DE2614139C3 - Verfahren zur ansatzweisen oder kontinuierlichen Herstellung von a , a , a , a ', a ' a '-Hexachlorxylol - Google Patents
Verfahren zur ansatzweisen oder kontinuierlichen Herstellung von a , a , a , a ', a ' a '-HexachlorxylolInfo
- Publication number
- DE2614139C3 DE2614139C3 DE2614139A DE2614139A DE2614139C3 DE 2614139 C3 DE2614139 C3 DE 2614139C3 DE 2614139 A DE2614139 A DE 2614139A DE 2614139 A DE2614139 A DE 2614139A DE 2614139 C3 DE2614139 C3 DE 2614139C3
- Authority
- DE
- Germany
- Prior art keywords
- xylene
- reaction
- chlorine
- reactor
- hexachloroxylene
- 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 description 42
- 230000008569 process Effects 0.000 title claims description 24
- 238000010924 continuous production Methods 0.000 title claims description 3
- 239000000460 chlorine Substances 0.000 claims description 117
- 229910052801 chlorine Inorganic materials 0.000 claims description 113
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 90
- 238000005660 chlorination reaction Methods 0.000 claims description 88
- 238000006243 chemical reaction Methods 0.000 claims description 87
- 239000011541 reaction mixture Substances 0.000 claims description 73
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 45
- 239000008096 xylene Substances 0.000 claims description 42
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 38
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 34
- 230000002829 reductive effect Effects 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 7
- NVLHGZIXTRYOKT-UHFFFAOYSA-N 1-chloro-2,3-dimethylbenzene Chemical group CC1=CC=CC(Cl)=C1C NVLHGZIXTRYOKT-UHFFFAOYSA-N 0.000 claims description 3
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical group ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 35
- 239000000047 product Substances 0.000 description 29
- 239000007789 gas Substances 0.000 description 27
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 25
- 125000001309 chloro group Chemical group Cl* 0.000 description 23
- 230000036961 partial effect Effects 0.000 description 23
- 238000003756 stirring Methods 0.000 description 20
- 238000006467 substitution reaction Methods 0.000 description 20
- 238000004587 chromatography analysis Methods 0.000 description 19
- 238000007710 freezing Methods 0.000 description 16
- 230000008014 freezing Effects 0.000 description 16
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 15
- -1 dicarboxylic acid chlorides Chemical class 0.000 description 15
- 239000012535 impurity Substances 0.000 description 14
- 238000009835 boiling Methods 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 229910052573 porcelain Inorganic materials 0.000 description 12
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000007086 side reaction Methods 0.000 description 7
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000001555 benzenes Chemical class 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- HOHVUOKYQMRVDO-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(dichloromethyl)-6-methylbenzene Chemical group CC1=C(Cl)C(Cl)=C(C(Cl)Cl)C(Cl)=C1Cl HOHVUOKYQMRVDO-UHFFFAOYSA-N 0.000 description 4
- GGZIUXGYCNYNNV-UHFFFAOYSA-N 1,3-bis(trichloromethyl)benzene Chemical group ClC(Cl)(Cl)C1=CC=CC(C(Cl)(Cl)Cl)=C1 GGZIUXGYCNYNNV-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 150000001804 chlorine Chemical class 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000007806 chemical reaction intermediate Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QICXTGCEPZAKNJ-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-(chloromethyl)-6-methylbenzene Chemical group CC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1CCl QICXTGCEPZAKNJ-UHFFFAOYSA-N 0.000 description 1
