KR102449054B1 - 글리콜산의 제조 방법 - Google Patents
글리콜산의 제조 방법 Download PDFInfo
- Publication number
- KR102449054B1 KR102449054B1 KR1020197010429A KR20197010429A KR102449054B1 KR 102449054 B1 KR102449054 B1 KR 102449054B1 KR 1020197010429 A KR1020197010429 A KR 1020197010429A KR 20197010429 A KR20197010429 A KR 20197010429A KR 102449054 B1 KR102449054 B1 KR 102449054B1
- Authority
- KR
- South Korea
- Prior art keywords
- reactor
- bara
- glycolic acid
- acid
- product stream
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 title claims abstract description 167
- 238000000034 method Methods 0.000 title claims description 57
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 141
- 239000003054 catalyst Substances 0.000 claims abstract description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 65
- 238000005886 esterification reaction Methods 0.000 claims abstract description 60
- 239000011593 sulfur Substances 0.000 claims abstract description 56
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 56
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 55
- 238000005810 carbonylation reaction Methods 0.000 claims abstract description 54
- -1 alkyl glycolate Chemical compound 0.000 claims abstract description 53
- 230000006315 carbonylation Effects 0.000 claims abstract description 34
- 230000032050 esterification Effects 0.000 claims abstract description 31
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 27
- 239000012535 impurity Substances 0.000 claims abstract description 23
- 238000004821 distillation Methods 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000004064 recycling Methods 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims description 60
- 230000007062 hydrolysis Effects 0.000 claims description 31
- 238000006460 hydrolysis reaction Methods 0.000 claims description 31
- 150000002148 esters Chemical class 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 16
- 238000005342 ion exchange Methods 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 6
- 238000000066 reactive distillation Methods 0.000 claims description 6
- 150000003457 sulfones Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical group O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical group O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- 239000000047 product Substances 0.000 description 48
- 241000894007 species Species 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000002253 acid Substances 0.000 description 29
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 27
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 18
- 239000003377 acid catalyst Substances 0.000 description 17
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 229920001296 polysiloxane Polymers 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 10
- 239000002815 homogeneous catalyst Substances 0.000 description 10
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 125000005103 alkyl silyl group Chemical group 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 239000010457 zeolite Substances 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000003456 ion exchange resin Substances 0.000 description 8
- 229920003303 ion-exchange polymer Polymers 0.000 description 8
- 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 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 239000002638 heterogeneous catalyst Substances 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000000542 sulfonic acid group Chemical group 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 4
- 238000004088 simulation Methods 0.000 description 4
- 239000011973 solid acid Substances 0.000 description 4
- ICPWFHKNYYRBSZ-UHFFFAOYSA-M 2-methoxypropanoate Chemical compound COC(C)C([O-])=O ICPWFHKNYYRBSZ-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 102100021277 Beta-secretase 2 Human genes 0.000 description 3
- 101710150190 Beta-secretase 2 Proteins 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical group [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000011949 solid catalyst Substances 0.000 description 3
- NRPMOERNXKBKQR-UHFFFAOYSA-N 2-trihydroxysilylethanesulfonic acid Chemical compound O[Si](O)(O)CCS(O)(=O)=O NRPMOERNXKBKQR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920000954 Polyglycolide Polymers 0.000 description 2
- 241000183024 Populus tremula Species 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- KUCRTUQUAYLJDC-UHFFFAOYSA-N methyl 2-(2-methoxy-2-oxoethoxy)acetate Chemical compound COC(=O)COCC(=O)OC KUCRTUQUAYLJDC-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- QIYAADGGFQEDSN-UHFFFAOYSA-N 1-trihydroxysilylpropane-1-sulfonic acid Chemical compound CCC([Si](O)(O)O)S(O)(=O)=O QIYAADGGFQEDSN-UHFFFAOYSA-N 0.000 description 1
- DQPDAFDEASYJKB-UHFFFAOYSA-N 2-(2-methoxy-2-oxoethoxy)acetic acid Chemical compound COC(=O)COCC(O)=O DQPDAFDEASYJKB-UHFFFAOYSA-N 0.000 description 1
- WYTQXLFLAMZNNZ-UHFFFAOYSA-N 3-trihydroxysilylpropane-1-sulfonic acid Chemical compound O[Si](O)(O)CCCS(O)(=O)=O WYTQXLFLAMZNNZ-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910017116 Fe—Mo Inorganic materials 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 229920005565 cyclic polymer Polymers 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 238000010915 one-step procedure Methods 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 230000036967 uncompetitive effect Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/145—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide with simultaneous oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/06—Glycolic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1615762.0A GB201615762D0 (en) | 2016-09-16 | 2016-09-16 | Process |
| GB1615762.0 | 2016-09-16 | ||
| PCT/GB2017/052740 WO2018051115A1 (en) | 2016-09-16 | 2017-09-15 | Process for the production of glycolic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20190047019A KR20190047019A (ko) | 2019-05-07 |
| KR102449054B1 true KR102449054B1 (ko) | 2022-09-30 |
Family
ID=57288828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020197010429A Active KR102449054B1 (ko) | 2016-09-16 | 2017-09-15 | 글리콜산의 제조 방법 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US10640443B2 (enExample) |
| EP (1) | EP3512828B1 (enExample) |
| JP (1) | JP6953518B2 (enExample) |
| KR (1) | KR102449054B1 (enExample) |
| CN (1) | CN109715596B (enExample) |
| AU (1) | AU2017327999B2 (enExample) |
| BR (1) | BR112019005028B1 (enExample) |
| EA (1) | EA036428B1 (enExample) |
| GB (2) | GB201615762D0 (enExample) |
| WO (1) | WO2018051115A1 (enExample) |
| ZA (1) | ZA201901641B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20210355100A1 (en) * | 2018-10-29 | 2021-11-18 | Pujing Chemical Industry Co., Ltd. | Glycolide Production With Low Solid Residue |
| US20220306563A1 (en) * | 2019-06-27 | 2022-09-29 | Rhodia Operations | Method for preparing glycolic acid |
| CN112521265B (zh) * | 2020-12-09 | 2022-08-09 | 浙江联盛化学股份有限公司 | 一种连续化生产乙醇酸的方法 |
| CN114853605B (zh) * | 2021-02-03 | 2024-03-19 | 中国科学院大连化学物理研究所 | 甲氧基乙酸甲酯和甲氧基乙酸水解制取乙醇酸和乙醇酸甲酯的方法 |
| WO2022165662A1 (zh) * | 2021-02-03 | 2022-08-11 | 中国科学院大连化学物理研究所 | 甲氧基乙酸甲酯和甲氧基乙酸水解制取乙醇酸和乙醇酸甲酯的方法 |
| CN113952906A (zh) * | 2021-10-27 | 2022-01-21 | 南京延长反应技术研究院有限公司 | 一种制备羟基乙酸的微界面反应装置及方法 |
| CN114057564B (zh) * | 2021-12-09 | 2023-10-03 | 上海卓笙环保科技有限公司 | 一种基于碳酸体系作为无痕催化剂水解乙醇酸酯的方法 |
| GB202201979D0 (en) * | 2022-02-15 | 2022-03-30 | Johnson Matthey Plc | Process |
| CN115160122A (zh) * | 2022-08-26 | 2022-10-11 | 东华工程科技股份有限公司 | 一种乙醇酸甲酯水解制乙醇酸的新工艺 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040138409A1 (en) | 2002-07-12 | 2004-07-15 | Toshio Hayashi | Method for producing diol derivatives |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2152852A (en) | 1936-12-31 | 1939-04-04 | Du Pont | Process for manufacture of glycolic acid |
