CN104592171B - Production method of epoxy fatty acid methyl ester - Google Patents
Production method of epoxy fatty acid methyl ester Download PDFInfo
- Publication number
- CN104592171B CN104592171B CN201510028049.2A CN201510028049A CN104592171B CN 104592171 B CN104592171 B CN 104592171B CN 201510028049 A CN201510028049 A CN 201510028049A CN 104592171 B CN104592171 B CN 104592171B
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- CN
- China
- Prior art keywords
- methyl ester
- acid methyl
- parts
- fatty acid
- epoxy aliphatic
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- 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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- 239000004593 Epoxy Substances 0.000 title claims abstract description 40
- 235000019387 fatty acid methyl ester Nutrition 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- 238000003756 stirring Methods 0.000 claims abstract description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 239000007788 liquid Substances 0.000 claims abstract description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 12
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 12
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229960004889 salicylic acid Drugs 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 35
- 125000001931 aliphatic group Chemical group 0.000 claims description 35
- 150000004702 methyl esters Chemical class 0.000 claims description 35
- 239000002699 waste material Substances 0.000 claims description 34
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 22
- 239000012530 fluid Substances 0.000 claims description 20
- 229910000358 iron sulfate Inorganic materials 0.000 claims description 11
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 11
- 235000011009 potassium phosphates Nutrition 0.000 claims description 11
- 239000001488 sodium phosphate Substances 0.000 claims description 11
- 235000011008 sodium phosphates Nutrition 0.000 claims description 11
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 11
- 238000013517 stratification Methods 0.000 claims description 10
- 235000011149 sulphuric acid Nutrition 0.000 claims description 10
- 239000006228 supernatant Substances 0.000 claims description 10
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 6
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 6
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 239000001117 sulphuric acid Substances 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- 239000002994 raw material Substances 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 2
- 239000008162 cooking oil Substances 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000003921 oil Substances 0.000 description 31
- 239000000047 product Substances 0.000 description 7
- 230000007613 environmental effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention discloses a production method of epoxidized fatty acid methyl ester, belonging to the technical field of chemical product preparation. The method comprises the steps of preparing the illegal cooking oil to be treated into illegal cooking oil pretreatment liquid, adding concentrated sulfuric acid, stirring and heating, dripping methanol, stirring at constant temperature, standing for layering, taking the upper liquid to obtain crude fatty acid methyl ester, putting the crude fatty acid methyl ester into a rectifying tower, and rectifying to obtain refined fatty acid methyl ester; putting fatty acid methyl ester into a reaction kettle, adding salicylic acid and a specific catalyst, heating, adding hydrogen peroxide and concentrated sulfuric acid, stirring, standing, layering, and taking the upper layer liquid to obtain crude epoxy fatty acid methyl ester; rectifying the crude epoxy fatty acid methyl ester to obtain refined epoxy fatty acid methyl ester. The invention adopts the illegal cooking oil as the main raw material, thereby replacing the traditional scheme of directly adopting the fatty acid methyl ester as the preparation raw material, not only fully utilizing the illegal cooking oil, but also greatly lowering the production cost of the finished product of the epoxy fatty acid methyl ester.
Description
Technical field
The invention belongs to chemical products preparing technical field, particularly relate to the production method of a kind of epoxy aliphatic acid methyl ester.
Background technology
Epoxy aliphatic acid methyl ester is light yellow liquid at normal temperatures, is that a kind of nontoxic, tasteless novel environment-friendlyplasticizer plasticizer is held concurrently stabilizer.At present, epoxy aliphatic acid methyl ester is mainly directly prepared from fatty acid methyl ester for raw material, but, owing to the price of fatty acid methyl ester remains high always, cause the preparation cost of epoxy aliphatic acid methyl ester to there is too high defect.
Waste oil, refer to life present in all kinds of poor oils, as reclaim edible oil, the frying oil etc. of Reusability.On the other hand the appearance of waste oil, the most not only can there is likely to be waste oil backflow dining table cause serious safe diet hidden danger to environment.In order to eliminate safety and the environmental protection hidden danger that above-mentioned waste oil produces, people attempt being converted into waste oil safer, useful product.
Summary of the invention
The present invention provides the production method of a kind of epoxy aliphatic acid methyl ester, waste oil is made epoxy aliphatic acid methyl ester as raw material by method, thus while the existing waste oil of solution exists safety and environmental protection potential problem, the preparation cost of epoxy aliphatic acid methyl ester can be effectively reduced again.
