TWI770262B - 過氧化氫之製造方法 - Google Patents

過氧化氫之製造方法 Download PDF

Info

Publication number: TWI770262B
Authority: TW; Taiwan
Prior art keywords: working solution; hydrogen peroxide; distillation; tank; regeneration
Prior art date: 2017-09-08

Application number

TW107130762A

Other languages

English (en)

Chinese (zh)

Other versions

TW201912567A (zh

Inventor

松本倫太朗

池田英俊

茂田耕平

Original Assignee

日商三菱瓦斯化學股份有限公司

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.)

2017-09-08

Filing date

2018-09-03

Publication date

2022-07-11

2018-09-03 Application filed by 日商三菱瓦斯化學股份有限公司 filed Critical 日商三菱瓦斯化學股份有限公司

2019-04-01 Publication of TW201912567A publication Critical patent/TW201912567A/zh

2022-07-11 Application granted granted Critical

2022-07-11 Publication of TWI770262B publication Critical patent/TWI770262B/zh

Links

MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 327
238000004519 manufacturing process Methods 0.000 title claims abstract description 97
239000012224 working solution Substances 0.000 claims abstract description 326
238000004821 distillation Methods 0.000 claims abstract description 266
230000008929 regeneration Effects 0.000 claims abstract description 148
238000011069 regeneration method Methods 0.000 claims abstract description 148
150000004056 anthraquinones Chemical class 0.000 claims abstract description 120
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 78
YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 claims abstract description 65
150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 42
238000005406 washing Methods 0.000 claims abstract description 41
239000000126 substance Substances 0.000 claims abstract description 32
238000004064 recycling Methods 0.000 claims abstract description 30
238000000605 extraction Methods 0.000 claims abstract description 22
238000001953 recrystallisation Methods 0.000 claims description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
239000002904 solvent Substances 0.000 claims description 45
-1 alkyl anthraquinone Chemical class 0.000 claims description 35
239000000203 mixture Substances 0.000 claims description 35
238000002360 preparation method Methods 0.000 claims description 34
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 33
238000007254 oxidation reaction Methods 0.000 claims description 26
230000003647 oxidation Effects 0.000 claims description 25
239000003513 alkali Substances 0.000 claims description 23
239000007788 liquid Substances 0.000 claims description 18
239000002699 waste material Substances 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 11
230000001590 oxidative effect Effects 0.000 claims description 10
239000007800 oxidant agent Substances 0.000 claims description 9
239000012670 alkaline solution Substances 0.000 claims description 8
238000011084 recovery Methods 0.000 claims description 6
230000001172 regenerating effect Effects 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 5
238000000034 method Methods 0.000 abstract description 28
238000004140 cleaning Methods 0.000 description 23
230000000694 effects Effects 0.000 description 21
239000001257 hydrogen Substances 0.000 description 18
229910052739 hydrogen Inorganic materials 0.000 description 18
239000002798 polar solvent Substances 0.000 description 18
239000007864 aqueous solution Substances 0.000 description 15
239000003054 catalyst Substances 0.000 description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
239000006227 byproduct Substances 0.000 description 13
238000012546 transfer Methods 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
OTBHDFWQZHPNPU-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1CCCC2 OTBHDFWQZHPNPU-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
239000000047 product Substances 0.000 description 6
RKMPHYRYSONWOL-UHFFFAOYSA-N 1-ethyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(CC)CCC2 RKMPHYRYSONWOL-UHFFFAOYSA-N 0.000 description 5
HSKPJQYAHCKJQC-UHFFFAOYSA-N 1-ethylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CC HSKPJQYAHCKJQC-UHFFFAOYSA-N 0.000 description 5
239000000463 material Substances 0.000 description 5
SNDGLCYYBKJSOT-UHFFFAOYSA-N 1,1,3,3-tetrabutylurea Chemical compound CCCCN(CCCC)C(=O)N(CCCC)CCCC SNDGLCYYBKJSOT-UHFFFAOYSA-N 0.000 description 4
LZNGSHFBWBKBFH-UHFFFAOYSA-N 1-pentyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(CCCCC)CCC2 LZNGSHFBWBKBFH-UHFFFAOYSA-N 0.000 description 4
INPHIYULSHLAHR-UHFFFAOYSA-N 1-pentylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CCCCC INPHIYULSHLAHR-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
238000002156 mixing Methods 0.000 description 4
SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
230000005587 bubbling Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
230000007423 decrease Effects 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
230000014759 maintenance of location Effects 0.000 description 3
IMXBRVLCKXGWSS-UHFFFAOYSA-N methyl 2-cyclohexylacetate Chemical compound COC(=O)CC1CCCCC1 IMXBRVLCKXGWSS-UHFFFAOYSA-N 0.000 description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
RBGUKBSLNOTVCD-UHFFFAOYSA-N 1-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C RBGUKBSLNOTVCD-UHFFFAOYSA-N 0.000 description 2
JORLUGVBYJSSAW-UHFFFAOYSA-N 2-ethyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1CC(CC)CC2 JORLUGVBYJSSAW-UHFFFAOYSA-N 0.000 description 2
SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 2
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HXQPUEQDBSPXTE-UHFFFAOYSA-N Diisobutylcarbinol Chemical compound CC(C)CC(O)CC(C)C HXQPUEQDBSPXTE-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000008901 benefit Effects 0.000 description 2
239000007844 bleaching agent Substances 0.000 description 2
229910021538 borax Inorganic materials 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical class CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000010586 diagram Methods 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
QOSATHPSBFQAML-UHFFFAOYSA-N hydrogen peroxide;hydrate Chemical compound O.OO QOSATHPSBFQAML-UHFFFAOYSA-N 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
