CN101108799A - Method of synthesizing fatty acid isooctyl - Google Patents
Method of synthesizing fatty acid isooctyl Download PDFInfo
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- CN101108799A CN101108799A CNA2007100701618A CN200710070161A CN101108799A CN 101108799 A CN101108799 A CN 101108799A CN A2007100701618 A CNA2007100701618 A CN A2007100701618A CN 200710070161 A CN200710070161 A CN 200710070161A CN 101108799 A CN101108799 A CN 101108799A
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- fatty acid
- acid
- isooctyl
- synthetic method
- esterification
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Abstract
A synthetic method of the fatty acid isooctyl ester is provided, which belongs to the synthesis technology field of the ester compound in the organic chemical. The invention utilizes the fatty acid and the isooctyl ester as raw materials and carries out the esterification reaction under the function of the metallic tin catalyst, and produces the fatty acid isooctyl ester after filtration. The quality ratio between the fatty acid and the isooctyl ester is 1 : 1.05 to 1.5. The metallic tin catalyst is the stannous oxide, the stannous chloride or the stannous oxalate, which has addition of 0.01 per cent to 0.15 per cent of the total weight of the fatty acid and the isooctyl ester. The invention reasonably selects the metallic tin catalyst to make the product quality stable. The invention has advanced and reasonable process and less equipment investment through reasonable adjustment of the addition and mixture ratio of the fatty acid and the isooctyl ester and the optimized selection of the reaction temperature and the time.
Description
Technical field
The present invention relates to a kind of synthetic method of fatty acid isooctyl, belong to technical field of synthesis of ester compounds in the organic chemistry.
Background technology
The kind of fatty acid isooctyl is a lot, and what have can be used as lubricant in ore, cutting, lamination, textile oil class and the rust-preventive agent, adds the internal lubricant in man-hour as various kinds of resin; The softening agent as natural and synthetic rubber and latex, papermaking that has also can be used as releasing agent.The additive that can make senior lubricant that has; What also have has a good emollient, and spreadability and perviousness mainly are used as softener, softening agent, permeate agent in makeup.
The prior synthesizing method of fatty acid isooctyl is that reflux esterification dehydration under the effect of an acidic catalyst such as the vitriol oil, phosphoric acid etc. forms with lipid acid and isooctyl alcohol.Because the severe corrosive and the strong oxidizing property of sulfuric acid etc. to having relatively high expectations of equipment, need neutralization, washing in process of production, and the sewage emissions amount are big, the product colour that obtains is dark, thereby application is restricted; Industrial normal employing tosic acid, tetrabutyl titanate etc. are made catalyzer, but this type of catalyzer such as still need wash at process, and production technique is also complicated, and the part catalyst residue is in product, cause product quality in storage process easily to change, influence product stability.
Summary of the invention
It is reasonable to the purpose of this invention is to provide a kind of technology, simple to operate, can effectively reduce " three wastes " discharging, improves the synthetic method of the fatty acid isooctyl of product use properties.
The present invention is the synthetic method of fatty acid isooctyl, is raw material with lipid acid and isooctyl alcohol, it is characterized in that carrying out under the effect of metallic tin catalyst esterification, filters the different monooctyl ester of back obtain fatty acid.
Described resin acid acid can be saturated fatty acid or unsaturated fatty acids, comprises lauric acid, palmitinic acid, stearic acid, oleic acid etc.
The mass ratio of described lipid acid and isooctyl alcohol can be 1: 1.05～and 1.5.
Described metallic tin catalyst can be tin protoxide or tin protochloride, stannous oxalate etc., and its add-on is 0.01～0.15% of lipid acid and an isooctyl alcohol total weight percent.
The temperature of reaction of described esterification can be 160 ℃～250 ℃.
The reaction times of described esterification can be 3～8 hours.
Described esterification can be carried out under nitrogen atmosphere.
Also can carry out dealcoholation treatment after the described esterification, the dealcoholysis temperature can be 80～150 ℃, and the dealcoholysis time is 0.5～2 hour, and dealcoholysis vacuum tightness is≤80Pa.
The present invention compared with prior art has following outstanding advantage and positively effect:
1, rationally selects metallic tin catalyst for use, overcome the shortcoming of sulfuric acid and Catalyzed by p-Toluenesulfonic Acid agent in the prior art, the metallic tin catalyst Heat stability is good has higher selectivity, generate by product hardly, operation still has very high productive rate under higher temperature; And the metallic tin class is not water funk, can etching apparatus, and production technique is simple, can remove catalyzer by filtering, and makes constant product quality, and catalyzer is recyclable utilizes again.
2, by the optimized choice to reasonable adjustment, temperature of reaction and the time of the add-on of lipid acid and isooctyl alcohol and proportioning, make technology of the present invention rationally advanced, facility investment is province.
