JP2004285045A - 低ナトリウム開裂生成物 - Google Patents
低ナトリウム開裂生成物 Download PDFInfo
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- JP2004285045A JP2004285045A JP2003387230A JP2003387230A JP2004285045A JP 2004285045 A JP2004285045 A JP 2004285045A JP 2003387230 A JP2003387230 A JP 2003387230A JP 2003387230 A JP2003387230 A JP 2003387230A JP 2004285045 A JP2004285045 A JP 2004285045A
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- 230000007017 scission Effects 0.000 title claims abstract description 71
- 238000003776 cleavage reaction Methods 0.000 title claims abstract description 70
- 239000011734 sodium Substances 0.000 title claims abstract description 50
- 229910052708 sodium Inorganic materials 0.000 title claims abstract description 48
- 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 title claims abstract description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 82
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 78
- 238000000034 method Methods 0.000 claims abstract description 50
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 20
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 19
- 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 claims abstract description 18
- 239000003957 anion exchange resin Substances 0.000 claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 239000003377 acid catalyst Substances 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 239000012458 free base Substances 0.000 claims abstract description 5
- 150000001768 cations Chemical class 0.000 claims description 46
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 44
- 150000001450 anions Chemical class 0.000 claims description 43
- 230000008929 regeneration Effects 0.000 claims description 24
- 238000011069 regeneration method Methods 0.000 claims description 24
- 238000005406 washing Methods 0.000 claims description 22
- 150000002500 ions Chemical class 0.000 claims description 19
- 238000001179 sorption measurement Methods 0.000 claims description 17
- 238000011084 recovery Methods 0.000 claims description 16
- 239000002585 base Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 239000012530 fluid Substances 0.000 claims description 9
- 238000011027 product recovery Methods 0.000 claims description 9
- 238000005349 anion exchange Methods 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 7
- 238000005341 cation exchange Methods 0.000 claims description 7
- 238000004064 recycling Methods 0.000 claims description 6
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 claims description 3
- 230000004931 aggregating effect Effects 0.000 claims description 3
- 230000001172 regenerating effect Effects 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 238000010504 bond cleavage reaction Methods 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 230000003134 recirculating effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 15
- 235000011121 sodium hydroxide Nutrition 0.000 abstract description 10
- 229910001415 sodium ion Inorganic materials 0.000 abstract description 9
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 55
- 239000011347 resin Substances 0.000 description 27
- 229920005989 resin Polymers 0.000 description 27
- 239000000243 solution Substances 0.000 description 18
- 239000006227 byproduct Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 15
- 238000005342 ion exchange Methods 0.000 description 14
- 230000008569 process Effects 0.000 description 12
- 239000007800 oxidant agent Substances 0.000 description 10
- 229920001429 chelating resin Polymers 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000002699 waste material Substances 0.000 description 8
- 239000003456 ion exchange resin Substances 0.000 description 7
- 229920003303 ion-exchange polymer Polymers 0.000 description 7
- 150000007524 organic acids Chemical class 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 239000002351 wastewater Substances 0.000 description 7
- 238000012423 maintenance Methods 0.000 description 6
- 235000005985 organic acids Nutrition 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 5
- 239000003518 caustics Substances 0.000 description 5
- 238000005194 fractionation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- -1 sodium Chemical class 0.000 description 5
- 238000006073 displacement reaction Methods 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229940023913 cation exchange resins Drugs 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012492 regenerant Substances 0.000 description 3
- 238000004065 wastewater treatment Methods 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000010815 organic waste Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- XDTRNDKYILNOAP-UHFFFAOYSA-N phenol;propan-2-one Chemical compound CC(C)=O.OC1=CC=CC=C1 XDTRNDKYILNOAP-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
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- 239000012609 strong anion exchange resin Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
【解決手段】該WCPを水素形状の陽イオン交換樹脂と、そして次に遊離塩基または水酸化物形状の陰イオン交換樹脂と接触させて、本質的にナトリウムイオンの無いWCPを製造する。該陽イオンおよび陰イオン交換樹脂は、夫々酸および苛性ソーダで再生する。該処理により、新規なおよび既存のフェノール方法の生産性および産物の性質が改良される。
Description
図1は、クメン流(10)からフェノールを製造する方法を説明するものであり、クメンヒドロペルオキシド濃縮器(20)、クメンヒドロペルオキシドへのクメン酸化器(30)、フェノールおよびアセトンの混合物へのクメンヒドロペルオキシド開裂(40)、一種以上のアルカリ性溶液を用いた洗浄(50)、塩を除去するためのイオン交換(60)、アセトン回収(70)、フェノール蒸留(80)、および廃水からのフェノール除去(90)を含んでいる。
表1は、本発明によるイオン除去を試験するために合成された模擬の洗浄開裂生成物の組成を示す。工業的フェノールプロセスシステムは、凝集剤なしで、約25〜30ppmwの範囲のナトリウム濃度を有するWCPを製造することが出来る。しかし、より高い値は珍しくなく、この場合は61ppmwのナトリウムイオン濃度を示している。凝集はナトリウム濃度を20ppmwまたはそれよりわずかに低く減少させることが出来る。表1のWCP組成は、イオン交換装置への可能なWCP供給物を例示する。この組成は、下記の実施例2〜3で報告する試験で使用した。
4種の陽イオン交換樹脂をバッチ式撹拌反応器で試験しWCPからナトリウムイオンを吸着する樹脂能力を測定した。該試験は、スルホン化架橋スチレン−ジビニルベンゼン共重合体に基づく陽イオン高度架橋樹脂を使用した。各々の典型的な性質を表2に示してある。
次に、2床交換装置を用いた連続流カラム試験において、実施例2の樹脂に対して、WCP中のナトリウムおよび硫酸イオンに対するイオン交換吸着速度および能力を測定した。実施例1の合成WCPを直列の2個の床にポンプで通過させた。試験の床は、1/2インチ直径のステンレススチール管を用いて組立て、サーモスタット制御の油浴に浸漬して操作温度を約50℃に維持した。第一の床は上記実施例2の陽イオンC4樹脂を保持し、第二の床は遊離塩基形のゲル型アクリル系弱塩基陰イオン交換樹脂(陰イオンA1)を使用した。上記表2で報告した陽イオン樹脂の性質に対応して、陰イオンA1樹脂は5.98eq/kgおよび1.66eq/Lという典型的な陰イオン交換能力と60重量パーセントの湿分保持能力を有していた。
37.5BV/hのWCP流速を用いて、市販のWCPで、更に一連の試験を行った。陽イオンC4および陰イオンA1を用いて、新鮮な(新しい)樹脂をカラムに充填した。この試験に際しては、サンプルの分析はイオン-クロマトグラフィ/質量分析法を用いて行い、市販のWCPでは59ppmwの平均ナトリウム濃度を示した。
20 クメンヒドロペルオキシド濃縮器
30 クメン酸化器
40 クメンヒドロペルオキシド開裂
50 洗浄
60 イオン交換
70 アセトン回収
80 フェノール蒸留
90 廃水からのフェノール除去
102 陽イオン交換樹脂床
104 WCP流;陰イオン交換樹脂床
106 陽イオン装置
112 WCP流出物
114 陰イオン装置
120 生成物回収ライン
132 フェノール性水捕集タンク
134 硫酸
146 水酸化ナトリウム(苛性)溶液
202 陽イオン交換床
204 陰イオン交換床
208 穴のあいた支持板
210 不活性樹脂層
200a 交換体
200b 交換体
202 WCP供給物ライン
204 精製WCP流出物ライン
220 再生剤およびフラッシング流体
Claims (25)
- 酸触媒を用いたクメンヒドロペルオキシドの反応からの洗浄開裂生成物のイオン含量を減少させる方法において、
該洗浄開裂生成物を陽イオン交換体と接触させてナトリウムを含む正帯電イオンを除去すること、
該洗浄開裂生成物を陰イオン交換体と接触させて硫酸イオンを含む負帯電イオンを除去すること、及び
ナトリウム及び硫酸イオンの少ない交換体流出物を回収すること、
を含む上記方法。 - 該洗浄開裂生成物が全洗浄開裂生成物を含む、請求項1記載の方法。
- 該洗浄開裂生成物が脱水開裂生成物を含む、請求項1記載の方法。
- 該洗浄開裂生成物が、
0.8〜1.5のアセトン対フェノールのモル比、
2〜30重量パーセントのクメン、
4〜20重量パーセントの水、および
10〜400ppmwのナトリウム
を含む、請求項1記載の方法。 - 該陽イオン交換体が水素形態の強酸陽イオン交換樹脂を含む、請求項1記載の方法。
- 該陽イオン交換体が水素形態の弱酸陽イオン交換樹脂を含む、請求項1記載の方法。
- 該陰イオン交換体が遊離塩基形態の弱塩基陰イオン交換樹脂を含む、請求項1記載の方法。
- 該陰イオン交換体が水酸化物形態の強塩基陰イオン交換樹脂を含む、請求項1記載の方法。
- 該陰イオンおよび陽イオン交換体との接触が、該洗浄開裂生成物を陽イオンおよび陰イオン交換体の両方を含む交換体媒体の混合床に通すことを含む、請求項1記載の方法。
- 該流出物が10ppmw未満のナトリウム濃度を有する、請求項9記載の方法。
- 該陽イオンおよび陰イオン交換体が夫々陽イオンおよび陰イオン交換樹脂の直列床を含む、請求項1記載の方法。
- 該陽イオン床流出物が10ppmw未満のナトリウム濃度および3.5〜6.0のpHを有する、請求項1記載の方法。
- 20〜80℃の温度および1〜60BV/hの供給速度における陽イオン交換吸着サイクルを含む、請求項1記載の方法。
- 0.5〜10重量パーセントの硫酸水溶液を用いた陽イオン交換再生サイクルを含む、請求項13記載の方法。
- 20〜80℃の温度および1〜60BV/hの供給速度における陰イオン交換吸着サイクルを含む、請求項1記載の方法。
- NaOH濃度またはNaOH相当濃度が0.2〜8重量パーセントのNaOH水溶液、ナトリウムフェノキシド水溶液、またはそれらの組合せを用いた陰イオン交換再生サイクルを含む、請求項15記載の方法。
- フェノールの製造方法において、
クメンをクメンヒドロペルオキシドに酸化すること、
該クメンヒドロペルオキシドを酸触媒の存在下開裂してフェノールおよびアセトンを含む開裂生成物混合物を形成すること、
該開裂生成物混合物をアルカリ性洗浄溶液で洗浄して洗浄開裂生成物を形成すること、
該洗浄開裂生成物を陽イオン交換体および陰イオン交換体と接触させてイオン含量の減少した精製開裂生成物を形成すること、及び
該精製開裂生成物からフェノールおよびアセトンを回収すること、
を含む上記方法。 - 該陽イオン交換体が強酸陽イオン交換樹脂および弱酸陽イオン交換樹脂から選択される水素形態の陽イオン交換樹脂を含み、該陰イオン交換体が遊離塩基形態の弱塩基陰イオン交換樹脂および水酸化物形態の強塩基陰イオン交換樹脂から選択される陰イオン交換樹脂を含む、請求項17記載の方法。
- 該精製開裂生成物が10ppmw未満のナトリウムを含有する、請求項17記載の方法。
- 該精製開裂生成物が2ppmw未満のナトリウムを含有する、請求項17記載の方法。
- 該洗浄開裂生成物が、0.8〜1.5のアセトン対フェノールのモル比、2〜30重量パーセントのクメン、4〜20重量パーセントの水、および10〜400ppmwのナトリウムを含む、請求項17記載の方法。
- 該洗浄が、全洗浄開裂生成物を凝集させて該洗浄開裂生成物から水を除去して該イオン交換体と接触させることを含む、請求項21記載の方法。
- 該生成物回収が、該精製開裂生成物の蒸留および水性流の回収を含み、該方法が該水性流を該洗浄工程に再循環させることを更に含む、請求項21記載の方法。
- 該洗浄からの使用済洗浄水からフェノールを除去することを更に含む、請求項21記載の方法。
- 該陽イオンおよび陰イオン交換体を水性および有機流体で再生させること、使用済水性流体を該フェノール除去に再循環させること、及び使用済有機流体を該開裂生成物洗浄または該フェノールおよびアセトン回収に再循環させること、を更に含む請求項24記載の方法。
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JP2015178476A (ja) * | 2014-03-19 | 2015-10-08 | 三菱化学株式会社 | フェノールの製造方法 |
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US7692046B2 (en) | 2007-06-21 | 2010-04-06 | Exxonmobil Chemical Patents Inc. | Heterogeneous arylalkyl oxidation promoter |
CN104080763B (zh) * | 2011-09-19 | 2016-08-24 | 凯洛格·布朗及鲁特有限公司 | 联产低甲醇含量的丙酮的方法和系统 |
US8865957B2 (en) * | 2012-03-09 | 2014-10-21 | Honeywell Intenational Inc. | Method for producing alpha-methyl styrene from cumene |
US9193652B2 (en) * | 2014-03-04 | 2015-11-24 | Kellogg Brown & Root Llc | Phenol resin treatment improvement |
US11148987B2 (en) * | 2017-08-23 | 2021-10-19 | Shell Oil Company | Method of treating a neutralized aralkyl hydroperoxide cleavage stream |
CN114436739A (zh) * | 2020-10-16 | 2022-05-06 | 中国石油化工股份有限公司 | 一种制备异丙苯的方法及得到的异丙苯 |
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EP1411040B1 (en) | 2010-07-21 |
BR0304274A (pt) | 2004-08-31 |
ES2347226T3 (es) | 2010-10-27 |
CN1548410A (zh) | 2004-11-24 |
EP1411040A1 (en) | 2004-04-21 |
KR100973452B1 (ko) | 2010-08-02 |
DE60333425D1 (de) | 2010-09-02 |
US20040106831A1 (en) | 2004-06-03 |
TW200409748A (en) | 2004-06-16 |
JP4648621B2 (ja) | 2011-03-09 |
US6825387B2 (en) | 2004-11-30 |
TWI247000B (en) | 2006-01-11 |
BR0304274B1 (pt) | 2013-04-30 |
CN100509731C (zh) | 2009-07-08 |
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