DD201774A5 - Verfahren zur kontinuierlichen herstellung eines oxalsaeurediesters - Google Patents
Verfahren zur kontinuierlichen herstellung eines oxalsaeurediesters Download PDFInfo
- Publication number
- DD201774A5 DD201774A5 DD81232784A DD23278481A DD201774A5 DD 201774 A5 DD201774 A5 DD 201774A5 DD 81232784 A DD81232784 A DD 81232784A DD 23278481 A DD23278481 A DD 23278481A DD 201774 A5 DD201774 A5 DD 201774A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- gas
- stage
- alcohol
- volume
- item
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000010924 continuous production Methods 0.000 title abstract description 5
- 239000002253 acid Substances 0.000 title 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 title 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 102
- 239000007789 gas Substances 0.000 claims abstract description 96
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 50
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 47
- 230000008929 regeneration Effects 0.000 claims abstract description 40
- 238000011069 regeneration method Methods 0.000 claims abstract description 40
- -1 oxalic acid diester Chemical class 0.000 claims abstract description 28
- 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 26
- 235000006408 oxalic acid Nutrition 0.000 claims abstract description 22
- 239000007788 liquid Substances 0.000 claims abstract description 17
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 7
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 238000006555 catalytic reaction Methods 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 9
- 239000011949 solid catalyst Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 229960003753 nitric oxide Drugs 0.000 description 41
- 239000000203 mixture Substances 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 23
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 11
- BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 description 11
- 239000001569 carbon dioxide Substances 0.000 description 10
- 229910002092 carbon dioxide Inorganic materials 0.000 description 10
- 239000007858 starting material Substances 0.000 description 9
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 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
- 230000000052 comparative effect Effects 0.000 description 7
- QQZWEECEMNQSTG-UHFFFAOYSA-N Ethyl nitrite Chemical compound CCON=O QQZWEECEMNQSTG-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 230000001172 regenerating effect Effects 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 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
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004650 carbonic acid diesters Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 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
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 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
- 239000000463 material 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
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000002808 molecular sieve Substances 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
- 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
- KAOQVXHBVNKNHA-UHFFFAOYSA-N propyl nitrite Chemical compound CCCON=O KAOQVXHBVNKNHA-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 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
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/36—Oxalic acid esters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55116456A JPS5742654A (en) | 1980-08-26 | 1980-08-26 | Preparation of dimethyl oxalate |
| JP55116458A JPS5742655A (en) | 1980-08-26 | 1980-08-26 | Continuous preparation of oxalic acid diester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD201774A5 true DD201774A5 (de) | 1983-08-10 |