In order to solve above-mentioned technical problem, the technical solution adopted in the present invention is:
It comprises the following steps:
A, remove the solid matter contained in pending waste oil, be then heated to 70 DEG C～80 DEG C, and filtered by nanometer overclocking vibration film group, obtain waste oil pretreatment fluid；
B, by step A prepare waste oil pretreatment fluid put in agitator, under stirring condition, it is added to account for the concentrated sulphuric acid of described waste oil pretreatment fluid quality 0.5%～0.8%, stir, it is heated to 65 DEG C～75 DEG C, dropping accounts for the methanol of described waste oil pretreatment fluid quality 8%～11%, and constant temperature stirs 8 hours～12 hours, then stratification, take supernatant liquid, obtain crude fatty acid methyl ester；
C, by step B prepare crude fatty acid methyl ester put in rectifying column, be 200 DEG C～220 DEG C in temperature, pressure is rectification under conditions of 0MPa～0.001MPa, obtains the fatty acid methyl ester refined；
D, by weight, the refined fatty acid methyl ester 100 parts of step C prepared is put in reactor, and add 46 parts of salicylic acid and 0.5 part of catalyst, stir, be warming up to 80 DEG C～85 DEG C the most again, and add 22 parts of hydrogen peroxide and 3 parts of concentrated sulphuric acids, stir 4 hours～6 hours, last stratification, takes supernatant liquid, obtains thick epoxy aliphatic acid methyl ester；Wherein, described catalyst by weight, is mixed to prepare by 35 parts～45 parts of sodium phosphates, 20 parts～22 parts of iron sulfate and 8 parts～12 parts of potassium phosphates；
E, by D step prepare thick epoxy aliphatic acid methyl ester carry out rectification, obtain the epoxy aliphatic acid methyl ester refined.
In technique scheme, more specifically technical scheme is: in described D step catalyst, sodium phosphate 35 parts, 22 parts of iron sulfate, potassium phosphate 10 parts.
Further, in described D step catalyst, sodium phosphate 40 parts, 20 parts of iron sulfate, potassium phosphate 12 parts.
Further, in described D step catalyst, sodium phosphate 45 parts, 21 parts of iron sulfate, potassium phosphate 8 parts.
Owing to using technique scheme, the present invention obtains providing the benefit that:
1. the present invention uses waste oil as primary raw material, thus replace tradition directly to use fatty acid methyl ester as preparing the scheme of raw material and by using specific catalyst, waste oil not only can be made to be fully utilized, also can the production cost of significantly finished product epoxy aliphatic acid methyl ester.
2. the present invention produces the product epoxy aliphatic acid methyl ester purity height obtained.
Detailed description of the invention
Below in conjunction with specific embodiment, the invention will be further described, and protection scope of the present invention is not intended to be limited to following example.
Embodiment 1
The production method of this epoxy aliphatic acid methyl ester comprises the following steps:
A, remove the solid matter contained in pending waste oil, be then heated to 70 DEG C, and filtered by nanometer overclocking vibration film group, obtain waste oil pretreatment fluid；
B, by step A prepare waste oil pretreatment fluid put in agitator, under stirring condition, it is added to account for the concentrated sulphuric acid of described waste oil pretreatment fluid quality 0.5%, stir, it is heated to 65 DEG C, dropping accounts for the methanol of described waste oil pretreatment fluid quality 8%, and constant temperature stirs 12 hours, then stratification, take supernatant liquid, obtain crude fatty acid methyl ester；
C, by step B prepare crude fatty acid methyl ester put in rectifying column, be 200 DEG C in temperature, pressure is rectification under conditions of 0MPa, obtains the fatty acid methyl ester refined；
D, by weight, the refined fatty acid methyl ester 100 parts of step C prepared is put in reactor, and add 46 parts of salicylic acid and 0.5 part of catalyst, stir, be warming up to 80 DEG C the most again, and add 22 parts of hydrogen peroxide and 3 parts of concentrated sulphuric acids, stir 6 hours, last stratification, takes supernatant liquid, obtains thick epoxy aliphatic acid methyl ester；Wherein, described catalyst by weight, is mixed to prepare by 35 parts of sodium phosphates, 22 parts of iron sulfate and 10 parts of potassium phosphates；
E, by D step prepare thick epoxy aliphatic acid methyl ester carry out rectification, obtain the epoxy aliphatic acid methyl ester refined.
It is 97.1% that the present embodiment produces the product epoxy aliphatic acid methyl ester purity obtained.
