DD238787A5 - Verfahren zur herstellung von alkylenglykolen - Google Patents

Verfahren zur herstellung von alkylenglykolen Download PDF

Info

Publication number: DD238787A5
Authority: DD; German Democratic Republic
Prior art keywords: item; water; metalate; anion; alkylene
Prior art date: 1984-03-28

Application number

DD85274450A

Other languages

German (de)

English (en)

Inventor

Brain T Keen

Original Assignee

��@��@��Kk��

Priority date (The priority date 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 date listed.)

1984-03-28

Filing date

1985-03-26

Publication date

1986-09-03

1985-03-26 Application filed by ��@��@��Kk�� filed Critical ��@��@��Kk��

1986-09-03 Publication of DD238787A5 publication Critical patent/DD238787A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 87
230000008569 process Effects 0.000 title claims abstract description 52
238000002360 preparation method Methods 0.000 title claims description 9
150000002334 glycols Chemical class 0.000 title abstract description 8
150000001450 anions Chemical class 0.000 claims abstract description 105
125000002947 alkylene group Chemical group 0.000 claims abstract description 65
150000001768 cations Chemical class 0.000 claims abstract description 55
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 55
230000007062 hydrolysis Effects 0.000 claims abstract description 47
239000000463 material Substances 0.000 claims abstract description 39
230000000087 stabilizing effect Effects 0.000 claims abstract description 24
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 104
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 84
-1 alkylene glycols Chemical class 0.000 claims description 77
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 58
239000007787 solid Substances 0.000 claims description 32
239000012071 phase Substances 0.000 claims description 28
230000000536 complexating effect Effects 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 25
125000000962 organic group Chemical group 0.000 claims description 21
229910052751 metal Inorganic materials 0.000 claims description 20
239000002184 metal Substances 0.000 claims description 20
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
239000003957 anion exchange resin Substances 0.000 claims description 18
239000008346 aqueous phase Substances 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 17
229910052783 alkali metal Inorganic materials 0.000 claims description 13
150000001340 alkali metals Chemical class 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
230000003647 oxidation Effects 0.000 claims description 10
238000007254 oxidation reaction Methods 0.000 claims description 10
125000001453 quaternary ammonium group Chemical group 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
230000002708 enhancing effect Effects 0.000 claims description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
150000003512 tertiary amines Chemical class 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
239000007791 liquid phase Substances 0.000 claims description 5
229910052698 phosphorus Inorganic materials 0.000 claims description 5
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
229910052785 arsenic Chemical group 0.000 claims description 4
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000008096 xylene Substances 0.000 claims description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
238000010924 continuous production Methods 0.000 claims description 3
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
239000011574 phosphorus Chemical group 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000000732 arylene group Chemical group 0.000 claims description 2
238000000151 deposition Methods 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
125000005496 phosphonium group Chemical group 0.000 claims description 2
125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 2
PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
229910001413 alkali metal ion Inorganic materials 0.000 claims 2
238000006243 chemical reaction Methods 0.000 description 42
239000011347 resin Substances 0.000 description 41
229920005989 resin Polymers 0.000 description 41
239000000047 product Substances 0.000 description 38
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 26
230000001965 increasing effect Effects 0.000 description 17
239000007788 liquid Substances 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 14
239000001569 carbon dioxide Substances 0.000 description 13
229910002092 carbon dioxide Inorganic materials 0.000 description 13
239000000376 reactant Substances 0.000 description 13
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
230000015556 catabolic process Effects 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
238000006731 degradation reaction Methods 0.000 description 11
239000002253 acid Substances 0.000 description 10
LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
230000000694 effects Effects 0.000 description 9
238000004519 manufacturing process Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
229920000642 polymer Polymers 0.000 description 8
239000011521 glass Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
235000015393 sodium molybdate Nutrition 0.000 description 7
239000011684 sodium molybdate Substances 0.000 description 7
TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 7
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
230000002411 adverse Effects 0.000 description 6
229910052784 alkaline earth metal Inorganic materials 0.000 description 6
150000001342 alkaline earth metals Chemical class 0.000 description 6
229910052742 iron Inorganic materials 0.000 description 6
238000011068 loading method Methods 0.000 description 6
229910052750 molybdenum Inorganic materials 0.000 description 6
239000011733 molybdenum Substances 0.000 description 6
229920001467 poly(styrenesulfonates) Polymers 0.000 description 6
239000002002 slurry Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 6
229910052721 tungsten Inorganic materials 0.000 description 6
239000010937 tungsten Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
229920000728 polyester Polymers 0.000 description 5
239000012429 reaction media Substances 0.000 description 5
238000011084 recovery Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
239000010949 copper Substances 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
229910001220 stainless steel Inorganic materials 0.000 description 4
239000010935 stainless steel Substances 0.000 description 4
229910052720 vanadium Inorganic materials 0.000 description 4
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
239000011701 zinc Substances 0.000 description 4
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
108010057081 Merozoite Surface Protein 1 Proteins 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical group 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000011491 glass wool Substances 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000005191 phase separation Methods 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
229920001296 polysiloxane Polymers 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910052702 rhenium Inorganic materials 0.000 description 3
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
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 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
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OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
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125000000623 heterocyclic group Chemical group 0.000 description 2
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239000011630 iodine Substances 0.000 description 2
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INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
238000005342 ion exchange Methods 0.000 description 2
ALTWGIIQPLQAAM-UHFFFAOYSA-N metavanadate Chemical compound [O-][V](=O)=O ALTWGIIQPLQAAM-UHFFFAOYSA-N 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
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UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 2
230000035699 permeability Effects 0.000 description 2
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150000003018 phosphorus compounds Chemical class 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000012545 processing Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
229910000077 silane Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
GRAKJTASWCEOQI-UHFFFAOYSA-N tridodecylphosphane Chemical compound CCCCCCCCCCCCP(CCCCCCCCCCCC)CCCCCCCCCCCC GRAKJTASWCEOQI-UHFFFAOYSA-N 0.000 description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
239000010457 zeolite Substances 0.000 description 2
SUTQSIHGGHVXFK-UHFFFAOYSA-N 1,2,2-trifluoroethenylbenzene Chemical compound FC(F)=C(F)C1=CC=CC=C1 SUTQSIHGGHVXFK-UHFFFAOYSA-N 0.000 description 1
WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
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230000036961 partial effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
RPGWZZNNEUHDAQ-UHFFFAOYSA-O phenylphosphanium Chemical compound [PH3+]C1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-O 0.000 description 1
150000003003 phosphines Chemical group 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
229920002492 poly(sulfone) Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920001281 polyalkylene Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000003822 preparative gas chromatography Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000010926 purge Methods 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000007670 refining Methods 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
230000009291 secondary effect Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
SBCUXVQZGCKZET-UHFFFAOYSA-N tetrabenzylphosphanium Chemical compound C=1C=CC=CC=1C[P+](CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 SBCUXVQZGCKZET-UHFFFAOYSA-N 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
UOBBAWATEUXIQF-UHFFFAOYSA-N tetradodecylazanium Chemical compound CCCCCCCCCCCC[N+](CCCCCCCCCCCC)(CCCCCCCCCCCC)CCCCCCCCCCCC UOBBAWATEUXIQF-UHFFFAOYSA-N 0.000 description 1
IDPHCYBLJHMWAE-UHFFFAOYSA-N tetradodecylphosphanium Chemical compound CCCCCCCCCCCC[P+](CCCCCCCCCCCC)(CCCCCCCCCCCC)CCCCCCCCCCCC IDPHCYBLJHMWAE-UHFFFAOYSA-N 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
YFZDLRVCXDBOPH-UHFFFAOYSA-N tetraheptylazanium Chemical compound CCCCCCC[N+](CCCCCCC)(CCCCCCC)CCCCCCC YFZDLRVCXDBOPH-UHFFFAOYSA-N 0.000 description 1
ATWHYDCJSAROQC-UHFFFAOYSA-N tetraheptylphosphanium Chemical compound CCCCCCC[P+](CCCCCCC)(CCCCCCC)CCCCCCC ATWHYDCJSAROQC-UHFFFAOYSA-N 0.000 description 1
SMYCBOLFQFMGRH-UHFFFAOYSA-N tetrakis(2-methylpropyl)phosphanium Chemical compound CC(C)C[P+](CC(C)C)(CC(C)C)CC(C)C SMYCBOLFQFMGRH-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
KNANANSBRPCBAH-UHFFFAOYSA-N tetraoctadecylazanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](CCCCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC KNANANSBRPCBAH-UHFFFAOYSA-N 0.000 description 1
BWXDLFXRIPTPKN-UHFFFAOYSA-N tetraoctadecylphosphanium Chemical compound CCCCCCCCCCCCCCCCCC[P+](CCCCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC BWXDLFXRIPTPKN-UHFFFAOYSA-N 0.000 description 1
HRLYFPKUYKFYJE-UHFFFAOYSA-N tetraoxorhenate(2-) Chemical compound [O-][Re]([O-])(=O)=O HRLYFPKUYKFYJE-UHFFFAOYSA-N 0.000 description 1
CZMILNXHOAKSBR-UHFFFAOYSA-N tetraphenylazanium Chemical compound C1=CC=CC=C1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CZMILNXHOAKSBR-UHFFFAOYSA-N 0.000 description 1
USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 description 1
SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
FIRQXKNYMDWNSI-UHFFFAOYSA-N triethylphosphane triphenylphosphane Chemical compound C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)P(CC)CC FIRQXKNYMDWNSI-UHFFFAOYSA-N 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
YWWDBCBWQNCYNR-UHFFFAOYSA-O trimethylphosphanium Chemical compound C[PH+](C)C YWWDBCBWQNCYNR-UHFFFAOYSA-O 0.000 description 1
KJFAJLYXKTVJDA-UHFFFAOYSA-N trioctadecylphosphane Chemical compound CCCCCCCCCCCCCCCCCCP(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC KJFAJLYXKTVJDA-UHFFFAOYSA-N 0.000 description 1
ODHXBMXNKOYIBV-UHFFFAOYSA-O triphenylazanium Chemical compound C1=CC=CC=C1[NH+](C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-O 0.000 description 1
150000003658 tungsten compounds Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD85274450A 1984-03-28 1985-03-26 Verfahren zur herstellung von alkylenglykolen DD238787A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/594,267 US4579983A (en)	1984-03-28	1984-03-28	Process for the hydrolysis of alkylene oxides using organometalates

