WO2020239012A1 - Procédé de préparation d'hydroxyéthylcellulose - Google Patents

Procédé de préparation d'hydroxyéthylcellulose Download PDF

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Publication number
WO2020239012A1
WO2020239012A1 PCT/CN2020/092884 CN2020092884W WO2020239012A1 WO 2020239012 A1 WO2020239012 A1 WO 2020239012A1 CN 2020092884 W CN2020092884 W CN 2020092884W WO 2020239012 A1 WO2020239012 A1 WO 2020239012A1
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WIPO (PCT)
Prior art keywords
hydroxyethyl cellulose
washing
water
solvent
preparing
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Ceased
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PCT/CN2020/092884
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English (en)
Chinese (zh)
Inventor
滕鲲
李青华
刘涛
李长胤
滕波
张燕
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Shandong Eton New Material Co Ltd
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Shandong Eton New Material Co Ltd
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Priority to AU2020281382A priority Critical patent/AU2020281382A1/en
Publication of WO2020239012A1 publication Critical patent/WO2020239012A1/fr
Priority to ZA2021/09246A priority patent/ZA202109246B/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B11/00—Preparation of cellulose ethers
    • C08B11/02—Alkyl or cycloalkyl ethers
    • C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
    • C08B11/08—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals with hydroxylated hydrocarbon radicals; Esters, ethers, or acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
    • C08B15/10—Crosslinking of cellulose

