JP5383202B2 - 少なくとも1つの有機出発化合物の不均一触媒気相部分酸化方法 - Google Patents
少なくとも1つの有機出発化合物の不均一触媒気相部分酸化方法 Download PDFInfo
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- JP5383202B2 JP5383202B2 JP2008548971A JP2008548971A JP5383202B2 JP 5383202 B2 JP5383202 B2 JP 5383202B2 JP 2008548971 A JP2008548971 A JP 2008548971A JP 2008548971 A JP2008548971 A JP 2008548971A JP 5383202 B2 JP5383202 B2 JP 5383202B2
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- 229910052776 Thorium Inorganic materials 0.000 description 1
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- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 230000037237 body shape Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000006392 deoxygenation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-N potassium;ethoxymethanedithioic acid Chemical compound [K+].CCOC(S)=S JCBJVAJGLKENNC-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
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- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
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- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
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- B01J8/067—Heating or cooling the reactor
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
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- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
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- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
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- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00168—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles
- B01J2208/00212—Plates; Jackets; Cylinders
- B01J2208/00221—Plates; Jackets; Cylinders comprising baffles for guiding the flow of the heat exchange medium
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- Catalysts (AREA)
Description
式(IV)
Mo12BiaFebX1 cX2 dX3 eX4 fOn (IV)
[式中、変数はそれぞれ以下のように定義される:
X1=ニッケルおよび/またはコバルト、
X2=タリウム、アルカリ金属、および/またはアルカリ土類金属、
X3=亜鉛、リン、ヒ素、ホウ素、アンチモン、錫、セリウム、鉛、および/またはタングステン、
X4=ケイ素、アルミニウム、チタニウン、および/またはジルコニウム、
a=0.5〜5、
b=0.01〜5、好ましくは2〜4、
c=0〜10、好ましくは3〜10、
d=0〜2、好ましくは0.02〜2、
e=0〜8、好ましくは0〜5、
f=0〜10、ならびに、
n=式IV中の酸素以外の元素の原子価および頻度によって決定される数値]。
式(V)
[Y1 a'Y2 b'Ox']p[Y3 c'Y4 d'Y5 e'Y6 f'Y7 g'Y2 h'Oy']p (V)
[式中、変数はそれぞれ以下のように定義される:
Y1=ビスマスのみ、あるいはビスマスおよびテリウム、アンチモン、錫および銅の元素の少なくとも1つ、
Y2=モリブデン、またはタングステン、またはモリブデンおよびタングステン、
Y3=アルカリ金属、タリウム、および/またはサマリウム、
Y4=アルカリ土類金属、ニッケル、コバルト、銅、マンガン、亜鉛、錫、カドミウム、および/または水銀、
Y5=鉄、あるいは鉄ならびにクロミウムおよびセリウムの元素の少なくとも1つ、
Y6=リン、ヒ素、ホウ素、および/またはアンチモン、
Y7=希土類金属、チタン、ジルコニウム、ニオブ、タンタル、レニウム、ルーテニウム、ロジウム、銀、金、アルミニウム、ガリウム、インジウム、ケイ素、ゲルマニウム、鉛、トリウム、および/またはウラニウム、
a’=0.01〜8、
b’=0.1〜30、
c’=0〜4、
d’=0〜20、
e’>0〜20、
f’=0〜6、
g’=0〜15、
h’=8〜16、
x’,y’=式V中の酸素以外の元素の原子価および頻度によって決定される数値、
p,q=p/q比が0.1〜10である数値]、
局所的環境とは異なる組成物のために局所的環境から分界される化学組成物Y1 a'・Y2 b'・Ox'の3次元領域を含み、その最大直径(領域の中心を通り、かつ領域の表面(境界)上の2つの点を結ぶ最長の直線)が、1nm〜100μm、多くの場合は10nm〜500nm、または1μm〜50μmもしくは25μmである、
組成物でもある。
式(VI)
[Bia"Z2 b"Ox"]p"[Z2 12Z3 c"Z4 d"Fee"Z5 f"Z6 g"Z7 h"Oy"]q" (VI)
[式中、変数はそれぞれ以下のように定義される:
Z2=モリブデン、またはタングステン、またはモリブデンおよびタングステン、
Z3=ニッケルおよび/またはコバルト、
Z4=タリウム、アルカリ金属、および/またはアルカリ土類金属、
Z5=リン、ヒ素、ホウ素、アンチモン、錫、セリウム、および/または鉛、
Z6=ケイ素、アルミニウム、チタン、および/またはジルコニウム、
Z7=銅、銀、および/または金、
a’’=0.1〜1、
b’’=0.2〜2、
c’’=3〜10、
d’’=0.02〜2、
e’’=0.01〜5、好ましくは0.1〜3、
f’’=0〜5、
g’’=0〜10、
h’’=0〜1、
x’’,y’’=式VI中の酸素以外の元素の原子価および頻度によって決定される数値、
p’’,q’’=p’’/q’’比が0.1〜5、好ましくは0.5〜2である数値]、
特に、以下の通りである組成物VIが好ましい:
Z2 b''=(タングステン)b''およびZ2 12=(モリブデン)12。
式(VII)
Mo12VaX1 bX2 cX3 dX4 eX5 fX6 gOn (VII)
[式中、変数はそれぞれ以下のように定義される:
X1=W、Nb、Ta、Cr、および/またはCe、
X2=Cu、Ni、Co、Fe、Mn、および/またはZn、
X3=Sbおよび/またはBi、
X4=1つ以上のアルカリ金属、
X5=1つ以上のアルカリ土類金属、
X6=Si、Al、Tiおよび/またはZr、
a=1〜6、
b=0.2〜4、
c=0.5〜18、
d=0〜40、
e=0〜2、
f=0〜4、
g=0〜40、および
n=式VII中の酸素以外の元素の原子価および頻度によって決定される数値]。
X1=W、Nb、Ta、および/またはCr、
X2=Cu、Ni、Co、および/またはFe、
X3=Sb、
X4=Naおよび/またはK、
X5==Ca、Sr、および/またはBa、
X6=Si、Al、および/またはTi、
a=1〜5、
b=0.5〜2、
c=0.5〜3、
d=0〜2、
e=0〜0.2、
f=0〜1、
n=式VII中の酸素以外の元素の原子価および頻度によって決定される数値。
式(VIII)
Mo12Va'Y1 b'Y2 c'Y5 f'Y6 g'On' (VIII)
[式中、
Y1=Wおよび/またはNb、
Y2=Cuおよび/またはNi、
Y5=Caおよび/またはSr、
Y6=Siおよび/またはAl、
a’=2〜4、
b’=1〜1.5、
c’=1〜3、
f=0〜0.5、
g’=0〜8、
n=式VIII中の酸素以外の元素の原子価および頻度によって決定される数値]。
式(IX)
[D]p[E]q (IX)
[式中、
D=Mo12Va''Z1 b''Z2 c''Z3 d''Z4 e''Z5 f''Z6 g''Ox、
E=Z7 12Cuh''Hi''Oy''、
Z1=W、Nb、Ta、Cr、および/またはCe、
Z2=Cu、Ni、Co、Fe、Mn、および/またはZn、
Z3=Sbおよび/またはBi、
Z4=Li、Na、K、Rb、Cs、および/またはH、
Z5=Mg、Ca、Sr、および/またはBa、
Z6=Si、Al、Ti、および/またはZr、
Z7=Mo、W、V、Nb、および/またはTa、好ましくはMoおよび/またはW、
a’’=1〜8、
b’’=0.2〜5、
c’’=0〜23、
d’’=0〜50、
e’’=0〜2、
f’’=0〜5、
g’’=0〜50、
h’’=4〜30、
i’’=0〜20、および
x’’,y’’=式IX中の酸素以外の元素の原子価および頻度によって決定される数値、ならびに
p,q=p/q比が160:1〜1:1であるゼロ以外の数値]、
微粒子形態(出発組成物1)で以下の多金属酸化物組成物Eを個別に予備成形した後:
Z7 12Cuh"Hi"Oy" (E)
予備形成された固体出発組成物1を、所望のp:q比で以下の化学量論D(出発組成物2)の上述の元素を含む元素Mo、V、Z1、Z2、Z3、Z4、Z5、Z6の供給源の水溶液、水性懸濁液、または微粒子化した乾燥混合物に組み込み:
Mo12Va"Z1 b"Z2 c"Z3 d"Z4 e"Z5 f"Z6 g" (D)
結果として得られる場合がある水性混合物を乾燥させ、250℃〜600℃の温度にて乾燥させて所望の触媒形状を得る前または後に、得られた乾燥先駆物質組成物をか焼することにより、得ることができる、
組成物でもある。
5体積%または6〜11体積%のプロペン、
2体積%または6〜12体積%の水、
0体積%超、しばしば0.5体積%以上または1体積%以上〜10体積%のプロパン、
プロペン、プロパン、水、酸素、および窒素以外の0体積%以上〜5体積%の成分、
V1が1〜3である十分な分子酸素、ならびに、
残りとして全量の最高100体積%の分子窒素。
6〜9体積%のプロピレン、
8〜18体積%の分子酸素、
6〜30体積%または35体積%のプロパン、および、
32〜72体積%の分子窒素。
4.5〜8体積%のアクロレイン、
2.25〜9体積%の分子酸素、
6〜30体積%または35体積%のプロパン、
32〜72体積%の分子窒素、および、
5〜30体積%の蒸気。
4〜25体積%のプロピレン、
6〜70体積%のプロパン、
5〜60体積%のH2O、
8〜65体積%のO2、および、
0.3〜20体積%のH2。
3〜25体積%のアクロレイン、
5〜65体積%の分子酸素、
6〜70体積%のプロパン、
0.3〜20体積%の分子水素、および、
8〜65体積%の蒸気。
0〜0.1体積%のその他の物質、例えばジフェニル、ジフェニルエーテル、および/またはジフェニルフタレート、
0〜0.1体積%のアクリル酸、
0〜0.1体積%のアクロレイン、
3〜5体積%の酸素、
1〜5体積%の蒸気、
0〜3体積%の一酸化炭素、
0〜8体積%の二酸化炭素、
0〜2体積%のプロパン、
0.1〜0.5体積%のプロピレン、ならびに、
85〜95体積%の窒素。
I. 第1の反応段階の概要
使用する熱媒:
60質量%の硝酸カリウムおよび40質量%の亜硝酸ナトリウムの塩溶融物を、反応ガス混合物に対して対向流で通す。触媒管に固定触媒床を新規に充填して、320℃の温度で供給し、322℃の温度で除去した。
フェライト鋼
触媒管の組成:
長さ3200mm
内径26mm
外径31mm
(壁厚2.5mm)
出発反応ガス混合物1の組成物:
5.4体積%のプロピレン、
10.5体積%の分子酸素、
1.2体積%のCOx、
81.3体積%のN2、および、
1.6体積%のH2O。
110Nl/l・時
触媒管の新規の充填物(反応ガス混合物の流れ方向における):
ゾーンA:50cm
7mm×7mm×4mm(外径×長さ×内径)の形状のステアタイトリングの予備床
ゾーンB:100cm
5mm×3mm×2mm(外径×長さ×内径)の形状の30質量%のステアタイトリング(CeramTec製のステアタイトC 220)とゾーンCの70質量%の無担持触媒との均一混合物を有する触媒充填物
ゾーンC:170cm
ドイツ特許出願第DE−A100 46 957号の実施例1に記載の環状の(5mm×3mm×2mm=外径×長さ×内径)無担持触媒を有する触媒充填物
II. 中間冷却および2次ガスの追加
アクロレインの喪失が実質的にない状態で管束熱交換器において60質量%の硝酸カリウムおよび40質量%の亜硝酸ナトリウムの塩溶融物と間接的に熱交換することによって、第1の反応段階の産物ガス混合物を250℃に冷却した。その後、得られる混合物におけるO2:アクロレインのモル比が約1.28になるような量で、140℃の温度を有する圧縮空気を追加した。この混合物を220℃の温度で第2の反応段階に供給した。
触媒管は、第1の反応段階の触媒管に対応していた。塩溶融物(第1の反応段階と同じ組成物)および反応ガス混合物を対向流で通した。触媒管に固定触媒床を新規に充填して、塩溶融物を260℃の温度で供給し、262℃の温度で除去した。
7mm×7mm×4mm(外径×長さ×内径)の形状のステアタイトリング(CeramTec製のステアタイトC 220)の20cmの予備床
ゾーンB:
7mm×3mm×4mm(外径×長さ×内径)の形状の30質量%(あるいは35質量%)のステアタイトリング(CeramTec製のステアタイトC220)と、ゾーンCの70質量%(あるいは65質量%)のコーティングされた触媒との均一混合物を有する、100cm(あるいは120cm)の触媒充填物
ゾーンC:
ドイツ特許出願第DE−A 100 46 928号の調製例5に記載の環状の(約7mm×3mm×4mm=外径×長さ×内径)コーティングされた触媒を有する200cm(あるいは180cm)の触媒充填物
IV. 結果(アクリル酸形成の選択性はほぼ一定のままであった)
A) 実施例
第2の反応段階の産物ガス混合物の分析により、以下の結果が得られた。
実施例の手順を繰り返したが、但し、ゾーンBを吸い出し、新規のゾーンBと交換した点が異なる。この新規のゾーンBは、元のゾーンBと同様に、ドイツ特許出願第DE−A 100 46 928号の実施例5に記載の通り、7mm×3mm×4mmの形状を有する、わずか30質量%のステアタイトリングおよび70質量%の新規のコーティングされた触媒を有していた。
Claims (11)
- 反応室に新規に設置した固定触媒床上で、分子酸素により少なくとも1つの有機出発化合物の不均一触媒気相部分酸化を行う方法であって、該部分酸化のために、前記少なくとも1つの有機出発化合物と前記分子酸素とを含む反応ガス混合物を前記固定触媒床に通し、前記反応室の外側に通される液体熱媒との間接的な熱交換により反応熱を除去し、動作時間が長くなるにつれて前記固定触媒床の品質低下が進んだら、前記固定触媒床の全体ではなく一部のみを交換用固定触媒床部分で交換して、前記固定触媒床の前記品質を回復させる方法において、前記交換用固定触媒床部分の体積比活性が、交換した固定触媒床部分の新規に設置したときの体積比活性よりも低いことを特徴とする方法。
- 前記気相部分酸化が、プロピレンからアクロレインおよび/またはアクリル酸への気相部分酸化、あるいはイソブテンからメタクロレインおよび/またはメタクリル酸への気相部分酸化、あるいはアクロレインからアクリル酸への気相部分酸化、メタクロレインからメタクリル酸への気相部分酸化、あるいはプロパンからアクリル酸への気相部分酸化、あるいはイソブタンからメタクリル酸への気相部分酸化であることを特徴とする、請求項1に記載の方法。
- 前記少なくとも1つの有機出発化合物が、プロピレン、アクロレイン、1−ブテン、2−ブテン、エタン、ベンゼン、m−キシレン、p−キシレン、イソブタン、イソブテン、tert−ブタノール、イソブチルアルデヒド、tert−ブタノールメチルエーテル、o−キシレン、ナフタレン、ブタジエン、エチレン、プロパン、およびメタクロレインからなる群の少なくとも1つの有機出発化合物であることを特徴とする、請求項1または2に記載の方法。
- 前記気相部分酸化が、2段階気相部分酸化の第2の段階であることを特徴とする、請求項1から3までのいずれか1項に記載の方法。
- 前記気相部分酸化が、プロピレンからアクリル酸への2段階気相部分酸化におけるアクロレインからアクリル酸への部分酸化であることを特徴とする、請求項4に記載の方法。
- 前記固定触媒床を前記反応ガス混合物が1回通過した際の前記有機出発化合物の変換、および前記反応ガス混合物の組成、および前記触媒床への反応ガス混合物の負荷量が同じである条件で、前記交換用固定触媒床部分との交換後の前記固定触媒床のホットスポット膨張ΔTHB nと、前記交換用固定触媒床部分との交換前のホットスポット膨張ΔTHB vとの差dΔT(dΔT=ΔTHB n−ΔTHB vとして表わす)が、30℃以下であるように、前記交換用固定触媒床部分の前記体積比活性を決めることを特徴とする、請求項1から5までのいずれか1項に記載の方法。
- dΔTが−15〜+10℃であることを特徴とする、請求項6に記載の方法。
- dΔTが−10〜0℃であることを特徴とする、請求項6に記載の方法。
- 前記反応室が反応管の内部であることを特徴とする、請求項1から8までのいずれか1項に記載の方法。
- 前記反応管が管束反応器内に存在することを特徴とする、請求項9に記載の方法。
- 前記交換用固定触媒床部分と交換した前記固定触媒床の前記部分が、前記反応ガス混合物の流れ方向において、前記固定触媒床の床長さの80%までに及ぶことを特徴とする、請求項1から10までのいずれか1項に記載の方法。
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- 2006-12-21 EP EP06841539A patent/EP1973641B1/de active Active
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- 2006-12-21 BR BRPI0620948A patent/BRPI0620948B1/pt active IP Right Grant
- 2006-12-21 WO PCT/EP2006/070069 patent/WO2007077145A1/de active Application Filing
- 2006-12-21 RU RU2008131799/04A patent/RU2440188C2/ru active
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CN101336131A (zh) | 2008-12-31 |
BRPI0620948A2 (pt) | 2011-11-29 |
MY143495A (en) | 2011-05-31 |
RU2440188C2 (ru) | 2012-01-20 |
US7518015B2 (en) | 2009-04-14 |
US20070155988A1 (en) | 2007-07-05 |
DE102006000996A1 (de) | 2007-07-12 |
KR20080083350A (ko) | 2008-09-17 |
EP1973641B1 (de) | 2009-07-22 |
RU2008131799A (ru) | 2010-02-10 |
JP2009522320A (ja) | 2009-06-11 |
DE502006004343D1 (de) | 2009-09-03 |
WO2007077145A1 (de) | 2007-07-12 |
KR101393797B1 (ko) | 2014-05-12 |
CN101336131B (zh) | 2010-09-08 |
BRPI0620948B1 (pt) | 2016-03-01 |
EP1973641A1 (de) | 2008-10-01 |
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