CN102304045A - 活性炭固载硫酸催化剂合成乙酰柠檬酸三丁酯的一体化工艺 - Google Patents
活性炭固载硫酸催化剂合成乙酰柠檬酸三丁酯的一体化工艺 Download PDFInfo
- Publication number
- CN102304045A CN102304045A CN201110191984A CN201110191984A CN102304045A CN 102304045 A CN102304045 A CN 102304045A CN 201110191984 A CN201110191984 A CN 201110191984A CN 201110191984 A CN201110191984 A CN 201110191984A CN 102304045 A CN102304045 A CN 102304045A
- Authority
- CN
- China
- Prior art keywords
- tributyl citrate
- acetyl tributyl
- tbc
- synthesizing acetyl
- sulfuric acid
- 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.)
- Granted
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims abstract description 49
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000003054 catalyst Substances 0.000 title claims abstract description 34
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 23
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 48
- 238000002360 preparation method Methods 0.000 claims abstract description 23
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 11
- 230000036571 hydration Effects 0.000 claims abstract description 10
- 238000006703 hydration reaction Methods 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 238000007670 refining Methods 0.000 claims abstract description 7
- 239000002023 wood Substances 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 4
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000001117 sulphuric acid Substances 0.000 claims description 9
- 235000011149 sulphuric acid Nutrition 0.000 claims description 9
- 238000006386 neutralization reaction Methods 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 238000005303 weighing Methods 0.000 claims description 5
- 239000002699 waste material Substances 0.000 abstract description 6
- 238000005917 acylation reaction Methods 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 230000003100 immobilizing effect Effects 0.000 abstract 1
- 238000002791 soaking Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 23
- 239000002253 acid Substances 0.000 description 9
- 239000003513 alkali Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000011973 solid acid Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 239000002932 luster Substances 0.000 description 4
- LTUDISCZKZHRMJ-UHFFFAOYSA-N potassium;hydrate Chemical compound O.[K] LTUDISCZKZHRMJ-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000013335 mesoporous material Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000007171 acid catalysis Methods 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- -1 phthalic acid ester Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 238000005255 carburizing Methods 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
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CN201110191984.2A CN102304045B (zh) | 2011-07-11 | 2011-07-11 | 活性炭固载硫酸催化剂合成乙酰柠檬酸三丁酯的一体化工艺 |
Applications Claiming Priority (1)
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CN201110191984.2A CN102304045B (zh) | 2011-07-11 | 2011-07-11 | 活性炭固载硫酸催化剂合成乙酰柠檬酸三丁酯的一体化工艺 |
Publications (2)
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CN102304045A true CN102304045A (zh) | 2012-01-04 |
CN102304045B CN102304045B (zh) | 2014-04-30 |
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CN201110191984.2A Expired - Fee Related CN102304045B (zh) | 2011-07-11 | 2011-07-11 | 活性炭固载硫酸催化剂合成乙酰柠檬酸三丁酯的一体化工艺 |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102701975A (zh) * | 2012-04-11 | 2012-10-03 | 江苏雷蒙化工科技有限公司 | 活性碳固载硫酸合成乙酰柠檬酸三正丁酯工艺的改进 |
CN103316696A (zh) * | 2013-07-03 | 2013-09-25 | 宁波永顺精细化工有限公司 | 乙酰柠檬酸三正丁酯的制备方法及所用的催化剂 |
WO2013170430A1 (zh) * | 2012-05-14 | 2013-11-21 | 南京工业大学 | 一种合成酰化柠檬酸酯的工艺 |
CN104744245A (zh) * | 2015-03-25 | 2015-07-01 | 南京航空航天大学 | 活性炭固载对甲苯磺酸催化剂合成乙酰柠檬酸三丁酯一体化工艺 |
CN104803847A (zh) * | 2015-03-05 | 2015-07-29 | 江苏雷蒙化工科技有限公司 | 一种复合型固体酸催化合成乙酰柠檬酸三丁酯的工艺 |
CN105749967A (zh) * | 2016-04-06 | 2016-07-13 | 南宁市化工研究设计院 | 利用竹炭基固体磺酸催化剂制备柠檬酸三丁酯的方法 |
CN108892613A (zh) * | 2018-07-11 | 2018-11-27 | 广东轻工职业技术学院 | 一种酸改性h-zms-5型分子筛合成柠檬酸三正丁酯的方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101125814A (zh) * | 2007-09-17 | 2008-02-20 | 李祥庆 | 利用离子型催化剂合成乙酰柠檬酸三丁酯的方法 |
CN101402571A (zh) * | 2008-11-06 | 2009-04-08 | 河南庆安化工高科技股份有限公司 | 一种乙酰柠檬酸三丁酯生产工艺 |
-
2011
- 2011-07-11 CN CN201110191984.2A patent/CN102304045B/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101125814A (zh) * | 2007-09-17 | 2008-02-20 | 李祥庆 | 利用离子型催化剂合成乙酰柠檬酸三丁酯的方法 |
CN101402571A (zh) * | 2008-11-06 | 2009-04-08 | 河南庆安化工高科技股份有限公司 | 一种乙酰柠檬酸三丁酯生产工艺 |
Non-Patent Citations (1)
Title |
---|
马培华 等: "活性炭固载硫酸催化合成乙酸乙酯和环己稀", 《实验技术与管理》 * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102701975A (zh) * | 2012-04-11 | 2012-10-03 | 江苏雷蒙化工科技有限公司 | 活性碳固载硫酸合成乙酰柠檬酸三正丁酯工艺的改进 |
WO2013170430A1 (zh) * | 2012-05-14 | 2013-11-21 | 南京工业大学 | 一种合成酰化柠檬酸酯的工艺 |
CN103316696A (zh) * | 2013-07-03 | 2013-09-25 | 宁波永顺精细化工有限公司 | 乙酰柠檬酸三正丁酯的制备方法及所用的催化剂 |
CN103316696B (zh) * | 2013-07-03 | 2015-02-25 | 宁波永顺精细化工有限公司 | 乙酰柠檬酸三正丁酯的制备方法及所用的催化剂 |
CN104803847A (zh) * | 2015-03-05 | 2015-07-29 | 江苏雷蒙化工科技有限公司 | 一种复合型固体酸催化合成乙酰柠檬酸三丁酯的工艺 |
CN104744245A (zh) * | 2015-03-25 | 2015-07-01 | 南京航空航天大学 | 活性炭固载对甲苯磺酸催化剂合成乙酰柠檬酸三丁酯一体化工艺 |
CN105749967A (zh) * | 2016-04-06 | 2016-07-13 | 南宁市化工研究设计院 | 利用竹炭基固体磺酸催化剂制备柠檬酸三丁酯的方法 |
CN108892613A (zh) * | 2018-07-11 | 2018-11-27 | 广东轻工职业技术学院 | 一种酸改性h-zms-5型分子筛合成柠檬酸三正丁酯的方法 |
CN108892613B (zh) * | 2018-07-11 | 2021-02-19 | 广东轻工职业技术学院 | 一种酸改性h-zms-5型分子筛合成柠檬酸三正丁酯的方法 |
Also Published As
Publication number | Publication date |
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CN102304045B (zh) | 2014-04-30 |
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Application publication date: 20120104 Assignee: Jiangsu Lemon Chemical & Technology Co.,Ltd. Assignor: Nanjing Tech University Contract record no.: 2016320000130 Denomination of invention: Integrated process for synthesizing acetyl tributyl citrate (ATBC) from active carbon solid-carried sulphuric acid catalyst Granted publication date: 20140430 License type: Exclusive License Record date: 20160418 |
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