CN106748759A - A kind of preparation method of bio-based pentaerythritol fatty ester - Google Patents
A kind of preparation method of bio-based pentaerythritol fatty ester Download PDFInfo
- Publication number
- CN106748759A CN106748759A CN201510828755.5A CN201510828755A CN106748759A CN 106748759 A CN106748759 A CN 106748759A CN 201510828755 A CN201510828755 A CN 201510828755A CN 106748759 A CN106748759 A CN 106748759A
- Authority
- CN
- China
- Prior art keywords
- bio
- acid
- esterification
- preparation
- ester
- 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.)
- Pending
Links
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
- 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
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention discloses a kind of preparation method of bio-based pentaerythritol fatty ester, belongs to lactate synthesis technical field in organic chemistry.Specifically pentaerythrite is mixed with bio-based aliphatic acid, degassing is flowed under condition of negative pressure carries out self-catalytic esterification reaction, bio-based pentaerythritol fatty ester is obtained by the refining steps such as dealcoholysis, distillation depickling are separated.The advantage of the invention is that：Self-catalytic esterification reaction without extra catalyst, can avoid at present generally using the catalyst that is remained in building-up process of conventional catalyst esterification techniques with compound state in the form of be present in products molecule in and influence the combination property of product；Process for separating and purifying is simple, it is easy to control；Esterification degree is high, and side reaction is few, and product purity is high；The high temperature stability performance of product is good.
Description
Technical field
The present invention relates to lactate synthesis technical field in organic chemistry, specifically a kind of bio-based season
The preparation method of penta 4 alcohol fatty acid esters.
Background technology
With the raising of development and the environmental requirement of modern industry, people are to environmental problem growing interest.
Current more than 95% source of lubricating is in oil, and the biological degradability of petroleum based lubricants is very poor；It is another
Aspect, Global Oil resource is increasingly deficient, result in petroleum based lubricants shortage of resources.Thus, with
Renewable resource is received significant attention for Material synthesis biodegradable lube base oil.Bio-based
Esters base oil is because of its unique high temperature performance, viscosity temperature characteristic, greasy property, biodegradable
Energy etc. has obtained more and more being widely applied.
Pentaerythritol ester belongs to polyalcohol esters base oil, due to the special knot of quaternary carbon atom in its molecule
Structure so that the resonant structure ring of six atoms, this ester can be formed on β positions with hydroxyl oxygen without hydrogen atom
Structure only have can just be corrupted such that under high energy conditions its have splendid thermostability with oxidation
Stability.Additionally, the hydrolytic stability of pentaerythritol ester is good, viscosity performance and cryogenic property are excellent,
Not only there is the superior function of petroleum based lubricants, and meet renewable and biodegradable these two aspects
Requirement.Therefore pentaerythritol ester can substitute petroleum based lubricants at many aspects, e.g., be applied to
The fields such as aviation engine lubricating oil, metallic high temperature processing oil, preparation medium, with very big market
Potentiality and wide application prospect.The preparation technology of current pentaerythritol ester is broadly divided into acid catalyzed esterification
Two kinds transesterification with base catalysis.
Acid catalyzed esterification technology be by aliphatic acid and pentaerythrite under acid catalysis synthesis of pentaerythritol
Ester, it is catalyst generally to use the 98wt.% concentrated sulfuric acids or phosphoric acid, and residual acid and esterification degree are technology keys.
