CN104119230A - 一种长链尼泊金酯的合成方法及其应用 - Google Patents
一种长链尼泊金酯的合成方法及其应用 Download PDFInfo
- Publication number
- CN104119230A CN104119230A CN201410291381.3A CN201410291381A CN104119230A CN 104119230 A CN104119230 A CN 104119230A CN 201410291381 A CN201410291381 A CN 201410291381A CN 104119230 A CN104119230 A CN 104119230A
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- CN
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- Prior art keywords
- alcohol
- reaction soln
- long
- chain
- normal hexane
- 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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Links
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 title abstract 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 title abstract 4
- 238000001308 synthesis method Methods 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 123
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 92
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 53
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims abstract description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000000706 filtrate Substances 0.000 claims abstract description 40
- 239000012065 filter cake Substances 0.000 claims abstract description 25
- 238000001914 filtration Methods 0.000 claims abstract description 21
- 238000003756 stirring Methods 0.000 claims abstract description 20
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 claims abstract description 18
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims abstract description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229940057402 undecyl alcohol Drugs 0.000 claims abstract description 9
- 238000010992 reflux Methods 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims description 41
- 238000002425 crystallisation Methods 0.000 claims description 36
- 230000008025 crystallization Effects 0.000 claims description 36
- 238000009834 vaporization Methods 0.000 claims description 28
- 230000008016 vaporization Effects 0.000 claims description 28
- 230000009467 reduction Effects 0.000 claims description 27
- 238000002156 mixing Methods 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 238000010189 synthetic method Methods 0.000 claims description 14
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 244000144972 livestock Species 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 244000144977 poultry Species 0.000 claims description 3
- 238000011068 loading method Methods 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 abstract description 23
- 230000032050 esterification Effects 0.000 abstract description 22
- 239000000047 product Substances 0.000 abstract description 11
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 3
- 238000001704 evaporation Methods 0.000 abstract description 3
- 238000001816 cooling Methods 0.000 abstract 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 abstract 2
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229940087291 tridecyl alcohol Drugs 0.000 abstract 1
- 238000007738 vacuum evaporation Methods 0.000 abstract 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 24
- 238000000967 suction filtration Methods 0.000 description 15
- 239000013078 crystal Substances 0.000 description 10
- BAYSQTBAJQRACX-UHFFFAOYSA-N dodecyl p-hydroxybenzoate Natural products CCCCCCCCCCCCOC(=O)C1=CC=C(O)C=C1 BAYSQTBAJQRACX-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 208000031295 Animal disease Diseases 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003260 anti-sepsis Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 235000019249 food preservative Nutrition 0.000 description 1
- 239000005452 food preservative Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
组别 | 对照组 | 实验1组(50ppm) | 实验2组(150ppm) | 实验3组(200ppm) |
始重(kg) | 9.03 | 9.05 | 9.03 | 9.04 |
末重(kg) | 12.82 | 15.35 | 13.95 | 15.7 |
平均日增重(kg) | 0.18 | 0.254 | 0.231 | 0.296 |
料重比 | 2.15 | 1.53 | 1.88 | 1.61 |
Claims (10)
Priority Applications (1)
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CN201410291381.3A CN104119230B (zh) | 2014-06-25 | 2014-06-25 | 一种长链尼泊金酯的合成方法及其应用 |
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CN201410291381.3A CN104119230B (zh) | 2014-06-25 | 2014-06-25 | 一种长链尼泊金酯的合成方法及其应用 |
Publications (2)
Publication Number | Publication Date |
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CN104119230A true CN104119230A (zh) | 2014-10-29 |
CN104119230B CN104119230B (zh) | 2015-12-30 |
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CN201410291381.3A Expired - Fee Related CN104119230B (zh) | 2014-06-25 | 2014-06-25 | 一种长链尼泊金酯的合成方法及其应用 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104355999A (zh) * | 2014-11-06 | 2015-02-18 | 宜都市华阳化工有限责任公司 | 一种水杨酸异辛酯的生产方法 |
CN104445080A (zh) * | 2014-12-12 | 2015-03-25 | 湖南兴鹏化工科技有限公司 | 用于蒽醌法过氧化氢生产工艺的复合型溶剂体系 |
CN104557531A (zh) * | 2014-12-12 | 2015-04-29 | 湖南兴鹏化工科技有限公司 | 一种反式-1,2-环己二醇二醋酸酯的制备方法 |
CN106278883A (zh) * | 2016-08-04 | 2017-01-04 | 暨南大学 | 一种尼泊金十四酯的催化合成方法 |
CN109574847A (zh) * | 2018-12-12 | 2019-04-05 | 温州瑞思生物科技有限公司 | 一种防腐剂尼泊金十一酯的绿色合成工艺 |
CN109970557A (zh) * | 2019-03-26 | 2019-07-05 | 陕西科技大学 | 一种制备尼泊金酯的方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998056748A1 (en) * | 1997-06-09 | 1998-12-17 | Peter De Nil | Method for the synthesis of anti-microbial hydroxybenzoats |
CN101982453A (zh) * | 2010-09-10 | 2011-03-02 | 周峰岩 | 一种磺酸型离子液体促进下尼泊金酯类化合物的制备方法 |
-
2014
- 2014-06-25 CN CN201410291381.3A patent/CN104119230B/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998056748A1 (en) * | 1997-06-09 | 1998-12-17 | Peter De Nil | Method for the synthesis of anti-microbial hydroxybenzoats |
CN101982453A (zh) * | 2010-09-10 | 2011-03-02 | 周峰岩 | 一种磺酸型离子液体促进下尼泊金酯类化合物的制备方法 |
Non-Patent Citations (2)
Title |
---|
侯艳冰等: ""长链尼泊金酯类防腐剂的合成研究"", 《食品科技》 * |
项艳: ""防腐剂—对羟基苯甲酸正丁酯的合成"", 《绿色科技》 * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104355999A (zh) * | 2014-11-06 | 2015-02-18 | 宜都市华阳化工有限责任公司 | 一种水杨酸异辛酯的生产方法 |
CN104355999B (zh) * | 2014-11-06 | 2016-08-17 | 宜都市华阳化工有限责任公司 | 一种水杨酸异辛酯的生产方法 |
CN104445080A (zh) * | 2014-12-12 | 2015-03-25 | 湖南兴鹏化工科技有限公司 | 用于蒽醌法过氧化氢生产工艺的复合型溶剂体系 |
CN104557531A (zh) * | 2014-12-12 | 2015-04-29 | 湖南兴鹏化工科技有限公司 | 一种反式-1,2-环己二醇二醋酸酯的制备方法 |
CN104557531B (zh) * | 2014-12-12 | 2016-08-31 | 湖南兴鹏化工科技有限公司 | 一种反式-1,2-环己二醇二醋酸酯的制备方法 |
CN104445080B (zh) * | 2014-12-12 | 2017-02-01 | 湖南兴鹏化工科技有限公司 | 用于蒽醌法过氧化氢生产工艺的复合型溶剂体系 |
CN106278883A (zh) * | 2016-08-04 | 2017-01-04 | 暨南大学 | 一种尼泊金十四酯的催化合成方法 |
CN109574847A (zh) * | 2018-12-12 | 2019-04-05 | 温州瑞思生物科技有限公司 | 一种防腐剂尼泊金十一酯的绿色合成工艺 |
CN109970557A (zh) * | 2019-03-26 | 2019-07-05 | 陕西科技大学 | 一种制备尼泊金酯的方法 |
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Publication number | Publication date |
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CN104119230B (zh) | 2015-12-30 |
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Denomination of invention: A synthetic method of long chain Nipagin ester and its application Effective date of registration: 20210811 Granted publication date: 20151230 Pledgee: Beijing first financing Company limited by guarantee Pledgor: Beijing Junde Tongchuang Biotechnology Co.,Ltd. Registration number: Y2021110000027 |
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Effective date of registration: 20221124 Address after: Room 504, Scientific Research Auxiliary Building, Feed Research Institute, Chinese Academy of Agricultural Sciences, No. 12, Zhongguancun South Street, Haidian District, Beijing 100085 Patentee after: Li Bingjie Address before: Room 601, Block B, Jiahua Building, No. 9, Shangdi 3rd Street, Haidian District, Beijing 100085 Patentee before: Beijing Junde Tongchuang Biotechnology Co.,Ltd. |
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