CN109627167A - IA/AEO-4 dibasic acid esters and its preparation and application - Google Patents
IA/AEO-4 dibasic acid esters and its preparation and application Download PDFInfo
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- CN109627167A CN109627167A CN201811550781.6A CN201811550781A CN109627167A CN 109627167 A CN109627167 A CN 109627167A CN 201811550781 A CN201811550781 A CN 201811550781A CN 109627167 A CN109627167 A CN 109627167A
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- itaconic anhydride
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- 239000002253 acid Substances 0.000 title claims abstract description 47
- 150000002148 esters Chemical class 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000005886 esterification reaction Methods 0.000 claims abstract description 177
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims abstract description 114
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 230000032050 esterification Effects 0.000 claims description 74
- 239000002994 raw material Substances 0.000 claims description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
- 239000003054 catalyst Substances 0.000 claims description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 28
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 11
- 230000008859 change Effects 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 6
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000010257 thawing Methods 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 9
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 238000011160 research Methods 0.000 abstract description 4
- 238000011156 evaluation Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 31
- 239000003921 oil Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000693 micelle Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 235000011087 fumaric acid Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WRLRISOTNFYPMU-UHFFFAOYSA-N [S].CC1=CC=CC=C1 Chemical compound [S].CC1=CC=CC=C1 WRLRISOTNFYPMU-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- -1 dilute Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention relates to organic chemical synthesis fields, more particularly to IA/AEO-4 dibasic acid esters and its preparation and application.Present invention optimizes the double esterification reaction of itaconic anhydride and AEO-4, optimal reaction condition and higher yield have been obtained, and Lab-evaluation has been carried out to its surface-active and interfacial activity.The surface and interface superior activity of gained dibasic acid esters product IA/AEO-4.For such itaconic anhydride polymerisable emulsifier, following research direction is not turn off sending structure innovation, more excellent performance of kind and opens up its application field, to and realize industrialized production.
Description
Technical field
The present invention relates to organic chemical synthesis fields, more particularly to IA/AEO-4 dibasic acid esters and its preparation and application.
Background technique
Compared with conventional emulsifier, polymerisable emulsifier further includes a reactive official other than with hydrophilic and oleophilic base
It can roll into a ball, this reactive functional groups can participate in emulsion polymerization, can be in a manner of covalent bond while playing the role of emulsifier
It is bonded to polymer particle surface, becomes a part of polymer, emulsifier is avoided and is desorbed from polymer particle or in cream
It is migrated in glue film, to improve stability of emulsion.
Itaconic acid anhydride emulsifier is exactly a kind of reactive emulsifier of function admirable, and reactivity is moderate, can be fine
Be bonded in emulsion particle surface, be seldom embedded in inside emulsion particle, and be not easy homopolymerization, not will form water-soluble polymer,
Flocculated generation is avoided, is the hot spot of current research.Mainly there are itaconic anhydride type, maleic anhydride type, maleate type, Malaysia
Acid amide type and Boletic acid type, wherein itaconic anhydride is the hot spot studied and difficult point with reacting for fatty alcohol.
There is an urgent need to research and develop surface-active and the better emulsifier of interfacial activity.
Summary of the invention
In view of the foregoing deficiencies of prior art, the purpose of the present invention is to provide a kind of IA/AEO-4 dibasic acid esters and its systems
It is standby with application, for solving the problems of the prior art.
In order to achieve the above objects and other related objects, the present invention adopts the following technical scheme:
The first aspect of the present invention provides a kind of compound, and the structural formula of the compound is as shown in formula II.
The structural formula as shown in formula II are as follows:
It is described herein as, it in the present invention, can be bis- by structural formula such as II compound represented of formula, referred to as IA/AEO-4
Ester.By structural formula such as I compound represented of formula, referred to as IA/AEO-4 monoesters.
