DE2217530C3 - Verfahren zur kontinuierlichen Herstellung von durch Chloratome und/oder Sulfochloridgruppen substituierten Alkanen - Google Patents
Verfahren zur kontinuierlichen Herstellung von durch Chloratome und/oder Sulfochloridgruppen substituierten AlkanenInfo
- Publication number
- DE2217530C3 DE2217530C3 DE2217530A DE2217530A DE2217530C3 DE 2217530 C3 DE2217530 C3 DE 2217530C3 DE 2217530 A DE2217530 A DE 2217530A DE 2217530 A DE2217530 A DE 2217530A DE 2217530 C3 DE2217530 C3 DE 2217530C3
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- reaction
- alkanes
- paraffin
- liquid
- 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
- 150000001335 aliphatic alkanes Chemical group 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 16
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 title claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 title claims description 7
- 238000010924 continuous production Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 54
- 239000000460 chlorine Substances 0.000 claims description 44
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 34
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 239000007788 liquid Substances 0.000 claims description 26
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 24
- 239000007858 starting material Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- OSVXSBDYLRYLIG-UHFFFAOYSA-N chlorine dioxide Inorganic materials O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 claims description 6
- 235000019398 chlorine dioxide Nutrition 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000012188 paraffin wax Substances 0.000 description 28
- 239000000203 mixture Substances 0.000 description 25
- 239000007789 gas Substances 0.000 description 21
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000001993 wax Substances 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000012495 reaction gas Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- OMMLUKLXGSRPHK-UHFFFAOYSA-N tetramethylbutane Chemical compound CC(C)(C)C(C)(C)C OMMLUKLXGSRPHK-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OGALZCPQPHRSPZ-UHFFFAOYSA-N 8-chloropentadecane Chemical class ClC(CCCCCCC)CCCCCCC OGALZCPQPHRSPZ-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- JPABDWANHWLCIJ-UHFFFAOYSA-N [Cl].S(=O)=O Chemical compound [Cl].S(=O)=O JPABDWANHWLCIJ-UHFFFAOYSA-N 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- AIXMJTYHQHQJLU-UHFFFAOYSA-N chembl210858 Chemical compound O1C(CC(=O)OC)CC(C=2C=CC(O)=CC=2)=N1 AIXMJTYHQHQJLU-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000003963 dichloro group Chemical class Cl* 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- -1 n-tetraderane Chemical compound 0.000 description 1
- 239000008041 oiling agent Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N triacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2217530A DE2217530C3 (de) | 1972-04-12 | 1972-04-12 | Verfahren zur kontinuierlichen Herstellung von durch Chloratome und/oder Sulfochloridgruppen substituierten Alkanen |
| IT21576/73A IT981382B (it) | 1972-04-12 | 1973-03-13 | Processo per la preparazione di alcani sostituiti con atomi di cloro e oppure con gruppi solfo cloruro |
| US346404A US3911004A (en) | 1972-04-12 | 1973-03-30 | Production of substituted alkanes |
| NLAANVRAGE7304572,A NL182141C (nl) | 1972-04-12 | 1973-04-02 | Werkwijze ter bereiding van door chlooratomen en/of sulfochloridegroepen gesubstitueerde alkanen. |
| CA167,900A CA997368A (en) | 1972-04-12 | 1973-04-03 | Production of substituted alkanes |
| CH487573A CH589573A5 (enExample) | 1972-04-12 | 1973-04-05 | |
| CH112776A CH579536A5 (enExample) | 1972-04-12 | 1973-04-05 | |
| SU731907617A SU592349A3 (ru) | 1972-04-12 | 1973-04-06 | Способ получени хлоралканов и или алкансульфохлоридов |
| BE129786A BE797936A (fr) | 1972-04-12 | 1973-04-09 | Procede de preparation d'alcanes substitues par des atomes de chlore et/ou par des groupes sulfochlorure |
| FR7312881A FR2179919B1 (enExample) | 1972-04-12 | 1973-04-10 | |
| ES413571A ES413571A1 (es) | 1972-04-12 | 1973-04-11 | Procedimiento para la obtencion de alcanos sustituidos. |
| GB1736573A GB1419848A (en) | 1972-04-12 | 1973-04-11 | Production of chlorine- and/or sulphochloride-substituted alkanes |
| BR732650A BR7302650D0 (pt) | 1972-04-12 | 1973-04-12 | Processo para fabricar alcanos substituidos com atomos de cloro e/ou grupos sulfo-cloreto |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2217530A DE2217530C3 (de) | 1972-04-12 | 1972-04-12 | Verfahren zur kontinuierlichen Herstellung von durch Chloratome und/oder Sulfochloridgruppen substituierten Alkanen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2217530A1 DE2217530A1 (de) | 1973-10-31 |
| DE2217530B2 DE2217530B2 (de) | 1976-04-29 |
| DE2217530C3 true DE2217530C3 (de) | 1983-11-24 |
Family
ID=5841695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2217530A Expired DE2217530C3 (de) | 1972-04-12 | 1972-04-12 | Verfahren zur kontinuierlichen Herstellung von durch Chloratome und/oder Sulfochloridgruppen substituierten Alkanen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3911004A (enExample) |
| BE (1) | BE797936A (enExample) |
| BR (1) | BR7302650D0 (enExample) |
| CA (1) | CA997368A (enExample) |
| CH (2) | CH589573A5 (enExample) |
| DE (1) | DE2217530C3 (enExample) |
| ES (1) | ES413571A1 (enExample) |
| FR (1) | FR2179919B1 (enExample) |
| GB (1) | GB1419848A (enExample) |
| IT (1) | IT981382B (enExample) |
| NL (1) | NL182141C (enExample) |
| SU (1) | SU592349A3 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2805441A1 (de) * | 1978-02-09 | 1979-08-23 | Basf Ag | Verfahren zur herstellung von durch chloratome und/oder sulfochloridgruppen substituierten alkanen |
| US4488953A (en) * | 1983-06-13 | 1984-12-18 | Occidental Chemical Corporation | Purification of recycled paraffins in photochlorination process |
| RU2440979C1 (ru) * | 2010-10-21 | 2012-01-27 | Государственное образовательное учреждение высшего профессионального образования "Томский государственный университет" (ТГУ) | Способ получения фторалкансульфохлоридов |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2528320A (en) * | 1946-07-31 | 1950-10-31 | Du Pont | Continuous photochemical preparation of aliphatic sulfonyl chlorides |
| US2811485A (en) * | 1954-09-29 | 1957-10-29 | Dow Chemical Co | Process for chlorinating dimethyl ether |
| GB836093A (en) * | 1957-07-30 | 1960-06-01 | Lubrizol Corp | Preparation of hydrocarbon sulfonyl chlorides |
| NL299253A (enExample) * | 1962-10-15 | |||
| DE1194842B (de) * | 1962-11-02 | 1965-06-16 | Schering Ag | Verfahren zur Herstellung von Sulfomonocarbonsaeuredichloriden |
| US3402114A (en) * | 1965-02-19 | 1968-09-17 | Phillips Petroleum Co | Photochemical halogenation of hydrocarbons |
| US3584066A (en) * | 1966-01-11 | 1971-06-08 | Sir Soc Italiana Resine Spa | Method of chlorinating paraffins |
| US3505418A (en) * | 1966-03-08 | 1970-04-07 | Atlantic Richfield Co | Method for monochlorinating paraffins |
| US3577472A (en) * | 1968-05-28 | 1971-05-04 | Atlantic Richfield Co | Method for chlorinating paraffins |
-
1972
- 1972-04-12 DE DE2217530A patent/DE2217530C3/de not_active Expired
-
1973
- 1973-03-13 IT IT21576/73A patent/IT981382B/it active
- 1973-03-30 US US346404A patent/US3911004A/en not_active Expired - Lifetime
- 1973-04-02 NL NLAANVRAGE7304572,A patent/NL182141C/xx not_active IP Right Cessation
- 1973-04-03 CA CA167,900A patent/CA997368A/en not_active Expired
- 1973-04-05 CH CH487573A patent/CH589573A5/xx not_active IP Right Cessation
- 1973-04-05 CH CH112776A patent/CH579536A5/xx not_active IP Right Cessation
- 1973-04-06 SU SU731907617A patent/SU592349A3/ru active
- 1973-04-09 BE BE129786A patent/BE797936A/xx not_active IP Right Cessation
- 1973-04-10 FR FR7312881A patent/FR2179919B1/fr not_active Expired
- 1973-04-11 GB GB1736573A patent/GB1419848A/en not_active Expired
- 1973-04-11 ES ES413571A patent/ES413571A1/es not_active Expired
- 1973-04-12 BR BR732650A patent/BR7302650D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU592349A3 (ru) | 1978-02-05 |
| FR2179919A1 (enExample) | 1973-11-23 |
| CA997368A (en) | 1976-09-21 |
| CH579536A5 (enExample) | 1976-09-15 |
| BR7302650D0 (pt) | 1974-07-18 |
| CH589573A5 (enExample) | 1977-07-15 |
| NL7304572A (enExample) | 1973-10-16 |
| DE2217530B2 (de) | 1976-04-29 |
| NL182141B (nl) | 1987-08-17 |
| US3911004A (en) | 1975-10-07 |
| NL182141C (nl) | 1988-01-18 |
| ES413571A1 (es) | 1976-01-16 |
| IT981382B (it) | 1974-10-10 |
| DE2217530A1 (de) | 1973-10-31 |
| GB1419848A (en) | 1975-12-31 |
| FR2179919B1 (enExample) | 1976-05-07 |
| BE797936A (fr) | 1973-10-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8226 | Change of the secondary classification |
Free format text: C07C 17/10 C07C143/70 |
|
| 8281 | Inventor (new situation) |
Free format text: HERTEL, OTTO, DR. SCHLECHT, HELMUT, DR., 6700 LUDWIGSHAFEN, DE SCHNEIDER, ROLF, DR., 6800 MANNHEIM,DE |
|
| AG | Has addition no. |
Ref country code: DE Ref document number: 2805441 Format of ref document f/p: P |
|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8380 | Miscellaneous part iii |
Free format text: ES MUSS RICHTIG HEISSEN: SPALTE 1, ZEILE 35: "ALKANEN, DIE" SPALTE 5, ZEILE 34: "ZWECKMAESSIG" SPALTE 7, ZEILE 9: "GASGESCHWINDIGKEIT". |
|
| 8339 | Ceased/non-payment of the annual fee |