Using acidic catalyst, the especially sulfuric acid with severe corrosive and strong oxidizing property, not only reaction conversion
Rate is low, serious to equipment corrosion, and removes catalyst and the subsequent handling such as need to neutralize, wash, gives birth to
Product route is long, and the discharge of a large amount of waste water can also be polluted to environment.Meanwhile, acid catalyzed reaction choosing
Selecting property is poor, side reaction is more, and the pair such as ether and sulfuric ester, sulfur dioxide is easily generated in acid condition
Product, while the separation and purification to product bring difficulty, also reduces the purity of yield and product,
The outward appearance and performance of product are influenceed, production cost is increased.Additionally, passing through acid catalyzed esterification technique system
Though can still there is micro catalysis in product through operations such as alkali cleaning, depicklings in the pentaerythritol ester for obtaining
Agent, part index (such as acid number, evaporation loss, breaking, oxidation stability) can not meet top grade
The requirement of lubricating oil.Simultaneously in order to remove the catalyst of residual, and the purity of synthetic ester is improved, typically
Using relatively complicated technical process (in a kind of preparation methods of pentaerythritol ester of the A of CN 103539664
Petrochemical industry limited company of state 2014).In addition to inorganic acid catalyst, toluene sulfonic acide (CN
A kind of preparation method Southern Yangtze University 2008 of PETOs of 101245006 A), pyrovinic acid
It is lanthanum (a kind of preparation method Du Xiaohan 2008 of pentaerythritol oleates of the A of CN 101314563), solid
Body acid (A of CN 104525269 be used for pentaerythrite esterification carried heteropoly acid solid catalyst and its
Preparation method and application Institute of Chemistry, Academia Sinica 2014), stannous chloride (CN 100341844
A kind of preparation method Zhang Xianming 2005 of pentaerythritol stearates of C) etc. be also used for catalyzing esterification mistake
Journey, although these catalyst can overcome some shortcomings of inorganic acid catalyst, has catalysis
The shortcomings of agent consumption is more, catalyst reusability is not good；And partial catalyst residual is in the product,
Product is caused during storage, easily generation qualitative change, product stability are poor.
Base catalysis is transesterification to prepare pentaerythritol fatty ester by fatty acid methyl ester and pentaerythrite reaction,
This method complex process, the reaction time is long, and esterification yield is not high, production cost (CN 103275306 also high
A kind of method Nanjing University of Technology that grease-based polyol is prepared by waste oil direct esterification ester exchange of A
2013；S Gryglewicz,W Piechocki,G Gryglewic.Preparation of polyol
esters based on vegetable and animal fat.Bioresource Technology,
87(2003),35-39.).The transesterification multiplex base catalyst of method synthesis of pentaerythritol ester, but alkalescence
Catalyst can occur saponification with fatty acid ester, can consume partial catalyst, unfavorable to reacting,
And limited by thermodynamics, ester interchange conversion rate is relatively low, therefore less someone is related to this respect
Research.
In sum, the degree of purity of base oil is to ensure the oil quality most important point, particularly with
Extremely harsh operating mode, this problem is particularly evident.In pentaerythritol ester building-up process, residual catalysis
During agent is often present in molecule in the form of the compound state, it is difficult to remove, to the high-temperature behavior band of oil product
Carry out fatal destruction, therefore it is to prepare an emphasis in pentaerythritol ester technique to remove residual catalyst.
A kind of B of CN 102260571 (aviation base oil PLA Air Force of the B of CN 102260571
Oil plant research institute 2013) the multistage esterification reaction tech of patent use, catalyst usage amount is greatly lowered
(being less than 100ppm), or even the use of catalyst is fully phased out, it is capable of achieving high conversion, low hydroxyl
The esterification effect of value, but the technical process is excessively cumbersome, and reaction time consumption is long.
The content of the invention
Self-catalytic esterification reaction is carried out it is an object of the invention to provide degassing is flowed under a kind of condition of negative pressure
The method for preparing bio-based pentaerythritol fatty ester.
To achieve the above object, the technical solution adopted by the present invention is：
A kind of preparation method of bio-based pentaerythritol fatty ester, by pentaerythrite and bio-based fat
Acid mixing, esterification prepares bio-based pentaerythritol fatty ester under negative pressure flowing degassing conditions.
Further, by raw material pentaerythrite and bio-based aliphatic acid with mol ratio be 1:4-1:8
Ratio mixes, and degassing esterification 2-4h is flowed at 130-240 DEG C, under 0-0.09MPa condition of negative pressure,
Reaction solution cooling separates dealcoholysis after esterification；Bio-based pentaerythrite is obtained by molecular distillation depickling
Fatty acid ester.
