WO2023123569A1 - 一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法 - Google Patents
一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
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- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
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- Y02W30/62—Plastics recycling; Rubber recycling
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- the invention relates to the field of chemical industry, in particular to a method for synthesizing n-hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate.
- the photodegradation of plastics is mainly caused by the action of oxygen in the air and ultraviolet light, including two processes of photooxidation and photodegradation.
- Light stabilizers have a significant effect on the photodegradation of polymers, so it is often necessary to add light stabilizers to plastics.
- 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl is an excellent light stabilizer, widely used in polyolefin plastics such as polypropylene and polybutene.
- the preparation technology of existing 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl generally uses 3,5-di-tert-butyl-4-hydroxybenzoic acid and n-hexadecyl as raw materials, adopts acid chloride method or Use acid, such as concentrated sulfuric acid, p-toluenesulfonic acid as a catalyst, and carry out esterification reaction under the action of the catalyst to obtain the target product.
- the acylating agent used in the acid chloride method is usually phosphorus oxychloride, which is highly toxic and volatile Substances that are likely to pollute the environment. After research, it is found that using concentrated sulfuric acid, p-toluenesulfonic acid, etc. as catalysts will easily cause the tert-butyl group on the product to fall off, thereby affecting product selectivity and yield.
- the object of the present invention is to overcome existing 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl in the preparation technology Raw material, when concentrated sulfuric acid, p-toluenesulfonic acid etc. are used as the defect of limited product selectivity and yield when catalyst, and then provide a kind of synthesis of n-hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate method.
- the present invention adopts the following technical solutions:
- a kind of synthetic method of 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl comprising the steps:
- Microchannel reactor of the present invention is existing conventional microchannel reactor, and the microchannel reactor that adopts in embodiment and comparative example is same microchannel reactor.
- the molar ratio of 3,5-di-tert-butyl-4-hydroxybenzoic acid, tetramethylammonium bromide and toluene in step 1) is 1:(0.01-0.03):(12-20).
- the molar ratio of 3,5-di-tert-butyl-4-hydroxybenzoic acid, tetramethylammonium bromide and toluene in step 1) is 1:(0.02-0.03):(15-20).
- the molar ratio of n-hexadecanol, 4-sulfonylcalix[6]arene and toluene in step 2) is 1:(0.01-0.03):(12-20).
- the molar ratio of 3,5-di-tert-butyl-4-hydroxybenzoic acid and n-hexadecanol in the microchannel reactor described in step 3) is 1:(0.9-1.1).
- the molar ratio of 3,5-di-tert-butyl-4-hydroxybenzoic acid and n-hexadecanol in the microchannel reactor in step 3) is 1:1.
- the flow rate of the 3,5-di-tert-butyl-4-hydroxybenzoic acid solution described in step 3) is 18-22ml/min
- the flow rate of the n-hexadecanol solution is 18-22ml /min.
- the flow rate of 3,5-di-tert-butyl-4-hydroxybenzoic acid solution and n-hexadecanol solution is the same, 3,5-in 3,5-di-tert-butyl-4-hydroxybenzoic acid solution
- the concentration of n-hexadecyl alcohol in di-tert-butyl-4-hydroxybenzoic acid and n-hexadecyl alcohol solution is the same.
- the reaction temperature is 55-65°C, and the reaction time is 80-100s.
- step 3 it also includes the step of cooling the reaction solution to room temperature, washing with water, and distillation under reduced pressure to obtain a crude product.
- step 3) also includes the step of recrystallizing the crude product.
- the crude product is recrystallized using ethanol.
- the synthetic method of 3,5-di-tert-butyl-4-hydroxybenzoate n-hexadecyl benzoate provided by the invention adopts specific 4-sulfonylcalix[6]arene as a catalyst, utilizes 4-sulfonylcalix[6] Aromatic multi-site sulfonic acid and its unique ring structure can be passed into the microchannel reactor together with the raw material liquid for rapid and efficient reaction at a lower temperature. At the same time, it can effectively improve the The yield and selectivity of n-hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, and the mild reaction conditions can greatly shorten the reaction time and improve the reaction efficiency.
- This embodiment provides a kind of synthetic method of 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl, comprising the steps:
- the reaction solution is cooled to room temperature, then the reaction solution was washed with water, and distilled under reduced pressure to obtain a crude product, which was recrystallized from ethanol to obtain the n-hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate with a yield of 90.8 %, after the reaction, the selectivity of 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl is 94.6% after the reaction liquid is analyzed by high performance liquid chromatography.
- This embodiment provides a kind of synthetic method of n-hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, comprising the following steps:
- the reaction solution is cooled to room temperature, then the reaction solution was washed with water, and distilled under reduced pressure to obtain a crude product, which was recrystallized from ethanol to obtain the n-hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate with a yield of 89.5 %, after the reaction, the selectivity of 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl is 94.9% after the reaction liquid is analyzed by high performance liquid chromatography.
- This embodiment provides a kind of synthetic method of n-hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, comprising the following steps:
- the reaction solution is cooled to room temperature, then the reaction solution was washed with water, and distilled under reduced pressure to obtain a crude product, which was recrystallized from ethanol to obtain the n-hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate with a yield of 90.2 %, after the reaction, the selectivity of 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl is 94.4% after the reaction liquid is analyzed by high performance liquid chromatography.
- This comparative example provides a kind of synthetic method of 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl, comprising the steps:
- the reaction solution is cooled to room temperature, then the reaction solution was washed with water, and distilled under reduced pressure to obtain a crude product, which was recrystallized from ethanol to obtain the n-hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate with a yield of 86.5 %, after the reaction, the selectivity of 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl is 92.3% after the reaction liquid is analyzed by high performance liquid chromatography.
- This comparative example provides a kind of synthetic method of 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl, comprising the steps:
