公开(公告)号：US07728156B2

公开(公告)日：2010-06-01

申请号：US11342146

申请日：2006-01-26

申请人： Jianli Hu ,  Johnathan E. Holladay ,  Xinjie Zhang ,  Yong Wang

发明人： Jianli Hu ,  Johnathan E. Holladay ,  Xinjie Zhang ,  Yong Wang

IPC分类号： C07C29/00 ,  C07D315/00 ,  C07D493/00 ,  C07H1/00 ,  C07H17/00 ,  C07H5/04 ,  C07H1/06 ,  C13K5/00

CPC分类号： C07H1/00

摘要： The invention includes a method of treating a solid acid catalyst. After exposing the catalyst to a mixture containing a sugar alcohol, the catalyst is washed with an organic solvent and is then exposed to a second reaction mixture. The invention includes a process for production of anhydrosugar alcohol. A solid acid catalyst is provided to convert sugar alcohol in a first sample to an anhydrosugar alcohol. The catalyst is then washed with an organic solvent and is subsequently utilized to expose a second sample. The invention includes a method for selective production of an anhydrosugar. A solid acid catalyst is provided within a reactor and anhydrosugar alcohol is formed by flowing a starting sugar alcohol into the reactor. The acid catalyst is then exposed to an organic solvent which allows a greater amount of additional anhydrosugar to be produced than would occur without exposing the acid catalyst to the organic solvent.

摘要翻译： 本发明包括一种处理固体酸催化剂的方法。 在将催化剂暴露于含有糖醇的混合物之后，用有机溶剂洗涤催化剂，然后暴露于第二反应混合物。 本发明包括生产脱水葡萄糖醇的方法。 提供固体酸催化剂以将第一样品中的糖醇转化为脱水葡萄糖醇。 然后将催化剂用有机溶剂洗涤，随后用于暴露第二个样品。 本发明包括选择性生产脱水糖的方法。 在反应器内提供固体酸催化剂，通过将起始糖醇流入反应器而形成脱水葡萄糖醇。 然后将酸催化剂暴露于有机溶剂，其允许比不会将酸催化剂暴露于有机溶剂而产生更多量的额外的脱水糖。

公开(公告)号：US07649099B2

公开(公告)日：2010-01-19

申请号：US11341961

申请日：2006-01-26

申请人： Johnathan E. Holladay ,  Jianli Hu ,  Yong Wang ,  Todd A. Werpy ,  Xinjie Zhang

发明人： Johnathan E. Holladay ,  Jianli Hu ,  Yong Wang ,  Todd A. Werpy ,  Xinjie Zhang

IPC分类号： C07C29/00 ,  C07D315/00 ,  C07D493/00 ,  C07H1/00 ,  C07H17/00 ,  C07H5/04 ,  C07H1/06 ,  C13K5/00

CPC分类号： C07D307/20 ,  C07D493/04 ,  Y02P20/127

摘要： The invention includes methods of producing dianhydrosugars. A polyol is reacted in the presence of a first catalyst to form a monocyclic sugar. The monocyclic sugar is transferred to a second reactor where it is converted to a dianhydrosugar alcohol in the presence of a second catalyst. The invention includes a process of forming isosorbide. An initial reaction is conducted at a first temperature in the presence of a solid acid catalyst. The initial reaction involves reacting sorbitol to produce 1,4-sorbitan, 3,6-sorbitan, 2,5-mannitan and 2,5-iditan. Utilizing a second temperature, the 1,4-sorbitan and 3,6-sorbitan are converted to isosorbide. The invention includes a method of purifying isosorbide from a mixture containing isosorbide and at least one additional component. A first distillation removes a first portion of the isosorbide from the mixture. A second distillation is then conducted at a higher temperature to remove a second portion of isosorbide from the mixture.

摘要翻译： 本发明包括生产二脱水甘油糖的方法。 多元醇在第一催化剂存在下反应形成单环糖。 将单环糖转移到第二反应器中，在第二反应器中，在第二催化剂的存在下将其转化为二脱水甘油醇。 本发明包括形成异山梨醇的方法。 在固体酸催化剂存在下，在第一温度下进行初始反应。 初始反应包括使山梨醇反应生成1,4-脱水山梨糖醇，3,6-脱水山梨糖醇，2,5-甘露聚糖和2,5-己烷。 利用第二温度，将1,4-脱水山梨醇和3,6-脱水山梨醇转化为异山梨醇。 本发明包括从含有异山梨醇和至少一种另外的组分的混合物中纯化异山梨醇的方法。 第一蒸馏从混合物中除去第一部分的异山梨醇。 然后在较高温度下进行第二次蒸馏以从混合物中除去第二部分的异山梨醇。

公开(公告)号：US07772412B2

公开(公告)日：2010-08-10

申请号：US11341968

申请日：2006-01-26

申请人： Johnathan E. Holladay ,  Jianli Hu ,  Xinjie Zhang ,  Yong Wang

发明人： Johnathan E. Holladay ,  Jianli Hu ,  Xinjie Zhang ,  Yong Wang

IPC分类号： A61K31/34 ,  C07D493/04

CPC分类号： C07D493/04

摘要： The invention includes a method of dehydration of a sugar using a dehydration catalyst and a co-catalyst within a reactor. A sugar is introduced and H2 is flowed through the reactor at a pressure of less than or equal to about 300 psig to convert at least some of the sugar into an anhydrosugar product. The invention includes a process for producing isosorbide. A starting material comprising sorbitol is flowed into a reactor. H2 is counter flowed through the reactor. The starting material is exposed to a catalyst in the presence of a co-catalyst which comprises at least one metal. The exposing is conducted at a hydrogen pressure of less than or equal to 300 psig within the reactor and the hydrogen removes at least some of any water present during the exposing and inhibits formation of colored byproducts.

摘要翻译： 本发明包括使用反应器内的脱水催化剂和助催化剂使糖脱水的方法。 引入糖并且H2以小于或等于约300psig的压力流过反应器，以将至少一些糖转化为脱水糖产品。 本发明包括制备异山梨醇的方法。 将含有山梨醇的原料流入反应器。 H2反向流过反应器。 在包含至少一种金属的助催化剂的存在下，将原料暴露于催化剂。 暴露在反应器内在小于或等于300psig的氢气压力下进行，并且氢去除暴露期间存在的任何水中的至少一些，并且抑制着色副产物的形成。

公开(公告)号：US07615652B2

公开(公告)日：2009-11-10

申请号：US11341930

申请日：2006-01-26

申请人： Johnathan E. Holladay ,  Jianli Hu ,  Yong Wang ,  Todd A. Werpy

发明人： Johnathan E. Holladay ,  Jianli Hu ,  Yong Wang ,  Todd A. Werpy

IPC分类号： C07C29/00 ,  C07D315/00 ,  C07D493/00 ,  C07H1/00 ,  C07H17/00 ,  C07H5/04 ,  C07H1/06 ,  C13K5/00

CPC分类号： C07D493/04

摘要： The invention includes methods for producing dianhydrosugar alcohol by providing an acid catalyst within a reactor and passing a starting material through the reactor at a first temperature. At least a portion of the staring material is converted to a monoanhydrosugar isomer during the passing through the column. The monoanhydrosugar is subjected to a second temperature which is greater than the first to produce a dianhydrosugar. The invention includes a method of producing isosorbide. An initial feed stream containing sorbitol is fed into a continuous reactor containing an acid catalyst at a temperature of less than 120° C. The residence time for the reactor is less than or equal to about 30 minutes. Sorbitol converted to 1,4-sorbitan in the continuous reactor is subsequently provided to a second reactor and is dehydrated at a temperature of at least 120° C. to produce isosorbide.

摘要翻译： 本发明包括通过在反应器内提供酸催化剂并使原料在第一温度下通过反应器来生产二脱水甘油的方法。 在通过色谱柱期间，至少一部分起始物质被转化为单一脱氢葡萄糖异构体。 单糖酐经受大于第一温度的第二温度以产生二脱水糖。 本发明包括一种生产异山梨醇的方法。 含有山梨醇的初始进料流在小于120℃的温度下进料到含有酸催化剂的连续反应器中。反应器的停留时间小于或等于约30分钟。 随后将连续反应器中转化为1,4-脱水山梨醇的山梨糖醇提供给第二反应器，并在至少120℃的温度下脱水以制备异山梨醇。

公开(公告)号：US20110263874A1

公开(公告)日：2011-10-27

申请号：US13175601

申请日：2011-07-01

申请人： Todd A. Werpy ,  John G. Frye, JR. ,  James F. White ,  Johnathan E. Holladay ,  Alan H. Zacher

发明人： Todd A. Werpy ,  John G. Frye, JR. ,  James F. White ,  Johnathan E. Holladay ,  Alan H. Zacher

IPC分类号： C07D207/404 ,  C07D207/267

CPC分类号： C07D207/404

摘要： The invention includes methods of processing an initial di-carbonyl compound by conversion to a cyclic compound. The cyclic compound is reacted with an alkylating agent to form a derivative having an alkylated ring nitrogen. The invention encompasses a method of producing an N-alkyl product. Ammonia content of a solution is adjusted to produce a ratio of ammonia to di-carboxylate compound of from about 1:1 to about 1.5:1. An alkylating agent is added and the initial compound is alkylated and cyclized. The invention includes methods of making N-methyl pyrrolidinone (NMP). Aqueous ammonia and succinate is introduced into a vessel and ammonia is adjusted to provide a ratio of ammonia to succinate of less than 2:1. A methylating agent is reacted with succinate at a temperature of from greater than 100° C. to about 400° C. to produce N-methyl succinimide which is purified and hydrogenated to form NMP.

摘要翻译： 本发明包括通过转化为环状化合物来处理初始二羰基化合物的方法。 环状化合物与烷基化剂反应形成具有烷基化环氮的衍生物。 本发明包括生产N-烷基产物的方法。 调节溶液的氨含量以产生约1：1至约1.5：1的氨与二羧酸酯化合物的比例。 加入烷基化剂并将该初始化合物烷基化并环化。 本发明包括制备N-甲基吡咯烷酮（NMP）的方法。 将氨水和琥珀酸钠引入容器中，并调节氨以提供小于2:1的氨与琥珀酸的比例。 甲基化剂与琥珀酸酯在大于100℃至约400℃的温度下反应，生成N-甲基琥珀酰亚胺，将其纯化并氢化形成NMP。

公开(公告)号：US07994347B2

公开(公告)日：2011-08-09

申请号：US11760634

申请日：2007-06-08

申请人： Michael A. Lilga ,  Richard T. Hallen ,  Todd A. Werpy ,  James F. White ,  Johnathan E. Holladay ,  John G. Frye, Jr. ,  Alan H. Zacher

发明人： Michael A. Lilga ,  Richard T. Hallen ,  Todd A. Werpy ,  James F. White ,  Johnathan E. Holladay ,  John G. Frye, Jr. ,  Alan H. Zacher

IPC分类号： C07D307/02

CPC分类号： C07D307/42 ,  C07D307/46

摘要： A method of reducing hydroxymethylfurfural (HMF) where a starting material containing HMF in a solvent comprising water is provided. H2 is provided into the reactor and the starting material is contacted with a catalyst containing at least one metal selected from Ni, Co, Cu, Pd, Pt, Ru, Ir, Re and Rh, at a temperature of less than or equal to 250° C. A method of hydrogenating HMF includes providing an aqueous solution containing HMF and fructose. H2 and a hydrogenation catalyst are provided. The HMF is selectively hydrogenated relative to the fructose at a temperature at or above 30° C. A method of producing tetrahydrofuran dimethanol (THFDM) includes providing a continuous flow reactor having first and second catalysts and providing a feed comprising HMF into the reactor. The feed is contacted with the first catalyst to produce furan dimethanol (FDM) which is contacted with the second catalyst to produce THFDM.

摘要翻译： 提供一种还原羟甲基糠醛（HMF）的方法，其中含有HMF的原料在包含水的溶剂中。 将H2置于反应器中，并使原料与含有至少一种选自Ni，Co，Cu，Pd，Pt，Ru，Ir，Re和Rh的金属的催化剂在小于或等于250的温度下接触 氢化HMF的方法包括提供含有HMF和果糖的水溶液。 H2和氢化催化剂。 在30℃或更高的温度下，HMF相对于果糖选择性地氢化。制备四氢呋喃二甲醇（THFDM）的方法包括提供具有第一和第二催化剂的连续流动反应器，并向反应器提供包含HMF的进料。 进料与第一催化剂接触以产生与第二催化剂接触以产生THFDM的呋喃二甲醇（FDM）。

公开(公告)号：US07687661B2

公开(公告)日：2010-03-30

申请号：US11377096

申请日：2006-03-15

申请人： Michael A. Lilga ,  James F. White ,  Johnathan E. Holladay ,  Alan H. Zacher ,  Danielle S. Muzatko ,  Rick J. Orth

发明人： Michael A. Lilga ,  James F. White ,  Johnathan E. Holladay ,  Alan H. Zacher ,  Danielle S. Muzatko ,  Rick J. Orth

IPC分类号： C07C67/30

CPC分类号： C07C51/377 ,  C07C51/41 ,  C07C57/04

摘要： A process is disclosed for conversion of salts of β-hydroxy carbonyl compounds forming useful conversion products including, e.g., α,β-unsaturated carbonyl compounds and/or salts of α,β-unsaturated carbonyl compounds. Conversion products find use, e.g., as feedstock and/or end-use chemicals.

摘要翻译： 公开了用于转化形成有用的转化产物（例如α，b' - 不饱和羰基化合物和/或α，β-不饱和羰基化合物的盐的α-羟基羰基化合物的盐的方法。 转化产物可用作例如原料和/或最终用途的化学品。

公开(公告)号：US20090054694A1

公开(公告)日：2009-02-26

申请号：US11895593

申请日：2007-08-24

申请人： Thomas H. Peterson ,  Johnathan E. Holladay ,  Alan H. Zacher ,  Michel J. Gray ,  Todd A. Werpy ,  James F. White

发明人： Thomas H. Peterson ,  Johnathan E. Holladay ,  Alan H. Zacher ,  Michel J. Gray ,  Todd A. Werpy ,  James F. White

IPC分类号： C07C45/29

CPC分类号： C07C45/52 ,  C07C49/17 ,  C07C47/22

摘要： Chemical production processes are provided that include exposing a reactant composition to a catalyst composition to form a product composition, with the reactant composition including a multihydric alcohol compound and the catalyst composition being effective to dehydrate at least a portion of the multihydric alcohol compound. Embodiments of the process provide that the reactant composition is exposed to the catalyst composition for less than about 0.25 seconds and/or that the catalyst is maintained at a temperature of from about 280° C. to about 320° C. Processes utilizing a reactant composition including a multihydric alcohol compound and an inert compound are also provided.

摘要翻译： 提供了化学生产方法，其包括将反应物组合物暴露于催化剂组合物以形成产物组合物，反应物组合物包含多元醇化合物，催化剂组合物有效地使至少一部分多元醇化合物脱水。 该方法的实施方案提供反应物组合物暴露于催化剂组合物少于约0.25秒和/或催化剂保持在约280℃至约320℃的温度。利用反应物组合物 还包括多元醇化合物和惰性化合物。

公开(公告)号：US07674916B2

公开(公告)日：2010-03-09

申请号：US11688022

申请日：2007-03-19

申请人： Todd A. Werpy ,  John G. Frey, Jr. ,  James F. White ,  Johnathan E. Holladay ,  Alan H. Zacher

发明人： Todd A. Werpy ,  John G. Frey, Jr. ,  James F. White ,  Johnathan E. Holladay ,  Alan H. Zacher

IPC分类号： C07D207/267 ,  C07D213/63

CPC分类号： C07D207/404

摘要： The invention includes methods of processing an initial di-carbonyl compound by conversion to a cyclic compound. The cyclic compound is reacted with an alkylating agent to form a derivative having an alkylated ring nitrogen. The invention encompasses a method of producing an N-alkyl product. Ammonia content of a solution is adjusted to produce a ratio of ammonia to di-carboxylate compound of from about 1:1 to about 1.5:1. An alkylating agent is added and the initial compound is alkylated and cyclized. The invention includes methods of making N-methyl pyrrolidinone (NMP). Aqueous ammonia and succinate is introduced into a vessel and ammonia is adjusted to provide a ratio of ammonia to succinate of less than 2:1. A methylating agent is reacted with succinate at a temperature of from greater than 100° C. to about 400° C. to produce N-methyl succinimide which is purified and hydrogenated to form NMP.

摘要翻译： 本发明包括通过转化为环状化合物来处理初始二羰基化合物的方法。 环状化合物与烷基化剂反应形成具有烷基化环氮的衍生物。 本发明包括生产N-烷基产物的方法。 调节溶液的氨含量以产生约1：1至约1.5：1的氨与二羧酸酯化合物的比例。 加入烷基化剂并将该初始化合物烷基化并环化。 本发明包括制备N-甲基吡咯烷酮（NMP）的方法。 将氨水和琥珀酸钠引入容器中，并调节氨以提供小于2:1的氨与琥珀酸的比例。 甲基化剂与琥珀酸酯在大于100℃至约400℃的温度下反应，生成N-甲基琥珀酰亚胺，将其纯化并氢化形成NMP。

公开(公告)号：US06992209B2

公开(公告)日：2006-01-31

申请号：US10315404

申请日：2002-12-09

申请人： Michael A. Lilga ,  Todd A. Werpy ,  Johnathan E. Holladay

发明人： Michael A. Lilga ,  Todd A. Werpy ,  Johnathan E. Holladay

IPC分类号： C07C69/66 ,  C07C67/30 ,  C07B35/00

CPC分类号： C07C67/08 ,  C07C51/377 ,  C07C67/327 ,  Y02P20/127 ,  Y02P20/582 ,  C07C57/04 ,  C07C69/67 ,  C07C69/003 ,  C07C69/14 ,  C07C69/54

摘要： The invention includes a method of forming an alpha, beta-unsaturated compound. A carboxylic acid is mixed with an alpha-hydroxy acid or an alpha-hydroxy ester and is esterified to form an alpha-acyloxy derivative. The alpha-acyloxy derivative is transformed into an alpha, beta-unsaturated derivative. The invention additionally includes a process of forming an acrylate. Lactic acid or a lactic acid ester is reacted with a first portion of acetic acid in the presence of a first catalyst to produce the corresponding 2-acetoxy propionic acid or ester. A non-reacted portion of the acetic acid is recycled. The 2-acetoxy propionic acid or ester is transferred to a second vessel containing a second catalyst, and acetic acid is liberated from the 2-acetoxy propionic acid or ester to produce a corresponding acrylic acid or acrylate ester. The acid or ester is subsequently esterified by reaction with an alcohol to form a desired acrylate ester.

摘要翻译： 本发明包括形成α，β-不饱和化合物的方法。 将羧酸与α-羟基酸或α-羟基酯混合并酯化形成α-酰氧基衍生物。 α-酰氧基衍生物转化成α，β-不饱和衍生物。 本发明还包括形成丙烯酸酯的方法。 乳酸或乳酸酯与第一部分乙酸在第一催化剂存在下反应，生成相应的2-乙酰氧基丙酸或酯。 将乙酸的未反应部分再循环。 将2-乙酰氧基丙酸或酯转移到含有第二催化剂的第二容器中，并从2-乙酰氧基丙酸或酯中释出乙酸，生成相应的丙烯酸或丙烯酸酯。 酸或酯随后通过与醇反应形成所需的丙烯酸酯而酯化。