Further, by raw material pentaerythrite and bio-based aliphatic acid with mol ratio be 1:5-1:7
Ratio mixing, degassing esterification is flowed at 200-230 DEG C, under 0.04-0.05MPa condition of negative pressure anti-
Answer 2-4h, after esterification reaction solution be cooled to be not less than bio-based aliphatic acid used by esterification and its
The fusing point of pentaerythritol ester product, separates dealcoholysis；Bio-based Ji Wusi is obtained by molecular distillation depickling
Alcohol fatty acid ester.
Above-mentioned separation dealcoholysis obtains liquid reacting product and unreacted pentaerythrite solid, unreacted season
Repeated after the separated recovery of penta tetrol and utilized.Separated through molecular distillation after liquid reacting product, wherein：
Heavy constituent is bio-based pentaerythritol fatty ester product；Light component is unreacted bio-based aliphatic acid,
Repeated after the unreacted separated recovery of bio-based aliphatic acid and utilized.
It is inert gas that the flowing degassing is gases used；Such as, helium, argon gas or nitrogen.
The bio-based aliphatic acid mixes for glyceride stock with water, in 180-240 DEG C, pressure 3.5-5.5
Hydrolysis 4-6h under the conditions of MPa, after reaction reaction solution centrifugation or standing separation obtain croude fatty acids phase and
Glycerol liquor phase, separates the bio-based saturation or unsaturated lipid for obtaining different carbon numbers through rectifying after croude fatty acids
Fat acid.
The glyceride stock is waste grease or wood (grass) this unedible oil material crop crude oil.
The waste grease is waste oil, hogwash fat or acidification oil.
The bio-based saturation or unrighted acid of the different carbon numbers are stearic acid (C18:0), oleic acid
(C18:1), palmitic acid (C16:0)。
Inert gas is passed through before the bio-based unrighted acid and pentaerythrite esterification reaction, is replaced
Oxygen in system, then flows degassing esterification and prepares bio-based pentaerythritol resin under condition of negative pressure
Fat acid esters.
Specifically, bio-based unrighted acid is mixed into input reactor with pentaerythrite, sealing is anti-
Kettle is answered, inert gas is passed through, the air in displacement discharge system is unsaturated in esterification process to prevent
Key is oxidized by oxygen.It is that vacuum-pumping carries out the self-catalytic esterification that negative pressure is flowed under degassing conditions after deoxygenation
Reaction.
Advantage for present invention：
The present invention is the self-catalysis under conditions of negative pressure flowing degassing by pentaerythrite and bio-based aliphatic acid
The method that esterification prepares pentaerythritol fatty ester.The present invention with renewable biological source as raw material,
With sustainability and energy-conserving and environment-protective, product biodegradability is good；Its esterification is urged without additional
Agent, the catalysis that the conventional catalyst esterification techniques for generally using at present can be avoided to be remained in building-up process
The combination property of product is influenceed during agent is present in products molecule in the form of the compound state；Preparation technology letter
Easily, take short using negative pressure flowing degassing esterification, esterification degree is high, and side reaction is few；Separating-purifying
Process is simple, it is easy to control, product purity is high；The high temperature stability performance of product is good.
Brief description of the drawings
Fig. 1 is the thermogravimetric point of the bio-based pentaerythritol stearate product that the embodiment of the present invention 3 is provided
Analysis result figure.
Specific embodiment
With reference to specific embodiment, the invention will be further described, but the invention is not restricted in detail below
Embodiment.
Embodiment 1：Stearic acid and oleic acid are prepared by raw material of waste oil
The waste oil and water that will be treated through removal of impurities etc. by waste grease treatment plant add autoclave
In, capping kettle, regulation mixing speed is well mixed material, and being passed through steam pressurization makes system pressure
Power rises to 3.5MPa, and is heated to 220 DEG C, insulation hydrolysis 6h, reaction solution centrifugation after reaction
Separation respectively obtains upper strata croude fatty acids phase and lower floor's glycerol liquor phase, and the croude fatty acids that will be obtained are through molecule
Distillation is refined, and collects different fractions, respectively obtains stearic acid sterling and oleic acid sterling.