The second aspect of the present invention provides a kind of structural formula such as II compound represented of formula as described in the first aspect of the invention
Preparation method, include the following steps:
(1) using itaconic anhydride and AEO-4 as raw material, single-esterification generates type I compound, and reaction equation is as follows:
(2) type I compound and AEO-4, under the catalysis of catalyst, II compound of double esterification reaction production, reaction side
Formula is as follows:
In the present invention, AEO-4 is to be to chemical structural formulaCompound abbreviation.
In a kind of embodiment, in step (1), mono-esterification temperature >=80 DEG C of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 80~100 DEG C.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 80~95 DEG C.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 80~90 DEG C.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 80~85 DEG C.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 80 DEG C.
In a kind of embodiment, in step (1), mono-esterification temperature >=85 DEG C of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 85~100 DEG C.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 85~95 DEG C.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 85~90 DEG C.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 85 DEG C.
In a kind of embodiment, in step (1), mono-esterification temperature >=90 DEG C of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 90~100 DEG C.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 90~95 DEG C.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 90 DEG C.
In a kind of embodiment, in step (1), mono-esterification temperature >=95 DEG C of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 95~100 DEG C.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 95 DEG C.
In a kind of embodiment, in step (1), mono-esterification temperature >=100 DEG C of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification temperature of itaconic anhydride and AEO-4 are 100 DEG C.
In a kind of embodiment, in step (1), mono-esterification time >=1h of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1~4.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1~4h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1~3.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1~3h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1~2.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1~2h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1~1.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1h.
In a kind of embodiment, in step (1), mono-esterification time >=1.5h of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1.5h~4.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1.5h~4h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1.5h~3.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1.5h~3h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1.5h~2.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1.5h~2h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 1.5h.
In a kind of embodiment, in step (1), mono-esterification time >=2h of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 2h~4.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 2h~4h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 2h~3.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 2h~3h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 2h~2.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 2h.
In a kind of embodiment, in step (1), mono-esterification time >=2.5h of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 2.5h~4.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 2.5h~4h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 2.5h~3.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 2.5h~3h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 2.5h.
In a kind of embodiment, in step (1), mono-esterification time >=3h of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 3h~4.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 3h~4h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 3h~3.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 3h.
In a kind of embodiment, in step (1), mono-esterification time >=3.5h of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 3.5h~4.5h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 3.5h~4h.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 3.5h.
In a kind of embodiment, in step (1), mono-esterification time >=4h of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 4h~4.5h.
In a kind of embodiment, in step (1), mono-esterification time >=4.5h of itaconic anhydride and AEO-4.
In a kind of embodiment, in step (1), the mono-esterification time of itaconic anhydride and AEO-4 are 4.5h.
In a kind of embodiment, in step (1), molar ratio >=2 of AEO-4 and itaconic anhydride usage amount.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2~2.3.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2~2.2.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2~2.1.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2~2.05.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2.
In a kind of embodiment, in step (1), molar ratio >=2.05 of AEO-4 and itaconic anhydride usage amount.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2.05~2.3.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2.05~2.2.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2.05~2.1.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2.05.
In a kind of embodiment, in step (1), molar ratio >=2.1 of AEO-4 and itaconic anhydride usage amount.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2.1~2.3.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2.1~2.2.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2.1.
In a kind of embodiment, in step (1), molar ratio >=2.2 of AEO-4 and itaconic anhydride usage amount.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2.2~2.3.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2.2.
In a kind of embodiment, in step (1), molar ratio >=2.3 of AEO-4 and itaconic anhydride usage amount.
In a kind of embodiment, in step (1), the molar ratio of AEO-4 and itaconic anhydride usage amount is 2.3.
In a kind of embodiment, in step (2), the catalyst is selected from p-methyl benzenesulfonic acid.
Those skilled in the art can be according to the type of reaction system and catalyst, the dosage of appropriate adjustment catalyst.
In a kind of embodiment, the dosage of the catalyst is 0.5% or more of total mass of raw material.
