CN108863785A - A kind of low pour point pentaerythritol oleate mixed ester and its synthetic method - Google Patents
A kind of low pour point pentaerythritol oleate mixed ester and its synthetic method Download PDFInfo
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- CN108863785A CN108863785A CN201810825061.XA CN201810825061A CN108863785A CN 108863785 A CN108863785 A CN 108863785A CN 201810825061 A CN201810825061 A CN 201810825061A CN 108863785 A CN108863785 A CN 108863785A
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- oleic acid
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/58—Esters of straight chain acids with eighteen carbon atoms in the acid moiety
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/60—Maleic acid esters; Fumaric acid esters
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/64—Environmental friendly compositions
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The invention discloses a kind of low pour point pentaerythritol oleate mixed esters, its main component is three oleic acid maleic acid monoester mixed ester of pentaerythrite, the oleic acid moieties of three Long carbon chains are kept in the structure, it introduces the cis-double bonds structure of maleic acid simultaneously or double bond structure adds branched structure, so that double bond quantity increases in unit mass or branched structure increases, to reduce pour point.Its synthetic method includes the following steps：It is first that 3 addition oleic acid and pentaerythrite are reacted with pentaerythrite molar ratio by oleic acid；Maleic acid monoester is added, the complete hydroxyl of unreacted is all closed；Cooling after fully reacting, washing sloughs water entrainer, obtains three oleic acid maleic acid monoester mixed ester of pale yellowish oil transparency liquid pentaerythrite.The present invention is pentaerythrite oleic acid maleic acid monoester mixed ester by two step esterification synthesis of pentaerythritol oleic acid mixed esters, main ingredient, and product viscosity is lower than pentaerythritol tetraoleate, and pour point is lower than pentaerythritol oleate；Chinese raw materials of the present invention is cheap and easy to get simultaneously, performance is stable, easy to operate, industrial easy to accomplish.
Description
Technical field
The present invention relates to fine organic chemical industry field, specifically a kind of low pour point pentaerythritol oleate mixed ester and its conjunction
At method.
Background technique
Pentaerythritol tetraoleate has excellent greasy property, and resisting combustibility is good, volatilizees low, biological degradation rate is greater than
90%, -32 DEG C of pour point.The base that may be used as the synthesis base oil of ester type fire resistant hydraulic oil, aviation engine lubricating oil of high-quality
Plinth oil.
Low temperature flow is an important performance of lubricating oil, is indicated with pour point.Pour point refers to oil product in defined test
Under the conditions of, the flowable minimum temperature of cooled sample.The high oil product of pour point is not suitable in cold district application.Esters oil
Low temperature flow it is related with structure, document《Contemporary chemical industry》The phase P1570-1572 of volume 44 the 7th《The structure of lubricating oil in esters is to property
It can influence research》In show that, for diester compound, the low temperature fluidity of oil product can be improved in the branching of both ends carbochain, separately
Outside, the presence of double bond can improve the low temperature fluidity of oil product to a certain extent.Chinese invention patent application CN 107735484A
In, the trihydroxymethylpropanyl ester of C9 or C10 monocarboxylic acid has been synthesized, has wherein included 5-15mol% branched acids in C9 or C10 monocarboxylic acid
With 85-95mol% straight-chain acid（Total mole number relative to monocarboxylic acid）.If n-nonanoic acid and 3,5,5 Trimethylhexanoic acid molar ratio are 9:
When 1, trimethylolpropane mixed ester pour point is lower than -54 DEG C.Using the 2- propyl of collateralization in Chinese patent CN102203225B
Enanthic acid and pentaerythrite, trimethylolpropane direct esterification, respectively obtain four 2- propylheptanoic acid esters of pentaerythrite（Four ester contents
97~98%）, trimethylolpropane three 2- propylheptanoic acid esters（Three ester contents 97%）, the two pour point is all very low, and respectively -56 DEG C
With -52 DEG C, but the viscosity index (VI) of the two is all smaller, the former 110, and the latter 89, and biological degradation rate is not reported, and it is not high to belong to quality
Esters oil.Document《Lubrication and sealing》The phase P1-3 of volume 36 the 2nd《The synthesis of pentaerythrite oleic acid acrylic acid mixed ester and performance are ground
Study carefully》In pentaerythrite oleic acid acrylic acid mixing ester polymer is synthesized by two-step process.The first step：Pentaerythrite, oleic acid, acrylic acid
One pot reaction obtains mixed ester；Second step：In the presence of initiator azo isobutyronitrile, acrylic double bond polymerization.It is used in the first step
Saturated sodium bicarbonate solution washing, distillation water-washing method depickling.But the acrylic acid introduced in the document is unstable structure, quite
In terminal olefin, terminal olefin is easy polymerization, and leading to oil product, viscosity gradually rises in use, eventually even polymerize
Object precipitating.
The prior art indicate that pentaerythritol tetraoleate is base oil of good performance, synthetic method has document report
Road.Pentaerythritol tetraoleate structure is transformed, maleic acid monoester structure is introduced, obtains the pentaerythrite oleic acid of low pour point
The work of maleic acid monoester mixed ester has no document report.
Summary of the invention
The purpose of the present invention is to provide one kind with biological degradation rate height, viscosity is high, volatilization is low, flash-point is high, viscosity refers to
Number height, the low-down pentaerythritol oleate mixed ester of pour point and its synthetic method.
The technical solution adopted by the present invention is that：A kind of low pour point pentaerythritol oleate mixed ester, it is characterised in that:It is led
Wanting ingredient is three oleic acid maleic acid monoester mixed ester of pentaerythrite, keeps the oleic acid moieties of three Long carbon chains in the structure, simultaneously
The cis-double bonds structure or double bond structure for introducing maleic acid add branched structure, so that the increase of double bond quantity or branch in unit mass
Structure increases, to reduce pour point.
The synthetic method of low pour point pentaerythritol oleate mixed ester of the present invention, includes the following steps：The first step presses oleic acid
It is 3 addition oleic acid and pentaerythrite with pentaerythrite molar ratio, is reacted under conditions of catalyst, water entrainer is added；The
Two steps add maleic acid monoester, the complete hydroxyl of unreacted are all closed, wherein oleic acid：Pentaerythrite：Maleic acid monoester
Molar ratio be 3：1：1.1~1.2；It is cooled to room temperature, washes after third step fully reacting, organic layer in vacuo is sloughed water entrainer, obtained
To three oleic acid maleic acid monoester mixed ester of pale yellowish oil transparency liquid pentaerythrite.
Maleic acid monoester of the present invention refer to maleic acid monoester refer to monomethyl maleate, ethyl maleate,
Citraconic acid mono-methyl, citraconic acid mono ethyl ester, 2,3- dimethyl maleic acid mono-methyl, 2,3- dimethyl maleic acid list second
One of ester or a variety of mixtures.
Catalyst of the present invention is p-methyl benzenesulfonic acid, and dosage is the 5 ‰ of oleic acid mass fraction；The water entrainer is petroleum
Ether.
The heating temperature of the first step of the present invention is 110-140 DEG C, and preferably 130-135 DEG C, the reaction time is that 2.0-6.0 is small
When, preferably 3.0h；Second step reaction temperature is 110-140 DEG C, and preferably 130-135 DEG C, the reaction time is that 1.0-3.0 is small
When, preferably 2.0h.
The present invention uses two step esterification synthesis of pentaerythritol trioleate maleic acid monoester mixed esters.It is specific as follows：
The first step：The material ratio for being 3 by oleic acid and pentaerythrite molar ratio, is added oleic acid and pentaerythrite, mainly generates season penta
Tetrol trioleate includes a small amount of pentaerythritol tetraoleate and pentaerythrite dioleate：
Second step：Maleic acid monoester is added, hydroxyl remaining in pentaerythrite trioleate molecule is closed, generates Ji Wusi
Three oleic acid maleic acid monoester mixed ester of alcohol：
。
The introducing of branched structure or double bond (especially cis-double bonds) is destroyed the symmetry of molecules align by the present invention,
So that crystallization temperature reduces, pour point is reduced.Maleic acid molecular weight is smaller than oleic acid, has cis-double bonds structure, 2,3- dimethyl horses
There are also branches in addition to cis-double bonds in next sour structure.1194,4 oleic acid double bonds of pentaerythritol tetraoleate molecular weight, average matter
There is a double bond in amount 298.5.One of products therefrom of the present invention pentaerythrite trioleate monomethyl maleate mixing ester molecule
1040 and 4 double bonds are measured, have a double bond in average quality 260, it is seen that double bond increases in unit mass, therefore the present invention
Obtained three oleic acid maleic acid monoester mixed ester of pentaerythrite has lower pour point.Maleic acid chemical property is stablized, and double bond is not
It is easy to oxidize, it is not easy to polymerize.
Innovation of the invention is that three oleic acid maleic acid monoester mixed ester of pentaerythrite keeps three long in the structure
The oleic acid moieties of carbochain to guarantee high viscosity, high viscosity index (HVI) and high biological degradation rate, while introducing the cis-double bonds of maleic acid
Structure or double bond structure add branched structure, since maleic acid molecular weight is smaller so that in unit mass double bond quantity increase or
Branched structure increases, to reduce pour point.
Product is obtained with unique high-quality using this method：High biological degradation rate, high viscosity, low volatilization, high-flash,
High viscosity index (HVI) and low pour point.Its main component is three oleic acid maleic acid monoester mixed ester of pentaerythrite, separately containing a small amount of season penta
Four oleate of tetrol, a small amount of two oleic acid of pentaerythrite, two maleic acid monoester mixed ester, mixture do not need to be separated.Simultaneously in the present invention
Raw material are cheap and easy to get, performance is stable, easy to operate, industrial easy to accomplish.
Specific embodiment
Below according to specific embodiment, the invention will be further described：
Embodiment 1：
136.2g pentaerythrite is successively added in the reactor, catalyst is added in the oleic acid of 847.3g, and water entrainer controls oil bath
It 130-135 DEG C of heating temperature, under nitrogen protection, is stirred at reflux, divides water 3.0 ~ 4.0 hours, it is slightly cold, then plus 143.1g maleic acid list
Methyl esters is warming up to 130-135 DEG C, and stirring divides water 2 hours.It is cooled to room temperature, washes after fully reacting, organic layer in vacuo sloughs band
Aqua obtains pale yellowish oil transparency liquid, and biological degradation rate is greater than 90%, and pour point is less than -40 DEG C, yield 99%.
Embodiment 2：
136.2g pentaerythrite is successively added in the reactor, catalyst is added in the oleic acid of 847.3g, and water entrainer controls oil bath
It 130-135 DEG C of heating temperature, under nitrogen protection, is stirred at reflux, divides water 3.0 ~ 4.0 hours, it is slightly cold, then plus 158.5g maleic acid list
Ethyl ester is warming up to 130-135 DEG C, and stirring divides water 2 hours.It is cooled to room temperature, washes after fully reacting, organic layer in vacuo sloughs band
Aqua obtains pale yellowish oil transparency liquid, and biological degradation rate is greater than 90%, and pour point is less than -40 DEG C, yield 99%.
Embodiment 3：
136.2g pentaerythrite is successively added in the reactor, catalyst is added in the oleic acid of 847.3g, and water entrainer controls oil bath
It 130-135 DEG C of heating temperature, under nitrogen protection, is stirred at reflux, divides water 3.0 ~ 4.0 hours, it is slightly cold, then plus 173.9g 2,3- bis-
Citraconic acid mono-methyl is warming up to 130-135 DEG C, and stirring divides water 2 hours.It is cooled to room temperature, washes after fully reacting, it is organic
Layer vacuum sloughs water entrainer, obtains pale yellowish oil transparency liquid, and biological degradation rate is greater than 90%, and pour point is less than -40 DEG C, yield
99%。
Embodiment 4：
136.2g pentaerythrite is successively added in the reactor, catalyst is added in the oleic acid of 847.3g, and water entrainer controls oil bath
It 130-135 DEG C of heating temperature, under nitrogen protection, is stirred at reflux, divides water 3.0 ~ 4.0 hours, it is slightly cold, then plus 71.6g maleic acid list
Methyl esters and 87.0g 2,3- dimethyl maleic acid mono-methyl are warming up to 130-135 DEG C, and stirring divides water 2 hours.It is cold after fully reacting
But it to room temperature, washes, organic layer in vacuo sloughs water entrainer, obtains pale yellowish oil transparency liquid, and biological degradation rate is greater than 90%,
Pour point is less than -40 DEG C, yield 99%.
Embodiment of the present invention is not only the description carried out to the preferred embodiment of the present invention, not to this hair
Bright conception and scope is defined, and under the premise of not departing from design philosophy of the present invention, engineers and technicians are to this in this field
The all variations and modifications that the technical solution of invention is made, should all fall into protection scope of the present invention, and the present invention is claimed
Technology contents are all described in the claims.
Claims (6)
1. a kind of low pour point pentaerythritol oleate mixed ester, it is characterised in that：Its main component is three oleic acid horse of pentaerythrite
Carry out acid monoester mixed ester, keep the oleic acid moieties of three Long carbon chains in the structure, while introducing the cis-double bonds structure of maleic acid
Or double bond structure adds branched structure, so that double bond quantity increases in unit mass or branched structure increases, to reduce pour point.
2. the synthetic method of low pour point pentaerythritol oleate mixed ester as described in claim 1, it is characterised in that including as follows
Step：The first step is 3 oleic acid and pentaerythrite to be added by oleic acid and pentaerythrite molar ratio, and catalyst, water entrainer is being added
Under the conditions of reacted；Second step adds maleic acid monoester, the complete hydroxyl of unreacted is all closed, wherein oleic acid：Season
Penta tetrol：The molar ratio of maleic acid monoester is 3：1：1.1~1.2；It is cooled to room temperature, washes, organic layer after third step fully reacting
Vacuum sloughs water entrainer, obtains three oleic acid maleic acid monoester mixed ester of pale yellowish oil transparency liquid pentaerythrite.
3. synthetic method according to claim 2, it is characterised in that：The maleic acid monoester refers to maleic acid list first
Ester, ethyl maleate, citraconic acid mono-methyl, citraconic acid mono ethyl ester, 2,3- dimethyl maleic acid mono-methyl, 2,3-
One of dimethyl maleic acid mono ethyl ester or a variety of mixtures.
4. synthetic method according to claim 2, it is characterised in that：The catalyst is p-methyl benzenesulfonic acid, and dosage is oil
The 5 ‰ of acid mass fraction；The water entrainer is petroleum ether.
5. synthetic method according to claim 2, it is characterised in that：The heating temperature of the first step is 110-140 DEG C, reaction
Time is 2.0-6.0 hours；Second step reaction temperature is 110-140 DEG C, and the reaction time is 1.0-3.0 hours.
6. synthetic method according to claim 5, it is characterised in that：First step heating temperature is 130-135 DEG C, when reaction
Between be 3.0h；Second step reaction temperature is 130-135 DEG C, reaction time 2.0h.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110143872A (en) * | 2019-06-18 | 2019-08-20 | 山东海川化工技术研究院有限公司 | The preparation method of neopentyl polyol ester |
| CN115417765A (en) * | 2022-09-23 | 2022-12-02 | 新乡市瑞丰新材料股份有限公司 | Low-pour-point pentaerythritol oleic acid composite ester and preparation method thereof |
| CN118165777A (en) * | 2024-03-14 | 2024-06-11 | 沧州中克油脂有限公司 | High-quality pentaerythritol oleate and preparation method and application thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH041156A (en) * | 1990-04-18 | 1992-01-06 | Lion Corp | Production of ester |
| US20140343316A1 (en) * | 2011-05-13 | 2014-11-20 | Thomas W. Theyson | Esters Of Structurally Symmetric Alkoxylated Polyols And Applications Thereof |
| 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 |
| CN105143420A (en) * | 2013-03-12 | 2015-12-09 | 埃莱万斯可再生能源科学股份有限公司 | Maleinized ester derivatives |
| CN105189441A (en) * | 2013-02-28 | 2015-12-23 | 马来西亚国家石油公司 | The preparation of biopolyol esters for lubricant application |
| CN105481692A (en) * | 2015-11-30 | 2016-04-13 | 诺泰生物科技(合肥)有限公司 | Synthetic method of chlorinated pentaerythritol organic acid ester, and application of chlorinated pentaerythritol organic acid ester in special oil |
-
2018
- 2018-07-25 CN CN201810825061.XA patent/CN108863785B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH041156A (en) * | 1990-04-18 | 1992-01-06 | Lion Corp | Production of ester |
| US20140343316A1 (en) * | 2011-05-13 | 2014-11-20 | Thomas W. Theyson | Esters Of Structurally Symmetric Alkoxylated Polyols And Applications Thereof |
| CN105189441A (en) * | 2013-02-28 | 2015-12-23 | 马来西亚国家石油公司 | The preparation of biopolyol esters for lubricant application |
| CN105143420A (en) * | 2013-03-12 | 2015-12-09 | 埃莱万斯可再生能源科学股份有限公司 | Maleinized ester derivatives |
| 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 |
| CN105481692A (en) * | 2015-11-30 | 2016-04-13 | 诺泰生物科技(合肥)有限公司 | Synthetic method of chlorinated pentaerythritol organic acid ester, and application of chlorinated pentaerythritol organic acid ester in special oil |
Non-Patent Citations (1)
| Title |
|---|
| 尤龙刚等: "季戊四醇油酸丙烯酸混合酯的合成及性能研究", 《润滑与密封》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110143872A (en) * | 2019-06-18 | 2019-08-20 | 山东海川化工技术研究院有限公司 | The preparation method of neopentyl polyol ester |
| CN115417765A (en) * | 2022-09-23 | 2022-12-02 | 新乡市瑞丰新材料股份有限公司 | Low-pour-point pentaerythritol oleic acid composite ester and preparation method thereof |
| CN118165777A (en) * | 2024-03-14 | 2024-06-11 | 沧州中克油脂有限公司 | High-quality pentaerythritol oleate and preparation method and application thereof |
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