CN101270032A - Method for preparing 1,5-pentanediol - Google Patents

Method for preparing 1,5-pentanediol Download PDF

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CN101270032A
CN101270032A CN 200810036088 CN200810036088A CN101270032A CN 101270032 A CN101270032 A CN 101270032A CN 200810036088 CN200810036088 CN 200810036088 CN 200810036088 A CN200810036088 A CN 200810036088A CN 101270032 A CN101270032 A CN 101270032A
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reaction
catalyst
ru
method
pentanediol
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CN 200810036088
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CN101270032B (en )
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宁春利
猛 张
张春雷
赵小岐
邵敬铭
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上海华谊丙烯酸有限公司
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    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of products other than chlorine, adipic acid, caprolactam, or chlorodifluoromethane, e.g. bulk or fine chemicals or pharmaceuticals
    • Y02P20/52Improvements relating to the production of products other than chlorine, adipic acid, caprolactam, or chlorodifluoromethane, e.g. bulk or fine chemicals or pharmaceuticals using catalysts, e.g. selective catalysts

Abstract

The present invention relates to a method used for preparing 1, 5-pentanediol with hydrogenation of 1, 5-glutaraldehyde. In the method, Ru is used as the load catalyst of active components; the weight percent of the Ru in the catalyst is 0.2 percent to 10 percent; the carrier is a molecular sieve, or one of or the mixture of Al2O3, SiO2, TiO2, MgO, amorphous aluminosilicate and activated carbon. When the 1, 5-glutaraldehyde is hydrogenated to prepare the 1, 5-pentanediol, the reaction conditions are mild; the catalyst has high activity; and the method is an effective way for preparing the 1, 5-pentanediol.

