TWI227223B - Method for producing 2,3-dichloro-1-propanol and epichlorohydrin - Google Patents
Method for producing 2,3-dichloro-1-propanol and epichlorohydrin Download PDFInfo
- Publication number
- TWI227223B TWI227223B TW91108584A TW91108584A TWI227223B TW I227223 B TWI227223 B TW I227223B TW 91108584 A TW91108584 A TW 91108584A TW 91108584 A TW91108584 A TW 91108584A TW I227223 B TWI227223 B TW I227223B
- Authority
- TW
- Taiwan
- Prior art keywords
- reactor
- dichloro
- propanol
- chlorine
- hydrogen chloride
- Prior art date
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- ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 2,3-dichloropropan-1-ol Chemical compound OCC(Cl)CCl ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 0.000 title claims abstract description 29
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 154
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims abstract description 126
- 239000007789 gas Substances 0.000 claims abstract description 91
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 88
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 88
- 238000006243 chemical reaction Methods 0.000 claims abstract description 87
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 81
- 239000000460 chlorine Substances 0.000 claims abstract description 81
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 81
- 238000007872 degassing Methods 0.000 claims abstract description 79
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 78
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000007788 liquid Substances 0.000 claims description 47
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 41
- 238000011049 filling Methods 0.000 claims description 21
- 238000005660 chlorination reaction Methods 0.000 claims description 17
- 229940044613 1-propanol Drugs 0.000 claims description 11
- 230000002079 cooperative effect Effects 0.000 claims description 10
- 229960005335 propanol Drugs 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000007127 saponification reaction Methods 0.000 claims description 5
- PUNGDGIPJMLONU-UHFFFAOYSA-N 3,3-dichloropropan-1-ol Chemical compound OCCC(Cl)Cl PUNGDGIPJMLONU-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 229910052704 radon Inorganic materials 0.000 claims 1
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 abstract description 2
- 238000012544 monitoring process Methods 0.000 abstract 2
- 239000012071 phase Substances 0.000 description 84
- 239000000243 solution Substances 0.000 description 53
- 239000006096 absorbing agent Substances 0.000 description 20
- 238000000926 separation method Methods 0.000 description 17
- 239000012043 crude product Substances 0.000 description 16
- 239000007810 chemical reaction solvent Substances 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 238000000605 extraction Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000012295 chemical reaction liquid Substances 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000003507 refrigerant Substances 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 5
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229910002804 graphite Inorganic materials 0.000 description 4
- 239000010439 graphite Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- XEPXTKKIWBPAEG-UHFFFAOYSA-N 1,1-dichloropropan-1-ol Chemical compound CCC(O)(Cl)Cl XEPXTKKIWBPAEG-UHFFFAOYSA-N 0.000 description 3
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- RZWHKKIXMPLQEM-UHFFFAOYSA-N 1-chloropropan-1-ol Chemical compound CCC(O)Cl RZWHKKIXMPLQEM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 229910052722 tritium Inorganic materials 0.000 description 2
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
- BXVSAYBZSGIURM-UHFFFAOYSA-N 2-phenoxy-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound O1CC2=CC=CC=C2OP1(=O)OC1=CC=CC=C1 BXVSAYBZSGIURM-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- RHSFBTRXGVQTDB-UHFFFAOYSA-N C(CC)O.[Cl] Chemical compound C(CC)O.[Cl] RHSFBTRXGVQTDB-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- -1 allyl chloride Chemical compound 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001128670A JP4721311B2 (ja) | 2001-04-26 | 2001-04-26 | ２，３−ジクロル−１−プロパノール及びエピクロルヒドリンの製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI227223B true TWI227223B (en) | 2005-02-01 |
Family
ID=18977333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW91108584A TWI227223B (en) | 2001-04-26 | 2002-04-25 | Method for producing 2,3-dichloro-1-propanol and epichlorohydrin |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP4721311B2 (https=) |
| CN (1) | CN1204102C (https=) |
| TW (1) | TWI227223B (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ294890B6 (cs) * | 2003-09-01 | 2005-04-13 | Spolek Pro Chemickou A Hutní Výrobu,A.S. | Způsob přípravy dichlorpropanolů z glycerinu |
| US20100032617A1 (en) * | 2007-02-20 | 2010-02-11 | Solvay (Societe Anonyme) | Process for manufacturing epichlorohydrin |
| JP5294144B2 (ja) * | 2008-04-03 | 2013-09-18 | ダイソー株式会社 | ジクロロヒドリンの製造法 |
| CN104059031A (zh) * | 2014-06-20 | 2014-09-24 | 中国天辰工程有限公司 | 一种二氯丙醇脱除气相氯化氢生产环氧氯丙烷的方法 |
| TWI547470B (zh) * | 2015-12-18 | 2016-09-01 | 長春人造樹脂廠股份有限公司 | 製造二氯丙醇之方法 |
| CN108059586B (zh) * | 2017-12-12 | 2021-08-17 | 浙江镇洋发展股份有限公司 | 一种甘油氯化制备二氯丙醇的方法 |
| CN111978205B (zh) * | 2020-08-12 | 2023-04-28 | 上海应用技术大学 | 一种连续合成4-氯-2-甲氧基亚氨基乙酰乙酸乙酯的方法及装置 |
| CN111925300B (zh) * | 2020-08-12 | 2022-10-14 | 上海应用技术大学 | 一种4-氯-2-甲氧基亚氨基乙酰乙酸乙酯的合成方法及装置 |
| CN112010776B (zh) * | 2020-08-12 | 2023-04-28 | 上海应用技术大学 | 一种连续合成4-氯-2-甲氧基亚氨基乙酰乙酸乙酯的方法及装置 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60258171A (ja) * | 1984-06-04 | 1985-12-20 | Showa Denko Kk | エピクロルヒドリンの製造方法 |
| JPH0643354B2 (ja) * | 1989-08-10 | 1994-06-08 | ダイソー株式会社 | ２，３―ジクロロ―１―プロパノールの連続的製法及びその装置 |
| JPH0725711B2 (ja) * | 1990-07-17 | 1995-03-22 | 昭和電工株式会社 | ２，３―ジクロル―１―プロパノールの精製法 |
| JP2705521B2 (ja) * | 1993-07-22 | 1998-01-28 | 昭和電工株式会社 | ２，３−ジクロル−１−プロパノールの精製法 |
-
2001
- 2001-04-26 JP JP2001128670A patent/JP4721311B2/ja not_active Expired - Fee Related
-
2002
- 2002-04-24 CN CN 02801406 patent/CN1204102C/zh not_active Expired - Lifetime
- 2002-04-25 TW TW91108584A patent/TWI227223B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1462265A (zh) | 2003-12-17 |
| CN1204102C (zh) | 2005-06-01 |
| JP4721311B2 (ja) | 2011-07-13 |
| JP2002322106A (ja) | 2002-11-08 |
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| MK4A | Expiration of patent term of an invention patent |