239000000178 monomer Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012454 non-polar solvent Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000004065 semiconductor Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
235000010339 sodium tetraborate Nutrition 0.000 description 2
238000003860 storage Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 2
PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 0.000 description 1
GNRPVZNNVOGXHD-UHFFFAOYSA-N 1,2-dimethylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(C)C(C)=CC=C3C(=O)C2=C1 GNRPVZNNVOGXHD-UHFFFAOYSA-N 0.000 description 1
NJMCYPCKTIZMIZ-UHFFFAOYSA-N 1-butyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(CCCC)CCC2 NJMCYPCKTIZMIZ-UHFFFAOYSA-N 0.000 description 1
BVEIKFLZWBDLJG-UHFFFAOYSA-N 1-butylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CCCC BVEIKFLZWBDLJG-UHFFFAOYSA-N 0.000 description 1
JQLVCHDTPJYDIN-UHFFFAOYSA-N 1-methyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(C)CCC2 JQLVCHDTPJYDIN-UHFFFAOYSA-N 0.000 description 1
JMAKRFSLJOYECP-UHFFFAOYSA-N 1-propyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound C(CC)C1CCCC=2C(C3=CC=CC=C3C(C12)=O)=O JMAKRFSLJOYECP-UHFFFAOYSA-N 0.000 description 1
QDQRAKVTIKNTPJ-UHFFFAOYSA-N 1-propylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CCC QDQRAKVTIKNTPJ-UHFFFAOYSA-N 0.000 description 1
ZRYMONUIRTWHAP-UHFFFAOYSA-N 2,7-dimethyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC(C)=CC=C2C(=O)C2=C1CC(C)CC2 ZRYMONUIRTWHAP-UHFFFAOYSA-N 0.000 description 1
RATJDSXPVPAWJJ-UHFFFAOYSA-N 2,7-dimethylanthracene-9,10-dione Chemical compound C1=C(C)C=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 RATJDSXPVPAWJJ-UHFFFAOYSA-N 0.000 description 1
LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical compound CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-UHFFFAOYSA-N 0.000 description 1
WJCQJHNUBJYFBW-UHFFFAOYSA-N 2-methyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1CC(C)CC2 WJCQJHNUBJYFBW-UHFFFAOYSA-N 0.000 description 1
JBIIAJUNHWBZRG-UHFFFAOYSA-N 2-propan-2-yl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1CC(C(C)C)CC2 JBIIAJUNHWBZRG-UHFFFAOYSA-N 0.000 description 1
BQUNPXRABCSKJZ-UHFFFAOYSA-N 2-propan-2-ylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3C(=O)C2=C1 BQUNPXRABCSKJZ-UHFFFAOYSA-N 0.000 description 1
GRVQOVOAEKOZNN-UHFFFAOYSA-N 2-propyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound C(CC)C1CC=2C(C3=CC=CC=C3C(C2CC1)=O)=O GRVQOVOAEKOZNN-UHFFFAOYSA-N 0.000 description 1
ZPQUFYIADDJOEF-UHFFFAOYSA-N 2-propylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CCC)=CC=C3C(=O)C2=C1 ZPQUFYIADDJOEF-UHFFFAOYSA-N 0.000 description 1
RONQEQAXCQKPRV-UHFFFAOYSA-N 2-tert-butyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1CC(C(C)(C)C)CC2 RONQEQAXCQKPRV-UHFFFAOYSA-N 0.000 description 1
YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 description 1
AGWLDLJEVPKXBR-UHFFFAOYSA-N 4,4-dimethyl-2,3-dihydro-1H-anthracene-9,10-dione Chemical compound CC1(CCCC=2C(C3=CC=CC=C3C(C12)=O)=O)C AGWLDLJEVPKXBR-UHFFFAOYSA-N 0.000 description 1
241000208340 Araliaceae Species 0.000 description 1
ZAEWSHNGMAWPSG-UHFFFAOYSA-N C(CCC)C=1C(C(C=2C(C3=CC=CC=C3C(C2C1)=O)=O)=O)=O Chemical class C(CCC)C=1C(C(C=2C(C3=CC=CC=C3C(C2C1)=O)=O)=O)=O ZAEWSHNGMAWPSG-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229910000881 Cu alloy Inorganic materials 0.000 description 1
208000005156 Dehydration Diseases 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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
235000003140 Panax quinquefolius Nutrition 0.000 description 1
229920001131 Pulp (paper) Polymers 0.000 description 1
239000004115 Sodium Silicate Substances 0.000 description 1
XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
229920002522 Wood fibre Polymers 0.000 description 1
AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
239000011149 active material Substances 0.000 description 1
239000005456 alcohol based solvent Substances 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
XAIKOVRFTSBNNU-UHFFFAOYSA-N anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 XAIKOVRFTSBNNU-UHFFFAOYSA-N 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
238000000998 batch distillation Methods 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001944 continuous distillation Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
235000019797 dipotassium phosphate Nutrition 0.000 description 1
IOUCSUBTZWXKTA-UHFFFAOYSA-N dipotassium;dioxido(oxo)tin Chemical compound [K+].[K+].[O-][Sn]([O-])=O IOUCSUBTZWXKTA-UHFFFAOYSA-N 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
TVQLLNFANZSCGY-UHFFFAOYSA-N disodium;dioxido(oxo)tin Chemical compound [Na+].[Na+].[O-][Sn]([O-])=O TVQLLNFANZSCGY-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
ZJQPLBFKBQYYIO-UHFFFAOYSA-N dodecasodium;trisilicate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] ZJQPLBFKBQYYIO-UHFFFAOYSA-N 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
238000005530 etching Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
235000008434 ginseng Nutrition 0.000 description 1
PMYUVOOOQDGQNW-UHFFFAOYSA-N hexasodium;trioxido(trioxidosilyloxy)silane Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-][Si]([O-])([O-])O[Si]([O-])([O-])[O-] PMYUVOOOQDGQNW-UHFFFAOYSA-N 0.000 description 1
230000033444 hydroxylation Effects 0.000 description 1
238000005805 hydroxylation reaction Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000005192 partition Methods 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
238000005502 peroxidation Methods 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
230000037081 physical activity Effects 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000005498 polishing Methods 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
235000010289 potassium nitrite Nutrition 0.000 description 1
239000004304 potassium nitrite Substances 0.000 description 1
ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
238000001223 reverse osmosis Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
229940079864 sodium stannate Drugs 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
239000000243 solution Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
239000010409 thin film Substances 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000003809 water extraction Methods 0.000 description 1

