WO2022246870A1 - Procédé de préparation d'un sel de triéthylamine d'acide acétoacétamide-n-sulfonique - Google Patents

Procédé de préparation d'un sel de triéthylamine d'acide acétoacétamide-n-sulfonique Download PDF

Info

Publication number
WO2022246870A1
WO2022246870A1 PCT/CN2021/097018 CN2021097018W WO2022246870A1 WO 2022246870 A1 WO2022246870 A1 WO 2022246870A1 CN 2021097018 W CN2021097018 W CN 2021097018W WO 2022246870 A1 WO2022246870 A1 WO 2022246870A1
Authority
WO
WIPO (PCT)
Prior art keywords
reaction
dichloromethane
solution
sulfamic acid
triethylamine
Prior art date
Application number
PCT/CN2021/097018
Other languages
English (en)
Chinese (zh)
Inventor
周睿
丁震
陈永旭
杨峰宝
刘刚
Original Assignee
安徽金禾实业股份有限公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 安徽金禾实业股份有限公司 filed Critical 安徽金禾实业股份有限公司
Priority to CN202180001407.4A priority Critical patent/CN113454060B/zh
Priority to PCT/CN2021/097018 priority patent/WO2022246870A1/fr
Publication of WO2022246870A1 publication Critical patent/WO2022246870A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/34—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B21/00—Nitrogen; Compounds thereof
    • C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
    • C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
    • C01B21/093—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more sulfur atoms
    • C01B21/096—Amidosulfonic acid; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/03—Monoamines
    • C07C211/05—Mono-, di- or tri-ethylamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids

Definitions

  • the invention belongs to the technical field of fine chemicals, and in particular relates to a preparation method of acetoacetamide-N-sulfonic acid triethylamine salt.
  • Acesulfame potassium also known as AK sugar
  • AK sugar is a widely used sugar substitute food additive. Its appearance is white crystalline powder.
  • As an organic synthetic salt its taste is similar to sugarcane, and it is easily soluble in water. , Slightly soluble in alcohol, its chemical properties are stable, and it is not easy to break down and fail; it does not participate in the body's metabolism and does not provide energy; it has high sweetness and low price; it has no cariogenicity; it has good stability to heat and acid.
  • Acetoacetamide-N-sulfonic acid triethylamine salt is the important intermediate of producing acesulfame potassium, and the preparation method of this intermediate generally adopts diketene-sulfur trioxide method, and its specific reaction steps comprise: 1) making sulfamic acid Reaction with an amine to form the amine sulfamate salt, which is then reacted with diketene to form the acetoacetamide-N-sulfonic acid triethylamine salt.
  • the above reaction uses common sulfamic acid, diketene, triethylamine, etc. as raw materials.
  • the reaction conditions are mild, the product yield is high, and the product purity is high. It is a relatively common industrialized method.
  • acylation reaction between sulfamic acid amine salt and diketene is a strong exothermic reaction, diketene has a low flash point, and high-concentration diketene is prone to accidents at high temperatures.
  • the addition acylation reaction must be carried out under strict temperature control conditions.
  • the reaction speed is slow, the reaction time is prolonged, and ice water cooling is required during the reaction process, which increases the reaction cost; the reaction requires a specific device, and the device cost and device maintenance cost are high; large-scale reactions cannot be completed in time and are not suitable for industrialization Continuous production.
  • acetic acid needs to be added as a catalyst in the reaction process, which makes acetic acid impurities remain in the final product acesulfame potassium, resulting in poor color of acesulfame potassium and affecting people's experience in use.
  • the present application is proposed to provide a method for preparing acetoacetamide-N-sulfonic acid triethylamine salt that overcomes the above problems or at least partially solves the above problems.
  • a kind of preparation method of acetoacetamide-N-sulfonic acid triethylamine salt comprises:
  • Amination reaction steps dissolving sulfamic acid in the first dichloromethane to configure the first reaction solution; dissolving triethylamine in the second dichloromethane to configure the second reaction solution, adding the second reaction solution to Amination reaction is carried out in the first reaction solution to form ammonium sulfamate solution; and
  • Acylation reaction steps dissolving diketene in the third dichloromethane to configure the third reaction solution; filling the solid-state heteropolyacid catalyst in the fixed-bed reactor, and feeding the ammonium sulfamate solution and The third reaction liquid reacts under preset conditions to form acetoacetamide-N-sulfonic acid triethylamine salt solution.
  • the ratio of the molar amount of sulfamic acid to the molar amount of the first dichloromethane is 1:6-15; the dissolution of sulfamic acid The temperature is 20-25°C.
  • the ratio of the molar amount of triethylamine to the molar amount of the second dichloromethane is 1:1.5-2.5; -20 °C soluble in the second dichloromethane.
  • the ratio of the mass consumption of sulfamic acid to the mass consumption of triethylamine is 1:1-1.2; the reaction temperature of the amination reaction is 20-30°C.
  • the ratio of the molar amount of diketene to the third dichloromethane is 1:1.5-2.5;
  • Diketene is soluble in tertiary dichloromethane at 10-20°C.
  • the ratio of the molar amount of sulfamic acid to the molar amount of diketene is 1:1-1.2, preferably 1:1.02-1.1.
  • the preset conditions are: the temperature is set to 20-35°C, preferably 25-30°C; the reaction time is set to 10-120s, preferably 30s -120s.
  • the solid heteropolyacid catalyst is a Keggin-type solid heteropolyacid catalyst.
  • the solid heteropolyacid catalyst with Keggin structure is H 3 [PMo 12 O 14 ] ⁇ xH 2 O solid catalyst.
  • acetoacetamide-N-sulfonic acid triethylamine salt which is prepared by any of the methods described above.
  • the beneficial effect of the present application is that the present application simplifies the product post-treatment process on the one hand by using a solid heteropolyacid catalyst combined with a fixed-bed reactor to replace the traditional organic acid catalyst combined with a reaction tank, so that the final product acesulfame K
  • the appearance of the product is better, which significantly improves the user experience; on the other hand, the large-scale continuous production of acetoacetamide-N-sulfonic acid triethylamine salt has been realized, which greatly shortens the reaction time and improves the reaction yield. Therefore, the production cost of acesulfame potassium is reduced.
  • the intermediate acetoacetamide-N-sulfonic acid triethylamine salt for the preparation of acesulfame potassium has long reaction time, low reaction efficiency, low product yield, and difficulty in controlling the reaction temperature.
  • the problem of providing a kind of preparation method of acetoacetamide-N-sulfonic acid triethylamine salt, is used for producing acetoacetamide-N-sulfonic acid triethylamine salt by combining a solid zeolite catalyst with a fixed bed reactor can effectively overcome the above problems, realize continuous large-scale production, shorten the reaction time, and improve production efficiency.
  • the preparation method of acetoacetamide-N-sulfonic acid triethylamine salt of the present application comprises:
  • Amination reaction steps dissolving sulfamic acid in the first dichloromethane to configure the first reaction solution; dissolving triethylamine in the second dichloromethane to configure the second reaction solution, adding the second reaction solution to Amination reaction is carried out in the first reaction solution to form ammonium sulfamate solution.
  • the first reaction solution and the second reaction solution obtained by dissolving sulfamic acid and triethylamine in dichloromethane respectively are subjected to an amination reaction to obtain a sulfamic acid ammonium salt solution.
  • the second reaction liquid is added dropwise into the first reaction liquid.
  • the pH value is 7-9, and the reaction is left to stand for 1 hour.
  • the above-mentioned reacted material is ammonium sulfamate solution.
  • dichloromethane by mixing dichloromethane with raw material sulfamic acid and triethylamine respectively, and then reacting with diketene dissolved in dichloromethane, dichloromethane can take away a large amount of heat of reaction on the one hand, It makes temperature control easier; on the other hand, it can increase the flash point of diketene and increase the reaction temperature of the entire reaction.
  • acylation reaction step dissolve diketene in the third methylene chloride to configure the third reaction solution; fill the solid-state heteropolyacid catalyst in the fixed-bed reactor, and feed the ammonium sulfamate solution into the fixed-bed reactor in turn React with the third reaction solution under preset conditions to form acetoacetamide-N-sulfonic acid triethylamine salt solution.
  • a class of heteropolyacid catalyst contains the catalyzer of the polynuclear coordination compound of oxygen bridge, there is certain gap between the heteropolyions in the bulk phase of solid-state heteropolyacid catalyst, makes Some molecules can go in and out, so that the solid heteropolyacid can successfully complete the catalytic process.
  • a solid heteropolyacid catalyst is used to replace the traditional acetic acid catalyst to provide acidic sites for the acylation reaction.
  • it can effectively catalyze the acylation reaction of ammonium sulfamate and diketene.
  • the heteropolyacid catalyst will not be mixed into the reaction product, and no special treatment process is required in the follow-up, which saves post-treatment economy and time cost; and avoids the acetic acid impurity that is not removed in the prior art remaining in the final product and affecting the final product. Adverse effects caused by appearance.
  • This application also adopts a fixed-bed reactor.
  • the type and specification of the fixed-bed reactor are not limited.
  • anyone who can realize the fixation of the solid-state heteropolyacid catalyst does not need to provide a liquid acidic environment and does not introduce Impurities are sufficient, such as tubular fixed-bed reactors.
  • the beneficial effect of the present application is that the present application simplifies the product post-treatment process on the one hand by using a solid heteropolyacid catalyst combined with a fixed-bed reactor to replace the traditional organic acid catalyst combined with a reaction tank, so that the final product acesulfame K
  • the appearance of the product is better, which significantly improves the user experience; on the other hand, the large-scale continuous production of acetoacetamide-N-sulfonic acid triethylamine salt has been realized, which greatly shortens the reaction time and improves the reaction yield. Therefore, the production cost of acesulfame potassium is reduced.
  • the type of heteropolyacid catalyst is not limited, any solid heteropolyacid catalyst that can provide acid sites can be; in some embodiments of the application, the solid heteropolyacid catalyst is Keggin type structure Solid-state heteropolyacid catalysts, mainly Keggin-type structures of 1:12 series such as H 3 [PMO 12 O 14 ] ⁇ xH 2 O, which have strong acidity and oxidizing properties, and their acidity is usually higher than that of each group of heteropolyacids The oxyacids contained in it have strong acidity, and when used as an oxidizing agent, it is easy to oxidize other substances, making itself in a reduced state and easy to regenerate.
  • the solid heteropolyacid catalyst is Keggin type structure Solid-state heteropolyacid catalysts, mainly Keggin-type structures of 1:12 series such as H 3 [PMO 12 O 14 ] ⁇ xH 2 O, which have strong acidity and oxidizing properties, and their acidity is usually higher than that of each group of heteropolya
  • the heteropolyacid catalyst can effectively catalyze the acylation of ammonium sulfamate and diketene on the one hand.
  • the smooth progress of the reaction significantly reduces the cost of the catalyst due to its strong regeneration ability, and further reduces the production cost of acesulfame potassium.
  • the ratio of the amount of sulfamic acid to the first dichloromethane is not limited, as long as the complete dissolution of sulfamic acid is ensured; in some embodiments of the present application Among them, considering economic factors, the ratio of the molar dosage of sulfamic acid to the molar dosage of the first dichloromethane is 1:6-15.
  • the dissolution temperature of sulfamic acid in the first dichloromethane is 20-25°C, that is, at room temperature. If the temperature is lower than 20°C or higher than 25°C, it only needs to be realized by specific means, although it is possible to achieve more Rapid dissolution, but requires a high economic cost, because the sulfamic acid is not difficult to dissolve, so it can be at room temperature.
  • the ratio of the amount of triethylamine to the second dichloromethane is not limited, as long as the complete dissolution of triethylamine is ensured; in this application Considering economical factors in some embodiments of the application, in the amination reaction step, the ratio of the molar usage of triethylamine to the molar usage of the second dichloromethane is 1:1.5-2.5.
  • the temperature at which triethylamine is dissolved in the second dichloromethane can be set at 10-20°C. Under low temperature conditions, it is beneficial to dissipate heat during the dissolution process.
  • the ratio of the amount of sulfamic acid to triethylamine is not limited, and prior art can be referred to.
  • the ratio of the mass usage of sulfamic acid to the mass usage of triethylamine is 1:1-1.2.
  • the temperature of the amination reaction since the amination reaction does not need heating or cooling, it can be carried out at room temperature, and in some embodiments of the present application, it can be 20-30°C.
  • the ratio of the molar amount of diketene to the molar amount of the third dichloromethane is 1:1.5-2.5.
  • the temperature at which diketene is dissolved in the third dichloromethane can be set at 10-20°C. Under low temperature conditions, it is beneficial to dissipate heat during the dissolution process.
  • the ratio of the amount of sulfamic acid to triethylamine is not limited, and prior art can be referred to, such as in Chinese patent document CN112142687A, sulfamic acid and triethylamine
  • n(sulfamic acid) of diketene:n(diketene) 1:1.0-1.5.
  • diketene needs a large amount of excess to achieve better technical results.
  • sulfamic acid and diketene have greater contact area, to obtain a better mixing effect, so that the upper limit of the amount of diketene can be reduced relative to the prior art.
  • the ratio is 1:1-1.2, and in other embodiments is 1:1.02-1.1, which can achieve better technical effects.
  • the preset conditions in the acylation reaction step there is no limit to the preset conditions in the acylation reaction step, as long as there is no danger and can meet the reaction requirements of ammonium sulfamate solution and diketene; in some embodiments of the application , in the acylation reaction step, the preset conditions are: the temperature is set at 20-35°C; the reaction time is set at 10-120s. That is to say, the acylation reaction step of the present application is preferably carried out at a lower temperature, because dichloromethane can take away a large amount of heat, therefore, in the present application, temperature control is easier to achieve, using the prior art Any one of them can be used, such as air condensation technology, circulating water condensation technology and heat exchange plate.
  • the reaction time of the acylation step can be significantly shortened, and the reaction can be completely completed within 10-120 seconds. If the reaction temperature is lower than 20°C and the reaction time is shorter than 10s, the reaction conditions are difficult to control, resulting in high reaction costs, too short contact time of raw materials, and incomplete reaction; if the reaction temperature is higher than 35°C and the reaction time is longer than 120s, then If the reaction temperature is too high, it is prone to danger, and the reaction time is too long, which increases the time cost and has no other beneficial effects; in other embodiments of the present application, in the acylation reaction step, the preset condition can preferably be: temperature Set it to 25-30°C; set the reaction time to 30-120s.
  • each drug or reagent can be made by a laboratory or factory, or a commercially available product, which is not limited in this application.
  • Example 1 (including Example 1A, Example 1B, Example 1C, Example 1D, Example 1E)
  • Amination reaction steps Dissolve 98kg of sulfamic acid and the first dichloromethane at a molar ratio of 1:6, and control the dissolution temperature at about 20-25°C to obtain a dichloromethane solution of sulfamic acid, that is, the first The reaction solution.
  • Dissolution can be in a continuous mixing device or in a reactor.
  • Embodiment 1A, embodiment 1B, embodiment 1C, embodiment 1D, embodiment 1E all comprise amination reaction step, in this reaction step, between each embodiment, the mass ratio of sulfamic acid and triethylamine changes, Please see Table 1 for details.
  • Acylation reaction step dissolving diketene and third dichloromethane at a molar ratio of 1:1.5, controlling the dissolution temperature to 10-20° C. to obtain a third reaction solution.
  • the fixed bed reactor After the solid heteropolyacid catalyst is installed in the fixed bed reactor, the fixed bed reactor is started, and the circulating water is adjusted to make the circulating water work normally.
  • Embodiment 1A, embodiment 1B, embodiment 1C, embodiment 1D, embodiment 1E all comprise acylation reaction step, in this reaction step, between each embodiment, the molar ratio of sulfamic acid and diketene and reaction conditions exist change , see Table 1 for details.
  • Comparative Example 1 (comprising Comparative Example 1A and Comparative Example 1B)
  • Amination reaction step 98kg of sulfamic acid and triethylamine are mixed and stirred in a reaction kettle with a mass ratio of 1:1, and the control system is weakly alkaline. After mixing evenly, the ammonium sulfamic acid solution is obtained.
  • the configuration of the dichloromethane solution of diketene dissolve diketene and dichloromethane at a molar ratio of 1:8, and form the dichloromethane solution of diketene to form the third reaction solution.
  • Comparative Example 2 (comprising Comparative Example 2A, Comparative Example 2B, Comparative Example 2C, Comparative Example 2D and Comparative Example 2E)
  • Amination reaction steps 98kg of sulfamic acid and the first dichloromethane are dissolved in a molar ratio of 1:15, and the temperature of dissolution is controlled to be about 20-25°C to obtain the dichloromethane solution of sulfamic acid as the first reaction liquid.
  • Dissolution can be in a continuous mixing device or in a reactor.
  • Comparative Example 2A, Comparative Example 2B, Comparative Example 2C, Comparative Example 2D and Comparative Example 2E all comprise an amination reaction step, and in this reaction step, between each embodiment, the mass ratio of sulfamic acid and triethylamine varies, Please see Table 1 for details.
  • Acylation reaction step adopt fixed-bed reactor, but do not use solid-state heteropolyacid molecular sieve.
  • Diketene and third dichloromethane were dissolved at a molar ratio of 1:2.0, and the temperature of dissolution was controlled to be 10-20°C to obtain a third reaction solution.
  • the sulfamic acid ammonium salt solution after adding acetic acid is passed in the fixed-bed reactor, controls the flow velocity of the sulfamic acid ammonium salt solution;
  • the 3rd reaction liquid is passed in the fixed-bed reactor, controls the 3rd reaction liquid flow velocity; After the reaction starts, lower the temperature of the cooling water as much as possible, and control the temperature of the reaction system between 20-35°C; as the activity of the zeolite molecular sieve decreases, the temperature rises slightly within the control range.
  • the yield is based on sulfamic acid, and the calculation method of the yield is the percentage of the mass of the target product acetoacetamide-N-sulfonic acid triethylamine salt to the mass of sulfamic acid.
  • the solid-state heteropolyacid molecular sieve of Example 1 in the fixed-bed reactor, the reaction can be completed quickly, and the advantage of completing the reaction quickly is that under the same production capacity, a relatively small amount of diketene can be added at a time It can meet the needs of subsequent production. From the reaction point of view, the whole reaction time should not be too long, and the longer maintenance time will cause the decline of the overall yield.
  • Example 1 the yield of the reaction in Example 1 is higher than that of Comparative Example 2 using acetic acid, and the reaction speed is obviously accelerated.
  • the amount of triethylamine shows that in the present application, under the condition of using a solid heteropolyacid catalyst, a higher yield can be obtained without a slight excess of amine.
  • the present application has short reaction time, low requirements on equipment, is suitable for industrial production, has high overall product yield, approximate molar ratio of raw materials, and less subsequent organic waste.
  • this application simplifies the post-treatment process of the product on the one hand by using a solid heteropolyacid catalyst combined with a fixed-bed reactor to replace the traditional organic acid catalyst combined with a reaction tank. Better, it significantly improves the user experience; on the other hand, it realizes the large-scale continuous production of acetoacetamide-N-sulfonic acid triethylamine salt, which greatly shortens the reaction time and improves the reaction yield. Further, Reduced the production cost of acesulfame potassium.

Landscapes

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

Abstract

L'invention concerne un procédé de préparation d'un sel de triéthylamine d'acide acétoacétamide-N-sulfonique, le procédé comprenant : une étape de réaction d'amination, consistant à : dissoudre de l'acide sulfamique dans un premier dichlorométhane pour obtenir une première solution de réaction ; dissoudre de la triéthylamine dans un deuxième dichlorométhane pour obtenir une deuxième solution de réaction, et ajouter la deuxième solution de réaction à la première solution de réaction pour une réaction d'amination afin de former une solution de sulfamate d'ammonium ; et une étape de réaction d'acylation, consistant à : dissoudre du dicétène dans un troisième dichlorométhane pour préparer une troisième solution de réaction ; remplir un réacteur à lit fixe avec un catalyseur hétéropolyacide solide, introduire séquentiellement la solution de sulfamate d'ammonium et la troisième solution de réaction dans le réacteur à lit fixe et les faire réagir dans des conditions préétablies pour former le sel de triéthylamine d'acide acétoacétamide-N-sulfonique. Le procédé selon l'invention permet de simplifier le procédé de post-traitement pour le produit, de telle sorte que le produit final de potassium d'acésulfame présente un meilleur aspect ; permet d'obtenir une production continue à grande échelle du sel de triéthylamine d'acide acétoacétamide-N-sulfonique, de raccourcir le temps de réaction, d'augmenter le rendement de la réaction, et de réduire le coût de production de l'acésulfame potassique.
PCT/CN2021/097018 2021-05-28 2021-05-28 Procédé de préparation d'un sel de triéthylamine d'acide acétoacétamide-n-sulfonique WO2022246870A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202180001407.4A CN113454060B (zh) 2021-05-28 2021-05-28 乙酰乙酰胺-n-磺酸三乙胺盐的制备方法
PCT/CN2021/097018 WO2022246870A1 (fr) 2021-05-28 2021-05-28 Procédé de préparation d'un sel de triéthylamine d'acide acétoacétamide-n-sulfonique

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2021/097018 WO2022246870A1 (fr) 2021-05-28 2021-05-28 Procédé de préparation d'un sel de triéthylamine d'acide acétoacétamide-n-sulfonique

Publications (1)

Publication Number Publication Date
WO2022246870A1 true WO2022246870A1 (fr) 2022-12-01

Family

ID=77819483

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2021/097018 WO2022246870A1 (fr) 2021-05-28 2021-05-28 Procédé de préparation d'un sel de triéthylamine d'acide acétoacétamide-n-sulfonique

Country Status (2)

Country Link
CN (1) CN113454060B (fr)
WO (1) WO2022246870A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103570592A (zh) * 2013-11-01 2014-02-12 安徽金禾实业股份有限公司 安赛蜜合成酰化生产工艺
CN105198778A (zh) * 2015-08-28 2015-12-30 安徽金禾实业股份有限公司 一种安赛蜜合成工段酰化反应工艺
CN108822004A (zh) * 2018-08-30 2018-11-16 东营市科维生物技术有限公司 连续生产安赛蜜中间体的管式反应合成方法和装置
CN108884064A (zh) * 2016-09-21 2018-11-23 国际人造丝公司 乙酰舒泛钾组合物和其生产方法
CN111377834A (zh) * 2018-12-30 2020-07-07 南通醋酸化工股份有限公司 一种乙酰乙酰胺基磺酸三乙胺的连续制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3410439A1 (de) * 1984-03-22 1985-09-26 Hoechst Ag, 6230 Frankfurt Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzen sowie der dabei als zwischenprodukt(e) auftretenden acetoacetamind-n-sulfonsaeure(salze)
CN1026106C (zh) * 1985-06-05 1994-10-05 赫彻斯特股份公司 一种制备乙酰乙酰胺-n-磺酸(盐)的方法
US9024016B2 (en) * 2012-06-08 2015-05-05 Nutrinova Nutrition Specialists & Food Ingredients GmbH Process for producing acesulfame potassium
EP2995607A1 (fr) * 2014-09-10 2016-03-16 Taminco bvba Amination directe d'alcools avec des hétéropolyacides
CN111377882B (zh) * 2018-12-30 2022-03-22 南通醋酸化工股份有限公司 一种连续化生产安赛蜜的方法
CN110256272A (zh) * 2019-06-29 2019-09-20 濮阳天源生物科技有限公司 利用固体酸催化剂合成酰胺类凉味剂的方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103570592A (zh) * 2013-11-01 2014-02-12 安徽金禾实业股份有限公司 安赛蜜合成酰化生产工艺
CN105198778A (zh) * 2015-08-28 2015-12-30 安徽金禾实业股份有限公司 一种安赛蜜合成工段酰化反应工艺
CN108884064A (zh) * 2016-09-21 2018-11-23 国际人造丝公司 乙酰舒泛钾组合物和其生产方法
CN108822004A (zh) * 2018-08-30 2018-11-16 东营市科维生物技术有限公司 连续生产安赛蜜中间体的管式反应合成方法和装置
CN111377834A (zh) * 2018-12-30 2020-07-07 南通醋酸化工股份有限公司 一种乙酰乙酰胺基磺酸三乙胺的连续制备方法