- the reaction solution is cooled to room temperature, then the reaction solution was washed with water, and distilled under reduced pressure to obtain a crude product, which was recrystallized from ethanol to obtain the n-hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate with a yield of 80.2 %, after the reaction, the selectivity of 3,5-di-tert-butyl-4-hydroxybenzoate n-hexadecyl benzoate was 82.9% after the reaction liquid was analyzed by high performance liquid chromatography.
- This comparative example provides a kind of synthetic method of 3,5-di-tert-butyl-4-hydroxybenzoic acid n-hexadecyl, comprising the steps:
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Abstract
提供3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法,包括如下步骤:将3,5-二叔丁基-4-羟基苯甲酸、四甲基溴化铵和甲苯混合,配置得到3,5-二叔丁基-4-羟基苯甲酸溶液;将正十六醇、4-磺酰杯[6]芳烃和甲苯混合,配置得到正十六醇溶液;将3,5-二叔丁基-4-羟基苯甲酸溶液和正十六醇溶液同时通入微通道反应器中进行反应,得到所述3,5-二叔丁基-4-羟基苯甲酸正十六酯。可有效提高3,5-二叔丁基-4-羟基苯甲酸正十六酯的产率和选择性,同时反应条件温和,极大缩短反应时间,提高反应效率。
Description
本发明涉及化工领域,具体涉及一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法。
塑料的光降解主要由空气中的氧和紫外光线作用导致的,其中包括光氧化和光降解两个过程。光稳定剂对聚合物的光降解具有显著的作用,因此,往往在塑料中需要添加光稳定剂。3,5-二叔丁基-4-羟基苯甲酸正十六酯是一种性能优异的光稳定剂,广泛用于聚丙烯、聚丁烯等聚烯烃塑料中。
现有3,5-二叔丁基-4-羟基苯甲酸正十六酯的制备工艺一般以3,5-二叔丁基-4-羟基苯甲酸和正十六酯作为原料,采用酰氯法或者以酸,如浓硫酸,对甲基苯磺酸作为催化剂,在催化剂的作用下进行酯化反应,从而获得目标产品,酰氯法所用酰化试剂通常为三氯氧磷,其属于高毒易挥发物质,易对环境造成污染。经研究发现以浓硫酸,对甲基苯磺酸等作为催化剂易造成产物上的叔丁基脱落,进而影响产品选择性和收率。
发明内容
本发明的目的在于克服现有3,5-二叔丁基-4-羟基苯甲酸正十六酯的制备工艺中以3,5-二叔丁基-4-羟基苯甲酸和正十六酯作为原料,以浓硫酸,对甲基苯磺酸等作为催化剂时产品选择性和收率有限的缺陷,进而提供一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法。
为达到上述目的,本发明采用如下技术方案:
一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法,包括如下步骤:
1)将3,5-二叔丁基-4-羟基苯甲酸、四甲基溴化铵和甲苯混合,配置得到3,5-二叔丁基-4-羟基苯甲酸溶液;
2)将正十六醇、4-磺酰杯[6]芳烃和甲苯混合,配置得到正十六醇溶液;
3)将3,5-二叔丁基-4-羟基苯甲酸溶液和正十六醇溶液同时通入微通道反应器中进行反应,得到所述3,5-二叔丁基-4-羟基苯甲酸正十六酯。
本发明微通道反应器为现有常规微通道反应器,且实施例和对比例中采用的微通道 反应器为同一微通道反应器。
优选的,步骤1)中3,5-二叔丁基-4-羟基苯甲酸、四甲基溴化铵和甲苯的摩尔比为1:(0.01-0.03):(12-20)。
优选的,步骤1)中3,5-二叔丁基-4-羟基苯甲酸、四甲基溴化铵和甲苯的摩尔比为1:(0.02-0.03):(15-20)。
优选的,步骤2)中正十六醇、4-磺酰杯[6]芳烃和甲苯的摩尔比为1:(0.01-0.03):(12-20)。
优选的,步骤3)所述微通道反应器中3,5-二叔丁基-4-羟基苯甲酸和正十六醇的摩尔比为1:(0.9-1.1)。优选的,步骤3)所述微通道反应器中3,5-二叔丁基-4-羟基苯甲酸和正十六醇的摩尔比为1:1。
优选的,步骤3)中所述3,5-二叔丁基-4-羟基苯甲酸溶液的通入流速为18-22ml/min,所述正十六醇溶液的通入流速为18-22ml/min。
优选的,3,5-二叔丁基-4-羟基苯甲酸溶液和正十六醇溶液的通入流速相同,3,5-二叔丁基-4-羟基苯甲酸溶液中的3,5-二叔丁基-4-羟基苯甲酸和正十六醇溶液中的正十六醇浓度相同。
优选的,所述反应温度为55-65℃,反应时间为80-100s。
优选的,步骤3)中反应结束后还包括对反应液进行降温至室温、用水洗涤、减压蒸馏,得到粗产物的步骤。
优选的,步骤3)中还包括对粗产物进行重结晶的步骤。
优选的,采用乙醇对粗产物进行重结晶。
本发明所述4-磺酰杯[6]芳烃的结构如下所示:
本发明的有益效果:
