WO2024108895A1 - 一种重烷基酚的回收再利用方法 - Google Patents

一种重烷基酚的回收再利用方法 Download PDF

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WO2024108895A1
WO2024108895A1 PCT/CN2023/090731 CN2023090731W WO2024108895A1 WO 2024108895 A1 WO2024108895 A1 WO 2024108895A1 CN 2023090731 W CN2023090731 W CN 2023090731W WO 2024108895 A1 WO2024108895 A1 WO 2024108895A1
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heavy
alkylphenol
recycling
reaction
temperature
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French (fr)
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杨香莲
陈福新
陈琦
戴杰
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江苏迈达新材料股份有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/02—Alkenes
    • C07C11/08—Alkenes with four carbon atoms
    • C07C11/09—Isobutene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/06—Alkylated phenols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/06—Alkylated phenols
    • C07C39/07—Alkylated phenols containing only methyl groups, e.g. cresols, xylenols

Definitions

  • the invention belongs to the technical field of organic synthesis technology, and specifically relates to a method for recycling heavy alkylphenol.
  • antioxidant BHT 2,6-di-tert-butyl-4-methylphenol. It is one of the important phenol antioxidants and is also recognized as a highly effective alkylphenol antioxidant in the world. It has the advantages of good oil solubility, high antioxidant efficiency, strong adaptability, and no pollution. It is one of the preferred antioxidant varieties in many industries and products. It is widely used in different industries such as gasoline, lubricating oil, aviation kerosene, plastics, rubber products, cosmetics, and medicine. In addition, it can also be used for food antioxidants, especially for oil and fat foods.
  • the purification process of antioxidant BHT generally adopts solvent crystallization method, the crystallization mother liquor is first distilled at atmospheric pressure to recover alcohol, and then vacuum distilled to separate the front fraction, the rear fraction, and the BHT crude product.
  • the distillation residue is called heavy alkyl phenol, the main component of which is a mixture of BHT and other high-boiling alkyl phenols, and the total alkyl phenol content is greater than 90%.
  • heavy alkyl phenol is generally treated as waste liquid, which not only has high processing cost, but also is not green and environmentally friendly. In order to change this situation, it is urgent to explore a method for recycling and reusing heavy alkyl phenol.
  • the object of the present invention is to provide a method for recycling heavy alkylphenol to solve the problems raised in the above background technology.
  • the present invention provides the following technical scheme: a method for recycling heavy alkylphenol, wherein the method uses heavy alkylphenol (distillation residue of antioxidant BHT) to undergo dealkylation reaction under the action of a catalyst, and the generated isobutylene is introduced into an absorption bottle and then subjected to an alkylation reaction; after the dealkylation, a mixed liquid (main products are mixed cresols and mono-tert-butyl cresol) is obtained, and light components (isobutylene dimer and trimer) are distilled out under normal pressure and recovered as a solvent; a phenol mixture is distilled out under negative pressure, and the recovered mixture is used for alkylation reaction or directly sold; and finally, a small amount of residue is discharged and treated as solid waste.
  • heavy alkylphenol distillation residue of antioxidant BHT
  • the heavy alkyl phenol and the catalyst are added into a three-necked flask in a certain proportion
  • the catalyst is preferably concentrated sulfuric acid or sulfonic acid, and the mass ratio of the heavy alkyl phenol to the catalyst is preferably 100:0.3-2.
  • the dealkylation reaction is preferably carried out at a temperature of 150-180°C.
  • the isobutylene produced by the reaction is discharged from the top of the condenser and passed into an absorption bottle prepared with p-cresol and catalyst.
  • the mass ratio of p-cresol to catalyst is 100:1-4, and the alkylation reaction temperature is preferably 60-70°C.
  • the light components are distilled out under normal pressure, preferably at a distillation temperature of 100-130°C.
  • the present invention has the following beneficial effects:
  • the heavy alkylphenol recovery and recycling method of the present invention comprises the following steps: per ton of the heavy alkylphenol undergoes a dealkylation reaction under the action of an acidic catalyst, and about 350 kg of isobutylene, 500 kg of mixed phenol, 105 kg of solvent, and about 45 kg of residue are recovered; per ton of the heavy alkylphenol, economic benefits are greater than RMB 10,000, and hazardous waste is reduced by about 95%, thereby greatly improving the profit margin of the antioxidant BHT, and achieving very considerable economic benefits; the equipment used for recovery is simple, and the economic benefits generated by the recovery of the heavy alkylphenol are good, which not only greatly improves the utilization value of the heavy alkylphenol, but also reduces the generation of a large amount of hazardous waste.
  • FIG1 is a flow chart of a method for recycling heavy alkylphenol according to the present invention.
  • an embodiment of the present invention provides a method for recycling heavy alkylphenol, comprising the following steps:
  • the main products are mixed cresols and mono-tert-butyl cresol.
  • the light components are first removed by atmospheric distillation;
  • the heavy alkylphenol and the catalyst in step 1) are added into a three-necked flask in a certain proportion, wherein the catalyst is preferably concentrated sulfuric acid or sulfonic acid, and the mass ratio of the heavy alkylphenol to the catalyst is preferably 100:0.3-2.
  • the dealkylation reaction in step 2) is preferably carried out at a temperature of 150-180°C.
  • the isobutylene produced in the step 3) is discharged from the top of the condenser and passed into an absorption bottle prepared with p-cresol and catalyst.
  • the mass ratio of p-cresol to catalyst is 100:1-4, and the alkylation reaction temperature is preferably 60-70°C.
  • the light components are distilled out under normal pressure in step 4), and the distillation temperature is preferably 100-130°C.
  • the negative pressure distillation in step 5) preferably has a pressure of -0.06 to -0.10 MPa, and a distillation temperature of 160-190°C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明公开了一种重烷基酚的回收再利用方法，属于有机合成工艺技术领域，该方法具体包括以下步骤：1)将重烷基酚和催化剂按一定比例加入三口瓶中，搅拌均匀；2)加热至一定温度，进行脱烷基化反应；3)反应产生的异丁烯，从冷凝管顶部排出，通入吸收瓶中；4)脱烷基化结束，主要产物为混甲酚和单叔丁基甲酚，在一定温度下，先常压蒸馏脱去轻组分；5)在一定温度下，再负压蒸馏脱去酚类混合物；6)最后排出少量残渣，作固废处理。本发明重烷基酚的回收再利用方法，不仅大幅度提升了重烷基酚的利用价值，同时减少大量危废的产生。

Description

一种重烷基酚的回收再利用方法 技术领域
本发明属于有机合成工艺技术领域，具体涉及一种重烷基酚的回收再利用方法。
背景技术
抗氧化剂BHT化学名称2,6-二叔丁基-4-甲基苯酚，是重要的酚类抗氧化剂之一，也是世界上公认的一种高效烷基酚类抗氧剂。它具有油溶性好、抗氧效能高、适应性强、不污染等优点，是许多行业及产品的首选抗氧化剂品种之一，广泛应用于汽油、润滑油、航空煤油、塑料、橡胶制品、化妆品以及医药等不同行业中，另外还可用于食品抗氧化，特别是油类、脂肪类食品的抗氧化。
目前抗氧剂BHT的提纯工艺普遍采用溶剂结晶法，结晶母液先常压蒸馏回收酒精，再减压精馏分离出前馏分、后馏分、BHT粗品，精馏残液称之为重烷基酚，主要成分为BHT和其他高沸点烷基酚的混合物，烷基酚总含量大于90％。目前重烷基酚一般作为废液处理，不但处理成本高，且不绿色环保，为改变此现状，急需探索一种重烷基酚的回收再利用方法。
发明内容
本发明的目的在于提供一种重烷基酚的回收再利用方法，以解决上述背景技术中提出的问题。
为实现上述目的，本发明提供如下技术方案：一种重烷基酚的回收再利用方法，该方法采用重烷基酚(抗氧剂BHT的精馏残液)在催化剂作用下，发生脱烷基化反应，产生的异丁烯通入吸收瓶中，再进行烷基化反应；脱烷基化结束后得混合液(主要产物为混甲酚和单叔丁基甲酚)，常压蒸馏出轻组分(异丁烯二聚、三聚物)，回收作溶剂；负压蒸馏出酚类混合物，回收后套用于烷基化反应，或直接出售；最后排出少量残渣，作固废处理。
进一步地，所述将重烷基酚和催化剂按一定比例加入三口瓶中，催化剂优选浓硫酸或磺酸类，重烷基酚和催化剂的质量比优选为100：0.3～2。
进一步地，所述脱烷基化反应，优选温度150-180℃。
进一步地，所述反应产生的异丁烯，从冷凝管顶部排出，通入配制好对甲酚和催化剂的吸收瓶中，优选对甲酚和催化剂的质量比为100：1～4，优选烷基化反应温度60-70℃。
进一步地，所述常压蒸馏出轻组分，优选蒸馏温度100-130℃。
进一步地，所述负压蒸馏优选压力-0.06～-0.10MPa，优选蒸馏温度160-190℃。
与现有技术相比，本发明的有益效果是：
本发明重烷基酚的回收再利用方法，每吨重烷基酚在酸性催化剂作用下，发生脱烷基化反应，约回收异丁烯350kg，混酚500kg，溶剂105kg，残渣约45kg，每吨重烷基酚产生经济效益大于1万元人民币，且危废减少约95％，大幅度提升抗氧剂BHT的利润空间，经济效益非常可观，并且回收所采用的设备简单，回收重烷基酚所产生的经济效益好，不仅大幅度提升了重烷基酚的利用价值，同时减少大量危废的产生。
附图说明
图1为本发明一种重烷基酚的回收再利用方法的流程图。
具体实施方式
下面将结合本发明实施例中的附图，对本发明实施例中的技术方案进行清楚、完整地描述。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
参阅图1，本发明实施例提供一种重烷基酚的回收再利用方法，包括以下步骤：
1)将重烷基酚和催化剂按一定比例加入三口瓶中，搅拌均匀；
2)加热至一定温度，进行脱烷基化反应；
