CA2896290C - Methode de production d'oxalate de dimethyl - Google Patents
Methode de production d'oxalate de dimethyl Download PDFInfo
- Publication number
- CA2896290C CA2896290C CA2896290A CA2896290A CA2896290C CA 2896290 C CA2896290 C CA 2896290C CA 2896290 A CA2896290 A CA 2896290A CA 2896290 A CA2896290 A CA 2896290A CA 2896290 C CA2896290 C CA 2896290C
- Authority
- CA
- Canada
- Prior art keywords
- dimethyl oxalate
- column
- dimethyl
- separation column
- methanol
- 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.)
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- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 title claims abstract description 262
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 342
- 238000000926 separation method Methods 0.000 claims abstract description 142
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims abstract description 88
- 238000005859 coupling reaction Methods 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 57
- 230000008878 coupling Effects 0.000 claims abstract description 46
- 238000010168 coupling process Methods 0.000 claims abstract description 46
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 239000000047 product Substances 0.000 claims abstract description 38
- BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 claims abstract description 32
- 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
- 239000000463 material Substances 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 239000006227 byproduct Substances 0.000 claims abstract description 11
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims description 72
- 239000012071 phase Substances 0.000 claims description 56
- 238000000605 extraction Methods 0.000 claims description 35
- 239000003795 chemical substances by application Substances 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 28
- 238000007670 refining Methods 0.000 claims description 25
- 239000000945 filler Substances 0.000 claims description 22
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000007791 liquid phase Substances 0.000 claims description 14
- 238000005406 washing Methods 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 10
- 238000005265 energy consumption Methods 0.000 abstract description 13
- 239000007788 liquid Substances 0.000 description 24
- 239000007789 gas Substances 0.000 description 19
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 14
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000006096 absorbing agent Substances 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 229960003753 nitric oxide Drugs 0.000 description 9
- 238000005886 esterification reaction Methods 0.000 description 8
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 230000032050 esterification Effects 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000008929 regeneration Effects 0.000 description 5
- 238000011069 regeneration method Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000000895 extractive distillation Methods 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 2
- FXCHTIPBYHYUOH-UHFFFAOYSA-N carbonic acid;dimethyl oxalate Chemical compound OC(O)=O.COC(=O)C(=O)OC FXCHTIPBYHYUOH-UHFFFAOYSA-N 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- VVIAGPKUTFNRDU-STQMWFEESA-N (6S)-5-formyltetrahydrofolic acid Chemical compound C([C@H]1CNC=2N=C(NC(=O)C=2N1C=O)N)NC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-STQMWFEESA-N 0.000 description 1
- QQZWEECEMNQSTG-UHFFFAOYSA-N Ethyl nitrite Chemical compound CCON=O QQZWEECEMNQSTG-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
-
- 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
-
- 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