Embodiment 2：Palmitic acid is prepared by raw material of palm oil
By in palm oil and water addition autoclave, capping kettle, regulation mixing speed makes material
Well mixed, being passed through steam pressurization makes system pressure rise to 4.5MPa, and is heated to 210 DEG C,
Insulation hydrolysis 4h, reaction solution centrifugation respectively obtains upper strata croude fatty acids phase and lower floor's glycerine after reaction
Water phase, the croude fatty acids that will be obtained are refined through molecular distillation, obtain palmitic acid sterling.
Embodiment 3：The preparation of pentaerythritol stearate
By 100 grams of stearic acid (C obtained in embodiment 118:0) and during 8 grams of pentaerythrites add reactors,
Capping kettle, regulation mixing speed is well mixed material, vacuumizes maintenance system pressure 0.04
MPa, and it is heated to 230 DEG C, flowing degassing insulation reaction 4h.Reaction solution is cooled to after reaction
80 DEG C, natural subsidence or suction filtration isolate unreacted pentaerythrite solid and liquid reacting product, season
Repeated after the separated recovery of penta tetrol and utilized.Using molecular distillation to liquid reacting product separating-purifying,
Collect to obtain heavy constituent as pentaerythritol stearate product, product yield 95.2%, acid number 1.9
MgKOH/g, esterification degree 98.7% is divided the high-temperature stability of product using magnetic suspension balance thermogravimetric analyzer
Analysis result is as shown in Figure 1；Light component is unreacted stearic acid, can be after the separated recovery of stearic acid again
It is multiple to utilize.
As seen from Figure 1, the pentaerythritol stearate thermally-stabilised temperature of product highest prepared by embodiment 3
Degree is reachable 370 DEG C or so, with good heat endurance.
Embodiment 4：The preparation of pentaerythritol stearate
By 100 grams of stearic acid (C obtained in embodiment 118:0) and 11 grams of pentaerythrites addition reactors
In, capping kettle, regulation mixing speed is well mixed material, vacuumizes maintenance system pressure and exists
0.03MPa, and it is heated to 210 DEG C, flowing degassing insulation reaction 4h.Reaction solution after reaction
70 DEG C are cooled to, natural subsidence or suction filtration isolate unreacted pentaerythrite solid and liquid reactions are produced
Thing, repeats after the separated recovery of pentaerythrite and utilizes.Using molecular distillation to liquid reacting product point
From purification, heavy constituent as pentaerythritol stearate product, product yield 95.8%, acid number are collected to obtain
1.8mgKOH/g, esterification degree 98.7%；Light component is unreacted stearic acid, the separated recovery of stearic acid
Repeat afterwards and utilize.
Embodiment 5：The preparation of PETO
By 100 grams of oleic acid (C obtained in embodiment 118:1) and during 8 grams of pentaerythrites add reactors,
Capping kettle, regulation mixing speed is well mixed material.Before reaction, nitrogen is first passed through at room temperature,
For the air in displacement system, maintenance system pressure is vacuumized afterwards in 0.05MPa, and heat liter
Temperature flows degassing insulation reaction 4h to 200 DEG C.Reaction solution is cooled to 30 DEG C after reaction, sinks naturally
Drop or suction filtration isolate unreacted pentaerythrite solid and liquid reacting product, and pentaerythrite is separated
Repeated after recovery and utilized.Using molecular distillation to liquid reacting product separating-purifying, collecting to recombinate
Divide and be PETO product, product yield 95.6%, acid number 1.8mgKOH/g, esterification degree
98.8%；Light component is unreacted oleic acid, is repeated after the separated recovery of oleic acid and utilized.
