JP6705606B2 - 酸化脱水素反応を介したブタジエン製造工程内の吸収溶媒の回収方法 - Google Patents
酸化脱水素反応を介したブタジエン製造工程内の吸収溶媒の回収方法 Download PDFInfo
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 122
- 239000002904 solvent Substances 0.000 title claims description 116
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 title claims description 31
- 238000004519 manufacturing process Methods 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 19
- 238000011084 recovery Methods 0.000 title description 15
- 239000007789 gas Substances 0.000 claims description 74
- 238000010521 absorption reaction Methods 0.000 claims description 71
- 239000000047 product Substances 0.000 claims description 53
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 39
- 239000007795 chemical reaction product Substances 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 12
- 239000001569 carbon dioxide Substances 0.000 claims description 12
- 230000018044 dehydration Effects 0.000 claims description 11
- 238000006297 dehydration reaction Methods 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 description 19
- 239000000203 mixture Substances 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 9
- 208000005156 Dehydration Diseases 0.000 description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 description 9
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000010791 quenching Methods 0.000 description 7
- 230000000171 quenching effect Effects 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 238000007872 degassing Methods 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- BYUANIDVEAKBHT-UHFFFAOYSA-N [Mo].[Bi] Chemical compound [Mo].[Bi] BYUANIDVEAKBHT-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000007670 refining Methods 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 3
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- -1 amide compound Chemical class 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- ZMFDXQTVCRGRNM-XOMXBQTJSA-N (e)-but-2-ene Chemical compound C\C=C\C.C\C=C\C ZMFDXQTVCRGRNM-XOMXBQTJSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- SYRIRLOOSKFSFC-UHFFFAOYSA-N butane Chemical compound CCCC.CCCC SYRIRLOOSKFSFC-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- ZGHDMISTQPRNRG-UHFFFAOYSA-N dimolybdenum Chemical compound [Mo]#[Mo] ZGHDMISTQPRNRG-UHFFFAOYSA-N 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1425—Regeneration of liquid absorbents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1418—Recovery of products
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0488—Flow sheets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1487—Removing organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
- C07C27/26—Purification; Separation; Stabilisation
- C07C27/34—Purification; Separation; Stabilisation by extraction
-
- 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
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
-
- 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
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
-
- 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
- C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
- C07C5/48—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with oxygen as an acceptor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/11—Purification; Separation; Use of additives by absorption, i.e. purification or separation of gaseous hydrocarbons with the aid of liquids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/20405—Monoamines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/20431—Tertiary amines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/70—Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
- B01D2257/702—Hydrocarbons
- B01D2257/7022—Aliphatic hydrocarbons
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1493—Selection of liquid materials for use as absorbents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Gas Separation By Absorption (AREA)
- Treating Waste Gases (AREA)
Description
前述した酸化脱水素反応を介したブタジエンの製造方法を実施するためのブタジエン製造装置は、C4油分、スチーム(steam)、酸素(O2)及び窒素(N2)を含む第1の流れ30の各成分を反応器10内にそれぞれ流入させるための個別パイプラインを含むか、または反応器10と直接連結された一つのパイプラインから分岐され、前記第1の流れに含まれる成分が個別に投入される複数個の個別パイプラインを含むことができる(図1参照)。
先ず、C4油分、スチーム(steam)、酸素(O2)及び窒素(N2)を含む第1の流れ30を反応器内に流入させ、酸化脱水素反応を進めさせる。
C4H8+1/2O2 C4H6+H2O (1)
C4H10+O2 C4H6+2H2O (2)
本発明の一実施形態で、前記反応器から得られる反応生成物は、急冷段階を経ることができる。
本発明の一実施形態で、前記反応器から得られた反応生成物は、水分を除去する脱水段階をさらに含むことができる。
本発明の一実施形態で、前記反応器から得られる反応生成物を溶媒吸収塔で吸収溶媒と接触させ、ブタジエンを含むC4混合物のみ吸収溶媒に選択的に吸収させ、その他のガス生成物(light gas)は分離除去する。
本発明の一実施形態で、前記吸収溶媒内に含まれたブタジエンを含むC4混合物は、精製段階を経て純度の高いブタジエンとして製造される。前記精製段階は、溶媒回収部23、ブタジエン精製部24のうち選択される1つ以上を含むことができる(図1参照)。
前記ガス分離段階で分離されるガス生成物には、溶媒吸収塔で用いられた吸収溶媒のうち一部が含まれることがあり、前記吸収溶媒が第2の流れに含まれて反応器に入る場合、酸化脱水素反応に悪影響を与える。また、前記吸収溶媒が第3の流れに含まれて系外に排出される場合、溶媒吸収塔に吸収溶媒を補充しなければならないので、経済的な損失が発生し得る。
本発明の酸化脱水素反応を介したブタジエンの製造工程において、ガス分離装置から排出されるガス生成物を3段のウォッシュカラム(wash column)に伝達し、吸収溶媒を回収した。このとき、溶媒吸収塔で用いられた吸収溶媒は、ジメチルホルムアミド(DMF)であった。一方、ウォッシュカラムで溶媒として用いられた清水(Fresh Water)の量は1,178kg/hであり、ポンプを用いてウォッシュカラムに持続的に供給した再生水(Recycle Water)の量は30,000kg/hrであった。
前記実施例1と同一の方法でブタジエンを製造したが、ガス生成物の排出時にウォッシュカラムなどで吸収溶媒を回収する工程を進めなかった。
前記実施例1及び比較例1に基づいて溶媒の吸収塔上部のガス生成物を処理した結果、下記表1のような結果を得た。
[項目1]
酸化脱水素反応を介したブタジエンを含む反応生成物を生成する段階;
反応生成物の水分を除去する脱水段階;
脱水段階で脱水された反応生成物を、吸収塔において吸収溶媒と接触させてブタジエンを吸収させる段階;
吸収塔の上部から排出されるガス生成物がウォッシュカラム(wash column)に伝達される段階;及び
ウォッシュカラム内を循環する溶媒がガス生成物に含まれた吸収溶媒を回収する段階;を含むブタジエンの製造方法。
[項目2]
ウォッシュカラム内を循環する溶媒は、極性プロトン溶媒を含む項目1に記載のブタジエンの製造方法。
[項目3]
ウォッシュカラム内を循環する溶媒は、水(H 2 O)である項目1に記載のブタジエンの製造方法。
[項目4]
ウォッシュカラム内を循環する溶媒がガス生成物に含まれた吸収溶媒を回収する段階で、ガス生成物に対する、ウォッシュカラム内を循環させるために新たに投入する溶媒の重量比は、100:0.1〜100:10である項目1から3のいずれか一項に記載のブタジエンの製造方法。
[項目5]
吸収溶媒は、極性非プロトン溶媒(polar aprotic solvent)である項目1から4のいずれか一項に記載のブタジエンの製造方法。
[項目6]
吸収溶媒は、ジメチルホルムアミド(dimethylformamide(DMF))、メチルピロリドン(methylpyrrolidone(NMP))、アセトニトリル(acetonitrile(ACN))、ジメチルアセトアミド(dimethylacetamide(DMA))及びジメチルスルホキシド(dimethyl sulfoxide(DMSO))からなる群より選択される1つまたは2以上の混合物である項目1から5のいずれか一項に記載のブタジエンの製造方法。
[項目7]
酸化脱水素反応を介してブタジエンを含む反応生成物を生成する反応器;
反応生成物の水分を除去する脱水手段;
脱水手段で脱水された反応生成物と吸収溶媒とを接触させてブタジエンを吸収させる溶媒吸収塔;
溶媒吸収塔の上部からガス生成物が伝達される配管;
配管と連結されたウォッシュカラム(wash column);及び
ウォッシュカラムの一側に備えられ、ウォッシュカラムに流入される溶媒を循環させるポンプ;を含むブタジエン製造装置。
[項目8]
ウォッシュカラムは、1段以上のトレイ(tray)タイプまたはパッキング(packing)タイプである項目7に記載のブタジエン製造装置。
Claims (2)
- 反応器で酸化脱水素反応を介したブタジエンを含む反応生成物を生成する段階と;
前記反応生成物の水分を除去する脱水段階と;
前記脱水段階で脱水された反応生成物を、吸収塔において吸収溶媒と接触させてブタジエンを吸収させる段階と;
前記吸収塔の上部から排出されるガス生成物がウォッシュカラム(wash column)に伝達される段階と;
前記ウォッシュカラム内を循環する溶媒が前記ガス生成物に含まれた吸収溶媒を回収する段階と;及び
前記吸収溶媒が除去された前記ガス生成物を内部循環ラインに沿って前記反応器に再投入する段階と;
を含み、
前記ガス生成物は、窒素、水蒸気及び二酸化炭素の少なくとも一つを含み、
前記ウォッシュカラム内を循環する溶媒は、水(H2O)であり、
前記吸収溶媒はジメチルホルムアミド(dimethylformamide(DMF))である、
ブタジエンの製造方法。 - 前記ウォッシュカラム内を循環する溶媒が前記ガス生成物に含まれた吸収溶媒を回収する段階で、ガス生成物に対する、ウォッシュカラム内を循環させるために新たに投入する溶媒の重量比は、100:0.1〜100:10である請求項1に記載のブタジエンの製造方法。
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Family Cites Families (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH406143A (de) * | 1963-12-19 | 1966-01-31 | Sulzer Ag | Stoffaustauschkolonne |
US3539503A (en) | 1968-08-19 | 1970-11-10 | Marathon Oil Co | Simultaneous dual extraction of light and heavy aromatic hydrocarbons from hydrocarbon mixtures |
US3663641A (en) * | 1970-09-18 | 1972-05-16 | Phillips Petroleum Co | Removal of oxygenated compounds from unsaturated hydrocarbons |
JPS4854019A (ja) | 1971-11-17 | 1973-07-30 | ||
DE3043831A1 (de) * | 1980-11-20 | 1982-06-24 | Linde Ag, 6200 Wiesbaden | Verfahren zum entfernen von sauren gasen, insbesondere kohlendioxid, aus gasgemischen |
JPS59167525A (ja) * | 1983-03-14 | 1984-09-21 | Japan Synthetic Rubber Co Ltd | 1,3−ブタジエンの製造方法 |
US6395953B1 (en) * | 1997-03-11 | 2002-05-28 | Nippon Zeon Co., Ltd. | Process for preparing purified conjugated diene |
DE19818810A1 (de) | 1998-04-27 | 1999-10-28 | Basf Ag | Verfahren zum Trennen eines C4-Kohlenwasserstoffgemisches |
KR100410753B1 (ko) | 2001-07-18 | 2003-12-18 | 현대자동차주식회사 | 차량용 엔진의 실화 검출방법 |
JP2003128595A (ja) | 2001-10-25 | 2003-05-08 | Nippon Zeon Co Ltd | 不飽和炭化水素の分離精製方法 |
JP4593264B2 (ja) | 2004-01-30 | 2010-12-08 | 三菱化学エンジニアリング株式会社 | N−メチル−2−ピロリドン回収装置及びその回収方法 |
DE102005002127A1 (de) * | 2005-01-17 | 2006-07-20 | Basf Ag | Verfahren zur Herstellung von Butadien aus n-Butan |
CA2657739A1 (en) * | 2006-07-20 | 2008-01-24 | Basf Se | Process for preparing isopropanol and 2-butanol from the corresponding alkanes |
JP2010275210A (ja) * | 2009-05-27 | 2010-12-09 | Mitsubishi Chemicals Corp | 共役ジエンの製造方法 |
JP5648319B2 (ja) | 2009-05-29 | 2015-01-07 | 三菱化学株式会社 | 共役ジエンの製造方法 |
US8293960B2 (en) | 2009-08-17 | 2012-10-23 | Lummus Technology Inc. | Process for the production of butadiene |
JP5371734B2 (ja) * | 2009-12-25 | 2013-12-18 | 三菱重工業株式会社 | Co2回収装置およびco2回収方法 |
CN201586478U (zh) * | 2009-12-30 | 2010-09-22 | 山东山大能源环境有限公司 | 一种用于大型湿法烟气脱硫的两级循环浆液装置 |
JP2012111751A (ja) | 2010-11-04 | 2012-06-14 | Mitsubishi Chemicals Corp | 共役ジエンの製造方法 |
JP5597260B2 (ja) * | 2010-11-22 | 2014-10-01 | バブコック日立株式会社 | 燃焼排ガス中の二酸化炭素除去装置 |
US8420879B2 (en) * | 2011-03-03 | 2013-04-16 | Basf Se | Process for workup of a stream comprising butene and/or butadiene |
ES2543313T3 (es) * | 2011-03-31 | 2015-08-18 | Basf Se | Retención de aminas en la separación de gases ácidos por medio de agentes de absorción de amina |
US9193647B2 (en) * | 2012-01-30 | 2015-11-24 | Basf Se | Process for preparing butadiene and/or butenes from n-butane |
US20140081062A1 (en) * | 2012-09-20 | 2014-03-20 | Basf Se | Process for the Preparation of Butadiene with Removal of Oxygen from C4-Hydrocarbon Streams |
CN102863309B (zh) * | 2012-09-21 | 2014-04-16 | 湖南百利工程科技股份有限公司 | 一种丁烯氧化脱氢制丁二烯反应生成气处理工艺方法 |
WO2014148323A1 (ja) * | 2013-03-18 | 2014-09-25 | Jsr株式会社 | 1,3-ブタジエンの製造方法 |
EP2981653B1 (en) * | 2013-04-05 | 2017-11-22 | Jon Khachaturian | Method for elevating a marine platform |
KR101704902B1 (ko) * | 2014-06-03 | 2017-02-08 | 주식회사 엘지화학 | 산화탈수소화 반응을 통한 부타디엔의 제조방법 |
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