CA1080752A - Process for the continuous manufacture of o- and p-chlorotoluene - Google Patents
Process for the continuous manufacture of o- and p-chlorotolueneInfo
- Publication number
- CA1080752A CA1080752A CA259,016A CA259016A CA1080752A CA 1080752 A CA1080752 A CA 1080752A CA 259016 A CA259016 A CA 259016A CA 1080752 A CA1080752 A CA 1080752A
- Authority
- CA
- Canada
- Prior art keywords
- toluene
- chlorine
- chlorination
- catalyst
- reaction
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 title claims abstract description 21
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 186
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 48
- 239000000460 chlorine Substances 0.000 claims abstract description 33
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 33
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000011541 reaction mixture Substances 0.000 claims abstract description 16
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 17
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 229960002089 ferrous chloride Drugs 0.000 claims description 11
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical group Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 8
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical class ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract description 13
- 239000002585 base Substances 0.000 abstract description 4
- 238000009835 boiling Methods 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- 238000011403 purification operation Methods 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 22
- 229910052742 iron Inorganic materials 0.000 description 11
- 239000000047 product Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000003426 co-catalyst Substances 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009183 running Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- -1 ferrous halides Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2536261A DE2536261C3 (de) | 1975-08-14 | 1975-08-14 | Verfahren zur kontinuierlichen Herstellung von o- und p-Chlortoluol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1080752A true CA1080752A (en) | 1980-07-01 |
Family
ID=5953986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA259,016A Expired CA1080752A (en) | 1975-08-14 | 1976-08-13 | Process for the continuous manufacture of o- and p-chlorotoluene |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS601289B2 (Direct) |
| BE (1) | BE845239A (Direct) |
| BR (1) | BR7605246A (Direct) |
| CA (1) | CA1080752A (Direct) |
| CH (1) | CH619914A5 (Direct) |
| DD (1) | DD126297A5 (Direct) |
| DE (1) | DE2536261C3 (Direct) |
| FR (1) | FR2320926A1 (Direct) |
| GB (1) | GB1497015A (Direct) |
| IE (1) | IE43288B1 (Direct) |
| IL (1) | IL50249A (Direct) |
| IT (1) | IT1064920B (Direct) |
| NL (1) | NL7608831A (Direct) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4138243A1 (de) * | 1991-11-21 | 1993-05-27 | Bayer Ag | Verbessertes verfahren zur kernchlorierung von aromatischen kohlenwasserstoffen |
| JP2002154995A (ja) * | 2000-11-21 | 2002-05-28 | Toray Ind Inc | 塩素化芳香族化合物の製造法 |
| CN103724159B (zh) * | 2014-02-02 | 2016-02-03 | 安徽八一化工股份有限公司 | 氯化苯生产中酸性氯化液脱酸工艺 |
| CN105174217A (zh) * | 2014-06-20 | 2015-12-23 | 唐慧建 | 一种提纯氯甲苯副产氯化氢气体及吸收剂再生的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3226447A (en) * | 1960-12-22 | 1965-12-28 | Union Carbide Australia | Directed nuclear substitution-chlorination of aromatic hydrocarbons and halogenated aromatic hydrocarbons |
| FR1446139A (fr) * | 1964-09-02 | 1966-07-15 | Hooker Chemical Corp | Chloration du toluène |
| FR1491144A (fr) * | 1965-09-03 | 1967-08-04 | Tenneco Chem | Procédé pour la production de chlorotoluènes contenant une proportion relativement élevée de para-chlorotoluène |
-
1975
- 1975-08-14 DE DE2536261A patent/DE2536261C3/de not_active Expired
-
1976
- 1976-08-06 DD DD194235A patent/DD126297A5/xx unknown
- 1976-08-09 NL NL7608831A patent/NL7608831A/xx not_active Application Discontinuation
- 1976-08-11 CH CH1021676A patent/CH619914A5/de not_active IP Right Cessation
- 1976-08-11 GB GB33372/76A patent/GB1497015A/en not_active Expired
- 1976-08-11 BR BR7605246A patent/BR7605246A/pt unknown
- 1976-08-12 IT IT26261/76A patent/IT1064920B/it active
- 1976-08-12 IL IL50249A patent/IL50249A/xx unknown
- 1976-08-13 IE IE1801/76A patent/IE43288B1/en unknown
- 1976-08-13 JP JP51096187A patent/JPS601289B2/ja not_active Expired
- 1976-08-13 CA CA259,016A patent/CA1080752A/en not_active Expired
- 1976-08-16 BE BE169853A patent/BE845239A/xx not_active IP Right Cessation
- 1976-08-16 FR FR7624862A patent/FR2320926A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1064920B (it) | 1985-02-25 |
| FR2320926A1 (fr) | 1977-03-11 |
| JPS601289B2 (ja) | 1985-01-14 |
| IE43288L (en) | 1977-02-14 |
| IL50249A0 (en) | 1976-10-31 |
| DD126297A5 (Direct) | 1977-07-06 |
| GB1497015A (en) | 1978-01-05 |
| CH619914A5 (en) | 1980-10-31 |
| FR2320926B1 (Direct) | 1982-07-02 |
| BE845239A (fr) | 1977-02-16 |
| BR7605246A (pt) | 1977-08-09 |
| IL50249A (en) | 1980-10-26 |
| JPS5253822A (en) | 1977-04-30 |
| DE2536261A1 (de) | 1977-02-24 |
| DE2536261B2 (de) | 1977-09-22 |
| NL7608831A (nl) | 1977-02-16 |
| DE2536261C3 (de) | 1979-06-21 |
| IE43288B1 (en) | 1981-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |