CN102924349A - 一种制备双(4-叔丁基苄基)硫醚产品的方法 - Google Patents
一种制备双(4-叔丁基苄基)硫醚产品的方法 Download PDFInfo
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- CN102924349A CN102924349A CN201210429384XA CN201210429384A CN102924349A CN 102924349 A CN102924349 A CN 102924349A CN 201210429384X A CN201210429384X A CN 201210429384XA CN 201210429384 A CN201210429384 A CN 201210429384A CN 102924349 A CN102924349 A CN 102924349A
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- tertiary butyl
- benzyl
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- PHGBHAQICGAYLF-UHFFFAOYSA-N 1-tert-butyl-4-[(4-tert-butylphenyl)methylsulfanylmethyl]benzene Chemical compound C(C)(C)(C)C1=CC=C(CSCC2=CC=C(C=C2)C(C)(C)C)C=C1 PHGBHAQICGAYLF-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 73
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 26
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 25
- 239000002994 raw material Substances 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 229910052979 sodium sulfide Inorganic materials 0.000 claims abstract description 12
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000035484 reaction time Effects 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 42
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 42
- 238000005660 chlorination reaction Methods 0.000 claims description 41
- -1 polyoxyethylene nonylphenol Polymers 0.000 claims description 36
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 30
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 25
- 238000003756 stirring Methods 0.000 claims description 18
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 15
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 15
- 238000009413 insulation Methods 0.000 claims description 15
- 239000013078 crystal Substances 0.000 claims description 14
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 13
- 238000005406 washing Methods 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 12
- 235000010265 sodium sulphite Nutrition 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims description 7
- RNMDNPCBIKJCQP-UHFFFAOYSA-N 5-nonyl-7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-ol Chemical compound C(CCCCCCCC)C1=C2C(=C(C=C1)O)O2 RNMDNPCBIKJCQP-UHFFFAOYSA-N 0.000 claims description 7
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 7
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 5
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000003963 antioxidant agent Substances 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 4
- WAXIFMGAKWIFDQ-UHFFFAOYSA-N 1-tert-butyl-4-(chloromethyl)benzene Chemical compound CC(C)(C)C1=CC=C(CCl)C=C1 WAXIFMGAKWIFDQ-UHFFFAOYSA-N 0.000 abstract 4
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000000047 product Substances 0.000 description 72
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 235000019441 ethanol Nutrition 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 150000003568 thioethers Chemical class 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000001035 drying Methods 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 12
- 229960004756 ethanol Drugs 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000012065 filter cake Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 238000003760 magnetic stirring Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000007670 refining Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000002932 luster Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000006487 butyl benzyl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- HRSFRSLKOPFWMZ-UHFFFAOYSA-N (3,4,5-trifluorophenyl)methanol Chemical compound OCC1=CC(F)=C(F)C(F)=C1 HRSFRSLKOPFWMZ-UHFFFAOYSA-N 0.000 description 1
- JKXZDDOHUQHMBX-UHFFFAOYSA-N 1-tert-butyl-4-[(4-tert-butylphenyl)methylsulfonylmethyl]benzene Chemical class C(C)(C)(C)C1=CC=C(CS(=O)(=O)CC2=CC=C(C=C2)C(C)(C)C)C=C1 JKXZDDOHUQHMBX-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- HTMQZWFSTJVJEQ-UHFFFAOYSA-N benzylsulfinylmethylbenzene Chemical compound C=1C=CC=CC=1CS(=O)CC1=CC=CC=C1 HTMQZWFSTJVJEQ-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002481 ethanol extraction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 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
- 239000012452 mother liquor Substances 0.000 description 1
- KWUZCAVKPCRJPO-UHFFFAOYSA-N n-ethyl-4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound C1=CC(NCC)=CC=C1C1=NC2=CC=C(C)C=C2S1 KWUZCAVKPCRJPO-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (6)
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CN201210429384.XA CN102924349B (zh) | 2012-11-01 | 2012-11-01 | 一种制备双(4-叔丁基苄基)硫醚产品的方法 |
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CN201210429384.XA CN102924349B (zh) | 2012-11-01 | 2012-11-01 | 一种制备双(4-叔丁基苄基)硫醚产品的方法 |
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CN102924349A true CN102924349A (zh) | 2013-02-13 |
CN102924349B CN102924349B (zh) | 2014-05-28 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103880723A (zh) * | 2014-03-12 | 2014-06-25 | 常州大学 | 一种制备二苄基硫醚产品的方法 |
WO2023123566A1 (zh) * | 2021-12-31 | 2023-07-06 | 江苏极易新材料有限公司 | 硫代二乙撑双[3-(3,5-二叔丁基-4-羟基苯基)丙酸酯]的合成方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101607930A (zh) * | 2008-06-19 | 2009-12-23 | 天津市化学试剂研究所 | 二苄基二硫醚的制备方法 |
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2012
- 2012-11-01 CN CN201210429384.XA patent/CN102924349B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101607930A (zh) * | 2008-06-19 | 2009-12-23 | 天津市化学试剂研究所 | 二苄基二硫醚的制备方法 |
Non-Patent Citations (4)
Title |
---|
GUNTHER BUEHRDEL等: "Synthesis of New Lipophilic Sulfones and Their Use in Cyclization Reactions", 《PHOSPHORUS, SULFUR, AND SILICON AND THE RELATED ELEMENTS》 * |
张鲁西等: "聚苯乙烯固载聚乙二醇催化合成二苄基硫醚", 《湖南师范大学自然科学学报》 * |
戴瑜嘉等: "相转移催化法合成硫醚和硫氰酸酯", 《西北师范大学学报(自然科学版)》 * |
李源勋等: "芳香族对称硫醚和硫氰酸酯的三相催化合成", 《化学试剂》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103880723A (zh) * | 2014-03-12 | 2014-06-25 | 常州大学 | 一种制备二苄基硫醚产品的方法 |
CN103880723B (zh) * | 2014-03-12 | 2016-08-17 | 常州大学 | 一种制备二苄基硫醚产品的方法 |
WO2023123566A1 (zh) * | 2021-12-31 | 2023-07-06 | 江苏极易新材料有限公司 | 硫代二乙撑双[3-(3,5-二叔丁基-4-羟基苯基)丙酸酯]的合成方法 |
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CN102924349B (zh) | 2014-05-28 |
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Effective date of registration: 20221028 Address after: 257400 Lijin County Economic Development Zone, Dongying, Shandong Patentee after: SHANDONG ZHENGXIN NEW ENERGY Co.,Ltd. Address before: 223800 No. 37-6, Beiguan Park, Sucheng District, Suqian City, Jiangsu Province Patentee before: Jiangsu BofA Construction Engineering Co.,Ltd. |
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