It should be noted that the total mass of raw material refers to itaconic anhydride and the quality sum of AEO-4.
In a kind of embodiment, the dosage of the catalyst is the 0.5%~2.5% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 0.5%~2% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 0.5%~1.5% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 0.5%~1% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 0.5% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is 1% or more of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 1%~2.5% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 1%~2% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 1%~1.5% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 1% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is 1.5% or more of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 1.5%~2.5% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 1.5%~2% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 1.5% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is 2% or more of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 2%~2.5% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 2% of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is 2.5% or more of total mass of raw material.
In a kind of embodiment, the dosage of the catalyst is the 2.5% of total mass of raw material.
In a kind of embodiment, in step (2), when reaction, it is generated to remove double esterification reaction to be additionally added water entrainer
Water.
In a kind of embodiment, the water entrainer is selected from toluene.
In a kind of embodiment, the water entrainer dosage is 1 times or more of total mass of raw material.
It should be noted that the total mass of raw material refers to itaconic anhydride and the quality sum of AEO-4.
In a kind of embodiment, the water entrainer dosage is 1~4 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 1~3.5 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 1~3 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 1~2.5 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 1~2 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 1~1.5 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 1 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is the 2 times or more of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 2~4 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 2~3.5 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 2~3 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 2~2.5 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 2 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 3 times or more of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 3~4 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 3~3.5 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 3 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage be total mass of raw material 3.5~times or more.
In a kind of embodiment, the water entrainer dosage is 3.5~4 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 3.5 times of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 4 times or more of total mass of raw material.
In a kind of embodiment, the water entrainer dosage is 4 times of total mass of raw material.
In a kind of embodiment, in step (2), double esterification temperature >=110 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 110~150 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 110~140 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 110~130 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 110~120 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 110 DEG C.
In a kind of embodiment, in step (2), double esterification temperature >=120 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 120~150 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 120~140 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 120~130 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 120 DEG C.
In a kind of embodiment, in step (2), double esterification temperature >=130 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 130~150 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 130~140 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 130 DEG C.
In a kind of embodiment, in step (2), double esterification temperature >=140 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 140~150 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 140 DEG C.
In a kind of embodiment, in step (2), double esterification temperature >=150 DEG C.
In a kind of embodiment, in step (2), double esterification temperature is 150 DEG C.
In a kind of embodiment, in step (2), the double esterification time >=0.5h.
In a kind of embodiment, in step (2), the double esterification time is 0.5~3h.
In a kind of embodiment, in step (2), the double esterification time is 0.5~2.5h.
In a kind of embodiment, in step (2), the double esterification time is 0.5~2h.
In a kind of embodiment, in step (2), the double esterification time is 0.5~1.5h.
In a kind of embodiment, in step (2), the double esterification time is 0.5~1h.
In a kind of embodiment, in step (2), the double esterification time is 0.5h.
In a kind of embodiment, in step (2), the double esterification time >=1h.
In a kind of embodiment, in step (2), the double esterification time is 1~3h.
In a kind of embodiment, in step (2), the double esterification time is 1~2.5h.
In a kind of embodiment, in step (2), the double esterification time is 1~2h.
In a kind of embodiment, in step (2), the double esterification time is 1~1.5h.
In a kind of embodiment, in step (2), the double esterification time is 1h.
In a kind of embodiment, in step (2), the double esterification time >=1.5h.
In a kind of embodiment, in step (2), the double esterification time is 1.5~3h.
In a kind of embodiment, in step (2), the double esterification time is 1.5~2.5h.
In a kind of embodiment, in step (2), the double esterification time is 1.5~2h.
In a kind of embodiment, in step (2), the double esterification time is 1.5h.
In a kind of embodiment, in step (2), the double esterification time >=2h.
In a kind of embodiment, in step (2), the double esterification time is 2~3h.
In a kind of embodiment, in step (2), the double esterification time is 2~2.5h.
