CN113248452A - 一种生产三羟乙基异氰尿酸酯的方法 - Google Patents
一种生产三羟乙基异氰尿酸酯的方法 Download PDFInfo
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- CN113248452A CN113248452A CN202110394863.1A CN202110394863A CN113248452A CN 113248452 A CN113248452 A CN 113248452A CN 202110394863 A CN202110394863 A CN 202110394863A CN 113248452 A CN113248452 A CN 113248452A
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- -1 trihydroxyethyl isocyanurate Chemical compound 0.000 title claims abstract description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 238000007259 addition reaction Methods 0.000 claims abstract description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000011949 solid catalyst Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0237—Amines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0239—Quaternary ammonium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/19—Catalysts containing parts with different compositions
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
一种生产三羟乙基异氰尿酸酯的方法，属于化工合成技术领域，氰尿酸与环氧乙烷在催化剂的催化作用下在有机溶剂中进行加成反应，反应结束后将反应溶液脱色过滤、降温结晶得到目的物；所述的有机溶剂为DMF，所述的催化剂为包含四甲基氯化铵和三乙胺的固液混合催化剂。本发明大大提高了产品的质量，缩短生产周期，提高了产品的收率。
Description
技术领域
本发明涉及一种生产三羟乙基异氰尿酸酯的方法，属于化工合成技术领域。
背景技术
三羟乙基异氰尿酸酯现有工艺为氰尿酸与环氧乙烷在有机溶剂乙二醇单甲醚中，在催化剂苄基三乙基氯化铵的催化下进行加成反应，一般要经过加成反应，然后浓缩溶剂套用，再加精制溶剂溶解，加活性碳脱色，然后降温，离心得湿成品，母液回收溶剂，用于下次精制，本工艺要通过浓缩溶剂再结晶，在能得到纯品。工艺过程长，能耗大。
发明内容
本发明提供一种生产三羟乙基异氰尿酸酯的方法，选择一种合适的溶剂替代原来的乙二醇单甲醚，使其可以作为反应溶剂，也可以作为精制溶剂。
本发明的目的通过以下技术方案实现：
一种生产三羟乙基异氰尿酸酯的方法，氰尿酸与环氧乙烷在催化剂的催化作用下在有机溶剂中进行加成反应，反应结束后将反应溶液脱色过滤、降温结晶得到目的物；所述的有机溶剂为DMF，所述的催化剂为包含四甲基氯化铵和三乙胺的固液混合催化剂。
所述的催化剂优选为由四甲基氯化铵和三乙胺组成的固液混合催化剂。
进一步优选，所述四甲基氯化铵和三乙胺的重量比为1～4:1。
所述四甲基氯化铵的用量为氰尿酸重量的1.5％～3％。
所述氰尿酸与环氧乙烷的重量比为1：1～1.3。
所述有机溶剂的用量为氰尿酸重量的1.5～3倍。
所述加成反应的反应温度为90～100℃。
所述加成反应的反应压力为5～6公斤压力。
本发明采用低沸点的醇甲醇、乙醇为反应溶剂。由于反应溶剂的改变，原来的催化剂三乙基苄基氯化铵也不适合新溶剂体系的加成反应，因为新溶剂极性比原来的溶剂强，所以反应体系PH偏酸，因此需要筛选一种碱性强的相转移催化剂来进行催化反应。发明人研究发现：最理性的催化剂品种和用量如下，固体催化剂四甲基氯化铵和液体催化剂三乙胺配合使用，效果最好，能同时满足反应时间和产品的质量、收率等指标。固体催化剂的用量为原料氰尿酸重量比的1.5％～3％，固体催化剂和液体催化剂的重量比为1～4:1。最优选的液体催化剂的用量为固体催化剂重量的50％。
本发明的有益效果：
采用本发明的技术方案可以使产品的综合收率由现有技术的88％提高到95％，大大提高了产品的质量，缩短生产周期，提高了产品的收率，并且使下脚料的套用次数由原来的30多次提高到80多次，有效的降低了原材料消耗，缩短反应时间，使产品质量得到进一步保证，为生产出高品质的三羟乙基异氰尿酸酯提供了保障。
具体实施方式
最优选技术方案的详细过程为：在压力反应釜中投入氰尿酸、DMF、四甲基氯化铵和三乙胺，在90～100℃，5～6公斤压力下，2～3小时内通入环氧乙烷，然后保温1～2小时后，降温到25～35℃，加入活性碳，在50～60℃保温脱色后，热过滤去除活性碳层，滤液降温到10～15℃离心，得湿成品，烘干得成品。其中所述四甲基氯化铵和三乙胺的重量比为1～4:1，所述四甲基氯化铵的用量为氰尿酸重量的1.5％～3％，所述氰尿酸与环氧乙烷的重量比为1：1～1.3，所述有机溶剂的用量为氰尿酸重量的1.5～3倍。
Claims (1)
1.一种生产三羟乙基异氰尿酸酯的方法，氰尿酸与环氧乙烷在催化剂的催化作用下在有机溶剂中进行加成反应，反应结束后将反应溶液脱色过滤、降温结晶得到目的物；所述的有机溶剂为DMF，所述的催化剂为包含四甲基氯化铵和三乙胺的固液混合催化剂。
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5719281A (en) * | 1995-03-22 | 1998-02-17 | Basf Aktiengesellschaft | Preparation of 1/3/5-Tris(2-Hydroxyalkyl) isocyanurates |
| CN1923821A (zh) * | 2006-09-28 | 2007-03-07 | 宜兴市中正化工有限公司 | 三羟乙基异氰尿酸酯的合成方法 |
| CN104710375A (zh) * | 2015-02-27 | 2015-06-17 | 宜兴市中正化工有限公司 | 一种生产三羟乙基异氰尿酸酯的方法 |
| CN207024816U (zh) * | 2017-06-07 | 2018-02-23 | 济宁键邦化工有限公司 | 三羟乙基异氰尿酸酯生产中回收母液脱色装置 |
-
2021
- 2021-04-13 CN CN202110394863.1A patent/CN113248452A/zh not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5719281A (en) * | 1995-03-22 | 1998-02-17 | Basf Aktiengesellschaft | Preparation of 1/3/5-Tris(2-Hydroxyalkyl) isocyanurates |
| CN1923821A (zh) * | 2006-09-28 | 2007-03-07 | 宜兴市中正化工有限公司 | 三羟乙基异氰尿酸酯的合成方法 |
| CN104710375A (zh) * | 2015-02-27 | 2015-06-17 | 宜兴市中正化工有限公司 | 一种生产三羟乙基异氰尿酸酯的方法 |
| CN207024816U (zh) * | 2017-06-07 | 2018-02-23 | 济宁键邦化工有限公司 | 三羟乙基异氰尿酸酯生产中回收母液脱色装置 |
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