The West Indies Chemical Works Ltd. and Logwood in Jamaica.

Haematoxylum campechianum (logwood or bloodwood tree) is a species of flowering tree in the legume family, Fabaceae, which is native to southern Mexico and northern Central America. The tree was of great economic importance from the 17th century to the 19th century, when it was commonly logged and exported to Europe for use in dyeing fabrics. The tree's scientific name is derived from the Greek haima for blood and xylon for wood, hence "bloodwood".

Logwood extract was first used by the Mayans and Aztecs as an ink, a fabric dye, and a treatment for diarrhoea. It has been reported that when Hernando Cortez encountered the Nahuatl Aztecs in 1519, they were dressed in the rich violet and black colours derived from logwood extract. However the Spaniards originally used the trees as ballast and did not realise the potential as a dye until the late 1500's after it had been introduced into other European countries, including England. The Crown of Spain then attempted to create and maintain a monopoly and logwood was contraband cargo for non-Spanish ships and subject to confiscation.

In the early 1500's during Henry VIII's reign, Privateer's discovered that one shipload of logwood could generate the equivalent of a year's value from any other cargo. The breaking of the Spanish logwood monopoly is considered a factor in the sinking of the Spanish Armada in 1588.

There was a time though when the use of logwood dyes could land you in a pillory. Elizabeth I issued Statute 39, "An Act for the better Execution of the Statute made in the twenty-third year of the Queen's reign, for the abolishing of logwood, alias blockwood, in the dying of Cloth or other Stuff." The deceitful users of Logwood were under the aforesaid Statute, 39 Elizabeth, to be tried, and, if found guilty, fined and set in the pillory.
The following are the preamble and first section of Statute 23 issued by Elizabeth I in 1567, "Whereas, of late years, there hath been brought into this Realm a certain kind of stuff called logwood alias blockwood, wherewith divers do dye daily divers things: Forasmuch as the colour made with the said stuff is false and deceitful : Be it, &c., that all such Logwood alias Blockwood, in whose hands soever the same shall be found, after the feast of St. Michael the Archangel next ensuing, shall be forfeited and openly burned by authority of the Mayor, or other head officer of the city or town corporate, or of two Justices of peace of the county where it shall be found, and that, from and after 20 days after the end of this Session of Parliament, no person, of what degree soever he be, shall dye or cause to be dyed any cloth, wool or any other of the premises above mentioned, or any other thing whatsoever, with any of the said ware or stuff called Logwood alias Blockwood, upon pain that the dyer of every such several things so dyed shall forfeit the value of the same thing so dyed ; the one moiety to the use of the Queen's Majesty, her heirs or successors, and the other moiety to him that will sue for the same by action of debt, bill, plaint, or information in any court of record, in which suit no Essoine, Protection, Wager of Law, nor Writ of Privilege for the defendant shall be admitted or allowed, and the party offending, being thereof convicted, to remain in prison, without bail or mainprise, till he hath satisfied the same value."

These statutes were finally repealed by Charles in 1662 who declared: "the ingenious industry of modern times hath taught the dyers of England the art of fixing colours made of logwood . . . so as that, by experience, they are found as lasting as the colours made with any other sort of dyeing-wood whatever, and on this ground it repeals so much of the Statute of Elizabeth as related to logwood, and gives permission to import it and use it for dyeing"

Early in the 17th century, on the shores of the Bay of Campeche in south-eastern Mexico and on the Yucatan Peninsula, English buccaneers began cutting logwood, which was used in the production of a dye needed by the wool industry. According to legend, one of these buccaneers, Peter Wallace, called "Ballis" by the Spanish, settled near and gave his name to the Belize River as early as 1638. (Other sources, however, assert that the river's name comes from the Mayan word belix or beliz, meaning "muddy-watered".)

Shortly after England took possession from the Spanish of Jamaica the export of logwood began to flourish. The town of Black River, is one of the oldest in Jamaica, being shown on maps as early as 1685. The town had a busy seaport and by 1773 it had become the capital of St Elizabeth (replacing Lacovia) and supported a lucrative logwood trade and export of rum, pimento and cattle skins. Logwood was used to generate steam from a power plant with large furnace and boiler that generated electricity from as early as 1893 and was the first in the island.[5]

The use of logwood as a dye was described by Robert Hooke (1635-1703) in 1650 although it is not recorded whether in his microscopic investigations he recognized its use as a stain for cell tissues. [6]

Georg Christian Reichel (1721-1771) is considered the first to use logwood extracts as a histology stain (in his case plant tissues). Edwin John Quekett (1808-1847) and his younger brother John Thomas Quekett (1815-1861) were founding members in 1839 of the Royal Microscopical Society and early meetings were held in John's house in London. Edwin was a student of Professor Edward Turner (1796 Clarendon, Jamaica-1837 London) at the University of London and received the First Silver Medal in Edwards's first Chemistry class of 1828-1829. John described the direct use of the logwood extract in his 1848 book "Practical Treatise on the Use of the Microscope".[7]

Freidrich Bohmer (1829- ) copied the use of the addition of mordants (like potassium alum) to haematoxylin/haematein from the textile industry and in 1865 was able to initiate the extensive use of logwood derived stains. Note though that he published his findings in a regional medical journal and it was only after being cited some years later that this development was implemented.[8]

The main extract from logwood is haematoxylin. Haematoxylin is relatively colourless and without further modifications has little or no value as a biological stain, unless it is oxidized in a process called ripening to yield haematein, which may be combined with mordants, including Al, Cr and Fe salts to achieve a range of colours. The use of the word "hematoxylin" to describe a staining solution is some-what misleading but continues to be used as a term of convenience. [9,10,11] The process of oxidizing haematoxylin to haematein, which is the active staining ingredient can be achieved either naturally and artificially. The structure of haematein and the related brasilein was predicted by Paul Pfeiffer and Alfred Werner in 1904.[12]

The structure of haematoxylin and haematein
Haematoxylin= (6aR,11bS)-7,11b-Dihydroindeno[2,1-c]chromene-3,4,6a,9,10(6H)-pentol
Haematein = 3,4,6a,10-Tetrahydroxy-6a,7-dihydroindeno[2,1-c]chromen-9(6H)-one

Haematoxylin has no staining properties, unless it is oxidized in a process called ripening to yield haematein, which is then combined with certain chemicals called mordants. The process of oxidizing haematoxylin to haematein which is the active staining ingredient can be achieved naturally and artificially.

The combination of haematoxylin/haematein with eosin--an aniline dye--was first proposed in 1871 in a publication by Poole, forming one of the most used combinations in histology today. In 1942, George N. Papanicolaou introduced a five-dye combination, known simply as the "Pap" stain, destined to become the most commonly used in cytology and which features haematein as the nuclear stain.[9]

Michel Eugene Chevreul [13] isolated crystals of haematoxylin in 1812 but the crystal structure was not reported until 1998.[14]
The crystal structure of haematoxylin showing water molecules in the cavities when packed

In relating the contributions of Sir Robert Robinson to the chemistry of oxygen heterocycles, it must be emphasized that he appeared to have a special regard for the chemistry of brazilin (Structures). His name is on publications from 1906 until 1974 and on extensive reviews concerned with its chemistry [15-20]. Robinson's elucidation of the structure of the brazylium salts afforded the background for his later outstanding contributions to the chemistry of anthocyanidins and anthocyanins. Robinson's studies on the chemistry of haematoxylin ran very much parallel with those on brazilin. Haematoxylin was synthesized, from appropriate starting materials, by the same route as had been used for brazilin
Robinson prepared Brazilin and deduced its structure but found that Werner and Pfeiffer had proposed the same structure despite having no real chemical evidence and even though their suggested pre-cursors were found to be incorrect.

Henry Barham was appointed surgeon-major of the military forces in Jamaica around 1700. In 1715 he introduced logwood seeds from Honduras to Jamaica. Years later, in Feb 1897, it was reported in The Gleaner that the Agricultural Society had collected some red logwood seeds from Liberty Hall and sent them to Dr Emile Bucher for analysis and dye tests were carried out on these and other logwood species found in Jamaica. The Society agreed that seeds should be brought from Honduras for comparison and propagation. [21]

In 1851 the Reports on the Exhibition of the Works of Industry of All Nations showed logwood imports for the years 1848-1850. [22]

Table 1 Dye imports (cwt.) to Great Britain for 1848-1850
Dye 1848 1849 1850
Logwood 463840 479840 603800
Madder 220724 254722 261861
Cochineal 18380 18840 22451
Fustic 154320 175840  
Indigo 59127 81332 70482

Table 2 Logwood imports (cwt.) to Great Britain by country for 1849
British Guiana and West Indies 84120
British North America 4460
USA 44340
Central America 2520
Mexico 144860
Cuba 2580
Haiti 122320
Honduras 72960
Chile 420
Misc. 1260
Total 479840

The trade in logwood peaked in the late nineteenth century with Haiti accounting for 90%. During the twentieth century, demand progressively declined and exports moved from logs to extracts. The major commercial sources of logwood extracts in recent years have been the larger Caribbean islands (Jamaica, Haiti and the Dominican Republic). Other producers include several Central American countries and Brazil.

Trees are cultivated in Jamaica and some of the other islands but elsewhere in the region the industry is heavily dependent upon wild trees. [23]

The West Indies Chemical Works Ltd (WICW) in Spanish Town opened in 1893 and became a major supplier of logwood extracts for over 70 years. [24] The idea is said to have come to two Swiss graduates of the Zurich Polytechium (Francis Emile Bucher and Emile Schweich-Mond) when after attending a lecture on dyes by Georg Lunge (1839-1923) a suggestion was made that it was too wasteful to import logwood chips into Europe and shipping of the concentrated extracts could remarkably reduce costs and make a lucrative business. Alfred Werner was another of their Professors and as noted above, Pfeiffer and Werner were the first to accurately propose structures for Brazilin an analogue of Haematoxylin/Haematein. Pfeiffer later published another 15+ papers on these species.

In the obituary for Emile Schweich-Mond (1865-1938) by Bucher and Gibson, [25] the story of establishment of the factory is given. The two set up a small pilot plant in rented space in Manchester, England near to a factory that could supply steam. After determining the conditions for extraction they approached Ludwig Mond (Emile Schweich's uncle) and after his numerous suggestions of modifications to their design of the plant with respect to the location of boilers etc. they were ready to begin construction. In addition to processing logwood in 1891 they applied for a Patent in Jamaica for the processing of the heartwood of a prosopis species.

The WICW factory site was well chosen in Spanish Town with good road and rail service and a large space for the storage of large quantities of logwood. This was piled according to relative dyeing quality to allow some mixing in order to provide a fairly stable input feed. About 60 tons of wood were extracted by 4 times as much water and the spent wood was fed wet into the boilers to raise steam and electricity.

The site selected was next to the railway station. The custos of St Catherine, Thomas Lloyd Harvey (1841-1906) provided some local support and initially there were seven subscribing members of the West Indies Chemical Works. The Inaugural dinner for the opening of the plant was held at Harvey's Rio Cobre Hotel. The other members included Edward Bodmer (Bucher's father-in-law or brother-in-law), Harvey, Sidney Raynes Cargill and Franz Xavier Knecht and an eighth joined soon after. [26]
Notices in the Gleaner show that a rail sideline was built to link the Spanish Town line in to the factory. This would allow timber to travel in for processing and dye to move out to the ports for shipping. This was in addition to small boats that plied the route from Savanna-la-Mar to St Catherine carrying timber.

References

1. https://en.wikipedia.org/wiki/Haematoxylum_campechianum
2. Bart Kahr, Scott Lovell and J. Anand Subramony, "The progress of logwood extract", Chirality, 10(1-2), 66-77, 1998.
3. https://en.wikipedia.org/wiki/Belize
4. Elizabeth I Statutes
5. Black River
6. Hooke
7.
8.
9. https://en.wikipedia.org/wiki/Haematoxylin
10. https://en.wikipedia.org/wiki/Hematein
11. http://www.leicabiosystems.com/pathologyleaders/the-basic-chemistry-of-hematoxylin/
12. A. Werner and P. Pfeiffer, Chem. Z., 1904, 3, 421.
13. Chevreul, M.E. Du me´moire sur le Bois Campe´che et sur la nature de son principe colorant. Ann. Chim. 82:53-85, 126-147, 1812.
14. Bart Kahr, Scott Lovell and J. Anand Subramony, Chirality, 10(1-2), 66-77, 1998.
15. R. Livingstone, 'Anthocyanins, Brazilin, and Related Compounds', NATURAL PRODUCT REPORTS, 1987, pg 25
16. R. Robinson, in 'Chemistry of Carbon Compounds', ed. F. H.Rodd, Elsevier, Amsterdam, 1959, Vol. IVB, p. 1005.
17. R. Robinson, in 'Rodd's Chemistry of Carbon Compounds ', ed.S. Coffey, Elsevier, Amsterdam, 1977, Vol. IVE, p. 427.
18. W. H. Perkin and R. Robinson, J. Chem. Soc., 1908, 93, 489
19. P. Engels, W. H. Perkin, and R. Robinson, J. Chem. Soc., 1908, 93, 1115.
20. F. Morsingh and R. Robinson, Tetrahedron, 1970, 26, 28 1.
21. Gleaner
22. 1851 Reports
23. C.L. Green, Non-Wood Forest Products, Natural Colourants and Dyestuffs, FAO 1995
24. Gleaner
25. J. Chem. Soc., 1939, 729-731
26. Gleaner

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