Description

一种1,5-戊二醇的制备方法技术领域本发明涉及一种1,5-戊二醛加氢制备1,5-戊二醇的方法,具体地说包括1,5-戊二醛加氢制备1,5-戊二醇的催化剂和反应工艺。 TECHNICAL FIELD The one l-pentanediol present invention relates to the hydrogenation of a 1,5-pentanediol 1,5 glutaraldehyde, glutaraldehyde specifically include 1,5 the hydrogenation catalyst and reaction process for preparing 1,5-pentanediol. 背景技术1,5-戊二醇是一种用途广泛的化学品,可直接用作切削油、特殊洗涤剂、乳胶漆的溶剂或润湿剂,也可用作生产新型聚酯、涂料、粘合剂、密封剂、增塑剂等的原料。 BACKGROUND OF THE INVENTION 1,5-pentanediol is a versatile chemical, can be used directly as a cutting oil, a special detergent, paint solvents or wetting agents, it can also be used to produce new polyester, paint, adhesive raw materials, sealants, plasticizers and the like. 其生产方法主要有以下四种:1)由四氢糠醇催化加氢制得,反应^a度300~330°C,反应压力22〜42MPa。 Its production process are the following four: 1) tetrahydrofurfuryl alcohol obtained by the catalytic hydrogenation, the reaction ^ a of 300 ~ 330 ° C, the reaction pressure 22~42MPa. 该方法反应压力高,增加了设备投资和操作难度;2)由环戊二烯光氧化制得的环氧戊烯醇于70〜10(TC和约6MPa压力下加氢制得。环戊二烯光氧化收率低,整个过程的经济性较差;3) 中国专利CN1565728A描述了1,5-戊二酸二甲酯在铜锌铝催化剂作用下于150〜350'C和3〜5MPa下加氢制备1,5-戊二醇的方法,1,5-戊二酸二甲酯转化率大于95%, 1,5-戊二醇选择性大于95%。 The high pressure reaction method, equipment investment and increases the difficulty of the operation; 2) cyclopentadiene photooxidation prepared epoxy pentenol at 70~10 (TC hydrogenation pressure of about 6MPa cyclopentadiene. photooxidation low yield, poor economics of the overall process; 3) described in Chinese Patent No. CN1565728A 1,5-dimethyl glutarate, copper-zinc aluminum in the catalyst and in 150~350'C added under 3~5MPa the method of preparing 1,5-pentanediol hydrogen, 1,5-dimethyl glutarate conversion was greater than 95%, 1,5-pentanediol selectivity is greater than 95%. 但该方法以戊二酸为起始原料,中间需经过酯化等反应步骤,流程较长。 However, the method glutaric acid as a starting material, intermediate and subject to esterification reaction step, long processes. 4)中国专利CN1072168A报道了以取代的乙烯基乙醚和取代的丙烯醛反应,生成取代的3,4-二氢吡喃,取代的3,4-二氢吡喃酸催化水解生成取代的戊二醛,然后加氢生成取代的戊二醇。 4) reported in Chinese patent CN1072168A substituted vinyl ether and a substituted acrolein reaction to produce the substituted 3,4-dihydropyran, substituted 3,4-dihydro-pyran-generated acid catalyzed hydrolysis of substituted glutaric aldehyde, then hydrogenation of substituted pentanediol. 该专利提及的加氢催化剂是雷内镍或改性雷内镍,或者负载铂、钯或镍的氧化铝。 The patents mentioned hydrogenation catalyst is nickel or modified Raney nickel-Ray, or platinum, palladium, nickel, or aluminum oxide. 发明内容本发明的目的在于提供一种1,5-戊二醛加氢制备1,5-戊二醇的方法,该方法采用以Ru为活性组分的负载型催化剂,该催化剂用于1,5-戊二醛加氢制备1,5-戊二醇反应时,活性、选择性高,反应条件温和,为制备l,5-戊二醇提供了一种新的有效途径。 Object of the present invention to provide a method for the hydrogenation of a 1,5-pentanediol 1,5 glutaraldehyde, the method employed to Ru as the active component of the supported catalyst, the catalyst is used 1, when glutaraldehyde 5- pentanediol hydrogenation reaction, the activity, selectivity, mild reaction conditions, to prepare L, 5- pentanediol provides a new effective way. 本发明是通过以下技术方案实现的:一种1,5-戊二醛加氢制备1,5-戊二醇的方法,该方法是以水、甲醇、乙醇或异丙醇中的一种或它们以任意比例混合的混合物为溶剂,以质量分数为5%~80%的1,5-戊二醛溶液为原料,采用Ru为活性组分的负载型催化剂,通过气-液-固三相催化加氢反应制备1,5-戊二醇。 