JP7469046B2 - メルカプタン、ジスルフィド及びc5炭化水素の存在下でc4炭化水素流から多不飽和炭化水素を除去する方法 - Google Patents
メルカプタン、ジスルフィド及びc5炭化水素の存在下でc4炭化水素流から多不飽和炭化水素を除去する方法 Download PDFInfo
- Publication number
- JP7469046B2 JP7469046B2 JP2020000159A JP2020000159A JP7469046B2 JP 7469046 B2 JP7469046 B2 JP 7469046B2 JP 2020000159 A JP2020000159 A JP 2020000159A JP 2020000159 A JP2020000159 A JP 2020000159A JP 7469046 B2 JP7469046 B2 JP 7469046B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrocarbon stream
- reaction zone
- hydrocarbons
- olefin
- catalyst
- Prior art date
- Legal status (The legal status 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 status listed.)
- Active
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims description 94
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 94
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 54
- 238000000034 method Methods 0.000 title claims description 34
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims description 13
- 150000002019 disulfides Chemical class 0.000 title claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- 150000001336 alkenes Chemical class 0.000 claims description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 17
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 16
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 11
- 239000007791 liquid phase Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 150000002739 metals Chemical class 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 4
- 239000000203 mixture Substances 0.000 description 25
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 17
- 238000005984 hydrogenation reaction Methods 0.000 description 15
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 14
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 235000013844 butane Nutrition 0.000 description 3
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0006—Controlling or regulating processes
-
- 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
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
- C07C5/05—Partial hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14833—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds
- C07C7/1485—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds oxides; hydroxides; salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
- C10G45/34—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used
- C10G45/40—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used containing platinum group metals or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G65/00—Treatment of hydrocarbon oils by two or more hydrotreatment processes only
- C10G65/02—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only
- C10G65/04—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps
- C10G65/06—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps at least one step being a selective hydrogenation of the diolefins
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/00038—Processes in parallel
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/0004—Processes in series
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00162—Controlling or regulating processes controlling the pressure
-
- 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
- C07C2523/42—Platinum
-
- 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)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Water Supply & Treatment (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Treating Waste Gases (AREA)
Description
Claims (12)
- C4炭化水素に加えて、0.01~5質量%の範囲のC5炭化水素、並びに、0.01~200質量ppmの範囲のメルカプタン及び/又はジスルフィドを含むオレフィン含有C4炭化水素流から、多価不飽和炭化水素を除去する方法であって、以下の工程:
1)並列及び/又は直列に連結された1又はそれ以上の反応器からなる第1反応ゾーンにおいて、前記オレフィン含有C4炭化水素流の前記多価不飽和炭化水素の少なくとも一部が、水素化されるか、及び/又は、前記オレフィン含有C4炭化水素流の前記メルカプタン及び/又はジスルフィドと反応する、第1工程であって、前記第1工程は、水素の存在下、及び一酸化炭素の非存在下で第1触媒を用いて行われ、並びに、前記オレフィン含有C4炭化水素流で得られる前記多価不飽和炭化水素の80モル%以下が前記第1工程で水素化されるか、及び/又は反応する、工程、
2)前記第1工程では反応しなかった前記オレフィン含有C4炭化水素流の前記多価不飽和炭化水素を、並列及び/又は直列に連結された1又はそれ以上の反応器からなる第2反応ゾーンで、水素及び一酸化炭素の存在下で第2触媒を用いて、選択的に水素化する第2工程、
ここで、前記第1工程と前記第2工程の間に、少なくとも1つの高ボイラーが除去され、かつ、
前記第1触媒と前記第2触媒は互いに異なる、
を含む、方法。 - 前記第1工程における、水素の前記多価不飽和炭化水素に対するモル比が、0.01~0.8、又は0.1~0.5である、請求項1に記載の方法。
