BR112016014052B1 - Método para preparação de um éster de isohexídeo e método de fabricação de um poliéster - Google Patents
Método para preparação de um éster de isohexídeo e método de fabricação de um poliéster Download PDFInfo
- Publication number
- BR112016014052B1 BR112016014052B1 BR112016014052-4A BR112016014052A BR112016014052B1 BR 112016014052 B1 BR112016014052 B1 BR 112016014052B1 BR 112016014052 A BR112016014052 A BR 112016014052A BR 112016014052 B1 BR112016014052 B1 BR 112016014052B1
- Authority
- BR
- Brazil
- Prior art keywords
- acid
- isohexide
- color
- reducing
- isosorbide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 229920000728 polyester Polymers 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 150000002148 esters Chemical class 0.000 claims abstract description 26
- 239000007848 Bronsted acid Substances 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 42
- 241001550224 Apha Species 0.000 claims description 39
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 39
- 229960002479 isosorbide Drugs 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 20
- 239000003377 acid catalyst Substances 0.000 claims description 15
- KLDXJTOLSGUMSJ-UNTFVMJOSA-N (3s,3ar,6s,6ar)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-UNTFVMJOSA-N 0.000 claims description 12
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 11
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 11
- 150000007524 organic acids Chemical class 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 8
- 239000002243 precursor Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 abstract description 15
- 230000032050 esterification Effects 0.000 abstract description 14
- 238000011065 in-situ storage Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 34
- 239000000463 material Substances 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 150000005690 diesters Chemical class 0.000 description 7
- -1 sugars are complex Chemical class 0.000 description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 6
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 6
- FBPFZTCFMRRESA-UNTFVMJOSA-N L-iditol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO FBPFZTCFMRRESA-UNTFVMJOSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 229960002920 sorbitol Drugs 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
- 238000007309 Fischer-Speier esterification reaction Methods 0.000 description 4
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000002028 Biomass Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000116 mitigating effect Effects 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000011143 downstream manufacturing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000006345 epimerization reaction Methods 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 238000006864 oxidative decomposition reaction Methods 0.000 description 2
- 239000003348 petrochemical agent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000002000 scavenging effect Effects 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000005846 sugar alcohols Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- WQZGKKKJIJFFOK-ZNVMLXAYSA-N L-idopyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-ZNVMLXAYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 238000005844 autocatalytic reaction Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical class Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0257—Phosphorus acids or phosphorus acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361917390P | 2013-12-18 | 2013-12-18 | |
| US61/917,390 | 2013-12-18 | ||
| US201361918810P | 2013-12-20 | 2013-12-20 | |
| US61/918,810 | 2013-12-20 | ||
| PCT/US2014/066301 WO2015094548A1 (en) | 2013-12-18 | 2014-11-19 | Control of color-body formation in isohexide esterification |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112016014052A2 BR112016014052A2 (pt) | 2017-08-08 |
| BR112016014052B1 true BR112016014052B1 (pt) | 2021-07-27 |
Family
ID=53403490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112016014052-4A BR112016014052B1 (pt) | 2013-12-18 | 2014-11-19 | Método para preparação de um éster de isohexídeo e método de fabricação de um poliéster |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9828387B2 (enExample) |
| EP (1) | EP3083635B1 (enExample) |
| JP (1) | JP2017502932A (enExample) |
| KR (1) | KR102082545B1 (enExample) |
| CN (1) | CN105814063B (enExample) |
| AU (1) | AU2014367102B2 (enExample) |
| BR (1) | BR112016014052B1 (enExample) |
| CA (1) | CA2932265C (enExample) |
| HK (1) | HK1235051A1 (enExample) |
| MX (1) | MX378510B (enExample) |
| WO (1) | WO2015094548A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014366354A1 (en) * | 2013-12-19 | 2016-06-16 | Archer Daniels Midland Company | An improved glycol acylation process |
| CN108658998B (zh) * | 2018-04-28 | 2019-12-03 | 山东岩海建设资源有限公司 | 一种异山梨醇酯增塑剂及其制备方法和应用 |
| CN112619635B (zh) * | 2019-09-24 | 2023-04-11 | 中国石油化工股份有限公司 | 一种双金属氧化物催化剂及其制备方法和应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS442964Y1 (enExample) * | 1965-07-20 | 1969-02-04 | ||
| US4610825A (en) * | 1985-04-17 | 1986-09-09 | Stepan Company | Phosphorous acid catalyzed phenol esterification |
| US4690783A (en) * | 1986-08-29 | 1987-09-01 | Union Camp Corporation | Method of preparing rosin ester from polyol with phosphorous acid catalyst |
| US5210155A (en) * | 1990-08-24 | 1993-05-11 | Exxon Chemical Patents Inc. | Phenol terminated diester compositions derived from dicarboxylic acids, polyester polymers or alkyd polymers, and curable compositions containing same |
| FR2883877B1 (fr) * | 2005-04-01 | 2008-10-10 | Roquette Freres | Procede de preparation de compositions de diester(s) de dianhydrohexitol |
| JP5379016B2 (ja) * | 2007-10-31 | 2013-12-25 | 帝人株式会社 | 保存安定性が良好な無水糖アルコール組成物およびそれを用いるポリカーボネートの製造方法 |
| EP2239315A1 (en) * | 2009-04-09 | 2010-10-13 | Cognis IP Management GmbH | Isosorbide monoesters and their use in household applications |
| US9580544B2 (en) * | 2010-03-18 | 2017-02-28 | New Jersey Institute Of Technology | Polyesters from asymetrical monomers based upon bisanhydrohexitols |
| DE102011077857A1 (de) * | 2011-06-21 | 2012-12-27 | Evonik Oxeno Gmbh | Dianhydrohexitoldiester der 2-Ethylheptansäure |
| FR2990210B1 (fr) * | 2012-05-03 | 2014-05-02 | Roquette Freres | Compositions plastifiantes comprenant des accelerateurs de gelification a base d'ester de 1,4 : 3,6-dianhydrohexitol de faible poids molaire |
-
2014
- 2014-11-19 KR KR1020167019139A patent/KR102082545B1/ko active Active
- 2014-11-19 EP EP14871641.8A patent/EP3083635B1/en active Active
- 2014-11-19 WO PCT/US2014/066301 patent/WO2015094548A1/en not_active Ceased
- 2014-11-19 CN CN201480068484.1A patent/CN105814063B/zh active Active
- 2014-11-19 AU AU2014367102A patent/AU2014367102B2/en active Active
- 2014-11-19 US US15/102,281 patent/US9828387B2/en active Active
- 2014-11-19 HK HK16114625.6A patent/HK1235051A1/zh unknown
- 2014-11-19 MX MX2016007864A patent/MX378510B/es unknown
- 2014-11-19 JP JP2016535204A patent/JP2017502932A/ja active Pending
- 2014-11-19 BR BR112016014052-4A patent/BR112016014052B1/pt active IP Right Grant
- 2014-11-19 CA CA2932265A patent/CA2932265C/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| BR112016014052A2 (pt) | 2017-08-08 |
| CA2932265A1 (en) | 2015-06-25 |
| EP3083635A1 (en) | 2016-10-26 |
| AU2014367102B2 (en) | 2018-09-20 |
| JP2017502932A (ja) | 2017-01-26 |
| HK1235051A1 (zh) | 2018-03-02 |
| EP3083635A4 (en) | 2017-04-26 |
| MX378510B (es) | 2025-03-11 |
| US20170022214A1 (en) | 2017-01-26 |
| EP3083635B1 (en) | 2019-10-02 |
| CN105814063B (zh) | 2018-09-18 |
| US9828387B2 (en) | 2017-11-28 |
| CN105814063A (zh) | 2016-07-27 |
| KR20160098453A (ko) | 2016-08-18 |
| AU2014367102A1 (en) | 2016-06-16 |
| CA2932265C (en) | 2020-12-01 |
| MX2016007864A (es) | 2016-09-07 |
| KR102082545B1 (ko) | 2020-02-27 |
| WO2015094548A1 (en) | 2015-06-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Rose et al. | Isosorbide as a renewable platform chemical for versatile applications—quo vadis? | |
| JP2016501893A (ja) | ハイドロールを用いた無水糖アルコールの製造方法 | |
| KR102107274B1 (ko) | 산 촉매의 혼합 조합을 이용한 당 알코올의 탈수 | |
| KR20130126303A (ko) | 박막증류를 통한 고순도 무수당 알코올의 제조방법 | |
| BR112016014052B1 (pt) | Método para preparação de um éster de isohexídeo e método de fabricação de um poliéster | |
| JP4370280B2 (ja) | 無水糖アルコール組成物の精製方法および製造方法 | |
| US10081611B2 (en) | Method for acid-catalyzed acylation of the reduction products of 5-hydroxymethyl furfural | |
| CN103649095A (zh) | 制备脱水糖醇的方法 | |
| JP2017501147A (ja) | イソヘキシドエーテルおよびイソヘキシドカーボネートの合成 | |
| CN106061979B (zh) | 乙二醇酰化的增强的区域选择性 | |
| JP2009286741A (ja) | ヒドロキシカルボン酸化合物とその製造方法およびポリエステル樹脂 | |
| JP2017501138A (ja) | 改善されたグリコールのアシル化プロセス | |
| BR112016014032B1 (pt) | Método para acilação catalisada por ácido de um isossorbida | |
| KR102025601B1 (ko) | 암모늄 치환 헤테로 폴리산염 촉매를 이용한 무수당 알코올의 제조방법 | |
| WO2016099788A1 (en) | Preparation of isohexide trifluoroacetates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06U | Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette] | ||
| B07D | Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette] |
Free format text: DE ACORDO COM O ARTIGO 229-C DA LEI NO 10196/2001, QUE MODIFICOU A LEI NO 9279/96, A CONCESSAO DA PATENTE ESTA CONDICIONADA A ANUENCIA PREVIA DA ANVISA. CONSIDERANDO A APROVACAO DOS TERMOS DO PARECER NO 337/PGF/EA/2010, BEM COMO A PORTARIA INTERMINISTERIAL NO 1065 DE 24/05/2012, ENCAMINHA-SE O PRESENTE PEDIDO PARA AS PROVIDENCIAS CABIVEIS. |
|
| B07G | Grant request does not fulfill article 229-c lpi (prior consent of anvisa) [chapter 7.7 patent gazette] | ||
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B09W | Correction of the decision to grant [chapter 9.1.4 patent gazette] |
Free format text: REFERENCIA: RPI 2631 DE 08.06.2021 - CODIGO 9.1 |
|
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 19/11/2014, OBSERVADAS AS CONDICOES LEGAIS. |