- WEWXCIOGPKAVFO-UHFFFAOYSA-N 1,2-bis(trichloromethyl)benzene Chemical class ClC(Cl)(Cl)C1=CC=CC=C1C(Cl)(Cl)Cl WEWXCIOGPKAVFO-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JZGJGLYZHPAEEN-UHFFFAOYSA-N CC1=CC(=CC=C1)C.[Cl] Chemical group CC1=CC(=CC=C1)C.[Cl] JZGJGLYZHPAEEN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JYNTUIIZRRKCJZ-UHFFFAOYSA-N ClCl(=O)(=O)=O Chemical compound ClCl(=O)(=O)=O JYNTUIIZRRKCJZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical class ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000021185 dessert Nutrition 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
-
- 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
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S204/00—Chemistry: electrical and wave energy
- Y10S204/902—Production of desired compound by wave energy in presence of a chemically designated nonreactant chemical treating agent, excluding water, chloroform, carbon tetrachloride, methylene chloride or benzene
- Y10S204/914—Only carbon, hydrogen or halogen atom in treating agent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50039587A JPS51115434A (en) | 1975-04-01 | 1975-04-01 | Process for preparation of aromatic dicarboxylic acid chloride |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2614139A1 DE2614139A1 (de) | 1976-10-14 |
| DE2614139B2 DE2614139B2 (de) | 1979-08-02 |
| DE2614139C3 true DE2614139C3 (de) | 1980-04-03 |
Family
ID=12557221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2614139A Expired DE2614139C3 (de) | 1975-04-01 | 1976-04-01 | Verfahren zur ansatzweisen oder kontinuierlichen Herstellung von a , a , a , a ', a ' a '-Hexachlorxylol |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4029560A (enExample) |
| JP (1) | JPS51115434A (enExample) |
| DE (1) | DE2614139C3 (enExample) |
| GB (1) | GB1532089A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2108317C1 (ru) * | 1996-11-22 | 1998-04-10 | Волгоградское открытое акционерное общество "Химпром" | Способ получения гексахлорпараксилола |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5353636A (en) * | 1976-10-25 | 1978-05-16 | Mitsubishi Gas Chem Co Inc | Preparatin of highly pure aromatic dicarboxylic acid dichloride |
| JP2745087B2 (ja) * | 1991-11-08 | 1998-04-28 | 呉羽化学工業株式会社 | メチル化芳香族化合物の塩素化方法 |
| US6174415B1 (en) | 1999-05-19 | 2001-01-16 | Occidental Chemical Corporation | Chlorinating side chains of aromatic compounds |
| KR102353684B1 (ko) * | 2013-09-13 | 2022-01-19 | 피닝스 코., 엘티디. | 트리클로로메틸 치환된 벤젠의 제조 방법 |
| CN104230704A (zh) * | 2014-09-30 | 2014-12-24 | 烟台裕祥精细化工有限公司 | 一种光氯化合成间/对苯二甲酰氯的方法 |
| CN104478696A (zh) * | 2014-12-12 | 2015-04-01 | 山东凯盛新材料有限公司 | 对苯二甲酰氯的制备方法 |
| CN104387263A (zh) * | 2014-12-12 | 2015-03-04 | 山东凯盛新材料有限公司 | 间苯二甲酰氯的合成工艺 |
| CN105367407A (zh) * | 2015-12-14 | 2016-03-02 | 山东凯盛新材料有限公司 | 制备间/对苯二甲酰氯的方法 |
| KR102595484B1 (ko) * | 2022-09-14 | 2023-11-01 | 애경케미칼주식회사 | 광량제어를 통한 테레프탈로일클로라이드의 제조방법 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB583634A (en) * | 1943-11-11 | 1946-12-23 | Du Pont | Production of chlorinated hydrocarbons |
| JPS5241249B2 (enExample) * | 1972-01-24 | 1977-10-17 |
-
1975
- 1975-04-01 JP JP50039587A patent/JPS51115434A/ja active Granted
-
1976
- 1976-03-29 US US05/671,698 patent/US4029560A/en not_active Expired - Lifetime
- 1976-03-31 GB GB12985/76A patent/GB1532089A/en not_active Expired
- 1976-04-01 DE DE2614139A patent/DE2614139C3/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2108317C1 (ru) * | 1996-11-22 | 1998-04-10 | Волгоградское открытое акционерное общество "Химпром" | Способ получения гексахлорпараксилола |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5545057B2 (enExample) | 1980-11-15 |
| DE2614139A1 (de) | 1976-10-14 |
| US4029560A (en) | 1977-06-14 |
| JPS51115434A (en) | 1976-10-12 |
| GB1532089A (en) | 1978-11-15 |
| DE2614139B2 (de) | 1979-08-02 |
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