CN1883790A - Process for reclaiming catalyst for use in synthesis of acesulfame potassium - Google Patents
Process for reclaiming catalyst for use in synthesis of acesulfame potassium Download PDFInfo
- Publication number
- CN1883790A CN1883790A CN 200610085795 CN200610085795A CN1883790A CN 1883790 A CN1883790 A CN 1883790A CN 200610085795 CN200610085795 CN 200610085795 CN 200610085795 A CN200610085795 A CN 200610085795A CN 1883790 A CN1883790 A CN 1883790A
- Authority
- CN
- China
- Prior art keywords
- triethylamine
- acesulfame potassium
- alkali
- recovering
- synthesizing
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000003054 catalyst Substances 0.000 title claims abstract description 13
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 title claims description 14
- 229960004998 acesulfame potassium Drugs 0.000 title claims description 14
- 235000010358 acesulfame potassium Nutrition 0.000 title claims description 14
- 239000000619 acesulfame-K Substances 0.000 title claims description 14
- 230000015572 biosynthetic process Effects 0.000 title claims 3
- 238000003786 synthesis reaction Methods 0.000 title claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 87
- 239000000203 mixture Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 11
- 150000001447 alkali salts Chemical class 0.000 claims abstract description 9
- 229910052602 gypsum Inorganic materials 0.000 claims abstract description 7
- 239000010440 gypsum Substances 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 5
- JNONJXMVMJSMTC-UHFFFAOYSA-N hydron;triethylazanium;sulfate Chemical compound OS(O)(=O)=O.CCN(CC)CC JNONJXMVMJSMTC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 4
- 239000003513 alkali Substances 0.000 claims description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000292 calcium oxide Substances 0.000 claims description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- FNXIDRUUVHQLHR-UHFFFAOYSA-N C(C)(=O)OS(=O)(C1=CC=C(C=C1)N)=O.[K] Chemical compound C(C)(=O)OS(=O)(C1=CC=C(C=C1)N)=O.[K] FNXIDRUUVHQLHR-UHFFFAOYSA-N 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000011109 contamination Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 230000000630 rising effect Effects 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229960005164 acesulfame Drugs 0.000 description 1
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- DMZUSFYWKZBCEV-UHFFFAOYSA-N n,n-diethylethanamine;3-oxobutanoylsulfamic acid Chemical compound CC[NH+](CC)CC.CC(=O)CC(=O)NS([O-])(=O)=O DMZUSFYWKZBCEV-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a process for recovering catalyst in synthesizing potassium acetylsulfanilate, which includes steps of: (1) neutralizing mixture containing triethylamine sulphate with base or basic salt, rising the temperature to 70-120 DEG C for distilling triethylamine. (2) removing water of triethylamine received in step (1) to obtain high purity triethylamine. In addition, acid could be added to the mixture of removing triethylamine in step (1) to neutralizing excess base, and gypsum is obtained by filtrating reactive liquid. The excellence of this method is that the process is simple, processing time is short, damage to the device is slight, having no contamination to environment, the retrieving triethylamine have high purity and can be used for synthesizing potassium acetylsulfanilate after removing water, and the byproduct such as gypsum also has some economic benefit
Description
Technical Field
The invention relates to a process for recovering triethylamine from a mixture generated in the process of synthesizing acesulfame potassium by taking triethylamine as a catalyst.
Background
Acesulfame potassium is a sweetener widely used in food and beverage industries. The compound has the advantages of good water solubility, high sweetness, stable physicochemical property, strong synergistic effect, non-metabolic property and the like.
The method for synthesizing the acesulfame potassium is various. The synthesis method of acesulfame potassium related by the invention is the US patent with the patent number US4,695,629 which is expired in 3 months in 2005, and the synthesis method is as follows: reacting sulfamic acid with diketene under the catalysis of triethylamine to generate acetoacetamidosulfonic acid triethylamine salt, then carrying out ring closure by using sulfur trioxide to prepare acesulfame, and then reacting with potassium hydroxide to prepare acesulfame potassium. In the introduction, triethylamine is used as a catalyst to synthesize the acesulfame potassium, and other related data are as follows: as in US patent nos. US4,695,629 and US5,011,982 and US5,103,046, no relevant process for recovering triethylamine as a catalyst has been found. According to research, an acidic mixture is generated in the process of synthesizing the acesulfame potassium by using triethylamine as a catalyst, the acidic mixture contains sulfuric acid and triethylamine sulfate, and the triethylamine recovered from the acidic mixture has certain economic value.
Disclosure of Invention
Aiming at the problems, the invention provides a process for recovering triethylamine from a mixture generated in the process of synthesizing potassium acetylsulfanilate by taking triethylamine as a catalyst.
In order to realize the purpose, the invention adopts the following specific process steps: firstly, neutralizing a mixture containing triethylamine sulfate by using alkali or basic salt, and heating to 70-120 ℃ to distill triethylamine. In this process, the amount of the base or basic salt to be added can be controlled with the aim of substantially distilling off triethylamine. And (II) removing water from the triethylamine obtained in the step (I) to obtain high-purity triethylamine.
The alkali or alkali salt used in the step (one) is selected from one of sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, calcium carbonate and alkali prepared from oxide or a mixture of several of the alkali prepared from oxide and non-reactive with each other. The base prepared from the oxides described above may be: calcium hydroxide is prepared by reacting calcium oxide with water.
The further technical scheme of the invention is as follows: and (2) adding acid into the mixture obtained in the step (I) after the triethylamine is distilled off to neutralize excessive alkali, and filtering the reaction solution after the reaction is finished to obtain gypsum. And, the acid used may be sulfuric acid.
The invention has the advantages that: the process is simple, convenient and feasible to operate, short in treatment time, less in damage to equipment and free of pollution to the environment. The recovered triethylamine has high purity, and can be used for synthesizing potassium acetylsulfanilate after water is removed. In addition, the quality of the byproduct gypsum reaches the national standard, and the gypsum can be used for firing baking-free bricks and the like, and can bring certain economic benefit.
Detailed Description
The invention is further described below by means of specific examples; the invention should not be limited to this embodiment.
Examples
Firstly, 40.0g of calcium oxide and 70.0g of water are added into a 500ml three-necked reaction bottle with a stirring and temperature measuring device and a distilling device, 330.0g of triethylamine sulfate-containing mixture (containing 5 percent of triethylamine and 27.85 percent of sulfuric acid) is dropwise added while stirring, the temperature of a reaction system is raised to 70-120 ℃, and distillation is carried out for 150 minutes. 16.5g of triethylamine are obtained, containing 65.33% o of water. The reaction equation is as follows:
(II) adding 22g of concentrated sulfuric acid dropwise to the mixture obtained in the step (I) except for the triethylamine while stirring, and after completion of the reaction, filtering the reaction mixture to obtain 233.0g of gypsum (containing 10% of water). The reaction equation is as follows:
and thirdly, adding the triethylamine obtained in the step one and 3.5g of calcium oxide into a three-neck flask provided with a reflux condenser and a thermometer. The upper opening of the condensing pipe is provided with an anhydrous calcium chloride drying pipe communicated with the atmosphere. Heated to reflux for 1 hour. The reflux condenser tube was removed and directly distilled to yield 14.9g triethylamine containing 0.5% o water. The content was 99.84% by gas chromatography (FID). The yield was about 90.3%.
Claims (5)
1. A process for recovering a catalyst used in the process of synthesizing acesulfame potassium is characterized in that: the method comprises the following steps:
firstly, neutralizing a mixture containing triethylamine sulfate by using alkali or basic salt, and heating to 70-120 ℃ to distill triethylamine.
And (II) removing water from the triethylamine obtained in the step (I) to obtain high-purity triethylamine.
2. The process for recovering the catalyst used in the process of synthesizing acesulfame potassium according to claim 1, wherein: the alkali or basic salt used in the step (one) is selected from one of sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, calcium carbonate and alkali prepared from oxide or a mixture of several of the alkali prepared from oxide and non-reactive with each other.
3. The process for recovering the catalyst used in the synthesis of acesulfame potassium according to claim 2, wherein: the alkali prepared from the oxides is as follows: calcium hydroxide is prepared by reacting calcium oxide with water.
4. The process for recovering the catalyst used in the processof synthesizing acesulfame potassium according to claim 1, wherein: and (2) adding acid into the mixture obtained in the step (I) after the triethylamine is distilled off to neutralize excessive alkali, and filtering the reaction solution after the reaction is finished to obtain gypsum.
5. The process for recovering the catalyst used in the synthesis of acesulfame potassium according to claim 4, wherein: the acid used is sulfuric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610085795 CN1883790A (en) | 2006-06-30 | 2006-06-30 | Process for reclaiming catalyst for use in synthesis of acesulfame potassium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610085795 CN1883790A (en) | 2006-06-30 | 2006-06-30 | Process for reclaiming catalyst for use in synthesis of acesulfame potassium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1883790A true CN1883790A (en) | 2006-12-27 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200610085795 Pending CN1883790A (en) | 2006-06-30 | 2006-06-30 | Process for reclaiming catalyst for use in synthesis of acesulfame potassium |
Country Status (1)
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Cited By (16)
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|---|---|---|---|---|
| CN102040522A (en) * | 2010-12-14 | 2011-05-04 | 青岛瀚生生物科技股份有限公司 | Method for recycling triethylamine from production of propargite |
| CN102079712A (en) * | 2010-12-31 | 2011-06-01 | 大连联化化学有限公司 | Method for recycling anhydrous organic amine from organic amine salt |
| EP2380870A1 (en) | 2010-04-19 | 2011-10-26 | Celanese International Corporation | Method to recover organic tertiary amines from waste sulfuric acid employing a plug flow reactor |
| EP2380869A1 (en) | 2010-04-19 | 2011-10-26 | Celanese International Corporation | Method to recover organic tertiary amines from waste sulfuric acid |
| WO2011133467A1 (en) | 2010-04-19 | 2011-10-27 | Celanese International Corporation | Process for producing ammonium salts |
| CN102834352A (en) * | 2010-04-19 | 2012-12-19 | 国际人造丝公司 | Method for the manufacture of ammonium sulfate composition |
| WO2013096152A1 (en) | 2011-12-21 | 2013-06-27 | Celanese International Corporation | Process for producing ammonium salts |
| CN104193625A (en) * | 2014-09-27 | 2014-12-10 | 安徽金禾实业股份有限公司 | Recovery method of catalyst triethylamine in acesulfame potassium production |
| US9024016B2 (en) | 2012-06-08 | 2015-05-05 | Nutrinova Nutrition Specialists & Food Ingredients GmbH | Process for producing acesulfame potassium |
| CN105111088A (en) * | 2015-09-02 | 2015-12-02 | 江苏瑞克医药科技有限公司 | Method for recycling triethylamine from wastewater containing triethylamine hydrochloride |
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| US10030000B2 (en) | 2016-09-21 | 2018-07-24 | Celanese International Corporation | Acesulfame potassium compositions and processes for producing same |
| US10029999B2 (en) | 2016-09-21 | 2018-07-24 | Celanese International Corporation | Acesulfame potassium compositions and processes for producing same |
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2006
- 2006-06-30 CN CN 200610085795 patent/CN1883790A/en active Pending
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| CN102834352A (en) * | 2010-04-19 | 2012-12-19 | 国际人造丝公司 | Method for the manufacture of ammonium sulfate composition |
| EP2380870A1 (en) | 2010-04-19 | 2011-10-26 | Celanese International Corporation | Method to recover organic tertiary amines from waste sulfuric acid employing a plug flow reactor |
| EP2380869A1 (en) | 2010-04-19 | 2011-10-26 | Celanese International Corporation | Method to recover organic tertiary amines from waste sulfuric acid |
| WO2011131531A1 (en) | 2010-04-19 | 2011-10-27 | Celanese International Corporation | Method to recover organic tertiary amines from waste sulfuric acid employing a plug flow reactor |
| WO2011131530A1 (en) | 2010-04-19 | 2011-10-27 | Celanese International Corporation | Method to recover organic tertiary amines from waste sulfuric acid |
| US8658830B2 (en) | 2010-04-19 | 2014-02-25 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Method to recover organic tertiary amines from waste sulfuric acid |
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| US8496905B2 (en) | 2010-04-19 | 2013-07-30 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Method for the manufacture of an ammonium sulfate composition |
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| CN102040522A (en) * | 2010-12-14 | 2011-05-04 | 青岛瀚生生物科技股份有限公司 | Method for recycling triethylamine from production of propargite |
| CN102079712A (en) * | 2010-12-31 | 2011-06-01 | 大连联化化学有限公司 | Method for recycling anhydrous organic amine from organic amine salt |
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