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公开(公告)号：US20220204467A1
公开(公告)日：2022-06-30
申请号：US17599029
申请日：2021-05-03
发明人： Shawn Eady , Sabrina Conrad , Trenton Wilke , Christoph Krumm
IPC分类号： C07D307/64
摘要： Chemical compositions, and related methods for synthesizing furan, such as oleo-furan, surfactants, include calcium, magnesium, ammonium and/or lithium cations and one of a number of furan derivatives. Methods for synthesizing such furan surfactants containing calcium, magnesium, ammonium and/or lithium cations can include chemical reagents and purification procedures to prepare furan surfactants containing calcium, magnesium, ammonium and/or lithium cations. These furan surfactant compositions can be free of dioxane and ethoxylate.
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公开(公告)号：US10934266B2
公开(公告)日：2021-03-02
申请号：US16757447
申请日：2019-07-10
发明人： Shawn Eady , Connor Beach , Christoph Krumm
IPC分类号： C07D307/64
摘要： Compositions of furan based surfactants derived from unsaturated carbon-containing molecules, such as fatty acids, as well as methods for forming furan based surfactants from unsaturated carbon-containing molecules, such as fatty acids, are disclosed herein. These compositions and methods can utilize long-chain (e.g., C14-C26) unsaturated carbon-containing molecules, for instance unsaturated fatty acids such as oleic acid or methyl oleate from soybean oil, to derive oleo-furan surfactants. To facilitate this, certain such embodiments include reaction steps that cleave the reactant molecule (e.g., methyl oleate) at the double bond and subsequently oxidize products to form a carboxylic acid molecule and a dicarboxylic acid molecule. In such embodiments, these two acids can be subsequently acylated with furan and functionalized to form surfactants.
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公开(公告)号：US20240060006A1
公开(公告)日：2024-02-22
申请号：US18490418
申请日：2023-10-19
发明人： Shawn Eady , Tyler Robison , Michelle Cruz , Trenton Wilke , Sabrina Conrad , Maryam Ansari , Christoph Krumm
IPC分类号： C11D1/26
CPC分类号： C11D1/26
摘要： Disclosed herein are methods for sulfonation of oleo-furan compounds derived from a furan moiety and either an individual fatty acid or a mixture of fatty acids representative of those yielded from one or more plant oils. Additionally, this disclosure describes tuning sulfonation conditions to produce oleo-furan sulfonate blends which can demonstrate beneficial surfactant characteristics and improvements in various applications.
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公开(公告)号：US20210087124A1
公开(公告)日：2021-03-25
申请号：US16771250
申请日：2018-12-14
发明人： Christoph KRUMM , Connor BEACH , Shawn EADY
摘要： Devices, systems, and methods for forming furan based surfactants by reactive distillation are disclosed herein. Various embodiments can provide a consolidated reaction process that uses reactive distillation to synthesize oleo-furan surfactant molecules and intermediates by combining reaction and separation steps into a single reaction unit or a number of connected reaction units. The single reaction unit or a number of connected reaction units can include a catalyst bed and act to separate reaction side products at opposing ends of the unit or units.
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公开(公告)号：US20230183604A1
公开(公告)日：2023-06-15
申请号：US18060673
申请日：2022-12-01
发明人： Shawn Eady , Tyler Robison , Michelle Cruz , Trenton Wilke , Sabrina Conrad , Maryam Ansari , Christoph Krumm
IPC分类号： C11D1/26
CPC分类号： C11D1/26
摘要： Disclosed herein are methods for sulfonation of oleo-furan compounds derived from a furan moiety and either an individual fatty acid or a mixture of fatty acids representative of those yielded from one or more plant oils. Additionally, this disclosure describes tuning sulfonation conditions to produce oleo-furan sulfonate blends which can demonstrate beneficial surfactant characteristics and improvements in various applications.
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公开(公告)号：US11242305B2
公开(公告)日：2022-02-08
申请号：US16771250
申请日：2018-12-14
发明人： Christoph Krumm , Connor Beach , Shawn Eady
IPC分类号： C07C27/00 , C07D307/00 , B01D3/00 , C07C27/22 , B01D3/14 , B01D3/32 , C07C49/21 , C07D307/36
摘要： Devices, systems, and methods for forming furan based surfactants by reactive distillation are disclosed herein. Various embodiments can provide a consolidated reaction process that uses reactive distillation to synthesize oleo-furan surfactant molecules and intermediates by combining reaction and separation steps into a single reaction unit or a number of connected reaction units. The single reaction unit or a number of connected reaction units can include a catalyst bed and act to separate reaction side products at opposing ends of the unit or units.
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公开(公告)号：US20210188824A1
公开(公告)日：2021-06-24
申请号：US17124635
申请日：2020-12-17
发明人： Shawn Eady , Christoph Krumm
IPC分类号： C07D407/06 , C11D1/26
摘要： Methods for synthesizing oleo-furan surfactants from fatty aldehydes and compositions of furan based surfactants synthesized from such methods are disclosed. One method of forming a surfactant can include a hydroxyalkylation reaction of two methylfuran molecules with a fatty aldehyde molecule to form a di-furan product. This method can also include forming a surfactant from the di-furan product formed from the hydroxyalkylation. In particular, this di-furan product can be a surfactant precursor that is functionalized to form a surfactant.
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公开(公告)号：US11634399B2
公开(公告)日：2023-04-25
申请号：US17156803
申请日：2021-01-25
发明人： Shawn Eady , Connor Beach , Christoph Krumm
IPC分类号： C07D307/64
摘要： Compositions of furan based surfactants derived from unsaturated carbon-containing molecules, such as fatty acids, as well as methods for forming furan based surfactants from unsaturated carbon-containing molecules, such as fatty acids, are disclosed herein. These compositions and methods can utilize long-chain (e.g., C14-C26) unsaturated carbon-containing molecules, for instance unsaturated fatty acids such as oleic acid or methyl oleate from soybean oil, to derive oleo-furan surfactants. To facilitate this, certain such embodiments include reaction steps that cleave the reactant molecule (e.g., methyl oleate) at the double bond and subsequently oxidize products to form a carboxylic acid molecule and a dicarboxylic acid molecule. In such embodiments, these two acids can be subsequently acylated with furan and functionalized to form surfactants.
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公开(公告)号：US11492338B2
公开(公告)日：2022-11-08
申请号：US17599029
申请日：2021-05-03
发明人： Shawn Eady , Sabrina Conrad , Trenton Wilke , Christoph Krumm
IPC分类号： C07D307/64
摘要： Chemical compositions, and related methods for synthesizing furan, such as oleo-furan, surfactants, include calcium, magnesium, ammonium and/or lithium cations and one of a number of furan derivatives. Methods for synthesizing such furan surfactants containing calcium, magnesium, ammonium and/or lithium cations can include chemical reagents and purification procedures to prepare furan surfactants containing calcium, magnesium, ammonium and/or lithium cations. These furan surfactant compositions can be free of dioxane and ethoxylate.
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公开(公告)号：US11168076B2
公开(公告)日：2021-11-09
申请号：US17124635
申请日：2020-12-17
发明人： Shawn Eady , Christoph Krumm
IPC分类号： C07D407/06 , C11D1/26
摘要： Methods for synthesizing oleo-furan surfactants from fatty aldehydes and compositions of furan based surfactants synthesized from such methods are disclosed. One method of forming a surfactant can include a hydroxyalkylation reaction of two methylfuran molecules with a fatty aldehyde molecule to form a di-furan product. This method can also include forming a surfactant from the di-furan product formed from the hydroxyalkylation. In particular, this di-furan product can be a surfactant precursor that is functionalized to form a surfactant.
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