CN106565470A - Preparation method for diisononyl cyclohexane-1,2-dicarboxylate - Google Patents
Preparation method for diisononyl cyclohexane-1,2-dicarboxylate Download PDFInfo
- Publication number
- CN106565470A CN106565470A CN201510656238.4A CN201510656238A CN106565470A CN 106565470 A CN106565470 A CN 106565470A CN 201510656238 A CN201510656238 A CN 201510656238A CN 106565470 A CN106565470 A CN 106565470A
- Authority
- CN
- China
- Prior art keywords
- time
- temperature
- staying
- stripping
- phthalic anhydride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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
-
- 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 invention provides a preparation method for diisononyl cyclohexane-1,2-dicarboxylate. The preparation method comprises the following steps: 1) adding hexahydrophthalic anhydride, isononanol and acetic anhydride into a reaction vessel at the same time, carrying out heating to 180 to 300 DEG C and then carrying out stirring and dehydration for 2 to 5 h, wherein a mol ratio of hexahydrophthalic anhydride to isononanol is 1: (2-5), and the addition amount of acetic anhydride is 1 to 10% of the mass of hexahydrophthalic anhydride; 2) removing excess alcohol through flash evaporation by using a falling-film evaporator at a negative pressure of -0.02 MPa to 0.096 MPa, wherein retention time is 0.001 to 0.05 h; 3) introducing water vapor and nitrogen into a stripping tank for bubbling and removing low-molecular-weight impurities in a material 2 through evaporation; and 4) adding active carbon accounting for 1 to 10% of the mass of a material 3 into a decoloring kettle and carrying out decoloring and filtering so as to obtain the final product diisononyl cyclohexane-1,2-dicarboxylate, wherein yield reaches 98.5% and purity reaches 99.8%. According to the invention, a single-step high-temperature esterification process is employed, so reaction time is greatly shortened; excess alcohol is removed through pressure-reduced flash evaporation, so energy consumption is lowered, and the phenomenon of emulsification is avoided; and neutralization and washing are not needed, so alkaline waste water is not produced, and the preparation method is suitable for large-scale industrial production.
Description
Technical field
The invention belongs to Field of Fine Chemicals category, is that one kind prepares novel environment-friendlyplasticizer plasticizer hexamethylene -1, the novel method of 2- dioctyl phthalate dinonyls.
Background technology
Hexamethylene -1,2- dioctyl phthalate dinonyls（Another name：Hexahydro phthalic acid dinonyl, referred to as：DINCH）It is a kind of emerging safety and environmental protection plasticizer, with the structure similar with diisononyl phthalate (DINP) and dioctyl phthalate (DOP) and performance, is mainly used in：Medicines, packaging for foodstuff, toy for children and child care product, it is often more important that the product of its plasticising in natural environment can voluntarily biodegradation, do not cause environmental pollution, the safe and sanitary being beneficial to man is the favorable substitutes of benzene carboxylic acid ester plasticizer.Therefore, develop efficient, nontoxic, degradable plasticizer new product traditional category is substituted into trend of the times.
At present, synthesizing cyclohexane 1 alkane -1, the main method of 2- dioctyl phthalate dinonyls (DINCH) include directed hydrogenation, direct esterification and ester-interchange method.
The production technology of external DINCH is directed hydrogenation, directly diisononyl phthalate (DINP) is hydrogenated as hexamethylene -1,2- dioctyl phthalate dinonyls (DINCH) under high temperature, high pressure using precious metal catalysts such as nickel, platinum, palladium, rhodium, rutheniums.The processing technology routine is simple, cleaning, but very high to equipment and catalyst requirement, and investment is big.
United States Patent (USP) US628917 and US6888021 disclose the process of hydrogenation method, with hydrogenation as manufacture method, hydrogenation is carried out to diisononyl phthalate, 50 ~ 250 DEG C of reaction temperature, 20 ~ 300bar of pressure, catalyst comprising be applied to the metal of at least one the VIIIth race of periodic chart transition containing huge hole support body individually or with the metal of at least one periodic chart transition the Ith or VIII race together as active metal catalyst.Although this legal system is made DINCH and can avoid three-waste pollution, need high-pressure hydrogenation, response time length, high cost, hydrogenation high pressure equipment expensive.
Direct esterification has two lines, and one is first with lower temperature（120~160℃）Hexahydro phthalic anhydride and isononyl alcohol are carried out into single-esterification, the different nonyl ester of middle species hexamethylene -1- formic acid -2- formic acid is generated, and temperature being improved afterwards to 250 DEG C and adding catalyst carries out dehydration esterification (Fig. 1)；Another route is with the direct high temperature of one step（250℃）Esterification（Fig. 2）.The present invention makes the response time shorten to 5 h by 16 h using one step high temperature esterification method, is effectively shortened processing time, saves the energy.
The manufacture method of esterification is disclosed in United States Patent (USP) US6310235, esterification is carried out in the presence of the metal solvent such as titanium system or stannum system, esterification is reacted in two stages, first with lower temperature（120~160℃）Carry out single-esterification, temperature is improved afterwards to 250 DEG C and adds catalyst carries out double esterification reaction, reaction is neutralized with the hydroxide aqueous solution of alkali metal or alkaline-earth metal after the completion of reaction, the removing of excessive response alcohol is carried out afterwards, it is dried, filters the carboxylate for being prepared into plasticizer, this technological reaction is for up to 16 h.
Chinese patent CN1962736A is disclosed with one step high temperature esterification method synthesizing cyclohexane 1 alkane 1, the method of 2- dioctyl phthalate dinonyls, the method with tetra isopropyl titanate as catalyst, 250 DEG C of reaction temperature, 5 h reaction pressures of response time, 5 ~ 760 mbar, removes moisture；Then through neutralization, washing, dealcoholysis, filtration, decolouring, obtain product DINCH.
The country is adapted to adopt esterification process, and compared to high-pressure hydrogenation, equipment requirements are low, and catalyst low cost, response time are short.Domestic device uses for reference the one step high temperature esterification method of CN1962736, greatly shortens the response time, but first neutralizes dealcoholysis again, consumes big and ester and the easy emulsifying of the water capacity, is unfavorable for layering, and product colourity is high.Strict with environmental requirement, substantial amounts of neutralization, washing waste water also increased very big burden to enterprise.
The content of the invention
In order to overcome the deficiencies in the prior art, it is an object of the invention to provide a kind of energy consumption is low, low cost, raw material availability height, good product quality, eco-friendly synthesizing cyclohexane 1 alkane -1, the method for 2- dioctyl phthalate dinonyls.
The present invention adopts one step high temperature esterification method, will raw material hexahydro phthalic anhydride, isononyl alcohol and catalyst simultaneously add and under reactor normal pressure, carry out heating esterification, esterification time can be effectively shortened in border ring dehydration in side；After dehydration terminates, direct dealcoholysis, using falling film evaporator, under reduced pressure by the heat contained by itself, alcohol excess is fallen in flash vaporization, and alcohol is discharged from tower top evaporation, and condensed device condensation cycle is used, and the thick ester after dealcoholysis is flowed out from bottom；Then refined, using vapor and nitrogen bubble, under negative pressure, low molecular weight impurities are steamed；Finally, add activated carbon to carry out adsorption bleaching, be filtrated to get final products, synthesis technique schematic flow sheet is shown in Fig. 3, and installation drawing is shown in Fig. 4.
One kind prepares hexamethylene -1 using one step high temperature esterification method, and the method for 2- dioctyl phthalate dinonyls is comprised the following steps that：
1）Hexahydro phthalic anhydride and isononyl alcohol, acetic anhydride are added in reactor simultaneously, wherein hexahydro phthalic anhydride and isononyl alcohol mol ratio are 1:2 ~ 5, acetic anhydride addition is the 1% ~ 10% of hexahydro phthalic anhydride quality, is heated to 200 ~ 260 DEG C, stirring 2 ~ 6 h of dehydration, obtains material 1, and material 1 is hexamethylene -1,2- dioctyl phthalate dinonyl crude products；
2）By material 1 through falling film evaporator, the excessive alcohol of flash distillation removing under the negative pressure of -0.02MPa ~ 0.096MPa, the time of staying is 0.001 ~ 0.01 h, obtains material 2, into stripping tank；
3）Vapor and nitrogen bubble are passed through in stripping tank, low molecular weight impurities in material 2 are steamed, is obtained material 3, into decolouring kettle.In -0.02MPa ~ 0.096MPa, at 40 ~ 90 DEG C, material 2 is controlled in 0.5 ~ 1 h stripping tank temperature control the control of stripping pressure tank in the time of staying of stripping tank；
4）The activated carbon of 3 mass 1% ~ 10% of material is added in decolouring kettle, is decolourized in 50 ~ 90 DEG C of 0.5 ~ 3.5 h of stirring of temperature, is filtered, obtain final products hexamethylene -1,2- dioctyl phthalate dinonyls.
The step（1）In, preferred hexahydro phthalic anhydride and isononyl alcohol mol ratio are 1:2 ~ 3, preferred acetic anhydride addition for hexahydro phthalic anhydride quality 1% ~ 5%, not 220 ~ 250 DEG C of preferred heating-up temperature, preferred stirring dewatering time is 3 ~ 4 h.
The step（2）In, preferred negative pressure is -0.04MPa ~ 0.096MPa, and the preferred time of staying is 0. 001 ~ 0.01 h.
The step（3）In, preferred stripping pressure tank is -0.06MPa ~ 0.08MPa, and preferred temperature is 60 ~ 90 DEG C, and the preferred time of staying is 0.5 ~ 1 h.
The step（4）In, preferred activated carbon addition for 3 mass of material 1% ~ 3%, preferred temperature are 70 ~ 90 DEG C, and the preferred time of staying is 0.5 ~ 1 h, and preferred filter is filter centrifugal.
Using preferred condition, the yield of final products can reach 98.5%, and purity reaches 99.8%
The present invention is had the advantage that compared with hydrogenation technique：
1）The use of acetic anhydride is catalyst, cheap and easy to get, catalysis activity is good, non-environmental-pollution, it is to avoid use noble metal catalyst, has saved cost；
2）Synthesis under normal pressure, it is simple to operate, without the need for extra equipment investment；
3）The not exclusively produced benzene homologues residual of hydrogenation reaction is avoided, it is safer；
The present invention is had the advantage that compared with traditional esterifications technique：
1）Using one step high temperature esterification method, anhydride promotes to react to the movement of positive reaction direction with reaction water generating acetic acid, and the response time foreshortens to 2 ~ 5 h by 16 h of two-step method, greatly shortens the response time；
2）At reduced pressure conditions by the heat contained by itself, flash vaporization alcohol excess reduces energy consumption；
3）First steam alcohol reprocessing process compared with first neutralization washing steams alcohol again, it is to avoid emulsion, alleviate post processing pressure；
4）Low boiling impurity is removed using vapor and nitrogen stripping method for refining, without neutralization, washing, no alkaline waste water produces, reaches the effect of energy-saving and emission-reduction, reduce environmental protection pressure.
5）Using centrifugal type filter, large-scale commercial production can be adapted to improve production efficiency and yield.
Description of the drawings
Fig. 1 is double esterification method synthetic route；Fig. 2 is one step esterification process synthetic route；Fig. 3 is embodiment DINCH synthesis technique schematic flow sheet；Fig. 4 is embodiment DINCH synthesis technique schematic device.
Specific embodiment
Embodiment
1
Put into hexahydro phthalic anhydride, isononyl alcohol, catalyst acetic acid acid anhydride in a kettle. in proportion, wherein：HHPA is 1 with the mol ratio of isononyl alcohol:2.3, acetic anhydride addition for HHPA quality 5%, heated and stirred under normal pressure are warmed up to 180 DEG C of backflows and start timing, continue temperature reaction, obtain material 1 after maintaining 3 h at 230 DEG C, and material 1 is hexamethylene -1,2- dioctyl phthalate dinonyl crude products；By material 1 through falling film evaporator, the excessive alcohol of flash distillation removing under the negative pressure of -0.06MPa, the time of staying is 0.002
H, obtains material 2, into stripping tank；Vapor and nitrogen bubble are passed through in stripping tank, low molecular weight impurities in material 2 are steamed, is obtained material 3, into decolouring kettle.In -0.05MPa, at 80 ~ 90 DEG C, material 2 is controlled in 0.5 h stripping tank temperature control the control of stripping pressure tank in the time of staying of stripping tank；4）The activated carbon of 3 mass 3% of material is added in decolouring kettle, is decolourized in 90 DEG C of temperature, 1.5 h of stirring, is filtered, obtain final products hexamethylene -1,2- dioctyl phthalate dinonyls, product is colourless transparent oil liquid, yield 98.5%, purity 99.8%.
Comparative example 1
Esterification is carried out with two benches difference processing procedure, first stage first carries out single-esterification, first 1 mole of hexahydro phthalic anhydride, 154 g and 2.6 moles of 370 g of isononyl alcohol are added in 1000 ml four-hole boiling flasks before reaction, it is not added with catalyst, single-esterification is carried out with 140 DEG C, monoesters can be formed after 1 h completely.Second stage carries out double esterification reaction, by temperature by 140 DEG C be promoted to 230 DEG C and add raw material gross mass 0.5% 26 g of tetra isopropyl titanate, reaction 16 h dehydration complete.
Comparative example 2
With one step high temperature esterification method, by 1 mole of hexahydro phthalic anhydride, 154 g and 2.6 moles of 370 g of isononyl alcohol and 2.6 g of catalyst tetra isopropyl titanate, while adding 1000
In ml four-hole boiling flasks, it is warming up to 180 DEG C and starts the timing that flows back, be dehydrated after 5 h and complete.
Embodiment
2
Put into hexahydro phthalic anhydride, isononyl alcohol, catalyst acetic acid acid anhydride in a kettle. in proportion, wherein：HHPA is 1 with the mol ratio of isononyl alcohol:2.1, acetic anhydride addition for HHPA quality 2%, heated and stirred under normal pressure are warmed up to 180 DEG C of backflows and start timing, continue temperature reaction, obtain material 1 after maintaining 3 h at 220 DEG C, and material 1 is hexamethylene -1,2- dioctyl phthalate dinonyl crude products；By material 1 through falling film evaporator, the excessive alcohol of flash distillation removing under the negative pressure of -0.08MPa, the time of staying is 0.001
H, obtains material 2, into stripping tank；Vapor and nitrogen bubble are passed through in stripping tank, low molecular weight impurities in material 2 are steamed, is obtained material 3, into decolouring kettle.In -0.04MPa, at 70 ~ 80 DEG C, material 2 is controlled in 1 h stripping tank temperature control the control of stripping pressure tank in the time of staying of stripping tank；4）The activated carbon of 3 mass 10% of material is added in decolouring kettle, is decolourized in 90 DEG C of temperature, 1.5 h of stirring, is filtered, obtain final products hexamethylene -1,2- dioctyl phthalate dinonyls, product is colourless transparent oil liquid, yield 95.2%, purity 99.8%.
Embodiment
3
Put into hexahydro phthalic anhydride, isononyl alcohol, catalyst acetic acid acid anhydride in a kettle. in proportion, wherein：HHPA is 1 with the mol ratio of isononyl alcohol:2.5, acetic anhydride addition for HHPA quality 6%, heated and stirred under normal pressure are warmed up to 180 DEG C of backflows and start timing, continue temperature reaction, obtain material 1 after maintaining 5 h at 250 DEG C, and material 1 is hexamethylene -1,2- dioctyl phthalate dinonyl crude products；By material 1 through falling film evaporator, the excessive alcohol of flash distillation removing under the negative pressure of -0.096MPa, the time of staying is 0.001
H, obtains material 2, into stripping tank；Vapor and nitrogen bubble are passed through in stripping tank, low molecular weight impurities in material 2 are steamed, is obtained material 3, into decolouring kettle.In -0.08MPa, at 60 ~ 70 DEG C, material 2 is controlled in 1 h stripping tank temperature control the control of stripping pressure tank in the time of staying of stripping tank；4）The activated carbon of 3 mass 1% of material is added in decolouring kettle, is decolourized in 90 DEG C of temperature, 1.5 h of stirring, is filtered, obtain final products hexamethylene -1,2- dioctyl phthalate dinonyls, product is colourless transparent oil liquid, yield 96.5%, purity 99.6%.
Embodiment
4
Put into hexahydro phthalic anhydride, isononyl alcohol, catalyst acetic acid acid anhydride in a kettle. in proportion, wherein：HHPA is 1 with the mol ratio of isononyl alcohol:2.7, acetic anhydride addition for HHPA quality 5%, heated and stirred under normal pressure are warmed up to 180 DEG C of backflows and start timing, continue temperature reaction, obtain material 1 after maintaining 3 h at 240 DEG C, and material 1 is hexamethylene -1,2- dioctyl phthalate dinonyl crude products；By material 1 through falling film evaporator, the excessive alcohol of flash distillation removing under the negative pressure of -0.06MPa, the time of staying is 0.001
H, obtains material 2, into stripping tank；Vapor and nitrogen bubble are passed through in stripping tank, low molecular weight impurities in material 2 are steamed, is obtained material 3, into decolouring kettle.In -0.05MPa, at 80 ~ 90 DEG C, material 2 is controlled in 1.5 h stripping tank temperature control the control of stripping pressure tank in the time of staying of stripping tank；4）The activated carbon of 3 mass 5% of material is added in decolouring kettle, is decolourized in 90 DEG C of temperature, 0.5 h of stirring, is filtered, obtain final products hexamethylene -1,2- dioctyl phthalate dinonyls, product is colourless transparent oil liquid, yield 97.5%, purity 99.2%.
Protection scope of the present invention is not limited only to above example, mentions on every claims, and the deformation that those skilled in the art can be extrapolated to is in protection domain.
Claims (8)
1. a kind of hexamethylene -1, the method for 2- dioctyl phthalate dinonyls, its feature are comprised the following steps：1）Hexahydro phthalic anhydride and isononyl alcohol, catalyst are added in reactor simultaneously, wherein hexahydro phthalic anhydride and isononyl alcohol mol ratio are 1:2 ~ 5, catalyst charge is the 1% ~ 10% of hexahydro phthalic anhydride quality, is heated to 200 ~ 260 DEG C, stirring 2 ~ 5 h of dehydration, obtains material 1, and material 1 is hexamethylene -1,2- dioctyl phthalate dinonyl crude products；2）By material 1 through falling film evaporator, the excessive alcohol of flash distillation removing under the negative pressure of -0.02MPa ~ 0.096MPa, the time of staying is 0.001 ~ 0.05 h, obtains material 2, into stripping tank；3）Vapor and nitrogen bubble are passed through in stripping tank, low molecular weight impurities in material 2 are steamed, is obtained material 3, into decolouring kettle, in -0.02MPa ~ 0.096MPa, at 40 ~ 90 DEG C, material 2 is controlled in 0.5 ~ 1 h stripping tank temperature control the control of stripping pressure tank in the time of staying of stripping tank；4）The activated carbon of 3 mass 1% ~ 10% of material is added in decolouring kettle, is decolourized in 50 ~ 90 DEG C of 0.5 ~ 3.5 h of stirring of temperature, is filtered, obtain final products hexamethylene -1,2- dioctyl phthalate dinonyls.
2. method according to claim 1, is characterized in that the step（1）In, catalyst is acetic anhydride.
3. method according to claim 1, is characterized in that the step（1）In, the addition of catalyst is the 1% ~ 5% of hexahydro phthalic anhydride mass fraction.
4. method according to claim 1, is characterized in that the step（1）In, hexahydro phthalic anhydride and isononyl alcohol mol ratio are 1:2 ~ 3,220 ~ 250 DEG C of heating-up temperature, stirring dewatering time are 3 ~ 4 h.
5. method according to claim 1, is characterized in that the step（2）In, negative pressure is -0.04MPa ~ 0.096MPa, and the time of staying is 0. 001 ~ 0.01 h.
6. method according to claim 1, is characterized in that the step（3）In, stripping pressure tank is -0.06MPa ~ 0.08MPa, and temperature is 60 ~ 90 DEG C, and the time of staying is 0.5 ~ 1 h.
7. method according to claim 1, is characterized in that the step（4）In, activated carbon addition for 3 mass of material 1% ~ 3%, temperature are 70 ~ 90 DEG C, and the time of staying is 0.5 ~ 1 h.
8. method according to claim 1, is characterized in that the step（4）In, filter is filter centrifugal.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510656238.4A CN106565470B (en) | 2015-10-12 | 2015-10-12 | A kind of preparation method of hexamethylene -1,2- dioctyl phthalate dinonyl |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510656238.4A CN106565470B (en) | 2015-10-12 | 2015-10-12 | A kind of preparation method of hexamethylene -1,2- dioctyl phthalate dinonyl |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106565470A true CN106565470A (en) | 2017-04-19 |
| CN106565470B CN106565470B (en) | 2019-08-02 |
Family
ID=58508099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510656238.4A Active CN106565470B (en) | 2015-10-12 | 2015-10-12 | A kind of preparation method of hexamethylene -1,2- dioctyl phthalate dinonyl |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106565470B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114014758A (en) * | 2021-10-26 | 2022-02-08 | 中石化南京化工研究院有限公司 | Decolorization method of plasticizer DINCH product |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101417950A (en) * | 2008-10-27 | 2009-04-29 | 中国科学院大连化学物理研究所 | Method for preparing 1,2-cyclohexane cyclohexanedimethanol dibasic ester |
| CN101774919A (en) * | 2010-02-04 | 2010-07-14 | 江南大学 | Method for preparing cyclohexane 1,2-dicarboxylate using organic acid as catalyst |
| CN102701980A (en) * | 2012-06-29 | 2012-10-03 | 太仓市新星轻工助剂厂 | Synthetic method of environmental-friendly plasticizer hexahydrobenzene diisononyl phthalate |
-
2015
- 2015-10-12 CN CN201510656238.4A patent/CN106565470B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101417950A (en) * | 2008-10-27 | 2009-04-29 | 中国科学院大连化学物理研究所 | Method for preparing 1,2-cyclohexane cyclohexanedimethanol dibasic ester |
| CN101774919A (en) * | 2010-02-04 | 2010-07-14 | 江南大学 | Method for preparing cyclohexane 1,2-dicarboxylate using organic acid as catalyst |
| CN102701980A (en) * | 2012-06-29 | 2012-10-03 | 太仓市新星轻工助剂厂 | Synthetic method of environmental-friendly plasticizer hexahydrobenzene diisononyl phthalate |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114014758A (en) * | 2021-10-26 | 2022-02-08 | 中石化南京化工研究院有限公司 | Decolorization method of plasticizer DINCH product |
| CN114014758B (en) * | 2021-10-26 | 2023-12-29 | 中石化南京化工研究院有限公司 | Decoloring method of plasticizer DINCH product |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106565470B (en) | 2019-08-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111960943A (en) | Process for producing dioctyl terephthalate by semi-continuous method | |
| CN101812044A (en) | Method and system for extracting and separating natural VE from plant oil deodorizing distillate | |
| CN102807547B (en) | New process for extracting vitamin E and sterol from soybean oil deodorization distillate | |
| CN103435642B (en) | Production method of trioctyl phosphate | |
| CN108129423A (en) | A kind of method for preparing α-acetyl-gamma-butyrolacton | |
| CN106565470A (en) | Preparation method for diisononyl cyclohexane-1,2-dicarboxylate | |
| CN103772186B (en) | A kind of process for purification of fermentation organic acid | |
| CN106748774B (en) | Refining method of cyclohexane diformate plasticizer | |
| KR20130107472A (en) | Method for preparing high-purified unsaturated fatty acids using waste animal and vegetable oil | |
| CN103524525B (en) | The method extracting arteannuinic acid and derivative thereof waste is produced from Artemisinin | |
| CN115557928B (en) | Synthesis method of 2-chlorothiophene-5-formic acid | |
| CN102633640B (en) | Integrated production technique of acetyl tributyl citrate (ATBC) | |
| CN102329221B (en) | Method for preparing isostearic acid | |
| CN105315158A (en) | Combined process method for preparing naphthenic base dioctyl phthalate dibasic ester | |
| CN109456172B (en) | Method for purifying dodecanedioic acid in water phase | |
| CN109704958B (en) | Method for preparing ethyl butyrate and catalyst used in method | |
| CN102876461B (en) | Method for synthetising epoxy fatty glyceride by using unsaturated monoglyceride | |
| CN101671334B (en) | Production technology of pamabrom | |
| CN206279107U (en) | A kind of Steam soak dehydration technique is used for the device of synthesizing citric acid triethyl | |
| CN111187174A (en) | Production and purification method of fatty acyl glycinate or fatty derivative acyl glycinate | |
| CN109534996A (en) | A kind of technique that Butyl acetylpropanoate is produced as raw material using cellulose | |
| CN103274932B (en) | Method for recovering organic acids from dilute acid solution | |
| CN112251296B (en) | Method for preparing conjugated linoleic acid glyceride through solid base catalysis direct esterification | |
| CN106946698A (en) | A kind of method that utilization macromolecule loading mesoporous catalyst prepares triacetyl glycerine | |
| CN114890869A (en) | Refining and deodorizing method of 1, 3-butanediol |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP01 | Change in the name or title of a patent holder | ||
| CP01 | Change in the name or title of a patent holder |
Address after: Liuhe District of Nanjing City, Jiangsu province 210048 geguan Road No. 699 Patentee after: China Petroleum & Chemical Corp. Patentee after: SINOPEC NANJING CHEMICAL RESEARCH INSTITUTE Co.,Ltd. Address before: Liuhe District of Nanjing City, Jiangsu province 210048 geguan Road No. 699 Patentee before: China Petroleum & Chemical Corp. Patentee before: Nanhua Group Research Institute |