Definitions

  • the invention belongs to the technical field of cellulose, and particularly relates to a method for preparing hydroxyethyl cellulose.
  • Hydroxyethyl cellulose is a white or light yellow, odorless, non-toxic fibrous or powdered solid, which belongs to non-ionic soluble cellulose ethers. Because HEC has good thickening, suspending, dispersing, emulsifying, bonding, filming, protecting moisture and providing protective colloids, it has been widely used in petroleum exploration, coatings, construction, medicine and food, textiles, papermaking and polymers Polymerization and other fields.
  • Ash content that is, the residual amount of inorganic salts generated during the reaction process is an important parameter to measure the quality of hydroxyethyl cellulose.
  • the product needs to be washed repeatedly with washing liquid.
  • “Pharmaceutical and Chemical Industry” 2006 Issue 8 “Synthesis and Application of Hydroxyethyl Cellulose” mentions the use of sodium hydroxide to alkalize cotton fiber, and after etherification, acid is used to neutralize the alkali in the system, and the salt produced is ethanol. Washing 3 to 4 times to remove, the single use of ethanol is 10 times the quality of cotton fiber.
  • hydroxyethyl cellulose mostly uses alcohol (or ketone, etc.)/water mixed solvents for product washing and purification, where the mass fraction of water is 10%-30%, requiring 3 to 4 washing operations.
  • the continuous washing process disclosed in the patent application No. 201810007892.6 to produce low ash hydroxyethyl cellulose the washing liquid used is C1 ⁇ C3 alcohols with a water mass fraction of 10%-18%.
  • the washing liquid The dosage is to adjust the solid content of the system to 5%-10%.
  • the above washing methods have the problems of large amount of organic solvents in the washing liquid, high washing cost, long recovery period, low production efficiency, and the washing liquid is flammable, and the safety hazard is large.
  • the use of alcohol cannot avoid the occupational health risks of acute and chronic poisoning. .
  • the invention provides a method for preparing hydroxyethyl cellulose with clean production, high production efficiency, low cost and high safety, and solves the problems existing in the prior art.
  • a method for preparing hydroxyethyl cellulose includes the process of preparing hydroxyethyl cellulose by alkalizing, etherifying, adjusting pH, washing and desalting, and solid-liquid separation of cellulose raw materials,
  • a precipitating agent which is a salt that is immiscible with hydroxyethyl cellulose in water
  • a step of adding a cross-linking agent is also included, and the cross-linking agent can undergo a cross-linking reaction with the hydroxyethyl cellulose.
  • Precipitating agent and crosslinking agent can be added to the reaction at one time or in batches.
  • the salt as a precipitant will weaken the hydrogen bond between water and hydroxyethyl cellulose, dehydrate the hydroxyethyl cellulose, and the molecular chain curls and twists to form a network agglomerated structure to form precipitation in water, inhibiting hydroxyethyl
  • the base cellulose is water-soluble in the subsequent water washing and purification process, and the precipitating agent is dissolved in the washing water, and then the precipitated hydroxyethyl cellulose and the salt dissolved in the water are separated by centrifugation; the cross-linking agent makes the hydroxyethyl cellulose
  • the molecules are bonded and cross-linked to form a water-insoluble network polymer within a certain period of time, delaying the water-soluble time of hydroxyethyl cellulose and realizing pure water washing.
  • the cation of the water-soluble salt as a precipitating agent is one or more of sodium, iron, ammonium, magnesium, aluminum, and zinc, and the anion is chloride, phosphate, sulfate, sulfite, One or more of nitrate, carbonate and borate; preferably, the salt that is immiscible with hydroxyethyl cellulose in water is selected from disodium hydrogen phosphate, sodium sulfite, magnesium sulfate, aluminum sulfate, and sodium nitrate Any one or more of sodium sulfate, sodium carbonate, and diammonium hydrogen phosphate.
  • the total amount of the precipitating agent is 0.8 to 1.2 times the mass of the cellulose raw material.
  • the crosslinking agent is a dialdehyde aqueous solution, preferably a glyoxal aqueous solution with a mass fraction of 30% to 42%, preferably diluted with water to a concentration of 5% to 42%.
  • the temperature of the cross-linking reaction is 30-35°C
  • the cross-linking time is 3 to 4 hours
  • the total amount of cross-linking agent is 0.15-0.3 times the mass of the cellulose raw material
  • the time and amount of the cross-linking agent can be Make the hydroxyethyl cellulose molecules deeply cross-linked and prevent the hydroxyethyl cellulose from dissolving in water for a certain period of time.
  • washing method is water washing.
  • the temperature of the soft water for washing is 12-20°C
  • the pH is 6-7
  • the amount of soft water is 15-20 times the quality of the cellulose raw material
  • the washing time is 5-20min, which ensures the washing efficiency without causing hydroxyethyl.
  • the base cellulose is dissolved in water washing and cannot be separated into solid and liquid.
  • Soft water is water that does not contain or contains less soluble calcium and magnesium compounds.
  • the cellulose undergoes alkalization and etherification reactions in the solvent, but the solvent needs to be removed before or after the pH is adjusted.
  • the solid-liquid separation method such as centrifugation or pressure filtration can be selected when the solvent is removed; the solvent is selected From one or more of tert-butanol, isopropanol, acetone, and ethylene glycol dimethyl ether.
  • the material needs to be dried after removing the solvent to ensure that the solvent is fully removed.
  • the purpose is to neutralize excess alkali and adjust the pH of the reaction mixture to be neutral or weakly acidic.
  • the precipitation agent is added before the solvent is removed, and the solvent removal method is centrifugal separation.
  • the precipitation agent is a water-soluble salt, which destroys the hydration function of hydroxyethyl cellulose and inhibits the swelling and dissolution of hydroxyethyl cellulose.
  • the precipitant is preferably added before the solvent is removed, because when the solvent is removed by centrifugation, a large amount of electrolyte increases the water content in the liquid phase, while the water content in the solid phase decreases. The low water content and the inhibitory effect of the precipitant make the ethyl acetate Crude cellulose-based products are not prone to material agglomeration and partial dissolution, which is beneficial to the subsequent drying process.
  • the crosslinking agent should be added after adjusting the pH. Because the crosslinking agent will form a hemiacetal structure between the alcohol solvent molecules and the hydroxyethyl cellulose molecules, the hemiacetal structure will be de-crosslinked in the subsequent washing process, and the small alcohol molecules will be separated from the hydroxyethyl cellulose molecules. And enter the wastewater; what is more serious is that the small alcohol molecules that are not removed during washing will be carried into the hydroxyethyl cellulose product, which affects the effective content of the product.
  • the cross-linked hydroxyethyl cellulose will change color and yellow due to the high temperature during drying, which will affect the product quality. Therefore, when an alcohol solvent is selected for the reaction, the crosslinking agent is preferably added after the alcohol solvent is removed, and more preferably after the alcohol solvent is removed and the temperature is dried and cooled to prevent the alcohol molecules from affecting the hydroxyethyl cellulose. The impact of the product.
  • cellulose ether products such as hydroxypropyl methyl cellulose
  • hydroxyethyl cellulose does not have high-temperature gel properties.
  • pure water cannot be used to wash products.
  • alcohol (or ketone)/water mixed solvents can be used for washing.
  • the amount of organic solvents is large, solvent recovery is required, and the production cost is high. And in terms of safety, there is a risk of flammability and explosion.
  • the present invention formulates a production process based on the properties of hydroxyethyl cellulose.
  • the hydroxyethyl cellulose inhibits dissolution and/or in water. Or delay the dissolution to achieve water washing and desalination, ensuring the quality of the product.