Also Published As

Publication number Publication date
CN113454060A (zh) 2021-09-28
CN113454060B (zh) 2022-11-25

Similar Documents

Publication Publication Date Title
WO2022246871A1 (fr) Procédé de préparation d'un sel de triéthylamine d'acide acétoacétamide-n-sulfonique
KR101348524B1 (ko) 메타텅스텐산 암모늄 제조방법
CN107382844A (zh) 一种以烟酸胺为原料生产烟酸的方法
CN102321028A (zh) 一种合成2-甲基-5-硝基咪唑-1-乙醇的方法
CN109678727A (zh) 一种微通道硝化反应合成2-乙基-5-硝基苯胺的方法
CN105085411A (zh) 一种6-羟基-2,4,5-三氨基嘧啶硫酸盐的制备方法
CN100361964C (zh) 盐酸加巴喷丁及其中间体的制备方法
CN106565616A (zh) 一种抗菌兽药磺胺间甲氧嘧啶钠的制备方法
CN113200862B (zh) 一种对硝基苯酚钠的合成工艺
WO2022246867A1 (fr) Procédé de préparation d'acésulfame de potassium
CN102875435B (zh) 一种有机硫代硫酸衍生物的制备方法
CN104262215A (zh) 一种2-硝基-4-甲砜基苯甲酸的制备方法
WO2022246870A1 (fr) Procédé de préparation d'un sel de triéthylamine d'acide acétoacétamide-n-sulfonique
US20240083862A1 (en) Method for preparing acesulfame potassium
CN103693673B (zh) 一种利用酸性含铜蚀刻废液生产电镀级硫酸铜的生产方法
CN108341788A (zh) 一种枸橼酸莫沙必利中间体及用途
CN110746326A (zh) 一种连续化生产羟乙基磺酸的方法
CN101723842B (zh) 乙二胺四乙酸二钠盐的制备方法
CN108912019A (zh) 一种从d，l-苏式-对甲砜基苯丝氨酸乙酯母液中回收铜盐及乙醇的方法
CN107311950A (zh) 一种氰尿酸镧的制备方法
CN107522638A (zh) 制备邻甲酸甲酯苯磺酰胺的微反应器和方法
WO2022246862A1 (fr) Composition d'acétylsulfonate de potassium
CN108707108A (zh) 一种4,4`-（2-吡啶亚甲基）二苯酚双醋酸酯合成方法
CN112538018B (zh) 一种连续流区域选择性合成3-硝基水杨酸的方法
WO2022246865A1 (fr) Procédé de préparation de potassium d'acésulfame

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21942441

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21942441

Country of ref document: EP

Kind code of ref document: A1