In a kind of embodiment, in step (2), the double esterification time is 2h.
In a kind of embodiment, in step (2), the double esterification time >=2.5h.
In a kind of embodiment, in step (2), the double esterification time is 2.5~3h.
In a kind of embodiment, in step (2), the double esterification time is 2.5h.
In a kind of embodiment, in step (2), the double esterification time >=3h.
In a kind of embodiment, in step (2), the double esterification time is 3h.
In a kind of embodiment, the preparation method, comprising steps of at a temperature of single-esterification, into reaction vessel
A certain amount of itaconic anhydride is added, after itaconic anhydride thawing, a certain amount of AEO-4 is added, first carries out single-esterification process,
Double esterification temperature is then heated to, a certain amount of catalyst is added and carries out double esterification reaction.
In a kind of embodiment, after being warming up to double esterification temperature, a certain amount of catalyst is added and water entrainer carries out dibasic acid esters
Change reaction.
In a kind of embodiment, the dibasic acid esters product of acquisition is purified, comprising steps of after double esterification reaction,
Water entrainer therein is removed, neutralizes unreacted itaconic anhydride IA and IA/AEO-4 monoesters later, it is dry using washing.
In a kind of embodiment, Na is added2CO3In saturated solution and unreacted itaconic anhydride IA and IA/AEO-4 monoesters.
The third aspect of the present invention provides a kind of compound that the method as described in second aspect prepares.
The fourth aspect of the present invention, provides compound described in first aspect or the method as described in second aspect prepares
Compound be used to prepare the purposes in emulsifier.
The fifth aspect of the present invention, provides compound described in first aspect or the method as described in second aspect prepares
Compound be used to prepare the purposes in surfactant.
In addition, IA/AEO-4 dibasic acid esters of the invention has lower critical micelle concentration (cmc), oil, hydrosphere can effectively reduce
Face tension, and there is O/W emulsifying effectiveness simultaneously, there is wide application prospect in field of oil development.
Compared with prior art, the invention has the following beneficial effects:
The present invention provides a kind of IA/AEO-4 dibasic acid esters simply, fast synthesis method, forms similar Gemini surface active agent
Active material, reactivity is moderate, and preparation process is simple, can carry out industrialized production.Pass through being greatly lowered of dibasic acid esters
It closes object critical micelle concentration (cmc), improves compound heatproof, salt resistant character, it is living to be effectively improved oil, water termination using dibasic acid esters characteristic
Property, interfacial tension is greatly lowered.The AEO-4 class formation of introducing also has good emulsification of crude oil effect.Dibasic acid esters of the present invention produces
Object is expected to be efficiently applied to field of oil development.
Detailed description of the invention
Fig. 1: the influence of mono-esterification temperature and mono-esterification time to IA/AEO-4 system mono-ester product yield.
Fig. 2: influence of the water entrainer toluene dosage to IA/AEO-4 system dibasic acid esters products collection efficiency.
Fig. 3: influence of the feed ratio to dibasic acid esters products collection efficiency.
Fig. 4: influence of the p-methyl benzenesulfonic acid dosage to dibasic acid esters products collection efficiency.
Fig. 5: the influence of double esterification temperature and double esterification time to IA/AEO-4 system dibasic acid esters products collection efficiency.
Specific embodiment
Illustrate embodiments of the present invention below by way of specific specific example, those skilled in the art can be by this specification
Other advantages and efficacy of the present invention can be easily understood for disclosed content.The present invention can also pass through in addition different specific realities
The mode of applying is embodied or practiced, the various details in this specification can also based on different viewpoints and application, without departing from
Various modifications or alterations are carried out under spirit of the invention.
It should be clear that in the following example not specifically dated process equipment or device be all made of conventional equipment in the art or
Device.
In addition, it should also be understood that, one or more method and step mentioned in the present invention does not repel before and after the combination step
It can also be inserted into other methods step there may also be other methods step or between these explicitly mentioned steps, unless separately
It is described；It should also be understood that the combination connection relationship between one or more equipment/device mentioned in the present invention is not repelled
The two equipment/devices specifically mentioned before and after the unit equipment/device there may also be other equipment/device or at these it
Between can also be inserted into other equipment/device, unless otherwise indicated.Moreover, unless otherwise indicated, the number of various method steps is only
Identify the convenient tool of various method steps, rather than for the arrangement order of limitation various method steps or limits the enforceable model of the present invention
It encloses, relativeness is altered or modified, and without material changes in technical content, when being also considered as, the present invention is enforceable
Scope.
The synthesis of 1 IA/AEO-4 dibasic acid esters of embodiment
In the present invention, IA/AEO-4 monoesters refers to that structural formula such as I compound represented of formula, IA/AEO-4 dibasic acid esters refer to knot
Structure formula such as II compound represented of formula.
The preparation method of structural formula such as II compound represented of formula, includes the following steps:
(1) using itaconic anhydride and AEO-4 as raw material, single-esterification generates type I compound, and reaction equation is as follows:
(2) type I compound and AEO-4, under the catalysis of catalyst, II compound of double esterification reaction production, reaction side
Formula is as follows:
Reaction mechanism are as follows: itaconic anhydride is five-membered cyclic compound, and the presence of conjugated double bond keeps ring atom as far as possible
In same plane, thus energy is higher, and when by electrophilic reagent attack, polarization deformation occurs for the pi-electron cloud of conjugated system, altogether
Occur being alternately distributed for cloud density size on yoke chain.Under the attack of AEO-4, ring-opening reaction is very easy to, thus monoesters
Change process is an irreversible reaction, and reaction rate is very fast, can still be carried out under no catalysts conditions.
And double esterification reaction is reversible esterification, reaction rate is slower, needs to improve reaction temperature, using catalyst
And the water of generation is discharged in time, the time for reaching balance could be shortened, improve conversion ratio.
Used instrument includes: with reagent in the present embodiment
Rotary Evaporators, Japanese EYELA；Nicolet infrared spectrometer, U.S. Thermo Fisher；T50 automatically drips
Determine instrument, Switzerland Mettler Toledo；The full-automatic surface tension instrument of K100, GermanyTX-500C gamut rotation drop circle
Face tensiometer, U.S. CNG；
Itaconic anhydride, AEO-4 (have been removed water), anhydrous sodium acetate, p-methyl benzenesulfonic acid, sodium hydroxide, toluene, sodium carbonate, north
Capital perseverance dimerization work；Crude oil, domestic reservoirs in one oilfield in western China crude oil.
Specifically, the synthesis process such as II compound represented of formula is as follows in a kind of embodiment:
Oil bath is warming up to single-esterification temperature, and a certain amount of itaconic anhydride is added into the four-hole bottle equipped with blender
A certain amount of AEO-4 is added after it melts in IA, carries out single-esterification process, first to reduce catalyst amount.Then it rises
Temperature is to double esterification temperature and loads onto water segregator and condenser pipe, be added a certain amount of catalyst p-methyl benzenesulfonic acid and water entrainer toluene into
Row double esterification reaction, when the water yield in water segregator no longer changes, as reaction end, timing sampling are analyzed.
The purifying of dibasic acid esters product: after double esterification reaction, toluene therein is removed in rotation, and Na is added later2CO3Saturated solution
Unreacted itaconic anhydride IA and IA/AEO-4 monoesters are neutralized, it is dry using washing, obtain the higher dibasic acid esters product of purity
IA/AEO-4 dibasic acid esters.
Results and discussion:
1, dibasic acid esters Product formation condition optimizing:
1.1, the influence of mono-esterification temperature and mono-esterification time
Fixed feeding area ratio n (AEO-4): n (IA)=2.1, system is investigated at a temperature of different mono-esterifications, and monoesters yield is with list
The situation of change of esterification time.It is analyzed by taking IA/AEO-4 reaction system as an example.It is learnt by Fig. 1 result, for IA/AEO-4
System, when mono-esterification temperature is greater than 80 DEG C, the monoesters yield in 1h can reach 80% or more；With the liter of mono-esterification temperature
Height, final monoesters yield are gradually increased, and required reaction time shortens, but when temperature is greater than 95 DEG C, on the continuing of temperature
It rises on monoesters yield and reaction time without influence.
1.2, the influence of water entrainer toluene dosage
Fixed feeding area ratio n (AEO-4): n (IA)=2.1, mono-esterification temperature is 95 DEG C, and the mono-esterification time is 1h, double esterification
Temperature is 140 DEG C, and catalyst p-methyl benzenesulfonic acid dosage is the 1.5% of raw material total amount, investigates water entrainer toluene dosage and produces to dibasic acid esters
The influence of produce rate.It is analyzed by taking IA/AEO-4 reaction system as an example.As seen from Figure 2, for IA/AEO-4 reactant
System, best toluene dosage is about 2 times of total mass of raw material.Toluene dosage is very little, cannot effectively take the water of generation out of；Toluene is used
Amount is too big, reduces the concentration of reactant, reduces yield and extends the reaction time.
1.3, the influence of feed ratio
Fixed water entrainer toluene dosage is 2 times of total mass of raw material, and double esterification temperature is 140 DEG C, to catalyst toluene sulphur
Sour dosage is the 1.5% of raw material total amount.Due to AEO-4 excess, it can promote double esterification reaction and carry out to the right, increase yield, so
It selects to investigate influence of the feed ratio to yield when the molar ratio of AEO-4 and IA >=2.As seen from Figure 3, as AEO-4 and IA
Molar ratio when being greater than 2.1, AEO-4 dosage is continued growing on yield substantially without influence, it is thus determined that optimal feed ratio is n
(AEO-4)): n (IA)=2.1.
1.4, the influence of catalyst amount
The common catalyst of double esterification reaction has the concentrated sulfuric acid, anhydrous sodium acetate and p-methyl benzenesulfonic acid etc., and the concentrated sulfuric acid is strong
Corrosivity limits its application；Anhydrous sodium acetate finds that no water is separated out in experimentation, illustrates its catalysis as catalyst
It is active inadequate.We select catalyst of the non-corrosive and active higher p-methyl benzenesulfonic acid as double esterification reaction.It can by Fig. 4
To find out, when p-methyl benzenesulfonic acid dosage is smaller, with the increase of its dosage, yield is gradually increased, but when its dosage increases to
When certain value, yield is no longer changed.For IA/AEO-4 system, the optimum amount of p-methyl benzenesulfonic acid is total mass of raw material
1.5%.
1.5, the influence of double esterification temperature and double esterification time
Fixed feeding area ratio n (AEO-4)): n (IA)=2.1, water entrainer toluene dosage are 2 times of total mass of raw material, catalyst
P-methyl benzenesulfonic acid dosage be total mass of raw material 1.5%, investigate at a temperature of different double esterifications, yield with the double esterification time change
Change situation, is analyzed by taking IA/AEO-4 reaction system as an example.As seen from Figure 5, for IA/AEO-4 system, double esterification temperature
When degree is lower than 140 DEG C, yield is very low, and less than 40%, and the required reaction time is longer.When temperature is increased to 140 DEG C, after 1h
Yield just reach 70% or more, temperature increases again, and less, and temperature is too high, maleic acid may be made to tautomerize to for yield variation
Fumaric acid, dehydration of alcohols generate the by-products such as ether, dilute, product purity are caused to decline.The IA/AEO-4 system thereby determined that is most preferably double
Esterification temperature and best double esterification time are listed in table 1.
