JP2011173880A - ニトロベンゼンを連続的に製造する方法 - Google Patents
ニトロベンゼンを連続的に製造する方法 Download PDFInfo
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- JP2011173880A JP2011173880A JP2011022835A JP2011022835A JP2011173880A JP 2011173880 A JP2011173880 A JP 2011173880A JP 2011022835 A JP2011022835 A JP 2011022835A JP 2011022835 A JP2011022835 A JP 2011022835A JP 2011173880 A JP2011173880 A JP 2011173880A
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- reactor
- benzene
- pressure
- mixed acid
- acid
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- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 183
- 239000002253 acid Substances 0.000 claims abstract description 78
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 238000006396 nitration reaction Methods 0.000 claims abstract description 28
- 238000005191 phase separation Methods 0.000 claims abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 38
- 230000008569 process Effects 0.000 claims description 27
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 26
- 229910017604 nitric acid Inorganic materials 0.000 claims description 26
- 239000006185 dispersion Substances 0.000 claims description 15
- 239000000376 reactant Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 230000007423 decrease Effects 0.000 claims description 4
- 238000011144 upstream manufacturing Methods 0.000 abstract description 16
- 150000001491 aromatic compounds Chemical class 0.000 abstract description 6
- 239000002699 waste material Substances 0.000 abstract description 6
- 230000000802 nitrating effect Effects 0.000 abstract description 5
- 239000012808 vapor phase Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 31
- 229910000831 Steel Inorganic materials 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 239000010959 steel Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 230000003068 static effect Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 210000003298 dental enamel Anatomy 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 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
- 239000007791 liquid phase Substances 0.000 description 4
- 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 4
- 229910052715 tantalum Inorganic materials 0.000 description 4
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 4
- 229950002929 trinitrophenol Drugs 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229910000851 Alloy steel Inorganic materials 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 nitronium ions Chemical class 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000005406 washing 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
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
【解決手段】ニトロ化反応器の上流側の圧力が、粗製ニトロベンゼン及び廃酸を分離するのに使用される相分離装置の気相中の圧力を14bar〜40bar上回るように設定し、断熱条件下で、ベンゼンを混酸で連続的にニトロ化してニトロベンゼンを製造する。
【選択図】なし
Description
STY[tニトロベンゼン/(m3 反応空間・h)] =
生産される量[tニトロベンゼン/h]/反応空間[m3]。
以下の例を、次の条件下で実施した:
全ての試験を、455mlの内容積を有するエナメル被覆された鋼の管形反応器中で実施した。前記管形反応器を垂直に取り付け、かつ流れは底部からであった。前記管形反応器はタンタル製の10の分散要素を含有し、それらは頂部から底部へ減少する圧力損失を示した。混酸中でゆきわたる圧力(p1a)は、隔膜圧力計を用いて前記管形反応器の上流側で測定されてから、ベンゼンを、低圧損ランスを用いて前記混酸中へ導入し、かつ生じる流れを前記反応器中へ導入した。本試験配置において、p1aは、前記反応器へ入る際にベンゼン及び混酸を接触させることにより得られるプロセス生成物の圧力p1と同一視されることができる。前記硫酸は常に71%質量%の濃度を有しており、かつ前記硝酸は常に69.2%質量%の濃度を有していた。前記混酸は常に96℃の温度を有しており、かつ前記ベンゼンは予熱され、かつ常に80℃の温度を有していた。前記ベンゼンの純度は常に99%質量%よりも多かった。前記反応器を通過した後に、粗製反応生成物を、加圧せずに操作される静的相分離装置中へ導入した。
Claims (5)
- 硫酸と硝酸を含んでなる混酸でベンゼンを断熱ニトロ化することによりニトロベンゼンを製造する方法であって、前記方法が、
(i)前記ベンゼン及び前記混酸を、
a)別個に、その際に前記ベンゼン又は前記混酸の少なくとも1つは、前記反応器へ入る際に圧力p1の状態であり、
又は
b)互いに接触された後に一緒に、前記反応器へ入る際に圧力p1下で
のいずれかで、前記反応器中へ導入し、
(ii)前記ベンゼン及び前記混酸を、1〜30の分散要素を有する前記反応器中で互いに分散させ、但し、1よりも多い分散要素が存在する場合には、前記分散要素は前後して配置されており、
(iii)前記反応器から反応生成物を除去し、
(iv)(iii)において除去された反応生成物を、気相圧力p2がゆきわたる相分離装置中の相分離にかけ、
ここで、
p1−p2 = 14bar〜40bar
を特徴とする、ニトロベンゼンを製造する方法。 - 硝酸の少なくとも99%転化後の反応器温度から、ニトロ化反応の出発前の組み合わされたベンゼン及び混酸反応物の温度を引くと、25K〜60Kである、請求項1記載の方法。
- 2〜20の分散要素が(ii)において使用される、請求項1記載の方法。
- 各分散要素が圧力損失を示し、かつ前記分散要素の圧力損失が、前記ベンゼン及び混酸反応物の流れの方向で減少する、請求項3記載の方法。
- 前記反応物の流れの方向での第二の及び各々その後の分散要素が、前の分散要素の圧力損失の多くとも80%を示す、請求項4記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102010006984.1 | 2010-02-05 | ||
DE102010006984A DE102010006984A1 (de) | 2010-02-05 | 2010-02-05 | Verfahren zur kontinuierlichen Herstellung von Nitrobenzol |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011173880A true JP2011173880A (ja) | 2011-09-08 |
JP5791912B2 JP5791912B2 (ja) | 2015-10-07 |
Family
ID=43821881
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011022835A Expired - Fee Related JP5791912B2 (ja) | 2010-02-05 | 2011-02-04 | ニトロベンゼンを連続的に製造する方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8357827B2 (ja) |
EP (1) | EP2354117B1 (ja) |
JP (1) | JP5791912B2 (ja) |
KR (1) | KR101822193B1 (ja) |
CN (1) | CN102153476B (ja) |
DE (1) | DE102010006984A1 (ja) |
ES (1) | ES2524397T3 (ja) |
PT (1) | PT2354117E (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015522637A (ja) * | 2012-07-27 | 2015-08-06 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフトBayer MaterialScience AG | 断熱的ニトロ化によるニトロベンゼンの製造方法 |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2877442B1 (de) * | 2012-07-27 | 2016-11-16 | Covestro Deutschland AG | Verfahren zur herstellung von nitrobenzol durch adiabate nitrierung |
CN104487413B (zh) | 2012-07-27 | 2017-03-29 | 科思创德国股份有限公司 | 通过绝热硝化制备硝基苯的方法 |
WO2014177450A1 (de) | 2013-04-29 | 2014-11-06 | Bayer Materialscience Ag | Verfahren zur herstellung von nitrobenzol durch adiabate nitrierung |
CN103304421A (zh) * | 2013-06-26 | 2013-09-18 | 南京理工大学 | 发烟硫酸-硝酸体系硝化邻硝基甲苯制备二硝基甲苯的方法 |
JP6661555B2 (ja) | 2014-06-24 | 2020-03-11 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag | ニトロベンゼンの製造方法 |
DE102017110084B4 (de) | 2017-02-03 | 2019-07-04 | Josef Meissner Gmbh & Co. Kg | Verfahren und Anlage zur adiabatischen Nitrierung von Aromaten |
US10815189B2 (en) | 2017-03-07 | 2020-10-27 | Covestro Deutschland Ag | Method for producing nitrobenzene |
WO2020011817A1 (de) | 2018-07-12 | 2020-01-16 | Covestro Deutschland Ag | Verfahren zur herstellung von nitrobenzol durch adiabatisch betriebene nitrierung von benzol |
WO2020021323A1 (en) | 2018-07-24 | 2020-01-30 | Noram International Limited | Nitration reactor and method |
WO2020212334A1 (de) | 2019-04-17 | 2020-10-22 | Covestro Deutschland Ag | Verfahren und vorrichtung zur herstellung von nitrobenzol |
EP3956289A1 (de) | 2019-04-17 | 2022-02-23 | Covestro Deutschland AG | Verfahren zur kontinuierlichen herstellung von nitrobenzol |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS5432424A (en) * | 1977-08-19 | 1979-03-09 | American Cyanamid Co | Process for preparing mononitrobenzene |