本发明提供的3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法,采用特定的4-磺酰杯[6]芳烃作为催化剂,利用4-磺酰杯[6]芳烃多位点磺酸以及独特的环状结构,将其与原料液共同通入微通道反应器在较低温度下进行快速高效反应,同时配合四甲基溴化铵多相催化作用,可有效提高3,5-二叔丁基-4-羟基苯甲酸正十六酯的产率和选择性,同时反应条件温和,可极大缩短反应时间,提高反应效率。
提供下述实施例是为了更好地进一步理解本发明,并不局限于所述最佳实施方式,不对本发明的内容和保护范围构成限制,任何人在本发明的启示下或是将本发明与其他现有技术的特征进行组合而得出的任何与本发明相同或相近似的产品,均落在本发明的保护范围之内。
实施例中未注明具体实验步骤或条件者,按照本领域内的文献所描述的常规实验步骤的操作或条件即可进行。所用试剂或仪器未注明生产厂商者,均为可以通过市购获得的常规试剂产品。
实施例1
本实施例提供一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法,包括如下步 骤:
1)将1mol的3,5-二叔丁基-4-羟基苯甲酸、0.02mol的四甲基溴化铵和15mol的甲苯混合,配置得到3,5-二叔丁基-4-羟基苯甲酸溶液;
2)将1mol的正十六醇、0.02mol的4-磺酰杯[6]芳烃和15mol的甲苯混合,配置得到正十六醇溶液;
3)将3,5-二叔丁基-4-羟基苯甲酸溶液和正十六醇溶液分别用计量泵同时通入微通道反应器中进行反应(控制所述3,5-二叔丁基-4-羟基苯甲酸溶液的通入流速为20ml/min,所述正十六醇溶液的通入流速为20ml/min),反应温度为60℃,反应时间为90s,反应结束后将反应液降温至室温,然后将反应液用水洗涤,减压蒸馏,得粗产品,粗产品用乙醇重结晶,得到所述3,5-二叔丁基-4-羟基苯甲酸正十六酯,收率为90.8%,反应结束后将反应液经过高效液相色谱分析其3,5-二叔丁基-4-羟基苯甲酸正十六酯的选择性为94.6%。
实施例2
本实施例提供一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法,包括如下步骤:
1)将1mol的3,5-二叔丁基-4-羟基苯甲酸、0.02mol的四甲基溴化铵和15mol的甲苯混合,配置得到3,5-二叔丁基-4-羟基苯甲酸溶液;
2)将1mol的正十六醇、0.02mol的4-磺酰杯[6]芳烃和15mol的甲苯混合,配置得到正十六醇溶液;
3)将3,5-二叔丁基-4-羟基苯甲酸溶液和正十六醇溶液分别用计量泵同时通入微通道反应器中进行反应(控制所述3,5-二叔丁基-4-羟基苯甲酸溶液的通入流速为20ml/min,所述正十六醇溶液的通入流速为20ml/min),反应温度为55℃,反应时间为90s,反应结束后将反应液降温至室温,然后将反应液用水洗涤,减压蒸馏,得粗产品,粗产品用乙醇重结晶,得到所述3,5-二叔丁基-4-羟基苯甲酸正十六酯,收率为89.5%,反应结束后将反应液经过高效液相色谱分析其3,5-二叔丁基-4-羟基苯甲酸正十六酯的选择性为94.9%。
实施例3
本实施例提供一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法,包括如下步骤:
1)将1mol的3,5-二叔丁基-4-羟基苯甲酸、0.02mol的四甲基溴化铵和15mol的甲 苯混合,配置得到3,5-二叔丁基-4-羟基苯甲酸溶液;
2)将1mol的正十六醇、0.02mol的4-磺酰杯[6]芳烃和15mol的甲苯混合,配置得到正十六醇溶液;
3)将3,5-二叔丁基-4-羟基苯甲酸溶液和正十六醇溶液分别用计量泵同时通入微通道反应器中进行反应(控制所述3,5-二叔丁基-4-羟基苯甲酸溶液的通入流速为20ml/min,所述正十六醇溶液的通入流速为20ml/min),反应温度为64℃,反应时间为90s,反应结束后将反应液降温至室温,然后将反应液用水洗涤,减压蒸馏,得粗产品,粗产品用乙醇重结晶,得到所述3,5-二叔丁基-4-羟基苯甲酸正十六酯,收率为90.2%,反应结束后将反应液经过高效液相色谱分析其3,5-二叔丁基-4-羟基苯甲酸正十六酯的选择性为94.4%。
对比例1
本对比例提供一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法,包括如下步骤:
1)将1mol的3,5-二叔丁基-4-羟基苯甲酸和15mol的甲苯混合,配置得到3,5-二叔丁基-4-羟基苯甲酸溶液;
2)将1mol的正十六醇、0.02mol的4-磺酰杯[6]芳烃和15mol的甲苯混合,配置得到正十六醇溶液;
3)将3,5-二叔丁基-4-羟基苯甲酸溶液和正十六醇溶液分别用计量泵同时通入微通道反应器中进行反应(控制所述3,5-二叔丁基-4-羟基苯甲酸溶液的通入流速为20ml/min,所述正十六醇溶液的通入流速为20ml/min),反应温度为60℃,反应时间为90s,反应结束后将反应液降温至室温,然后将反应液用水洗涤,减压蒸馏,得粗产品,粗产品用乙醇重结晶,得到所述3,5-二叔丁基-4-羟基苯甲酸正十六酯,收率为86.5%,反应结束后将反应液经过高效液相色谱分析其3,5-二叔丁基-4-羟基苯甲酸正十六酯的选择性为92.3%。
对比例2
本对比例提供一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法,包括如下步骤:
1)将1mol的3,5-二叔丁基-4-羟基苯甲酸、0.02mol的四甲基溴化铵和15mol的甲苯混合,配置得到3,5-二叔丁基-4-羟基苯甲酸溶液;
2)将1mol的正十六醇、0.12mol的对甲基苯磺酸和15mol的甲苯混合,配置得到 正十六醇溶液;
3)将3,5-二叔丁基-4-羟基苯甲酸溶液和正十六醇溶液分别用计量泵同时通入微通道反应器中进行反应(控制所述3,5-二叔丁基-4-羟基苯甲酸溶液的通入流速为20ml/min,所述正十六醇溶液的通入流速为20ml/min),反应温度为60℃,反应时间为90s,反应结束后将反应液降温至室温,然后将反应液用水洗涤,减压蒸馏,得粗产品,粗产品用乙醇重结晶,得到所述3,5-二叔丁基-4-羟基苯甲酸正十六酯,收率为80.2%,反应结束后将反应液经过高效液相色谱分析其3,5-二叔丁基-4-羟基苯甲酸正十六酯的选择性为82.9%。
对比例3
本对比例提供一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法,包括如下步骤:
1)将1mol的3,5-二叔丁基-4-羟基苯甲酸、0.02mol的四甲基溴化铵和15mol的甲苯混合,配置得到3,5-二叔丁基-4-羟基苯甲酸溶液;
2)将1mol的正十六醇、0.02mol的4-磺酰杯[6]芳烃和15mol的甲苯混合,配置得到正十六醇溶液;
3)将3,5-二叔丁基-4-羟基苯甲酸溶液和正十六醇溶液加入到反应釜中100℃下反应6h,用HPLC法检测反应到达终点后将反应液降温至室温,然后将反应液用水洗涤,减压蒸馏,得粗产品,粗产品用乙醇重结晶,得到所述3,5-二叔丁基-4-羟基苯甲酸正十六酯,收率为75.7%,反应结束后将反应液经过高效液相色谱分析其3,5-二叔丁基-4-羟基苯甲酸正十六酯的选择性为81.0%。
显然,上述实施例仅仅是为清楚地说明所作的举例,而并非对实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。
Claims (10)
- 一种3,5-二叔丁基-4-羟基苯甲酸正十六酯的合成方法,其特征在于,包括如下步骤:1)将3,5-二叔丁基-4-羟基苯甲酸、四甲基溴化铵和甲苯混合,配置得到3,5-二叔丁基-4-羟基苯甲酸溶液;2)将正十六醇、4-磺酰杯[6]芳烃和甲苯混合,配置得到正十六醇溶液;3)将3,5-二叔丁基-4-羟基苯甲酸溶液和正十六醇溶液同时通入微通道反应器中进行反应,得到所述3,5-二叔丁基-4-羟基苯甲酸正十六酯。
- 根据权利要求1所述的合成方法,其特征在于,步骤1)中3,5-二叔丁基-4-羟基苯甲酸、四甲基溴化铵和甲苯的摩尔比为1:(0.01-0.03):(12-20)。
- 根据权利要求1或2所述的合成方法,其特征在于,步骤1)中3,5-二叔丁基-4-羟基苯甲酸、四甲基溴化铵和甲苯的摩尔比为1:(0.02-0.03):(15-20)。
- 根据权利要求1-3任一项所述的合成方法,其特征在于,步骤2)中正十六醇、4-磺酰杯[6]芳烃和甲苯的摩尔比为1:(0.01-0.03):(12-20)。
- 根据权利要求1-4任一项所述的合成方法,其特征在于,步骤3)所述微通道反应器中3,5-二叔丁基-4-羟基苯甲酸和正十六醇的摩尔比为1:(0.9-1.1)。
- 根据权利要求1-5任一项所述的合成方法,其特征在于,步骤3)中所述3,5-二叔丁基-4-羟基苯甲酸溶液的通入流速为18-22ml/min,所述正十六醇溶液的通入流速为18-22ml/min。
- 根据权利要求1-6任一项所述的合成方法,其特征在于,所述反应温度为55-65℃,反应时间为80-100s。
- 根据权利要求1-7任一项所述的合成方法,其特征在于,步骤3)中反应结束后还包括对反应液进行降温至室温、用水洗涤、减压蒸馏,得到粗产物的步骤。
- 根据权利要求8所述的合成方法,其特征在于,步骤3)中还包括对粗产物进行重结晶的步骤。
- 根据权利要求9所述的合成方法,其特征在于,采用乙醇对粗产物进行重结晶。
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CN105541613A (zh) * | 2015-12-31 | 2016-05-04 | 浙江师范大学 | 3,5-二叔丁基-4-羟基苯甲酸正十六烷基酯的制备方法 |
CN110845331A (zh) * | 2019-10-10 | 2020-02-28 | 天津利安隆新材料股份有限公司 | 一种苯甲酸高碳醇酯的制备方法 |
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US4528395A (en) * | 1983-08-15 | 1985-07-09 | American Cyanamid Co. | Process for esterifying 3,5-di-tert-butyl-4-hydroxybenzoic acid |
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WO2006054446A1 (ja) * | 2004-11-22 | 2006-05-26 | Adeka Corporation | ヒドロキシベンゾエート化合物の製造方法 |
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