| US2285444A (en) | 1940-06-14 | 1942-06-09 | American Automatic Typewriter | Link connection for automatic typewriters |
| US2443482A (en) | 1946-08-06 | 1948-06-15 | Du Pont | Continuous glycolic acid process |
| US3859349A (en) * | 1973-02-15 | 1975-01-07 | Du Pont | Purification of hydroxyacetic acid |
| US3911003A (en) | 1974-06-19 | 1975-10-07 | Chevron Res | Process for the production of glycolic acid and oxydiacetic acid |
| US4016208A (en) | 1974-06-19 | 1977-04-05 | Chevron Research Company | Acid production |
| IT1017804B (it) | 1974-08-01 | 1977-08-10 | Montedison Spa | Procedimento per la preparazione di acido glicolico e suoi polimeri |
| CA1077517A (en) | 1975-04-23 | 1980-05-13 | Ppg Industries, Inc. | Process for the preparation of hydroxy-carboxylic acids and derivatives |
| US4087470A (en) | 1976-06-23 | 1978-05-02 | Chevron Research Company | Process for the production of ethylene glycol |
| DE2652072A1 (de) | 1976-11-15 | 1978-05-24 | Hoechst Ag | Verfahren zur herstellung von glykolsaeureestern |
| US4188494A (en) | 1977-04-25 | 1980-02-12 | Chevron Research Company | Hydrogen fluoride removal from glycolic acid |
| US4136112A (en) | 1977-06-24 | 1979-01-23 | Chevron Research Company | Process for preparing glycolic acid from formaldehyde using acetic acid |
| US4140866A (en) | 1978-03-30 | 1979-02-20 | Ppg Industries, Inc. | Preparation of sulfate free glycolic acid ester |
| JPS5673042A (en) | 1979-11-20 | 1981-06-17 | Mitsubishi Gas Chem Co Inc | Preparation of glycolic acid |
| US4431997A (en) | 1981-02-18 | 1984-02-14 | Motorola Inc. | Compound element for image element antennas |
| DE3133353C2 (de) | 1981-08-22 | 1985-07-18 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von Glykolsäure oder ihrer Ester |
| US4431486A (en) * | 1982-04-12 | 1984-02-14 | E. I. Du Pont De Nemours And Company | Azeotropic distillation of hydroxyacetic acid |
| JPS59139341A (ja) | 1983-01-20 | 1984-08-10 | Mitsubishi Gas Chem Co Inc | ヒドロキシカルボン酸誘導体の製造方法 |
| JPS60260538A (ja) * | 1984-06-07 | 1985-12-23 | Agency Of Ind Science & Technol | グリコ−ル酸エステルの製造法 |
| US4824997A (en) * | 1988-01-25 | 1989-04-25 | Monsanto Company | Method for preparation of alkyl glycolates |
| KR950011114B1 (ko) | 1991-07-19 | 1995-09-28 | 포항종합제철주식회사 | 메틸글리콜레이트의 제조공정 |
| KR950013078B1 (ko) | 1992-10-28 | 1995-10-24 | 포항종합제철주식회사 | 글리콜산 및 글리콜산 에스테르의 제조방법 |
| JP2503178B2 (ja) | 1993-01-29 | 1996-06-05 | 日揮株式会社 | グリコ―ル酸、グリコ―ル酸エステルまたはポリグリコリドの製造方法 |
| KR0124821B1 (ko) | 1993-12-24 | 1997-12-01 | 조말수 | 산성 반응 용액중의 메틸글리콜레이트 분리방법 |
| KR100356768B1 (ko) | 1994-04-19 | 2003-09-02 | 니폰 가야꾸 가부시끼가이샤 | 분산염료조성물및이를사용한소수성섬유물질의염색방법 |
| KR0155273B1 (ko) | 1995-05-24 | 1998-12-15 | 김광호 | 대역 통과 필터 기능을 겸비한 위상 변위 장치 및 그 방법 |
| JPH11335319A (ja) * | 1998-05-19 | 1999-12-07 | Nippon Shokubai Co Ltd | α−ヒドロキシカルボン酸の製造方法 |
| US6376723B2 (en) | 1999-12-29 | 2002-04-23 | Shell Oil Company | Process for the carbonylation of formaldehyde |
| GB0100470D0 (en) | 2001-01-09 | 2001-02-21 | Queen Mary & Westfield College | Organopolysiloxanes containing phosphonic groups, methods for the production and use thereof |
| JP3772238B2 (ja) * | 2002-07-12 | 2006-05-10 | 株式会社日本触媒 | α−ヒドロキシカルボン酸の製造方法 |
| JP2004043682A (ja) * | 2002-07-12 | 2004-02-12 | Nippon Shokubai Co Ltd | ポリグリコール酸の製造方法 |
| JP4195934B2 (ja) * | 2004-03-01 | 2008-12-17 | 独立行政法人産業技術総合研究所 | イオン性液体を用いたグリコール酸およびそのエステルの製造方法 |
| GB0417344D0 (en) | 2004-08-04 | 2004-09-08 | Phosphonics Ltd | Substituted organopolysiloxanes and use thereof |
| US9982095B2 (en) | 2004-08-04 | 2018-05-29 | Phosphonics Ltd | Substituted organopolysiloxanes and use thereof |
| GB0602811D0 (en) | 2006-02-10 | 2006-03-22 | Phosphonics Ltd | Substituted Organopolysiloxanes And Use Thereof |
| GB0720579D0 (en) | 2007-10-20 | 2007-11-28 | Phosphonics Ltd | Functionalised materials and uses thereof |
| WO2009140787A1 (en) | 2008-05-20 | 2009-11-26 | Dalian Institute Of Chemical Physics, Chinese Academy Of Sciences | Process for production of glycolic acid |
| US8501987B2 (en) | 2008-05-20 | 2013-08-06 | Dalian Institute Of Chemical Physics | Process for production of glycolic acid |
| US8765999B2 (en) * | 2012-03-27 | 2014-07-01 | Eastman Chemical Company | Hydrocarboxylation of formaldehyde in the presence of a higher order carboxylic acid and a homogeneous catalyst |
| JP2015517992A (ja) * | 2012-03-27 | 2015-06-25 | イーストマン ケミカル カンパニー | 酸触媒の回収及びリサイクル方法 |
| US9040748B2 (en) * | 2012-06-08 | 2015-05-26 | Eastman Chemical Company | Hydrocarboxylation of aqueous formaldehyde using a dehydrating recycle stream to decrease water concentration |
| CN103833548A (zh) * | 2012-11-20 | 2014-06-04 | 中国科学院兰州化学物理研究所 | 一种乙醇酸甲酯的制备方法 |
| GB201505977D0 (en) | 2015-04-08 | 2015-05-20 | Johnson Matthey Davy Technologies Ltd | Catalyst system and process |
| GB201505981D0 (en) | 2015-04-08 | 2015-05-20 | Johnson Matthey Davy Technologies Ltd | Process |
-
2016
- 2016-09-16 GB GBGB1615762.0A patent/GB201615762D0/en not_active Ceased
-
2017
- 2017-09-15 JP JP2019514823A patent/JP6953518B2/ja active Active
- 2017-09-15 EP EP17771848.3A patent/EP3512828B1/en active Active
- 2017-09-15 BR BR112019005028-0A patent/BR112019005028B1/pt active IP Right Grant
- 2017-09-15 EA EA201990731A patent/EA036428B1/ru not_active IP Right Cessation
- 2017-09-15 CN CN201780056765.9A patent/CN109715596B/zh active Active
- 2017-09-15 US US16/332,853 patent/US10640443B2/en active Active
- 2017-09-15 WO PCT/GB2017/052740 patent/WO2018051115A1/en not_active Ceased
- 2017-09-15 AU AU2017327999A patent/AU2017327999B2/en active Active
- 2017-09-15 GB GB1714877.6A patent/GB2559641B/en active Active
- 2017-09-15 KR KR1020197010429A patent/KR102449054B1/ko active Active
-
2019
- 2019-03-15 ZA ZA2019/01641A patent/ZA201901641B/en unknown
-
2020
- 2020-04-03 US US16/839,971 patent/US11053186B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040138409A1 (en) | 2002-07-12 | 2004-07-15 | Toshio Hayashi | Method for producing diol derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2559641A (en) | 2018-08-15 |
| GB201714877D0 (en) | 2017-11-01 |
| GB201615762D0 (en) | 2016-11-02 |
| EP3512828A1 (en) | 2019-07-24 |
| AU2017327999B2 (en) | 2020-11-26 |
| AU2017327999A1 (en) | 2019-03-21 |
| US11053186B2 (en) | 2021-07-06 |
| CN109715596A (zh) | 2019-05-03 |
| BR112019005028B1 (pt) | 2022-12-13 |
| JP6953518B2 (ja) | 2021-10-27 |
| GB2559641B (en) | 2019-12-04 |
| EA036428B1 (ru) | 2020-11-10 |
| WO2018051115A1 (en) | 2018-03-22 |
| EP3512828B1 (en) | 2020-11-11 |
| KR20190047019A (ko) | 2019-05-07 |
| JP2019529422A (ja) | 2019-10-17 |
| US10640443B2 (en) | 2020-05-05 |
| US20190248724A1 (en) | 2019-08-15 |
| US20200239395A1 (en) | 2020-07-30 |
| BR112019005028A2 (pt) | 2019-06-18 |
| EA201990731A1 (ru) | 2019-08-30 |
| ZA201901641B (en) | 2021-06-30 |
| CN109715596B (zh) | 2022-05-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102449054B1 (ko) | 글리콜산의 제조 방법 | |
| TWI775884B (zh) | 用於自乙二醇粗料流純化乙二醇之方法 | |
| US10335774B2 (en) | Carbonylation process and catalyst system therefor | |
| US10087131B2 (en) | Process for the production of glycolic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20190411 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20200914 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20220228 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20220902 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20220926 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20220927 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration |