FI87453C - Foerfarande foer selektiv hydrering av acetylener - Google Patents

Foerfarande foer selektiv hydrering av acetylener Download PDF

Info

Publication number: FI87453C
Authority: FI; Finland
Prior art keywords: catalyst; hydrogen; feed; butadiene; alkynes
Prior art date: 1986-12-30

Application number

FI875774A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI87453B (fi

FI875774A0 (fi

FI875774A (fi

Inventor

Guy L G Debras

Clippeleir Georges E M J De

Raymond M Cahen

Jacques F Grootjans

Original Assignee

Labofina Sa

Priority date (The priority date 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 date listed.)

1986-12-30

Filing date

1987-12-30

Publication date

1993-01-11

1987-12-30 Application filed by Labofina Sa filed Critical Labofina Sa

1987-12-30 Publication of FI875774A0 publication Critical patent/FI875774A0/fi

1988-07-01 Publication of FI875774A publication Critical patent/FI875774A/fi

1992-09-30 Publication of FI87453B publication Critical patent/FI87453B/fi

1993-01-11 Application granted granted Critical

1993-01-11 Publication of FI87453C publication Critical patent/FI87453C/fi

Links

238000000034 method Methods 0.000 title claims description 41
238000005984 hydrogenation reaction Methods 0.000 title claims description 39
125000002534 ethynyl group Chemical class [H]C#C* 0.000 title description 15
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 73
239000003054 catalyst Substances 0.000 claims description 72
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 48
239000001257 hydrogen Substances 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
150000001345 alkine derivatives Chemical class 0.000 claims description 31
229910052763 palladium Inorganic materials 0.000 claims description 24
239000007788 liquid Substances 0.000 claims description 14
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 13
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
239000007789 gas Substances 0.000 claims description 5
239000007791 liquid phase Substances 0.000 claims description 5
239000012071 phase Substances 0.000 claims description 3
229910052755 nonmetal Inorganic materials 0.000 claims 1
KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 23
229930195733 hydrocarbon Natural products 0.000 description 20
150000002430 hydrocarbons Chemical class 0.000 description 20
239000000203 mixture Substances 0.000 description 14
235000013844 butane Nutrition 0.000 description 10
WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 10
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 9
239000004215 Carbon black (E152) Substances 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
239000000243 solution Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000010931 gold Substances 0.000 description 6
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 4
230000008929 regeneration Effects 0.000 description 4
238000011069 regeneration method Methods 0.000 description 4
238000004230 steam cracking Methods 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
230000004913 activation Effects 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
239000011148 porous material Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
229920003051 synthetic elastomer Polymers 0.000 description 3
239000005061 synthetic rubber Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
230000003213 activating effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000001514 detection method Methods 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
229910052737 gold Inorganic materials 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
230000000977 initiatory effect Effects 0.000 description 2
230000007774 longterm Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
238000010926 purge Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910000570 Cupronickel Inorganic materials 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000006384 oligomerization reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000003860 storage Methods 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/48—Silver or gold
- B01J23/52—Gold
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0203—Impregnation the impregnation liquid containing organic compounds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/06—Washing
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

FI875774A 1986-12-30 1987-12-30 Foerfarande foer selektiv hydrering av acetylener FI87453C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8631017		1986-12-30
GB8631017A GB2199588B (en)	1986-12-30	1986-12-30	Process for the selective hydrogenation of acetylenes

Publications (4)

Publication Number	Publication Date
FI875774A0 FI875774A0 (fi)	1987-12-30
FI875774A FI875774A (fi)	1988-07-01
FI87453B FI87453B (fi)	1992-09-30
FI87453C true FI87453C (fi)	1993-01-11

Family

ID=10609665

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI875774A FI87453C (fi)	1986-12-30	1987-12-30	Foerfarande foer selektiv hydrering av acetylener

Country Status (9)

Country	Link
JP (1)	JP2560056B2 (it)
BE (1)	BE1000871A4 (it)
CA (1)	CA1290354C (it)
DE (1)	DE3744086C2 (it)
FI (1)	FI87453C (it)
FR (1)	FR2609023B1 (it)
GB (1)	GB2199588B (it)
IT (1)	IT1223624B (it)
NL (1)	NL8703157A (it)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19500366C1 (de) *	1995-01-09	1996-05-02	Basf Ag	Palladium-Trägerkatalysator und seine Verwendung
US6509292B1 (en) *	2001-03-30	2003-01-21	Sud-Chemie Inc.	Process for selective hydrogenation of acetylene in an ethylene purification process
DE102008043344A1 (de)	2008-10-31	2010-05-06	Evonik Oxeno Gmbh	Verfahren zur Herstellung von 1-Alkoxyocta-2,7-dien

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB510343A (en) *	1936-10-22	1939-07-26	Ig Farbenindustrie Ag	A process of hydrogenating monovinylacetylene
FR1217305A (fr) *	1957-12-17	1960-05-03	Bayer Ag	Procédé pour éliminer l'acétylène, le méthylacétylène et l'allène à partirde mélanges d'hydrocarbures
DE1184336B (de) *	1963-07-10	1964-12-31	Huels Chemische Werke Ag	Verfahren zur Entfernung von Methylacetylen und Propadien aus einem ueberwiegend Propen enthaltenden C-Kohlenwasserstoffgemisch
DE1210795B (de) *	1964-11-14	1966-02-17	Huels Chemische Werke Ag	Verfahren zur Entfernung von Butadien und bzw. oder Acetylenen aus einem ueberwiegend Butene bzw. Butadien enthaltenden C-Kohlenwasserstoffgemisch
DE1568542C3 (de) *	1966-06-15	1974-07-18	Bayer Ag, 5090 Leverkusen	Verfahren zur katalytischen Umwandlung von Butadien- und n-Buten-1-haltigen C tief 4 - Kohlenwasserstoffen
US3842137A (en) *	1973-01-02	1974-10-15	Monsanto Co	Selective hydrogenation of c4 acetylenic hydrocarbons
US3898298A (en) *	1973-04-13	1975-08-05	Atlantic Richfield Co	Selective hydrogenation of vinyl acetylene
US3859377A (en) *	1973-12-13	1975-01-07	Monsanto Co	Selective hydrogenation of c' 4 'acetylenic hydrocarbons
FR2421858A1 (fr) *	1978-04-05	1979-11-02	Inst Francais Du Petrole	Procede d'hydrogenation selective d'une fraction d'hydrocarbures renfermant au moins un hydrocarbure diolefinique et au moins un hydrocarbure acetylenique
JPS54141706A (en) *	1978-04-21	1979-11-05	Nippon Oil Co Ltd	Removal of acetylenes in 4c hydrocarbon mixture containing butadiene
US4247745A (en) *	1978-09-13	1981-01-27	Westinghouse Electric Corp.	Vacuum-type contactor assembly
FR2460989A1 (fr) *	1979-07-06	1981-01-30	Inst Francais Du Petrole	Procede de purification d'une coupe d'hydrocarbures aromatiques contenant des hydrocarbures insatures olefiniques et acetyleniques
DE3143647A1 (de) *	1981-11-04	1983-05-11	Chemische Werke Hüls AG, 4370 Marl	Verfahren zur selektiven hydrierung von mehrfach ungesaettigten kohlenwasserstoffen in kohlenwasserstoff-gemischen
JPS58149987A (ja) *	1982-03-02	1983-09-06	Sumitomo Chem Co Ltd	炭化水素類の選択的水素添加の方法

1986
- 1986-12-30 GB GB8631017A patent/GB2199588B/en not_active Expired - Fee Related
1987
- 1987-12-24 DE DE3744086A patent/DE3744086C2/de not_active Revoked
- 1987-12-26 JP JP62328448A patent/JP2560056B2/ja not_active Expired - Lifetime
- 1987-12-28 FR FR878718223A patent/FR2609023B1/fr not_active Expired
- 1987-12-29 NL NL8703157A patent/NL8703157A/nl active Search and Examination
- 1987-12-30 BE BE8701501A patent/BE1000871A4/fr not_active IP Right Cessation
- 1987-12-30 FI FI875774A patent/FI87453C/fi not_active IP Right Cessation
- 1987-12-30 CA CA000555579A patent/CA1290354C/en not_active Expired - Lifetime
- 1987-12-30 IT IT23273/87A patent/IT1223624B/it active

Also Published As

Publication number	Publication date
FI87453B (fi)	1992-09-30
FI875774A0 (fi)	1987-12-30
FR2609023B1 (fr)	1989-10-20
JPS63185935A (ja)	1988-08-01
CA1290354C (en)	1991-10-08
BE1000871A4 (fr)	1989-04-25
FR2609023A1 (fr)	1988-07-01
IT8723273A0 (it)	1987-12-30
GB2199588A (en)	1988-07-13
NL8703157A (nl)	1988-07-18
FI875774A (fi)	1988-07-01
IT1223624B (it)	1990-09-29
GB8631017D0 (en)	1987-02-04
DE3744086C2 (de)	2000-05-04
DE3744086A1 (de)	1988-07-14
GB2199588B (en)	1990-12-05
JP2560056B2 (ja)	1996-12-04

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: LABOFINA S.A.

Publication	Publication Date	Title
FI85462B (fi)	1992-01-15	Foerbaettrat foerfarande foer selektiv hydrering av acetylener.
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US20040210097A1 (en)	2004-10-21	Process for selective hydrogenation using a catalytic reactor with a hydrogen-selective membrane
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