Publications (1)

Publication Number	Publication Date
DD238787A5 true DD238787A5 (de)	1986-09-03

Family

ID=24378211

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85274450A DD238787A5 (de)	1984-03-28	1985-03-26	Verfahren zur herstellung von alkylenglykolen

Country Status (13)

Country	Link
US (1)	US4579983A (fr)
EP (1)	EP0160329B1 (fr)
JP (1)	JPS61501707A (fr)
KR (1)	KR910007548B1 (fr)
AT (1)	ATE58717T1 (fr)
AU (1)	AU587185B2 (fr)
BR (1)	BR8506208A (fr)
CA (1)	CA1263874A (fr)
DD (1)	DD238787A5 (fr)
DE (1)	DE3580691D1 (fr)
ES (1)	ES8608465A1 (fr)
PL (1)	PL252604A1 (fr)
WO (1)	WO1985004392A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU580300B2 (en) *	1984-03-28	1989-01-12	Union Carbide Corporation	Alcoholates of metalate anions and glycols produced from them
US4701571A (en) *	1986-06-30	1987-10-20	Union Carbide Corporation	Process for the production of alkylene glycols with metalate-containing solids
US5798412A (en) *	1997-07-16	1998-08-25	Huntsman Petrochemical Corporation	Alkylene glycol production using carbon catalysts
US6156942A (en) *	1998-12-14	2000-12-05	Shell Oil Company	Catalyst stabilizing additive in the hydrolysis of alkylene oxides
MY121124A (en) *	1998-12-14	2005-12-30	Shell Int Research	Catalyst stabilising additive in the hydrolysis of alkylene oxides

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4160116A (en) *	1978-08-28	1979-07-03	Showa Denko K.K.	Process for the production of alkylene glycols
CA1120955A (fr) *	1979-07-09	1982-03-30	Toshihiko Kumazawa	Procede de fabrication d'alcoylene glycols
JPS5673035A (en) *	1979-11-19	1981-06-17	Nippon Shokubai Kagaku Kogyo Co Ltd	Preparation of alkylene glycol
US4393254A (en) *	1981-01-12	1983-07-12	Texaco Inc.	Process for the production of alkylene glycols
JPS6056141B2 (ja) *	1981-02-24	1985-12-09	株式会社日本触媒	アルキレングリコールの製造方法
US4551566A (en) *	1982-09-30	1985-11-05	Union Carbide Corporation	Process for the production of alkylene glycols

1984
- 1984-03-28 US US06/594,267 patent/US4579983A/en not_active Expired - Lifetime
1985
- 1985-03-15 CA CA000476710A patent/CA1263874A/fr not_active Expired
- 1985-03-26 DD DD85274450A patent/DD238787A5/de unknown
- 1985-03-27 DE DE8585200485T patent/DE3580691D1/de not_active Expired - Lifetime
- 1985-03-27 AT AT85200485T patent/ATE58717T1/de not_active IP Right Cessation
- 1985-03-27 EP EP85200485A patent/EP0160329B1/fr not_active Expired - Lifetime
- 1985-03-27 ES ES541612A patent/ES8608465A1/es not_active Expired
- 1985-03-27 PL PL25260485A patent/PL252604A1/xx unknown
- 1985-03-28 JP JP60501557A patent/JPS61501707A/ja active Granted
- 1985-03-28 WO PCT/US1985/000509 patent/WO1985004392A1/fr not_active Ceased
- 1985-03-28 KR KR1019850700347A patent/KR910007548B1/ko not_active Expired
- 1985-03-28 BR BR8506208A patent/BR8506208A/pt unknown
- 1985-03-28 AU AU42174/85A patent/AU587185B2/en not_active Ceased

Also Published As

Publication number	Publication date
CA1263874A (fr)	1989-12-12
KR860700029A (ko)	1986-01-31
JPH0333141B2 (fr)	1991-05-16
WO1985004392A1 (fr)	1985-10-10
US4579983A (en)	1986-04-01
EP0160329A1 (fr)	1985-11-06
AU4217485A (en)	1985-11-01
ATE58717T1 (de)	1990-12-15
DE3580691D1 (de)	1991-01-10
JPS61501707A (ja)	1986-08-14
BR8506208A (pt)	1986-04-15
KR910007548B1 (ko)	1991-09-27
PL252604A1 (en)	1985-12-03
EP0160329B1 (fr)	1990-11-28
ES541612A0 (es)	1986-06-16
ES8608465A1 (es)	1986-06-16
AU587185B2 (en)	1989-08-10

Publication	Publication Date	Title
US4560813A (en)	1985-12-24	Processes for the production of alkylene glycol in the presence of organometalate
DD238786A5 (de)	1986-09-03	Verfahren zur herstellung von alkylenglykol
US4982021A (en)	1991-01-01	Process for the production of alkylene glycols with metalate-containing solid
CA1263670A (fr)	1989-12-05	Production d'alkyleneglycols
DD238787A5 (de)	1986-09-03	Verfahren zur herstellung von alkylenglykolen
DE2340395B2 (de)	1980-09-04	Verfahren zur Herstellung von vicinalen Glykolestern
DD238799A5 (de)	1986-09-03	Verfahren zur herstellung von vicinalem dioxyalkylen-organometallat
US5227538A (en)	1993-07-13	Catalytic asymmetric reduction of ketones using metal catalysts
CA1268784A (fr)	1990-05-08	Procede pour la production d'arylene glycols en presence de matieres solides contenant de la metalate
US4585883A (en)	1986-04-29	Preparation of organometalates
DE602004005702T2 (de)	2007-12-27	Verfahren zur entfernung von organischen halogenhaltigen verbindungen
JPH0576457B2 (fr)	1993-10-22
CA1263410A (fr)	1989-11-28	Preparation de monoalcoyleneglycols en deux etapes
EP1123912B1 (fr)	2003-08-20	Procédé pour l'élimination de l'oxygène dissout du phénol
US3121751A (en)	1964-02-18	Production of purified orthoformic esters
DE68915694T2 (de)	1994-09-15	Verfahren zur Herstellung von verzweigten 1,3-Glykolen und ihren Monoestern.
EP1042258A1 (fr)	2000-10-11	Procede de preparation d'alkyleneglycol
KR920000905B1 (ko)	1992-01-31	메탈레이트 음이온의 유기염 및 이를 이용한 알킬렌 글리콜의 제조방법
KR20200006838A (ko)	2020-01-21	폐유기용매 정제 방법