3, by synthetic fatty acid isooctyl ester of the present invention, can be widely used in the lubricant in ore, cutting, lamination, textile oil class and the rust-preventive agent, the softening agent of natural and synthetic rubber and latex, papermaking, releasing agent, the additive of senior lubricant, the softener in the makeup, softening agent, permeate agent etc.
Embodiment
Embodiment 1:
In reactor, add 400 parts of stearic acid successively, 224 parts of isooctyl alcohol, 0.218 part stannous oxalate stirs and is warming up to 75 ℃, material dissolves fully in the reactor, logical nitrogen, continue to be warming up to 210 ℃～220 ℃, under this temperature, react, distillate the water that reaction generates, after the esterification 4 hours, anhydrous distillating.Changing the depickling still over to, is 50Pa in vacuum tightness, and temperature is 110 ℃, dealcoholysis 1 hour, be cooled to 70 ℃ filter 570 parts of different monooctyl esters of stearic acid, yield is 92%.
Embodiment 2:
In reactor, add 400 parts of oleic acid successively, 223 parts of isooctyl alcohol, 0.525 part of tin protoxide, logical nitrogen is warming up to 190 ℃～200 ℃, reacts under this temperature, distillates the water that reaction generates, and esterification is after 6 hours, anhydrous distillating.Changing the depickling still over to, is 60Pa in vacuum tightness, and temperature is 120 ℃, dealcoholysis 1 hour, be cooled to 70 ℃ filter 550 parts of different monooctyl esters of oleic acid, yield is 86%.
Embodiment 3:
In reactor, add 400 parts of palmitinic acids successively, 256 parts of isooctyl alcohol, 0.787 part of tin protochloride, logical nitrogen is warming up to 180 ℃～190 ℃, reacts under this temperature, distillates the water that reaction generates, and esterification is after 7 hours, anhydrous distillating.Changing the depickling still over to, is 60Pa in vacuum tightness, and temperature is 120 ℃, dealcoholysis 1.5 hours, be cooled to 70 ℃ filter 575 parts of iso-octyl palmitates, yield is 88%.
Embodiment 4: in reactor, add 400 parts of lauric acid successively, and 312 parts of isooctyl alcohol, 0.712 part of tin protochloride, logical nitrogen is warming up to 170 ℃～180 ℃, reacts under this temperature, distillates the water that reaction generates, and esterification is after 5 hours, anhydrous distillating.Changing the depickling still over to, is 40Pa in vacuum tightness, and temperature is 100 ℃, dealcoholysis 0.5 hour, be cooled to 70 ℃ filter 624 parts of different monooctyl esters of lauric acid, yield is 88%.
Claims (8)
1. the synthetic method of a fatty acid isooctyl is a raw material with lipid acid and isooctyl alcohol, it is characterized in that carrying out under the effect of metallic tin catalyst esterification, filters the different monooctyl ester of back obtain fatty acid.
2. by the synthetic method of the described fatty acid isooctyl of claim 1, it is characterized in that described resin acid acid for saturated fatty acid or unsaturated fatty acids, comprises lauric acid, palmitinic acid, stearic acid, oleic acid.
3. by the synthetic method of claim 1 or 2 described fatty acid isooctyls, the mass ratio that it is characterized in that described lipid acid and isooctyl alcohol is 1: 1.05～1.5.
4. by the synthetic method of the described fatty acid isooctyl of claim 1, it is characterized in that described metallic tin catalyst is tin protoxide or tin protochloride, stannous oxalate, its add-on is 0.01～0.15% of lipid acid and an isooctyl alcohol total weight percent.
5. by the synthetic method of the described fatty acid isooctyl of claim 1, the temperature of reaction that it is characterized in that described esterification is 160 ℃～250 ℃.
6. by the synthetic method of claim 1 or 5 described fatty acid isooctyls, the reaction times that it is characterized in that described esterification is 3～8 hours.
7. by the synthetic method of the described fatty acid isooctyl of claim 1, it is characterized in that described esterification carries out under nitrogen atmosphere.
8. by the synthetic method of the described fatty acid isooctyl of claim 1, it is characterized in that also carrying out dealcoholation treatment after the described esterification, the dealcoholysis temperature is 80～150 ℃, and the dealcoholysis time is 0.5～2 hour, and dealcoholysis vacuum tightness is≤80Pa.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100701618A CN101108799A (en) | 2007-07-24 | 2007-07-24 | Method of synthesizing fatty acid isooctyl |
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| Application Number | Priority Date | Filing Date | Title |
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| CNA2007100701618A CN101108799A (en) | 2007-07-24 | 2007-07-24 | Method of synthesizing fatty acid isooctyl |
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| CN101108799A true CN101108799A (en) | 2008-01-23 |
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| CNA2007100701618A Pending CN101108799A (en) | 2007-07-24 | 2007-07-24 | Method of synthesizing fatty acid isooctyl |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102108050A (en) * | 2010-12-17 | 2011-06-29 | 上海博康精细化工有限公司 | Synthesis method of diphenylcarbinol decanoate |
| CN102295584A (en) * | 2011-05-23 | 2011-12-28 | 沧州大洋化工有限责任公司 | Modification method of isooctyl oleate |
| CN101633618B (en) * | 2009-08-27 | 2012-07-25 | 浙江合诚化学有限公司 | Method for synthesizing decylic acid decyl ester |
| CN101747187B (en) * | 2009-12-25 | 2013-01-16 | 浙江工业大学 | Method for preparing iso-octyl palmitate |
| CN103739493A (en) * | 2013-12-19 | 2014-04-23 | 广州正道环保新材料有限公司 | Method for efficiently producing dipropylene glycol dibenzoate |
| CN104232323A (en) * | 2013-06-24 | 2014-12-24 | 益海(连云港)油化工业有限公司 | Preparation process of fatty acid isooctyl ester |
| CN107722052A (en) * | 2017-09-27 | 2018-02-23 | 杭州金诚助剂有限公司 | One kind contains phosphorous acid organic ester antioxidant and synthetic method |
| CN108084021A (en) * | 2017-12-27 | 2018-05-29 | 上海应用技术大学 | A kind of preparation method of isobutyl palmitate |
| CN108299496A (en) * | 2017-09-27 | 2018-07-20 | 杭州金诚助剂有限公司 | Contain phosphorous acid organic ester antioxidant and synthetic method |
| CN108976119A (en) * | 2018-08-09 | 2018-12-11 | 江苏华伦化工有限公司 | The plasticizer and its preparation method and application prepared using mixed acid anhydride as raw material |
| CN108997120A (en) * | 2018-07-04 | 2018-12-14 | 湖北犇星化工有限责任公司 | A kind of preparation method and its usage of isooctyl oleate |
| CN109467682A (en) * | 2018-12-13 | 2019-03-15 | 中国科学院新疆理化技术研究所 | A kind of synthetic method of Estolides ester |
-
2007
- 2007-07-24 CN CNA2007100701618A patent/CN101108799A/en active Pending
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101633618B (en) * | 2009-08-27 | 2012-07-25 | 浙江合诚化学有限公司 | Method for synthesizing decylic acid decyl ester |
| CN101747187B (en) * | 2009-12-25 | 2013-01-16 | 浙江工业大学 | Method for preparing iso-octyl palmitate |
| CN102108050A (en) * | 2010-12-17 | 2011-06-29 | 上海博康精细化工有限公司 | Synthesis method of diphenylcarbinol decanoate |
| CN102295584A (en) * | 2011-05-23 | 2011-12-28 | 沧州大洋化工有限责任公司 | Modification method of isooctyl oleate |
| CN102295584B (en) * | 2011-05-23 | 2013-07-03 | 沧州大洋化工有限责任公司 | Modification method of isooctyl oleate |
| CN104232323A (en) * | 2013-06-24 | 2014-12-24 | 益海(连云港)油化工业有限公司 | Preparation process of fatty acid isooctyl ester |
| CN103739493A (en) * | 2013-12-19 | 2014-04-23 | 广州正道环保新材料有限公司 | Method for efficiently producing dipropylene glycol dibenzoate |
| CN107722052A (en) * | 2017-09-27 | 2018-02-23 | 杭州金诚助剂有限公司 | One kind contains phosphorous acid organic ester antioxidant and synthetic method |
| CN108299496A (en) * | 2017-09-27 | 2018-07-20 | 杭州金诚助剂有限公司 | Contain phosphorous acid organic ester antioxidant and synthetic method |
| CN107722052B (en) * | 2017-09-27 | 2021-03-02 | 杭州金诚助剂有限公司 | Antioxidant containing organic phosphite ester and synthesis method thereof |
| CN108084021A (en) * | 2017-12-27 | 2018-05-29 | 上海应用技术大学 | A kind of preparation method of isobutyl palmitate |
| CN108997120A (en) * | 2018-07-04 | 2018-12-14 | 湖北犇星化工有限责任公司 | A kind of preparation method and its usage of isooctyl oleate |
| CN108976119A (en) * | 2018-08-09 | 2018-12-11 | 江苏华伦化工有限公司 | The plasticizer and its preparation method and application prepared using mixed acid anhydride as raw material |
| CN109467682A (en) * | 2018-12-13 | 2019-03-15 | 中国科学院新疆理化技术研究所 | A kind of synthetic method of Estolides ester |
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