JPH07258173A (ja) * | 1994-02-14 | 1995-10-09 | Bayer Ag | モノニトロトルエン類の断熱製造方法 |
JP2003160543A (ja) * | 2001-09-10 | 2003-06-03 | Bayer Ag | 断熱的ニトロ化のための管形反応器 |
JP2009143911A (ja) * | 2007-12-11 | 2009-07-02 | Bayer Materialscience Ag | 断熱的ニトロ化によるニトロベンゼンの製造法 |
Family Cites Families (11)
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US2256999A (en) | 1939-03-08 | 1941-09-23 | Du Pont | Nitration of organic compounds |
US4994242A (en) | 1988-08-15 | 1991-02-19 | Noram Engineering And Constructors Ltd. | Jet impingement reactor |
US4973770A (en) | 1988-12-15 | 1990-11-27 | C-I-L, Inc. | Manufacture of organic nitro compounds |
DE69026590T2 (de) | 1990-01-04 | 1996-10-31 | Nrm Int Tech | Nitrierungsverfahren |
TW236610B (en) * | 1992-11-13 | 1994-12-21 | Bayer Ag | Preparation of dinitrotoluene |
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 |
US5763687A (en) | 1995-12-15 | 1998-06-09 | Mitsui Chemicals, Inc. | Preparation process for aromatic mononitro compounds |
PT1272268E (pt) | 2000-03-02 | 2012-07-24 | Dow Global Technologies Llc | Reator tubular, processo de realização de reações multifásicas líquido/ líquido num reator tubular, e um processo de nitração cíclica de compostos aromáticos num reator tubular |
DE102006004943A1 (de) | 2006-02-03 | 2007-08-09 | Bayer Materialscience Ag | Verfahren zur Herstellung von Nitrobenzol |
CN101613285B (zh) * | 2008-06-25 | 2012-12-05 | 中国科学院大连化学物理研究所 | 一种硝基苯合成方法及专用装备 |
-
2010
- 2010-02-05 DE DE102010006984A patent/DE102010006984A1/de not_active Withdrawn
-
2011
- 2011-01-31 CN CN201110037401.0A patent/CN102153476B/zh active Active
- 2011-02-01 KR KR1020110010244A patent/KR101822193B1/ko active IP Right Grant
- 2011-02-02 ES ES11152982.2T patent/ES2524397T3/es active Active
- 2011-02-02 PT PT111529822T patent/PT2354117E/pt unknown
- 2011-02-02 US US13/019,350 patent/US8357827B2/en active Active
- 2011-02-02 EP EP11152982.2A patent/EP2354117B1/de active Active
- 2011-02-04 JP JP2011022835A patent/JP5791912B2/ja not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5432424A (en) * | 1977-08-19 | 1979-03-09 | American Cyanamid Co | Process for preparing mononitrobenzene |
JPH07258173A (ja) * | 1994-02-14 | 1995-10-09 | Bayer Ag | モノニトロトルエン類の断熱製造方法 |
JP2003160543A (ja) * | 2001-09-10 | 2003-06-03 | Bayer Ag | 断熱的ニトロ化のための管形反応器 |
JP2009143911A (ja) * | 2007-12-11 | 2009-07-02 | Bayer Materialscience Ag | 断熱的ニトロ化によるニトロベンゼンの製造法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015522637A (ja) * | 2012-07-27 | 2015-08-06 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフトBayer MaterialScience AG | 断熱的ニトロ化によるニトロベンゼンの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
US20110196177A1 (en) | 2011-08-11 |
JP5791912B2 (ja) | 2015-10-07 |
US8357827B2 (en) | 2013-01-22 |
KR101822193B1 (ko) | 2018-01-25 |
DE102010006984A1 (de) | 2011-08-11 |
PT2354117E (pt) | 2014-11-28 |
ES2524397T3 (es) | 2014-12-09 |
CN102153476A (zh) | 2011-08-17 |
EP2354117B1 (de) | 2014-09-24 |
CN102153476B (zh) | 2015-04-22 |
EP2354117A1 (de) | 2011-08-10 |
KR20110091480A (ko) | 2011-08-11 |
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