embodiments 1 to 18, wherein the liquid first overhead stream obtained from (v) has a temperature in the range of from 70 to 120 °C, preferably in the range of from 90 to 110 °C, more preferably in the range of from 100 to 105 °C.20. The process of any one of embodiments 1 to 19, further comprising(vi) feeding the first bottoms stream obtained from (iii) in a second fractionating column, and separating the first bottoms streams into a second overhead stream, wherein the second overhead stream is preferably gaseous, and a second bottoms stream, wherein the second bottoms stream is preferably liquid.21. The process of embodiment 20, wherein the first bottoms stream obtained from (iii) is fed according to (vi) into the second fractionating column having a temperature in the range of from 100 to 215 °C, preferably in the range of from 120 to 205 °C, more preferably in the range of from 140 to 195 °C.22. The process of embodiment 20 or 21 , wherein the second overhead stream obtained from(vi) has a temperature in the range of from 85 to 145 °C, preferably in the range of from 90 to 140 °C, more preferably in the range of from 95 to 135 °C.23. The process of any one of embodiments 20 to 22, wherein the second overhead stream obtained from (vi) has a pressure in the range of from 25 to 350 mbara, preferably in the range of from 50 to 250 mbara, more preferably in the range of from 75 to 160 mbara.24. The process of any one of embodiments 20 to 23, further comprising(vii) preparing a second H2O-containing stream, wherein the second H2O-containing stream is preferably liquid,(viii) transferring heat from the second overhead stream obtained from (vi) to the second H2O-containing stream prepared in (vii), obtaining a heated second H2O-containing stream, wherein the heated second H2O-containing stream is preferably gaseous, and a liquid second overhead stream.240190W001- 25 -25. The process of embodiment 24, wherein the second H2O-containing stream prepared in(vii) has a temperature in the range of from 80 to 140 °C, preferably in the range of from 85 to 135 °C, more preferably in the range of from 90 to 130 °C.26. The process of embodiment 24 or 25, wherein a difference of the temperature of the second overhead stream obtained from (vi) and the temperature of the second H2O-contain- ing stream prepared in (vii) is in the range of from 5 to 20 K, preferably of from 10 to 15 K.27. The process of any one of embodiments 24 to 26, wherein heat is transferred according to(viii) with a heat exchanger.28. The process of any one of embodiments 1 to 27, wherein the heated first H2O-containing stream obtained from (v) and the heated second H2O-containing stream obtained from (viii) independently from one another have a temperature in the range of from 66 to 169 °C, preferably in the range of from 85 to 164 °C, more preferably in the range of from 90 to 155 °C.29. The process of any one of embodiments 1 to 28, wherein the heated first H2O-containing stream obtained from (v) is gaseous, and wherein the process further comprises(ix) compressing the gaseous first H2O-containing stream obtained from (v), wherein the gaseous first H2O-containing stream obtained from (v) is preferably compressed to a pressure in the range of from 2.6 to 7.1 bara, preferably in the range of from 2.7 to 6.6 bara, more preferably in the range of from 3.0 to 5.0 bara, more preferably in the range of from 3.5 to 4.5 bara.30. The process of any one of embodiments 1 to 29, wherein the heated second H2O-contain- ing stream obtained from (viii) is gaseous, and wherein the process further comprises(x) compressing the gaseous second H2O-containing stream obtained from (viii), wherein the gaseous second H2O-containing stream obtained from (viii) is preferably compressed to a pressure in the range of from 2.6 to 7.1 bara, preferably in the range of from 2.7 to 6.6 bara, more preferably in the range of from 3.0 to 5.0 bara, more preferably in the range of from 3.5 to 4.5 bara.31. The process of any one of embodiments 1 to 30, further comprising(xi) using the heated first H2O-containing stream obtained from (v) and the heated second H2O-containing stream obtained from (viii) independently from one another as direct or indirect heat source for a chemical process,240190W001- 26 - wherein the chemical process is preferably not for preparing one or more ethers, wherein the chemical process more preferably comprises preparing one or more of styrene and n-butylacrylate.32. The process of embodiment 38, wherein using the heated first H2O-containing stream obtained from (v) and the heated second H2O-containing stream obtained from (viii) as direct heat source for a chemical process independently from one another comprises transferring heat from the heated first H2O-containing stream obtained from (v) and / or from the heated second H2O-containing stream obtained from (viii) to a process stream used in the chemical process.33. The process of embodiment 31 or 32, wherein using the heated first H2O-containing stream obtained from (v) and the heated second H2O-containing stream obtained from (viii) as indirect heat source for a chemical process independently from one another comprises transferring heat from the heated first H2O-containing stream obtained from (v) and / or from the heated second H2O-containing stream obtained from (viii) to a stream comprising a heat transfer medium and transferring heat from the stream comprising a heat transfer medium to a process stream used in the chemical process.34. The process of any one of embodiments 1 to 33, wherein the heated H2O-containing stream obtained from (v) is not recycled into the process according to embodiment 1 , wherein the heated H2O-containing stream obtained from (v) is preferably not recycled into a process for preparing one or more ethers.35. The process of any one of embodiments 1 to 34, wherein the alcohol comprised in the feed stream prepared in (i) is butanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is butanolate, wherein the one or more ethers preferably comprise, more preferably consist of, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, and triethylene glycol monobutyl ether.36. The process of embodiment 35, wherein the first overhead stream obtained from (iii) comprises a portion of the alcohol, and wherein the first bottoms stream obtained from (iii) comprises a portion of the one or more ethers.37. The process of embodiment 35 or 36, wherein the first overhead stream obtained from (iii) has a temperature in the range of from 110 to 160 °C, preferably in the range of from 115 to 155 °C, more preferably in the range of from 120 to 145 °C.240190W001- 27 -38. The process of any one of embodiments 35 to 37, wherein the first overhead stream obtained from (iii) has a pressure in the range of from 30 to 85 mbara, preferably in the range of from 35 to 80 mbara, more preferably in the range of from 40 to 75 mbara.39. The process of any one of embodiments 35 to 38, wherein the second overhead stream obtained from (vi) comprises a first portion of the one or more ethers, wherein the second overhead stream obtained from (vi) preferably comprises ethylene glycol monobutyl ether, and wherein the second bottoms stream obtained from (vi) comprises a second portion of the one or more ethers, wherein the second bottoms stream obtained from (vi) preferably comprises one or more of diethylene glycol monobutyl ether and triethylene glycol monobutyl ether.40. The process of any one of embodiments 1 to 34, wherein the alcohol comprised in the feed stream prepared in (i) is butanol, the epoxide comprised in the feed stream prepared in (i) is propylene oxide, and the catalyst comprised in the feed stream prepared in (i) is butanolate, wherein the one or more ethers preferably comprise, more preferably consist of, propylene glycol monobutyl ether, dipropylene glycol monobutyl ether, and tripropylene glycol monobutyl ether.41. The process of embodiment 40, wherein the first overhead stream obtained from (iii) comprises a portion of the alcohol, and wherein the first bottoms stream obtained from (iii) comprises a portion of the one or more ethers.42. The process of embodiment 40 or 41 , wherein the first overhead stream obtained from (iii) has a temperature in the range of from 110 to 145 °C, preferably in the range of from 115 to 140 °C, more preferably in the range of from 120 to 135 °C.43. The process of any one of embodiments 40 to 42, wherein the first overhead stream obtained from (iii) has a pressure in the range of from 45 to 90 mbara, preferably in the range of from 50 to 85 mbara, more preferably in the range of from 55 to 80 mbara.44. The process of any one of embodiments 40 to 43, wherein the second overhead stream obtained from (vi) comprises a first portion of the one or more ethers, wherein the second overhead stream obtained from (vi) preferably comprises propylene glycol monobutyl ether, and wherein the second bottoms stream obtained from (vi) comprises a second por-240190W001- 28 - tion of the one or more ethers, wherein the second bottoms stream obtained from (vi) preferably comprises one or more of dipropylene glycol monobutyl ether and tripropylene glycol monobutyl ether.45. The process of any one of embodiments 1 to 34, wherein the alcohol comprised in the feed stream prepared in (i) is methanol, the epoxide comprised in the feed stream prepared in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is methanolate, wherein the one or more ethers preferably comprise, more preferably consist of, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, and triethylene glycol monomethyl ether.46. The process of embodiment 45, wherein the first overhead stream obtained from (iii) comprises a first portion of the one or more ethers, wherein the first overhead stream obtained from (iii) preferably comprises ethylene glycol monomethyl ether, and wherein the first bottoms stream obtained from (iii) comprises a second portion of the one or more ethers, wherein the first bottoms stream obtained from (iii) preferably comprises one or more of diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, and tetraethylene glycol monomethyl ether.47. The process of embodiment 45 or 46, wherein the first overhead stream obtained from (iii) has a temperature in the range of from 110 to 155 °C, preferably in the range of from 115 to 150 °C, more preferably in the range of from 120 to 145 °C.48. The process of any one of embodiments 45 to 47, wherein the first overhead stream obtained from (iii) has a pressure in the range of from 0.35 to 0.95 bara, preferably in the range of from 0.40 to 0.90 bara, more preferably in the range of from 0.45 to 0.85 bara.49. The process of any one of embodiments 45 to 48, wherein the second overhead stream obtained from (vi) comprises a first portion of the one or more ethers, wherein the second overhead stream obtained from (vi) preferably comprises ethylene glycol monomethyl ether, and wherein the second bottoms stream obtained from (vi) comprises a second portion of the one or more ethers, wherein the second bottoms stream obtained from (vi) preferably comprises one or more of ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, and tetraethylene glycol monomethyl ether.50. The process of any one of embodiments 1 to 34, wherein the alcohol comprised in the feed stream prepared in (i) is hexanol, the epoxide comprised in the feed stream prepared240190W001- 29 - in (i) is ethylene oxide, and the catalyst comprised in the feed stream prepared in (i) is hexanolate, wherein the one or more ethers preferably comprise, more preferably consist of, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, and triethylene glycol monohexyl ether.51. The process of embodiment 50, wherein the first overhead stream obtained from (iii) comprises a portion of the alcohol, and wherein the first bottoms stream obtained from (iii) comprises a portion of the one or more ethers.52. The process of embodiment 50 or 51 , wherein the first overhead stream obtained from (iii) has a temperature in the range of from 140 to 175 °C, preferably in the range of from 145 to 170 °C, more preferably in the range of from 150 to 165 °C.53. The process of any one of embodiments 50 to 52, wherein the first overhead stream obtained from (iii) has a pressure in the range of from 930 to 1250 mbara, preferably in the range of from 955 to 1225 mbara, more preferably in the range of from 980 to 1200 mbara.54. The process of any one of embodiments 50 to 53, wherein the second overhead stream obtained from (vi) comprises a portion of the alcohol, and wherein the second bottoms stream obtained from (vi) comprises a second portion of the one or more ethers, wherein the second bottoms stream obtained from (vi) preferably comprises one or more of ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, and triethylene glycol monohexyl ether.55. The process of any one of embodiments 1 to 54, further comprising(xii) recycling at least a portion of the liquid first overhead stream obtained from (v) into the feed stream according to (i).56. The process of any one of embodiments 1 to 55, wherein the process is a continuous process.57. A process, preferably according to any one of embodiments 1 to 56, comprising a step of converting the one or more ethers obtainable or obtained by the process according to any one of embodiments 1 to 56 to obtain a product Q.240190W001- 30 -The present invention is further illustrated by the following examples, comparative examples and reference examples.EXPERIMENTAL SECTIONExample 1A feed stream was prepared comprising methanol, ethylene oxide, and sodium methanolate. The feed stream was fed into a reactor, wherein the feed stream was reacted at a temperature of 120 °C and a pressure of 28 bara. A product stream was obtained from the reactor. The product stream comprised one or more of ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, and triethylene glycol monomethyl ether.The product stream was then fed into a first fractionating column for separating the product stream into a first overhead stream and a first bottoms stream. The first overhead stream particularly comprised ethylene glycol monomethyl ether. The first overhead stream had a temperature of 138 °C and a pressure of 0.46 bara. The first bottoms stream particularly comprised diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, and tetraethylene glycol monomethyl ether.A liquid first H2O-containing stream was prepared. Heat was transferred from the first overhead stream on the liquid first H2O-containing stream with a heat exchanger, particularly obtaining a liquid heated first H2O-containing stream having a temperature of 100 °C. The amount of energy transferred was about 6.7 MW. Then, the liquid heated first H2O-containing stream was flashed, particularly obtaining a gaseous H2O-containing stream having a pressure of 0.2 bara and a liquid H2O-containing stream having equilibrium temperature at said pressure of 0.2 bara, being about 60.0 °C. The obtained