GB599733A - Improvements in or relating to the stabilisation of hydrocarbon materials - Google Patents
Improvements in or relating to the stabilisation of hydrocarbon materialsInfo
- Publication number
- GB599733A GB599733A GB119245A GB119245A GB599733A GB 599733 A GB599733 A GB 599733A GB 119245 A GB119245 A GB 119245A GB 119245 A GB119245 A GB 119245A GB 599733 A GB599733 A GB 599733A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isoprene
- oxidant
- per cent
- methylene blue
- chloride
- 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
- 239000004215 Carbon black (E152) Substances 0.000 title abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 title abstract 2
- 239000000463 material Substances 0.000 title abstract 2
- 230000003019 stabilising Effects 0.000 title 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 5
- 239000003963 antioxidant agent Substances 0.000 abstract 4
- 235000006708 antioxidants Nutrition 0.000 abstract 4
- CXKWCBBOMKCUKX-UHFFFAOYSA-M Methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 abstract 3
- 230000003078 antioxidant Effects 0.000 abstract 3
- 150000002978 peroxides Chemical class 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N Pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- 229940013123 stannous chloride Drugs 0.000 abstract 2
- 239000001119 stannous chloride Substances 0.000 abstract 2
- 235000011150 stannous chloride Nutrition 0.000 abstract 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin dichloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 abstract 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 abstract 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N Cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 1
- 229940079877 Pyrogallol Drugs 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000000111 anti-oxidant Effects 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 1
- 150000003841 chloride salts Chemical class 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 150000001896 cresols Chemical class 0.000 abstract 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 abstract 1
- 150000001993 dienes Chemical class 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- 238000005755 formation reaction Methods 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- -1 isoprene peroxide Chemical class 0.000 abstract 1
- 150000002751 molybdenum Chemical class 0.000 abstract 1
- 150000004780 naphthols Chemical class 0.000 abstract 1
- 230000033116 oxidation-reduction process Effects 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tBuOOH Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052720 vanadium Inorganic materials 0.000 abstract 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium(0) Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Diolefins or predominantly diolefinic hydrocarbon materials are stabilized by dissolving therein a phenolic type anti-oxidant, and a promoter therefor comprising a compound having a standard oxidation-reduction potential of 1-0.7 to 0 volts. Formation of peroxides is inhibited and, when already present, the content is reduced. Butadiene, isoprene, cyclopentadiene, piperylenes and their homologues are referred to. Phenolic type anti-oxidants include phenols, alkylated phenols, polyhydroxy benzenes and hydroxy naphthalenes, for example cresols, catechol, hydroquinone, pyrogallol, naphthols and their alkyl derivatives. Promoters specified are methylene blue chloride, stannous chloride or acetate or other soluble stannous salt, mercurous and titanous chlorides, platinous, uranous, trivalent vanadium and pentavalent molybdenum salts, lower oxides of copper and iron, hydrogen sulphide and elementary sulphur. The amount of anti-oxidant is desirably about twice that theoretically required for reduction of peroxide present, and the amount of promoter should be at least 10 per cent by weight of the anti-oxidant. Comparative figures are given for the inhibition of the polymerization of isoprene, containing peroxide equivalent to 100 p.p.m. active oxygen, at 60 DEG C., using 0.22 per cent a -naphthol with and without methylene blue chloride (0.03 per cent), and for the reduction of tert.-butyl hydroperoxide and isoprene peroxide in aromatic hydrocarbon solution using tert.-butyl catechol and a -naphthol, with and without methylene blue chloride or stannous chloride.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB599733A true GB599733A (en) | 1948-03-19 |
Family
ID=1626708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB119245A Expired GB599733A (en) | 1945-01-15 | Improvements in or relating to the stabilisation of hydrocarbon materials |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB599733A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3366702A (en) * | 1965-05-03 | 1968-01-30 | Marathon Oil Co | Preparation of unsaturated hydrocarbons by pyrolysis, and related compositions |
-
1945
- 1945-01-15 GB GB119245A patent/GB599733A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3366702A (en) * | 1965-05-03 | 1968-01-30 | Marathon Oil Co | Preparation of unsaturated hydrocarbons by pyrolysis, and related compositions |
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