JP5388427B2 - イソシアネートの連続的な製造方法 - Google Patents
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- JP5388427B2 JP5388427B2 JP2007167869A JP2007167869A JP5388427B2 JP 5388427 B2 JP5388427 B2 JP 5388427B2 JP 2007167869 A JP2007167869 A JP 2007167869A JP 2007167869 A JP2007167869 A JP 2007167869A JP 5388427 B2 JP5388427 B2 JP 5388427B2
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- 239000012948 isocyanate Substances 0.000 title claims abstract description 88
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 85
- 238000000034 method Methods 0.000 title claims abstract description 77
- 238000010924 continuous production Methods 0.000 title description 15
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 157
- 150000001412 amines Chemical class 0.000 claims abstract description 82
- 239000000463 material Substances 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims description 127
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 57
- -1 amine hydrochloride Chemical class 0.000 claims description 53
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 49
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 40
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 29
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 18
- 238000000926 separation method Methods 0.000 claims description 13
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 13
- 239000005056 polyisocyanate Substances 0.000 claims description 11
- 229920001228 polyisocyanate Polymers 0.000 claims description 11
- 239000012442 inert solvent Substances 0.000 claims description 10
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 description 60
- 239000002904 solvent Substances 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 37
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 33
- 238000004519 manufacturing process Methods 0.000 description 26
- 239000007791 liquid phase Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 21
- 239000007789 gas Substances 0.000 description 19
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 18
- 239000012071 phase Substances 0.000 description 18
- 238000000354 decomposition reaction Methods 0.000 description 17
- 239000000376 reactant Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 14
- 239000006227 byproduct Substances 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000013461 design Methods 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- 150000003141 primary amines Chemical class 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000003068 static effect Effects 0.000 description 6
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 5
- 229940117389 dichlorobenzene Drugs 0.000 description 5
- 238000010517 secondary reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 3
- 229920000265 Polyparaphenylene Polymers 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000001825 Polyoxyethene (8) stearate Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000001164 aluminium sulphate Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- JLVWYWVLMFVCDI-UHFFFAOYSA-N diethyl benzene-1,3-dicarboxylate Chemical compound CCOC(=O)C1=CC=CC(C(=O)OCC)=C1 JLVWYWVLMFVCDI-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 230000008642 heat stress Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000021715 photosynthesis, light harvesting Effects 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
− (1)混合チャンバと上流の分配チャンバをそれらの実質的に回転対称のケーシング中に有し;
− (2)少なくとも第一の材料を、混合チャンバの軸内において、例えば分配チャンバ壁の側方に入る曲管を介して導入することが可能であり;
− (3)少なくとも第二の材料流が、分配チャンバ中に流入することが可能であり、そして混合反応器の軸と同軸の多数の平行な孔を介して混合チャンバに至ることが可能であり;
− (4)軸を介して駆動するロータ要素とケーシングに連結されたステータ要素とを有する混合チャンバを有し;
− (5)反応混合物を撹拌槽反応器の出口管中に移送するインペラを形成しうる混合チャンバ出口を有し;かつ
− (6)それらの成分を、最適な条件下でスループットとは無関係に、外部機械駆動の手段によって混合することを可能にする
混合反応器である。
− a)ボルトが、混合チャンバの軸に対して回転対称に配置されたそれらの孔のそれぞれに割り当てられており;
− b)これらのボルトは、共通の支持リングと分配チャンバのケーシングを通して挿入された軸とによって変位させることができ;
− c)固まった堆積物及び/又は閉塞物が該孔中に形成された場合に、該孔はボルトの軸置換によって清掃することができ;かつ
− d)孔の清掃のための非生産時間をこうして数秒にまで低減することができる。
1. 2つの反応工程、つまりアミン塩酸塩の塩化カルバモイルへのホスゲン化と、塩化カルバモイルのイソシアネート及び塩化水素への分解は、別々の段階又は反応器において部分的にもしくは完全に実施され、その際、非常に高い化学的収率、非常に高い空時収量及び同時に非常に低いホスゲン滞留量を、それぞれの特定の反応について最適な圧力及び最適な温度の互いに無関係の調整によって、かつそれぞれの場合に最も好ましい反応器設計の選択によって達成することが可能である。
(1)イソシアネートとアミン塩酸塩とによる副生成物形成は、塩化カルバモイル/イソシアネート平衡がイソシアネート側にシフトすることによって優勢となる;
(2)アミン塩酸塩のホスゲン化に必要なホスゲンは、塩化水素と一緒にも除去される;及び
(3)反応混合物から放出される塩化水素ガスと、特に蒸発したホスゲンは、反応混合物の冷却をもたらし、それは固体の塩化カルバモイルとアミン塩酸塩の大量の沈殿を引き起こすことがある
からである。
EP−A−0830894号に記載されるものに相応する混合反応器において、トルエンジアミン(TDA)をオルト−ジクロロベンゼン中に80℃の温度で溶かした18.0質量%の溶液10t/時間と、ホスゲンをオルト−ジクロロベンゼン中に−10℃の温度で溶かした61.9質量%の溶液17t/時間とを混合し、そして連続的に35kWの入力下で反応させた。反応器中の圧力は7.6バールであり、かつ反応器出口における温度は、96.3℃であった。
EP−A−0830894号に記載されるものに相応する混合反応器中において、MDA(平均分子量:242g/モル)をモノクロロベンゼン中に106℃の温度で溶かした30.0質量%の溶液76.5kg/時間と、ホスゲンをモノクロロベンゼン中に4℃の温度で溶かした45質量%の溶液88.3kg/時間とを混合し、そして0.75kWの入力下で連続的に反応させた。反応器中の圧力は18.5バールであり、かつ反応器出口における温度は、128℃であった。
− 25℃での粘度 193mPas
− NCO含有率 31.0%
− 色E430 0.0931)
− 色E520 0.0161)
1)得られたイソシアネート1.0gを、クロロベンゼン中に溶解させ、そしてクロロベンゼンで50mlに希釈した。得られた溶液の吸光度を、波長430nm及び520nmにおいて、Dr.Lange LICO 300型光度計で測定した。
Claims (7)
- 有機アミンとホスゲンとを反応させることによって:
a)ダイナミックミキサ中で実施される、アミンを塩化カルバモイル及びアミン塩酸塩に転化させるための第一段階と、
b)少なくとも1つの反応器中で実施される、第一段階により形成されたアミン塩酸塩を塩化カルバモイルに転化させるための第二段階と、
c)少なくとも1つの材料分離装置中で実施される、塩化カルバモイルをイソシアネートと塩化水素とに分離させるための第三段階と
を含む少なくとも3段階でイソシアネートを製造する方法において、
(1)第二段階の反応器圧力は、第一段階のダイナミックミキサの圧力より高いか又はそれと等しく、かつ(2)第三段階の材料分離装置の圧力は、第二段階の反応器における圧力より低いイソシアネートを製造する方法。 - 製造されたイソシアネートが、ジフェニルメタンジイソシアネート(MDI)、ポリフェニレン−ポリメチレンポリイソシアネート(PMDI)、ジフェニルメタンジイソシアネート(MDI)とポリフェニレン−ポリメチレンポリイソシアネート(PMDI)の混合物、トルエンジイソシアネート(TDI)、ヘキサメチレンジイソシアネート(HDI)、又はイソホロンジイソシアネート(IPDI)である請求項1に記載の方法。
- 管形反応器、撹拌槽反応器又は可動内部取付物を有さない保持装置が、第二段階の反応器として使用される請求項1に記載の方法。
- 第二段階の反応器中での滞留時間が、1秒〜30分である請求項1に記載の方法。
- 別個の排気路を有する熱交換器、反応カラム、反応塔、又は少なくとも1つの反応塔と少なくとも1つの反応カラムとの直列接続された組み合わせが、第三段階の材料分離装置として使用される請求項1に記載の方法。
- 有機アミンとホスゲンとの反応が、不活性溶剤中で、かつ過剰のホスゲンをもって実施される請求項1に記載の方法。
- 第二段階の反応器圧力が、第一段階のダイナミックミキサの圧力より高い請求項1〜6までのいずれか1項記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/474,795 US7547801B2 (en) | 2006-06-26 | 2006-06-26 | Process for the continuous preparation of isocyanates |
US11/474795 | 2006-06-26 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008007506A JP2008007506A (ja) | 2008-01-17 |
JP5388427B2 true JP5388427B2 (ja) | 2014-01-15 |
Family
ID=38462382
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007167869A Active JP5388427B2 (ja) | 2006-06-26 | 2007-06-26 | イソシアネートの連続的な製造方法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US7547801B2 (ja) |
EP (1) | EP1873142B1 (ja) |
JP (1) | JP5388427B2 (ja) |
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DE102006060181A1 (de) * | 2006-12-18 | 2008-06-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Toluylendiisocyanat |
DE102008012037A1 (de) | 2008-03-01 | 2009-09-03 | Bayer Materialscience Ag | Verfahren zur Herstellung von Methylen-diphenyl-diisocyanaten |
EP2128127A1 (de) * | 2008-05-31 | 2009-12-02 | Bayer MaterialScience AG | Ammoniumchloridabtrennung aus der Gasphase |
DE102008063728A1 (de) * | 2008-12-18 | 2010-06-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
CN101612547B (zh) * | 2009-07-28 | 2012-05-30 | 赛鼎工程有限公司 | 生产甲苯二异氰酸酯的列管式撞击流反应器及操作系统 |
CN101698652B (zh) * | 2009-11-05 | 2012-12-26 | 甘肃银达化工有限公司 | 一种tdi生产中循环溶剂的净化方法 |
CN101805272B (zh) * | 2010-04-21 | 2013-08-28 | 万华化学集团股份有限公司 | 一种通过界面光气化反应制备异氰酸酯的方法 |
FR2965490B1 (fr) | 2010-09-30 | 2013-01-11 | Aet Group | Dispositif et procede pour la phosgenation en continu |
US9321720B2 (en) | 2010-10-14 | 2016-04-26 | Basf Se | Process for preparing isocyanates |
JP5883011B2 (ja) * | 2010-10-14 | 2016-03-09 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | イソシアネートの製造方法 |
CN102070491B (zh) * | 2010-11-26 | 2013-12-18 | 万华化学集团股份有限公司 | 基于成盐光气化反应制备苯二亚甲基二异氰酸酯的方法 |
JP5861060B2 (ja) | 2010-12-27 | 2016-02-16 | パナソニックIpマネジメント株式会社 | 無線基地局、無線通信端末、無線通信システム及び方法 |
DE102011087654A1 (de) | 2011-12-02 | 2013-06-06 | Bayer Materialscience Aktiengesellschaft | Verfahren zur Herstellung von Isocyanaten |
IN2014DN07241A (ja) | 2012-03-19 | 2015-04-24 | Bayer Ip Gmbh | |
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BR112018077149B1 (pt) | 2016-06-29 | 2022-10-18 | Covestro Deutschland Ag | Processo para produção de anilina ou de outros produtos derivados da anilina |
US10618871B2 (en) | 2016-08-17 | 2020-04-14 | Covestro Deutschland Ag | Process for producing isocyanate and at least one further chemical product in an integrated production |
HUE053496T2 (hu) | 2016-09-01 | 2021-07-28 | Covestro Intellectual Property Gmbh & Co Kg | Eljárás izocianátok elõállítására |
WO2018114841A1 (de) | 2016-12-20 | 2018-06-28 | Covestro Deutschland Ag | Verfahren zur herstellung von aminobenzoesäure oder eines aminobenzoesäurefolgeprodukts |
CN110072845B (zh) | 2016-12-21 | 2022-04-08 | 科思创德国股份有限公司 | 制备异氰酸酯的方法 |
US11225546B2 (en) * | 2017-03-06 | 2022-01-18 | Dow Global Technologies Llc | Process for preparing isocyanates |
HUE056221T2 (hu) | 2017-07-03 | 2022-02-28 | Covestro Intellectual Property Gmbh & Co Kg | Termelõ berendezés kémiai termék elõállítására H-funkciós reagens és foszgén reagáltatásával és eljárás ennek üzemeltetésére |
CN109748822B (zh) * | 2017-11-08 | 2022-01-07 | 万华化学集团股份有限公司 | 一种制备异氰酸酯单体的方法和系统 |
CN108147979B (zh) * | 2017-12-25 | 2020-07-28 | 万华化学集团股份有限公司 | 一种制备二苯基甲烷二异氰酸酯和/或多苯基多亚甲基多异氰酸酯的方法 |
PT3735405T (pt) | 2018-01-05 | 2021-12-29 | Covestro Intellectual Property Gmbh & Co Kg | Processo para fabrico de di-isocianatos de metilenodifenileno e poli-isocianatos de polimetileno-polifenileno |
WO2019234092A1 (de) | 2018-06-07 | 2019-12-12 | Covestro Deutschland Ag | Verfahren zur herstellung von aminobenzoesäure oder eines aminobenzosäure-folgeprodukts |
HUE060351T2 (hu) | 2018-07-27 | 2023-02-28 | Covestro Intellectual Property Gmbh & Co Kg | Eljárás anilin vagy anilin-származék elõállítására |
US10851048B2 (en) * | 2018-11-13 | 2020-12-01 | Covestro Deutschland Ag | Process for preparing an isocyanate by partly adiabatically operated phosgenation of the corresponding amine |
US10875827B2 (en) | 2018-11-13 | 2020-12-29 | Covestro Deutschland Ag | Process for preparing an isocyanate by partly adiabatic phosgenation of the corresponding amine |
CN120136741A (zh) | 2019-09-17 | 2025-06-13 | 科思创德国股份有限公司 | 制备异氰酸酯的方法 |
WO2021122625A1 (de) | 2019-12-18 | 2021-06-24 | Covestro Deutschland Ag | Verfahren zur herstellung von di- und polyisocyanaten der diphenylmethanreihe |
JP2023526598A (ja) * | 2020-05-15 | 2023-06-22 | コベストロ、ドイチュラント、アクチエンゲゼルシャフト | イソシアネートの連続的な製造用のプラントを運転する方法 |
US20240199529A1 (en) | 2021-06-02 | 2024-06-20 | Covestro Deutschland Ag | Process for preparing aniline or an aniline derivative |
CN113666844A (zh) * | 2021-09-22 | 2021-11-19 | 德州绿霸精细化工有限公司 | 一种连续生产2,6-二氟苯甲酰基异氰酸酯的方法 |
KR20250010582A (ko) | 2022-04-06 | 2025-01-21 | 코베스트로 도이칠란트 아게 | 아닐린 또는 아닐린 전환 생성물을 제조하는 방법 |
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JP2008007506A (ja) | 2008-01-17 |
KR101385809B1 (ko) | 2014-04-16 |
US7547801B2 (en) | 2009-06-16 |
ES2334520T3 (es) | 2010-03-11 |
EP1873142A1 (en) | 2008-01-02 |
EP1873142B1 (en) | 2009-11-04 |
US20070299279A1 (en) | 2007-12-27 |
KR20070122404A (ko) | 2007-12-31 |
CN101100447B (zh) | 2012-06-13 |
PT1873142E (pt) | 2010-01-06 |
RU2007123665A (ru) | 2008-12-27 |
ATE447549T1 (de) | 2009-11-15 |
DE602007003049D1 (de) | 2009-12-17 |
PL1873142T3 (pl) | 2010-04-30 |
CN101100447A (zh) | 2008-01-09 |
RU2445155C2 (ru) | 2012-03-20 |
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