Family
ID=26454786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81232784A DD201774A5 (de) | 1980-08-26 | 1981-08-25 | Verfahren zur kontinuierlichen herstellung eines oxalsaeurediesters |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4461909A (xx) |
| EP (1) | EP0046598B1 (xx) |
| KR (1) | KR850001627B1 (xx) |
| AR (1) | AR229099A1 (xx) |
| AU (1) | AU545415B2 (xx) |
| BR (1) | BR8105423A (xx) |
| CA (1) | CA1160249A (xx) |
| DD (1) | DD201774A5 (xx) |
| DE (1) | DE3168316D1 (xx) |
| GB (1) | GB2082582B (xx) |
| MY (1) | MY8500870A (xx) |
| SG (1) | SG72884G (xx) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG71167A1 (en) | 1997-10-21 | 2000-03-21 | Ube Industries | Process for producing alkyl nitrite |
| CN101492370B (zh) * | 2008-12-18 | 2012-07-25 | 中国石油化工股份有限公司 | Co偶联制草酸酯的方法 |
| CN101993366B (zh) * | 2009-08-31 | 2014-01-22 | 中国石油化工股份有限公司 | 由co气相法制备草酸酯的方法 |
| CN101993365B (zh) * | 2009-08-31 | 2013-03-06 | 中国石油化工股份有限公司 | Co偶联生产草酸酯的方法 |
| CN102219680B (zh) * | 2010-04-15 | 2013-09-18 | 中国石油化工股份有限公司 | 由co气相法制备草酸酯的方法 |
| CN102219676B (zh) * | 2010-04-15 | 2013-09-18 | 中国石油化工股份有限公司 | Co偶联制草酸酯的方法 |
| CN102219682A (zh) * | 2010-04-15 | 2011-10-19 | 中国石油化工股份有限公司 | Co偶联制备草酸酯的方法 |
| CN102219675B (zh) * | 2010-04-15 | 2013-08-14 | 中国石油化工股份有限公司 | Co偶联生产草酸酯的方法 |
| CN102219679B (zh) * | 2010-04-15 | 2013-12-04 | 中国石油化工股份有限公司 | Co气相偶联生产草酸酯的方法 |
| CN102219678B (zh) * | 2010-04-15 | 2013-08-14 | 中国石油化工股份有限公司 | Co制草酸酯的开车方法 |
| CN102219677A (zh) * | 2010-04-15 | 2011-10-19 | 中国石油化工股份有限公司 | 由co偶联生产草酸酯的方法 |
| CN102276459B (zh) | 2010-06-11 | 2013-12-18 | 中国石油化工股份有限公司 | 采用co气相法制备草酸酯的方法 |
| CN102276457B (zh) * | 2010-06-11 | 2014-03-05 | 中国石油化工股份有限公司 | 由co气相法制备草酸酯的方法 |
| CN102649733B (zh) * | 2011-02-25 | 2015-01-07 | 中国石油化工股份有限公司 | Co气体气相催化偶联制草酸酯的方法 |
| CN105536815A (zh) * | 2015-12-10 | 2016-05-04 | 大连瑞克科技有限公司 | 一种用于亚硝酸甲酯制备草酸二甲酯的催化剂及制备方法 |
| CN106892819B (zh) * | 2017-02-20 | 2019-06-21 | 宁波中科远东催化工程技术有限公司 | 一种co合成草酸二甲酯的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2003872B (en) * | 1977-09-07 | 1982-05-19 | Ube Industries | Process for preparing a diester of oxalic acid |
| JPS5441813A (en) * | 1977-09-07 | 1979-04-03 | Ube Ind Ltd | Preparation of oxalic acid diesters |
| JPS54100312A (en) * | 1978-01-25 | 1979-08-08 | Ube Ind Ltd | Preparation of oxalic diesters |
| IT1097268B (it) * | 1978-06-23 | 1985-08-31 | Montedison Spa | Processo per la preparazione di esteri dell'acido ossalico |
-
1981
- 1981-08-12 AU AU74014/81A patent/AU545415B2/en not_active Ceased
- 1981-08-14 KR KR1019810002952A patent/KR850001627B1/ko active
- 1981-08-20 AR AR286492A patent/AR229099A1/es active
- 1981-08-21 GB GB8125656A patent/GB2082582B/en not_active Expired
- 1981-08-25 CA CA000384581A patent/CA1160249A/en not_active Expired
- 1981-08-25 BR BR8105423A patent/BR8105423A/pt unknown
- 1981-08-25 DD DD81232784A patent/DD201774A5/de unknown
- 1981-08-26 DE DE8181106637T patent/DE3168316D1/de not_active Expired
- 1981-08-26 EP EP81106637A patent/EP0046598B1/en not_active Expired
-
1983
- 1983-05-19 US US06/495,459 patent/US4461909A/en not_active Expired - Lifetime
-
1984
- 1984-10-17 SG SG728/84A patent/SG72884G/en unknown
-
1985
- 1985-12-30 MY MY870/85A patent/MY8500870A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2082582B (en) | 1984-05-23 |
| EP0046598A1 (en) | 1982-03-03 |
| MY8500870A (en) | 1985-12-31 |
| DE3168316D1 (en) | 1985-02-28 |
| AU545415B2 (en) | 1985-07-11 |
| GB2082582A (en) | 1982-03-10 |
| EP0046598B1 (en) | 1985-01-16 |
| SG72884G (en) | 1985-04-04 |
| KR830006162A (ko) | 1983-09-17 |
| US4461909A (en) | 1984-07-24 |
| KR850001627B1 (ko) | 1985-10-31 |
| AR229099A1 (es) | 1983-06-15 |
| AU7401481A (en) | 1982-03-04 |
| BR8105423A (pt) | 1982-05-11 |
| CA1160249A (en) | 1984-01-10 |
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