CN105849080A - 直接合成生物基烷基和呋喃二元醇醚、乙酸酯、醚-乙酸酯以及碳酸酯 - Google Patents
直接合成生物基烷基和呋喃二元醇醚、乙酸酯、醚-乙酸酯以及碳酸酯 Download PDFInfo
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- CN105849080A CN105849080A CN201480071558.7A CN201480071558A CN105849080A CN 105849080 A CN105849080 A CN 105849080A CN 201480071558 A CN201480071558 A CN 201480071558A CN 105849080 A CN105849080 A CN 105849080A
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- Prior art keywords
- ether
- alcohol compounds
- diatomic alcohol
- carbonate
- glycol
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- -1 diol ethers Chemical class 0.000 title claims abstract description 64
- 125000000217 alkyl group Chemical group 0.000 title claims description 14
- 230000015572 biosynthetic process Effects 0.000 title description 17
- 238000003786 synthesis reaction Methods 0.000 title description 15
- 150000004649 carbonic acid derivatives Chemical class 0.000 title description 4
- 150000001242 acetic acid derivatives Chemical class 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 172
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 53
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 113
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 32
- 150000001298 alcohols Chemical class 0.000 claims description 29
- 150000002148 esters Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
- 238000013459 approach Methods 0.000 claims description 20
- 230000005595 deprotonation Effects 0.000 claims description 17
- 238000010537 deprotonation reaction Methods 0.000 claims description 17
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 16
- 239000003513 alkali Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000007848 Bronsted acid Substances 0.000 claims description 7
- 125000005910 alkyl carbonate group Chemical group 0.000 claims description 6
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical class CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000005690 diesters Chemical class 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- TVYABKWHFSGGMF-UHFFFAOYSA-N [2-(hydroxymethyl)oxolan-3-yl]methanol Chemical compound OCC1CCOC1CO TVYABKWHFSGGMF-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 229910052806 inorganic carbonate Inorganic materials 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract description 52
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 23
- 239000003054 catalyst Substances 0.000 abstract description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract description 11
- 230000009467 reduction Effects 0.000 abstract description 4
- 230000037361 pathway Effects 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 34
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 29
- 239000000047 product Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 15
- 230000008859 change Effects 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 238000010586 diagram Methods 0.000 description 9
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 8
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 238000003760 magnetic stirring Methods 0.000 description 7
- 239000004810 polytetrafluoroethylene Substances 0.000 description 7
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000021736 acetylation Effects 0.000 description 6
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- 150000002170 ethers Chemical class 0.000 description 6
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- 239000000376 reactant Substances 0.000 description 5
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- VEGXEWGKYMMJKP-UHFFFAOYSA-N 1-hydroxypropyl acetate Chemical compound CCC(O)OC(C)=O VEGXEWGKYMMJKP-UHFFFAOYSA-N 0.000 description 4
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 125000001118 alkylidene group Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 3
- KKQAVHGECIBFRQ-UHFFFAOYSA-N methyl propyl carbonate Chemical compound CCCOC(=O)OC KKQAVHGECIBFRQ-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 2
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- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- OKAMTPRCXVGTND-UHFFFAOYSA-N 2-methoxyoxolane Chemical compound COC1CCCO1 OKAMTPRCXVGTND-UHFFFAOYSA-N 0.000 description 2
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000013460 polyoxometalate Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/15—Unsaturated ethers containing only non-aromatic carbon-to-carbon double bonds
- C07C43/16—Vinyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/16—Acetic acid esters of dihydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361918795P | 2013-12-20 | 2013-12-20 | |
| US61/918,795 | 2013-12-20 | ||
| PCT/US2014/068809 WO2015094716A1 (en) | 2013-12-20 | 2014-12-05 | Synthesis of isohexide ethers and carbonates |
| USPCT/US2014/068809 | 2014-12-05 | ||
| US201462093683P | 2014-12-18 | 2014-12-18 | |
| US62/093,683 | 2014-12-18 | ||
| PCT/US2014/071512 WO2015095710A1 (en) | 2013-12-20 | 2014-12-19 | Direct synthesis of bio-based alkyl & furanic diol ethers, acetates, ether-acetates, and carbonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105849080A true CN105849080A (zh) | 2016-08-10 |
Family
ID=53403742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480071558.7A Pending CN105849080A (zh) | 2013-12-20 | 2014-12-19 | 直接合成生物基烷基和呋喃二元醇醚、乙酸酯、醚-乙酸酯以及碳酸酯 |
Country Status (9)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111349492A (zh) * | 2020-02-28 | 2020-06-30 | 浙江糖能科技有限公司 | 2,5-四氢呋喃二甲醇脂肪酸二酯在柴油添加剂的应用 |
| CN114072374A (zh) * | 2019-09-04 | 2022-02-18 | 伊士曼化工公司 | 芳香族烯醇醚 |
| CN114144397A (zh) * | 2019-09-04 | 2022-03-04 | 伊士曼化工公司 | 芳香族烯醇醚 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2019001840A (es) | 2016-08-16 | 2019-05-09 | Ppg Ind Ohio Inc | Composicion polimerizable para articulos opticos. |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4880942A (en) * | 1987-07-22 | 1989-11-14 | Mitsui Petrochemical Industries, Ltd. | Preparation of cyclic carbonates |
| JPH09227435A (ja) * | 1996-02-26 | 1997-09-02 | Mitsui Toatsu Chem Inc | （ポリ）エチレングリコールジエーテルの製造法 |
| CN102365286A (zh) * | 2009-10-01 | 2012-02-29 | 罗盖特公司 | 用于制备双脱水己糖醇的碳酸二烷基酯的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2963489A (en) * | 1953-07-30 | 1960-12-06 | American Cyanamid Co | 3, 4-furandimethanol and derivatives |
| US4012424A (en) * | 1975-08-07 | 1977-03-15 | Chem Systems Inc. | Cracking of mixtures containing hydroxyesters |
| US4170596A (en) * | 1976-10-05 | 1979-10-09 | Kowa Company, Ltd. | Novel monoesters of cis-cyclopentenediol, process for preparation thereof, and process for preparation of lactones from the monoesters |
| US4192949A (en) * | 1977-06-28 | 1980-03-11 | Basf Aktiengesellschaft | Preparation of aralkyl phenyl ethers and alkyl phenyl ethers |
| KR100593529B1 (ko) * | 2004-03-31 | 2006-06-28 | 주식회사 엘지생활건강 | 에스테르계 표백활성화제 화합물의 제조방법 |
| US8604244B2 (en) * | 2010-07-02 | 2013-12-10 | Reviva Pharmaceuticals, Inc. | Compositions, synthesis, and methods of using cycloalkylmethylamine derivatives |
-
2014
- 2014-12-19 CA CA2934512A patent/CA2934512A1/en not_active Abandoned
- 2014-12-19 EP EP14871997.4A patent/EP3083548A4/en not_active Withdrawn
- 2014-12-19 JP JP2016538518A patent/JP2017507899A/ja not_active Withdrawn
- 2014-12-19 AU AU2014369062A patent/AU2014369062A1/en not_active Abandoned
- 2014-12-19 MX MX2016008061A patent/MX2016008061A/es unknown
- 2014-12-19 CN CN201480071558.7A patent/CN105849080A/zh active Pending
- 2014-12-19 WO PCT/US2014/071512 patent/WO2015095710A1/en active Application Filing
- 2014-12-19 BR BR112016014267A patent/BR112016014267A2/pt not_active IP Right Cessation
- 2014-12-19 KR KR1020167018951A patent/KR20160099646A/ko not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4880942A (en) * | 1987-07-22 | 1989-11-14 | Mitsui Petrochemical Industries, Ltd. | Preparation of cyclic carbonates |
| JPH09227435A (ja) * | 1996-02-26 | 1997-09-02 | Mitsui Toatsu Chem Inc | （ポリ）エチレングリコールジエーテルの製造法 |
| CN102365286A (zh) * | 2009-10-01 | 2012-02-29 | 罗盖特公司 | 用于制备双脱水己糖醇的碳酸二烷基酯的方法 |
Non-Patent Citations (3)
| Title |
|---|
| PIETRO TUNDO, ET AL.,: "Green Synthesis of Dimethyl Isosorbide", 《CHEMSUSCHEM》 * |
| 刘小成等: "2-醋酸异山梨醇酯的合成研究", 《化学与生物工程》 * |
| 朱驯: "乙二醇单乙醚醋酸酯的合成工艺改进研究", 《应用化工》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114072374A (zh) * | 2019-09-04 | 2022-02-18 | 伊士曼化工公司 | 芳香族烯醇醚 |
| CN114144397A (zh) * | 2019-09-04 | 2022-03-04 | 伊士曼化工公司 | 芳香族烯醇醚 |
| CN114072374B (zh) * | 2019-09-04 | 2024-03-08 | 伊士曼化工公司 | 芳香族烯醇醚 |
| CN111349492A (zh) * | 2020-02-28 | 2020-06-30 | 浙江糖能科技有限公司 | 2,5-四氢呋喃二甲醇脂肪酸二酯在柴油添加剂的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20160099646A (ko) | 2016-08-22 |
| MX2016008061A (es) | 2017-02-27 |
| WO2015095710A1 (en) | 2015-06-25 |
| JP2017507899A (ja) | 2017-03-23 |
| BR112016014267A2 (pt) | 2017-08-08 |
| EP3083548A4 (en) | 2017-08-30 |
| AU2014369062A1 (en) | 2016-06-30 |
| CA2934512A1 (en) | 2015-06-25 |
| EP3083548A1 (en) | 2016-10-26 |
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