The best double esterification temperature of 1 IA/AEO-4 system of table and best double esterification time
2, performance test
(1) dibasic acid esters product double bond content is tested: according to petrochemical industry standard SH/T 1767-2008, " commercial aromatics
The measurement of bromine index, potentiometric titration " measurement product double bond content.
As can be seen from Table 2, the measured value with theoretical value of dibasic acid esters product double bond content are very close, illustrate the dibasic acid esters of synthesis
Product purity is higher, and the synthesis condition of optimization has feasibility.
The double bond content of 2 product of table
(2) dibasic acid esters product acid value is tested: according to standard GB/T 264-83, " petroleum product acid value measuring method " measures product
Acid value.
Acid value is the typical means of testing of dibasic acid esters, and as can be seen from Table 3, the acid value of dibasic acid esters product is very low, is not only demonstrated
The generation of dibasic acid esters product also illustrates that in the purification process of dibasic acid esters product, unreacted itaconic anhydride and monoesters largely can quilts
It removes, to improve the purity of dibasic acid esters product.
The acid value of each dibasic acid esters product of table 3
(3) dibasic acid esters surface active testing: the surface tension curve of piece method measurement product is hung according to Wilhelmy, by song
The turning point of line obtains the cmc value and γ cmc value of product, and test temperature is 25 DEG C.
As can be seen from Table 4, the size order of cmc value are as follows: dibasic acid esters product < corresponding AEO-4 illustrates to change AEO-4
After property, cmc value decreases, and surface-active is more excellent.And the surface tension γ under critical micelle concentrationcmcAfter modification without
Significant changes.
The surface-active parameter of 4 product of table
(4) dibasic acid esters product interfacial tension is tested: sample concentration 0.2%, and test temperature is 60 DEG C, revolving speed 6000r/
min。
It can be seen from the results that the effect that AEO-4 series product reduces oil water interfacial tension is good, and dibasic acid esters product reduces oil
The ability of water interfacial tension is excellent.This may be because dibasic acid esters product is actually a kind of using carbon-carbon double bond as the Shuangzi of connecting group
Surfactant arranges more closely in interface, so reduction surface-active and interfacial activity are all higher.
By upper, present invention optimizes the double esterification reaction of itaconic anhydride and AEO-4, obtained optimal reaction condition and compared with
High yield, and Lab-evaluation has been carried out to its surface-active and interfacial activity.The surface and interface superior activity of dibasic acid esters product.
For such polymerisable emulsifier, following research direction is not turn off sending structure innovation, more excellent performance of kind
With open up its application field, to and realize industrialized production.
In conclusion the present invention effectively overcomes various shortcoming in the prior art and has high industrial utilization value.
The above-described embodiments merely illustrate the principles and effects of the present invention, and is not intended to limit the present invention.It is any ripe
The personage for knowing this technology all without departing from the spirit and scope of the present invention, carries out modifications and changes to above-described embodiment.Cause
This, institute is complete without departing from the spirit and technical ideas disclosed in the present invention by those of ordinary skill in the art such as
At all equivalent modifications or change, should be covered by the claims of the present invention.
Claims (13)
1. a kind of compound, the structural formula of the compound as shown in formula II,
2. the preparation method of compound as described in claim 1, includes the following steps:
(1) using itaconic anhydride and AEO-4 as raw material, single-esterification generates type I compound, and reaction equation is as follows:
(2) type I compound and AEO-4, under the catalysis of catalyst, II compound of double esterification reaction production, reaction equation
It is as follows:
3. method according to claim 2, which is characterized in that including any one of following characteristics or multinomial: 1) step (1)
In, mono-esterification temperature >=80 DEG C of itaconic anhydride and AEO-4；Preferably, the mono-esterification temperature of itaconic anhydride and AEO-4 be 80~
100℃；It is further preferred that the mono-esterification temperature of itaconic anhydride and AEO-4 are 95 DEG C；2) monoesters of itaconic anhydride and AEO-4
Change time >=1h；Preferably, the mono-esterification time of itaconic anhydride and AEO-4 are 1~4.5h；It is further preferred that itaconic anhydride
The mono-esterification time with AEO-4 is 1h.