The present invention is achieved by the following technical solutions: A method for the hydrogenation of 1,5-glutaraldehyde 1,5-pentanediol, which is one of water, methanol, ethanol or isopropanol or they are mixed in any proportion of the solvent mixture, mass fraction of 5% to 80% of 1,5-glutaraldehyde solution as raw materials for the Ru supported catalyst active components by gas - liquid - solid-phase 1,5-pentanediol catalytic hydrogenation. 采用的反应方式选择间歇釜式反应或固定床连续反应,负载型Ru催化剂载体为分子筛或A1203、 Si02、 Ti02、 MgO、无定形硅酸铝或活性碳中的一种或它们以任意比例混合的混合物, 优选为氢型分子筛HZSM-5、 HMCM-49、 HSAPO-34、 HMOR、 H卩或Y-Al203、 Si02、活性碳中的任何一种或它们的混合物。 The reaction methods used to select batch reactor or a fixed bed continuous reaction, the supported Ru catalyst support is a molecular sieve or A1203, one kind of Si02, Ti02, MgO, activated carbon or amorphous aluminosilicate, or mixture thereof in any ratio mixtures thereof, preferably hydrogen-type zeolite HZSM-5, HMCM-49, HSAPO-34, HMOR, H Jie or Y-Al203, Si02, any activated carbon or mixtures thereof. 负载型Ru催化剂中活性组分Ru占催化剂总量的质量分数为0.2%~10%,优选0.5%~6%。 Ru supported Ru catalysts active component of the total catalyst mass fraction of 0.2% to 10%, preferably from 0.5% to 6%. 负载型Ru催化剂采用浸渍法制备,是将钌的可溶性盐或络合物溶液按计量比加入预先成型的催化剂载体中进行浸渍,然后进行干燥和焙烧制得;该催化剂在使用前需用氢气进行还原处理,还原条件为氢气压力0.2~10.0MPa、氢气空速200〜1500h—、还原温度180~400°C、 还原时间l~24h,优选还原条件为氢气压力2.0~8.0MPa、氢气空速30(K800hf1、还原温度200~350°C、还原时间4〜20h。1,5-戊二醛加氢制备1,5-戊二醇采用的反应方式可以选择间歇釜式反应,也可以选择固定床连续反应。间歇釜式反应条件为:以水、甲醇、乙醇或异丙醇中的一种或它们以任倉比例的混合物作溶剂,原料1,5-戊二醛溶液的质量分数为5%~80%,反应温度50〜16(TC,反应压力0.5〜15.0MPa,反应时间l~24h;优选反应条件为:原料1,5-戊二醛溶液的质量分数为10%~50%,反应温度60~120°C,反应压力2.0〜8.0MPa,反应 The supported Ru catalyst was prepared by impregnation method, a solution of a soluble salt or complex of ruthenium metered addition of the catalyst carrier is impregnated preformed, followed by drying and calcining to obtain; the hydrogen catalyst is required prior to use reduction treatment, the reducing conditions of a hydrogen pressure of 0.2 ~ 10.0MPa, the hydrogen space velocity 200~1500h-, reduction temperature 180 ~ 400 ° C, the reduction time l ~ 24h, reducing conditions are preferably a hydrogen pressure of 2.0 ~ 8.0MPa, hydrogen space velocity 30 (K800hf1, reduction temperature 200 ~ 350 ° C, the reaction time of the reduction embodiment 4~20h.1,5- glutaraldehyde hydrogenation using 1,5-pentanediol can be selected batch reactor, a fixed bed may be selected batch reactor continuous reaction conditions: in one of water, methanol, ethanol or isopropanol or a mixture thereof in any ratio as a solvent cartridge, the mass fraction of the raw material 1,5-glutaraldehyde solution 5% ~ 80%, reaction temperature is 50~16 (TC, reaction pressure 0.5~15.0MPa, reaction time l ~ 24h; preferred reaction conditions are: 1,5-glutaraldehyde solution the mass fraction of raw material is 10% to 50%, the reaction a temperature of 60 ~ 120 ° C, the reaction pressure 2.0~8.0MPa, the reaction 间2~8h。固定床连续反应条件为:以水、甲醇、乙醇或异丙醇中的一种或它们以任意比例的混合物作溶剂,原料1,5-戊二醛溶液的质量分数5%~80%,反应温度5(M6(TC,反应压力0.5〜15.0MPa,原料1,5-戊二醛溶液空速0.5〜10.0h'1, H2/l,5-戊二醛摩尔比Ll〜100:l;优选反应条件为:原料1,5-戊二醛质量分数10%~50%,反应温度60~120°C,反应压力2.0〜8.0MPa, 1,5-戊二醛溶液空速lO^.Oh-1, H2/l,5-戊二醛摩尔比3:1〜20:1。具体实施方式下面将以具体的实施例来对本发明加以说明,但本发明保护范围不局限于这些实施例。 实施例卜8催化剂的制备:配網一定浓度的RuCl3水溶液按照计量比加入催化剂载体中學渍,然后在IIO'C下干燥12小时,450。CN2气氛下焙烧4小时。焙烧完毕后降至室温,装入反应器内, 用氢气300°C还原4小时,还原结束后将条件调整到反应所需条件。各实施例中催化剂组 Inter 2 ~ 8h fixed-bed continuous reaction conditions: In one of water, methanol, ethanol or isopropanol or a mixture thereof in any ratio as a solvent, 1,5-glutaraldehyde solution feed mass fraction of 5% ~ 80%, the reaction temperature is 5 (M6 (TC, reaction pressure 0.5~15.0MPa, 1,5 glutaraldehyde solution feed space velocity 0.5~10.0h'1, H2 / l, 5- a molar ratio of glutaraldehyde Ll~ 100: l; preferred reaction conditions are: 1,5 glutaraldehyde mass fraction of 10% to 50% of the starting material, the reaction temperature is 60 ~ 120 ° C, the reaction pressure 2.0~8.0MPa, 1,5- glutaraldehyde solution airspeed lO ^ .Oh-1, H2 / l, 3 5- glutaraldehyde molar ratio: 1~20: 1 DETAILED DESCRIPTION the following embodiments will be specific to the embodiment of the present invention will be described, but the scope of the present invention is not limited these BU Example 8 preparation of catalyst: a. distribution network after a certain concentration ratio in accordance with an aqueous solution of RuCl3 metered Secondary stains catalyst support, and then dried for 12 hours at IIO'C, baked for 4 hours in an atmosphere of calcination 450.CN2 completed. cooled to room temperature, loaded into a reactor, reduced with hydrogen 300 ° C 4 hours after the end of the reduction reaction conditions are adjusted to desired conditions. Example embodiments each catalyst 成见表l。表l.<table>table see original document page 5</column></row> <table>催化剂的反应活性评价:在500毫升不锈钢高压搅拌反应釜内,分别加入300克质量分数为20%的1,5-戊二醛溶液和一定量(以反应原料为基础)实施例1~4的催化剂中的一种, 氢气置换反应器后升温至反应温度,控制反应压力1.0〜5.0MPa、反应温度90〜11(TC,搅拌速度1000转。 Reactive catalyst was evaluated as shown in Table l in Table l <table> table see original document page 5 </ column> </ row> <table>:.. Stirred 500 ml stainless steel high pressure reaction kettle were added 300 g mass fraction of 1,5 20% glutaraldehyde solution and an amount of a catalyst Examples 1 to 4 (in the starting material based) embodiment, the hydrogen gas heated to the reaction temperature after the replacement of the reactor to control the reaction pressure 1.0~5.0MPa The reaction temperature is 90~11 (TC, stirring at 1,000 rpm. 实施例1~4中具体的反应条件及反应结果见表2。 Specific reaction conditions and reaction results of Examples 1 to 4 shown in Table 2. 表2.<table>table see original document page 5</column></row> <table>将实施例5~8中的催化剂100克分别装入固定床管式反应器,300'C用氢气还原4小时, 还原结束后降温至反应温度。 Table 2. <table> table see original document page 5 </ column> </ row> <table> catalyst of EXAMPLE 5-8 were charged 100 g bed tubular reactor, 300'C reduction with hydrogen 4 hours after the completion of the reduction reaction was cooled to temperature. 质量分数为25%的1,5-戊二醛溶液和氢气混合预热后进入反应器反应,实施例5〜8中具体反应条件及反应结果见表3。 Mass fraction of 25% glutaraldehyde solution of 1,5 and hydrogen into the reactor after the reaction mixture preheated 5 ~ 8 embodiment, the specific reaction conditions and reaction results are shown in Table 3. 表3.<table>table see original document page 5</column></row> <table> Table 3. <table> table see original document page 5 </ column> </ row> <table>