liquid H2O-containing stream was recycled into the liquid first cocontaining stream. The amount of water vapor obtained thereby can be calculated from the enthalpy of vaporization.Further, the first bottoms stream was fed in a second fractionating column for separating the first bottoms stream into a second overhead stream and a second bottoms stream. The second overhead stream particularly comprised ethylene glycol monomethyl ether. The second overhead stream had a temperature of 120 °C and a pressure of 0.09 bara. The second bottoms stream particularly comprised ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, and tetraethylene glycol monomethyl ether.240190W001- 31 -A liquid second W-containing stream was prepared. Heat was transferred from the second overhead stream on the liquid second H2O-containing stream with a falling film evaporator, particularly obtaining a gaseous H2O-containing stream having a temperature of 110 °C and a pressure of 1 .43 bara. The amount of energy transferred was about 1 MW. The amount of water va- por obtained thereby can be calculated from the enthalpy of vaporization.CITED LITERATURE- CN 1044472 C - US 3935279 A
Claims
240190W001- 32 -Claims1. A process for preparing one or more ethers, the process comprising(i) preparing a feed stream comprising an alcohol, an epoxide, and a catalyst;(ii) feeding the feed stream prepared in (i) into a reactor, and subjecting the feed stream to reaction conditions, obtaining a product stream comprising the one or more ethers;(iii) feeding the product stream obtained from (ii) into a first fractionating column, and separating the product stream into a first overhead stream and a first bottoms stream;(iv) preparing a first H2O-containing stream;(v) transferring heat from the first overhead stream obtained from (iii) to the first H2O- containing stream prepared in (iv), obtaining a heated first H2O-containing stream and a liquid first overhead stream.
2. The process of claim 1, wherein the one or more ethers are selected from the group consisting of ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, propylene glycol monobutyl ether, dipropylene glycol monobutyl ether, tripropylene glycol monobutyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, triethylene glycol monohexyl ether, and mixtures of two or more thereof.
3. The process of claim 1 or 2, wherein the alcohol comprised in the feed stream prepared in (i) is selected from the group consisting of methanol, butanol, hexanol, and mixtures of two or more thereof.
4. The process of any one of claims 1 to 3, wherein the epoxide comprised in the feed stream prepared in (i) is selected from the group consisting of propylene oxide, ethylene oxide, and mixtures of two or more thereof.
5. The process of any one of claims 1 to 4, wherein the catalyst comprised in the feed stream prepared in (i) comprises one or more of a methanolate, a butanolate, a hexylglycolate, and mixtures of two or more thereof.
6. The process of any one of claims 1 to 5, wherein the first overhead stream obtained from (iii) has a temperature in the range of from 71 to 174 °C.240190W001- 33 -7. The process of any one of claims 1 to 6, wherein the first overhead stream obtained from (iii) has a pressure in the range of from 400 to 1160 mbara.
8. The process of any one of claims 1 to 7, wherein the first H2O-containing stream prepared in (iv) has a temperature in the range of from 66 to 169 °C.
9. The process of any one of claims 1 to 8, wherein a difference of the temperature of the first overhead stream obtained from (iii) and the temperature of the first H2O-containing stream prepared in (iv) is in the range of from 5 to 20 K.
10. The process of any one of claims 1 to 9, further comprising(vi) feeding the first bottoms stream obtained from (iii) in a second fractionating column, and separating the first bottoms streams into a second overhead stream and a second bottoms stream.
11. The process of claim 10, wherein the second overhead stream obtained from (vi) has a temperature in the range of from 85 to 145 °C.
12. The process of any one of claims 10 or 11 , wherein the second overhead stream obtained from (vi) has a pressure in the range of from 25 to 350 mbara.
13. The process of any one of claims 10 to 12, further comprising(vii) preparing a second H2O-containing stream,(viii) transferring heat from the second overhead stream obtained from (vi) to the second H2O-containing stream prepared in (vii), obtaining a heated second H2O-containing stream and a liquid second overhead stream.
14. The process of claim 13, wherein a difference of the temperature of the second overhead stream obtained from (vi) and the temperature of the second H2O-containing stream prepared in (vii) is in the range of from 5 to 20 K.
15. A process comprising a step of converting the one or more ethers obtainable or obtained by the process according to any one of claims 1 to 14 to obtain a product Q.
Citation Information
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