公开(公告)号：US06610863B2

公开(公告)日：2003-08-26

申请号：US10037126

申请日：2001-12-21

Applicant: Bhaskar Krishna Arumugam ,  Nick Allen Collins ,  Transito Lynne Macias ,  Steven Thomas Perri ,  Jeffrey Earl Grant Powell ,  Chester Wayne Sink ,  Michael Roy Cushman

Inventor： Bhaskar Krishna Arumugam ,  Nick Allen Collins ,  Transito Lynne Macias ,  Steven Thomas Perri ,  Jeffrey Earl Grant Powell ,  Chester Wayne Sink ,  Michael Roy Cushman

IPC: C07D30762

CPC classification number: C07D307/62 ,  Y02P20/582

Abstract: The present invention provides methods and an apparatus for the manufacture of an L-ascorbic acid product in high yield by direct conversion of an aqueous solution containing 2-keto-L-gulonic acid by contact with an acid catalyst or under thermal self-catalyzed conditions at a conversion level that maximizes the formation of L-ascorbic acid and minimizes decomposition of the L-ascorbic acid thus formed. The separation process for L-ascorbic acid and KLG is operated in such a way that an efficient separation process allows the majority of the KLG to be recycled for further conversion. The product stream from the separation process is then subjected to a recovery step to obtain crystalline L-ascorbic acid product.

公开(公告)号：US06864376B2

公开(公告)日：2005-03-08

申请号：US10036912

申请日：2001-12-21

Applicant: Steven Thomas Perri ,  Michael Roy Cushman ,  Jeffery Earl Grant Powell ,  Brendan William Boyd ,  Bhaskar Krishna Arumugam ,  Nick Allen Collins

Inventor： Steven Thomas Perri ,  Michael Roy Cushman ,  Jeffery Earl Grant Powell ,  Brendan William Boyd ,  Bhaskar Krishna Arumugam ,  Nick Allen Collins

IPC: C07B61/00 ,  C07D307/62

CPC classification number: C07D307/62 ,  Y02P20/582

Abstract: The present invention comprises the use of sulfite additives to reduce discoloration of L-ascorbic acid produced from acid or aqueous solutions of 2-keto-L-gulonic acid. In one aspect, the present invention comprises a continuous process for producing L-ascorbic acid from an aqueous solution of 2-keto-L-gulonic acid. The use of sulfite additives reduces product stream color and improves product recovery by binding to high molecular weight reaction by-products. In a continuous process, the reaction stream is separated from residual sulfite and sulfite-bound by-products to produce a product stream enriched in aqueous ascorbic acid for recovery, and an enriched 2-keto-L-gulonic acid stream which is recycled to the reactor. The in situ use of sulfite additives during the reaction increases the overall yield of L-ascorbic acid, with no loss in selectivity of the synthesis.

Abstract translation: 本发明包括使用亚硫酸盐添加剂来减少由2-酮-L-古洛糖酸的酸或水溶液产生的L-抗坏血酸的变色。 一方面，本发明包括从2-酮-L-古洛糖酸的水溶液中生产L-抗坏血酸的连续方法。 使用亚硫酸盐添加剂可降低产品流颜色，并通过与高分子量反应副产物结合而提高产品回收率。 在连续方法中，将反应物流与残余的亚硫酸盐和亚硫酸盐结合的副产物分离以产生富含水溶性抗坏血酸以回收的产物流，以及富含2-酮-L-古洛糖酸流，将其再循环至 反应堆。 反应中亚硫酸盐添加剂的原位使用增加了L-抗坏血酸的总产率，合成的选择性没有损失。

公开(公告)号：US06527690B2

公开(公告)日：2003-03-04

申请号：US09871695

申请日：2001-06-04

Applicant: Bhaskar Krishna Arumugam ,  Michael Eugene Burns ,  Dimmick Lee Bymaster ,  Jeffrey Scott DuPont ,  Robert Richard Dykstra ,  Robert Lee Eagan ,  Eddie Joseph Eckart ,  Jarvey Eugene Felty, Jr. ,  Kevin John Fontenot ,  Jeffrey William Green ,  Shane Kipley Kirk ,  Gary Paul Lutz ,  Tony Lee Sander ,  Thomas Hugh Williams ,  George Chester Zima

Inventor： Bhaskar Krishna Arumugam ,  Michael Eugene Burns ,  Dimmick Lee Bymaster ,  Jeffrey Scott DuPont ,  Robert Richard Dykstra ,  Robert Lee Eagan ,  Eddie Joseph Eckart ,  Jarvey Eugene Felty, Jr. ,  Kevin John Fontenot ,  Jeffrey William Green ,  Shane Kipley Kirk ,  Gary Paul Lutz ,  Tony Lee Sander ,  Thomas Hugh Williams ,  George Chester Zima

IPC: C07C23100

CPC classification number: C07C303/44 ,  C07C309/42

Abstract: The invention relates to a process for purifying and decolorizing a phenyl ester salt. The process combines a phenyl ester salt with a solvent to form a mixture and then stirs the mixture to form a slurry. The phenyl ester salt is substantially insoluble in this solvent. The process then collects the phenyl ester salt from the slurry. The collected phenyl ester salt may then be optionally dried or recrystallized. The collected phenyl ester salt is dissolved in a solvent to form a solution. The solution is decolorized and then spray dried to form a powder of the phenyl ester salt. As a result of the process the phenyl ester salt powder has a higher purity and an improved color as compared to the starting phenyl ester salt.

公开(公告)号：US06872314B2

公开(公告)日：2005-03-29

申请号：US10651819

申请日：2003-08-29

Applicant: Brendan William Boyd ,  Bhaskar Krishna Arumugam

Inventor： Brendan William Boyd ,  Bhaskar Krishna Arumugam

IPC: C07B63/00 ,  B01D15/08

CPC classification number: C07B63/00

Abstract: Disclosed is a process for dewatering an organic compound other than a carboxylic acid using a simulated moving bed (SMB) containing a solid with different absorptivities for water and the organic compound. The organic compound is fed into the SMB as an aqueous solution and desorbed with a desorbent other than water. The process is particularly useful for dewatering organic compounds produced by fermentation, biomass extraction, biocatalytic, and enzymatic processes.

Abstract translation: 公开了一种使用含有对水和有机化合物具有不同吸收率的固体的模拟移动床（SMB）对除羧酸以外的有机化合物进行脱水的方法。 将有机化合物作为水溶液加入到SMB中，并用除了水之外的解吸剂解吸附。 该方法对于通过发酵，生物质提取，生物催化和酶法生产的有机化合物的脱水特别有用。

公开(公告)号：US06670505B1

公开(公告)日：2003-12-30

申请号：US09519936

申请日：2000-03-07

Applicant: Nick Allen Collins ,  Mark Robert Shelton ,  George William Tindall ,  Steven Thomas Perri ,  Ruairi Seosamh O'Meadhra ,  Chester Wayne Sink ,  Bhaskar Krishna Arumugam ,  John Clark Hubbs

Inventor： Nick Allen Collins ,  Mark Robert Shelton ,  George William Tindall ,  Steven Thomas Perri ,  Ruairi Seosamh O'Meadhra ,  Chester Wayne Sink ,  Bhaskar Krishna Arumugam ,  John Clark Hubbs

IPC: C07C5142

CPC classification number: C07C51/43 ,  Y02P20/582 ,  Y10S435/803 ,  Y10S435/876 ,  Y10S435/896 ,  C07C59/347

Abstract: A process for recovering a desired organic acid from a solution includes the steps of: providing an aqueous solution including at least one desired organic acid or its acid anion; adjusting the proton concentration in the aqueous solution to a desired level, with the desired proton concentration being selected, at least in part, by the amount of available protons needed to associate with the acid anions of the desired organic acid(s) to be recovered and/or acid anions that are weaker than the desired organic acids; and recovering at least a portion of the at least one desired organic acid from the aqueous phase. The desired proton concentration can be based on the amount of available protons being greater than, less than or substantially equal, to the amount of protons needed to associate with the anion of the desired organic acid(s) and acid anions that are weaker than the desired organic acid(s). Specific examples of suitable organic acids include, but are not limited to, ascorbic, succinic, tartaric, glyconic, gulonic, citric, lactic, hialic, maleic, acetic, formic, gluconic pyruvic, propionic, butyric, itaconic acids and mixtures thereof. One embodiment of the present invention relates to the recovery of 2-keto-L-gulonic acid (KLG) from aqueous solutions such as fermentation baths.

Abstract translation: 从溶液中回收所需有机酸的方法包括以下步骤：提供包含至少一种所需有机酸或其酸阴离子的水溶液; 将所述水溶液中的质子浓度调节到所需的水平，其中所需质子浓度至少部分地被选择与需要回收的所需有机酸的酸性阴离子缔合所需的可用质子的量 和/或弱于所需有机酸的酸性阴离子; 以及从所述水相中回收所述至少一种所需有机酸的至少一部分。 期望的质子浓度可以基于可用质子的量大于，小于或基本上等于与所需有机酸的阴离子和酸阴离子相比所需的质子的量，其弱于 合适的有机酸的具体实例包括但不限于抗坏血酸，琥珀酸，酒石酸，葡萄糖酸，古洛糖酸，柠檬酸，乳酸，唾液酸，马来酸，乙酸，甲酸，葡萄糖酸，丙酸，丙酸，丁酸， 衣康酸及其混合物。 本发明的一个实施方案涉及从水溶液如发酵浴中回收2-酮-L-古洛糖酸（KLG）。

公开(公告)号：US06518454B1

公开(公告)日：2003-02-11

申请号：US09975872

申请日：2001-10-12

Applicant: Bhaskar Krishna Arumugam ,  Larry Wayne Blair ,  Brendan William Boyd ,  Nick Allen Collins ,  David Anthony Larkin ,  Steven Thomas Perri ,  Chester Wayne Sink

Inventor： Bhaskar Krishna Arumugam ,  Larry Wayne Blair ,  Brendan William Boyd ,  Nick Allen Collins ,  David Anthony Larkin ,  Steven Thomas Perri ,  Chester Wayne Sink

IPC: C07C6702

CPC classification number: C07C67/08 ,  C07C69/68 ,  C07C69/716

Abstract: Disclosed is a process wherein a solution of a carboxylic acid in a first solvent and an alcohol are fed to a simulated moving bed reactor (SMBR) containing a solid(s) to produce a first stream comprising a solution of an ester of the carboxylic acid and the alcohol and a second stream comprising the first solvent. The solid(s) present in the SMBR facilitates the esterification reaction and the separation of the first solvent from the carboxylic acid. The process is particularly valuable for the preparation of an alkanol solution of an alkyl 2-keto-L-gulonate ester (AKLG) from an aqueous fermentation broth containing dissolved 2-keto-L-gulonic acid (KLG) by feeding the fermentation broth and an alkanol to a simulated moving bed reactor which contains a solid acidic esterification catalyst to produce a stream comprising an alkanol solution of an ALKG. The alkanol solution of an ALKG may be used directly to convert the ALKG to ascorbic acid (Vitamin C).

Abstract translation: 公开了一种方法，其中将羧酸在第一溶剂和醇中的溶液进料到含有固体的模拟移动床反应器（SMBR）中以产生包含羧酸的酯溶液的第一物流 所述醇和包含所述第一溶剂的第二物流。 存在于SMBR中的固体促进酯化反应和第一溶剂与羧酸的分离。 该方法对于通过加入发酵液从含有溶解的2-酮-L-古洛糖酸（KLG）的水性发酵液中制备2-酮-L-古洛糖酸烷基酯（AKLG）的链烷醇溶液是特别有价值的， 将链烷醇加入到含有固体酸性酯化催化剂以产生包含ALKG的链烷醇溶液的流的模拟移动床反应器中。 ALKG的链烷醇溶液可以直接用于将ALKG转化为抗坏血酸（维生素C）。

公开(公告)号：US06476239B1

公开(公告)日：2002-11-05

申请号：US10074829

申请日：2002-02-12

Applicant: Bhaskar Krishna Arumugam ,  Steven Thomas Perri ,  Elaine Beatrice Mackenzie ,  Larry Wayne Blair ,  Joseph Robert Zoeller

Inventor： Bhaskar Krishna Arumugam ,  Steven Thomas Perri ,  Elaine Beatrice Mackenzie ,  Larry Wayne Blair ,  Joseph Robert Zoeller

IPC: C07D30762

CPC classification number: C07D307/62

Abstract: The present invention is a process for the preparation of ascorbic acid using a simulated moving bed (SMB) reactor system to accomplish the simultaneous conversion of KLG or a derivative of KLG to ascorbic acid and the separation of reaction products. The SMB reactor contains a solid or mixture of solids effective for catalyzing the reaction of KLG or its derivative and for separating the reactions products by selective adsorption of at least one product. In a general embodiment, this process involves (1) feeding a solution of KLG or a derivative thereof in a first solvent and a desorbent which is miscible with the first solvent, to a simulated moving bed reactor; (2) reacting the KLG or the KLG derivative to form ascorbic acid; and (3) removing from the simulated moving bed reactor (i) a first liquid stream comprising a solution of ascorbic acid in the desorbent and the first solvent (ii) a second liquid stream comprising the first solvent and the desorbent.

Abstract translation: 本发明是使用模拟移动床（SMB）反应器系统制备抗坏血酸的方法，以实现KLG或KLG的衍生物同时转化为抗坏血酸和分离反应产物。 SMB反应器含有对催化KLG或其衍生物的反应有效的固体或固体混合物，并且通过选择性吸附至少一种产物来分离反应产物。 在一般实施方案中，该方法包括（1）将KLG或其衍生物的溶液送入模拟移动床反应器中的第一溶剂和可与第一溶剂混溶的解吸剂; （2）使KLG或KLG衍生物反应形成抗坏血酸; （3）从模拟移动床反应器（i）中除去包含解吸剂中的抗坏血酸溶液的第一液体流和第一溶剂（ii）包含第一溶剂和解吸剂的第二液体流。