WO2022111849A1 - Produit de deshydratation interne du sorbitol de haute purete - Google Patents
Produit de deshydratation interne du sorbitol de haute purete Download PDFInfo
- Publication number
- WO2022111849A1 WO2022111849A1 PCT/EP2021/025454 EP2021025454W WO2022111849A1 WO 2022111849 A1 WO2022111849 A1 WO 2022111849A1 EP 2021025454 W EP2021025454 W EP 2021025454W WO 2022111849 A1 WO2022111849 A1 WO 2022111849A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ppm
- product
- dry weight
- solution
- sorbitol
- Prior art date
Links
- 238000006297 dehydration reaction Methods 0.000 title claims abstract description 47
- 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 title claims abstract description 44
- 239000000600 sorbitol Substances 0.000 title claims abstract description 44
- 230000018044 dehydration Effects 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 39
- 229920000642 polymer Polymers 0.000 claims abstract description 37
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims description 79
- 229920005989 resin Polymers 0.000 claims description 26
- 239000011347 resin Substances 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 238000004821 distillation Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 150000007514 bases Chemical class 0.000 claims description 16
- 229920000728 polyester Polymers 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 238000005342 ion exchange Methods 0.000 claims description 11
- 229920000515 polycarbonate Polymers 0.000 claims description 11
- 239000004417 polycarbonate Substances 0.000 claims description 11
- 125000002091 cationic group Chemical group 0.000 claims description 10
- 238000004042 decolorization Methods 0.000 claims description 9
- 125000000129 anionic group Chemical group 0.000 claims description 8
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 5
- 239000000920 calcium hydroxide Substances 0.000 claims description 5
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 239000012264 purified product Substances 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 229920000090 poly(aryl ether) Polymers 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 claims description 2
- 229910001866 strontium hydroxide Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 229960002479 isosorbide Drugs 0.000 description 80
- 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 description 79
- 239000000243 solution Substances 0.000 description 73
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000003756 stirring Methods 0.000 description 15
- 230000002829 reductive effect Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 239000012429 reaction media Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920002492 poly(sulfone) Polymers 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000005846 sugar alcohols Chemical class 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- -1 aliphatic alcohols Chemical class 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- 241001550224 Apha Species 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 240000003183 Manihot esculenta Species 0.000 description 2
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000004172 nitrogen cycle Methods 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- UWLINSANVPZJBA-UHFFFAOYSA-N 2-(chloromethyl)oxirane hydrate Chemical compound O.ClCC1CO1 UWLINSANVPZJBA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 101150099000 EXPA1 gene Proteins 0.000 description 1
- 102100029095 Exportin-1 Human genes 0.000 description 1
- 244000261422 Lysimachia clethroides Species 0.000 description 1
- 101100119348 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) EXP1 gene Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 101100269618 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) aliA gene Proteins 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- BEIOEBMXPVYLRY-UHFFFAOYSA-N [4-[4-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C BEIOEBMXPVYLRY-UHFFFAOYSA-N 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000001636 atomic emission spectroscopy Methods 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 150000004650 carbonic acid diesters Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 108700002148 exportin 1 Proteins 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940119177 germanium dioxide Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
- C08G65/4056—(I) or (II) containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
- C08G75/23—Polyethersulfones
Definitions
- the present invention relates to a product of internal dehydration of high purity sorbitol, a process for the manufacture of such a product and a polymer comprising said product as monomer. More particularly, the present invention relates to a high purity isosorbide, a process for the manufacture of such an isosorbide and a polymer comprising isosorbide as a monomer.
- Isosorbide 1,4:3,6-dianhydrosorbitol, an internal dehydration product of sorbitol, is of major interest as a recoverable natural resource in the manufacture of polymers.
- Isosorbide is indeed a derivative of sorbitol which can be obtained from various natural resources, including, corn starch and cassava (tapioca).
- the purity requirements depend on the intended application. In food and therapeutic applications, for example, it is essential that the compounds containing them contain no impurities which could be harmful to the individual or to the organization which uses them.
- a requirement in terms of monomer purity is that no material or impurities should be present in the monomer which could result in a unacceptable degree of coloration of the polymer during its synthesis and/or its transformation.
- the isosorbide can develop a coloration resulting from the presence of impurities in it. Thus, the coloring of the final product is no longer controlled. Such coloring is therefore not desired.
- the document WO 2008143269 describes a process for obtaining a polycarbonate based on isosorbide and a carbonic acid diester in which the synthesis of said polymer is followed by a distillation step so as to eliminate the phenol formed. .
- the polycarbonate thus obtained has a residual level of Na, Fe and Ca of less than 2 ppm.
- the document KR101736182 describes a method for purifying such an alcohol comprising passage over a cation exchange resin, the pH of the solution comprising said alcohol to be purified being adjusted to at least 5, for example between 5 and 8, at ambient temperature.
- the document KR101736180 describes a method for purifying an anhydrous sugar alcohol in which the level of formic acid is less than 1 ppm. This method involves passage over a strong basic anion exchange resin.
- the document EP1882712 relates to a polyester obtained from a diol and a carboxylic acid in which both the level of impurities and the number of terminal acid groups are reduced so as to reduce the hydrolysis and therefore to improve the stability of the polyester over time.
- the rate of sulfur atoms in the monomers is between 0.01 ppm and 100 ppm
- the rate of nitrogen atoms in the monomers is between 0.01 ppm and 2000 ppm
- the number of terminal acid groups in the polyester is less than 50 equivalents/metric ton.
- Document FR2810040 relates to a method for purifying a composition in which the composition to be purified is successively subjected to ion exchange and discoloration.
- the invention relates to an internal dehydration product of sorbitol characterized in that it has a total residual rate of nitrogen atoms of between 0.01 ppm and 150 ppm, preferably between 0.02 ppm and 20 ppm, more preferably between 0.05 ppm and 10 ppm, and more preferably between 0.07 ppm and 5 ppm, this residual rate being expressed in dry weight relative to the total dry weight of said product and in that it has a total residual sulfur atom content of between 0.0001 ppm and 100 ppm, preferably between 0.0002 ppm and 50 ppm, more preferably between 0.0004 ppm and 30 ppm and, more preferably, between 0.0008 ppm and 20 ppm, this total residual rate being expressed in dry weight relative to the dry weight of said product.
- the invention relates to a method for purifying a product of internal dehydration of sorbitol according to the first object, said method comprising a succession of steps a) a step of supplying said product of internal dehydration of sorbitol, b) a step of distilling said dehydration product so as to form a distillation product A, c) a step of redissolving said distillation product A in water with addition of a basic compound so as to form a solution B, d) at least one step of decolorizing solution B from the step of redissolving with addition of a basic compound, e) at least one step of ion exchange of the solution from the decolorization step and, f) a step for recovering the resulting purified product C, said basic compound being added in an amount of between 1 and 6 g, preferably between 2 and 5 g per Kg of sorbitol internal dehydration product supplied in step a).
- the invention relates to a polymer chosen from a polyester, a polycarbonate, a polyarylether, a polyurethane or a polyepoxide, said polymer is characterized in that it comprises a pattern corresponding to the product of internal dehydration sorbitol according to the first object or obtained from a process according to the second object.
- the internal dehydration products of sorbitol according to the invention have an excellent level of purity, particularly products having both a very low level of sulfur and nitrogen atoms.
- the process according to the invention therefore makes it possible to obtain such internal dehydration products of sorbitol having excellent purity while using conventional purification techniques.
- the polymers obtained based on internal dehydration products of sorbitol according to the invention have remarkable optical properties in terms of coloring and clarity, without affecting the other characteristics. essential in the field of plastic objects, such as viscosity and thermal resistance
- a first object of the invention relates to an internal dehydration product of sorbitol having a total residual level of nitrogen atoms of between 0.01 ppm and 150 ppm, preferably between 0.02 ppm and 20 ppm, more preferably between 0.05 ppm and 10 ppm, and, more preferably, between 0.07 ppm and 5 ppm, this residual rate being expressed in dry weight relative to the total dry weight of said product and having a total residual sulfur atom rate of between 0.0001 ppm and 100 ppm, preferably between 0.0002 ppm and 50 ppm, more preferably between 0.0004 ppm and 30 ppm and, more preferably, between 0.0008 ppm and 20 ppm, this total residual rate being expressed in dry weight relative to the dry weight of said product.
- inter dehydration product of sorbitol means any product or composition resulting, in any way whatsoever, in one or more stages, from the removal of one or more water molecules at the level of the original internal structure of sorbitol.
- the internal dehydration product of sorbitol has a total residual level of sodium and potassium atoms of between 0.002 ppm and 100 ppm, preferably between 0.004 ppm and 50 ppm, more preferably comprised between 0.006 ppm and 20 ppm, and, more preferentially, comprised between 0.008 ppm and 10 ppm, this total residual rate being expressed in dry weight relative to the total dry weight of said product.
- the internal dehydration product of sorbitol has a total residual level of calcium and magnesium atoms of between 0.005 ppm and 100 ppm, preferably between 0.010 ppm and 50 ppm, of more preferably comprised between 0.015 ppm and 20 ppm, and, more preferably, comprised between 0.020 ppm and 10 ppm, this total residual rate being expressed in dry weight relative to the total dry weight of said product.
- the internal dehydration product of sorbitol has a total residual level of iron atoms of between 0.005 ppm and 100 ppm, preferably between 0.010 ppm and 50, more preferably between 0.015 ppm and 20 ppm, and more preferably between 0.020 ppm and 10 ppm, this total residual level being expressed in dry weight relative to the total dry weight of said product.
- the internal dehydration product of sorbitol has a total residual level of chlorine atoms of between 0.005 ppm and 100 ppm, preferably between 0.010 ppm and 50, more preferably between 0.015 ppm and 20 ppm, and more preferably between 0.020 ppm and 10 ppm, this total residual level being expressed in dry weight relative to the total dry weight of said product.
- the internal dehydration products of sorbitol according to the invention correspond to products or compositions as defined above, the dehydration possibly being total or partial.
- these internal dehydration products of sorbitol can be used advantageously in many industries and in particular as a synthesis intermediate, comonomer (including chain extender), solvent agent, plasticizer, lubricating agent , bulking agent, sweetener and/or active principle, in the preparation of products or mixtures, polymeric or not, biodegradable or not, intended for the chemical, pharmaceutical, cosmetic or food industries.
- a second object of the invention relates to a method for purifying an internal dehydration product of sorbitol according to the first object, said method comprising a succession of steps a) a step of supplying said internal dehydration product of sorbitol, b) a step of distilling said dehydration product so as to form a distillation product A, c) a step of redissolving said distillation product in water A with addition of a basic compound so as to form a solution B, d) at least one step of decolorizing the solution B resulting from the step of redissolving with addition of a basic compound, e) at least one step of ion exchange of the solution resulting from the decolorization step and, f) a step of recovering the resulting purified product C, said basic compound being added in an amount of between 1 and 6 g, preferably between 2 and 5 g per kg of sorbitol internal dehydration product provided in step a).
- the distillation step is done in a continuous evaporator.
- a continuous evaporator for example of the falling film type or better, of the scraped film or short path type, makes it possible to limit the temperatures and residence times to which the reaction crudes are thus subjected.
- the intermediate pH of the distillation product A can be measured.
- the distillation product A is redissolved in water so as to obtain an aqueous solution comprising between 50 and 90% dry matter, preferably between 60 and 80% dry matter.
- a basic compound is added with stirring at 150 rotations per minute (RPM) and at ambient temperature (20° C.).
- RPM rotations per minute
- the medium thus obtained can be kept under stirring for a period of between 30 minutes and two hours, preferably between 45 minutes and 75 minutes.
- the medium thus obtained can be subjected to a filtration step.
- the filtrate can then be diluted in water so as to obtain an aqueous solution comprising between 30 and 70% dry matter, preferably between 40 and 60% dry matter.
- the pH of solution B can be measured. According to one embodiment, the pH of solution B is between 4 and 10, preferably between 7 and 9.
- the basic compound is chosen from alkaline-earth hydroxides such as magnesium hydroxide, calcium hydroxide, strontium hydroxide or barium hydroxide, preferably calcium hydroxide.
- the treatment by the decolorization step comprises at least one passage through a column of granular activated carbon.
- At least one ion exchange step is chosen from a passage over a cationic resin or a passage over an anionic resin or a mixture of two, preferably the cationic resin is a strong cationic resin and the anion resin is a strong anion resin.
- the process comprises at least two ion exchange steps, these will follow one another so that the solution is recovered and successively passed over a column of cationic resin then a column of anionic resin.
- the process comprises at least two ion exchange steps, these will follow one another so that the solution is recovered and successively passed over a column of strong cationic resin then a column of strong anionic resin.
- the internal dehydration product of sorbitol used according to the purification process above corresponds to a single product or to a composition comprising a mixture of entities resulting from the internal dehydration reaction of sorbitol.
- the method is free of an additional decolorization step after the ion exchange step and before the step for recovering the resulting product.
- the method is free of an additional step of recrystallization of the various intermediate products of said method.
- the method for purifying a sorbitol internal dehydration product according to the first object consisting of a succession of steps: a) a step for supplying said sorbitol internal dehydration product , b) a step of distilling said dehydration product so as to form a distillation product A, c) a step of redissolving said distillation product A in water with the addition of a basic compound so as to form a solution B, d) at least one step of decolorizing solution B from the step of redissolving with addition of a basic compound, e) at least one step of ion exchange of the solution from step decolorization and, f) a step of recovering the resulting purified product C, said basic compound being added in an amount of between 1 and 6 g, preferably between 2 and 5 g per Kg of sorbito
- a third object of the invention relates to a polymer chosen from a polyester, a polycarbonate, a polyarylether, a polyurethane or a polyepoxide, said polymer is characterized in that it comprises a unit corresponding to the internal dehydration product of sorbitol according to the first object or obtained from a process according to the second object.
- reaction crude is then cooled to 100° C. then neutralized with 13.7 g of a 50% sodium hydroxide solution.
- the isosorbide composition obtained is then distilled under vacuum using a scraped film evaporator in short path configuration.
- the pH of the distilled isosorbide (in solution at 40% dry matter) is then 3.5.
- the distillate is recovered and then put back into solution in water in order to obtain a solution with 70% dry matter.
- 2.5 g of calcium hydroxide are added under vigorous stirring and at temperature. The medium is left stirring for 1 hour.
- the medium is then cloudy and opaque.
- the medium is then filtered through a Becko filter (0.45 ⁇ m) to obtain a clear solution. Water is then added to obtain a 50% DM solution. The pH of the final solution is 8.5.
- This solution is then percolated over a column packed with granular activated carbon at a rate of 0.5VV:H (volume of solution per volume of fixed bed and per hour).
- the solution is then recovered and passed successively over a column of strong cationic resin then a column of strong anionic resin.
- the solution is then concentrated under vacuum to obtain, after crystallization and grinding of the solid, a white powder.
- the isosorbide composition obtained is then distilled under vacuum using a scraped film evaporator in short path configuration.
- the distilled isosorbide is redissolved in distilled water to form a 50% dry matter solution.
- the pH of this solution is 3.5
- the solution is then recovered and passed successively over a column of strong cationic resin then a column of strong anionic resin.
- the solution is then concentrated under vacuum to obtain, after crystallization and grinding of the solid, a white powder.
- reaction crude is then cooled to 100° C. then neutralized with 13.7 g of a 50% sodium hydroxide solution.
- the isosorbide composition obtained is then distilled under vacuum using a scraped film evaporator in the short path configuration.
- the distillate is recovered and then redissolved in water in order to obtain a solution with 70% dry matter.
- 3 g of magnesium carbonate are added to this solution with vigorous stirring and at ambient temperature.
- the medium is left stirring for 1 hour.
- the solution being slightly cloudy, the medium is filtered through a Becko filter (0.45 ⁇ m) [0070] Water is then added in order to obtain a 50% dry matter solution.
- the pH of the final solution is 9.5.
- the distilled isosorbide is redissolved in distilled water to form a 50% dry matter solution. This solution is then percolated over a column packed with granular activated carbon at a rate of 0.5VV:H followed by treatment with black powder at the level of 2% by mass of black relative to the dry matter. The solution is then filtered to recover the isosorbide solution.
- the solution is then concentrated under vacuum to obtain, after crystallization and grinding of the solid, a white powder.
- reaction crude is then cooled to 100° C. then neutralized with 13.7 g of a 50% sodium hydroxide solution.
- the isosorbide composition obtained is then distilled under vacuum using a scraped film evaporator in the short path configuration.
- the distillate is recovered and then put back into solution in water in order to obtain a solution with 70% dry matter.
- 9 g of a solution of tetraethylammonium hydroxide (aqueous solution at 35% dry matter) are added with stirring and at room temperature. The medium is left stirring for 1 hour. The solution is clear after this treatment.
- the distilled isosorbide is redissolved in distilled water to form a 50% dry matter solution.
- This solution is then percolated over a column packed with granular activated carbon at a rate of 0.5VV:H followed by treatment with black powder at the height of 2% by mass of black relative to the dry matter.
- the solution is then filtered to recover the isosorbide solution.
- the solution is then concentrated under vacuum to obtain, after crystallization and grinding of the solid, a white powder.
- the isosorbides produced are denoted 11, I2 and I3 respectively.
- the amounts of nitrogen, sulfur, sodium and potassium, magnesium, iron, chlorine and calcium are given in Table 1. These elements are determined by atomic emission spectroscopy by induced plasma coupling (Inductively coupled plasma-atomic emission spectroscopy ICP AES).
- Example 5 PEI30T Polyesters Based on Isosorbide 11 According to Example 1
- the reaction mixture is then heated to 250° C. (4° C./min) under 2.5 bars of pressure and with constant stirring (150 rpm).
- the esterification rate is estimated from the amount of distillate collected.
- the pressure is reduced to 0.7 mbar in 90 minutes according to a logarithmic ramp and the temperature brought to 265°C.