3)反应产生的异丁烯，从冷凝管顶部排出，通入吸收瓶中；
4)脱烷基化结束，主要产物为混甲酚和单叔丁基甲酚，在一定温度下，先常压蒸馏脱去轻组分；
5)在一定温度下，再负压蒸馏脱去酚类混合物；
6)最后排出少量残渣，作固废处理。
在本实施例中，所述步骤1)的重烷基酚和催化剂按一定比例加入三口瓶中，其中，催化剂优选浓硫酸或磺酸类，重烷基酚和催化剂的质量比优选为100：0.3～2。
在本实施例中，所述步骤2)中脱烷基化反应，优选控制温度为150-180℃。
在本实施例中，所述步骤3)中反应产生的异丁烯，从冷凝管顶部排出，通入配制好对甲酚和催化剂的吸收瓶中，优选对甲酚和催化剂的质量比为100：1～4，优选烷基化反应温度60-70℃。
在本实施例中，所述步骤4)中常压蒸馏出轻组分，优选蒸馏温度100-130℃。
在本实施例中，所述步骤5)中负压蒸馏优选压力-0.06～-0.10MPa，优选蒸馏温度160-190℃。
下面结合实施例对本发明作进一步描述：
实施例1
三口瓶中加入215.1g重烷基酚，4.0g浓硫酸，搅拌均匀，电热套加热，脱烷基化温度130-160℃，反应约2小时。温度100-130℃下，常压蒸馏脱去轻组分；温度160-190℃，压力-0.09MPa下，负压蒸馏脱去酚类混合物，所得各物质重量：异丁烯72.4g，混酚91.8g，溶剂19.5g，残渣35.4g。
实施例2
三口瓶中加入215.3g重烷基酚，3.0g浓硫酸，搅拌均匀，电热套加热，脱烷基化温度150-175℃，反应约2小时。温度100-130℃下，常压蒸馏脱去轻组分；温度160-190℃，压力-0.09MPa下，负压蒸馏脱去酚类混合物，所得各物质重量：异丁烯75.8g，混酚107.6g，溶剂23.7g，残渣11.2g。
实施例3
三口瓶中加入215.0g重烷基酚，2.0g浓硫酸，搅拌均匀，电热套加热，脱烷基化温度150-185℃，反应约2小时。温度100-130℃下，常压蒸馏脱去轻组分；温度160-190℃，压力-0.09MPa下，负压蒸馏脱去酚类混合物，所得各物质重量：异丁烯76.1g，混酚108.4g，溶剂23.2g，残渣9.7g。
综上所述，从上述实施例1-3的实施结果可知，在原料进行同比例添加时，采用本发明重烷基酚的回收再利用方法，每吨(1000kg)重烷基酚在酸性催化剂作用下，发生脱烷基化反应，约回收异丁烯350kg，混酚500kg，溶剂105kg，残渣约45kg，每吨重烷基酚产生经济效益大于1万元人民币，且危废减少约95％，大幅度提升抗氧剂BHT的利润空间，经济效益非常可观，并且回收所采用的设备简单，回收重烷基酚所产生的经济效益好，不仅大幅度提升了重烷基酚的利用价值，同时减少大量危废的产生。
尽管已描述了本发明的优选实施例，但本领域内的技术人员一旦得知了基本创造性概念，则可对这些实施例作出另外的变更和修改。所以，所附权利要求意欲解释为包括优选实施例以及落入本发明范围的所有变更和修改。
显然，本领域的技术人员可以对本发明进行各种改动和变型而不脱离本发明的精神和范围。这样，倘若本发明的这些修改和变型属于本发明权利要求及其等同技术的范围之内，则本发明也意图包含这些改动和变型在内。