Embodiment 2
The production method of this epoxy aliphatic acid methyl ester comprises the following steps:
A, remove the solid matter contained in pending waste oil, be then heated to 80 DEG C, and filtered by nanometer overclocking vibration film group, obtain waste oil pretreatment fluid；
B, by step A prepare waste oil pretreatment fluid put in agitator, under stirring condition, it is added to account for the concentrated sulphuric acid of described waste oil pretreatment fluid quality 0.8%, stir, it is heated to 75 DEG C, dropping accounts for the methanol of described waste oil pretreatment fluid quality 11%, and constant temperature stirs 8 hours, then stratification, take supernatant liquid, obtain crude fatty acid methyl ester；
C, by step B prepare crude fatty acid methyl ester put in rectifying column, be 220 DEG C in temperature, pressure is rectification under conditions of 0.001MPa, obtains the fatty acid methyl ester refined；
D, by weight, the refined fatty acid methyl ester 100 parts of step C prepared is put in reactor, and add 46 parts of salicylic acid and 0.5 part of catalyst, stir, be warming up to 85 DEG C the most again, and add 22 parts of hydrogen peroxide and 3 parts of concentrated sulphuric acids, stir 4 hours, last stratification, takes supernatant liquid, obtains thick epoxy aliphatic acid methyl ester；Wherein, described catalyst by weight, is mixed to prepare by 40 parts of sodium phosphates, 20 parts of iron sulfate and 12 parts of potassium phosphates；
E, by D step prepare thick epoxy aliphatic acid methyl ester carry out rectification, obtain the epoxy aliphatic acid methyl ester refined.
It is 96.7% that the present embodiment produces the product epoxy aliphatic acid methyl ester purity obtained.
Embodiment 3
The production method of this epoxy aliphatic acid methyl ester comprises the following steps:
A, remove the solid matter contained in pending waste oil, be then heated to 75 DEG C, and filtered by nanometer overclocking vibration film group, obtain waste oil pretreatment fluid；
B, by step A prepare waste oil pretreatment fluid put in agitator, under stirring condition, it is added to account for the concentrated sulphuric acid of described waste oil pretreatment fluid quality 0.6%, stir, it is heated to 70 DEG C, dropping accounts for the methanol of described waste oil pretreatment fluid quality 9%, and constant temperature stirs 10 hours, then stratification, take supernatant liquid, obtain crude fatty acid methyl ester；
C, by step B prepare crude fatty acid methyl ester put in rectifying column, be 210 DEG C in temperature, pressure is rectification under conditions of 0.001MPa, obtains the fatty acid methyl ester refined；
D, by weight, the refined fatty acid methyl ester 100 parts of step C prepared is put in reactor, and add 46 parts of salicylic acid and 0.5 part of catalyst, stir, be warming up to 82 DEG C the most again, and add 22 parts of hydrogen peroxide and 3 parts of concentrated sulphuric acids, stir 5 hours, last stratification, takes supernatant liquid, obtains thick epoxy aliphatic acid methyl ester；Wherein, described catalyst by weight, is mixed to prepare by 45 parts of sodium phosphates, 21 parts of iron sulfate and 8 parts of potassium phosphates；
E, by D step prepare thick epoxy aliphatic acid methyl ester carry out rectification, obtain the epoxy aliphatic acid methyl ester refined.
It is 96.5% that the present embodiment produces the product epoxy aliphatic acid methyl ester purity obtained.
Claims (4)
1. the production method of an epoxy aliphatic acid methyl ester, it is characterised in that comprise the following steps:
A, remove the solid matter contained in pending waste oil, be then heated to 70 DEG C～80 DEG C, and filtered by nanometer overclocking vibration film group, obtain waste oil pretreatment fluid；
B, by step A prepare waste oil pretreatment fluid put in agitator, under stirring condition, it is added to account for the concentrated sulphuric acid of described waste oil pretreatment fluid quality 0.5%～0.8%, stir, it is heated to 65 DEG C～75 DEG C, dropping accounts for the methanol of described waste oil pretreatment fluid quality 8%～11%, and constant temperature stirs 8 hours～12 hours, then stratification, take supernatant liquid, obtain crude fatty acid methyl ester；
C, by step B prepare crude fatty acid methyl ester put in rectifying column, be 200 DEG C～220 DEG C in temperature, pressure is rectification under conditions of 0MPa～0.001MPa, obtains the fatty acid methyl ester refined；
D, by weight, the refined fatty acid methyl ester 100 parts of step C prepared is put in reactor, and add 46 parts of salicylic acid and 0.5 part of catalyst, stir, be warming up to 80 DEG C～85 DEG C the most again, and add 22 parts of hydrogen peroxide and 3 parts of concentrated sulphuric acids, stir 4 hours～6 hours, last stratification, takes supernatant liquid, obtains thick epoxy aliphatic acid methyl ester；Wherein, described catalyst by weight, is mixed to prepare by 35 parts～45 parts of sodium phosphates, 20 parts～22 parts of iron sulfate and 8 parts～12 parts of potassium phosphates；
E, by D step prepare thick epoxy aliphatic acid methyl ester carry out rectification, obtain the epoxy aliphatic acid methyl ester refined.
The production method of epoxy aliphatic acid methyl ester the most according to claim 1, it is characterised in that: in described D step catalyst, sodium phosphate 35 parts, 22 parts of iron sulfate, potassium phosphate 10 parts.
The production method of epoxy aliphatic acid methyl ester the most according to claim 1, it is characterised in that: in described D step catalyst, sodium phosphate 40 parts, 20 parts of iron sulfate, potassium phosphate 12 parts.
The production method of epoxy aliphatic acid methyl ester the most according to claim 1, it is characterised in that: in described D step catalyst, sodium phosphate 45 parts, 21 parts of iron sulfate, potassium phosphate 8 parts.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510028049.2A CN104592171B (en) | 2015-01-21 | 2015-01-21 | Production method of epoxy fatty acid methyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510028049.2A CN104592171B (en) | 2015-01-21 | 2015-01-21 | Production method of epoxy fatty acid methyl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104592171A CN104592171A (en) | 2015-05-06 |
| CN104592171B true CN104592171B (en) | 2017-01-04 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201510028049.2A Active CN104592171B (en) | 2015-01-21 | 2015-01-21 | Production method of epoxy fatty acid methyl ester |
Country Status (1)
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| CN (1) | CN104592171B (en) |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8173825B2 (en) * | 2006-12-20 | 2012-05-08 | The United States Of America, As Represented By The Secretary Of Agriculture | Method of making fatty acid ester derivatives |
| CN100580025C (en) * | 2007-02-27 | 2010-01-13 | 张伟明 | Method for producing epoxy plasticizer from dirty oil and vegetable and animal waste oil |
| CN100590188C (en) * | 2007-05-22 | 2010-02-17 | 江阴市向阳科技有限公司 | Method for producing epoxy plasticizer using waste grease |
| CN101372539B (en) * | 2008-07-31 | 2011-07-06 | 浙江嘉澳环保科技股份有限公司 | Method for producing environment-friendly type plasticiser using waste oil and oil foot |
| CN101891713B (en) * | 2010-07-09 | 2012-02-29 | 南京工业大学 | Method for preparing epoxy fatty acid methyl ester |
| CN102344856A (en) * | 2010-07-28 | 2012-02-08 | 肖连朝 | Technological method for preparing epoxy fatty acid methyl ester plasticizer with waste vegetable oil |
| CN102060812B (en) * | 2010-12-28 | 2012-07-25 | 江苏高科石化股份有限公司 | Method for preparing epoxy fatty acid methyl ester |
| CN102161938B (en) * | 2011-03-25 | 2013-01-02 | 河北金谷油脂科技有限公司 | Method for producing epoxy fatty acid methyl ester by using illegal cooking oil |
| CN102964314A (en) * | 2012-12-03 | 2013-03-13 | 浙江嘉澳环保科技股份有限公司 | Preparation method of epoxidized fatty acid methyl ester |
| CN102993133B (en) * | 2013-01-08 | 2015-09-02 | 南京工业大学 | The method of epoxy aliphatic acid methyl ester is prepared by microreactor single stage method |
| KR101454750B1 (en) * | 2013-01-28 | 2014-10-27 | 동구산업(주) | Improved process for preparing epoxidized fatty acid ester |
| CN103074155B (en) * | 2013-02-04 | 2014-05-07 | 佛山市浚丰华环保科技有限公司 | Drainage oil treatment process |
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2015
- 2015-01-21 CN CN201510028049.2A patent/CN104592171B/en active Active
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| CN104592171A (en) | 2015-05-06 |
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Effective date of registration: 20220210 Address after: 434200 Lingang New Area construction headquarters office building, Songzi City, Jingzhou City, Hubei Province Patentee after: Hubei saienli Fine Chemical Co.,Ltd. Address before: 545005 No. 401, unit 2, building 18, zone 1, No. 94, Chengzhan Road, Liunan District, Liuzhou City, Guangxi Zhuang Autonomous Region Patentee before: Wu Junrong |
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