DD202283A5 - Verfahren zur kontinuierlichen herstellung von ethylenglykol - Google Patents
Verfahren zur kontinuierlichen herstellung von ethylenglykol Download PDFInfo
- Publication number
- DD202283A5 DD202283A5 DD81232902A DD23290281A DD202283A5 DD 202283 A5 DD202283 A5 DD 202283A5 DD 81232902 A DD81232902 A DD 81232902A DD 23290281 A DD23290281 A DD 23290281A DD 202283 A5 DD202283 A5 DD 202283A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- stage
- gas
- alcohol
- item
- ethylene glycol
- Prior art date
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 158
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000010924 continuous production Methods 0.000 title claims abstract description 7
- 239000007789 gas Substances 0.000 claims abstract description 159
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 104
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 100
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 80
- 239000007788 liquid Substances 0.000 claims abstract description 60
- 239000003054 catalyst Substances 0.000 claims abstract description 47
- -1 oxalic acid diester Chemical class 0.000 claims abstract description 44
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 36
- 235000006408 oxalic acid Nutrition 0.000 claims abstract description 35
- 150000002148 esters Chemical class 0.000 claims abstract description 33
- 150000005690 diesters Chemical class 0.000 claims abstract description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 11
- 239000002184 metal Substances 0.000 claims abstract description 11
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 9
- 239000011949 solid catalyst Substances 0.000 claims abstract description 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims description 119
- 230000008929 regeneration Effects 0.000 claims description 55
- 238000011069 regeneration method Methods 0.000 claims description 55
- 239000000047 product Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 22
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 14
- 239000006227 byproduct Substances 0.000 claims description 11
- 238000009835 boiling Methods 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 10
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 150000004650 carbonic acid diesters Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000010574 gas phase reaction Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000007792 gaseous phase Substances 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract description 4
- 240000007019 Oxalis corniculata Species 0.000 abstract 1
- 235000016499 Oxalis corniculata Nutrition 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 165
- 239000000203 mixture Substances 0.000 description 77
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 73
- 229960003753 nitric oxide Drugs 0.000 description 43
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 40
- 229910052757 nitrogen Inorganic materials 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 239000001569 carbon dioxide Substances 0.000 description 20
- 229910002092 carbon dioxide Inorganic materials 0.000 description 20
- BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 description 20
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 18
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 14
- 239000007858 starting material Substances 0.000 description 10
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 9
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 8
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 7
- QQZWEECEMNQSTG-UHFFFAOYSA-N Ethyl nitrite Chemical compound CCON=O QQZWEECEMNQSTG-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000008262 pumice Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-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
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-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
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 241000246358 Thymus Species 0.000 description 1
- 235000007303 Thymus vulgaris Nutrition 0.000 description 1
- AEJRNONYXDAILM-UHFFFAOYSA-N [Ba+2].[O-][Cr]([O-])=O Chemical compound [Ba+2].[O-][Cr]([O-])=O AEJRNONYXDAILM-UHFFFAOYSA-N 0.000 description 1
- CXQXWHWPDDUDPI-UHFFFAOYSA-N [Cu+2].[Zn+2].[O-][Cr]([O-])=O.[O-][Cr]([O-])=O Chemical compound [Cu+2].[Zn+2].[O-][Cr]([O-])=O.[O-][Cr]([O-])=O CXQXWHWPDDUDPI-UHFFFAOYSA-N 0.000 description 1
- JWCPKKUXENYVPL-UHFFFAOYSA-N [Mg+2].[O-][Cr]([O-])=O Chemical compound [Mg+2].[O-][Cr]([O-])=O JWCPKKUXENYVPL-UHFFFAOYSA-N 0.000 description 1
- WNVXPUKIBYOUIG-UHFFFAOYSA-N [Mn+2].[O-][Cr]([O-])=O Chemical compound [Mn+2].[O-][Cr]([O-])=O WNVXPUKIBYOUIG-UHFFFAOYSA-N 0.000 description 1
- LRFQSNDOLFTQCR-UHFFFAOYSA-M [O-][Cr](O)(=O)=O.N.[Cu+] Chemical compound [O-][Cr](O)(=O)=O.N.[Cu+] LRFQSNDOLFTQCR-UHFFFAOYSA-M 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- LOMVENUNSWAXEN-NUQCWPJISA-N dimethyl oxalate Chemical group CO[14C](=O)[14C](=O)OC LOMVENUNSWAXEN-NUQCWPJISA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- SKRDXYBATCVEMS-UHFFFAOYSA-N isopropyl nitrite Chemical compound CC(C)ON=O SKRDXYBATCVEMS-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- KAOQVXHBVNKNHA-UHFFFAOYSA-N propyl nitrite Chemical compound CCCON=O KAOQVXHBVNKNHA-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/04—Preparation of esters of nitrous acid
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55120677A JPS6039337B2 (ja) | 1980-09-02 | 1980-09-02 | エチレングリコ−ルの連続的製法 |
| JP12067680A JPS6039336B2 (ja) | 1980-09-02 | 1980-09-02 | エチレングリコ−ルの連続的製法 |
| JP56007175A JPS57122030A (en) | 1981-01-22 | 1981-01-22 | Continuous preparation of ethylene glycol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD202283A5 true DD202283A5 (de) | 1983-09-07 |
Family
ID=27277498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81232902A DD202283A5 (de) | 1980-09-02 | 1981-08-31 | Verfahren zur kontinuierlichen herstellung von ethylenglykol |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4453026A (en, 2012) |
| EP (1) | EP0046983B1 (en, 2012) |
| KR (1) | KR860001853B1 (en, 2012) |
| AU (1) | AU545471B2 (en, 2012) |
| BR (1) | BR8105591A (en, 2012) |
| CA (1) | CA1184202A (en, 2012) |
| DD (1) | DD202283A5 (en, 2012) |
| DE (1) | DE3176145D1 (en, 2012) |
| GB (1) | GB2083032B (en, 2012) |
| IN (1) | IN154274B (en, 2012) |
| MY (1) | MY8500871A (en, 2012) |
| SG (1) | SG72984G (en, 2012) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5004845A (en) * | 1981-08-20 | 1991-04-02 | Davy Mckee (London) Limited | Hydrogenation of aldehydes |
| DE4307193A1 (de) * | 1993-03-08 | 1994-09-15 | Bayer Ag | Verfahren zur Herstellung von C¶1¶-C¶4¶-Alkyl-nitriten |
| CN100343219C (zh) * | 2003-07-17 | 2007-10-17 | 上海焦化有限公司 | 一种草酸联产亚硝酸钠的方法和装置 |
| BRPI0913770B1 (pt) * | 2008-12-18 | 2017-09-12 | China Petroleum & Chemical Corporation | Process for the production of ethylene glycol from an oxalate |
| CN101544539B (zh) * | 2009-04-28 | 2011-11-16 | 华烁科技股份有限公司 | 一种生产聚合级乙二醇并联产乙醇酸甲酯的方法 |
| CN102898304B (zh) * | 2012-10-30 | 2014-09-10 | 安徽淮化股份有限公司 | 合成气制乙二醇过程中草酸二甲酯的回收方法 |
| JP6048135B2 (ja) * | 2012-12-28 | 2016-12-21 | 宇部興産株式会社 | シュウ酸ジアルキルの製造方法 |
| US9458022B2 (en) * | 2014-03-28 | 2016-10-04 | L'Air Liquide Société Anonyme Pour L'Étude Et L'Exploitation Des Procedes Georges Claude | Process and apparatus for separating NO2 from a CO2 and NO2—containing fluid |
| US10086364B2 (en) | 2014-06-26 | 2018-10-02 | University Of Wyoming | Methods of catalytic hydrogenation for ethylene glycol formation |
| US10800987B2 (en) | 2014-06-27 | 2020-10-13 | University Of Wyoming | Composite iron-sodium catalyst for coal gasification |
| CN105218306B (zh) * | 2014-07-03 | 2019-07-09 | 中国石油化工股份有限公司 | 煤基合成气制乙二醇过程中甲醇回收方法 |
| CN104262152A (zh) * | 2014-09-16 | 2015-01-07 | 上海华谊（集团）公司 | 一种生产乙醇酸甲酯的方法 |
| WO2017017074A1 (de) | 2015-07-29 | 2017-02-02 | Basf Se | Verfahren zur herstellung von monoethylenglykol |
| WO2017125610A1 (en) | 2016-01-22 | 2017-07-27 | Avantium Knowledge Centre B.V. | Process and system |
| US10570081B2 (en) | 2017-08-02 | 2020-02-25 | Eastman Chemical Company | Process for making formic acid utilizing lower-boiling formate esters |
| US10266466B2 (en) | 2017-08-02 | 2019-04-23 | Eastman Chemical Company | Iron-catalyzed transfer hydrogenation of esters to alcohols |
| US10544077B2 (en) | 2017-08-02 | 2020-01-28 | Eastman Chemical Company | Process for making formic acid utilizing higher-boiling formate esters |
| US10266467B2 (en) | 2017-08-02 | 2019-04-23 | Eastman Chemical Company | Synthesis of glycols via transfer hydrogenation of alpha-functional esters with alcohols |
| US10435349B2 (en) | 2017-08-02 | 2019-10-08 | Eastman Chemical Company | Iron-catalyzed cross-coupling of methanol with secondary or tertiary alcohols to produce formate esters |
| CN109482107B (zh) * | 2018-11-30 | 2021-06-25 | 华东理工大学 | 草酸二甲酯的汽化方法和汽化装置 |
| CN112479822A (zh) * | 2020-11-30 | 2021-03-12 | 南京延长反应技术研究院有限公司 | 一种草酸酯法制备乙二醇的强化微界面反应系统及方法 |
| CN114653170A (zh) * | 2020-12-22 | 2022-06-24 | 中国石油化工股份有限公司 | 尾气吸收塔安全运行的方法、装置及其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2060880A (en) * | 1933-09-23 | 1936-11-17 | Du Pont | Process of producing ethylene glycol |
| US2258444A (en) * | 1939-11-24 | 1941-10-07 | Du Pont | Recovery process |
| DE1156775B (de) * | 1961-10-04 | 1963-11-07 | Knapsack Ag | Verfahren zur kontinuierlichen Herstellung von Estern der salpetrigen Saeure |
| US3878055A (en) * | 1970-06-04 | 1975-04-15 | Ppg Industries Inc | Reclamation of spent glycol by distillation in the presence of a catalytic amount of alkali metal hydroxide |
| US4087470A (en) * | 1976-06-23 | 1978-05-02 | Chevron Research Company | Process for the production of ethylene glycol |
| US4113662A (en) * | 1976-08-05 | 1978-09-12 | Chevron Research Company | Catalyst for ester hydrogenation |
| US4112245A (en) * | 1976-08-18 | 1978-09-05 | Atlantic Richfield Company | Process for the preparation of ethylene glycol |
| BE864567A (fr) * | 1977-04-25 | 1978-07-03 | Chevron Res | Procede d'hydrogenation d'esters en acools |
| GB2003872B (en) * | 1977-09-07 | 1982-05-19 | Ube Industries | Process for preparing a diester of oxalic acid |
| JPS54100312A (en) * | 1978-01-25 | 1979-08-08 | Ube Ind Ltd | Preparation of oxalic diesters |
| IT1099070B (it) * | 1978-09-14 | 1985-09-18 | Montedison Spa | Processo per la idrogenazione catalitica degli esteri ossalici |
| FR2449073A1 (fr) * | 1979-02-16 | 1980-09-12 | Rhone Poulenc Ind | Procede de recuperation de methanol et de glycol a partir de residus issus de la fabrication du polyterephtalate d'ethyleneglycol et de ses intermediaires |
-
1981
- 1981-08-10 IN IN885/CAL/81A patent/IN154274B/en unknown
- 1981-08-14 AU AU74087/81A patent/AU545471B2/en not_active Ceased
- 1981-08-21 GB GB8125655A patent/GB2083032B/en not_active Expired
- 1981-08-26 EP EP81106636A patent/EP0046983B1/en not_active Expired
- 1981-08-26 DE DE8181106636T patent/DE3176145D1/de not_active Expired
- 1981-08-31 DD DD81232902A patent/DD202283A5/de unknown
- 1981-09-01 BR BR8105591A patent/BR8105591A/pt unknown
- 1981-09-01 CA CA000384966A patent/CA1184202A/en not_active Expired
- 1981-09-02 KR KR1019810003271A patent/KR860001853B1/ko not_active Expired
-
1983
- 1983-01-19 US US06/459,424 patent/US4453026A/en not_active Expired - Lifetime
-
1984
- 1984-10-17 SG SG729/84A patent/SG72984G/en unknown
-
1985
- 1985-12-30 MY MY871/85A patent/MY8500871A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY8500871A (en) | 1985-12-31 |
| AU545471B2 (en) | 1985-07-18 |
| US4453026A (en) | 1984-06-05 |
| EP0046983B1 (en) | 1987-04-29 |
| BR8105591A (pt) | 1982-05-18 |
| KR860001853B1 (ko) | 1986-10-24 |
| EP0046983A1 (en) | 1982-03-10 |
| DE3176145D1 (en) | 1987-06-04 |
| CA1184202A (en) | 1985-03-19 |
| KR830007482A (ko) | 1983-10-21 |
| GB2083032A (en) | 1982-03-17 |
| GB2083032B (en) | 1984-08-15 |
| IN154274B (en, 2012) | 1984-10-13 |
| AU7408781A (en) | 1982-03-11 |
| SG72984G (en) | 1985-04-04 |
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