CH495930A - Verfahren zur Entfernung von Verunreinigungen aus Olefinen - Google Patents

Verfahren zur Entfernung von Verunreinigungen aus Olefinen

Info

Publication number: CH495930A
Authority: CH; Switzerland
Prior art keywords: olefins; olefin; sulfonation; acid; treated
Prior art date: 1966-04-26

Application number

CH570967A

Other languages

German (de)

English (en)

Inventor

James Garner Philip

Neilson Moulden Howard

Original Assignee

Unilever Nv

Priority date (The priority date 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 date listed.)

1966-04-26

Filing date

1967-04-21

Publication date

1970-09-15

1967-04-21 Application filed by Unilever Nv filed Critical Unilever Nv

1970-09-15 Publication of CH495930A publication Critical patent/CH495930A/de

Links

150000001336 alkenes Chemical class 0.000 title claims description 189
238000000034 method Methods 0.000 title claims description 49
239000012535 impurity Substances 0.000 title claims description 11
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 115
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 52
239000002253 acid Substances 0.000 claims description 49
238000011282 treatment Methods 0.000 claims description 49
238000006277 sulfonation reaction Methods 0.000 claims description 39
239000003463 adsorbent Substances 0.000 claims description 30
238000010306 acid treatment Methods 0.000 claims description 24
239000003599 detergent Substances 0.000 claims description 21
238000004061 bleaching Methods 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 18
238000006317 isomerization reaction Methods 0.000 claims description 16
239000000047 product Substances 0.000 claims description 16
239000004711 α-olefin Substances 0.000 claims description 15
230000019635 sulfation Effects 0.000 claims description 14
238000005670 sulfation reaction Methods 0.000 claims description 14
-1 olefin sulfonates Chemical class 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
238000005406 washing Methods 0.000 claims description 11
230000001419 dependent effect Effects 0.000 claims description 10
238000002156 mixing Methods 0.000 claims description 9
239000003513 alkali Substances 0.000 claims description 6
239000007844 bleaching agent Substances 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
238000004821 distillation Methods 0.000 claims description 4
SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 claims description 3
229960000228 cetalkonium chloride Drugs 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
238000006386 neutralization reaction Methods 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
238000004448 titration Methods 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
150000003871 sulfonates Chemical class 0.000 claims 2
125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 20
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 18
150000001875 compounds Chemical class 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000012459 cleaning agent Substances 0.000 description 6
150000002430 hydrocarbons Chemical class 0.000 description 6
238000012360 testing method Methods 0.000 description 6
238000002474 experimental method Methods 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
238000011084 recovery Methods 0.000 description 4
239000002689 soil Substances 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000002835 absorbance Methods 0.000 description 3
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
238000004140 cleaning Methods 0.000 description 3
238000002845 discoloration Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000011552 falling film Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000010348 incorporation Methods 0.000 description 3
238000005191 phase separation Methods 0.000 description 3
150000004291 polyenes Chemical class 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000010802 sludge Substances 0.000 description 3
GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000356 contaminant Substances 0.000 description 2
239000000498 cooling water Substances 0.000 description 2
238000005336 cracking Methods 0.000 description 2
150000008050 dialkyl sulfates Chemical class 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
239000010408 film Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229910001209 Low-carbon steel Inorganic materials 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
239000004566 building material Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
229910000286 fullers earth Inorganic materials 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000011491 glass wool Substances 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
229910000372 mercury(II) sulfate Inorganic materials 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000005325 percolation Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000344 soap Substances 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
238000012795 verification Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/17—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with acids or sulfur oxides
- C07C7/171—Sulfuric acid or oleum

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Analytical Chemistry (AREA)
Oil, Petroleum & Natural Gas (AREA)
Water Supply & Treatment (AREA)
General Chemical & Material Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH570967A 1966-04-26 1967-04-21 Verfahren zur Entfernung von Verunreinigungen aus Olefinen CH495930A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB18187/66A GB1159728A (en)	1966-04-26	1966-04-26	Purification of Olefins and preparation of Sulphonates therefrom

Publications (1)

Publication Number	Publication Date
CH495930A true CH495930A (de)	1970-09-15

Family

ID=10108161

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH570967A CH495930A (de)	1966-04-26	1967-04-21	Verfahren zur Entfernung von Verunreinigungen aus Olefinen

Country Status (10)

Country	Link
US (1)	US3492343A (2)
AT (1)	AT283296B (2)
BE (1)	BE697619A (2)
CH (1)	CH495930A (2)
ES (1)	ES339781A1 (2)
GB (1)	GB1159728A (2)
GR (1)	GR32682B (2)
LU (1)	LU53525A1 (2)
NL (1)	NL144916B (2)
SE (1)	SE364954B (2)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3699157A (en) *	1970-04-06	1972-10-17	Chevron Res	Color reduction of olefin sulfonates
BE787813A (fr) *	1971-08-26	1973-02-21	Texaco Development Corp	Procede de traitement acide des olefines
US4940831A (en) *	1989-02-15	1990-07-10	Phillips Petroleum Company	Purification of cis-olefins

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2563369A (en) *	1949-01-04	1951-08-07	Shell Dev	Refining fuel oil
US3328460A (en) *	1964-02-04	1967-06-27	Allied Chem	Process for sulfonation of organic compounds
US3306945A (en) *	1964-03-11	1967-02-28	Union Carbide Corp	Purification of unsaturated hydrocarbons by adsorption using a molecular sieve adsorbent
DE1217367B (de) *	1964-04-08	1966-05-26	Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius & Brüning, Frankfurt/M	Verfahren zur Herstellung von Alkensulfonaten
US3322844A (en) *	1964-05-20	1967-05-30	Gulf Research Development Co	Process for purifying a normal alpha olefin
US3331882A (en) *	1964-10-29	1967-07-18	Exxon Research Engineering Co	Separating alpha monoolefins using a steamed faujasite molecular sieve

1966
- 1966-04-26 GB GB18187/66A patent/GB1159728A/en not_active Expired
1967
- 1967-04-19 GR GR670132682A patent/GR32682B/el unknown
- 1967-04-20 US US632402A patent/US3492343A/en not_active Expired - Lifetime
- 1967-04-21 SE SE05638/67A patent/SE364954B/xx unknown
- 1967-04-21 CH CH570967A patent/CH495930A/de not_active IP Right Cessation
- 1967-04-24 AT AT383867A patent/AT283296B/de not_active IP Right Cessation
- 1967-04-25 ES ES339781A patent/ES339781A1/es not_active Expired
- 1967-04-26 NL NL676705918A patent/NL144916B/xx unknown
- 1967-04-26 LU LU53525D patent/LU53525A1/xx unknown
- 1967-04-26 BE BE697619D patent/BE697619A/xx unknown

Also Published As

Publication number	Publication date
DE1643106B2 (de)	1975-08-21
SE364954B (2)	1974-03-11
LU53525A1 (2)	1968-03-18
BE697619A (2)	1967-10-26
AT283296B (de)	1970-07-27
ES339781A1 (es)	1968-08-16
DE1643106A1 (de)	1971-06-09
GR32682B (el)	1967-08-02
NL6705918A (2)	1967-10-27
GB1159728A (en)	1969-07-30
NL144916B (nl)	1975-02-17
US3492343A (en)	1970-01-27

Legal Events

Date	Code	Title	Description
1977-11-30	PL	Patent ceased

Publication	Publication Date	Title
EP0054724B1 (de)	1985-05-15	Verfahren zur vereinfachten Gewinnung von hellfarbigen waschaktiven alpha-Sulfofettsäureestern
DE1568311B2 (de)	1975-10-30	Verfahren zur Herstellung waschaktiver höherer Alkenylsulfonate
EP0040776B1 (de)	1984-09-19	Verfahren zur Konjugierung mehrfach ungesättigter Fettsäuren oder Fettsäuregemische
CH495930A (de)	1970-09-15	Verfahren zur Entfernung von Verunreinigungen aus Olefinen
DE1643106C3 (de)	1976-04-01	Verfahren zum Reinigen von alpha-Olefinen
EP0131913B1 (de)	1986-09-24	Verfahren zur schonenden Isolierung von Paraffinsulfonsäuren oder Paraffinsulfonaten aus den bei der Sulfoxidation von Paraffinen erhaltenen Reaktionsgemischen
DE2715069C2 (de)	1984-10-11	Verfahren zur Gewinnung von Alkalisalzen von Alkylsulfonsäuren
US2788310A (en)	1957-04-09	White oil process
DE1910860C3 (de)	1980-10-30	Verfahren zur Herstellung von Alkalialkansulfonaten
DE722590C (de)	1942-07-14	Verfahren zum Aufarbeiten von Absorptionsprodukten aus Olefinen mit mindestens 5 Kohlenstoffatomen und konzentrierter Schwefelsaeure
DE686476C (de)	1940-01-10	Verfahren zur Verbesserung der Eigenschaften von Kolophonium
US1673045A (en)	1928-06-12	Process for producing demulsifying agents for refining petroleum oil
DE3227491A1 (de)	1983-02-10	Verfahren zur herstellung von methylnaphthalin von loesungsmittelqualitaet
DE895289C (de)	1953-11-02	Verfahren zum Herstellen von Salzen saurer Alkylester
DE1102740B (de)	1961-03-23	Verfahren zur Gewinnung von Hydroperoxyden aus den Oxydations-produkten von dialkylierten aromatischen Kohlenwasserstoffen
DE2122274A1 (de)	1972-02-17	Verfahren zum Herstellen vor Alkan sulfonaten
DE970957C (de)	1958-11-20	Verfahren zur kontinuierlichen Herstellung hellfarbiger Alkylbenzolsulfonsaeuren
DE1468913C2 (de)	1971-01-28	Verfahren zur Gewinnung von reinem m-Xylol
DE362459C (de)	1922-10-27	Raffinierung von Mineraloelen u. dgl.
DE868299C (de)	1953-02-23	Verfahren zur Herstellung von kapillaraktiven Sulfohalogenierungsprodukten
DE2065477A1 (de)	1973-10-04	Verfahren zur abtrennung von schwefelsaeure aus einem reaktionsgemisch
AT260208B (de)	1968-02-12	Verfahren zur Herstellung von alkylaromatischen Kohlenwasserstoffen
DE2203815B2 (de)	1976-08-12	Verfahren zur herstellung von olefinsulfonaten
DE1242220B (de)	1967-06-15	Verfahren zur Herstellung von Alkylsulfonaten bzw. Alkylsulfonsaeureestern mit hoher Thermostabilitaet und geringer Faerbung aus Erdoelfraktionen
DE1793185A1 (de)	1971-12-16	Verfahren zur Herstellung von Alkansulfonsaeuren