4. method according to claim 2, which is characterized in that in step (1), mole of AEO-4 and itaconic anhydride usage amount
Than >=2.1；Preferably, the molar ratio of AEO-4 and itaconic anhydride usage amount is 2.1~2.3；It is further preferred that AEO-4 and clothing
The molar ratio of health acid anhydrides usage amount is 2.1.
5. method according to claim 2, which is characterized in that including any one of following characteristics or multinomial: 1) step (2)
In, the catalyst is selected from p-methyl benzenesulfonic acid；2) dosage of step (2) described catalyst is 0.5% or more of total mass of raw material；
Preferably, the dosage of the catalyst is the 0.5%~2.5% of total mass of raw material；It is further preferred that the use of the catalyst
Amount is the 1.5% of total mass of raw material.
6. method according to claim 2, which is characterized in that in step (2), when reaction, it is double to remove to be additionally added water entrainer
Esterification water generated.
7. method as claimed in claim 6, which is characterized in that including any one of following characteristics or multinomial: 1) band
Aqua is selected from toluene；2) the water entrainer dosage is 1 times or more of total mass of raw material；Preferably, the water entrainer dosage is original
1~4 times for expecting gross mass；It is further preferred that the water entrainer dosage is 2 times of total mass of raw material.
8. method according to claim 2, which is characterized in that including any one of following characteristics or multinomial: 1) step (2)
In, double esterification temperature >=110 DEG C, it is preferable that, double esterification temperature is 110~150 DEG C, it is further preferred that double esterification temperature is
140℃；2) in step (2), the double esterification time >=0.5h, it is preferable that the double esterification time is 0.5~3h；It is further preferred that double
Esterification time is 1~1.5h.
9. method according to claim 2, which is characterized in that the preparation method, comprising steps of in single-esterification temperature
Under, a certain amount of itaconic anhydride is added into reaction vessel, after itaconic anhydride thawing, a certain amount of AEO-4 is added, first carries out
Single-esterification process then heats to double esterification temperature, and a certain amount of catalyst is added and carries out double esterification reaction.
10. method as claimed in claim 9, which is characterized in that after being warming up to double esterification temperature, a certain amount of catalyst is added
Double esterification reaction is carried out with water entrainer.
11. method as claimed in claim 9, which is characterized in that the dibasic acid esters product of acquisition is purified, comprising steps of
After double esterification reaction, water entrainer therein is removed, neutralizes unreacted itaconic anhydride IA and IA/AEO-4 monoesters later, then
It is dry by washing.
12. the compound prepared such as described in any item methods of claim 2~11.
13. the compound as described in claim 1 or claim 12 is used to prepare emulsifier or is used to prepare surfactant
Purposes.
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| JP2023500662A (en) * | 2019-10-29 | 2023-01-10 | ザ・ジョンズ・ホプキンス・ユニバーシティ | Novel prodrugs of itaconate and methyl itaconate |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1530386A (en) * | 2003-03-11 | 2004-09-22 | 中国石油天然气股份有限公司 | Polyethylene greenhouse film non-drop agent composition |
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| CN1530386A (en) * | 2003-03-11 | 2004-09-22 | 中国石油天然气股份有限公司 | Polyethylene greenhouse film non-drop agent composition |
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| JP2023500662A (en) * | 2019-10-29 | 2023-01-10 | ザ・ジョンズ・ホプキンス・ユニバーシティ | Novel prodrugs of itaconate and methyl itaconate |
| US12492160B2 (en) | 2019-10-29 | 2025-12-09 | The Johns Hopkins University | Prodrugs of itaconate and methyl itaconate |
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| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190416 |