Claims (9)

  1. 一种重烷基酚的回收再利用方法，其特征在于，该方法包括以下步骤：
    1)将重烷基酚和催化剂按一定比例加入三口瓶中，搅拌均匀；
    2)加热至一定温度，进行脱烷基化反应；
    3)反应产生的异丁烯，从冷凝管顶部排出，通入吸收瓶中；
    4)脱烷基化结束，主要产物为混甲酚和单叔丁基甲酚，在一定温度下，先常压蒸馏脱去轻组分；
    5)在一定温度下，再负压蒸馏脱去酚类混合物；
    6)最后排出少量残渣，作固废处理。
  2. 根据权利要求1所述的一种重烷基酚的回收再利用方法，其特征在于：所述步骤1)中重烷基酚和催化剂质量比为100：0.3-4。
  3. 根据权利要求1所述的一种重烷基酚的回收再利用方法，其特征在于：所述步骤2)中控制温度120-190℃，进行脱烷基化反应。
  4. 根据权利要求1所述的一种重烷基酚的回收再利用方法，其特征在于：所述步骤3)中反应产生的异丁烯，从冷凝管顶部排出，通入配制好对甲酚和催化剂的吸收瓶中，进行烷基化反应，反应温度60-80℃。
  5. 根据权利要求1所述的一种重烷基酚的回收再利用方法，其特征在于：所述步骤4)中从三口瓶中取样分析BHT含量小于1％时，脱烷基化反应结束。
  6. 根据权利要求5所述的一种重烷基酚的回收再利用方法，其特征在于：在温度90-140℃下，常压蒸馏脱去轻组分，主要为异丁烯二聚、三聚物等，回收作溶剂。
  7. 根据权利要求1所述的一种重烷基酚的回收再利用方法，其特征在于：所述步骤(5)中在温度150-190℃下，负压蒸馏脱去酚类混合物。
  8. 根据权利要求7所述的一种重烷基酚的回收再利用方法，其特征在于：酚类混合物主要为间/对甲酚及单叔丁基甲酚，含量大于95％，回收后套用于烷基化反应或直接出售。
  9. 根据权利要求1所述的一种重烷基酚的回收再利用方法，其特征在于： 所述步骤6)中排出的少量残渣为有机物残渣。
PCT/CN2023/090731 2022-11-23 2023-04-26 一种重烷基酚的回收再利用方法 WO2024108895A1 (zh)

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