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Il est décrit une méthode de production doxalate de diméthyle, comprenant les étapes suivantes consistant à : étape a) placer, dans un réacteur de couplage, une substance réactionnelle contenant du monoxyde de carbone et du nitrite de méthyle, qui réagit en présence dun catalyseur métallique du groupe du platine, pour obtenir un flux en phase gazeuse contenant de loxalate de diméthyle; et étape b) envoyer le flux en phase gazeuse contenant de loxalate de diméthyle dans une colonne de chromatographie doxalate de diméthyle, et permettre un contact à contre-courant du flux de phase gazeuse contenant de loxalate de diméthyle avec un flux contenant du méthanol qui entre dans la colonne de chromatographie depuis sa partie supérieure, de façon à obtenir du méthanol brut depuis la partie supérieure de la colonne et un produit doxalate de diméthyle à partir de la partie inférieure de la colonne, dans laquelle le flux en phase gazeuse contenant de loxalate de diméthyle nest pas refroidi avant dêtre alimenté dans la colonne de chromatographie doxalate de diméthyle. Il est également décrit une méthode servant à produire de loxalate de diméthyle et du carbonate de diméthyle comme sous-produits. Ces méthodes se caractérisent par la simplicité des étapes du procédé, une faible consommation énergétique, un rendement élevé en oxalate de diméthyle, etc.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410314462.0A CN105330542A (zh) | 2014-07-03 | 2014-07-03 | 草酸二甲酯的生产方法 |
| CN201410314462.0 | 2014-07-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2896290A1 CA2896290A1 (fr) | 2016-01-03 |
| CA2896290C true CA2896290C (fr) | 2022-08-16 |
Family
ID=55027883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2896290A Active CA2896290C (fr) | 2014-07-03 | 2015-07-03 | Methode de production d'oxalate de dimethyl |
Country Status (5)
| Country | Link |
|---|---|
| CN (1) | CN105330542A (fr) |
| AU (1) | AU2015203732B2 (fr) |
| BR (1) | BR102015016125B8 (fr) |
| CA (1) | CA2896290C (fr) |
| RU (1) | RU2692099C2 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107954830A (zh) * | 2016-10-17 | 2018-04-24 | 上海浦景化工技术股份有限公司 | 一种降低草酸二甲酯加氢制乙二醇中产物分离能耗的方法 |
| CN106693431A (zh) * | 2017-03-17 | 2017-05-24 | 河南中托力合化学有限公司 | 新型庚烷精密分馏装置 |
| CN107362563A (zh) * | 2017-08-22 | 2017-11-21 | 南通泰利达化工有限公司 | 一种硝化棉的乙醇蒸馏工艺及装置 |
| CN109096049A (zh) * | 2018-07-03 | 2018-12-28 | 沈阳化工大学 | 一种酯化反应消除二甲酯中草酸并得到聚酯级乙二醇的方法 |
| CN111454151B (zh) * | 2020-04-26 | 2023-04-14 | 宁波中科远东催化工程技术有限公司 | 一种草酸二甲酯汽化的方法 |
| CN112174821B (zh) * | 2020-09-04 | 2023-08-18 | 中盐安徽红四方股份有限公司 | 草酸二甲酯的精馏方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1078033B (it) * | 1977-04-07 | 1985-05-08 | Snam Progetti | Processo per la preparazione di esteri dell'acido ossalico |
| US5534648A (en) * | 1993-11-30 | 1996-07-09 | Ube Industries, Ltd. | Process for continuously producing dimethyl carbonate |
| CN102911046A (zh) * | 2011-08-02 | 2013-02-06 | 中国石油化工股份有限公司 | Co偶联合成草酸二甲酯的过程中草酸二甲酯的提纯方法 |
| CN202968431U (zh) * | 2012-11-01 | 2013-06-05 | 安徽淮化股份有限公司 | 一种乙二醇工业生产分离中间产物草酸二甲酯和甲醇的复合塔器 |
| CN103483150B (zh) * | 2013-08-31 | 2016-02-17 | 安徽淮化股份有限公司 | 一种以煤为原料生产合成乙二醇的方法和装置 |
-
2014
- 2014-07-03 CN CN201410314462.0A patent/CN105330542A/zh active Pending
-
2015
- 2015-07-03 CA CA2896290A patent/CA2896290C/fr active Active
- 2015-07-03 RU RU2015126664A patent/RU2692099C2/ru active
- 2015-07-03 AU AU2015203732A patent/AU2015203732B2/en active Active
- 2015-07-03 BR BR102015016125A patent/BR102015016125B8/pt active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| CA2896290A1 (fr) | 2016-01-03 |
| BR102015016125A2 (pt) | 2018-06-12 |
| RU2015126664A3 (fr) | 2019-01-31 |
| BR102015016125B8 (pt) | 2021-05-18 |
| BR102015016125B1 (pt) | 2020-12-08 |
| CN105330542A (zh) | 2016-02-17 |
| RU2015126664A (ru) | 2017-01-12 |
| AU2015203732A1 (en) | 2016-01-21 |
| AU2015203732B2 (en) | 2019-04-04 |
| RU2692099C2 (ru) | 2019-06-21 |
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