CN103848742A - 高效生产二甘醇二苯甲酸酯的方法 - Google Patents
高效生产二甘醇二苯甲酸酯的方法 Download PDFInfo
- Publication number
- CN103848742A CN103848742A CN201310701995.XA CN201310701995A CN103848742A CN 103848742 A CN103848742 A CN 103848742A CN 201310701995 A CN201310701995 A CN 201310701995A CN 103848742 A CN103848742 A CN 103848742A
- Authority
- CN
- China
- Prior art keywords
- diethylene glycol
- reaction
- glycol dibenzoate
- phenylformic acid
- product
- 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.)
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- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 19
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000005406 washing Methods 0.000 claims abstract description 22
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 10
- 239000000047 product Substances 0.000 claims description 26
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
- 239000006227 byproduct Substances 0.000 claims description 10
- 238000005886 esterification reaction Methods 0.000 claims description 10
- 230000032050 esterification Effects 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 230000001588 bifunctional effect Effects 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 230000002441 reversible effect Effects 0.000 claims description 6
- 206010013786 Dry skin Diseases 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 abstract description 4
- 230000003472 neutralizing effect Effects 0.000 abstract 2
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 abstract 2
- 229910000342 sodium bisulfate Inorganic materials 0.000 abstract 2
- FJRUWRJAJNEIKD-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-6,7-diamine Chemical compound O1CCOC2=C1C=C(N)C(N)=C2 FJRUWRJAJNEIKD-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000005086 pumping Methods 0.000 abstract 1
- 238000005303 weighing Methods 0.000 abstract 1
- 239000004902 Softening Agent Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- -1 glycol ethers Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201310701995.XA CN103848742B (zh) | 2013-12-19 | 2013-12-19 | 高效生产二甘醇二苯甲酸酯的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CN201310701995.XA CN103848742B (zh) | 2013-12-19 | 2013-12-19 | 高效生产二甘醇二苯甲酸酯的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103848742A true CN103848742A (zh) | 2014-06-11 |
CN103848742B CN103848742B (zh) | 2016-04-27 |
Family
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Family Applications (1)
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CN201310701995.XA Active CN103848742B (zh) | 2013-12-19 | 2013-12-19 | 高效生产二甘醇二苯甲酸酯的方法 |
Country Status (1)
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CN (1) | CN103848742B (zh) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101376631A (zh) * | 2008-10-07 | 2009-03-04 | 杭州临安商通塑化有限公司 | 一种一缩二乙二醇二苯甲酸酯增塑剂的环保制备方法 |
CN101407461A (zh) * | 2008-11-03 | 2009-04-15 | 华东师范大学 | 一种二甘醇二苯甲酸酯的制备方法 |
CN101492372A (zh) * | 2008-12-01 | 2009-07-29 | 无锡双象化学工业有限公司 | 增塑剂二甘醇二苯甲酸酯的生产方法 |
CN101987819A (zh) * | 2009-08-07 | 2011-03-23 | 成都亚恩科技实业有限公司 | 一种多元醇苯甲酸酯增塑剂的制备方法 |
CN103012152A (zh) * | 2013-01-17 | 2013-04-03 | 岑溪市祥胜化工有限公司 | 二甘醇二苯甲酸酯的生产工艺方法 |
CN103086891A (zh) * | 2013-02-22 | 2013-05-08 | 厦门大学 | 增塑剂二甘醇二苯甲酸酯的制备方法 |
-
2013
- 2013-12-19 CN CN201310701995.XA patent/CN103848742B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101376631A (zh) * | 2008-10-07 | 2009-03-04 | 杭州临安商通塑化有限公司 | 一种一缩二乙二醇二苯甲酸酯增塑剂的环保制备方法 |
CN101407461A (zh) * | 2008-11-03 | 2009-04-15 | 华东师范大学 | 一种二甘醇二苯甲酸酯的制备方法 |
CN101492372A (zh) * | 2008-12-01 | 2009-07-29 | 无锡双象化学工业有限公司 | 增塑剂二甘醇二苯甲酸酯的生产方法 |
CN101987819A (zh) * | 2009-08-07 | 2011-03-23 | 成都亚恩科技实业有限公司 | 一种多元醇苯甲酸酯增塑剂的制备方法 |
CN103012152A (zh) * | 2013-01-17 | 2013-04-03 | 岑溪市祥胜化工有限公司 | 二甘醇二苯甲酸酯的生产工艺方法 |
CN103086891A (zh) * | 2013-02-22 | 2013-05-08 | 厦门大学 | 增塑剂二甘醇二苯甲酸酯的制备方法 |
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CN103848742B (zh) | 2016-04-27 |
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Effective date of registration: 20240125 Address after: 438000 Ditang village, yangyinling, Huangzhou Railway Station Development Zone, Huanggang City, Hubei Province Patentee after: Wuhan yikede Fine Chemical Co.,Ltd. Country or region after: China Address before: No. 69, Gangtai Road, Gangzaidi, Changgang Village, Jianggao Town, Baiyun District, Guangzhou City, Guangdong Province, 510000 Patentee before: GUANGZHOU ZHENGDAO ENVIRONMENTAL PROTECTION NEW Co.,Ltd. Country or region before: China |
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