TW201509879A - 藉由絕熱硝化作用製備硝苯之方法 - Google Patents
藉由絕熱硝化作用製備硝苯之方法 Download PDFInfo
- Publication number
- TW201509879A TW201509879A TW103114920A TW103114920A TW201509879A TW 201509879 A TW201509879 A TW 201509879A TW 103114920 A TW103114920 A TW 103114920A TW 103114920 A TW103114920 A TW 103114920A TW 201509879 A TW201509879 A TW 201509879A
- Authority
- TW
- Taiwan
- Prior art keywords
- sulfuric acid
- acid
- benzene
- oxidizing agent
- phase
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000006396 nitration reaction Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 16
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 title abstract description 8
- 230000008569 process Effects 0.000 title abstract description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 172
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 141
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 51
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 51
- 239000007800 oxidant agent Substances 0.000 claims abstract description 30
- 239000008346 aqueous phase Substances 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 238000005191 phase separation Methods 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims description 15
- 229960001597 nifedipine Drugs 0.000 claims description 15
- 239000012074 organic phase Substances 0.000 claims description 12
- 239000012071 phase Substances 0.000 claims description 11
- 238000003860 storage Methods 0.000 claims description 11
- 238000001704 evaporation Methods 0.000 claims description 7
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 6
- ILXYDRFJSVKZLV-UHFFFAOYSA-N oxosulfamic acid Chemical compound OS(=O)(=O)N=O ILXYDRFJSVKZLV-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 description 24
- 239000002253 acid Substances 0.000 description 15
- 229910002651 NO3 Inorganic materials 0.000 description 12
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000001117 sulphuric acid Substances 0.000 description 9
- 235000011149 sulphuric acid Nutrition 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 229910021645 metal ion Inorganic materials 0.000 description 5
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000007689 inspection Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MZNYWPRCVDMOJG-UHFFFAOYSA-N N-(1-naphthyl)ethylenediamine dihydrochloride Chemical compound [Cl-].[Cl-].C1=CC=C2C([NH2+]CC[NH3+])=CC=CC2=C1 MZNYWPRCVDMOJG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000005554 pickling Methods 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
- 230000008092 positive effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 229950002929 trinitrophenol Drugs 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- ZXQHSPWBYMLHLB-BXTVWIJMSA-M 6-ethoxy-1-methyl-2-[(e)-2-(3-nitrophenyl)ethenyl]quinolin-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC2=CC(OCC)=CC=C2[N+](C)=C1\C=C\C1=CC=CC([N+]([O-])=O)=C1 ZXQHSPWBYMLHLB-BXTVWIJMSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000001546 nitrifying effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
Classifications
-
- 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
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- 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
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13165822 | 2013-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201509879A true TW201509879A (zh) | 2015-03-16 |
Family
ID=48236692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW103114920A TW201509879A (zh) | 2013-04-29 | 2014-04-25 | 藉由絕熱硝化作用製備硝苯之方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9302978B1 (enExample) |
| EP (1) | EP2991966B1 (enExample) |
| JP (1) | JP6458006B2 (enExample) |
| KR (1) | KR20160003084A (enExample) |
| CN (1) | CN105308018B (enExample) |
| PT (1) | PT2991966T (enExample) |
| SA (1) | SA515370062B1 (enExample) |
| TW (1) | TW201509879A (enExample) |
| WO (1) | WO2014177450A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102597388B1 (ko) * | 2017-03-07 | 2023-11-03 | 코베스트로 도이칠란트 아게 | 니트로벤젠의 제조 방법 |
| CN112939781B (zh) * | 2019-12-11 | 2022-07-12 | 万华化学（宁波）有限公司 | 一种通过苯的硝化制备硝基苯的连续运行的绝热方法 |
| CN116457333A (zh) * | 2020-11-11 | 2023-07-18 | 巴斯夫欧洲公司 | 浓缩稀硫酸的方法 |
| EP4547642A1 (en) | 2022-06-28 | 2025-05-07 | Basf Se | Process for producing nitrobenzene |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2256999A (en) | 1939-03-08 | 1941-09-23 | Du Pont | Nitration of organic compounds |
| JPS6038407B2 (ja) * | 1974-12-27 | 1985-08-31 | 鐘淵化学工業株式会社 | 塩化ビニルの懸濁重合法 |
| US4091042A (en) * | 1977-08-19 | 1978-05-23 | American Cyanamid Company | Continuous adiabatic process for the mononitration of benzene |
| DE3409117A1 (de) | 1984-03-13 | 1985-09-19 | Sanpack-Gesellschaft Greiner & Co (GmbH & Co), 2000 Hamburg | Verfahren zum verpacken von verpackungsgut in bahnfoermige streckfolie |
| US5313009A (en) | 1990-01-04 | 1994-05-17 | Nrm International Technologies C.V. | Nitration process |
| JP3214165B2 (ja) * | 1993-06-30 | 2001-10-02 | 住友化学工業株式会社 | ニトロベンゼンの製造方法 |
| DE4437047A1 (de) | 1994-10-17 | 1996-04-18 | Bayer Ag | Verfahren zur Dinitrierung von aromatischen Verbindungen |
| DE19539205A1 (de) | 1995-10-22 | 1997-04-24 | Meissner Gmbh & Co Kg Josef | Verfahren zur Aromatennitrierung |
| JPH10202213A (ja) * | 1997-01-27 | 1998-08-04 | Chiyoda Corp | 配管のスケーリング防止方法 |
| US6288289B1 (en) | 2000-01-27 | 2001-09-11 | Noram Engineering And Constructors Ltd. | Integrated effluent treatment process for nitroaromatic manufacture |
| ATE555846T1 (de) | 2000-03-02 | 2012-05-15 | Dow Global Technologies Llc | Rohrreaktor, verfahren zur durchführung von flüssig-flüssig mehrphasenreaktionen und verfahren zur ring-nitrierung von aromatischen verbindungen |
| EP1291078A3 (de) | 2001-09-10 | 2004-01-28 | Bayer Ag | Rohrreaktor zur adiabatischen Nitrierung |
| DE102004017628A1 (de) | 2004-04-10 | 2005-11-03 | Bayer Materialscience Ag | Verfahren zur Aufarbeitung von aromatische Nitroverbindungen enthaltenden Abwässern |
| CN100522922C (zh) * | 2006-03-06 | 2009-08-05 | 北京夏一催化技术有限公司 | 一种硝酸硝化苯生产一硝基苯的方法 |
| DE102007059513A1 (de) * | 2007-12-11 | 2009-06-18 | Bayer Materialscience Ag | Verfahren zur Herstellung von Nitrobenzol durch adiabate Nitrierung |
| DE102008048713A1 (de) | 2008-09-24 | 2010-03-25 | Bayer Materialscience Ag | Verfahren zur kontinuierlichen Herstellung von Nitrobenzol |
| DE102010006984A1 (de) | 2010-02-05 | 2011-08-11 | Bayer MaterialScience AG, 51373 | Verfahren zur kontinuierlichen Herstellung von Nitrobenzol |
| DE102010038519A1 (de) * | 2010-07-28 | 2012-02-02 | Bayer Materialscience Ag | Verfahren zur Herstellung von Nitrobenzol durch adiabate Nitrierung |
| WO2012013678A2 (de) | 2010-07-30 | 2012-02-02 | Bayer Materialscience Ag | Verfahren zur kontinuierlichen herstellung von nitrobenzol |
| DE102011081898A1 (de) * | 2011-08-31 | 2013-02-28 | Bayer Materialscience Aktiengesellschaft | Verfahren zur kontinuierlichen Herstellung von Nitrobenzol |
-
2014
- 2014-04-24 WO PCT/EP2014/058345 patent/WO2014177450A1/de not_active Ceased
- 2014-04-24 CN CN201480024253.0A patent/CN105308018B/zh active Active
- 2014-04-24 EP EP14719020.1A patent/EP2991966B1/de active Active
- 2014-04-24 US US14/785,763 patent/US9302978B1/en active Active
- 2014-04-24 JP JP2016511011A patent/JP6458006B2/ja not_active Expired - Fee Related
- 2014-04-24 PT PT147190201T patent/PT2991966T/pt unknown
- 2014-04-24 KR KR1020157033540A patent/KR20160003084A/ko not_active Withdrawn
- 2014-04-25 TW TW103114920A patent/TW201509879A/zh unknown
-
2015
- 2015-10-27 SA SA515370062A patent/SA515370062B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2991966B1 (de) | 2017-07-12 |
| SA515370062B1 (ar) | 2016-08-02 |
| PT2991966T (pt) | 2017-10-06 |
| CN105308018B (zh) | 2017-10-03 |
| JP6458006B2 (ja) | 2019-01-23 |
| JP2016520575A (ja) | 2016-07-14 |
| CN105308018A (zh) | 2016-02-03 |
| EP2991966A1 (de) | 2016-03-09 |
| WO2014177450A1 (de) | 2014-11-06 |
| KR20160003084A (ko) | 2016-01-08 |
| US9302978B1 (en) | 2016-04-05 |
| US20160083332A1 (en) | 2016-03-24 |
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