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SYN'tfiES OF ALLtYLTHlOPlf U<;S , DlTHIALKAN~ AND :tBIACYCLOHF~!IE D~IVAl'lVES OF' KlfO\~N STHUC'l'U.lE THESIS SUBMl'.t'T~:O l PAHTIAL FUL lLL · T OF THE 11E~UI l&iiEtfTS FOrt TJle DEGREE OF IIAOTE3 0 SCI... CE IN CHBMISTttY I N THE GRAOUA.~.E DIVISION OF TEXAS \YO~N ' 3 UNIW.:HS I TY DEP !iTl4~'::NT OF C li~M I ST!{Y BY :.LARTBA CHUN- L l BSIU, B. S . DENTON , T.ax.AS JUlff~ . 1 960 ABSTH CT .Hsiu, Martha Chun-Li. Synt~'lasis £!. ~ oro:18 Alkvl thiophen~t~~, Dit hia.lkanes, ~ ~­ cyclohcxo..nos 2!_ Known St:ructur9. Dir~ c t c by Dr. Rober"& W. Higgins, Juno, 1960. Sub.tli +-ted f'or aster of Science Degree. Soma tli4G ago the s r.aff of the Department of Cho:.nis try at ,~,ex&s \!o. w1 1 c Uni'leraity beoau.te interested i.n de termining the atruc~u r.~tJ o:f ot•ganio suLfur com:.>onnds i n petroleum. The method e!Jt)loyed wae an indirect one in that the prop..:rti as or e n t?ounde of know!'l struct uz-e , synthesized by a ccepted procedures, wer19 co::apared with the p.roport1"s of ,u,..e !!Ul!'ur compounds iso­ la tad fro:a pot.:ooleum fr11ctions . In the event all the properties i n vestigated were "&he swne, it could be coneludod t hat tha structures or the t'lio compounds we.:-e 1dont1c a.l. lnt e~ost as a1rectad toward t hose s ulfur constitu­ ent:! in pstroleu.."'! for cany reasons. Firstly 6 there wns a pur~ly ncado:ale 1nte1•est in that one is naturally curious about the cno.mi. co.l ns.turn or all natural p:'oducts. In this particular case it was felt that further knoT;ledge on the structure of the co s t i r.uo...lts in petroleura r:ould a lso !!hod some light on t ho origi n of this ~st i::tporto.nt natura.l rQ­ s ource. Secondly, the petroleum industry is vi tally interested 1 2 in the nature of these sul .fur constituents in petroleum .for e oono:nic reasons. Thirdly, t)roparation o~ a.ad itional sulf'ur co.:tpourds v:olll contribute a great deal t o t he fundamental knowled:a oJ" or ganic f'ull'ur chemistry. lt lo a well- known .fact t hat the sulfur comnoL.mds in .oetrol au;-!1 , particularly t he l .. e£1ned products obtainar !;nero­ fro,!, are obnoxious a.na dett'i.ll6ntal. fhe problt:.': 13 further co~>licatcd bec~use of t he dlrfi c ~ ltlcs aaaocinted ~ith the r'fJ:'l"lV:ll 0 C t J:e g'llr~Ur' Co.npol onts du.C'i . g Cl18 .re_"'ining processes • Ar.; .., 1e ttor )r f::1ct, in the past m1.1.ny of cho o:l fielus which had a hl;h sul.:'u"' co~tent waro by-passed. .no .. eva;·, ·,ti tl1 the inc :r~·J~ sed uses or pe-;roleUL'l in our higt.l.r .nechanizod civili­ zn't'!.on ~ it !a nocoss!'lry to ur.llizo all ~inda of patrolouro .flBlds, mr ~:;n tho:Je v.hich preEwnt problema. It is bcliovod b:,. man:) authorities on pctroloum .re~ini!l; that :nore efficient letl'ous of rg;novlnp, the ha~--mfu l .eul fur impuPi tios could be achieved 11' th~ cLemical structure of' tho sulfur cons ti tuants were known. Consequently tho major objective of this l nvastlgution was to 'Jrepare s. series or o rganic sul rur oo rn~ounds of' k."lown st,'uoture to serve as refer­ ence stu.ndards in tha identification of sulfur compounJ~ 1Rolated from potrolou.n. The :f'irat t:rpos o r eulf'ur CO!:t:>Ound s prepure l~ in the Texas \. o~an' s Un1 versi t1 laboratories woro thiophene der-i v ­ ativaa. Interest wag initiaL!.. .; focuoa,1 oa t l1is type atl"ucture because 't!Wl:f earlier investigators had obtained evidenc e that so:no st""uctu.l.. tH of thls t ;:rpc wer•o _)r&s~nt ln petrole\1!!1. 0!' course, onLy a ver.·y few of tha many thousands or possiole s true t·--1res C"J'tld be raado ln the cou.rao of c.!.m.e l.nol vod i n t!-1-Ls -:.•ono·~rch wo!"~ . ~'ho compounds of this t y p13 preparod in e. hin;i~ d!l.J; !'P.~ o.f j)'ll"'lt:~ by this lnv&sti :fitor ncre 2-1>:-o-Jyl­ th:!.,")) h.One, 2- pontyl thio;.>hone. ·~-prop '1- 2-isoaeyl thlo.Jhone and ?.- ~J~nt, ; l - 5- hexy l thiophene. So;no a :;tontion was dil.. eoted towaPd effoctlnt-.:; u syn­ thosin o f t L t icy cl ohexan~ and 1 ts c.l.'::,:;l dc~ .... iv<.lt iven. lt \'.na ant lc.t )n.'Cod i. h a t: .nany of the hic her boiling sul~u..:-> cons ._.i.. tu­ ent:=t ::! .~ 1P.troleum , ,.e~e cyclic :in nature 02, ~"~von pol:rcycl!c .. ThorofOPf', ~Jf;tho•is wero sought to ?~:·opare, at firet, some or she sir:n? l<$!'!;; o.r the thiacyclohoxano r!o.!'ivativos. .!any prt>b­ l"> .. ts ~-:e:rc ')JlOOUnt~recl . 1i'l:lincyc lohOX:tne ~md its 1-lllOt h l d oriva tivA 'h'f'ro prepa:-ecl but unfortunatol;;; noi the..:· in n high dc Lo.;l"e~"' of purity nor in h"'cd yields. This synth etic problem nE>qds further 1nvescigation. 111hcn di.fficulty vws c:'lcounterec in the ;> r'3puratio:'l ot: t!:.iac;olohexane, it was deemed l't'iao to t'vllow a sideline th 'l t presented itself during the sys1the~is o.f chi o.cyclohoxane. An 1nternedlf\t6 i n the at,te.il;:>teo. prOptirat.lo.u o£ ch1aoyclohexane by one ~.)ro ced u:>'J wsa 1 , 5- di thlaponttme. '.~.:.is compou.::1d '< · ag rE*adily all.. y lated .lth n- pro;Jyl bromide to yield a dithiallume, na:11ely, 4,10- dithi ntridocane. Anotr·r-1" i.ithialknnf'! pre;.H!::'c<l ~· as 4 , 7- dith.iudocane. 4 All the compounds produced were lnilestl gatod in the rexr..s 'No.rtl-! ri t s Uni vor>.,i ty i C~"'Obiolog i cal '{osearch Laboratory. The .. e roesul ts will oG compiled lilld Jr esr,nted in a saparate t r. esi s. ACKliOWLEDGMENTS In acknowledging her deep sense of obligation to them, the au thor 1 ants to thank all members of the raoul ty and ad­ ministr ation of Texas Woman's University who have assisted her in the pursuit of the Master of Science degree . She is p ar­ ticularly graterul to Dr . Robert W. Higgins, who directed this research problem with encourae;ernent and enthusiasm during the pas t two years. In the preparati on of this thesis, the author wishes to extend her appreciation to Dr. Hobert W. Hi ggins and Dr. Helen A. Ludeman for their s uggestions and assistance. The author furthermore w1 shes to express her sincere gratitude to The Robert A. \Y eleh Foundation of Houston , Texas , !'or a generous grant to t he Dopartment of Chemistry of Texas \•J oman's University which m.ade t his work pos s ible. 111 TABLE OF' COlt~ENTS Page I . INT10:>UCTION • • . .. 1 II. EISTOHICAL • . 5 A. Alkylthiophenee . 5 B. Thi a c y clohexane and Derivati ves • . .. 13 C. Di thialkanes . 18 III. DISCUSSION • • • • . 20 A. Prepa ration of 2-Alkyl- and 2 , 5-Dialkyl- thiophenes • • • • • • • • • • • • • 20 B. Thiac y clohexa.ne and Its Derivatives . 22 1. Problems associated wi th preparation of thiacyclohexane • . • • • • • • • • . 22 2. Synthesis of i ntermediate products in the preparation or alkylthia- cycl ohexa.nes • • . • . • • • • 25 3 . Preparation of 4- ethy lthiacyclo- hexane . , . • • 2 7 0 • .Preparation of D1 thialkanes • • • • • • 27 1. Synthesis of alpha, omega di thiols • 2 7 IV. EXPERIMENTAL • . 29 A. Preparation of 2-Alkylth iophenes . 29 I. Synthesis of 2- propylthiophene • 29 a. Acylation of t h iophene with propionic anhydride • 29 b . olff-Kishner reduction of 2- propanoylthiophene 2 9 1v 2. Synthesis or 2- Arnylthio~hene . 30 a. Preparation or n-butyl cyanide . • . 30 b. Preparo.t1 on o£ n- valeric acid ... 31 c. Preparation or n-vale.ryl chloride 31 d. Preparation of 2-pentanoylthiophene . • 32 e. Wo1ff-Kishner reduction of' 2-pentanoylthiophene •• . 32 B. Preparation of 2, 5-Dialkylthiophenes . .. 33 1. Synthesis of 2-Propyl-5-ieoamyl­ thiophene • • • • • • • . • • . 33 a. Preparation of' 2-propyl - 5-iso- valerythlophene • . • • . • . 33 b. \Uol.ff-Kishnor reduction of' 2 - propyl- 5-isovalcrythiophene • • • • . 34 2. Preparation of' 2-Amyl-5-hexyl- thiophene • . • • • • • • • • • • . 35 a. Synthesis of' 2-amyl-5- hexanoylthiophene • • • • • • • • • • 35 b. \ o1ff- Kishner reduction of 2-amyl- 5-he.xanoylthiophene • . 35 C. Synthesis of Thiacyclohexane and Der1 v a.tives • • • • • • • • • • . 36 1. Preparation of Thiacyclohexane • . 36 2 . Preparation of 4-Methylthiacyclo- hexane . 37 3 . Preparation of Intermediates in the Synthesis of A1kylth1aeyclohexanes . • • 37 a.. Synthesis of diethyl 3,3-dimetbyl glutarate • . • . 37 b. Preparation of' 3 ,3-dimethyl 1,5- pentanedlol • . • • . • • • • • • • . 38 c. Preparation of 3 , 3-dimethyl 1,5- dibromopentane • • • . • . • . 39 v d. Preparation o£ 1- i odo-5-chloropcntone . 39 e . Synthesifl of di thialkanes • 40 1 . Synthesis of Alksnedithiols • . 40 a . Preparation of: 1,2-ethanedi thiol 40 b . Preparation of 1 , 5- pentanedithlol ••.• 41 2 . Alkyl ation o£ Alkanedi thiols • . • • • • . • 42 a .
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    DEVELOPMENT OF CHEMICAL TOOLS FOR STUDYING REACTIVE SULFUR SPECIES by MATTHEW MICHAEL CERDA A DISSERTATION Presented to the Department of Chemistry and Biochemistry and the Graduate School of the University of Oregon in partial fulfillment of the requirements for the degree of Doctor of Philosophy June 2020 DISSERTATION APPROVAL PAGE Student: Matthew Michael Cerda Title: Development of Chemical Tools for Studying Reactive Sulfur Species This dissertation has been accepted and approved in partial fulfillment of the requirements for the Doctor of Philosophy degree in the Department of Chemistry and Biochemistry by: Michael M. Haley Chairperson Michael D. Pluth Advisor Darren W. Johnson Core Member Raghuveer Parthasarathy Institutional Representative and Kate Mondloch Interim Vice Provost and Dean of the Graduate School Original approval signatures are on file with the University of Oregon Graduate School. Degree awarded June 2020 ii © 2020 Matthew Michael Cerda This work is licensed under a Creative Commons Attribution-NonCommerical-NoDerivs (United States) License. iii DISSERTATION ABSTRACT Matthew Michael Cerda Doctor of Philosophy Department of Chemistry and Biochemistry June 2020 Title: Development of Chemical Tools for Studying Reactive Sulfur Species Hydrogen sulfide (H2S) has recently emerged as an important biological signaling molecule involved in a number of key physiological processes. These observations have generated interest in harnessing H2S as a potential therapeutic agent to treat disease states and chronic conditions associated with H2S-based signaling. A mechanistic analysis of these physiological processes reveals the prevalence of H2S and other reactive sulfur species including sulfane sulfur and persulfides. To better understand the biological properties of these reactive sulfur species, chemical tools which provide methods of generating these fleeting species under controlled reaction conditions are needed.
  • Sodium Hydrosulfide Solution

    Sodium Hydrosulfide Solution

    SAFETY DATA SHEET 1. Identification Product identifier Sodium Hydrosulfide Solution Other means of identification Product number GENLP-TDC-001 Recommended use Product is a unique alkaline material, playing a vital role in many industrial processes. Recommended restrictions Use in accordance with supplier's recommendations. Manufacturer/Importer/Supplier/Distributor information Manufacturer TDC, L.L.C. and TDC Services, LLC Address 1916 Farmerville Hwy Ruston, LA 71270 Telephone Customer Service (800) 422-6274 Email [email protected] CHEMTREC: 800-424-9300 (Domestic – North America) CHEMTREC: +1-703-527-3887 (International) 2. Hazard(s) identification Physical hazards Corrosive to metals Category 1 Health hazards Acute toxicity, oral Category 3 Skin corrosion/irritation Category 1B Serious eye damage/eye irritation Category 1 Environmental hazards Hazardous to the aquatic environment, acute Category 1 hazard OSHA defined hazards Not classified. Label elements Signal word Danger Hazard statement May be corrosive to metals. Toxic if swallowed. Causes severe skin burns and eye damage. Very toxic to aquatic life. Precautionary statement Prevention Keep only in original container. Do not breathe mist or vapor. Wash thoroughly after handling. Do not eat, drink or smoke when using this product. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. Response If swallowed: Immediately call a poison center/doctor. Rinse mouth. Do NOT induce vomiting. If on skin (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower. Wash contaminated clothing before reuse. If inhaled: Remove person to fresh air and keep comfortable for breathing. If in eyes: Rinse cautiously with water for several minutes.
  • Redox Pty Ltd 2 Swettenham Road +61-2-97333000 Minto NSW 2566 Australia

    Redox Pty Ltd 2 Swettenham Road +61-2-97333000 Minto NSW 2566 Australia

    Safety Data Sheet Sodium hydrosulfide (70%) Revision 4, Date 10 Jan 2019 1. IDENTIFICATION Product Name Sodium hydrosulfide (70%) Other Names Sodium bisulfide; Sodium hydrogen sulfide; Sodium hydrogensulphide; Sodium hydrosulphide (solid/flake 70~72%); Sodium mercaptan Uses Leather treatment; dye and lubricant manufacture; wastewater treatment; metals finishing; ore beneficiation; pharmaceuticals. Chemical Family No Data Available Chemical Formula NaHS Chemical Name Sodium sulfide (Na(SH)) Product Description Sodium hydrosulphide with not less than 25% water of crystallization. Contact Details of the Supplier of this Safety Data Sheet Organisation Location Telephone Redox Pty Ltd 2 Swettenham Road +61-2-97333000 Minto NSW 2566 Australia Redox Pty Ltd 11 Mayo Road +64-9-2506222 Wiri Auckland 2104 New Zealand Redox Inc. 3960 Paramount Boulevard +1-424-675-3200 Suite 107 Lakewood CA 90712 USA Redox Chemicals Sdn Bhd Level 2, No. 8, Jalan Sapir 33/7 +60-3-5614-2111 Seksyen 33, Shah Alam Premier Industrial Park 40400 Shah Alam Sengalor, Malaysia Emergency Contact Details For emergencies only; DO NOT contact these companies for general product advice. Organisation Location Telephone Poisons Information Centre Westmead NSW 1800-251525 131126 Chemcall Australia 1800-127406 +64-4-9179888 Chemcall Malaysia +64-4-9179888 Chemcall New Zealand 0800-243622 +64-4-9179888 National Poisons Centre New Zealand 0800-764766 CHEMTREC USA & Canada 1-800-424-9300 CN723420 +1-703-527-3887 2. HAZARD IDENTIFICATION Poisons Schedule (Aust) Not Scheduled Globally