JP5746057B2 - 芳香族化合物を含有する炭化水素留分から純粋な芳香族化合物を取得する方法 - Google Patents
芳香族化合物を含有する炭化水素留分から純粋な芳香族化合物を取得する方法 Download PDFInfo
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- 150000001491 aromatic compounds Chemical class 0.000 title claims description 125
- 238000000034 method Methods 0.000 title claims description 106
- 229930195733 hydrocarbon Natural products 0.000 title claims description 52
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 52
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 49
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 132
- 238000000895 extractive distillation Methods 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 70
- 239000003502 gasoline Substances 0.000 claims description 49
- 239000000047 product Substances 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
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- 238000000605 extraction Methods 0.000 claims description 30
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- 238000005984 hydrogenation reaction Methods 0.000 claims description 25
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 24
- 238000004821 distillation Methods 0.000 claims description 23
- 238000006900 dealkylation reaction Methods 0.000 claims description 18
- 230000020335 dealkylation Effects 0.000 claims description 17
- 238000000746 purification Methods 0.000 claims description 15
- 239000000571 coke Substances 0.000 claims description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 9
- 238000000197 pyrolysis Methods 0.000 claims description 8
- 238000011084 recovery Methods 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- -1 alkylene glycol Chemical compound 0.000 claims description 7
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical group O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 238000004508 fractional distillation Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- PPDFQRAASCRJAH-UHFFFAOYSA-N 2-methylthiolane 1,1-dioxide Chemical compound CC1CCCS1(=O)=O PPDFQRAASCRJAH-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 150000001336 alkenes Chemical class 0.000 description 14
- 239000007789 gas Substances 0.000 description 14
- 238000009835 boiling Methods 0.000 description 13
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- 150000001875 compounds Chemical class 0.000 description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 150000001993 dienes Chemical class 0.000 description 7
- 150000001555 benzenes Chemical class 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
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- 238000000926 separation method Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004517 catalytic hydrocracking Methods 0.000 description 2
- 238000001833 catalytic reforming Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
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- 230000002378 acidificating effect Effects 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
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- 230000023556 desulfurization Effects 0.000 description 1
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- 125000001827 mesitylenyl group Chemical class [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
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- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
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- 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
- C10G7/00—Distillation of hydrocarbon oils
- C10G7/08—Azeotropic or extractive distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/141—Fractional distillation or use of a fractionation or rectification column where at least one distillation column contains at least one dividing wall
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/06—Toluene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
- C07C4/12—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene
- C07C4/14—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene splitting taking place at an aromatic-aliphatic bond
- C07C4/18—Catalytic processes
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- 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
- C10G45/58—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins
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- 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
- C10G47/00—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions
- C10G47/02—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions characterised by the catalyst used
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- 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
- C10G47/00—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions
- C10G47/22—Non-catalytic cracking in the presence of hydrogen
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1096—Aromatics or polyaromatics
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- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
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- 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
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/30—Aromatics
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Description
・芳香族化合物リッチな出発炭化水素混合物をまず抽出蒸留にかけ、そこで、適切な抽出溶媒を用いて芳香族化合物含有の炭化水素混合物を蒸留し、溶媒を除去して、芳香族炭化水素が著しく低減された溶媒不含の生成物流と、芳香族炭化水素が著しく富化された溶媒不含の芳香族化合物濃縮物とを得、
・抽出蒸留後の溶媒不含の芳香族化合物濃縮物を、水素化脱アルキル用の反応器に供給し、そこで水素と反応させ、その際に、主生成物としての脱アルキル芳香族化合物流ならびに副生成物としてのパラフィン系炭化水素流およびメタン流が形成され、
・芳香族炭化水素流を、浄化ユニットに供給し、
・抽出蒸留および抽出溶媒の回収をただ1つの塔の中で行う方法を請求する。
・抽出蒸留用の塔と、生じた芳香族化合物濃縮物を水素化するための反応器と、生じた芳香族生成物を浄化するための精製ユニットとを備え、
・プロセスフローにおいて順次、炭化水素含有混合物からの芳香族炭化水素の抽出蒸留、芳香族生成物流からの抽出溶媒の除去、脱アルキル芳香族生成物を得るための芳香族化合物の水素化脱アルキル、および得られた芳香族生成物の浄化が行われるように、抽出蒸留用の塔、水素化反応器および精製ユニットが配置され、
・装置が、抽出蒸留および抽出溶媒の回収をただ1つの塔の中で可能とする塔を含む、
装置が請求される。
・塔主要区画の下にある蒸留分離部と、塔主要区画の上にある濃縮部と、2つの並列する室からなる塔主要区画と、底部ヒータを備えた塔底部とを有し、
・塔主要区画の一方の室は、上側および下側が塔内部に対して開いており、他方の室は、上側が塔内部に対して閉じ、下側が塔内部に対して開いており、全ての室は、物質交換を改善するための内装物を含み、上側が塔内部に対して閉じ、下側が塔内部に対して開いている室の内装物の上方に、抽出剤不含の生成物を蒸気の形態で取り出し、液化された生成物部分流を還流させるための設備が存在している装置も請求される。
86質量パーセントの芳香族化合物含有率を有する完全水素化熱分解ガソリン由来の芳香族化合物を含有する炭化水素混合物を抽出蒸留にかけるが、その際、ドイツ特許出願公開第19849651A1号(特許文献6)に挙げられている装置および抽出溶媒としてN−ホルミルモルホリンを使用する。抽出蒸留前の芳香族化合物を含有する出発混合物の組成と、抽出蒸留後の芳香族化合物濃縮物の組成とを表1に記載する。これらの組成は、留分のガスクロマトグラフィー分析により決定した。抽出蒸留に続いて、水素化脱アルキルを実施するが、その際、抽出蒸留から得られた混合物を、水素化脱アルキル用の装置部分で、水素と反応させる。そうすると、芳香族化合物を含有する脱アルキル生成物が得られる。
2 蒸留塔
2a 低沸点の芳香族化合物留分
2b 高沸点の芳香族化合物留分
2c 分離を改善するための装置
2d リボイラー
2e 中間容器
2f 圧縮機
2g 中間ヒータ
3 抽出蒸留用の塔
3a オレフィンリッチな炭化水素混合物
3b オレフィンが少ない芳香族化合物濃縮物
3c 熱交換機
3d 抽出蒸留塔の2つの室
3e 循環抽出溶媒
3f 熱交換機
3g 熱交換機
3h 圧縮機
3i リボイラー
3j 中間容器
3k 圧縮機
3l 収集容器
3m 真空ポンプ
3n 中間容器
4a 蒸発器
4b 予備処理反応器
4c 脱アルキル反応器
4c’ 脱アルキル反応器
4d 水素分離器
4e 後処理塔
4e’ 後処理塔
4f 蒸留塔
4g メタンおよび水素の排出
4h 圧縮機
4i 中間容器
4j 純ベンゼンの排出
Claims (17)
- C7〜C9芳香族化合物リッチな炭化水素混合物を脱アルキルする方法であって、
前記芳香族化合物リッチな出発炭化水素混合物をまず、抽出蒸留にかけ、そこで、前記芳香族化合物を含有する炭化水素混合物を適切な抽出溶媒を用いて蒸留し、前記抽出溶媒を除去し、その際に芳香族炭化水素が著しく貧化された溶媒不含の生成物流と、芳香族炭化水素が著しく富化された溶媒不含の芳香族化合物濃縮物とが得られる方法において、
前記溶媒不含の芳香族化合物濃縮物を、前記抽出蒸留の後に、水素化脱アルキル用の反応器に供給し、そこで、水素と反応させ、その際に主生成物としての脱アルキル芳香族化合物流ならびに副生成物としてのメタン流を生じさせること、
前記脱アルキル芳香族化合物流が、浄化ユニットに供給されること、および
前記抽出蒸留および前記抽出溶媒の回収がただ1つの塔の中で行われること、
を特徴とする方法。 - 前記浄化ユニットが分留であることを特徴とする、請求項1に記載の方法。
- 前記浄化ユニットが、「フラッシュ」蒸留段階であることを特徴とする、請求項1に記載の方法。
- 前記芳香族化合物を含有する出発材料が、完全水素化熱分解ガソリンであることを特徴とする、請求項1〜3のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記芳香族化合物を含有する出発材料が、接触改質ガソリンであることを特徴とする、請求項1〜3のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記芳香族化合物を含有する出発材料が、加圧精製コークス炉ベンゼンであることを特徴とする、請求項1〜3のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記の脱アルキルされ浄化された芳香族化合物流が、純ベンゼンであることを特徴とする、請求項1〜6のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記芳香族化合物を含有する出発材料が、前記抽出蒸留に供する前に、蒸留塔で分留されることを特徴とする、請求項1〜7のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記芳香族化合物を含有する出発材料が、前記抽出蒸留に供する前に、水、酸、適切な溶媒またはこれらの物質の混合物と接触させられることを特徴とする、請求項1〜8のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記芳香族化合物を含有する出発材料が、前記抽出蒸留に供する前に、水素化にかけられることを特徴とする、請求項1〜9のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記抽出蒸留プロセスステップと前記水素化脱アルキルプロセスステップの間に、水素化が実施されることを特徴とする、請求項1〜9のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記抽出溶媒が、置換基中に1〜8個の炭素原子を有するN−置換溶媒であることを特徴とする、請求項1〜11のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記抽出溶媒が、N−ホルミルモルホリンであることを特徴とする、請求項1〜11のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記抽出蒸留のための前記抽出溶媒が、N−メチルピロリドン、スルホラン、メチルスルホラン、アルキレングリコールもしくはアルキル化アルキレングリコールまたはこれらの物質の混合物であることを特徴とする、請求項1〜11のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記抽出蒸留のための前記抽出溶媒混合物が水を含有することを特徴とする、請求項12〜14のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記水素化脱アルキル用の前記水素化ステップが、熱プロセスであることを特徴とする、請求項1〜15のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
- 前記水素化脱アルキル用の前記水素化ステップが、触媒プロセスであることを特徴とする、請求項1〜15のいずれか一つに記載の芳香族化合物リッチな炭化水素混合物の脱アルキル方法。
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DE102009012265.6 | 2009-03-11 | ||
PCT/EP2010/001024 WO2010102712A2 (de) | 2009-03-11 | 2010-02-18 | Verfahren zur gewinnung von reinaromaten aus aromatenhaltigen kohlenwasserstofffraktionen |
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