- a polymer rod is poured through the bottom valve of the reactor, cooled in a temperature-controlled water tank at 15° C. and cut into the form of granules of approximately 15 mg.
- the resin thus obtained has a reduced solution viscosity of 60.5 mL/g.
- the 1 H NMR analysis of polyester P1 shows that it contains 30.4 mol% of isosorbide relative to the diols.
- the level of diethylene glycol unit is 2.3 mol%.
- the polymer is amorphous and has a Tg of 112.4°C.
- Example 6 Example Polyester PEI30T based on isosorbide I2 according to example 2
- the resin obtained has a reduced solution viscosity of 61.2 mL/g.
- polyester P2 contains 29.9 mol% of isosorbide relative to the diols.
- the level of diethylene glycol unit is 2.5 mol%.
- the polymer is amorphous and has a Tg of 112.1°C.
- the haze measured on injected plates 2 mm thick is 5.1.
- Example 7 Example Polyester PEI30T based on isosorbide I3 according to example 3
- Example 5 The protocol of Example 5 is reproduced with the isosorbide of I3.
- the resin obtained has a reduced solution viscosity of 60.8 mL/g.
- the 1H NMR analysis of the polyester P3 shows that it contains 30.5% mol of isosorbide relative to the diols.
- the level of diethylene glycol unit is 2.3 mol%.
- the polymer is amorphous and has a Tg of 113.0°C.
- Comparative Example 8 Example Polyester PEI30T Based on I4 Isosorbide According to Example 4 [0113] The protocol of Example EXP1 is reproduced with the I4 isosorbide.
- the resin obtained has a reduced solution viscosity of 61.8 mL/g.
- the 1H NMR analysis of the polyester P3 shows that it contains 30.1% mol of isosorbide relative to the diols.
- the level of diethylene glycol unit is 2.3 mol%.
- the polymer is amorphous and has a Tg of 111.3°C.
- Example 9 Example Polycarbonate based on isosorbide 11 according to example 1
- the distillation column is heated to 110° C. to prevent crystallization of the phenol which is released during the reaction.
- the stirring speed is adjusted to 120 rpm (this will be reduced as the viscosity increases).
- the reactor is then heated and a vacuum ramp is applied while increasing the temperature of the reaction medium.
- the temperature and pressure conditions used are as follows:
- the resin thus obtained has a reduced solution viscosity of 52.5 mL/g.
- the 1 H NMR analysis of the P4 polycarbonate shows that it contains 74.2 mol% of isosorbide relative to the diols.
- the polymer is amorphous and has a Tg of 130.4°C.
- Example 10 Example Polycarbonate based on isosorbide I3 according to example 3
- Example 9 The protocol of Example 9 is reproduced, this time with the isosorbide of I3.
- the resin thus obtained has a reduced solution viscosity of 49.4 mL/g.
- the 1 H NMR analysis of the P5 polycarbonate shows that it contains 70.1% mol of isosorbide relative to the diols.
- the polymer is amorphous and has a Tg of 126.0°C.
- the haze measured on 2 mm thick injected plates is 4.1.
- Example Polysulfone based on isosorbide 11 according to Example 1
- the polysulfone P6 thus obtained has a reduced solution viscosity of 36.1 mL/g.
- the polymer is amorphous and has a Tg of 236.5°C.
- the polymer was then put in the form of a film by solvent evaporation method from a 20w% polymer solution in DMSO.
- the viscous polymer solution was applied with a metal blade to a glass substrate.
- the deposit is then slowly evaporated in an oven according to the following protocol: 50° C. for 16 h, 80° C. for 1 h, 130° C. for 1 h, 130° C. for 1 h and 180° C. for 2 h.
- a film with a thickness of about 100 microns is obtained.
- the film is colorless and has a haze of 0.2.
- Example 12 Example Polysulfone based on isosorbide I2 according to example 2
- the polysulfone P7 thus obtained has a reduced solution viscosity of 35.8 mL/g.
- the polymer is amorphous and has a Tg of 236.2°C.
- a 100 micron film made using the same procedure as in example 11 is slightly yellow and has a haze of 1.1. From the results obtained in Examples 11 and 12, the haze values of the isosorbide-based polysulphones according to the invention (11) are the lowest. The polysulphones based on isosorbide according to the invention therefore have a more satisfactory clarity. The results of Examples 11 and 12 are shown in Table 4.
- Example 13 Example isosorbide D1 diester based on isosorbide 11 according to Example 1 C8) followed by 1.4 kg of isosorbide 11 (fatty acid/isosorbide molar ratio: 2.2). Then 30g of methanesulfonic acid and 8.4g of hypophosphorous acid are added.
- the reactor is heated to a set temperature of 160° C. and a vacuum of 100 mbars is applied to the system. Once the medium is at 90°C and the first drops of water have been distilled, a vacuum ramp of 1000 to 30 mbar is carried out over 5 hours. Once the ramp is complete, the reactor temperature set point is brought to 170° C. for a period of 2 hours at 30 mbar.
- the heating is switched off and the medium is brought back to a temperature of 115° C. Then add 15mL of a 50% sodium hydroxide solution to neutralize the catalysts. The reaction medium is left to cool to room temperature.
- the excess fatty acid used is distilled on a wiped-film evaporator.
- the diester is recovered at the bottom of the tank while the excess acid is distilled off.
- the measurement of the coloration according to the APHA scale is carried out on a Lovibond PFX-i Sériés spectrophotometer according to the ASTM D-1209 method (January 2005), with a rectangular tank of 5 cm in APHA color scale by a colorimeter adapted to the product without dissolving in any solvent. The results are presented in Table 5.
- Example 14 Example diester of isosorbide D2 based on isosorbide I2 according to example 2
- Example 15 Example Diglycidylether of isosorbide D3 based on isosorbide 11 according to example 1
- the medium is left to heat and distill until a medium temperature of 90°C is obtained. When this temperature is reached, the heating is switched off and the medium is left to cool to ambient temperature. The medium is then decanted and the salts formed during the reaction are filtered using a glass frit of porosity 3. The salt cake is then washed using 150 g of epichlorohydrin. The filtrate is recovered. The residual epichlorohydrin is removed by vacuum distillation using a rotary evaporator.
- Example 16 Example Diglycidylether of isosorbide D4 based on isosorbide I2 according to example 2
- Example 17 Example of coating with diglycidylether of isosorbide D3 based on isosorbide I3 according to example 3
- the final coating with a thickness of 151 microns has a Persoz hardness of 297s, a pencil hardness of 16N, a gloss at 20° of 96.7. During the adhesion test with the cross cutter, no element came off the substrate.
- Example 18 Example of coating with diglycidylether of isosorbide D4 based on isosorbide I4 according to example 4
- the final coating with a thickness of 145 microns has a Persoz hardness of 295s, a pencil hardness of 16N, a gloss at 20° of 91.1. During the adhesion test with the cross cutter, no element came off the substrate.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polyesters Or Polycarbonates (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP21814683.5A EP4251628A1 (fr) | 2020-11-26 | 2021-11-19 | Produit de deshydratation interne du sorbitol de haute purete |
AU2021386448A AU2021386448A1 (en) | 2020-11-26 | 2021-11-19 | Product of internal dehydration of high-purity sorbitol |
US18/254,320 US20240092796A1 (en) | 2020-11-26 | 2021-11-19 | Product of internal dehydration of high-purity sorbitol |
CA3198310A CA3198310A1 (fr) | 2020-11-26 | 2021-11-19 | Produit de deshydratation interne du sorbitol de haute purete |
JP2023528216A JP2023550909A (ja) | 2020-11-26 | 2021-11-19 | 高純度ソルビトールの内部脱水生成物 |
CN202180079630.0A CN116601154A (zh) | 2020-11-26 | 2021-11-19 | 高纯度山梨醇的内部脱水产物 |
KR1020237020566A KR20230112666A (ko) | 2020-11-26 | 2021-11-19 | 고순도 소르비톨의 내부 탈수 생성물 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FRFR2012215 | 2020-11-26 | ||
FR2012215A FR3116533B1 (fr) | 2020-11-26 | 2020-11-26 | Produit de déshydratation interne du sorbitol de haute pureté |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2022111849A1 true WO2022111849A1 (fr) | 2022-06-02 |
Family
ID=74125532
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2021/025454 WO2022111849A1 (fr) | 2020-11-26 | 2021-11-19 | Produit de deshydratation interne du sorbitol de haute purete |
Country Status (9)
Country | Link |
---|---|
US (1) | US20240092796A1 (fr) |
EP (1) | EP4251628A1 (fr) |
JP (1) | JP2023550909A (fr) |
KR (1) | KR20230112666A (fr) |
CN (1) | CN116601154A (fr) |
AU (1) | AU2021386448A1 (fr) |
CA (1) | CA3198310A1 (fr) |
FR (1) | FR3116533B1 (fr) |
WO (1) | WO2022111849A1 (fr) |
Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000041985A1 (fr) | 1999-01-11 | 2000-07-20 | E.I. Du Pont De Nemours And Company | Procede et produits de purification d'alcools de sucre anhydres |
FR2810040A1 (fr) | 2000-06-09 | 2001-12-14 | Roquette Freres | Procede de purification d'une composition contenant au moins un produit de deshydratation interne d'un sucre hydrogene |
US6670033B1 (en) * | 1999-01-11 | 2003-12-30 | E. I. Du Pont De Nemours And Company | Process and products of purification of anhydrosugar alcohols |
EP1882712A1 (fr) | 2005-04-22 | 2008-01-30 | Mitsubishi Chemical Corporation | Polyester derive de la biomasse et son procede de fabrication |
WO2008143269A1 (fr) | 2007-05-17 | 2008-11-27 | Teijin Limited | Procédé de fabrication d'un polycarbonate contenant un composant d'origine végétale |
JP2009191226A (ja) * | 2008-02-18 | 2009-08-27 | Teijin Ltd | 光拡散性ポリカーボネート樹脂組成物 |
EP2223951A1 (fr) * | 2007-12-12 | 2010-09-01 | Mitsubishi Chemical Corporation | Procédé de production de polycarbonate et moulages en polycarbonate |
WO2014178150A1 (fr) * | 2013-04-30 | 2014-11-06 | 第一工業製薬株式会社 | Composition d'anhydride d'alcool de sucre, procédé pour la produire et résine |
EP2848601A1 (fr) * | 2012-05-11 | 2015-03-18 | Samyang Genex Corporation | Procédé de fabrication d'alcool de sucre déshydraté ayant une teneur en ions réduite de façon marquée et des caractéristiques de couleur améliorées |
EP2907799A1 (fr) * | 2012-10-15 | 2015-08-19 | Samyang Genex Corporation | Procédé de préparation d'alcool de sucre anhydre |
JP2015212238A (ja) * | 2014-05-02 | 2015-11-26 | 第一工業製薬株式会社 | 無水糖アルコール組成物、その製造方法及び樹脂 |
KR101736180B1 (ko) | 2015-11-30 | 2017-05-17 | 주식회사 삼양사 | 저장 안정성을 향상시키는 무수당 알코올의 정제 방법 |
KR101736182B1 (ko) | 2015-11-30 | 2017-05-17 | 주식회사 삼양사 | 무수당 알코올의 정제 방법 |
-
2020
- 2020-11-26 FR FR2012215A patent/FR3116533B1/fr active Active
-
2021
- 2021-11-19 CN CN202180079630.0A patent/CN116601154A/zh active Pending
- 2021-11-19 WO PCT/EP2021/025454 patent/WO2022111849A1/fr active Application Filing
- 2021-11-19 US US18/254,320 patent/US20240092796A1/en active Pending
- 2021-11-19 EP EP21814683.5A patent/EP4251628A1/fr active Pending
- 2021-11-19 KR KR1020237020566A patent/KR20230112666A/ko unknown
- 2021-11-19 JP JP2023528216A patent/JP2023550909A/ja active Pending
- 2021-11-19 AU AU2021386448A patent/AU2021386448A1/en active Pending
- 2021-11-19 CA CA3198310A patent/CA3198310A1/fr active Pending
Patent Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000041985A1 (fr) | 1999-01-11 | 2000-07-20 | E.I. Du Pont De Nemours And Company | Procede et produits de purification d'alcools de sucre anhydres |
EP1140733A1 (fr) * | 1999-01-11 | 2001-10-10 | E.I. Dupont De Nemours And Company | Procede et produits de purification d'alcools de sucre anhydres |
US6670033B1 (en) * | 1999-01-11 | 2003-12-30 | E. I. Du Pont De Nemours And Company | Process and products of purification of anhydrosugar alcohols |
FR2810040A1 (fr) | 2000-06-09 | 2001-12-14 | Roquette Freres | Procede de purification d'une composition contenant au moins un produit de deshydratation interne d'un sucre hydrogene |
US20040110969A1 (en) * | 2000-06-09 | 2004-06-10 | Guy Fleche | Method for purifying a composition containing at least one internal dehydration product of a hydrogenated sugar |
EP1882712A1 (fr) | 2005-04-22 | 2008-01-30 | Mitsubishi Chemical Corporation | Polyester derive de la biomasse et son procede de fabrication |
WO2008143269A1 (fr) | 2007-05-17 | 2008-11-27 | Teijin Limited | Procédé de fabrication d'un polycarbonate contenant un composant d'origine végétale |
EP2223951A1 (fr) * | 2007-12-12 | 2010-09-01 | Mitsubishi Chemical Corporation | Procédé de production de polycarbonate et moulages en polycarbonate |
JP2009191226A (ja) * | 2008-02-18 | 2009-08-27 | Teijin Ltd | 光拡散性ポリカーボネート樹脂組成物 |
EP2848601A1 (fr) * | 2012-05-11 | 2015-03-18 | Samyang Genex Corporation | Procédé de fabrication d'alcool de sucre déshydraté ayant une teneur en ions réduite de façon marquée et des caractéristiques de couleur améliorées |
EP2907799A1 (fr) * | 2012-10-15 | 2015-08-19 | Samyang Genex Corporation | Procédé de préparation d'alcool de sucre anhydre |
WO2014178150A1 (fr) * | 2013-04-30 | 2014-11-06 | 第一工業製薬株式会社 | Composition d'anhydride d'alcool de sucre, procédé pour la produire et résine |
JP2015212238A (ja) * | 2014-05-02 | 2015-11-26 | 第一工業製薬株式会社 | 無水糖アルコール組成物、その製造方法及び樹脂 |
KR101736180B1 (ko) | 2015-11-30 | 2017-05-17 | 주식회사 삼양사 | 저장 안정성을 향상시키는 무수당 알코올의 정제 방법 |
KR101736182B1 (ko) | 2015-11-30 | 2017-05-17 | 주식회사 삼양사 | 무수당 알코올의 정제 방법 |
Also Published As
Publication number | Publication date |
---|---|
KR20230112666A (ko) | 2023-07-27 |
JP2023550909A (ja) | 2023-12-06 |
FR3116533A1 (fr) | 2022-05-27 |
CA3198310A1 (fr) | 2022-06-02 |
EP4251628A1 (fr) | 2023-10-04 |
AU2021386448A1 (en) | 2023-06-22 |
FR3116533B1 (fr) | 2023-08-04 |
US20240092796A1 (en) | 2024-03-21 |
CN116601154A (zh) | 2023-08-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1446373B1 (fr) | Procede de preparation d'une composition contenant au moins un produit de deshydratation interne d'un sucre hydrogene | |
EP1287000B1 (fr) | Procede de purification d'une composition contenant au moins un produit de deshydratation interne d'un sucre hydrogene | |
EP1863821B1 (fr) | Procédé de préparation de compositions de diester(s) de dianhydrohexitol | |
HUE029135T2 (en) | Process for the preparation of anhydrous sugar alcohols | |
FR2669635A1 (fr) | Procede de fabrication d'hydroxymethylfurfural (hmf) du purete elevee. | |
JP2006316025A (ja) | 無水糖アルコール組成物の精製方法および製造方法ならびに精製製品 | |
EP2694569B1 (fr) | Procede de fabrication de polycarbonate a partir de dialkylcarbonate de dianhydrohexitol | |
EP3008059B1 (fr) | Procédé pour la préparation d'acétals cycliques alkyl à longues chaînes, à base de sucres | |
CA2393715A1 (fr) | Procede de preparation d'une composition d'ester d'acide lactique et son utilisation en tant que solvant | |
WO2022111849A1 (fr) | Produit de deshydratation interne du sorbitol de haute purete | |
JP6276775B2 (ja) | 着色を改善するためのイソヘキシド生成物の水素化 | |
CA2911044A1 (fr) | Procede de stabilisation d'une composition contenant au moins un produit de deshydratation interne d'un sucre hydrogene, composition obtenue et ses utilisations | |
US20030050499A1 (en) | Process for production of high-purity bis-beta-hydroxyethyl terephthalate | |
EP0187798B1 (fr) | Procede de synthese d'aldosides ou d'oligoaldosides d'alkyle, de cycloalkyle ou d'alcenyle | |
US9266900B2 (en) | Additives for improved isohexide products | |
FR2465752A1 (fr) | Procede de production de 2,2,4-trimethyl-1,2-dihydroquinoleine polymerisee | |
EP0266815B1 (fr) | Procédé pour la fabrication de l'acide bêta-hydroxybutyrique et de ses sels par hydrolyse d'oligomères de l'acide bêta-hydroxybutyrique en milieu basique | |
FR3141175A1 (fr) | Solide bis(2-hydroxyethyle) terephtalate presentant une forme cristalline particuliere | |
KR20220055103A (ko) | 순도가 개선된 무수당 알코올의 디에테르 제조 방법 | |
DE19625265A1 (de) | Verfahren zur Herstellung von aliphatischen Sechsringcarbonaten | |
BE584756A (fr) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 21814683 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 3198310 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2023528216 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 18254320 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 202180079630.0 Country of ref document: CN |
|
ENP | Entry into the national phase |
Ref document number: 20237020566 Country of ref document: KR Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 2021386448 Country of ref document: AU Date of ref document: 20211119 Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 2021814683 Country of ref document: EP Effective date: 20230626 |