Embodiment 6：The preparation of PETO
By 100 grams of oleic acid (C obtained in embodiment 118:1) and during 15 grams of pentaerythrites add reactors,
Capping kettle, regulation mixing speed is well mixed material, vacuumizes maintenance system pressure 0.04
MPa, and it is heated to 200 DEG C, flowing degassing insulation reaction 4h.Reaction solution is cooled to after reaction
25 DEG C, natural subsidence or suction filtration isolate unreacted pentaerythrite solid and liquid reacting product, season
Repeated after the separated recovery of penta tetrol and utilized.Using molecular distillation to liquid reacting product separating-purifying,
Collect to obtain heavy constituent as PETO product, product yield 95.2%, acid number 1.9mgKOH/g,
Esterification degree 98.7%；Light component is unreacted oleic acid, is repeated after the separated recovery of oleic acid and utilized.
Embodiment 7：The preparation of pentaerythrite palmitate
By 100 grams of palmitic acid (C obtained in embodiment 216:0) and during 9 grams of pentaerythrites add reactors,
Capping kettle, regulation mixing speed is well mixed material, vacuumizes maintenance system pressure 0.06
MPa, and it is heated to 220 DEG C, flowing degassing insulation reaction 4h.Reaction solution is cooled to after reaction
70 DEG C, natural subsidence or suction filtration isolate unreacted pentaerythrite solid and liquid reacting product, season
Repeated after the separated recovery of penta tetrol and utilized.Using molecular distillation to liquid reacting product separating-purifying,
Collect to obtain heavy constituent as pentaerythrite palmitate product, product yield 95.3%, acid number 1.6
MgKOH/g, esterification degree 98.8%；Light component is unreacted palmitic acid, can after the separated recovery of palmitic acid
Recycling.
Embodiment 8：The preparation of pentaerythrite palmitate
By 100 grams of palmitic acid (C obtained in embodiment 216:0) and 18 grams of pentaerythrites addition reactors
In, capping kettle, regulation mixing speed is well mixed material, vacuumizes maintenance system pressure and exists
0.05MPa, and it is heated to 210 DEG C, flowing degassing insulation reaction 4h.Reaction solution after reaction
65 DEG C are cooled to, natural subsidence or suction filtration isolate unreacted pentaerythrite solid and liquid reactions are produced
Thing, repeats after the separated recovery of pentaerythrite and utilizes.Using molecular distillation to liquid reacting product point
From purification, heavy constituent as pentaerythrite palmitate product, product yield 96.1%, acid number are collected to obtain
1.7mgKOH/g, esterification degree 98.6%；Light component is unreacted palmitic acid, the separated recovery of palmitic acid
Repeat afterwards and utilize.
Embodiment 9：Reclaim stearic recycling
By stearic acid isolated in pentaerythrite and embodiment 3 in molar ratio 1:6 ratio input
In reactor, capping kettle, regulation mixing speed is well mixed material, vacuumizes maintenance system
Pressure is heated to 230 DEG C, flowing degassing insulation reaction 4h in 0.04MPa.After reaction
Reaction solution is cooled to 80 DEG C, and natural subsidence or suction filtration isolate unreacted pentaerythrite solid and liquid
Product.Using molecular distillation to liquid reacting product separating-purifying, heavy constituent as season is collected to obtain
Penta tetrol stearate product, product yield 95.2%, acid number 1.8mgKOH/g, esterification degree 98.6%.
Embodiment 10：Reclaim recycling for pentaerythrite
By pentaerythrite isolated in stearic acid and embodiment 3-8 in molar ratio 5:1 ratio is thrown
Enter in reactor, capping kettle, regulation mixing speed is well mixed material, vacuumizes maintenance body
Be pressure in 0.05MPa, and be heated to 210 DEG C, flowing degassing insulation reaction 4h.Reaction
Reaction solution is cooled to 70 DEG C afterwards, and natural subsidence or suction filtration isolate unreacted pentaerythrite solid and liquid
Precursor reactant product.Using molecular distillation to liquid reacting product separating-purifying, collect heavy constituent is
Pentaerythritol stearate product, product yield 95.5%, acid number 1.9mgKOH/g, esterification degree 98.7%.
Claims (8)
1. a kind of preparation method of bio-based pentaerythritol fatty ester, it is characterised in that：By Ji Wusi
Alcohol mixes with bio-based aliphatic acid, and esterification prepares bio-based Ji Wusi under negative pressure flowing degassing conditions
Alcohol fatty acid ester.
2. the preparation method of the bio-based pentaerythritol fatty ester as described in claim 1, its feature
It is：By raw material pentaerythrite and bio-based aliphatic acid with mol ratio be 1:4-1:8 ratio mixing,
Degassing esterification 2-4h is flowed at 130-240 DEG C, under 0-0.09MPa condition of negative pressure, esterification is anti-
Should rear reaction solution cooling separation dealcoholysis；The fat acid of bio-based pentaerythrite is obtained by molecular distillation depickling
Ester.
3. the preparation method of the bio-based pentaerythritol fatty ester as described in claim 2, its feature
It is：By raw material pentaerythrite and bio-based aliphatic acid with mol ratio be 1:5-1:7 ratio mixing,
Degassing esterification 2-4h, esterification are flowed at 200-230 DEG C, under 0.04-0.05MPa condition of negative pressure
Reaction solution is cooled to and is not less than bio-based aliphatic acid used by esterification and its pentaerythritol ester product after reaction
The fusing point of product, separates dealcoholysis；Bio-based pentaerythritol fatty ester is obtained by molecular distillation depickling.
4. the preparation method of the bio-based pentaerythritol fatty ester as described in claim 1,2 or 3,
It is characterized in that：It is inert gas that the flowing degassing is gases used.
5. the preparation method of the bio-based pentaerythritol fatty ester as described in claim 1,2 or 3,
It is characterized in that：The bio-based aliphatic acid mixes for glyceride stock with water, in 180-240 DEG C, pressure
Hydrolysis 4-6h under the conditions of power 3.5-5.5MPa, reaction solution centrifugation or standing separation are obtained slightly after reaction
Aliphatic acid phase and glycerol liquor phase, the bio-based saturation for obtaining different carbon numbers is separated after croude fatty acids through rectifying
Or unrighted acid.
6. the preparation method of the bio-based pentaerythritol fatty ester as described in claim 5, its feature
It is：The glyceride stock is waste grease or wood (grass) this unedible oil material crop crude oil.
7. the preparation method of the bio-based pentaerythritol fatty ester as described in claim 5, its feature
It is：The bio-based saturation or unrighted acid of the different carbon numbers are stearic acid (C18:0), oleic acid
(C18:1), palmitic acid (C16:0)。
8. the preparation method of the bio-based pentaerythritol fatty ester as described in claim 5 or 7, its
It is characterised by：Inert gas is passed through before the bio-based unrighted acid and pentaerythrite esterification reaction,
Oxygen in displacement system, then flows degassing esterification and prepares bio-based Ji Wusi under condition of negative pressure
Alcohol fatty acid ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510828755.5A CN106748759A (en) | 2015-11-24 | 2015-11-24 | A kind of preparation method of bio-based pentaerythritol fatty ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510828755.5A CN106748759A (en) | 2015-11-24 | 2015-11-24 | A kind of preparation method of bio-based pentaerythritol fatty ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106748759A true CN106748759A (en) | 2017-05-31 |
Family
ID=58963926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510828755.5A Pending CN106748759A (en) | 2015-11-24 | 2015-11-24 | A kind of preparation method of bio-based pentaerythritol fatty ester |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106748759A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107501092A (en) * | 2017-08-21 | 2017-12-22 | 大连理工大学 | A kind of method that continuous decompression catalytic distillation prepares pentaerythrite ester base oil |
| CN109134247A (en) * | 2017-06-27 | 2019-01-04 | 中国石油天然气股份有限公司 | Preparation method and system of pentaerythritol ester |
| CN112500906A (en) * | 2020-12-14 | 2021-03-16 | 蓝德环保科技集团股份有限公司 | Method for producing high-viscosity-index biological lubricating oil base oil by using waste oil |
| CN112646079A (en) * | 2020-12-22 | 2021-04-13 | 黄山市强力化工有限公司 | High-dispersion lasting carbon deposition resistant synthetic ester base oil and preparation method thereof |
| CN113150264A (en) * | 2021-04-26 | 2021-07-23 | 南京威尔生物科技有限公司 | Preparation method of polyethylene glycol fatty acid ester |
| CN114426484A (en) * | 2022-01-21 | 2022-05-03 | 中国石油化工股份有限公司 | Synthetic method of pentaerythritol ester |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1449374A (en) * | 2000-09-11 | 2003-10-15 | 日本油脂株式会社 | Process for producing ester |
| CN100999463A (en) * | 2006-11-28 | 2007-07-18 | 王伟松 | Preparation method of pentaerythritol mixed acid ester |
| CN101062894A (en) * | 2006-04-28 | 2007-10-31 | 中国石油化工股份有限公司 | Esterification method of aliphatic acid |
| CN102875374A (en) * | 2012-02-28 | 2013-01-16 | 四川西普化工股份有限公司 | Method for producing pentaerythritol oleate under catalysis of granular solid superacid |
| CN103012138A (en) * | 2012-12-31 | 2013-04-03 | 齐河县齐翔化工有限公司 | Method for preparing pentaerythritol stearate (PETS) by using illegal cooking oil |
| CN103880668A (en) * | 2012-12-24 | 2014-06-25 | 青岛帅王油脂化学有限公司 | Pentaerythritol stearate preparation technology |
| CN103936695A (en) * | 2014-01-29 | 2014-07-23 | 张典华 | Nontoxic environmental protection plasticizer and preparation method thereof |
| CN104086412A (en) * | 2014-06-30 | 2014-10-08 | 海盐县精细化工有限公司 | Process method for producing butyl oleate by using rape oil fatty acid |
| CN104230706A (en) * | 2014-09-01 | 2014-12-24 | 安庆市中创生物工程有限公司 | Preparation method of pentaerythritol oleate |
| CN104471039A (en) * | 2012-05-18 | 2015-03-25 | 杜邦营养生物科学有限公司 | Ester compound of a polyoly and fatty acid oligomer for use as a cold flow improver in fuel compositions |
| CN104945247A (en) * | 2015-06-30 | 2015-09-30 | 百川化工(如皋)有限公司 | Preparation process of neopentyl polyol oleate |
-
2015
- 2015-11-24 CN CN201510828755.5A patent/CN106748759A/en active Pending
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1449374A (en) * | 2000-09-11 | 2003-10-15 | 日本油脂株式会社 | Process for producing ester |
| CN101062894A (en) * | 2006-04-28 | 2007-10-31 | 中国石油化工股份有限公司 | Esterification method of aliphatic acid |
| CN100999463A (en) * | 2006-11-28 | 2007-07-18 | 王伟松 | Preparation method of pentaerythritol mixed acid ester |
| CN102875374A (en) * | 2012-02-28 | 2013-01-16 | 四川西普化工股份有限公司 | Method for producing pentaerythritol oleate under catalysis of granular solid superacid |
| CN104471039A (en) * | 2012-05-18 | 2015-03-25 | 杜邦营养生物科学有限公司 | Ester compound of a polyoly and fatty acid oligomer for use as a cold flow improver in fuel compositions |
| CN103880668A (en) * | 2012-12-24 | 2014-06-25 | 青岛帅王油脂化学有限公司 | Pentaerythritol stearate preparation technology |
| CN103012138A (en) * | 2012-12-31 | 2013-04-03 | 齐河县齐翔化工有限公司 | Method for preparing pentaerythritol stearate (PETS) by using illegal cooking oil |
| CN103936695A (en) * | 2014-01-29 | 2014-07-23 | 张典华 | Nontoxic environmental protection plasticizer and preparation method thereof |
| CN104086412A (en) * | 2014-06-30 | 2014-10-08 | 海盐县精细化工有限公司 | Process method for producing butyl oleate by using rape oil fatty acid |
| CN104230706A (en) * | 2014-09-01 | 2014-12-24 | 安庆市中创生物工程有限公司 | Preparation method of pentaerythritol oleate |
| CN104945247A (en) * | 2015-06-30 | 2015-09-30 | 百川化工(如皋)有限公司 | Preparation process of neopentyl polyol oleate |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109134247A (en) * | 2017-06-27 | 2019-01-04 | 中国石油天然气股份有限公司 | Preparation method and system of pentaerythritol ester |
| CN109134247B (en) * | 2017-06-27 | 2022-03-29 | 中国石油天然气股份有限公司 | Preparation method and system of pentaerythritol ester |
| CN107501092A (en) * | 2017-08-21 | 2017-12-22 | 大连理工大学 | A kind of method that continuous decompression catalytic distillation prepares pentaerythrite ester base oil |
| CN112500906A (en) * | 2020-12-14 | 2021-03-16 | 蓝德环保科技集团股份有限公司 | Method for producing high-viscosity-index biological lubricating oil base oil by using waste oil |
| CN112646079A (en) * | 2020-12-22 | 2021-04-13 | 黄山市强力化工有限公司 | High-dispersion lasting carbon deposition resistant synthetic ester base oil and preparation method thereof |
| CN113150264A (en) * | 2021-04-26 | 2021-07-23 | 南京威尔生物科技有限公司 | Preparation method of polyethylene glycol fatty acid ester |
| CN114426484A (en) * | 2022-01-21 | 2022-05-03 | 中国石油化工股份有限公司 | Synthetic method of pentaerythritol ester |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106748759A (en) | A kind of preparation method of bio-based pentaerythritol fatty ester | |
| CN101906355B (en) | Method for preparing biodiesel by utilizing food waste recycling oil | |
| CN102627541A (en) | Technology for preparing hexanaphthene and cyclohexanone through cyclohexane oxidation and device thereof | |
| EP1944285A1 (en) | Method and apparatus for preparing fatty acid esters with alcohol recycling | |
| CN103193595B (en) | Ethylene glycol rectification device system and rectification technique in industry of producing ethylene glycol by synthesis gas | |
| CN105219480B (en) | A kind of pentaerythrite ester base oil and its synthetic method | |
| CN102803448A (en) | Biolubricant esters from the alcohols of unsaturated fatty acids | |
| CN101195572A (en) | Method for synthesizing fatty acid methyl ester | |
| CN100410349C (en) | Method for producing biological diesel oil through homogeneous successive reaction | |
| CN101591574B (en) | Method for preparing biodiesel by zirconia solid base catalyst | |
| CN100400622C (en) | Method of preparing biological diesel oil using solid base catalyst | |
| CN106349010A (en) | Method for producing cyclohexanol | |
| CN104447312A (en) | Dimethyl carbonate synthesis method | |
| CN101085929B (en) | Technique for producing biological diesel oil by Louis acid catalysis one-step method | |
| CN104449946B (en) | Method for preparing low-temperature environment-friendly lubricating oil from waste animal and vegetable oils | |
| CN106278879A (en) | A kind of preparation method of camellia oleosa seed oil base biological lubricant trimethylolpropane C18 fatty acid three ester | |
| CN101440298B (en) | Method for preparing -20 DEC C biodiesel from waste lipid by distillation process | |
| CN1810930A (en) | Technological process of preparing biological diesel oil continuously | |
| CN103772174B (en) | The method that acetone is prepared in aqueous isopropanol low-temperature gaseous phase dehydrogenation | |
| CN102649706B (en) | Method for preparing ethylene glycol through gas phase hydrogenation of oxalate | |
| CN106588657A (en) | Method for synthesizing dimethyl carbonate | |
| CN103224836B (en) | Pretreatment method of high impurity grease | |
| CN101423768A (en) | Method for preparing biodiesel by solid acid and base two-step catalysis method | |
| CN105331423B (en) | A kind of preparation method of high oxidation stability environmental friendly lubricant base oil | |
| CN101423767A (en) | Method for preparing biodiesel by alcohol extraction and solid base catalysis two-step method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170531 |
|
| RJ01 | Rejection of invention patent application after publication |