Images

Classifications

- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
- C01B15/01—Hydrogen peroxide
- C01B15/022—Preparation from organic compounds
- C01B15/023—Preparation from organic compounds by the alkyl-anthraquinone process
- 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
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
- C01B15/01—Hydrogen peroxide
- C01B15/013—Separation; Purification; Concentration
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes

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Organic Chemistry (AREA)
Inorganic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Detergent Compositions (AREA)

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WO2024059990A1 (en) *	2022-09-20	2024-03-28	The University Of British Columbia	Methods and apparatus for indirect production of hydrogen peroxide using amyl-anthraquinone for hydrogen transport

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JP6972802B2 (ja)	2021-11-24
CN117105178A (zh)	2023-11-24
JP2019048740A (ja)	2019-03-28
CN109467056A (zh)	2019-03-15
TW201912567A (zh)	2019-04-01
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Publication	Publication Date	Title
TWI770262B (zh)	2022-07-11	過氧化氫之製造方法
TW473455B (en)	2002-01-21	Process and plant for manufacturing an aqueous hydrogen peroxide solution, and aqueous hydrogen peroxide solution
TWI383951B (zh)	2013-02-01	包含動作溶液之再生步驟的過氧化氫之製造方法
TWI758411B (zh)	2022-03-21	利用蒽醌法的過氧化氫製造方法及製造系統
JP7322363B2 (ja)	2023-08-08	過酸化水素水溶液の製造方法
KR102242074B1 (ko)	2021-04-19	과산화수소 제조에 사용되는 작동 용액의 재생 방법, 및 재생한 작동 용액을 사용한 과산화수소의 제조 방법
TWI749170B (zh)	2021-12-11	過氧化氫之製造方法
CN109467057B (zh)	2023-05-05	制造过氧化氢时使用的工作溶液的制备方法
TWI828798B (zh)	2024-01-11	工作溶液之處理方法
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