CN1017246B - 氨基糖碳酸化剂的制备方法 - Google Patents
氨基糖碳酸化剂的制备方法Info
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- CN1017246B CN1017246B CN87101874A CN87101874A CN1017246B CN 1017246 B CN1017246 B CN 1017246B CN 87101874 A CN87101874 A CN 87101874A CN 87101874 A CN87101874 A CN 87101874A CN 1017246 B CN1017246 B CN 1017246B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
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Abstract
氨基糖碳酸化剂是通过碳酸氢根离子与水溶液中的葡糖胺或半乳糖胺的氨基部分反应生成葡糖胺碳酸氢盐或半乳糖胺碳酸氢盐而制备的,接着通过干燥来分离该碳酸氢盐。所得到的干燥的2-氨基糖碳酸氢盐在室温下是稳定的,能用作碳酸化剂。也可用该碳酸化剂与其它成分掺和形成干燥的饮料混合物,该2-氨基糖碳酸氢盐一旦再水化就会释放出二氧化碳,且又把淡甜味带到该充碳酸气的饮料中。
Description
本发明涉及干燥的碳酸化剂,制备和使用这类干燥的碳酸化剂的方法和掺入这类干燥的碳酸化剂的产品。干燥的碳酸化剂是一种一旦接触水就会释放二氧化碳的物质,在需要泡腾的食品、饮料和药物应用中都可使用这类干燥的碳酸化剂。干燥的碳酸化剂可与其它物质如稀释剂、载体和调味剂混合,而后可复原成一种充碳酸气的饮料。
在先有技术中,人们长期以来一直在寻找具有良好泡腾性质而无反味作用的干燥的碳酸化剂。现有的干燥的碳酸化剂主要包括无机碳酸盐或无机碳酸氢盐的金属盐,其中最常见的是碳酸氢钠,但是,由于碳酸化剂一旦与水反应会释放出金属离子,因此这些无机碳酸化剂通常会给产品带来异味和咸味。
美国专利3,441,417和3,649,298介绍了某些氧、氮和硫羧基酐组合物作为干燥的碳酸化剂应用中的有机二氧化碳载体,然而,所介绍的方法中在制备这些有机碳酸化剂时需要光气,由于光气可能引起毒性问题,而这是食品应用中所不需要的。
英国专利申请GB2,037,760A介绍了作为泡腾组合物的有机二氧化碳载体的L-赖氨酸氨基甲酸酯的制备方法。
美国专利4237147介绍了一种“稳定的无定形碳酸盐”的制备方法,其方法包括(1)由一种糖和氢氧化钙在一定条件下形成一种加合物(2)在这种加合物中通入二氧化碳使其反应生成一种钙碳酸盐。这种钙碳酸盐主要作为碳酸化剂使用,其目的在于防止在碳酸化剂中引入钠离子,而钙离子没有盐味,是人体需要的主要矿物质之一,另外其碳酸化剂有
机二氧化碳载体是一种糖例如蔗糖,因此会给充碳酸气的溶液带来淡甜味。
本发明主要是要避免上面讨论的那些缺点。本发明包括发现2-氨基糖、葡糖胺和半乳糖胺的碳酸氢盐可以用作干燥的碳酸化剂。2-氨基糖碳酸氢盐一旦与水接触,就能迅速地释放二氧化碳并对所得到的充碳酸气的水液提供淡甜味。因此,这些干燥的碳酸化剂特别适用于饮料混合物。
本发明也提供了一种制备干燥,稳定的碳酸化剂的方法,该方法包括使水溶液中的葡糖胺或半乳糖胺的氨基部分与碳酸氢根离子反应,结果生成葡糖胺或半乳糖胺碳酸氢盐的溶液,接着通过干燥从溶液中分离该碳酸氢盐。
在本发明的一个实施例中,通过制备游离的2-氨基糖水溶液和随后将二氧化碳引入该溶液,使碳酸氢根离子与氨基反应。在本发明的另一个实施例中,通过使2-氨基糖的盐和强碱离子交换树脂接触,使碳酸氢根离子和氨基部分有效地反应,该强碱离子交换树脂含有碳酸氢根离子。从2-氨基糖中除去该盐的阴离子并用碳酸氢根离子代替,从而形成2-氨基糖碳酸氢盐。
本发明的方法是利用天然存在的2-氨基糖,即:2-氨基-2-脱氧-D-葡萄糖(葡糖胺)或2-氨基-2-脱氧-D-半乳糖(半乳糖胺)的其中之一种。通常,这两种2-氨基糖是从天然多糖来源如几丁质(葡糖胺),和胶原材料如腱和软骨(半乳糖胺)得到的。这两种2-氨基糖,一般是以其无机酸盐如盐酸盐的形式回收的。
因此,葡糖胺盐酸盐可用众所周知的几丁质的无机酸水解的方法来获得,几丁质是一种多糖,其中主要的重复单位是N-乙酰氨基葡糖。几丁质很容易由甲壳纲如蟹、虾、淡水小龙虾、淡水鳌虾等的壳用众所周知的方法来制备。
而后,游离的氨基糖水溶液可通过中和酸性盐酸盐溶液来制备,最好是使酸性盐酸盐溶液通过离子交换柱。在本发明中,可以使用任何适宜的弱碱阴离子交换树脂以制备游离的氨基糖溶液,如DOWEX MWA-1(DOW化学公司)。用适当的氢氧化物溶液如5%氢氧化钠水溶液,把该离子交换柱装成氢氧化物型,这种填充有氢氧化物的离子交换树脂的活性部位可用于进行离子交换反应。
然后,在足以使离子交换反应发生的速率下,使该氨基糖盐的水溶液通过准备好的离子交换柱。接着,通过用去离子水洗脱柱,pH呈碱性的洗出液各部分含有2-氨基糖游离碱,较好为收集的pH>8的各部分,pH较低的后面的各部分洗出液显示出转化成游离碱更不完全,在有足够浓度的酸式盐的存在下,这个结果将导致降低最后产品碳酸氢盐的香气质量。
葡糖胺盐酸盐和半乳糖胺盐酸盐均易溶于水,因此可以通过把该盐酸盐溶解于水很容易地制得它们的水溶液,例如,根据所需的粘度,葡糖胺盐酸盐的浓度可配制到25%(重量)水溶液。如果被通过的盐酸盐水溶液是通过离子交换树脂来制备游离碱,那么,为了防止通过离子交换柱的高粘性溶液所出现的问题,可以配制较低浓度的溶液。例如,葡糖胺盐酸盐,在采用碱性离子交换方法中,游离氨基糖的不期望的变褐色反应速率会随着浓度的增加而增加,因此,对较高浓度的溶液而言,特别重要的是,经柱的流动速率以及后面的2-氨基糖的程序都要尽可能地快。在进行离子交换时,最好将柱冷却至15℃以下,将进一步有助于使不需要的降解反应降至最低限度。
然后,使游离氨基糖水溶液与适当来源的碳酸氢根离子反应以生产本发明的2-氨基糖碳酸氢盐。在本发明的最佳实施例中,通过氨基糖溶液的碳酸化,即通过使该氨基糖溶液与二氧化碳接触可以做到,用二氧化碳气体或干冰可实现这种碳酸饱和。二氧化碳在水溶液中的溶解度
以及所形成的各种碳酸盐会影响与氨基糖的反应,对简单的碳酸盐水溶液来说,四种溶质成分即CO2、H2CO3、HCO- 3、CO2- 3的浓度会彼此影响平衡的性质,可用下列平衡反应来表示:
当各种碳酸氢盐溶液的pH值在7到10时,HCO- 3在水溶液中占优势,而且,因为2-氨基糖的氨基的pKa常数也约为10(葡糖胺=9.7),当pH值降到10以下时,越来越多的氨基就会与碳酸氢根离子反应生成氨基糖碳酸氢盐,当收集的碳酸饱和的各部分流出液(pH8-10)时,该溶液的pH就会降低且有更多的碳酸氢根离子形成并与氨基糖反应。当充碳酸气步结束时,该溶液pH达到约6-7范围。
为了增强二氧化碳的溶解作用,增强与2-氨基糖的反应,较好是使该溶液保持在室温以下,最好是保持在10℃以下。在充碳酸气时,保持该溶液在0-2℃,而不是25℃,就会增产5-10%。干冰的加入既会降低该溶液的温度,同时也将二氧化碳引入该溶液。在充碳酸气时,通过使压力增大到约690kPa(100磅/平方英寸),也会增加碳酸氢盐的收率。在690kPa下,产量将随着充碳酸气步的时间增加到约90分钟而提高,但尚未发现更高的压力或更长的时间有更明显的有利作用。
在本发明的另一个实施例中,含有所需氨基糖碳酸氢盐的水溶液可以直接从氨基糖盐通过离子交换方法来形成。在这个实施例中,使2-氨基糖盐如盐酸盐的水溶液与含有碳酸氢根离子的强碱离子交换树脂接触,通过先用碳酸氢钠或碳酸氢钾洗脱该树脂柱,然后将氨基糖盐酸盐
的水溶液通过该离子交换树脂柱,从该盐中除去氯离子并用碳酸氢根离子代替之,以便使所得到的洗出液含有氨基糖碳酸氢盐。
水溶液中的氨基糖碳酸氢盐,可通过干燥该溶液如冰冻干燥、喷雾干燥或真空干燥来分离。溶液中的氨基糖碳酸氢盐对热敏感,热能引起二氧化碳的释放以及其它不需要的降解反应。由于这种热不稳定性,所使用的干燥方法中应当避免长时间的受高温或过高温的作用。因此,较好的干燥技术是冻干该水溶液,使二氧化碳和氨基糖反应混合物以及所得到的碳酸氢盐溶液的温度维持在15℃以下,以冷冻该碳酸氢盐溶液也是较佳的,在制备中,应尽快冷冻干燥。
使冻干步骤持续到产品的水分含量小于8%(重量),最好是小于5%,所得到的干燥的氨基糖碳酸氢盐是一种白色粉末。
因此,所分离的该干燥的氨基糖碳酸氢盐在室温下是稳定的且具有淡甜味,当它暴露于空气中时,能吸收水分,特别是收湿的冻干产品。因此,在包装本发明的产品时,应倍加注意避免产品受潮。因此,包括本发明的碳酸氢盐作为一种成分的干燥的饮料组合物应当贮藏在密封的气密的、无水容器中。
向2-氨基糖碳酸氢盐的溶液加入各种载体,可降低最后产品的吸湿性以及有利于干燥步骤,良好的载体应当具有结合水分的能力,以便它不能随意引起粘着性或促进二氧化碳的损失或变褐色。酸性条件会促进二氧化碳从碳酸氢盐中的释放,因此,载体如麦芽糖糊精和阿拉伯树胶,由于其低pH值,会降低二氧化碳的保留值,是不够优选的,而某些改性的糊精却具有非酸性pH值,表现出更适合于这种应用,已发现一种这样改性的糊精即:N-ZORBIT(National Starch & Chemical)尤其适用于作为载体。
一旦氨基糖碳酸氢盐在水溶液中复原就会释放二氧化碳。一般说来,二氧化碳的释放可用下列离子方程式来表示:
其中R是2-氨基糖,而不是氨基。为了促进二氧化碳的释放,溶液的pH最好是酸性的。
本发明的碳酸化剂除了能释放二氧化碳外,还给该充碳酸气的溶液带来淡甜味。因此本发明的碳酸化剂尤其适用于饮料应用,因为其甜味通常是所期望的。在这些应用中,氨基糖碳酸氢盐用作碳酸化剂可能会减少通常所加入的糖量,各种适宜的干燥的稀释剂,载体和调味剂可和碳酸氢盐掺和在一起形成一种干燥的饮料组合物,而尤其用作干燥的饮料组合物的成分,即本发明碳酸化剂也可用于其它应用中,在这些应用中,一旦加水就会释放所期望的二氧化碳。
下面提到的各实施例仅是进一步说明本发明的某些实施,而并不在任何方面构成对本发明的限制。所有百分数均用重量表示,除非另有说明。
实施例1
用6N盐酸,接着用去离子水洗涤DOWX MWA-1大孔碱性离子交换树脂,接着将该树脂装到9.5厘米直径的玻璃柱上,装至80厘米高,用去离子水充分洗涤该装好的柱,然后将12升5%氢氧化钠溶液通过该柱,随后用去离子水充分洗涤以便使洗出液与去离子水具有相同的pH值。接着把整个柱冷却到8℃以下。
将去离子水(15℃)中的1200毫升18%葡糖胺盐酸盐溶液以25毫升/分的速率通过该柱,随后,冷的去离子水(15℃)以相同的洗脱速率通过。收集pH高于8.3的各部分洗出液(每份300-500毫升),接着在276KPa(40磅/平方英寸)的二氧化碳的压力下,在10℃下充碳酸气1小时,接着,冷冻所得溶液并冷冻干燥到最后含水量为5.0-6.5%,
总产量为155克。最后冷冻干燥的葡糖胺碳酸氢盐的氯化物含量小于0.6%,与葡糖胺碳酸氢盐的二氧化碳理论含量93毫升/克相比,该产品的二氧化碳平均产量为75-88毫升/克(已换算成0℃和760mmHg的标准状态。88毫升/克产品的熔点测定表明在93℃下开始分解,红外光谱与氨基碳酸氢盐盐键的形成相一致。
实施例2
成分 干燥的饮料混合物% 消耗量%
糖 61.79 9.20
柠檬酸 4.84 0.72
苹果酸 4.84 0.72
苹果汁固形物 3.81 0.57
速溶茶 0.46 0.07
苹果食用香料 0.38 0.06
桃食用香料 0.08 0.01
葡糖胺碳酸氢盐 23.80 3.54
水 - 85.11
100.0 100.00
为了得到均一的混合物,根据实施例1所叙述的方法而生产,含二氧化碳量为75毫升/克的葡糖胺碳酸氢盐与上表所列的其它干燥的成分掺和在一起。将21克所得干燥的饮料混合物搅拌加入120毫升冷水中,约30-40秒完全溶解,饮料继续放出二氧化碳气泡达3-4分钟,每体积该制取的饮料放出3体积二氧化碳气体。
实施例3
成分 干燥的饮料混合物% 消耗量%
糖 78.71 10.51
柠檬酸 6.00 0.80
磷酸一钙 0.26 0.03
草莓食用香料 0.69 0.09
红#40(着色剂) 0.07 0.01
葡糖胺碳酸氢盐 14.27 1.91
水 - 86.64
100.00 100.00
用实施例1相同方法而得到的葡糖胺碳酸氢盐来配制含有上述成分的配方,用18.5克该混合物配制成120毫升充碳酸气的软饮料,约30-45秒得到完全溶液,可观察到的冒泡时间持续约3分钟,每体积所制备的饮料约放出2体积的二氧化碳。
实施例4
用6N盐酸洗涤DOWEX MSA-2离子交换树脂(强碱Ⅱ型,大孔S-DVB球形颗粒)并用去离子水漂洗,将该树脂装到9.5厘米直径,高达80厘米的柱上。接着用去离子水彻底洗脱该柱,将8升5%碳酸氢钠溶液通过该柱,随后用去离子水洗脱,直到洗出液pH与去离子水相同为止。
使在去离子水中的700毫升20%葡糖胺盐酸盐溶液以25毫升/分的速率通过上述树脂柱,随后用去离子水洗脱。收集具有pH6.85-7.40的各部分洗出液(500-600毫升),冷冻并冻干,使最后含水量为5.8-7.2%,总产量为98克,冻干产品的氯化物含量为2.0-2.5%,该产品的平均二氧化碳含量为60毫升/克。
Claims (6)
1、一种制备干燥的碳酸化剂的方法,该方法包括通过离子交换使水溶液中的碳酸氢根离子与葡糖胺或半乳糖胺的氨基部分反应,以便在该溶液中生成葡糖胺碳酸氢盐或半乳糖胺碳酸氢盐并通过干燥来分离该产品。
2、根据权利要求1的方法,其中碳酸氢盐是通过冻干来分离的。
3、根据权利要求1的方法,其中通过装填一种含有碳酸氢盐的强碱性离子交换树脂并使该装填的树脂与葡糖胺或半乳糖胺的无机酸盐的水溶液接触而使碳酸氢根离子与氨基部分反应。
4、根据权利要求1的方法,其中通过把二氧化碳引入葡糖胺或半乳糖胺的水溶液中使碳酸氢根离子与氨基部分反应。
5、根据权利要求4的方法,其中水溶液是由葡糖胺或半乳糖胺盐酸盐水溶液通过弱碱离子交换柱并收集pH8以上的各洗出液部分而得到的。
6、根据权利要求4的方法,其中溶液在约276-690KPa压力下,保持与二氧化碳气体接触约60-90分钟。
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GB2316851A (en) * | 1996-09-09 | 1998-03-11 | Timothy John Parsons | Carbonated tea |
US6391864B1 (en) * | 1998-08-19 | 2002-05-21 | Joint Juice, Inc. | Food supplement containing a cartilage supplement |
US6706309B1 (en) | 1998-11-25 | 2004-03-16 | William F. Aftoora | Liquefied water soluble acidity-reducing formulation for food and beverage products |
AU2005203619B2 (en) * | 1999-06-22 | 2009-02-26 | Premier Nutrition Corporation | Cartilage enhancing food supplements and methods of preparing the same |
US7851458B2 (en) * | 1999-06-22 | 2010-12-14 | Joint Juice, Inc. | Cartilage enhancing food supplements and methods of preparing the same |
WO2001093832A2 (en) * | 2000-06-02 | 2001-12-13 | The Procter & Gamble Company | Aqueous chondroprotective compositions having defined dosage requirements for efficacious delivery |
BR0111378A (pt) * | 2000-06-02 | 2003-06-17 | Procter & Gamble | Kits e métodos para otimizar a eficácia de composições, condriprotetoras |
US20030069202A1 (en) * | 2000-06-02 | 2003-04-10 | Kern Kenneth Norman | Compositions, kits, and methods for promoting defined health benefits |
CA2408023C (en) * | 2002-10-15 | 2012-01-03 | Purepharm Inc. | Glucosamine as a food and beverage additive |
US20070259094A1 (en) * | 2002-10-21 | 2007-11-08 | Willem Wassenaar | N-acetylglucosamine as a food and beverage additive |
US9089156B2 (en) * | 2006-06-05 | 2015-07-28 | Stokely-Van Camp, Inc. | Reducing muscle soreness with glucosamine compositions |
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US2297734A (en) * | 1940-12-26 | 1942-10-06 | Trojan Powder Co | Stabilization of nitrated carbohydrates |
FR1295343A (fr) * | 1959-08-03 | 1962-06-08 | Chugai Pharmaceutical Co Ltd | Procédé de fabrication de dérivés de glucosamine |
US3441417A (en) * | 1965-10-05 | 1969-04-29 | Gen Foods Corp | Beverage product and process |
US3518343A (en) * | 1967-10-02 | 1970-06-30 | Miles Lab | Effervescent tablet and process for making same |
US3649298A (en) * | 1970-04-16 | 1972-03-14 | Gen Mills Inc | Carbonation concentrates for beverages and process of producing carbonated beverages |
US4127645A (en) * | 1976-05-21 | 1978-11-28 | Life Savers, Inc. | Effervescent tablet and method |
US4371616A (en) * | 1981-08-26 | 1983-02-01 | Hydrocarbon Research, Inc. | Process for producing L-sugars |
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US4579285A (en) * | 1984-04-19 | 1986-04-01 | Hunter Edwin J | Adjustable sprinkler system |
EP0185196B1 (en) * | 1984-12-13 | 1992-03-04 | Societe Des Produits Nestle S.A. | Carbonation agent |
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