CN101704722B - 二元羧酸-稀土氯化物催化甘油氯化合成二氯丙醇的方法和反应装置 - Google Patents
二元羧酸-稀土氯化物催化甘油氯化合成二氯丙醇的方法和反应装置 Download PDFInfo
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- CN101704722B CN101704722B CN2009102313090A CN200910231309A CN101704722B CN 101704722 B CN101704722 B CN 101704722B CN 2009102313090 A CN2009102313090 A CN 2009102313090A CN 200910231309 A CN200910231309 A CN 200910231309A CN 101704722 B CN101704722 B CN 101704722B
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 203
- 238000005660 chlorination reaction Methods 0.000 title claims abstract description 189
- 238000000034 method Methods 0.000 title claims abstract description 54
- 229910052761 rare earth metal Inorganic materials 0.000 title claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 title claims description 68
- XEPXTKKIWBPAEG-UHFFFAOYSA-N 1,1-dichloropropan-1-ol Chemical compound CCC(O)(Cl)Cl XEPXTKKIWBPAEG-UHFFFAOYSA-N 0.000 title abstract description 14
- 230000002194 synthesizing effect Effects 0.000 title abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 163
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000002131 composite material Substances 0.000 claims abstract description 22
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- 230000006837 decompression Effects 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 142
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 142
- 235000011187 glycerol Nutrition 0.000 claims description 83
- 239000007789 gas Substances 0.000 claims description 82
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- 230000008676 import Effects 0.000 claims description 27
- -1 rare earth chloride Chemical class 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 12
- 230000003197 catalytic effect Effects 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 238000007670 refining Methods 0.000 claims description 9
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 8
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000010521 absorption reaction Methods 0.000 claims description 5
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
- 229910052746 lanthanum Inorganic materials 0.000 claims description 4
- 238000012423 maintenance Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 abstract 2
- 230000036632 reaction speed Effects 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 11
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 10
- 150000001735 carboxylic acids Chemical class 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
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- 239000004593 Epoxy Substances 0.000 description 4
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000010025 steaming Methods 0.000 description 4
- 238000007171 acid catalysis Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 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 3
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- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
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- 239000000047 product Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 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
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminum chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000002551 biofuel Substances 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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CN2009102313090A CN101704722B (zh) | 2009-12-02 | 2009-12-02 | 二元羧酸-稀土氯化物催化甘油氯化合成二氯丙醇的方法和反应装置 |
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CN2009102313090A CN101704722B (zh) | 2009-12-02 | 2009-12-02 | 二元羧酸-稀土氯化物催化甘油氯化合成二氯丙醇的方法和反应装置 |
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CN108059586A (zh) * | 2017-12-12 | 2018-05-22 | 宁波镇洋化工发展有限公司 | 一种甘油氯化制备二氯丙醇的方法 |
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CN105237353B (zh) * | 2014-10-24 | 2019-05-07 | 连云港环海化工有限公司 | 一种甘油氯化残液的回收利用方法 |
CN106518610A (zh) * | 2016-11-08 | 2017-03-22 | 威海恒邦化工有限公司 | 一种含氯化氢尾气的处理方法 |
CN111871243A (zh) * | 2020-08-01 | 2020-11-03 | 浙江亦龙新材料有限公司 | 一种生产丙烯酸脂乳液的乳化系统 |
CN113480407B (zh) * | 2021-05-17 | 2023-03-21 | 北京化工大学 | 一种二氯丙醇的连续化制备系统及方法 |
Citations (3)
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CN1882522A (zh) * | 2003-11-20 | 2006-12-20 | 索尔维公司 | 从甘油生产二氯丙醇的方法,甘油最终来自生物柴油生产中动物脂肪的转化 |
CN1995002A (zh) * | 2006-12-22 | 2007-07-11 | 华东理工大学 | 稀土化合物在酰氯化反应中的应用 |
CN101337950A (zh) * | 2008-07-30 | 2009-01-07 | 江苏工业学院 | 甘油反应精馏法连续制备环氧氯丙烷的方法 |
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CN1882522A (zh) * | 2003-11-20 | 2006-12-20 | 索尔维公司 | 从甘油生产二氯丙醇的方法,甘油最终来自生物柴油生产中动物脂肪的转化 |
CN1974511A (zh) * | 2003-11-20 | 2007-06-06 | 索尔维公司 | 用于生产有机化合物的方法 |
CN1995002A (zh) * | 2006-12-22 | 2007-07-11 | 华东理工大学 | 稀土化合物在酰氯化反应中的应用 |
CN101337950A (zh) * | 2008-07-30 | 2009-01-07 | 江苏工业学院 | 甘油反应精馏法连续制备环氧氯丙烷的方法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN108059586A (zh) * | 2017-12-12 | 2018-05-22 | 宁波镇洋化工发展有限公司 | 一种甘油氯化制备二氯丙醇的方法 |
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