  • the washing liquid does not use organic solvents and there is no washing solvent recovery process, the production cost is significantly reduced, and the safety hazards caused by the use of organic solvents are reduced. And occupational hygiene risks, and the washing efficiency is high, one washing can achieve the purpose of washing, saving washing time and improving production efficiency.
  • the powder I enters the dryer, and the solvent is recovered until no distillate is steamed out to obtain powder II;
  • the powder II enters the washing kettle, add 14T soft water with a temperature of 18°C and a pH value of 6.7, and stir for 20 minutes to obtain slurry II;
  • Slurry II enters the centrifuge, solid-liquid separation, powder III and waste water are obtained;
  • the powder III enters the dryer for drying to obtain the finished product hydroxyethyl cellulose.
  • part of the precipitating agent is added before alkalization, because the presence of electrolyte will reduce the amount of free alkali to a certain extent, improve the alkalization effect, thereby improving product quality and inhibiting side reactions.
  • the precipitation agent is divided Add in one time, that is, the remaining precipitant is added after etherification, and new water will be generated during the subsequent neutralization, which can dissolve this part of the precipitant.
  • Slurry II enters the centrifuge, solid-liquid separation, powder I and solvent are obtained;
  • the powder I enters the dryer, and the solvent is recovered until no distillate is steamed out to obtain powder II;
  • the powder II enters the washing kettle, add 11T of soft water with a temperature of 19°C and a pH value of 6.5, and stir for 5 minutes to obtain slurry III;
  • Slurry III enters the centrifuge, solid-liquid separation, powder III and waste water are obtained;
  • the powder III enters the dryer for drying to obtain the finished product hydroxyethyl cellulose.
  • the ash content of the obtained hydroxyethyl cellulose product is 4.7%, and the product yield reaches 95%.
  • Slurry II enters the centrifuge, solid-liquid separation, powder I and solvent are obtained;
  • the powder I enters the dryer, and the solvent is recovered until no distillate is steamed out to obtain powder II;
  • the powder II enters the washing kettle, add 12T of soft water with a temperature of 20°C and a pH value of 6.4, and stir for 10 minutes to obtain slurry III;
  • Slurry III enters the centrifuge, solid-liquid separation, powder III and waste water are obtained;
  • the powder III enters the dryer for drying to obtain the finished product hydroxyethyl cellulose;
  • the ash content of the obtained hydroxyethyl cellulose product is 4.0%, and the product yield reaches 95%.
  • Examples 1-3 of the application of the present invention by adding a precipitating agent during the reaction, the water solubility of hydroxyethyl cellulose is inhibited, and the salt generated by the reaction is removed by washing with water.
  • Table 1 The comparison between the production process described in the "Synthesis and Application of Hydroxyethyl Cellulose" in “Pharmaceutical and Chemical Industry” 2006 issue 8 and the production process of Examples 1-3 of the present application is shown in Table 1.
  • the powder I enters the dryer, and the solvent is recovered until no distillate is steamed out to obtain powder II;
  • the powder III enters the washing kettle, add 14T soft water with a temperature of 19°C and a pH of 6.5, and stir for 20 minutes to obtain slurry II;
  • Slurry II enters the centrifuge, solid-liquid separation, powder IV and waste water are obtained, and the centrifugal operation time is 8 minutes;
  • the ash content of the obtained hydroxyethyl cellulose product is 2.8%, and the product yield reaches 95%.
  • the powder I enters the dryer, and the solvent is recovered until no distillate is steamed out to obtain powder II;
  • the powder II enters the washing kettle, add 11T of soft water with a temperature of 17°C and a pH value of 6.8, and stir for 5 minutes to obtain slurry II;
  • the powder III enters the dryer for drying to obtain the finished product hydroxyethyl cellulose.
  • the powder I enters the dryer, and the solvent is recovered until no distillate is steamed out to obtain powder II;
  • the powder II enters the washing kettle, add 13T of soft water with a temperature of 20°C and a pH of 6.2, and stir for 15 minutes to obtain slurry II;
  • Slurry II enters the centrifuge, solid-liquid separation, powder III and waste water are obtained, centrifugal operation time is 7 minutes;
  • the powder III enters the dryer for drying to obtain the finished product hydroxyethyl cellulose.
  • the ash content of the obtained hydroxyethyl cellulose product is 3.8%, and the product yield reaches 95%.
  • the two aldehyde groups of glyoxal react with the two hydroxyl groups of hydroxyethyl cellulose to form two hemiacetal structures, that is, crosslinking reaction occurs.
  • Numerous hemiacetal structures are filled between the hydroxyethyl cellulose polymer chains, so that multiple hydroxyethyl cellulose polymer chains form a cross-linked network polymer.
  • the hydroxyethyl cellulose of this structure is not in water. Dissolve.
  • this cross-linked structure will de-cross-link, that is, the hemiacetal structure is hydrolyzed at a certain rate, until the cross-link is destroyed, the polymer chain is de-cross-linked, and the hydroxyethyl cellulose will quickly dissolve.
  • This phenomenon is called delayed dissolution, and the time before dissolution is the delayed dissolution time.
  • the prolonged dissolution time is greatly affected by the pH value.
  • the prolonged dissolution time in the present invention refers to the prolonged dissolution time under the conditions of room temperature and pH value of 6-7.
  • Application Examples 4-6 of the present invention prolong the dissolution time of hydroxyethyl cellulose by adding a large amount of crosslinking agent during the reaction process, and realize the removal of the salt generated by the reaction by washing with water.
  • the patent application with application number 201810007892.6 uses waste etherification liquid or C1-C3 alcohols for desalination and washing. The comparison with the production process of Examples 4-6 of the present application is shown in Table 2.
  • the production process of the present invention makes the hydroxyethyl cellulose delayed in water-soluble time longer by reasonably designing the amount of cross-linking agent, cross-linking time, and temperature, and cooperates with the water temperature and time of the washing process to achieve complete washing. Desalting.
  • A Add 400kg of sodium nitrate and 160kg of flake caustic soda into the reaction kettle. After mixing with the solvent evenly, add 700kg of cotton fiber and carry out alkalization reaction at 18°C for 1h; add 800kg of ethylene oxide and carry out etherification reaction at 65°C2.5 h, to obtain crude hydroxyethyl cellulose, then add 200kg of sodium sulfate to the reactor and mix evenly, add hydrochloric acid to neutralize the excess alkali, and the obtained slurry I contains 230kg of sodium chloride (theoretical calculation value);
  • the powder I enters the dryer, and the solvent is recovered until no distillate is steamed out to obtain powder II;
  • the powder III enters the washing kettle, add 14T of water with a temperature of 19°C and a pH value of 6.5, stir for 20 minutes to obtain slurry II;
  • Slurry II enters the centrifuge, solid-liquid separation, powder IV and waste water are obtained, and the centrifugal operation time is 8 minutes;
  • the powder IV enters the dryer for drying to obtain the finished product hydroxyethyl cellulose.
  • Example 7 uses the precipitant and the crosslinking agent to treat the crude hydroxyethyl cellulose at the same time, changes the dissolution of the hydroxyethyl cellulose in water, and matches the water temperature and time of the washing process to achieve complete washing and desalination.
  • the production process of the present invention can reduce the washing solvent loss by 50-120 kg, reduce the steam consumption by 2 to 3 tons, and reduce the production cost by producing a single ton of hydroxyethyl cellulose product.
  • the total amount of washing liquid is reduced by half, and the salt in the product can be effectively removed through one washing, saving washing time by 1 to 2.5 hours, and improving production efficiency.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

L'invention concerne un procédé de préparation d'hydroxyéthylcellulose. Le procédé de préparation d'hydroxyéthylcellulose comprend un procédé de soumission d'une matière première de cellulose à une alcalinisation, une éthérification, un réglage du pH, un lavage et une désalinisation et une séparation solide-liquide pour obtenir de l'hydroxyéthylcellulose et comprend également l'étape d'ajout d'un précipitant avant le lavage et la désalinisation et/ou comprend également l'étape d'ajout d'un agent de réticulation entre le réglage du pH et le lavage et la désalinisation. Le procédé de préparation d'hydroxyéthylcellulose inhibe la dissolution et/ou retarde la dissolution de l'hydroxyéthylcellulose dans l'eau, permet d'obtenir un lavage et une désalinisation et assure la qualité du produit ; par rapport aux procédés de production classiques, le liquide de lavage n'utilise pas de solvants organiques, il n'y a pas d'étape de traitement de récupération de solvant de lavage, les coûts de production sont significativement réduits et les risques de sécurité et les risques de santé au travail provoqués par l'utilisation de solvants organiques sont réduits ; en outre, l'efficacité de lavage est élevée, un seul lavage peut atteindre l'objectif de lavage, d'économie de temps de lavage et d'amélioration de l'efficacité de production.
PCT/CN2020/092884 2019-05-30 2020-05-28 Procédé de préparation d'hydroxyéthylcellulose Ceased WO2020239012A1 (fr)

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AU2020281382A AU2020281382A1 (en) 2019-05-30 2020-05-28 Method for preparing hydroxyethyl cellulose
ZA2021/09246A ZA202109246B (en) 2019-05-30 2021-11-18 Method for preparing hydroxyethyl cellulose

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CN201910465188.XA CN110156898B (zh) 2019-05-30 2019-05-30 一种制备羟乙基纤维素的方法

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CN110156898B (zh) * 2019-05-30 2020-08-07 山东一滕新材料股份有限公司 一种制备羟乙基纤维素的方法
CN110981975A (zh) * 2019-11-28 2020-04-10 泸州北方纤维素有限公司 提高羟乙基纤维素粘度的方法
CN112812898A (zh) * 2020-12-31 2021-05-18 山东天和纸业有限公司 一种有机溶剂法纤维素洗涤剂以及纤维素制备方法
CN116693703A (zh) * 2023-07-12 2023-09-05 浦拉司科技（上海）有限责任公司 一种羟乙基纤维素去除金属离子的方法
CN117510997A (zh) * 2023-12-25 2024-02-06 泸州北方纤维素有限公司 提高羟乙基纤维素抗氧化性的方法

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CN102492044A (zh) * 2011-12-05 2012-06-13 泸州北方化学工业有限公司 羟乙基纤维素精制方法
KR20170076937A (ko) * 2015-12-24 2017-07-05 롯데정밀화학 주식회사 히드록시알킬 셀룰로오스의 제조방법 및 그 방법에 의해 제조된 히드록시알킬 셀룰로오스
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CN110156898B (zh) 2020-08-07
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AU2020281382A1 (en) 2021-06-03
AU2020104427A4 (en) 2021-07-01

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