- 前記並列に及び/又は直列に連結された1又はそれ以上の反応器からなる第1反応ゾーンの流入口におけるC4炭化水素流の流入温度が、0~180℃、又は60~150℃、又は80~130℃である、請求項1又は2に記載の方法。
- 前記第1工程は、液相でのみ行われ、存在する前記水素は前記液相に完全に溶解されている、請求項1~3のいずれか一項に記載の方法。
- 前記第2工程において、前記並列に及び/又は直列に連結された1又はそれ以上の反応器からなる第2反応ゾーンに流入する前記オレフィン含有C4炭化水素流中の一酸化炭素の含有量が、前記炭化水素流の総量に基づき、0.05~20ppmである、請求項1~4のいずれか一項に記載の方法。
- 前記第1触媒が、周期表の第10族の金属のうち少なくとも2つの金属、又はパラジウム及び白金を含有する、請求項1~5のいずれか一項に記載の方法。
- 前記第2触媒が、周期表の第10族の金属のうち単一の金属、又はパラジウムを含有する、請求項1~6のいずれか一項に記載の方法。
- 前記並列に及び/又は直列に連結された1又はそれ以上の反応器からなる第2反応ゾーンに流入する前記オレフィン含有C4炭化水素流の流入温度が、0~100℃、又は20~80℃、又は30~60℃の間である、請求項1~7のいずれか一項に記載の方法。
- 前記並列に及び/又は直列に接続された1又はそれ以上の反応器からなる第2反応ゾーンの圧力は、2~50バール、又は6~30バール、又は10~25バールの範囲である、請求項1~8のいずれか一項に記載の方法。
- 前記第2工程が、液相でのみ行われる、請求項1~9のいずれか一項に記載の方法。
- 第1反応ゾーンが単一の反応器からなる、請求項1~10のいずれか一項に記載の方法。
- 第2反応ゾーンが、前記並列又は直列に接続された少なくとも2つの反応器からなる、請求項1~11のいずれか一項に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP19150659.1 | 2019-01-08 | ||
EP19150659.1A EP3680224B1 (de) | 2019-01-08 | 2019-01-08 | Verfahren zur entfernung mehrfach ungesättigter kohlenwasserstoffe aus c4-kohlenwasserstoffströmen in anwesenheit von mercaptanen, disulfiden und c5-kohlenwasserstoffen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2020111566A JP2020111566A (ja) | 2020-07-27 |
JP7469046B2 true JP7469046B2 (ja) | 2024-04-16 |
Family
ID=65010563
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020000159A Active JP7469046B2 (ja) | 2019-01-08 | 2020-01-06 | メルカプタン、ジスルフィド及びc5炭化水素の存在下でc4炭化水素流から多不飽和炭化水素を除去する方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US11952340B2 (ja) |
EP (1) | EP3680224B1 (ja) |
JP (1) | JP7469046B2 (ja) |
KR (1) | KR20200086230A (ja) |
CN (1) | CN111410597A (ja) |
ES (1) | ES2953108T3 (ja) |
MY (1) | MY197239A (ja) |
PL (1) | PL3680224T3 (ja) |
SG (1) | SG10202000057UA (ja) |
TW (1) | TWI841660B (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11254631B2 (en) | 2019-08-21 | 2022-02-22 | Evonik Operations Gmbh | Process for oligomerization of olefins with optimized distillation |
US11332421B2 (en) | 2019-08-21 | 2022-05-17 | Evonik Operations Gmbh | Process for oligomerization of olefins with optimized distillation |
EP3940505B1 (en) | 2020-07-13 | 2023-10-18 | Samsung Electronics Co., Ltd. | Electronic device including solid state drive |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050010071A1 (en) | 2002-01-23 | 2005-01-13 | Catalytic Distillation Technologies | Process for the utilization of refinery C4 streams |
JP2015525750A (ja) | 2012-07-13 | 2015-09-07 | エボニック インダストリーズ アクチエンゲゼルシャフトEvonik Industries AG | C4炭化水素混合物中のメルカプタンのチオエーテル化 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2614295B1 (fr) * | 1987-04-22 | 1989-08-04 | Inst Francais Du Petrole | Procede d'isomerisation du butene-1 en butenes-2 dans une coupe d'hydrocarbures en c4 contenant du butadiene et des composes sulfures. |
DE4123246A1 (de) * | 1991-07-13 | 1993-01-14 | Basf Ag | Verfahren zur selektiven hydrierung von butadienreichen roh-c(pfeil abwaerts)4(pfeil abwaerts)-schnitten |
AU692723B2 (en) * | 1996-02-01 | 1998-06-11 | Phillips Petroleum Company | Catalyst composition and process for selecting hydrogenation of diolefins |
DE10152842A1 (de) * | 2001-10-25 | 2003-05-08 | Oxeno Olefinchemie Gmbh | Hydroisomerisierung von Olefinen mit 4-6 Kohlenstoffatomen |
DE10335510A1 (de) | 2003-07-31 | 2005-03-10 | Stockhausen Chem Fab Gmbh | Beschichteter Katalysator-Trägerkörper |
US20090068440A1 (en) | 2005-06-20 | 2009-03-12 | Gunther Bub | Production of acrolein, acrylic acid and water-absorbent polymer structures made from glycerine |
DE102006039205A1 (de) | 2006-08-22 | 2008-03-20 | Stockhausen Gmbh | Auf nachwachsenden Rohstoffen basierende Acrylsäure und wasserabsorbierende Polymergebilde sowie Verfahren zu deren Herstellung mittels Dehydratisierung |
DE102006039203B4 (de) | 2006-08-22 | 2014-06-18 | Evonik Degussa Gmbh | Verfahren zur Herstellung von durch Kristallisation gereinigter Acrylsäure aus Hydroxypropionsäure sowie Vorrichtung dazu |
DE102008060888A1 (de) | 2008-12-09 | 2010-06-10 | Evonik Stockhausen Gmbh | Verfahren zur Herstellung von Acrolein umfassend die Aufarbeitung einer Rohglycerin-Phase |
DE102010030990A1 (de) | 2010-07-06 | 2012-01-12 | Evonik Oxeno Gmbh | Verfahren zur selektiven Hydrierung von mehrfach ungesättigten Kohlenwasserstoffen in olefinhaltigen Kohlenwasserstoffgemischen |
US9676685B2 (en) * | 2013-06-25 | 2017-06-13 | Dow Technology Investments Llc | Selective hydrogenation process |
JP6228246B2 (ja) | 2015-03-03 | 2017-11-08 | エボニック デグサ ゲーエムベーハーEvonik Degussa GmbH | エテンのオリゴマー化に使用される不均一系触媒の再生 |
EP3255029B1 (de) | 2016-06-10 | 2018-11-14 | Evonik Degussa GmbH | Oligomerisierung von ethen in überkritischer fahrweise |
EP3266757B1 (de) | 2016-07-08 | 2019-12-25 | Evonik Operations GmbH | Herstellung von zumindest 1-hexen und octen aus ethen |
US10227279B2 (en) | 2016-09-12 | 2019-03-12 | Evonik Degussa Gmbh | Dehydrogenation of LPG or NGL and flexible utilization of the olefins thus obtained |
US11253844B2 (en) | 2018-03-14 | 2022-02-22 | Evonik Operations Gmbh | Oligomerization catalyst and process for the production thereof |
US10882028B2 (en) | 2018-03-14 | 2021-01-05 | Evonik Operations Gmbh | Ni-containing catalyst for the oligomerization of olefins |
US10882027B2 (en) | 2018-03-14 | 2021-01-05 | Evonik Operations Gmbh | Process for producing an oligomerization catalyst |
US10850261B2 (en) | 2018-03-14 | 2020-12-01 | Evonik Operations Gmbh | Oligomerization catalyst and process for the production thereof |
-
2019
- 2019-01-08 PL PL19150659.1T patent/PL3680224T3/pl unknown
- 2019-01-08 ES ES19150659T patent/ES2953108T3/es active Active
- 2019-01-08 EP EP19150659.1A patent/EP3680224B1/de active Active
- 2019-12-13 US US16/713,301 patent/US11952340B2/en active Active
-
2020
- 2020-01-03 SG SG10202000057UA patent/SG10202000057UA/en unknown
- 2020-01-06 MY MYPI2020000062A patent/MY197239A/en unknown
- 2020-01-06 JP JP2020000159A patent/JP7469046B2/ja active Active
- 2020-01-07 TW TW109100450A patent/TWI841660B/zh active
- 2020-01-07 KR KR1020200002025A patent/KR20200086230A/ko unknown
- 2020-01-08 CN CN202010016948.1A patent/CN111410597A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050010071A1 (en) | 2002-01-23 | 2005-01-13 | Catalytic Distillation Technologies | Process for the utilization of refinery C4 streams |
JP2015525750A (ja) | 2012-07-13 | 2015-09-07 | エボニック インダストリーズ アクチエンゲゼルシャフトEvonik Industries AG | C4炭化水素混合物中のメルカプタンのチオエーテル化 |
Also Published As
Publication number | Publication date |
---|---|
PL3680224T3 (pl) | 2023-09-11 |
US11952340B2 (en) | 2024-04-09 |
KR20200086230A (ko) | 2020-07-16 |
EP3680224B1 (de) | 2023-05-24 |
EP3680224A1 (de) | 2020-07-15 |
CN111410597A (zh) | 2020-07-14 |
TW202104141A (zh) | 2021-02-01 |
ES2953108T3 (es) | 2023-11-08 |
MY197239A (en) | 2023-06-07 |
SG10202000057UA (en) | 2020-08-28 |
JP2020111566A (ja) | 2020-07-27 |
TWI841660B (zh) | 2024-05-11 |
US20200216376A1 (en) | 2020-07-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7469046B2 (ja) | メルカプタン、ジスルフィド及びc5炭化水素の存在下でc4炭化水素流から多不飽和炭化水素を除去する方法 | |
TWI727093B (zh) | Lpg或ngl的去氫化及由此獲得之烯烴的彈性利用 | |
JP5298195B2 (ja) | 統合されたプロピレン生成 | |
JP6366587B2 (ja) | ほとんど又は全くエチレンを用いないメタセシスを介するプロピレン | |
KR100230081B1 (ko) | 미정제 고-부타디엔 c4 컷을 선택적으로 수소화시키는 방법 | |
EP1993980A1 (en) | Lowering nitrogen-containing lewis bases in molecular sieve oligomerisation | |
OA10364A (en) | Selective hydrogenationof highly unsaturated compounds in hydrocarbon streams | |
US9260386B2 (en) | Thioetherification of mercaptanes in C4 hydrocarbon mixtures | |
JP5774100B2 (ja) | 多重不飽和炭化水素をオレフィン含有炭化水素混合物において選択的に水素化するための方法 | |
TWI835968B (zh) | 由烴類流中移除硫醇類的催化劑及方法 | |
US9676685B2 (en) | Selective hydrogenation process | |
AU725982B2 (en) | Process for preparing alkyl tert-butyl ethers and di-n-butene from field butanes | |
JPH0148317B2 (ja) | ||
JPS6248637A (ja) | 炭化水素の精製方法 | |
JPH04506360A (ja) | 1,4―ジアシルオキシ―2―ブテンの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20221220 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20231020 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20231024 |
|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20231219 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20240122 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20240326 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20240404 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7469046 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |