JP5080268B2 - Ｎ，ｎ−ジメチルアセトアミド（ｄｍａｃ）の製造方法 - Google Patents
Ｎ，ｎ−ジメチルアセトアミド（ｄｍａｃ）の製造方法 Download PDFInfo
- Publication number
- JP5080268B2 JP5080268B2 JP2007544789A JP2007544789A JP5080268B2 JP 5080268 B2 JP5080268 B2 JP 5080268B2 JP 2007544789 A JP2007544789 A JP 2007544789A JP 2007544789 A JP2007544789 A JP 2007544789A JP 5080268 B2 JP5080268 B2 JP 5080268B2
- Authority
- JP
- Japan
- Prior art keywords
- mass
- dmac
- column
- methanol
- process according
- 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.)
- Expired - Fee Related
Links
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 title claims description 55
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 129
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 26
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 22
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 17
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000006227 byproduct Substances 0.000 claims description 12
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000010626 work up procedure Methods 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- 238000001944 continuous distillation Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 238000009834 vaporization Methods 0.000 claims 1
- 230000008016 vaporization Effects 0.000 claims 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 8
- -1 carboxylic acid diol esters Chemical class 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000007098 aminolysis reaction Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QZJVWTNHFOMVHX-UHFFFAOYSA-N methanol;methyl acetate Chemical compound OC.COC(C)=O QZJVWTNHFOMVHX-UHFFFAOYSA-N 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004058886.4 | 2004-12-06 | ||
| DE102004058886A DE102004058886A1 (de) | 2004-12-06 | 2004-12-06 | Verfahren zur Herstellung von N,N-Dimethylacetamid (DMAC) |
| PCT/EP2005/012982 WO2006061159A1 (de) | 2004-12-06 | 2005-12-03 | Verfahren zur herstellung von n,n-dimethylacetamid (dmac) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008523000A JP2008523000A (ja) | 2008-07-03 |
| JP2008523000A5 JP2008523000A5 (enExample) | 2011-11-24 |
| JP5080268B2 true JP5080268B2 (ja) | 2012-11-21 |
Family
ID=35871278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007544789A Expired - Fee Related JP5080268B2 (ja) | 2004-12-06 | 2005-12-03 | Ｎ，ｎ−ジメチルアセトアミド（ｄｍａｃ）の製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US20080207949A1 (enExample) |
| EP (1) | EP1828102B1 (enExample) |
| JP (1) | JP5080268B2 (enExample) |
| CN (1) | CN101072748B (enExample) |
| DE (1) | DE102004058886A1 (enExample) |
| ES (1) | ES2472271T3 (enExample) |
| WO (1) | WO2006061159A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004058888A1 (de) | 2004-12-06 | 2006-06-08 | Basf Ag | Verfahren zur Herstellung von N,N-Dimethylacetamid (DMAC) |
| US8928336B2 (en) | 2011-06-09 | 2015-01-06 | Ford Global Technologies, Llc | Proximity switch having sensitivity control and method therefor |
| CN102993039A (zh) * | 2012-12-18 | 2013-03-27 | 常州大学 | 一种回收聚醚砜纺丝废水中二甲基乙酰胺的方法 |
| US20150329477A1 (en) * | 2012-12-19 | 2015-11-19 | Basf Se | Continuous method for separating salts in the production of dimethylacetamide |
| CN103922957B (zh) * | 2014-03-21 | 2016-05-18 | 迈奇化学股份有限公司 | 一种连续生产二乙基甲酰胺的制备方法 |
| CN110156621B (zh) * | 2019-05-08 | 2022-07-26 | 重庆建峰工业集团有限公司 | 在微通道反应器中进行液-液均相合成n,n-二甲基乙酰胺的方法 |
| CN110204454A (zh) * | 2019-06-27 | 2019-09-06 | 埃姆媞（无锡）分离技术有限公司 | 二甲基乙酰胺的回收系统及方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1406279A (fr) | 1963-10-04 | 1965-07-16 | Du Pont | Procédé de fabrication de la diméthylacétamide |
| US3300531A (en) | 1963-10-04 | 1967-01-24 | Du Pont | Process for preparing dimethylacetamide |
| GB1164534A (en) * | 1967-02-21 | 1969-09-17 | Ici Ltd | Production of Di-N-Methylamides |
| CA1073467A (en) | 1975-01-14 | 1980-03-11 | William E. Smith | Process for the production of diols and n,n-dialkyl carboxylic acid amides |
| CA1073468A (en) | 1975-01-14 | 1980-03-11 | General Electric Company | Process for the simultaneous production of diols and n,n-dialkyl carboxylic acid amides |
| SU1004357A1 (ru) | 1977-06-08 | 1983-03-15 | Днепропетровский химико-технологический институт им.Ф.Э.Дзержинского | Способ получени диметиламидов муравьиной или уксусной кислоты |
| US4189566A (en) | 1978-01-14 | 1980-02-19 | Basf Aktiengesellschaft | Polymerization of tetrahydrofuran |
| US4258200A (en) | 1980-03-11 | 1981-03-24 | Air Products And Chemicals, Inc. | Production of carboxylic acid amides and carbamates using cobalt catalysts |
| JPH02160749A (ja) | 1988-12-13 | 1990-06-20 | Lion Akzo Kk | 脂肪族カルボン酸アミド類の製造方法 |
| JPH1077255A (ja) * | 1996-09-04 | 1998-03-24 | Kao Corp | ポリオキシアルキレン脂肪酸アミドの製造方法 |
| JP3235977B2 (ja) | 1997-09-24 | 2001-12-04 | 三菱レイヨン株式会社 | ジメチルホルムアミドの製造方法 |
| DE19758296A1 (de) | 1997-12-31 | 1999-07-01 | Basf Ag | Herstellung von Polytetrahydrofuran mit endständigen Hydroxylgruppen unter Verwendung von Ionenaustauschern |
| DE19817113A1 (de) | 1998-04-17 | 1999-10-21 | Basf Ag | Herstellung von Polytetrahydrofuran mit endständigen Hydroxylgruppen durch Wechsel von kontinuierlicher und disperser Phase |
| DE10315214A1 (de) | 2003-04-03 | 2004-10-14 | Basf Ag | Verfahren zur Reinigung von Dimethylacetamid (DMAC) |
| CN1663944A (zh) * | 2004-03-06 | 2005-09-07 | 浙江江山化工股份有限公司 | 一种生产乙酰胺类化合物的方法 |
| DE102004030616A1 (de) | 2004-06-24 | 2006-01-26 | Basf Ag | Verfahren zur Reinigung von Dimethylacetamid (DMAc) |
| DE102004058888A1 (de) | 2004-12-06 | 2006-06-08 | Basf Ag | Verfahren zur Herstellung von N,N-Dimethylacetamid (DMAC) |
| DE102004058887A1 (de) | 2004-12-06 | 2006-06-08 | Basf Ag | Verfahren zur Herstellung von N,N-Dimethylacetamid (DMAC) |
-
2004
- 2004-12-06 DE DE102004058886A patent/DE102004058886A1/de not_active Withdrawn
-
2005
- 2005-12-03 EP EP05815808.0A patent/EP1828102B1/de not_active Expired - Lifetime
- 2005-12-03 CN CN2005800418295A patent/CN101072748B/zh not_active Expired - Fee Related
- 2005-12-03 JP JP2007544789A patent/JP5080268B2/ja not_active Expired - Fee Related
- 2005-12-03 US US11/720,774 patent/US20080207949A1/en not_active Abandoned
- 2005-12-03 WO PCT/EP2005/012982 patent/WO2006061159A1/de not_active Ceased
- 2005-12-03 ES ES05815808.0T patent/ES2472271T3/es not_active Expired - Lifetime
-
2010
- 2010-12-14 US US12/967,798 patent/US8338644B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006061159A1 (de) | 2006-06-15 |
| CN101072748B (zh) | 2011-03-16 |
| ES2472271T3 (es) | 2014-06-30 |
| EP1828102A1 (de) | 2007-09-05 |
| CN101072748A (zh) | 2007-11-14 |
| EP1828102B1 (de) | 2014-05-07 |
| US20080207949A1 (en) | 2008-08-28 |
| US8338644B2 (en) | 2012-12-25 |
| DE102004058886A1 (de) | 2006-06-08 |
| JP2008523000A (ja) | 2008-07-03 |
| US20110082316A1 (en) | 2011-04-07 |
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