Claims (6)

  1. 1、一种1,5-戊二醇的制备方法,其特征在于该方法是以水、甲醇、乙醇或异丙醇中的一种或它们以任意比例混合的混合物为溶剂,以质量分数为5%~80%的1,5-戊二醛溶液为原料,采用Ru为活性组分的负载型Ru催化剂,通过气-液-固三相催化加氢反应制备1,5-戊二醇,采用的反应方式选择间歇釜式反应或固定床连续反应;负载型Ru催化剂载体为分子筛或Al2O3、SiO2、TiO2、MgO、无定形硅酸铝或活性碳中的一种或它们以任意比例混合的混合物;间歇釜式反应在温度50~160℃和压力0.5~15.0MPa下反应1~24小时;固定床连续反应的反应条件为反应温度50~160℃、反应压力0.5~15.0MPa、1,5-戊二醛溶液空速0.5~10.0h-1、H2/1,5-戊二醛摩尔比1∶1~100∶1。 1, a method for preparing 1,5-pentanediol, wherein the method is one of water, methanol, ethanol or isopropanol, or their mixtures in any ratio as a solvent, to a mass fraction of 5% to 80% 1,5-glutaraldehyde solution as raw material Ru Ru as catalytically active component supported by the gas - 1,5-pentanediol prepared by solid-phase catalytic hydrogenation reaction - solution the reaction methods used to select batch reactor or a fixed bed continuous reaction; supported Ru catalyst or a molecular sieve carrier is Al2O3, one kind of SiO2, TiO2, MgO, activated carbon or amorphous aluminosilicate, or mixture thereof in any ratio the mixture; batch reactor at a temperature of 50 ~ 160 ℃ and reaction pressure 0.5 ~ 15.0MPa 1 to 24 hours; the reaction conditions in a fixed bed continuous reaction reaction temperature 50 ~ 160 ℃, reaction pressure 0.5 ~ 15.0MPa, 1,5 - 0.5 ~ 10.0h-1, H2 / 1,5- glutaraldehyde molar ratio of 1/1 to 100:1 airspeed glutaraldehyde solution.
  2. 2、 根据权利要求1所述的方法,其特征在于负载型Ru催化剂载体为氢型分子筛HZSM-5、 HMCM-49、 HSAPO-34、 HMOR、 Hp或Y-Al203、 Si02、活性碳中的任一种或它们的混合物。 2. The method according to claim 1, wherein the supported Ru catalyst support is in the hydrogen form zeolite HZSM-5, HMCM-49, HSAPO-34, HMOR, Hp or Y-Al203, Si02, any of the activated carbon One or a mixture thereof.
  3. 3、 根据权利要求1所述的方法,其特征在于负载型Ru催化剂采用浸渍法制备,是将钌的可溶性盐或络合物溶液按计量比加入预先成型的催化剂载体中进行浸渍,然后进行干燥和焙烧制得,催化剂中Ru占催化剂总量的质量分数为0.2%~10%;该催化剂在使用前需用氢气进行还原处理,还原条件为氢气压力0.2〜10.0MPa、氢气空速200~1500h"、还原温度180~400°C、还原时间1〜24小时。 3. The method according to claim 1, wherein the supported Ru catalyst was prepared by impregnation method, a solution of a soluble salt or complex of ruthenium metered addition of the catalyst carrier is impregnated preformed and then dried and calcining to obtain, the mass fraction of the total amount of Ru in the catalyst accounted catalyst 0.2% to 10%; the hydrogen catalyst reduction treatment required prior to use, reducing conditions hydrogen pressure 0.2~10.0MPa, a space velocity of 200 ~ 1500h hydrogen "reduction temperature 180 ~ 400 ° C, the reduction time 1~24 hours.
  4. 4、 根据权利要求3所述的方法,其特征在于负载型Ru催化剂中Ru占催化剂总量的质量分数为0.5%~6%,催化剂的还原条件为氢气压力2.0〜8.0MPa、氢气空速300〜800h—1、还原温度200~350°C、还原时间4~20小时。 4. The method of claim 3, wherein the supported catalyst is Ru Ru mass fraction of total catalyst is 0.5% to 6%, a catalyst for reducing the hydrogen pressure 2.0~8.0MPa, hydrogen airspeed 300 ~800h-1, the reduction temperature 200 ~ 350 ° C, the reduction time of 4 to 20 hours.
  5. 5、 根据权利要求1所述的方法,其特征在于负载型Ru催化剂用于1,5-戊二醛加氢制1,5-戊二醇的间歇釜式反应条件为:1,5-戊二醛质量分数为10%~50%、反应温度60〜120'C、反应压力2.0〜8.0MPa、反应时间2~8小时。 5. The method of claim 1, wherein the supported Ru catalysts for 1,5 glutaraldehyde batch reactor conditions hydrogenation is 1,5-pentanediol: 1,5- dialdehyde mass fraction of 10% to 50%, the reaction temperature 60~120'C, reaction pressure 2.0~8.0MPa, the reaction time is 2 to 8 hours.
  6. 6、 根据权利要求1所述的方法,其特征在于负载型Ru催化剂用于1,5-戊二醛加氢制1,5-戊二醇的固定床连续反应条件为:1,5-戊二醛质量分数为10%~50%、反应温度60〜12(TC、反应压力2.0〜8.0MPa、 1,5-戊二醛溶液空速为1.0~8.0h"、 &/1,5-戊二醛摩尔比为3:1〜20:1。 6. The method of claim 1, wherein the supported Ru catalysts for the hydrogenation of 1,5-glutaraldehyde fixed bed continuous reaction of 1,5-pentanediol conditions: 1,5- dialdehyde mass fraction of 10% to 50%, the reaction temperature is 60~12 (TC, reaction pressure 2.0~8.0MPa, 1,5- glutaraldehyde solution space velocity of 1.0 ~ 8.0h ", & / 1,5- pentyl dialdehyde molar ratio of 3: 1~20: 1.
CN 200810036088 2008-04-16 2008-04-16 Method for preparing 1,5-pentanediol CN101270032B (en)

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CN101890361A (en) * 2010-07-27 2010-11-24 万华实业集团有限公司;烟台万华聚氨酯股份有限公司 Catalyst for use in highly selective preparation of gasoline fractions from synthesis gas and preparation method thereof
CN103111318A (en) * 2013-03-01 2013-05-22 江苏九九久科技股份有限公司 Supported catalyst with ruthenium (III) as active center and preparation method of catalyst
CN105289592A (en) * 2015-11-19 2016-02-03 中科合成油技术有限公司 Method for preparing gamma-valerolactone by acetylpropionic acid catalytic hydrogenation
CN106622219A (en) * 2016-10-28 2017-05-10 南京工业大学 Catalyst for producing tetrahydrofurfuryl alcohol through furfuryl alcohol liquid phase hydrogenation and preparation method and application thereof

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CN101890361A (en) * 2010-07-27 2010-11-24 万华实业集团有限公司;烟台万华聚氨酯股份有限公司 Catalyst for use in highly selective preparation of gasoline fractions from synthesis gas and preparation method thereof
CN101890361B (en) 2010-07-27 2013-04-24 万华实业集团有限公司 Preparation method of catalyst for use in highly selective preparation of gasoline fractions from synthesis gas
CN103111318A (en) * 2013-03-01 2013-05-22 江苏九九久科技股份有限公司 Supported catalyst with ruthenium (III) as active center and preparation method of catalyst
CN105289592A (en) * 2015-11-19 2016-02-03 中科合成油技术有限公司 Method for preparing gamma-valerolactone by acetylpropionic acid catalytic hydrogenation
CN105289592B (en) * 2015-11-19 2017-11-28 中科合成油技术有限公司 Catalytic hydrogenation of levulinic acid γ- valerolactone
CN106622219A (en) * 2016-10-28 2017-05-10 南京工业大学 Catalyst for producing tetrahydrofurfuryl alcohol through furfuryl alcohol liquid phase hydrogenation and preparation method and application thereof

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